AU2018201082B2

AU2018201082B2 - 6-acyl-1,2,4-triazine-3,5-dione derivative and herbicides

Info

Publication number: AU2018201082B2
Application number: AU2018201082A
Authority: AU
Inventors: Ryu Kajiki; Masami Kobayashi; Takashi Mitsunari; Atsushi Nagamatsu; Atsushi Shibayama
Original assignee: FMC Corp
Current assignee: FMC Corp
Priority date: 2010-06-29
Filing date: 2018-02-14
Publication date: 2019-11-07
Anticipated expiration: 2031-05-26
Also published as: AU2016235030B2; AU2016235030A1; AU2018201082A1

Abstract

Disclosed are compounds exhibiting sufficient herbicidal activity at low application dosage when they are applied to soils and foliage, and an agrochemical composition using the same, in particular herbicides. The compounds are triazine derivatives representedby followingFormula 1or salts thereof, and the herbicides containing them: A N'R4 wherein in the formula, R' represents a hydrogen atom; a C1 -C 1 2 alkyl group; a C 2 -C alkenyl group, etc., R 2 represents a C1-C12 alkyl group, etc., Y and Z represent an oxygen atom or a sulfur atom, and A represents a 5- or 6-membered cyclic group which may contain a nitrogen atom, an oxygen atom, or a sulfur atom. Methods using these compounds are also disclosed herein.

Description

Disclosed are compounds exhibiting sufficient herbicidal activity at low application dosage when they are applied to soils and foliage, and an agrochemical composition using the same, in particular herbicides. The compounds are triazine

2018201082 14 Feb 2018

ABSTRACT derivatives represented by following Formula 1 or salts thereof, and the herbicides containing them:

wherein in the formula, R¹ represents a hydrogen atom; a C1-C12 alkyl group; a C₂-Cg alkenyl group, etc., R represents a C1-C12 alkyl group, etc., Y and Z represent an oxygen atom or a sulfur atom, and A represents a 5- or 6-membered cyclic group which may contain a nitrogen atom, an oxygen atom, or a sulfur atom. Methods using these compounds are also disclosed herein.

325

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DESCRIPTION

Title of Invention

6-ACYL-l,2,4-TRIAZINE-3,5-DIONE DERIVATIVE AND HERBICIDES

Technical Field

The present invention relates to a novel triazine derivative or its salt, and herbicides containing it as an effective component.

Background Art

Triazine derivatives are known from Collection of Czechoslovak Chemical

Communications (1969), 34(6), 1673-83., etc., for example. However, no herbicidal activity is described for the compounds disclosed in these literatures. Although various compounds are reported as triazine-based herbicides (for example, see The Pesticide Manual 15th Edition, 2009, published by BCPC), they all have a 1,3,5-triazine ring. Specific examples of the 1,3,5-triazine-based agrochemicals include 2-chloro-4,6-bis-(ethylamino)-l,3,5-triazine (Simazine), 2-chloro-4-ethylamino-6-isopropylamino-l,3,5-triazine (Atrazin),

2.4- bis(ethylamino)-6-methylthio-l,3,5-triazine (Simetryn),

2.4- bis(isopropylamino)-6-methylthio-l,3,5-triazine (Prometryn), and 2-(l,2-dimethylpropylamino)-4-ethylamino-6-methylthio-l,3,5-triazine (Dimethametryn).

Further, as a 1,2,4-triazine-based agrochemical, there are known 4-amino-3-methyl-6-phenyl-l ,2,4-triazine-5(4H)-one (Metamitron), 4-amino-6-tert-butyl-3-methylthio-l,2,4-triazine-5(4H)-one (Metribuzin), etc. It is disclosed in Japanese Patent Application Laid-Open (JP-A) No. 8-259546 that 4-(2,4-dihalogeno-5alkoxyphenyl)-l,2,4-triazine-3,5-dione derivatives having a hydrocarbon substituent group at 6-position have a herbicidal activity. It is disclosed in JP-A No. 5-51369 that

3.5- diaryl-6-amino-l ,2,4-triazine derivatives have a herbicidal activity. It is disclosed in JP-A No. 5-32641 that 3-mercapto-l ,2,4-triazine derivatives have a herbicidal activity.

However, it is not known from any literatures that 6-acyl-l ,2,4-triazine-3,5-dione derivatives represented by Formula 1 below have a herbicidal activity.

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Citation List

Patent Literature

PLT 1: Japanese Patent Application Laid-Open No. 8-259546

PLT 2: Japanese Patent Application Laid-Open No. 5-51369

PLT 3: Japanese Patent Application Laid-Open No. 5-32641

Non Patent Literature

NPL 1: Collection of Czechoslovak Chemical Communications (1969), 34(6), 1673-83.

NPL 2: The Pesticide Manual 15thEdition (2009, published by BCPC)

Summary of Invention

Technical Problem

Herbicides used for useful crops and useful plants are required to be a chemical preparation which can be applied to soils or leaves and exhibit a sufficient herbicidal effect with low chemical dosage. Further, as there is an increasing need concerning safety and effect on environment of a chemical substance, development of safer herbicides is waited for. The invention is devised to cope with such problems.

Solution to Problem

In order to achieve the object above, inventors of the invention synthesized many triazine compounds to study the herbicidal activity of various triazine derivatives, and intensively determined the herbicidal activity and usefulness of the compounds. As a result, it is found that, when triazine derivatives of the invention are applied to weeds or soils wherein weeds thrive, an excellent herbicidal effect is obtained for a long period of time, and therefore the invention is completed accordingly.

Thus, the present invention relates to the following (1) to (43).

(1) A triazine derivative or a salt thereof represented by following Formula 1:

[Chem. 1]

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[in the formula, R¹ represents a hydrogen atom; a C1-C12 alkyl group; a C2-Q alkenyl group; a C2-C6 alkynyl group; a C₃-Cg cycloalkyl group; a C₃-Ce cycloalkenyl group; a C₃-Cg cycloalkyl Ci-Cs alkyl group; a Ci-Q haloalkyl group; a C2-C6 haloalkenyl group; a C₂-Cs haloalkynyl group; a C₃-Cs halocycloalkyl group; a C₃-Ce halocycloalkyl Ci-C₆ alkyl group; an amino Cj-Cg alkyl group; a nitro Ci-Cg alkyl group; a C1-C6 alkylamino Ci-Cg alkyl group; a di(Ci-Cs alkyl)amino Ci-Cg alkyl group; a CpCg alkylthio Ci-Cg alkyl group; a Ci-Cg alkylsulfinyl Ci-Cg alkyl group; a Ci-Cg alkylsulfonyl Ci-Cg alkyl group; a Ci-Cg haloalkylthio Cj-Cg alkyl group; a C]-Cg haloalkylsulfinyl Cj-Cg alkyl group; a Ci-Cg haloalkylsulfonyl Ci-Cg alkyl group; a Ci-Cg alkoxy Cj-Cg alkyl group; a hydroxy Ci-Cg alkyl group; a phenyl Ci-Cg alkoxy Ci-Cg alkyl group (phenyl in the group may be substituted with one substituent group selected from Substituent group a or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group a); a Ci-Cg alkoxy Ci-Cg alkoxy Ci-Cg alkyl group; a C₃-Cg cycloalkyloxy Ci-C₆ alkyl group; a C₃-Cg cycloalkyl Ci-Cg alkyloxy Ci-C₆ alkyl group; a phenyloxy Ci-Cg alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a); a phenylthio Ci-Cg alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a); a phenylsulfinyl Ci-Cg alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a); a phenylsulfonyl Ci-Cg alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a); a Ci-Cg haloalkoxy Cj-Cg alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; a phenyl Ci-C₆ alkyl group which may be substituted with one or more substituents selected from the Substituent group a; a phenyl C2-C6 alkenyl group which may be substituted with one or more substituents selected from the Substituent group a; a

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PCT/JP2011/062643

2018201082 14 Feb 2018 phenyl Cz-Cg alkynyl group which may be substituted with one or more substituents selected from the Substituent group a; a Ci-Cg alkoxyimino Cj-Cg alkyl group; a phenoxyimino Ci-Cg alkyl group which may be substituted with one or more substituents selected from the Substituent group a; a di(Ci-Cg alkoxy)Ci-Cg alkyl group; a (R³¹R³²N-C=O)Ci-Cg alkyl group; a C,-Cg alkoxycarbonyl Cj-Cg alkyl group; a Ci-Cg alkylcarbonyl Ci-Cg alkyl group; a Ci-Cg alkylcarbonyloxy Ci-Cg alkyl group; a Ci-Cg alkylidene aminooxy Ci-Cg alkyl group; a formyl Ci-Cg alkyl group; a Cj-Cg alkylthio Ci-Cg alkoxy Ci-Cg alkyl group; a Ci-Cg alkylsulfinyl Ci-Cg alkoxy Ci-Cg alkyl group; a Ci-Cg alkylsulfonyl Ci-Cg alkoxy Ci-Cg alkyl group; a cyano Cj-Cg alkoxy Ci-Cg alkyl group; a cyano Ci-Cg alkyl group; a C₂-Cg alkylidene amino group; a di(Ci-Cio alkyl)amino Cj-Cg alkylidene amino group; a NR³¹R³² group; a Ci-Cg alkoxy group; a C₂-Cg alkenyloxy group; a C₂-Cg alkynyloxy group; a C₃-C₆ cycloalkyloxy group; a C₃-C₆cycloaikyl Ci-C₆ alkyloxy group; a Ci-C₆ haloalkoxy group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone]; a Ci-Cg alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a]; a Cj-Cg alkoxy Ci-Cg alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a]; or a Ci-Cg alkoxy Ci-Cg alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a];

R² represents a hydrogen atom; a C]-Cg alkyl group; a C₂-Cg alkenyl group; a C₂-Cg alkynyl

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PCT/JP2011/062643 group; a C₃-Cg cycloalkyl group; a Cj-Cg haloalkyl group; a C₂-Cg haloalkenyl group; a C₂-C₆ haloalkynyl group; a Cj-Cg alkoxy Ci-Cg alkyl group; a C3-Cg cycloalkyloxy Cj-Cg alkyl group; a di(Ci-Cg alkoxy) Ci-Cg alkyl group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a); a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; a phenyl Ci-Cg alkyl group which may be substituted with one or more substituents selected from the Substituent group a; a phenyl C₂-Cg alkenyl group which may be substituted with one or more substituents selected from the Substituent group a; or a phenyl C₂-Cg alkynyl group which may be substituted with One or more substituents selected from the Substituent group a,

Y and Z represent an oxygen atom or a sulfur atom, “A” represents any one of the following formula A-1 to A-5,

A-3

A-4

A-5

R⁴ represents a hydroxyl group; O'M⁺ (M⁺ represents an alkali metal cation or an ammonium cation); an amino group; a halogen atom; a cyano group; an isothiocyanate group; an isocyanate group; a hydroxycarbonyloxy group; a Cj-Cg alkoxycarbonyloxy group; a benzyloxycarbonyloxy group which may be substituted with a substituent group selected from Substituent group a; a Ci-Cg alkoxy group; a C₂-Cg alkenyloxy group; a C₂-Cg alkynyloxy group; a C3-C6 cycloalkyloxy group; a cyanomethylene oxy group; a C3-C6 cycloalkyl Cj-Cg alkyloxy group; a Ci-Cg alkylcarbonyloxy group; a Cj-Cg haloalkylcarbonyloxy group; a C₂-Cg alkenylcarbonyloxy group; a C₂-Cg haloalkenylcarbonyloxy group; a C₂-Cg alkynylcarbonyloxy group; a C₂-Cg haloalkynylcarbonyloxy group; a Cj-Cg alkoxycarbonyl Cj-Cg alkoxy group; a phenyloxy group which may be substituted with one or more substituents selected from the Substituent group a; a benzyloxy group which may be substituted with one or more substituents

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PCT/JP2011/062643 selected from the Substituent group a; a phenylcarbonyloxy group which may be substituted with one or more substituents selected from the Substituent group a; a benzylcarbonyloxy group which may be substituted with one or more substituents selected from the Substituent group a; a phenylcarbonyl Ci-Cg alkyloxy group which may be substituted with one or more substituents selected from the Substituent group a; a Ci-Cio alkylsulfonlyoxy group; a Ci-Cg haloalkylsulfonlyoxy group; a phenylsulfonyloxy group which may be substituted with one or more substituents selected from the Substituent group a; a benzylsulfonyloxy group which may be substituted with one or more substituents selected from the Substituent group a; a Ci-Cio alkylthio group; a Ci-Cio alkylsulfinyl group; a Ci-Cio alkylsulfonyl group; a Ci-Ce haloalkylthio group; a Ci-Cg haloalkylsulfinyl group; a Ci-Ce haloalkylsulfonyl group; a C₂-C6 alkenylthio group; a C2-C6 alkenylsulfinyl group; a C2-C6 alkenylsulfonyl group; a C2-C6 alkynylthio group; a C₂-Cs alkynylsulfinyl group; a C2-C6 alkynylsulfonyl group; a phenylthio group which may be substituted with one or more substituents selected from the Substituent group a; a benzylthio group which may be substituted with one or more substituents selected from the Substituent group a; a phenylsulfinyl group which may be substituted with one or more substituents selected from the Substituent group a; a benzylsulfinyl group which may be substituted with one or more substituents selected from the Substituent group a; a phenylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group a; a benzylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group a; a Cj-Cio alkylamino group; a di(Cj-Cio alkyl)amino group; a Cj-Cg alkoxycarbonylamino group; a Ci-C% alkoxy group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a); a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a); or a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur

WO 2012/002096 7 PCT/JP2011/062643 atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a),

Ai represents a group represented by the following formula [Chem. 3]

R⁵ R⁶	R⁷
—c-	—N—
[XiJ

A2 represents a group represented by the following formula

[Chem. 4] ^R \ /^R9 —c—	O (O)n R³³ II II I —c— —S— —O— —N—
[X3]	[ X4 ] [X5] E X₆ ] [ X 7 ]

A3 represents a group represented by the following formula [Chem. 5]

R³⁴	r³⁵^_zr³⁶
-N—
[Xe]	[X9 J

n represents 0, 1, or 2,

R⁵, R⁶, R⁸, R⁹, R³⁵ and R³⁶ each independently represent a hydrogen atom or a Ci-Cg alkyl group, herein, R⁵ and R⁸ may be joined together to form a Cj-Cj alkylene chain or a C2-C5 alkenylene chain, and may form a ring together with adjacent carbon atoms, and R⁵ and R³⁵ may be joined together to form a C1-C5 alkylene chain to form a ring with adjacent carbon atoms,

R⁷, R³³, and R³⁴ each independently represent a hydrogen atom, a Cj-Cg alkyl group, a Cj-Cg haloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, or a CpCg alkoxy group,

R¹⁴, R¹⁵, R¹⁶, and R¹⁷ each independently represent a hydrogen atom, a Cj-Cg alkyl group, a C]-Cg alkoxy group, or a benzyl group which may be substituted with one or more substituents selected from the Substituent group a,

R¹⁸ represents a hydrogen atom, a Ci-C₆ alkyl group, a C₂-Cg alkenyl group, a C₂-C₆ alkynyl

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PCT/JP2011/062643 group, a cyanomethyl group, or a benzyl group,

R²⁰ represents a C]-Cg alkyl group, a Ci-Cg alkenyl group, a C2-Cg alkynyl group, a C₃-Cg cycloalkyl group, or a C₃-C₆ cycloalkyl Ci-Ce alkyl group,

R²¹ represents a hydrogen atom, a Ci-Cg alkyl group, or a halogen atom,

R²³ represents a Ci-Cg alkyl group, a Cj-Cg haloalkyl group, a C₃-Cg cycloalkyl group, a C1-C10 alkylthio group, a C1-C10 alkylsulfinyl group, a C1-C10 alkylsulfonyl group, a phenylthio group which may be substituted with one or more substituents selected from the Substituent group a, a benzylthio group which may be substituted with one or more substituents selected from the Substituent group a, a phenylsulfinyl group which may be substituted with one or more substituents selected from the Substituent group a, a benzylsulfinyl group which may be substituted with one or more substituents selected from the Substituent group a, a phenylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group a, or a benzylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group a,

R²⁴ represents a hydrogen atom, a halogen atom, a cyano group, a Ci-Cg alkyl group, a C₃-Cg cycloalkyl group, or a Ci-C₆ alkoxycarbonylamino group,

R²⁵ represents a CpCg alkoxycarbonyl group, a cyano group, or a nitro group,

1*1

R and R each independently represent a hydrogen atom; a Cj-Cg alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; a benzyl group which may be substituted with one or more substituents selected from the Substituent group a; a Ci-Cg alkoxy Ci-Cg alkyl group; a Ci-Cg alkylcarbonyl group; a C1-C10 alkylthio carbonyl group; a Cj-Cg alkoxycarbonyl group; a Ci-Cg haloalkyl group; a C₃-Cg cycloalkyl group; a C₃-Cg cycloalkyl Ci-Cg alkyl group; a Cj-Cg alkylsulfonyl group; a phenylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group a; a benzylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group a; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a); or a C]-Cg alkyl group substituted with a

WO 2012/002096

PCT/JP2011/062643 heterocyclic group in which the heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a), herein, R³¹ and R³² may be joined together to form a 5- to 6-membered ring with adjacent nitrogen atom, and the one or more carbon atoms in the ring may be substituted with a sulfur atom and/or an oxygen atom.

Herein, Substituent group a represents a group selected from a group consisting of:

a halogen atom; a hydroxyl group; a Ci-Cg alkyl group; a C3-C6 cycloalkyl group; a C3-C6 cycloalkyl Ci-Cg alkyl group; a C₂-C₆ alkenyl group; a C₂-Cg alkynyl group; a Ci-C₆ haloalkyl group; a C₂-Cg haloalkenyl group; a C₂-Cg haloalkynyl group; a C3-C6 halocycloalkyl group; a C3-C6 halocycloalkyl Ci-Ce alkyl group; a Ci-Cg alkoxy group; a C3-C6 cycloalkyloxy group; a C₂-Cg alkenyloxy group; a C₂-Cg alkynyloxy group; a Ci-C₆ alkylcarbonyloxy group;a C]-C₆haloalkoxy group; a Ci-Cg alkylthio group; a Ci-Cg alkylsulfinyl group; a Ci-Cg alkylsulfonyl group; a Cj-Cg haloalkylthio group; a Ci-Cg haloalkylsulfinyl group; a Q-Cg haloalkylsulfonyl group; an amino group; a Cj-Cg alkylcarbonylamino group; a mono(C]-Cg alkyljamino group; a di(Ci-Cg alkyljamino group; a hydroxy Ci-Cg alkyl group; a Cj-Cg alkoxy Ci-Cg alkyl group; a C]-C₆ alkylthio Ci-C₆ alkyl group; a Ci-Cg alkylsulfinyl C]-C₆ alkyl group; a Ci-Cg alkylsulfonyl Ci-Cg alkyl group; a Gj-Cg haloalkylthio Ci-Cg alkyl group; a Ci-Cg haloalkylsulfinyl Ci-Cg alkyl group; a C_rCg haloalkylsulfonyl Ci-Cg alkyl group; a cyano Ci-Cg alkyl group; a Ci-Cg alkoxy Ci-Cg alkoxy group; a C3-C6 cycloalkyl Cj-Cg alkyloxy group; a Cj-Cg haloalkoxy Ci-Cg alkoxy group; a cyano Ci-Cg alkoxy group; a Ci-Cgacyl group; a Ci-Cg alkoxyimino Ci-Cg alkyl group; a carboxyl group; a Ci-Cg alkoxycarbonyl group; a carbamoyl group; a mono(Ci-Cg alkyl)aminocarbonyl group; a di(Ci-Cg alkyljaminocarbonyl group; a nitro group; a cyano group; a phenyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group β); a heterocyclic group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group β); a heterocyclic oxy group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur

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PCT/JP2011/062643 atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group β); and a Cj-C^ alkylene group formed with two adjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group; and

Substituent group β represents a group selected from a group consisting of: a halogen atom, a nitro group, a cyano group, a Ci-Cg alkyl group, a Ci-Cg haloalkyl group, a Ci-Cg alkoxy group, and a Ci -Cg haloalkoxy group.].

(2) The triazine derivative or the salt thereof according to (1), wherein A in Formula 1 is A-1.

(3) The triazine derivative or the salt thereof according to (1) or (2), wherein in A-l, Ai is [Xi], Az is [X₃], and A3 is [Xg].

(4) The triazine derivative or the salt thereof according to (3), wherein R⁵ and R⁶ in [Xi] is a hydrogen atom or a Ci-C5 alkyl group, R⁸ and R⁹ in [X3] is a hydrogen atom or a Ci-C₆ alkyl group, and R³⁵ and R³⁶ in [X₉] is a hydrogen atom or a Ci-C₆ alkyl group, or R⁵ and R³⁵ may bind to each other via a C1-C5 alkylene chain to form a ring.

(5) The triazine derivative or the salt ±ereof according to (1), wherein A in Formula 1 is A-3.

(6) The triazine derivative or the salt thereof according to (5), wherein R²⁰ in A-3 is a Ci-C₆alkyl group, and R21 in A-3 is a hydrogen atom or a Ci-Cg alkyl group.

(7) The triazine derivative or the salt thereof according to any one of (1) to (6), wherein R⁴ in A-l is a hydroxyl group or an O7Vi⁺(M⁺represents an alkali metal cation or an ammonium cation).

(8) The triazine derivative or the salt thereof according to any one of (1) to (7), wherein Y in Formula 1 is an oxygen atom.

(9) The triazine derivative or the salt thereof according to any one of (1) to (8), wherein R¹ in Formula 1 is the group selected from the group consisting of a C1-C12 alkyl group; a C₂-Cg alkenyl group; a C₂-C₆ alkynyl group; a C3-C6 cycloalkyl group; a C₃-C₆ cycloalkenyl group; a Ci-Cs haloalkyl group; a C₂-Cg haloalkenyl group; a Ci-Cg alkoxy C_rCg alkyl group; a Cj-Cg alkylthio Ci-Cg alkyl group; a Cj-Cg alkylsulfinyl Ci-Cg alkyl group; a Cj-Cg alkylsulfonyl Ci-Cg alkyl group; a Ci-C₆ alkoxycarbonyl Ci-Cg alkyl group; a phenyl group which may be substituted

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PCT/JP2011/062643 with one or more substituents selected from the Substituent group a; a phenyl Cj-Cg alkyl group which may be substituted with one or more substituents selected from the Substituent group a; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a, and when ±e heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone].

(10) The triazine derivative or the salt thereof according to any one of (1) to (9), wherein R² in Formula 1 is the group selected from the group consisting of a Ci-Cg alkyl group; a Ci-Cg haloalkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom(the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a).

(11) The triazine derivative or the salt thereof according to (1), in which the groups in Formula 1 are as follows: R¹ represents a C1-C12 alkyl group; a C₂-Cg alkenyl group; a C₂-C₆alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₃-C₆ cycloalkyl C]-C₆alkyl group; a Ci-Cg haloalkyl group; a C₂-C6 haloalkenyl group; a C₂-Cg haloalkynyl group; a C3-C6 halocycloalkyl group; a Ci-C₆ alkylthio Ci-C₆ alkyl group; a Ci-Cg alkylsulfinyl Ci-Cg alkyl group; a Ci-C₆ alkylsulfonyl C]-C₆ alkyl group; a Cj-Cg alkoxy Ci-Cg alkyl group; a Cj-Cg alkoxy Cj-Cg alkoxy Ci-Cg alkyl group; a C3-C6 cycloalkyloxy Ci-Cg alkyl group; a phenyloxy Ci-Cg alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a); a phenylthio Ci-Cg alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a); a phenylsulfinyl Ci-Cg alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a); a phenylsulfonyl Ci-Cg alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a); a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; a

2018201082 14 Feb 2018

WO 2012/002096 12 PCT/JP2011/062643 phenyl Ci-Ce alkyl group which may be substituted with one or more substituents selected from the Substituent group a ;a phenyl C₂-Cg alkenyl group which may be substituted with one or more substituents selected from the Substituent group a; a phenyl C₂-Ci alkynyl group which may be substituted with one or more substituents selected from the Substituent group a; a Ci-Q alkoxyimino Ci-C₆ alkyl group; a di(Ci-Cg alkoxy) Ci-Cg alkyl group; a Ci-C_salkoxycarbonyl Ci-C_s alkyl group; a Ci-Cg alkylcarbonyl Ci-Cg alkyl group; a Ci-Cg alkylcarbonyloxy Cj-Cg alkyl group; a NR³¹R³² group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom(the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone); or a Ci-Cg alkyl group substituted with a heterocyclic group in which the heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a);

R² represents a hydrogen atom; a Ci-Cg alkyl group; a C₂-Ce alkenyl group; a C₂-C₆ alkynyl group; a C3-C6 cycloalkyl group; a Ci-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆haloalkynyl group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a); a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; or a phenyl Ci-Cg alkyl group which may be substituted with one or more substituents selected from the Substituent group a;

Y and Z represent an oxygen atom or a sulfur atom,

A represents any one of A-l, A-3, and A-5,

Ai is [Xi],

A₂ is [X3] or [X4], and

A₃ is [X₉], in [Xi], R⁵ and R⁶ each independently represent a hydrogen atom or a Ci-Cg alkyl group,

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PCT/JP2011/062643 in [X3], R⁸ and R⁹ each independently represent a hydrogen atom or a Ci-Cg alkyl group, in [X9], R³⁵ and R³⁶ each independently represent a hydrogen atom or a Cj-Cg alkyl group, herein, R⁵ and R⁸ may be joined together to form a C2-C5 alkylene chain or a C2-C5 alkenylene chain, and may form a ring together with adjacent carbon atoms, and R⁵ and R³⁵ may be joined together to form a C1-C5 alkylene chain to form a ring with adjacent carbon atoms, in A-3, R²⁰ is a Ci-Cg alkyl group,

R²¹ is a hydrogen atom or a Ci-Cg alkyl group, in A-5, R²⁴ represents a hydrogen atom, a Cj-Cg alkyl group, or a Cj-Cg cycloalkyl group, R²⁵ represents a Cj-Cg alkoxycarbonyl group, a cyano group, or a nitro group,

R⁴ represents a hydroxyl group; (yM⁺(M⁺ represents an alkali metal cation or an ammonium cation); or a C1-C10 alkylsulfonlyoxy group;

R³¹ and R³² each independently represent a hydrogen atom; a C]-Cg alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; or a benzyl group which may be substituted with one or more substituents selected from the Substituent group a; herein, R³¹ and R³² may be joined together to form a 5- to 6-membered ring with adjacent nitrogen atom, and the one or more carbon atoms in the ring may be substituted with a sulfur atom and/or an oxygen atom, herein, Substituent group a represents a group selected from a group consisting of:

a halogen atom; a Cj-Cg alkyl group; a C3-C6 cycloalkyl group; a C₂-Cg alkenyl group; a C₂-Cg alkynyl group; a Ci-Cg haloalkyl group; a C₂-Cg haloalkenyl group; a C₂-Cg haloalkynyl group; a C3-C6 halocycloalkyl group; a Ci-Cg alkoxy group; a C3-C6 cycloalkyloxy group; a C₂-Cg alkenyloxy group; a C₂-Cg alkynyloxy group; a Ci-Cg haloalkoxy group; a Cj-Cg alkylthio group; a Ci-Cg alkylsulfinyl group; a Ci-Cg alkylsulfonyl group; a nitro group; a cyano group; a phenyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group β); a heterocyclic oxy group comprising 2 to 10 carbon atoms and 1 to 5 heteroatoms that are optionally selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group β); and a C3-C6 alkylene group formed with two adjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylene group may be

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WO 2012/002096 14 PCT/JP2011/062643 substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group.

(12) The triazine derivative or the salt thereof according to (1), in which the groups in

Formula 1 are as follows:

R¹ is a group selected from a group consisting of a Ci-Cu alkyl group; a C2-C6 alkenyl group; a C₂-C₆ alkynyl group; a C₃-C_fi cycloalkyl group; a C₃-Cg cycloalkenyl group; a Ci-C₆haloalkyl group; a C2-C6 haloalkenyl group; a Ci-Cg alkylthio Cj-Cg alkyl group; a C,-Cg alkylsulfinyl Ci-Cg alkyl group; a Ci-Cg alkylsulfonyl Cj-Cg alkyl group; a Ci-Cg alkoxy Ci-Cg alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; a phenyl Cj-Cg alkyl group which may be substituted with one or more substituents selected from the Substituent group a; a Ci-Cg alkoxyimino Ci-Cg alkyl group; a Ci-Cg alkoxycarbonyl Ci-Cg alkyl group; a Ci-Cg alkylcarbonyl Ci-Cg alkyl group; a NR³¹R³²group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone); and, a Ci-Cg alkyl group substituted with a heterocyclic group in which the heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a);

R³¹ and R³² each independently represent a group selected from a group consisting of a hydrogen atom; a Ci-Cg alkyl group; and, a phenyl group which may be substituted with one or more substituents selected from the Substituent group a;

R represents a group selected from a group consisting of a Ci-Cg alkyl group; a C₂-Cg alkenyl group; a C2-Cg alkynyl group; a C₃-Cg cycloalkyl group; a Ci-Cg haloalkyl group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a);

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PCT/JP2011/062643 and, a phenyl group which may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a;

Y and Z represent an oxygen atom or a sulfur atom,

A represents any one of A-l, A-3, and A-5,

R⁴ in A-l represents a hydroxyl group;

0M⁺(M⁺ represents an alkali metal cation or an ammonium cation);

or a Ci-Cio alkylsulfonyloxy group;

in A-l, Ai is [Xi],

A₂ is [X₃] or [X4], and

A₃ is [X₉], in [Xi], R⁵ and R⁶ each independently represent a hydrogen atom or a Ci-Cg alkyl group, in [X3], R⁸ and R⁹ each independently represent a hydrogen atom or a Ci-Cg alkyl group, in [X9], R³⁵ and R³⁶ each independently represent a hydrogen atom or a Ci-Cg alkyl group, herein, R^s and R⁸ may bind to each other via a C2-C5 alkylene chain or a C2-C5 alkenylene chain to form a ring, and R⁵ and R³⁵ may bind to each other via a C4-C5 alkylene chain to form a ring, in A-3, R²⁰ is a Ci-C₆ alkyl group,

R²¹ is a hydrogen atom or a Ci-Cg alkyl group, and

R⁴ represents a hydroxyl group; 0·Μ⁺(Μ⁺ represents an alkali metal cation or an ammonium cation); or a C1-C10 alkylsulfonlyoxy group;

Substituent group a represents a group selected from a group consisting of: a halogen atom; a Ci-Cg alkyl group; a C2-C6 alkenyl group; a C2-Cg alkynyl group; a Ci-Cg haloalkyl group; a Ci-Cg alkoxy group; a Ci-Cg haloalkoxy group; a Ci-Cg alkylthio group; a Ci-Cg alkylsulfinyl group; a Ci-Cg alkylsulfonyl group; a nitro group; a cyano group; a phenyl group; and a C₃-Cg alkylene group formed with two adjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group.

(13) The triazine derivative or the salt thereof according to (1), in which the groups in

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PCT/JP2011/062643

Formula 1 are as follows:

R¹ represents a group selected from a group consisting of a C1-C12 alkyl group; a C₂-Cg alkenyl group; a C2-C6 alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-Cg cycloalkenyl group; a Ci-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a Ci-Cg alkylthio Cj -C₆ alkyl group; a Ci-Cg alkylsulfinyl Ci-Cg alkyl group; a Ci-Cg alkylsulfonyl Ci-Cg alkyl group; a Ci-Cg alkoxy Ci-Cg alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; a phenyl C_rCg alkyl group; a Ci-Cg alkoxyimino Ci-Cg alkyl group; a Ci-Cg alkoxycarbonyl Ci-Cg alkyl group; a Ci-Cg alkylcarbonyl Ci-Cg alkyl group; a NR³¹R³² group; a heterocyclic group selected from the group consisting of pyridyl group, pyrimidinyl group, pyridazinyl group, thienyl group, isoxazolyl group, pyrazolyl group, morpholinyl group, thiomorpholinyl group, pyrazinyl group, piperidinyl group, and pyperazinyl group (the heterocyclic group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone); and, a tetrahydrofuryl-methyl group;

R and R each independently represent a group selected from a group consisting of a hydrogen atom; a Cj-C₅ alkyl group; and a phenyl group;

R² represents a group selected from a group consisting of a Ci-Cg alkyl group; a Ci-Cg haloalkyl group; a pyridyl group; and a phenyl group;

Y and Z represent an oxygen atom or a sulfur atom,

A represents any one ofA-1 and A-3,

R⁴ in A-l represents a hydroxyl group; or a C4-C10 alkylsulfonlyoxy group, in A-1, Ai is [Xi], A₂ is [X3] or [X4], and A₃ is [X9], in [Xi], R⁵ and R⁶ are a hydrogen atom or a Ci-Cg alkyl group, in [X3], R and R are a hydrogen atom or a Cj-Cg alkyl group, in [X9], R³⁵ and R³⁶ are a hydrogen atom or a CpCg alkyl group, herein, R⁵ and R⁸ may be joined together to form a C2-C5 alkylene chain and to form a ring, and R⁵ and R³⁵ may be joined together to form a C1-C5 alkylene chain and to form a ring, in A-3, R²⁰ is a Ci-Cg alkyl group, R²¹ is a hydrogen atom or a Ci-Cg alkyl group, and R⁴

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PCT/JP2011/062643 represents a hydroxyl group or a Ci-Cio alkylsulfonlyoxy group, and

Substituent group a represents a group selected from a group consisting of: a halogen atom; a C]-C₆ alkyl group; a C₂-Ce alkenyl group; a C₂-C₆ alkynyl group; a Ci-C₆ haloalkyl group; a C1-C6 alkoxy group; a Ci-C₆ haloalkoxy group; a Ci-C₆ alkylthio group; a Ci-C₆alkylsulfinyl group; a Ci-Ce alkylsulfonyl group; a nitro group; a cyano group; a phenyl group; and a methylenedioxy group.

(14) An agrochemical composition comprising the triazine derivative or the salt thereof described in any one of (1) to (13), and an agriculturally acceptable carrier.

(15) The agrochemical composition according to (14), in which the agrochemical composition further comprises a surface active agent.

(16) A herbicide comprising the triazine derivative or the salt thereof described in any one of (1) to (13) as an active component.

(17) The herbicide according to (16), in which the herbicide has a herbicidal activity for weeds in a field or a paddy field in which agrohorticultural plants are cultivated.

(18) The herbicide according to (17), in which the agrohorticultural plants are agrohorticultural plants given with resistance by a breeding method or a genetic recombination technique.

(19) A method of eliminating weeds in soils by applying an effective amount of herbicides comprising the triazine derivative or the salt thereof described in any one of (16) to (18).

(20) The method according to (19), in which the soils are a farmland.

(21) The method according to (19), in which the farmland is a field or a paddy field in which agrohorticultural plants are cultivated.

(22) A triazine derivative or a salt thereof represented by following Formula 2:

[Chem. 6]

[2] [in the formula, B represents a hydroxyl group or a Ci-Ce alkoxy group and R¹, R², Y, and Z have the same definitions as those described in above Formula 1],

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PCT/JP2011/062643 (23) The triazine derivative or the salt thereof according to (22), wherein Y in Formula 2 is an oxygen atom.

(24) The triazine derivative or the salt thereof according to (22) or (23), wherein R¹ in Formula 2 represents a group selected from a group consisting of a Cj-Cu alkyl group; a Ci-Cg alkenyl group; a Cj-Cg alkynyl group; a C3-Cg cycloalkyl group; a C3-Cg cycloalkenyl group; a Ci-Cg haloalkyl group; a Ci-Cg haloalkenyl group; a C1-C6 alkoxy Ci-Ce alkyl group; a Cj-Cg alkylthio Ci-Cg alkyl group; a Ci-Cg alkylsulfinyl Cj-Cg alkyl group; a Ci-Cg alkylsulfonyl Ci-Cg alkyl group; a Cj-Cg alkoxycarbonyl Ci-Cg alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; a phenyl Ci-C₆ alkyl group which may be substituted with one or more substituents selected from the Substituent group a; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone ).

(25) The triazine derivative or the salt thereof according to any one of (22) to (24), wherein R² in Formula 2 represents a group selected from a group consisting of a Ci-Cg alkyl group; a Ci-Cg haloalkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a).

(26) The triazine derivative or the salt thereof according to (22) or (23), wherein B is a hydroxyl group and R² is a Ci-Cg alkyl group.

(27) The triazine derivative or the salt thereof according to (26), wherein R¹ represents a group selected from a group consisting of a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; a phenyl Ci-Cg alkyl group which may be substituted with one or more substituents selected from the Substituent group a; a C;-Cg alkoxyimino Ci-Cg alkyl group; a Ci-Cg alkoxycarbonyl Ci-Cg alkyl group; a Ci-Cg

WO 2012/002096

PCT/JP2011/062643 alkylcarbonyl Cj-Cg alkyl group; a Cj-Cg alkylcarbonyloxy Ci-Cg alkyl group; a C_rC₆alkylidene aminooxy Ci-Cg alkyl group; aNR³¹R³² group; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone ].

(28) The triazine derivative or the salt thereof according to (26), wherein R¹ represents a group selected from a group consisting of a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; a C]-C₆ alkoxyimino C]-C₆ alkyl group; a Ci-Cg alkylcarbonyl Ci-Cg alkyl group; aNR³¹R³² group; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone ].

(29) The triazine derivative or the salt thereof according to (27) or (28), wherein a heterocyclic group is 5- or 6-membered aromatic heterocyclic group having 1 to 3 nitrogen atoms as a heteroatom.

(30) The triazine derivative or the salt thereof according to any one of (26) to (29), wherein R³¹and R³² each independently represent a hydrogen atom; a Ci-Cg alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; a benzyl group which may be substituted with one or more substituents selected from the Substituent group a; a Ci-C₆ alkylcarbonyl group; a Ci-C₆ alkoxycarbonyl group; a Ci-Cg haloalkyl group; a C3-C6 cycloalkyl group; a C3-C6 cycloalkyl Cj-Q alkyl group; or R³¹ and R³²may be joined together to form a 5- to 6-membered ring with adjacent nitrogen atom, and in such case, one or more carbon atom in the ring may be substituted with a sulfur atom and/or an oxygen atom.

(31) The triazine derivative or the salt thereof according to (30), wherein R³¹ and R³² each independently represent a hydrogen atom; a Ci-Cg alkyl group; or a phenyl group which may be substituted with one or more substituents selected from the Substituent group a.

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PCT/JP2011/062643 (32) The triazine derivative or the salt thereof according to any one of (26) to (31), wherein Substituent group a represents a group selected from a group consisting of a halogen atom; a Ci-Ce alkyl group; a C3-C6 cycloalkyl group; a C3-C6 cycloalkyl Ci-Cg alkyl group; a Ci-Cg haloalkyl group; a C3-C6 halocycloalkyl group; a C₃-Cg halocycloalkyl Ci-Cg alkyl group; a Cj-Cg alkoxy group; a C3-C6 cycloalkyloxy group; a Cj-Cg haloalkoxy group; a C1-C5 alkylthio group; a Ci-Cg haloalkylthio group; a Cj-Cg alkoxy Ci-Cg alkyl group; a Ci-Cg alkylthio Ci-Cg alkyl group; or a C3-C6 alkylene group formed with two adjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group.

(33) The triazine derivative or the salt thereof according to (32), wherein Substituent group a represents a group selected from a group consisting of a halogen atom; a Cj-Cg alkyl group; a Ci-Cg haloalkyl group; a Ci-Cg alkoxy group; or a Ci-Cg alkylthio group.

(34) The triazine derivative or the salt thereof according to any one of (22) to (33), wherein

Y in Formula 2 is an oxygen atom,

R¹ in Formula 2 represents a group selected from a group consisting of a C1-C12 alkyl group; a C2-C6 alkenyl group; a C₂-Cg alkynyl group; a C3-C6 cycloalkyl group; a C3-C6 cycloalkenyl group; a Ci-Cg haloalkyl group; a C₂-Cg haloalkenyl group; a Cj-Cg alkoxy C)-Cg alkyl group; a Ci-Cg alkylthio Ci-Cg alkyl group; a Cj-Cg alkylsulfinyl Cj-Cg alkyl group; a Cj-Cg alkylsulfonyl Ci-Cg alkyl group; a Cj-Cg alkoxyimino Ci-Cg alkyl group; a Ci-Cg alkoxycarbonyl Ci-Cg alkyl group; a Ci-Cg alkylcarbonyl Ci-Cg alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; a phenyl Ci-Cg alkyl group which may be substituted with one or more substituents selected from the Substituent group a; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone); and

R² in Formula 2 represents a group selected from a group consisting of a C, -Cg alkyl group;

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PCT/JP2011/062643 a Ci-Cfi haloalkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a).

(35) The triazine derivative or the salt thereof according to any one of (22) to (34), wherein

Y in Formula 2 is an oxygen atom,

R¹ in Formula 2 represents a group selected from a group consisting of a Ci-Cn alkyl group; a C₂-Cfi alkenyl group; a C₂-C₆ alkynyl group; a C₃-Ce cycloalkyl group; a C₃-C₆cycloalkenyl group; a Cj-Cg haloalkyl group; a C₂-C6 haloalkenyl group; a Ci-Cg alkoxy Ci-C₆alkyl group; a Cj-Cg alkylthio Ci-Cg alkyl group; a Ci-Cg alkylsulfinyl Ci-Q alkyl group; a Cj-Cg alkylsulfonyl Cj-Cg alkyl group; a Ci-Cg alkoxyimino Ci-Cg alkyl group; a Ci-C₆ alkoxycarbonyl Ci-Cg alkyl group; a Ci-Cg alkylcarbonyl Ci-Cg alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group a; a phenyl C]-Cg alkyl group which may be substituted with one or more substituents selected from the Substituent group a; and a heterocyclic group selected from the group consisting of pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, thienyl group, thiazolyl group, isoxazolyl group, pyrazolyl group, morpholinyl group, thiomorpholinyl group, and pyperazinyl group (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone);

R² is a group selected from a group consisting of a Ci-Cg alkyl group; a Ci-Cg haloalkyl group; and a pyridyl group; and,

Substituent group a represents a group selected from a group consisting of a halogen atom; a Ci-Cg alkyl group; a C₂-Cg alkenyl group; a C₂-Cg alkynyl group; a Ci-Cg haloalkyl group; a Ci-Cg alkoxy group; a Ci-Cg haloalkoxy group; a Cj-Cg alkylthio group; a Cj-Cg alkylsulfinyl group; a Ci-Cg alkylsulfonyl group; a nitro group; a cyano group; a phenyl group; and a methylenedioxy group.

(36) An agrochemical composition comprising the triazine derivative or the salt thereof described

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PCT/JP2011/062643 in any one of (22) to (35), and an agriculturally acceptable carrier.

(37) The agrochemical composition according to (36), in which the agrochemical composition further comprises a surface active agent.

(38) A herbicide comprising the triazine derivative or the salt thereof described in any one of (22) to (35) as an active component.

(39) The herbicide according to(38), in which the herbicide has a herbicidal activity for weeds in a field or a paddy field in which agrohorticultural plants are cultivated.

(40) The herbicide according to (39), in which the agrohorticultural plants are agrohorticultural plants given with resistance by a breeding method or a genetic recombination technique.

(41) A method of eliminating weeds in soils by applying an effective amount of herbicides comprising the triazine derivative or the salt thereof described in any one of (22) to (35).

(42) The method according to (41), in which the soils are a farmland.

(43) The method according to (41), in which the farmland is a field or a paddy field in which agrohorticultural plants are cultivated.

Advantageous Effects of Invention

The invention provides the novel triazine derivative represented by Formula 1 or its salt which can effectively control weeds. The triazine derivative of the invention or its salt exhibits an excellent herbicidal effect against various weeds, which cause a problem particularly in an agricultural field over a long period of time from a pre-germination stage to a growing stage, for example, a broad-leaf weed like white pepper, Amaranthus viridis, white goosefoot, Stellaria media, chamomile, China jute, Sida spinosa, sesbania, hogweed, red poppy, morning glory, and cocklebur, annual and perennial weeds of Cyperus microiria family including coco grass, edible galingale, Kyllinga brevifolia var. leiolepis, java galingale, and Cyperus iria, and gramineous weeds like barnyard millet, finger grass, foxtail, spear grass, Syrian sorghum nitidum, short awn, and wild oat. In addition, it can control rice paddy weeds including annual weeds like Echinochloa oryzicola, Cyperus difformis, and Monochoria vaginalis and perennial weeds like Sagittaria pygmaea, Sagittaria trifolia, Cyperus serotinus, Eleocharis kuroguwai, Scirpus hotarui, and Alisma canaliculatum.

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Further, the compound of the invention is highly safe to useful crops and useful plants, in particular, to rice, wheat, barley, com, grain sorghum, soybean, cotton, sugar beet, etc.

Thus, the invention provides an agrochemical composition having an excellent effect as herbicides.

Description of Embodiments

The definitions of the terms used in the present Description are given below.

Halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

The descriptions like Cj-Cg indicate the number of carbon atoms in a substituent group described hereinbelow. For example, Ci-Cg means 1 to 6 carbon atoms.

The Ci-C₆ alkyl group represents, unless specified otherwise, a linear or branched alkyl group having 1 to 6 carbon atoms, and examples thereof include a group like methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl,

2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl,

2- ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl,

2.3- dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,

1-ethyl-1-methylpropyl, and l-ethyl-2-methylpropyl.

The C1-C12 alkyl group represents, unless specified otherwise, a linear or branched alkyl group having 1 to 12 carbon atoms, and examples thereof include, in addition to those exemplified above for the Ci-Cg alkyl group, a group like heptyl, 1-methylhexyl, 5-methylhexyl, 1,1-dimethylpentyl, 2,2-dimethylpentyl, 4,4-dimethylpentyl, 1-ethylpentyl, 2-ethylpentyl,

1.1.3- trimethylbutyl, 1,2,2-trimethylbutyl, 1,3,3-trimethylbutyl, 2,2,3-trimethylbutyl,

2.3.3- trimethylbutyl, 1-propylbutyl, 1,1,2,2-tetramethylpropyl, octyl, 1-methylheptyl,

3- methylheptyl, 6-methylheptyl, 2-ethylhexyl, 5,5-dimethylhexyl, 2,4,4-trimethylpentyl,

1-ethyl-1-methylpentyl, nonyl, 1-methyloctyl, 2-methyloctyl, 3-methyloctyl, 7-methyloctyl,

1-ethylheptyl, 1,1-dimethylheptyl, 6,6-dimethylheptyl, decyl, 1-methylnonyl, 2-methylnonyl, 6-methylnonyl, 1-ethyloctyl, 1-propylheptyl, n-nonyl, andn-decyl.

The C₃-Cg cycloalkyl group represents, unless specified otherwise, a cycloalkyl group

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The C3-C6 cycloalkenyl group represents, unless specified otherwise, a cycloalkenyl group having 3 to 6 carbon atoms, and examples thereof include a group like cyclopentenyl and cyclohexenyl.

The C3-C6 cycloalkyl Ci-Ce alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a cycloalkyl having 3 to 6 carbon atoms, wherein the cycloalkyl moiety and alkyl moiety have the same definitions as above, and examples thereof include a group like cyclopropylmethyl, 1-cyclopropylethyl, 2-cyclopropylethyl,

1- cyclopropylpropyl, 2-cyclopropylpropyl, 3-cyclopropylpropyl, cyclobutylmethyl, cyclopentylmethyl, and cyclohexylmethyl.

The C3-C6 cycloalkyl Ci-Cg alkyloxy group represents an (alkyl)-O- group (i.e., alkoxy group) having 1 to 6 carbon atoms substituted with a cycloalkyl having 3 to 6 carbon atoms, wherein the cycloalkyl moiety and alkyl moiety have the same definitions as above, and examples thereof include a group like cyclopropylmethoxy, 1 -cyclopropylethoxy,

2- cyclopropylethoxy, 1-cyclopropylpropoxy, 2-cyclopropylpropoxy, 3-cyclopropylpropoxy, cyclobutylmethoxy, cyclopentylmethoxy, and cyclohexylmethoxy.

The C3-C6 halocycloalkyl group represents, unless specified otherwise, a cycloalkyl group having 3 to 6 carbon atoms substituted with 1 to 5, or preferably 1 to 3 halogen atoms, wherein the cycloalkyl moiety and the halogen atom have the same definitions as above, and examples thereof include a group like 2,2-difluorocyclopropyl and 2,2-dichlorocyclopropyl.

The C3-C6 halocycloalkyl Cj-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a cycloalkyl group having 3 to 6 carbon atoms substituted with 1 to 5, or preferably 1 to 3 halogen atoms, wherein the cycloalkyl moiety, the alkyl moiety, and the halogen atom have the same definitions as above, and examples thereof include a group like 2,2-difluorocyclopropylmethyl and 2,2-dichlorocyclopropylmethyl.

The amino Cj-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an amino group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like 2-aminoethyl and 3-aminopropyl.

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The nitro Ci-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a nitro group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like nitromethyl and 2-nitroethyl.

The Ci-Cg haloalkyl group represents a linear or branched alkyl group having 1 to 6 carbon atoms substituted with a halogen atom, and examples thereof include a group like fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, bromodifluoromethyl, 2-fluoroethyl, 1-chloroethyl, 2-chloroethyl,

1- bromoethyl, 2-bromoethyl, 2,2-difluoroethyl, 1,2-dichloroethyl, 2,2-dichloroethyl,

2.2.2- trifluoroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl,

2- bromo-2-chloroethyl, 2-chloro-1,1,2,2-tetrafluoroethyl, 1 -chloro-1,2,2,2-tetrafluoroethyl,

1- chloropropyl, 2-chloropropyl, 3-chloropropyl, 2-bromopropyl, 3-bromopropyl,

2- bromo-l-methylethyl, 3-iodopropyl, 2,3-dichloropropyl, 2,3-dibromopropyl,

3.3.3- trifluoropropyl, 3,3,3-trichloropropyl, 3-bromo-3,3-difluoropropyl,

3.3- dichloro-3-fluoropropyl, 2,2,3,3-tetrafluoropropyl, l-bromo-3,3,3-trifIuoropropyl,

2.2.3.3.3- pentafluoropropyl, 2,2,2-trifluoro-1 -trifluoromethylethyl, heptafluoropropyl,

1.2.2.2- tetrafluoro-1 -trifluoromethylethyl, 2,3-dichloro-1,1,2,3,3-pentafluoropropyl,

2-chlorobutyl, 3-chlorobutyl, 4-chlorobutyl, 2-chloro-1,1-dimethylethyl, 4-bromobutyl, 3 -bromo-2-methylpropyl, 2-bromo-1,1 -dimethylethyl, 2,2-dichloro-1,1 -dimethylethyl,

2-chloro-l-chloromethyl-2-methylethyl, 4,4,4-trifluorobutyl, 3,3,3-trifluoro-l-methylpropyl,

3.3.3- trifluoro-2-methylpropyl, 2,3,4-trichlorobutyl, 2,2,2-trichloro-1,1 -dimethylethyl,

4-chloro-4,4-difluorobutyl, 4,4-dichloro-4-fluorobutyl, 4-bromo-4,4-difluorobutyl,

2.4- dibromo-4,4-difluorobutyl, 3,4-dichloro-3,4,4-trifluorobutyl, 3,3-dichloro-4,4,4-trifluorobutyl,

4- bromo-3,3,4,4-tetrafluorobutyl, 4-bromo-3 -chIoro-3,4,4-trifluorobutyl,

2.2.3.3.4.4- hexafluorobutyl, 2,2,3,4,4,4-hexafluorobutyl,

2.2.2- trifluoro-1 -methyl-1 -trifluoromethylethyl, 3,3,3 -trifluoro-2-trifluoromethylpropyl,

2.2.3.3.4.4.4- heptafluorobutyl, 2,3,3,3-tetrafluoro-2-trifluoromethylpropyl,

1.1.2.2.3.3.4.4- octafluorobutyl, nonafluorobutyl, 4-chloro-1,1,2,2,3,3,4,4-octafluorobutyl,

5- fluoropentyl, 5-chloropentyl, 5,5-difluoropentyl, 5,5-dichloropentyl, 5,5,5-trifluoropentyl, 6,6,6-trifluorohexyl, and 5,5,5,6,6,6-pentafluorohexyl.

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The C₂-Cg alkenyl group represents, unless specified otherwise, a linear or branched alkenyl group having 2 to 6 carbon atoms, and examples thereof include a group like vinyl, 1-propenyl, isopropenyl, 2-propenyl, 1-butenyl, 1-methyl-l-propenyl, 2-butenyl, 1-methyl-2-propenyl,

3-butenyl, 2-methyl-l-propenyl, 2-methyl-2-propenyl, 1,3-butadienyl, 1-pentenyl, l-ethyl-2-propenyl, 2-pentenyl, 1-methyl-1-butenyl, 3-pentenyl, l-methyl-2-butenyl, 4-pentenyl,

1- methyl-3-butenyl, 3-methyl-1-butenyl, l,2-dimethyl-2-propenyl, l,l-dimethyl-2-propenyl,

2- methyl-2-butenyl, 3-methyl-2-butenyl, 1,2-dimethyl-l -propenyl, 2-methyl-3-butenyl,

3- methyl-3-butenyl, 1,3-pentadienyl, l-vinyl-2-propenyl, 1-hexenyl, 1-propyl-2-propenyl,

2- hexenyl, 1-methyl-l-pentenyl, l-ethyl-2-butenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, l-methyl-4-pentenyl, l-ethyl-3-butenyl, l-(isobutyl)vinyl, 1 -ethyl- l-methyl-2-propenyl,

1- ethyl-2-methyl-2-propenyl, 1 -(isopropyl)-2-propenyl, 2-methyl-2-pentenyl,

3- methyl-3-pentenyl, 4-methyl-3-pentenyl, l,3-dimethyl-2-butenyl, l,l-dimethyl-3-butenyl,

3-methyl-4-pentenyl, 4-methyl-4-pentenyl, l,2-dimethyl-3-butenyl, l,3-dimethyl-3-butenyl, l,l,2-trimethyl-2-propenyl, 1, 5-hexadienyl, 1 -vinyl-3-butenyl, and 2,4-hexadienyl.

The Cz-Cg alkynyl group represents, unless specified otherwise, a linear or branched alkynyl group having 2 to 6 carbon atoms, and examples thereof include a group like ethynyl, 1-propynyl,

2- propynyl, 1-butynyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 1-pentynyl,

1- ethyl-2-propynyl, 2-pentynyl, 3-pentynyl, l-methyl-2-butynyl, 4-pentynyl, l-methyl-3-butynyl,

2- methyl-3-butynyl, 1-hexynyl, l-(n-propyl)-2-propynyl, 2-hexynyl, l-ethyl-2-butynyl,

3- hexynyl, 1-methyl-2-pentynyl, l-methyl-3-pentynyl, 4-methyl-l-pentynyl, 3-methyl-1-pentynyl, 5-hexynyl, l-ethyl-3-butynyl, 1-ethyl-l-methyl-2-propynyl, l-(isopropyl)-2-propynyl, l,l-dimethyl-2-butynyl, and 2,2-dimethyl-3-butynyl.

The C₂-C6 halolalkenyl group represents, unless specified otherwise, a linear or branched alkenyl group having 2 to 6 carbon atoms substituted with 1 to 11 halogen atoms that are the same or different from each other, and examples thereof include 2-chlorovinyl, 2-bromovinyl, 2-iodovinyl, 3-chloro-2-propenyl, 3-bromo-2-propenyl, 1-chloromethylvinyl,

2- bromo-l-methylvinyl, 1-trifluoromethylvinyl, 3,3,3-trichloro-1-propenyl,

3- bromo-3,3-difluoro-l-propenyl, 2,3,3,3-tetrachloro-l-propenyl, l-trifluoromethyl-2,2-difluorovinyl, 2-chloro-2-propenyl, 3,3-difluoro-2-propenyl,

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2.3.3- trichloro-2-propenyl, 4-bromo-3-chloro-3,4,4-trifluoro-l-butenyl,

-bromomethyl-2-propenyl, 3-chloro-2-butenyl, 4,4,4-trifluoro-2-butenyl,

4- bromo-4,4-difluoro-2-butenyl, 3-bromo-3-butenyl, 3,4,4-trifluoro-3-butenyl,

3.4.4- tribromo-3-butenyl, 3 -bromo-2-methyl-2-propenyl, 3,3 -difluoro-2-methyl-2-propenyl,

3.3.3- trifluoro-2-methylpropenyl, 3-chloro-4,4,4-trifluoro-2-butenyl,

3.3.3- trifluoro-l-methyl-l-propenyl, 3,4,4-trifluoro-l,3-butadienyl, 3,4-dibromo-l-pentenyl,

4.4- difluoro-3-methyl-3-butenyl, 3,3,4,4,5,5,5-heptafluoro-l-pentenyl, 5,5-difluoro-4-pentenyl,

4.5.5- trifluoro-4-pentenyl, 3,4,4,4-tetrafluoro-3-trifluoromethyl-l-butenyl,

4.4.4- trifluoromethyl-3-methyl-2-butenyl, 3,5,5-trifluoro-2,4-pentadienyl, 4,4,5,5,6,6,6-heptafluoro-2-hexenyl, 3,4,4,5,5.5-hexafluoro-3-trifluoromethyl-l-pentenyl,

4.5.5.5- tetrafluoro-4-trifluoromethyl-2-pentenyl, and

5- bromo-4,5,5-trifluoro-4-trifluoromethyl-2-pentenyl.

The Cz-Ce halolalkynyl group represents, unless specified otherwise, a linear or branched alkynyl group having 2 to 6 carbon atoms substituted with 1 to 9 halogen atoms that are the same or different from each other, and examples thereof include 3-chloro-2-propynyl,

3-bromo-2-propynyl, 3-iodo-2-propynyl, 3-chloro-l-propynyl, and 5-chloro-4-pentynyl.

The Ci-Cg alkoxy group represents an (alkyl)-O- group having 1 to 6 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, and hexyloxy.

The Cj-Cg haloalkoxy group represents a linear or branched alkyl-O- group having 1 to 6 carbon atoms substituted with 1 to 13 halogen atoms that are the same or different from each other, wherein the haloalkyl moiety has the same definition as above, and examples thereof include a group like chloromethoxy, difluoromethoxy, chlorodifluoromethoxy, trifluoromethoxy, and 2,2,2-trifluoroethoxy.

The Cj-Cg alkoxy Ci-Cg alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms, wherein the alkyl moiety and alkoxy moiety have the same definitions as above, and examples thereof include a group like methoxymethyl, ethoxymethyl, isopropoxymethyl, pentyloxymethyl, methoxyethyl, and butoxyethyl.

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The hydroxy Cj -Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a hydroxy group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like 2-hydroxyethyl and

3-hydroxypropyl.

The Ci-Cg alkoxy Ci-Cg alkoxy Ci-Cg alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy having 1 to 6 carbon atoms substituted with an alkoxy having 1 to 6 carbon atoms, wherein the alkyl moiety and alkoxy moiety have the same definitions as above, and examples thereof include a group like 2-(2-methoxyethoxy)ethyl and

2-(2-ethoxyethoxy)ethyl.

The phenyl Ci-Cg alkoxy Ci-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with a phenyl, wherein the alkyl moiety and alkoxy moiety have the same definitions as above, and examples thereof include a group like benzyloxymethyl and benzyloxyethyl.

The Ci-Cg haloalkoxy Ci-Cg alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with a haloalkoxy group having 1 to 6 carbon atoms, wherein the haloalkoxy moiety and alkyl moiety have the same definitions as above, and examples thereof include a group like chloromethoxymethyl, difluoromethoxymethyl, chlorodifluoromethoxymethyl, trifluoromethoxymethyl, and 2,2,2-trifluoroethoxymethyl.

The Ci-Cg haloalkoxy Ci-Cg alkoxy group represents, unless specified otherwise, an alkoxy group having 1 to 6 carbon atoms substituted with a haloalkoxy group having 1 to 6 carbon atoms, wherein the haloalkoxy moiety and alkoxy moiety have the same definitions as above, and examples thereof include a group like chloromethoxymethoxy, difluoromethoxymethoxy, chlorodifluoromethoxymethoxy, trifluoromethoxymethoxy, and 2,2,2-trifluoroethoxymethoxy.

The C3-C6 cycloalkyloxy group represents, unless specified otherwise, a (cycloalkyl)-O25 group having 3 to 6 carbon atoms, wherein the cycloalkyl moiety has the same definition as above, and examples thereof include a group like cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, and cyclohexyloxy.

The C3-C6 cycloalkyloxy Ci-Cg alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with a (cycloalkyl)-O- group having 3 to 6 carbon atoms, wherein the alkyl

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The C3-C6 cycloalkyl Cj-Cg alkyloxy Ci-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with a cycloalkyl group having 3 to 6 carbon atoms, wherein the alkyl moiety, alkoxy moiety, and cycloalkyl moiety have the same definitions as above, and examples thereof include a group like cyclopropylmethyloxymethyl, cyclobutylmethyloxymethyl, cyclopentyhnethyloxymethyl, and cyclohexylmethyloxymethyl.

The (R³¹R³²N-C=O) Ci-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a (R³¹R³²N-OC-) group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like N,N-dimethylaminocarbonylmethyl, Ν,Ν-dimethylaminocarbonylethyl, and N-methyl-N-ethylaminocarbonylmethyl.

The Ci-Cg alkoxycarbonyl Cj-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkoxycarbonyl group having 1 to 6 carbon atoms, wherein the alkoxy moiety and alkyl moiety have the same definitions as above, and examples thereof include a group like 2-methoxy-2-oxoethyl, 2-ethoxy-2-oxoethyl, and 2-tert-butoxy-2-oxoethyl.

The C]-Cg alkoxycarbonyl Ci-Cg alkoxy group represents, unless specified otherwise, an alkoxy group having 1 to 6 carbon atoms substituted with an alkoxycarbonyl group having 1 to 6 carbon atoms, wherein the alkoxy moiety and alkyl moiety have the same definitions as above, and examples thereof include a group like a 2-methoxy-2-oxoethoxy group, a 2-ethoxy-2-oxoethoxy group, and a 2-tert-butoxy-2-oxoethoxy group.

The Cj-Cg alkylcarbonyl group represents an (alkyl (having 1 to 6 carbon atoms))-C(=O)group, wherein the alkyl moiety has the same definition as above, and examples thereof include acetyl and propionyl.

The Ci-Cg alkylcarbonyl C,-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkylcarbonyl group having 1 to 6 carbon

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The Ci-C₆ alkylcarbonyloxy Ci-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an (alkyl (having 1 to 6 carbon atoms))-C(=O)O- group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like acetoxymethyl, propionyloxymethyl, isopropionyloxymethyl, and pivaloyloxymethyl.

The Ci-Cg alkylidene group represents, unless specified otherwise, a divalent alkylidene group having 1 to 6 carbon atoms, wherein a single carbon carries a divalent charge and the alkyl moiety has the same definition as above, and examples thereof include a group like a methylene group, an ethylidene group, and an isopropylidene group.

The Ci-Cg alkylidene aminooxy Ci-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with (alkylidene (having 1 to 6 carbon atoms))=N-O-, wherein the alkylidene moiety and alkyl moiety have the same definitions as above, and examples thereof include a group like methyleneaminooxymethyl, 2-(ethylidene aminooxy)ethyl, and 2-(isopropylidene aminooxy)ethyl.

The C2-C6 alkenyloxy group represents, unless specified otherwise, an (alkenyl)-O- group having 2 to 6 carbon atoms, wherein the alkenyl moiety has the same definition as above, and examples thereof include a group like 2-propenyloxy.

The C₂-C₆ alkynyloxy group represents, unless specified otherwise, an (alkynyl)-O- group having 2 to 6 carbon atoms, wherein the alkynyl moiety has the same definition as above, and examples thereof include 2-propynyloxy.

The phenyloxy Ci-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a (phenyl)-O- group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like phenoxymethyl, 2-phenoxyethyl, and 3-phenoxypropyl.

The phenylthio Ci-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a (phenyl)-S- group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like phenylthiomethyl,

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2- phenylthioethyl, and 3-phenylthiopropyl.

The phenylsulfinyl Cj-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a (phenyl)-SO- group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like phenylsulfinylmethyl,

2-phenylsulfinylethyl, and 3-phenylsulfinylpropyl.

The phenylsulfonyl Ci-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a (phenyl)-SC>2- group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like 2-phenylsulfonylethyl,

3- phenylsulfonylpropyl, and 4-phenylsulfonylbutyl.

The Ci-Cg alkoxyimino group represents, unless specified otherwise, an (alkoxy)-N= group having 1 to 6 carbon atoms, wherein the alkoxy moiety has the same definition as above, and examples thereof include methoxyimino and ethoxyimino.

The Ci-Cg alkoxyimino Ci-Cg alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an alkoxyimino group having 1 to 6 carbon atoms, wherein the alkoxyimino moiety and alkyl moiety have the same definitions as above, and examples thereof include methoxyiminomethyl and ethoxyiminomethyl.

The phenoxyimino group represents, unless specified otherwise, a (substituted) (phenoxy)-N= group, and examples thereof include phenoxyimino.

The phenoxyimino Ci-Cg alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with a phenoxyimino group, wherein the phenoxyimino moiety and alkyl moiety have the same definitions as above, and examples thereof include phenoxyiminomethyl.

The di(Ci-Cg alkoxy) Cj-Cg alkyl group represents an alkyl group having 1 to 6 carbon atoms di-substituted with an alkoxy group having 1 to 6 carbon atoms, and examples thereof include (2,2-dimethoxy)ethyl, (3,3-dimethoxy)propyl, (2,2-diethoxy)ethyl group, and a (3,3-diethoxy )propyl.

The formyl Ci-Cg alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with a formyl group, wherein the alkyl moiety has the same definition as above, and examples thereof include (2-formyl)ethyl and (3-foimyl)propyL

The Ci-Cg alkylthio group represents an (alkyl)-S- group having 1 to 6 carbon atoms,

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The Ci-Cio alkylthio group represents an (alkyl)-S- group having 1 to 10 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include, in addition to those exemplified above for the Ci-Cg alkylthio group, n-heptylthio, n-octylthio, n-nonylthio, and n-decylthio.

The Ci-Cg alkylsulfinyl group represents an (alkyl)-SO- group having 1 to 6 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, and isopropylsulfinyl.

The Ci-Cio alkylsulfinyl group represents an (alkyl)-S- group having 1 to 10 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include, in addition to those exemplified above for the Ci-Cg alkylsulfinyl group, n-heptylsulfinyl, n-octylsulfinyl, n-nonylsulfinyl, and n-decylsulfinyl.

The Ci-Cs alkylsulfonyl group represents an (alkyl)-SC>2- group having 1 to 6 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, and isopropylsulfonyl.

The Ci-Cio alkylsulfonyl group represents an (alkyl)-SC>2- group having 1 to 10 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include, in addition to those exemplified above for the Ci-Cg alkylsulfonyl group, n-heptylsulfonyl, n-octylsulfonyl, n-nonylsulfonyl, and n-decylsulfonyl.

The Ci-Cg alkenylthio group represents an (alkenyl)-S- group having 2 to 6 carbon atoms, wherein the alkenyl moiety has the same definition as above, and examples thereof include a group like allylthio.

The C2-C6 alkenylsulfinyl group represents an (alkenyl)-SO- group having 3 to 6 carbon atoms, wherein the alkenyl moiety has the same definition as above, and examples thereof include a group like allylsulfinyl.

The C2-C6 alkenylsulfonyl group represents an (alkenyl)-SO2- group having 2 to 6 carbon atoms, wherein the alkenyl moiety has the same definition as above, and examples thereof include a group like allylsulfonyl.

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The C₂-Cg alkynylthio group represents an (alkynyl)-S- group having 2 to 6 carbon atoms, wherein the alkynyl moiety has the same definition as above, and examples thereof include a group like 2-propynylthio.

The Ci-Cg alkynylsulfinyl group represents an (alkynyl)-SO- group having 2 to 6 carbon atoms, wherein the alkynyl moiety has the same definition as above, and examples thereof include a group like 2-propynylsulfinyl.

The C2-C6 alkenylsulfonyl group represents an (alkynyl)-SO₂- group having 2 to 6 carbon atoms, wherein the alkynyl moiety has the same definition as above, and examples thereof include a group like 2-propynylsulfonyl.

The C1-C10 alkylsulfonyloxy group represents an (alkyl)SO2-O- group having 1 to 10 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include methylsulfonyloxy and ethylsulfonyloxy.

The Ci-Cg alkylthio Cj-Cg alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an alkylthio group having 1 to 6 carbon atoms, wherein the alkyl moiety and alkylthio moiety have the same definitions as above, and examples thereof include methylthiomethyl and ethylthiomethyl.

The Ci-Q alkylsulfinyl Cj-Cg alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an alkylsulfinyl group having 1 to 6 carbon atoms, wherein the alky] moiety and alkylsulfinyl moiety have the same definitions as above, and examples thereof include methylsulfinylmethyl and ethylsulfinylmethyl.

The Cj-Cg alkylsulfonyl Cj-Cg alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an alkylsulfonyl group having 1 to 6 carbon atoms, wherein the alkyl moiety and alkylsulfonyl moiety have the same definitions as above, and examples thereof include methylsulfonylmethyl and ethylsulfonylmethyl.

The Ci-Cg alkoxy Ci-Cg alkoxy group represents an alkoxy group having 1 to 6 carbon atoms substituted with an alkoxy having 1 to 6 carbon atoms, wherein the alkoxy moiety has the same definition as above, and examples thereof include a group like methoxymethoxy, ethoxymethoxy, 2-methoxyethoxy, and 2-ethoxyethoxy.

The Cj-Cg haloalkylthio Ci-Cg alkyl group represents, unless specified otherwise, an alkyl

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The Ci-Cg haloalkylsulfinyl Ci-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a (haloalkyl)-SO- group having 1 to 6 carbon atoms, wherein the alkyl moiety and haloalkyl moiety have the same definitions as above, and examples thereof include a group like difluoromethylsulfinylmethyl and trifhioromethylsulfinylrnethyl.

The Ci-Cg haloalkylsulfonyl Ci-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a (haloalkyl)-SO2- group having 1 to 6 carbon atoms, wherein the alkyl moiety and haloalkyl moiety have the same definitions as above, and examples thereof include a group like difluoromethylsulfonylmethyl and trifluoromethylsulfonylmethyl.

The Cj-Cg alkylthio Ci-Cg alkoxy Cj-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with an alkylthio group having 1 to 6 carbon atoms, wherein the alkylthio moiety, alkoxy moiety, and alkyl moiety have the same definitions as above, and examples thereof include a group like 2-methylthioethoxymethyl and 2-ethylthioethoxymethyl.

The Ci-Cg alkylsulfinyl Ci-Cg alkoxy Cj-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with an alkynylsulfinyl group having 1 to 6 carbon atoms, wherein the alkynylsulfinyl moiety, alkoxy moiety, and alkyl moiety have the same definitions as above, and examples thereof include a group like 2-methylsulfinyl ethoxymethyl and 2-ethylsulfinyl ethoxymethyl.

The Ci-Cg alkylsulfonyl Ci-Cg alkoxy Ci-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with an alkynylsulfonyl group having 1 to 6 carbon atoms, wherein the alkylsulfonyl moiety, alkoxy moiety, and alkyl moiety have the same definitions as above, and examples thereof include a group like 2-methylsulfonylethoxymethyl and

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2- ethylsulfbnylethoxymethyl.

The Ci-Ce acyl group represents an acyl group derived from Cj-Ce carboxylic acid, and examples thereof include an acetyl group and a propionyl group.

The Ci-Ce alkylcarbonyl group represents an (alkyl (having 1 to 6 carbon atoms))-C(=O)group, wherein the alkyl moiety has the same definition as above, and examples thereof include an acetyl group and a propionyl group.

The Ci-Cg alkylcarbonyloxy group represents an (alkyl (having 1 to 6 carbon atoms))-C(=O)-O- group, wherein the alkyl moiety has the same definition as above, and examples thereof include acetoxy and propionyloxy.

The Ci-Ce haloalkylcarbonyloxy group represents a (haloalkyl (having 1 to 6 carbon atoms))-C(=O)-O- group, wherein the haloalkyl moiety has the same definition as above, and examples thereof include a group like chloromethylcarbonyloxy, difluoromethylcarbonyloxy, chlorodifluoromethylcarbonyloxy, trifluoromethylcarbonyloxy, and 2,2,2-trifluoroethylcarbonyloxy.

The C2-C6 alkenylcarbonyloxy group represents an (alkenyl (having 2 to 6 carbon atoms))-C(=O)-O- group, wherein the alkenyl moiety has the same definition as above, and examples thereof include a group like 1-propenylcarbonyloxy, 2-propenylcarbonyloxy, 1-butenylcarbonyloxy, and 1-methyl-1-propenylcarbonyloxy.

The C2-C6 halolalkenylcarbonyloxy group represents a (haloalkenyl (having 2 to 6 carbon atoms))-C(=O)-O- group, wherein the haloalkenyl moiety has the same definition as above, and examples thereof include a group like 3-chloro-2-propenylcarbonyloxy and

3- bromo-2-propenylcarbonyloxy.

The C2-C6 alkynylcarbonyloxy group represents an (alkynyl (having 2 to 6 carbon atoms))-C(=O)-O- group, wherein the alkynyl moiety has the same definition as above, and examples thereof include a group like 1-propynylcarbonyloxy and 2-propynylcarbonyloxy.

The C2-C6 haloalkynylcarbonyloxy group represents a (haloalkynyl (having 2 to 6 carbon atoms))-C(=O)-O- group, wherein the haloalkynyl moiety has the same definition as above, and examples thereof include a group like 3-chloro-1 -propynylcarbonyloxy and

3,3,3 -trifluoro-1 -propynylcarbonyloxy.

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The C₂-C6 alkylidene amino group represents an alkyl (having 1 to 5 carbon atoms)-CH=Ngroup, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like ethylideneamino and propylideneamino.

The di(Ci-Cio alkyl)amino Ci-Cg alkylidene amino group represents an amino group substituted with an alkylidene group having 1 to 6 carbon atoms substituted with an amino group di-substituted with an alkyl group having 1 to 10 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like a dimethylamino methylidene amino group and a diethylamino methylidene amino group.

The Ci-Cio alkylamino group represents an (alkyl)-NH- group having 1 to 10 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include methylamino and ethylamino.

The di(Ci-Cio alkyl)amino group represents an (alkyl)₂N- group, wherein the alkyl moiety has the same definition as above, and examples thereof include dimethylamino, diethylamino, methylethylamino, dipropylamino, and dibutylamino.

The mono(Ci-C6 alkyl)amino group represents an (alkyl)-NH- group having 1 to 6 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like methylamino and ethylamino.

The di(Ci-C6 alkyl)amino group represents an (alkyl (having 1 to 6 carbon atoms))₂N- group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group 20 like dimethylamino, diethylamino, methylethylamino, dipropylamino, and dibutylamino.

The Ci-Ce alkylamino Ci-Cg alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an alkylamino group having 1 to 6 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include N-methylaminomethyl and N-methylaminoethyl.

The di(Ci-C6 alkyl)amino Ci-Cg alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an (alkyl (having 1 to 6 carbon atoms))₂N- group, wherein the alkyl moiety has the same definition as above, and examples thereof include Ν,Ν-dimethylaminomethyl and N,N-dimethylaminoethyl.

The Ci-Ce alkoxycarbonyl amino group represents an amino group substituted with an

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The Ci-Cg alkylcarbonyl amino group represents, unless specified otherwise, an amino group substituted with an alkylacarbonyl group having 1 to 6 carbon atoms, wherein the alkylcarbonyl moiety has the same definition as above, and examples thereof include a group like formamide, acetamide, and propionamide.

The Ci-Cg alkoxycarbonyl group represents an (alkyl (having 1 to 6 carbon atoms))-O-C(=O)- group, wherein the alkyl moiety has the same definition as above, and examples thereof include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, and isopropoxycarbonyl.

The Ci-Cio alkylthiocarbonyl group represents an (alkyl (having 1 to 10 carbon atoms))-S-C(=O)- group, wherein the alkyl moiety has the same definition as above, and examples thereof include methylthiocarbonyl and ethylthiocarbonyl.

The CpCg alkoxycarbonyloxy group represents an oxy group substituted with an (alkoxy (having 1 to 6 carbon atoms))-C(=O)- group, wherein the alkoxycarbonyl moiety has the same definition as above, and examples thereof include methoxycarbonyloxy and ethoxycarbonyloxy.

The Ci-Cg haloalkylcarbonyl group represents a (haloalkyl (having 1 to 6 carbon atoms))-C(=O)- group, wherein the haloalkyl moiety has the same definition as above, and examples thereof include chloroacetyl, trifluoroacetyl, pentafluoropropionyl, and difluoromethylthio.

The Cj-Cg haloalkylthio group represents a (haloalkyl (having 1 to 6 carbon atoms))-Sgroup, wherein the haloalkyl moiety has the same definition as above, and examples thereof include difluoromethylthio and trifluoromethylthio.

The Ci-Cg haloalkylsulfmyl group represents a (haloalkyl (having 1 to 6 carbon atoms))-SOgroup, wherein the haloalkyl moiety has the same definition as above, and examples thereof include trifluoromethylsulfinyl and difluoromethylsulfinyl.

The Ci-Cs haloalkylsulfonyl group represents a (haloalkyl (having 1 to 6 carbon atoms))-SC>2- group, wherein the haloalkyl moiety has the same definition as above, and

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PCT/JP2011/062643 examples thereof include chloromethylsulfonyl, difluoromethylsulfonyl, and trifluoromethylsulfonyl.

The Ci-Cg haloalkylsulfonyloxy group represents a (haloalkyl (having 1 to 6 carbon atoms))-SO2-O- group, wherein the haloalkyl moiety has the same definition as above, and examples thereof include chloromethylsulfonyloxy and trifluoromethylsulfonyloxy.

The mono(Ci-Cfi alkyl)aminocarbonyl group represents an (alkyl (having 1 to 6 carbon atoms))-NH-C(=O)- group, wherein the alkyl moiety has the same definition as above, and examples thereof include methylaminocarbonyl and ethylaminocarbonyl.

The di(C]-Cg alkyl)aminocarbonyl group represents an (alkyl (having 1 to 6 carbon atoms))2N-C(=O)- group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like dimethylaminocarbonyl, diethylaminocarbonyl, methylethylaminocarbonyl, dipropylaminocarbonyl, and dibutylaminocarbonyl.

The cyano Ci-Cg alkyl group represents a cyano alkyl group having 1 to 6 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include cyanomethyl and cyanoethyl.

The cyano Ci-Cg alkoxy group represents an alkoxy group having 1 to 6 carbon atoms substituted with a cyano group, wherein the alkoxy moiety has the same definition as above, and examples thereof include a group like 2-cyanoethoxy and 3-cyanopropoxy.

The cyano Ci-Cg alkoxy Ci-Cg alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with a cyano group, wherein the alkoxy moiety and alkyl moiety have the same definitions as above, and examples thereof include a group like 2-cyanoethoxymethyl and 3-cyanopropoxymethyl.

The phenyl Ci-Cg alkyl group represents an alkyl group having 2 to 6 carbon atoms substituted with a phenyl group, wherein the alkyl moiety has the same definition as above, and examples thereof include benzyl, phenethyl, and phenylpropyl.

The phenyl C₂-C6 alkenyl group represents an alkenyl group having 2 to 6 carbon atoms substituted with a phenyl group, wherein the alkenyl moiety has the same definition as above, and examples thereof include styryl and cinnamyl.

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The phenyl C₂-Ce alkynyl group represents an alkynyl group having 2 to 6 carbon atoms substituted with a phenyl group, wherein the alkynyl moiety has the same definition as above, and examples thereof include (2-phenyl)ethynyl and 2-(3-phenyl)ethynyl.

The phenylcarbonyloxy group represents a (phenyl)-C(=O)-O- group and examples thereof include a phenylcarbonyloxy group.

The phenylcarbonyl Ci-Cg alkyloxy group represents an alkoxy group having 1 to 6 carbon atoms substituted with a (phenyl)-C(=O)group and examples thereof include phenylcarbonylmethoxy.

The phenylthio group represents a phenyl-S- group.

The phenylsulfinyl group represents a phenyl-SO- group.

The phenylsulfonyl group represents a phenyl-SO₂- group.

The phenylsulfonyloxy group represents a phenyl-SO₂-O- group.

The benzylthio group represents a benzyl-S- group.

The benzylsulfinyl group represents a benzyl-SO- group.

The benzylsulfonyl group represents a benzyl-SO₂- group.

The benzylsulfonyloxy group represents a benzyl-SCh-O- group.

As a group constituting a C3-C6 alkylene group, 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting a carbonyl group, and the C₃-Ce alkylene group is a linear or branched divalent alkylene group having 3 to 6 carbon atoms, and 1 to 3 carbon atoms in the alkylene group may be substituted with an atom or a group of atoms selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting a carbonyl group, and examples thereof include a trimethylene group, a propylene group, a butylene group, a methylenedioxy group, and an ethylenedioxy group. Preferred examples of the alkylene group include a C1-C3 alkylenedioxy group.

Examples of the heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom include furan, thiophene, pyrrole, pyrazole, imidazole, pyridine, pyrimidine, pyrazine, pyridazine, pyrrolidine, piperidine, piperazine, morpholine, thiomorpholine,

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2018201082 14 Feb 2018 benzofuran, benzothiophene, indole, benzoxazole, benzothiazole, benzimidazole, isoxazole, isoxazoline, oxazole, oxazoline, isothiazole, isothiazoline, thiazole, thetrahydrofuran, and thiazoline. Preferred examples of the heterocyclic group include pyridine, pyrimidine, pyrazine, thiophene, pyrazole, isoxazole, morpholine, thiomorpholine (sulfur atom of thiomorpholine may 5 be bonded with one or two oxygen atoms), piperidine, pyridazine, piperazine, and tetrahydrofuran.

More preferred examples of the heterocyclic group include pyridine, pyrimidine, pyrazine, thiophene, pyrazole, isoxazole, morpholine, thiomorpholine (sulfur atom of thiomorpholine may be bonded with one or two oxygen atoms), and piperidine.

The heterocyclic oxy group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and optionally selected from an oxygen atom, a sulfur atom, and a nitrogen atom represents, unless specified otherwise, a group in which the oxygen atom is substituted with a heterocycle having the same definition as above, and examples thereof include (tetrahydrofuran-2-yl)oxy, (4,5-dihydroisoxazol-5-yl)oxy, (isoxazol-5-yl)oxy, and a (thiophen-2-yl)oxy group.

The Ci-Cg alkyl group substituted with a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom represents an alkyl group having 1 to 6 carbon atoms substituted with a heterocycle wherein the alkyl moiety and heterocyclic moiety have the same definitions as above, and examples thereof include (2-furan)methyl, (3-furan)methyl, (2-thiophene)methyl, and (3-thiophene)methyl.

The Ci-Ce alkyl group substituted with a heterocyclic oxy group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom represents an alkyl group having 1 to 6 carbon atoms substituted with a heterocyclic oxy group wherein the alkyl moiety and heterocyclic 25 moiety have the same definitions as above, and examples thereof include (tetrahydrofuran-2-yl)oxymethyl, (4,5-dihydroisoxazol-5-yl)oxymethyl, (isoxazol-5-yl)oxymethyl, and (thiophen-2-yl)oxymethyl.

The Ci-Ce alkoxy Ci-Ce alkyl group substituted with a heterocyclic oxy group having 3 to carbon atoms and one or more heteroatoms that are the same or different from each other and

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PCT/JP2011/062643 selected from an oxygen atom, a sulfur atom, and a nitrogen atom represents an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with a heterocyclic oxy group wherein the alkyl moiety, alkoxy moiety, and heterocyclic moiety have the same definitions as above, and examples thereof include (tetrahydrofuran-2-yl)oxymethoxymethyl, (4,5-dihydroisoxazol-5 -yl)oxyethoxymethyl, (isoxazol-5-yl)oxymethoxymethyl, and (thiophen-2-yl)oxyethoxymethyl.

The Ci-C₆ alkoxy Ci-Cg alkyl group substituted with a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom represents an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with a heterocyclic group wherein the alkyl moiety, alkoxy moiety, and heterocyclic moiety have the same definitions as above, and examples thereof include tetrahydrofurfuryloxyethyl and tetrahydrofurfuryloxymethyl.

The Ci-C₆ alkoxy group substituted with a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom represents an alkoxy group having 1 to 6 carbon atoms substituted with a heterocyclic group wherein the heterocyclic moiety and alkoxy moiety have the same definitions as above, and examples thereof include a 6-methyl-2-pyridinemethoxy group and a tetrahydrofurfuryloxy group.

Alkali metal includes sodium, potassium, and the like.

Next, specific examples of the compound of the invention represented by Formula 1 are described in Table 1 to Table 43. However, the invention is not limited to those compounds.

In the present Description, the following descriptions included in the tables indicate the corresponding group, respectively, as shown below.

For example, Me represents a methyl group, Et represents an ethyl group, Pr-n represents a n-propyl group, Pr-i represents an isopropyl group, Pr-c represents a cyclopropyl group, Bu-n represents a n-butyl group, Bu-s represents a secondary butyl group, Bu-i represents an isobutyl group, Bu-t represents a tertiary butyl group, Bu-c represents a cyclobutyl group, Pen-n represents a n-pentyl group, Pen-c represents a cyclopentyl group, Hex-n represents a n-hexyl group, Hex-c

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2018201082 14 Feb 2018 represents a cyclohexyl group, Ac represents an acetyl group, Ph represents a phenyl group, Bn represents a benzyl group, Ts represents a p-toluene sulfonyl group, pyridyl represents a pyridyl group, and pyrimidinyl represents a pyrimidinyl group. Further, Ph(2-OMe) represents a 2-methoxyphenyl group, CH2Ph(2-OMe) represents a 2-methoxybenzyl group, and Ph(3,4-C12) 5 represents a 3,4-dichlorophenyl group.

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2018201082 14 Feb 2018 [Table 1]

	R⁴	O Ο ¹	Y An'^r1 N 'Z R²
Compound No.	R¹	R²	Y	z	R⁴
I-l	Me			Me	O	0	OH
1-2	Et			Me	0	0	OH
1-3	Pr-n			Me	0	0	OH
1-4	Pr-i			Me	0	0	OH
1-5	Bu-n			Me	0	0	OH
1-6	Bu-i			Me	0	0	OH
1-7	Bu's			Me	0	0	OH
1-8	Bu-t			Me	0	0	OH
1-9	Hex-n			Me	0	0	OH
1-10	CH₂CF₃			Me	0	0	OH
Ill	CH₂CH=CH₂			Me	0	0	OH
1-12	CH₂C(Me>CH₂			Me	0	0	OH
1-13	CH₂CH₂CH=CMe₂			Me	0	0	OH
1-14	ch₂c=ch			Me	0	0	OH
1-15	ch₂c=cch₃			Me	0	0	OH
1-16	Pr-c			Me	0	0	OH
1-17	Bu-c			Me	0	0	OH
1-18	Pen'c			Me	0	0	OH
1-19	Hex-c			Me	0	0	OH
1-20	CH₂Pr-c			Me	0	0	OH
1-21	CH2BU-C			Me	0	0	OH
1-22	CHsPen-c			Me	0	0	OH
1-23	CH₂Hex-c			Me	0	0	OH
1-24	CH₂CH=CC1₂			Me	0	0	OH
1-25	CH₂CC1=CHC1			Me	0	0	OH
1-26	ch₂ch₂ch=cci₂			Me	0	0	OH
1-27	CH₂CH₂C(Me)=CF₂			Me	0	0	OH
1-28	CH₂CH₂CH₂CH₂C(Me)=CF₂			Me	0	0	OH
1-29	CH₂CH=CF₂			Me	0	0	OH
1-30	CH₂CH₂OMe			Me	0	0	OH
1-31	CH₂CH₂OEt			Me	0	0	OH
1-32	CH(Me)CH₂OMe			Me	0	0	OH
1-33	CH₂CH₂OCH₂CH₂OMe			Me	0	0	OH
1-34	CH₂CH₂OPr-n			Me	0	0	OH
1-35	CH₂CH₂OPr-i			Me	0 '	0	OH
1-36	CH₂CH₂OPr-c			Me	0	0	OH
1-37	CH₂CH₂OBu-c			Me	0	0	OH
1-38	CH₂CH₂OPen-c			Me	0	0	OH
1-39	CH₂CH₂OHex-c			Me	0	0	OH
1-40	CH₂CH₂OCH₂CF₃			Me	0	0	OH
1-41	CH₂CH₂CH₂OMe			Me	0	0	OH

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Compound No.	R¹	R²	Y	z	R⁴
1-42	CH=CHMe	Me	0	o	OH
143	CHzSMe	Me	0	0	OH
1-44	CH₂SPr-n	Me	o	0	OH
1-45	CH₂CH₂SMe	Me	0	0	OH
1-46	CH₂SOMe	Me	0	0	OH
1-47	CHgSOjMe	Me	0	0	OH
1-48	CH₂CH₂CH₂SMe	Me	0	0	OH
1-49	CH₂CH₂CH₂SO2Me	Me	0	0	OH
1-50	Ph	Me	0	o	OH
1-51	Ph(2-CD	Me	0	0	OH
1-52	Ph(3-CD	Me	0	o	OH
1-53	Ph(4-Cl)	Me	0	o	OH
1-54	Ph(2-F)	Me	0	o	OH
1-55	Ph(3-F)	Me	0	0	OH
1-56	Ph(4-F)	Me	0	0	OH
1-57	Ph(2-Me)	Me	0	o	OH
1-58	Ph(3-Me)	Me	0	o	OH
1-59	Ph(4-Me)	Me	0	o	OH
1-60	Ph(2-OMe)	Me	0	o	OH
1-61	Ph(3-OMe)	Me	0	0	OH
1-62	Ph(4-OMe)	Me	0	o	OH
1-63	Ph(2-CFs)	Me	0	0	OH
1-64	Ph(3-CFs)	Me	0	o	OH
1-65	Ph(4-CFs)	Me	0	0	OH
1-66	Ph(2-NOa)	Me	0	0	OH
1-67	Phte-NOj	Me	0	o	OH
1-68	PhU-NOz)	Me	0	0	OH
1-69	Ph(2-OCFs)	Me	0	o	OH
1-70	PhO-OCFg)	Me	0	0	OH
1-71	Ph(4OCFa)	Me	0	0	OH
1-72	Ph(2-CN)	Me	0	o	OH
1-73	Ph(3-CN)	Me	0	o	OH
1-74	Ph(4-CN)	Me	0	o	OH
1-75	Ph(3,4F2)	Me	0	0	OH
1-76	Ph(3,5-F₂)	Me	0	0	OH
1-77	Ph(2,3Fi)	Me	0	0	OH
1-78	Ph(2,4F2)	Me	0	0	OH
1-79	Ph(2,5F2)	Me	0	0	OH
1-80	Ph(2,6F₂)	Me	0	0	OH
1-81	Ph(3,4-Cls)	Me	0	0	OH
1-82	Ph(3,5C12)	Me	0	0	OH
1-83	Ph(2,3Cl₂)	Me	0	0	OH
1-84	Ph(2,4C12)	Me	0	0	OH
1-85	Ph(2,5C12)	Me	0	0	OH

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2018201082 14 Feb 2018 [Table 3]

Compound No.	R¹	R²	Y	z	R⁴
1-86	Ph(2,6-C12)	Me	0	0	OH
1-87	Ph(3,4-Me2)	Me	0	0	OH
1-88	Ph(3,5-Me2)	Me	0	0	OH
1-89	Ph(2,3-Me2)	Me	0	0	OH
1-90	Ph(2,4-Mez)	Me	0	0	OH
1-91	Ph(2,5-Me₂)	Me	0	0	OH
1-92	Ph(2,6-Me₂)	Me	0	0	OH
1-93	Ph(3,4-OMe2)	Me	0	0	OH
1-94	Ph(3,5-OMe2)	Me	0	0	OH
1-95	Ph(2,3-OM_e2)	Me	0	0	OH
1-96	Ph(2,4-OMe2)	Me	0	o	OH
1-97	Ph(2,5-OM_e2)	Me	0	0	OH
1-98	Ph(2,6-OM_e2)	Me	0	0	OH
1-99	Ph(3-F-4-OMe)	Me	0	0	OH
1-100	Ph(3-F-5-OMe)	Me	0	0	OH
1-101	Ph(2-F-3-OMe)	Me	0	0	OH
1-102	Ph(2-F-4-OMe)	Me	0	0	OH
1-103	Ph(2-F-5-OMe)	Me	0	0	OH
1-104	Ph(2-F-6-OMe)	Me	0	0	OH
1-105	Ph(3-F-4-Me)	Me	0	0	OH
1-106	Ph(3-F-5-Me)	Me	0	0	OH
1-107	Ph(2-F-3-Me)	Me	0	o	OH
1-108	Ph(2-F-4-Me)	Me	0	0	OH
1-109	Ph(2-F-5Me)	Me	0	0	OH
I-110	Ph(2-F-6-Me)	Me	0	o	OH
1-111	Ph(3-OMe-4-F)	Me	0	o	OH
1-112	Ph(2-OMe-3-F)	Me	0	o	OH
1-113	Ph(2-OMe-4-F)	Me	0	o	OH
1-114	Ph(2-OMe5F)	Me	0	0	OH
1-115	Ph(3-Me-4-F)	Me	0	0	OH
1-116	Ph(2-Me-3-F)	Me	0	0	OH
1-117	Ph(2-Me-4-F)	Me	0	0	OH
1-118	Ph(2-Me-5-F)	Me	0	0	OH
1119	Ph(3-Cl-4OMe)	Me	0	0	OH
1-120	Ph(3-Cl-5-OMe)	Me	0	o	OH
1-121	Ph(2-Cl-3-OMe)	Me	0	0	OH
1-122	Ph(2-Cl-4-OMe)	Me	0	0	OH
1-123	Ph(2-Cl-5-OMe)	Me	0	0	OH
1-124	Ph(2-Cl-6-OMe)	Me	0	0	OH
1-125	Ph(3-Cl-4-Me)	Me	0	0	OH
1-126	Ph(3-Cl-5-Me)	Me	0	0	OH
1-127	Ph(2-Cl-3-Me)	Me	0	0	OH
1-128	Ph(2-Cl-4-Me)	Me	0	0	OH
IT29	Ph(2-Cl-5-Me)	Me	0	0	OH

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Compound No.	K¹	R²	Y	z	R⁴
1-130	Ph(2-Cl-6-Me)	Me	0	0	OH
1-131	Ph(3-OMe-4-Cl)	Me	0	0	OH
1-132	Ph(2-OMe-3-Cl)	Me	0	0	OH
1-133	Ph(2-OMe-4-Cl)	Me	0	0	OH
1-134	Ph(2-OMe-5-Cl)	Me	0	0	OH
1-135	Ph(3-Me-4-CD	Me	0	0	OH
1136	Ph(2-Me-3-Cl)	Me	0	0	OH
1-137	Ph(2-Me-4-Cl)	Me	0	o	OH
1-138	Ph(2-Me-5-Cl)	Me	0	0	OH
1-139	Ph(3-F-4-Cl)	Me	0	o	OH
1-140	Ph(3-F-5-Cl)	Me	0	0	OH
1-141	Ph(2-F-3-Cl)	Me	0	0	OH
1-142	Ph(2-F-4-Cl)	Me	0	o	OH
1-143	Ph(2-F-5-Cl)	Me	0	o	OH
1-144	Ph(2-F-6-CD	Me	0	0	OH
1-145	Ph(3-Cl-4F)	Me	0	0	OH
1-146	Ph(2-Cl-3-F)	Me	0	0	OH
1-147	Ph(2-Cl-4-F)	Me	0	0	OH
1-148	Ph(2-Cl-5-F)	Me	0	0	OH
1-149	Ph(3-Me-4-OMe)	Me	0	0	OH
IT50	Ph(3Me-5OMe)	Me	0	0	OH
1-151	Ph(2-Me-3-OMe)	Me	0	0	OH
1-152	Ph(2-Me-4OMe)	Me	0	0	OH
1-153	Ph(2-Me-5OMe)	Me	0	o	OH
1-154	Ph(2-Me-6-OMe)	Me	0	0	OH
IT55	Ph(3OMe-4Me)	Me	0	0	OH
1-156	Ph(2-OMe-3-Me)	Me	0	0	OH
1-157	Ph(2-OMe-4-Me)	Me	0	0	OH
1-158	Ph(2-OMe-5-Me)	Me	0	0	OH
1-159	Ph(3-CN-4OMe)	Me	0	0	OH
1-160	Ph(3OMe-4-CN)	Me	0	0	OH
1-161	Ph(3-Me-4-CN)	Me	0	0	OH
1-162	Ph(3-CN-4-Me)	Me	0	0	OH
1-163	Ph(3-NO₂-4-OMe)	Me	0	0	OH
1-164	Ph(3-OMe-4-NO2)	Me	0	0	OH
1-165	Ph(3-Me-4-NO2)	Me	0	0	OH
1-166	Ph(3-NO₂-4-Me)	Me	0	0	OH
1-167	Ph(3,5-F₂-4-OMe)	Me	0	0	OH
1-168	Ph(3,5-F₂-4-Me)	Me	0	0	OH
1-169	ΡΗ3,4,5-(ΟΜβ)3)	Me	0	0	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 5]

Compound No.	R¹	R²	Y	z	R⁴ .
1-170	-Q-o o	Me	0	0	OH
1-171	~^^3	Me	0	0	OH
1-172		Me	0	0	OH
1-173	-	Me	0	0	OH
1-174		Me	0	o	OH
1-175		Me	0	0	OH
1-176		Me	0	o	OH
1-177		Me	0	0	OH
1178	Me ^υ	Me	0	0	OH
1-179		Me	0	o	OH
1-180		Me	0	0	OH
1-181	~Gⁿ	Me	0	0	OH
1-182	^CyMe	Me	0	0	OH
1-183	——OMe	Me	0	0	OH
1-184		Me	0	0	OH

WO 2012/002096

PCT/JP2011/062643 [Table 6]

Compound No.	R^l	R²	Y	z	R⁴
1-185		Me	0	0	OH
1-186	~Ν-^^ΒΓ	Me	0	0	OH
1-187	— N—	Me	0	0	OH
1-188	V¹·	Me	0	0	OH
1-189	_^Me	Me	0	0	OH
1-190		Me	0	0	OH

1-191		Me	0	0	OH
1-192		Me	0	0	OH

1-193	~v°	Me	0	0	OH
1-194	N	Me	0	0	OH
	S~^-Me
1-195	—4 J N	Me	0	o	OH

1196	—1 N Me	Me	0	o	OH
1-197	a -Me AX N Me	Me	0	0	OH
1-198		Me	0	0	OH
I 199		Me	0	0	OH
	Me
1-200	AT	Me	0	0	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 7]

Compound No.	R¹	R²	Y	z	R⁴
1-201	-<L U^'Me	Me	0	0	OH
1-202	-f(2)⁰	Me	0	0	OH
1-203		Me	0	0	OH
1-204	-nQsO₂	Me	0	0	OH
1-205	CH₂Ph	Me	0	0	OH
1-206	CH₂CH₂Ph	Me	0	0	OH
1-207	CHsCHjCHoPh	Me	0	0	OH
1-208	CH₂CH=CHPh	Me	0	0	OH
1-209	CH₂C=CPh	Me	0	0	OH
1-210	CH₂CH=NOMe	Me	0	0	OH
1-211	CH₂CH=N0Et	Me	0	0	OH
1-212	CH₂CH=NOPr-n	Me	0	0	OH
1-213	CH₂CH=NOPh	Me	0	0	OH
1-214	CH₂CH(OMe)₂	Me	0	0	OH
1-215	CH₂CHO	Me .	0	0	OH
1-216	nh₂	Me	0	0	OH
1-217	NHMe	Me	0	0	OH
1-218	NHEt	Me	0	0	OH
1-219	NHPr-n	Me	0	0	OH
1-220	NHPr-i	Me	0	0	OH
1-221	NHBu-n	Me	0	0	OH
1-222	NHBu-i	Me	0	0	OH
1-223	NHBu'8	Me	0	0	OH
1-224	NHCH₂Pr-c	Me	0	0	OH
1-225	NHPeirn	Me	0	0	OH
1-226	NHHex*n	Me	0	0	OH
1-227	NHCH2CH2CH2C1	Me	0	0	OH
1-228	NHCH2CH2CH2F	Me	0	0	OH
1-229	NHCH₂CH₂OMe	Me	0	0	OH
1-230	NMeo	Me	0	0	OH
1-231	NEts	Me	0	0	OH
1-232	N(Pr-n)₂	Me	0	0	OH
1-233	N(Bu-n)₂	Me	0	0	OH
1-234	N(Me)Et	Me	0	0	OH
1-235	N(Me)CH₂CH₂OMe	Me	0	0	OH
1-236	NHPh	Me	0	0	OH
1-237	NHCH₂Ph	Me	0	0	OH
1-238	N=CMe₂	Me	0	0	OH
1-239	N=CEt₂	Me	0	0	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 8]

Compound No.	R¹	R²	Y	z	R⁴
1-240	N=CHNMe₂	Me	O	0	OH
1-241	NHC(=O)Me	Me	0	0	OH
1-242	N[C(=O)Me]₂	Me	0	0	OH
1-243	NHC(=O)OMe	Me	0	0	OH
1-244	N[C(=O)OMe)₂	Me	0	0	OH
1-245	NHSCWe	Me	0	0	OH
1-246	NHSOzPh	Me	0	0	OH
1-247	NHSO₂CH₂Ph	Me	0	0	OH
1-248	OMe	Me	0	0	OH
1-249	OEt	Me	0	0	OH
1-250	OPr-n	Me	0	0	OH
1-251	OPri	Me	0	0	OH
1-252	OCH₂Prc	Me	0	0	OH
1-253	OCH₂C1	Me	0	0	OH
1-254	OCHCls	Me	0	0	OH
1-255	OCCla	Me	0	0	OH
1-256	OCH₂F	Me	0	0	OH
1-257	OCHFj	Me	0	0	OH
1-258	OCF₃	Me	0	0	OH
1-259	Ph	Et	0	0	OH
1-260	Ph	Pr-i	0	0	OH
1-261	Ph	chf₂	0	0	OH
1-262	Ph	Ph	0	0	OH
1-263	Ph	Me	0	s	OH
1-264	Ph	Me	s	s	OH
1-265	Me	Me	0	s	OH
1-266	Me	Me	s	s	OH
1-267	Ph	Me	0	0	SPh
1-268	Ph(4-OEt)	Me	0	0	OH
1-269	Ph(2-Ph)	Me	0	0	OH
1-270	Ph(3-Ph)	Me	0	0	OH
1-271	Ph(4-Ph)	Me	0	0	OH
	Me
1-272	-Al	Me	0	0	OH
	,OMe
	N=<
1-273	—⁴ J	Me	0	0	OH
	N-A
	OMe
		N=\
1-274	Me		0	0	OH
		N=\
1-275	Et		0	0	OH

1-276	ill	Me	0	0	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 9]

Compound No.	R¹	R²	Y	z	R⁴
1-277		Me	O	0	OH
1-278	A	Me	0	0	OH
1-279	'''CP'Me	Me	0	o	OH
1-280	/Uj	Me	0	0	OH
1-281		Me	0	o	OH
1-282	Ph(2-Me-4-Bri	Me	0	o	OH
1-283	Ph(2-Me-4-I)	Me	0	0	OH
1-284	Ph(2-Me-5-CF3)	Me	0	0	OH
1-285	Ph(2Me-6OCF3)	Me	0	0	OH
1-286	Ph(2-Pr-i)	Me	0	0	OH
1-287	_AAzOMe	Me	0	0	OH
1-288	Ph(2-Et)	Me	0	o	OH
1-289	XT	Me	0	o	OH
1-290		Me	0	0	OH
1-291	1 J	Me	0	s	OH
1-292	jy	Me	0	0	OH
1-293		Me	0	0	OH
1-294	CH₂COOBut	Me	0	o	OH
1-295	(C₇Hi4)CH3	Me	0	0	OH
I 296	(CgHijOCHa	Me	0	0	OH
1-297	Ph(2-F,4-Cl,5-OMe)	Me	0	o	OH
1-298	Ph(2,3,4-(OMe)₃	Me	0	0	OH
1-299	Ph(3,5-Cl₂-4-OMe)	Me	0	o	OH
1-300	Ph(3,5-Cl₂-4-SMe)	Me	0	0	OH
1-301	Ph(3,5C15-4-SO₂Me)	Me	0	0	OH
1-302	Ph(3,4,5-Fs)	Me	0	o	OH
1-303		Me	0	o	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 10]

Compound No.	R¹	R²	Y	z	R⁴
1-304	x^oh	Me	O	0	OH
1-305		Me ^N=\	O	0	OH
1-306	Bu-n	ⁿ=\	O	0	OH
1-307	CH₂CH(CH3)₂		O	0	OH
1-308	Ph	Penn	0	0	OH
I-30S	H	Me	0	0	OH
1-310	CH₂C = CF	Me	0	0	OH
1-311		Me	0	0	OH
1-312	λΌΙ	Me	0	0	OH
1-313	ch₂nh₂	Me	0	0	OH
1-314	CH₂NO2	Me	0	0	OH
1-315	CH₂NHCH3	Me	0	0	OH
1-316	CH₂N(CHa)₂	Me	0	0	OH
1-317	CH₂SCH₂CF3	Me	0	0	OH
1-318	CH₂SOCH₂CF_s	Me	0	0	OH
1-319	CH₂SO₂CH₂CF₃	Me	0	0	OH
1-320	ch₂oh	Me	0	0	OH
1-321	CH₂OBn	Me	0	0	OH
1-322	CH₂OCH₂Pr-c	Me	0	0	OH
1-323	CH₂OPh	Me	0	0	OH
1-324	CH₂SPh	Me	0	0	OH
1-325	CH₂SOPh	Me	0	0	OH
. 1-326	CH₂SO₂Ph	Me	0	0	OH
1-327	CH₂CON(CHs)₂	Me	0	0	OH
1-328	ch₂coch₃	Me	0	0	OH
1-329	ch₂ococh₃	Me	0	0	OH
1-330	ch₂on=chch₃	Me	0	0	OH
1-331	C₂H₄OC₂H₄SCH₃	Me	0	0	OH
1-332	CzHiOCjHiSOCHa	Me	0	0	OH
1-333	C2H4OC2H4SO2CH3	Me	0	0	OH
1-334	CH₂OCH₂CN	Me	0	0	OH
1-335	ch₂cn	Me	0	0	OH
1-336	och₂ch=ch₂	Me	0	0	OH
1-337	och₂c=ch	Me	0	0	OH
1-338	OPrc	Me	0	0	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 11]

Compound No.	R¹	R²	Y	z	R⁴
1-339	CH₂Rp Me	Me	0	0	OH
1-340	CH₂A O-N	Me	O	0	OH
1-341	ch₂-<T O-N	Me	0	0	OH
1-342	CH₂OCH₂^'°^	Me	0	0	OH
1-343	CH₂CH₂OCH₂CH₂O-^0>	Me	0	0	OH
1-344	Ph	H	0	0	OH
1-345	Ph	ch₂ch=ch₂	0	0	OH
1-346	Ph	ch₂c=ch	0	0	OH
1-347	Ph	Pr-c	0	0	OH
1-348	Ph	CH₂CH=CF₂	0	0	OH
1-349	Ph	ch₂c=cf	0	0	OH
1-350	Ph	C2H4OCH3	0	0	OH
1-351	Ph	C2H4OC2H5	0	0	OH
1-352	Ph	CH£Me)OEt	0	0	OH
1-353	Ph	CH₂OPr-c	0	0	OH
1-354	Ph	CH(OCH3)₂	0	0	OH
1-355	Ph	CH₂Ph	0	0	OH
1-356	Ph		0	0	OH
1-357	Ph		0	0	OH
1-358	Ph	Me	0	0	nh₂
1-359	Ph	Me	0	0	Cl
1-360	Ph	Me	0	0	CN
1-361	Ph	Me	0	0	NCS
1-362	Ph	Me	0	0	NCO
1-363	Ph	Me	0	0	OCOsH
1-364	Ph	Me	0	0	OCO2CH3
1-365	Ph	Me	0	0	OCO₂CH₂Ph
1-366	Ph	Me	0	0	OMe
1-367	Ph	Me	0	0	OEt
1-368	Ph	Me	0	0	OPr
1-369	Ph	Me	0	0	OCH₂CH=CH₂
1-370	Ph	Me	0	0	ΟΟΗ₂ΟξΟΗ
1-371	Ph	Me	0	0	OPr-c
1-372	Ph	Me	0	0	OBu-c
1-373	Ph	Me	0	0	OPen-c

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 12]

Compound No.	R¹	R²	Y	z	R⁴
1-374	Ph	Me	0	0	OHexc
1-375	Ph	Me	0	0	OCH₂CN
1-376	Ph	Me	o	0	OCH₂Pr-c
1-377	Ph	Me	0	0	OCOCH3
1-378	Ph	Me	0	0	OCOCCI3
1-379	Ph	Me	0	0	ococh=ch₂
1-380	Ph	Me	0	0	ococh=cf₂
1-381	Ph	Me	0	0	ococh₂c=ch
1-382	Ph	Me	0	0	ococh₂c=cf
1-383	Ph	Me	0	0	och₂co₂ch₃
1-384	Ph	Me	0	0	OPh
1-385	Ph	Me	0	0	OCH₂Ph
1-386	Ph	Me	0	0	OCOPh
1-387	Ph	Me	0	0	OCOCH₂Ph
1-388	Ph	Me	0	0	OCHzCOPh
1-389	Ph	Me	0	o	OSO₂CH₂CF₃
1-390	Ph	Me	0	0	OSO₂CH₂Ph
1-391	Ph	Me	0	o	SCHg
1-392	Ph	Me	0	0	SOCHg
1-393	Ph	Me	0	0	SO₂CH_s
1-394	Ph	Me	0	0	sch₂cf₃
1-395	Ph	Me	0	o	soch₂cf₃
1-396	Ph	Me	o	0	so₂ch₂cf₃
1-397	Ph	Me	0	o	sch₂ch=ch₂
1-398	Ph	Me	0	o	soch₂ch=ch₂
1-399	Ph	Me ------	o	o	so₂ch₂ch=ch₂
1-400	Ph	Me	o	o	sch₂ch=ch
1-401	Ph	Me	0	0	soch₂ch=ch
1-402	Ph	Me	0	0	so₂ch₂ch=ch
1-403	Ph	Me	0	0	SCH₂Ph
1-404	Ph	Me	0	0	SOPh
1-405	Ph	Me	0	0	SOCH₂Ph
1-406	Ph	Me	0	0	SO₂Ph
1-407	Ph	Me	0	0	SO₂CH₂Ph
1-408	Ph	Me	0	0	nhch₃
1-409	Ph	Me	0	0	N(CHs)₂
1-410	Ph	Me	0	0	NHCOCHs
1-411	Ph	Me	0	o
1-412	Ph	Me	0	0	—

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 13]

Compound No.	R¹	R²	Y	z	R⁴
1-413	Ph	Me	0	0	— vN —
1-414	Ph	Me	O	0
1-415	Ph	Me	0	0	—N' (j
1416	Ph	Me	0	0	Ο-/Λ
1-417	(4-Pr-c)Ph	Me	0	0	OH
1-418	(4-CH₂Pr-c)Ph	Me	0	0	OH
1-419	(4-CH₂=CHCH2)Ph	Me	0	o	OH
1-420	(4-CH=CCHs)Ph	Me	0	o	OH
1-421	(4-CH₂CH=CF2)Ph	Me	0	o	OH
1-422	(4-CH₂CH = CF)Ph CGCI	Me	0	0	OH
1-423		Me	0	0	OH
1-424	ci \|>-ci	Me	0	0	OH
1-425		Me	o	o	OH
1-426		Me	0	0	OH
1-427	-((-°	Me	0	o	OH
1-428	J-Me	Me	0	0	OH
1-429	(4OCHF₂)Ph	Me	0	0	OH
1-430	(4SMe)Ph	Me	0	0	OH
1-431	(4-SOMe)Ph	Me	0	0	OH
1-432	(4-SO₂Me)Ph	Me	0	o	OH
1-433	(4-SCFs)Ph	Me	0	0	OH
1-434	(4-SOCF₃)Ph	Me	0	o	OH
1-435	(4-SO₂CF3)Ph	Me	0	0	OH
1-436	-- _ 0 ^'%-NHCMe	Me	0	0	OH
1-437	Me	0	0	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 14]

Compound No.	R¹	R²	Y	z	R⁴
1-438		H -N-Me	Me	O	0	OH
1-439		-NMe₂	Me	0	0	OH
1-440		OH	Me	0	0	OH
1-441		OMe	Me	0	0	OH
1-442		SMe	Me	0	0	OH
1-443		SOMe	Me	0	0	OH
1-444		SO₂Me	Me	0	0	OH
1-445		_ySCF₃	Me	0	0	OH
1-446		SOCF₃	Me	0	0	OH
1-447		JSO₂CF₃	Me	0	0	OH
1-448		CN	Me	0	0	OH
1-449	“VA	^OMe -0	Me	0	0	OH
1-450		-0^	Me	0	0	OH
1-451	^—O’	/—OMe -O	Me	0	0	OH
1-452		^CN -0	Me	0	0	OH
1-453		Me 0	Me	0	0	OH
1-454		_zN-OMe	Me	0	0	OH
1-455		0 OH	Me	0	0	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 15]

Compound No.	R¹	R²	Y	z	R⁴
1-456	_/=\_p ~'(DMe	Me	0	0	OH
1-457	z=\ 0	Me	0	0	OH
1-458	_/=\λ° NJ''ΝΠΜθ	Me	0	0	OH
1-459	/=\λ° ^-^NMe₂	Me	0	o	OH
1-460		Me	0	0	OH
1-461		Me	0	0	OH
	Et
1-462	i j	Me	0	0	OH
1-463		Me	0	0	OH
	OMe
1-464	1 -OMe 1 1	Me	0	s	OH

1-465	Ph(3,4,5-Cl)	Me	0	0	OH
1-466	N(Me)Ph Me	Me	0	0	OH
1-467	x>„.	Me	0	0	OH
1-468	CHsCO(Bu-t)	Me	0	0	OH
1-469	Ph(2,3,5,6-F₄)	Me	0	0	OH
1-470	Ph[(3,5-(CFs)2]	Me	0	0	OH
1-471	CH₂C(Me)=NOMe	Me	0	0	OH
1-472	Ph(2,4,6-M_e8)	Me	0	0	OH
1-473	Ph(2,3,4,5,6Fs)	Me	0	0	OH
1-474	N(Et)Ph	Me	0	0	OH
1-475	N(Pr-i)Ph	Me	0	0	OH
1-476	N(Me)Ph(4F)	Me	0	0	OH
1-477	Ph	CH₂CF₃	0	o	OH
1-478	CH₂C(Me)=NOEt	Me	0	0	OH
1-479	CH₂C(Me>NO(Pr-i)	Me	0	0	OH
1-480	Ph(4-F)	Me	0	s	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 16]

R²¹ Ο Y
Compound No.	R¹	R²	Y	z	R²⁰	R²¹	R⁴
Ill	Me	Me	O	0	Me	H	OH
II-2	Et	Me	O	0	Me	Me	OH
Π-3	Pr-n	Me	O	0	Me	H	OH
II-4	Pr-i	Me	O	0	Me	H	OH
II-5	Bun	Me	O	0	Me	H	OH
II-6	Bu-i	Me	O	0	Me	H	OH
II-7	Bus	Me	O	0	Me	Me	OH
II-8	Bu-t	Me	O	0	Me	H	OSO₂Pr
II-9	Hex-n	Me	O	0	Me	H	OH
11-10	CH₂CF₃	Me	O	0	Me	H	OH
11-11	CH₂CH=CH₂	Me	O	0	Et	H	OH
11-12	CH₂C(Me)=CH₂	Me	O	0	Me	H	OH
11-13	CH₂CH₂CH=CMe₂	Me	O	0	Me	H	OH
11-14	ch₂c=ch	Me	O	0	Me	Me	OH
11-15	ch₂c=cch₃	Me	O	0	Me	H	OSO₂Ph
Π-16	Pr-e	Me	O	0	Me	H	OH
11-17	Bu-c	Me	O	0	i-Pr	H	OH
11-18	Penc	Me	O	0	Me	H	OH
11-19	Hexc	Me	O	0	Et	H	OH
11-20	CH₂Pr-c	Me	O	0	Me	H	OH
11-21	CH₂Bu-c	Me	O	0	Me	H	OH
11-22	CH₂Penc	Me	O	0	Me	Me	OH
11-23	CH₂Hexc	Me	0	0	Me	H	OH
11-24	CH₂CH=CC1₂	Me	0	0	Me	H	OSO₂Pr
11-25	ch₂cci=chci	Me	0	0	Me	H	OH
11-26	ch₂ch₂ch=cci₂	Me	0	0	Et	H	OH
11-27	CH₂CH₂C(Me)=CF₂	Me	0	0	Me	H	OH
11-28	CH₂CH₂CH₂CH₂C(Me)=CF₂	Me	0	0	Me	H	OH
11-29	CH₂CH=CF₂	Me	0	0	Me	Me	OH
11-30	CH₂CH₂OMe	Me	0	0	Me	H	OH
11-31	CH₂CH₂OEt	Me	0	0	Me	H	OH
11-32	CH(Me)CH₂OMe	Me	0	0	Pri	H	OH
11-33	CH₂CH₂OCH₂CH₂OMe	Me	0	0	Me	H	OH
11-34	CH₂CH₂OPr-n	Me	0	0	Et	H	OH
11-35	CH₂CH₂OPri	Me	0	0	Me	H	OH
11-36	CH₂CH₂OPr-c	Me	0	0	Me	Me	OH
11-37	CH₂CH₂OBuc	Me	0	0	Me	H	OH
II-38	CH₂CH₂OPen-c	Me	0	0	Me	H	OH
11-39	CH₂CH₂OHex-c	Me	0	0	Me	H	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 17]

Compound No.	R¹	R²	Y	z	R²⁰	R²¹	R⁴
Π-40	CH₂CH₂OCH₂CF₃	Me	O	0	Et	Me	OH
11-41	CH₂CH₂CH₂OMe	Me	O	o	Me	H	OH
11-42	CH=CHMe	Me	0	o	Me	H	OSO₂Ph
Π·43	CH₂SMe	Me	0	o	Me	H	OH
11-44	CH₂SPr-n	Me	0	0	Me	H	OH
11-45	CH₂CH₂SMe	Me	0	0	Pr-i	H	OH
Π-46	CH₂CH₂SOMe	Me	0	0	Me	H	OH
11-47	CH₂CH₂SO₂Me	Me	0	o	Me	Me	OH
Π-48	CH₂CH₂CH₂SMe	Me	0	o	Et	H	OH
11-49	CH₂CH₂CH₂SO₂Me	Me	0	o	Me	H	OH
11-50	Ph	Me	0	0	Me	H	OH
11-51	Ph(2-C0	Me	0	0	Me	H	OH
Π-52	Ph(3-CD	Me	0	o	Me	H	OH
Π-53	Ph(4-Cl)	Me	0	0	Me	H	OSO₂Pr
11-54	Ph(2-F)	Me	0	0	Pr-i	H	OH
11-55	Ph(3-F)	Me	0	0	Me	H	OH
11-56	Ph(4-F)	Me	0	0	Me	H	OH
11’57	Ph(2-Me)	Me	0	0	Me	Me	OH
11-58	Ph(3-Me)	Me	0	0	Me	H	OH
11-59	Ph(4-Me)	Me	0	0	Et	H	OH
11-60	Ph(2-OMe)	Me	0	o	Me	H	OH
11-61	Ph(3OMe)	Me	0	0	Me	H	OH
11-62	Ph(4-OMe)	Me	0	0	Me	H	OH
Π-63	Ph(2-CFs)	Me	0	0	Me	H	OH
11-64	PhO-CFa)	Me	0	0	Pr-i	H	OSO₂Ph
Π-65	Ph(4-CFa)	Me	0	0	Me	H	OH
11-66	Ph(2-NO₂)	Me	0	0	Me	H	OH
11-67	PhO-NOz)	Me	0	0	Me	H	OH
11-68	PhU-NOz)	Me	0	0	Me	Me	OH
11-69	PhteOCFs)	Me	0	0	Me	H	OH
11-70	Phte-OCFs)	Me	0	0	Et	H	OH
11-71	Ph(4-0CFs)	Me	0	0	Me	H	OH
11-72	Ph(2-CN)	Me	0	0	Me	H	OH
11-73	Ph(3-CN)	Me	0	0	Me	H	OH
11-74	Ph(4-CN)	Me	0	0	Me	H	OH
11-75	Phfe.LFz)	Me	0	0	Pr-i	H	OH
11-76	Ph(3,5'F₂)	Me	0	0	Me	H	OH
11-77	Ph(2,3-F2)	Me	0	0	Me	Me	OSO₂Pr
11-78	Ph(2,4-F₂)	Me	0	0	Me	H	OH
11-79	Ph(2,5-F2)	Me	0	0	Me	H	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 18]

Compound No.	R¹	R²	Y	z	R²⁰	R²¹	R⁴
11-80	Ph(2,6-F2)	Me	0	0	Et	Me	OH
11-81	Ph(3,4-C12)	Me	0	0	Me	H	OH
11-82	Ph(3,5-C12)	Me	0	0	Me	H	OH
11-83	Ph(2,3-C12>	Me	0	0	Me	H	OH
11-84	Ph(2,4-Cl₂)	Me	0	0	Me	H	OH
11-85	Ph(2,5-Cl₂)	Me	0	0	Pri	H	OH
11-86	Ph(2,6-C12)	Me	0	0	Me	H	OH
11-87	Ph(3,4-Me₂)	Me	0	0	Me	H	OH
II-88	Ph(3,5-Me₂)	Me	0	0	Me	H	OH
11-89	Ph(2,3-Me₂)	Me	0	o	Me	Me	OH
11-90	Ph(2,4-Me₂)	Me	0	o	Me	H	OH
11-91	Ph(2,5-Me₂)	Me	0	0	Me	H	OH
11-92	Ph(2,6-Me₂)	Me	0	0	Me	H	OH
11-93	Ph(3.4-(OMe)2)	Me	0	0	Me	H	OH
11-94	Ph(3,5-(OMe)2)	Me	0	0	Me	H	OH
11-95	Ph(2,3‘(OMe)2)	Me	0	o	Me	H	OH
11-96	Ph(2,4-(OMe)2)	Me	0	0	Pr-i	H	OH
11-97	Ph(2,5-(OMe)₂)	Me	0	0	Me	H	OSO₂Ph
11-98	Ph(2,6-(OMe)₂)	Me	0	0	Me	H	OH
11-99	Ph(3-F-4-OMe)	Me	0	0	Me	Me	OH
11-100	Ph(3-F-5-OMe)	Me	0	0	Me	H	OH
11-101	Ph(2-F-3-OMe)	Me	0	0	Me	H	OH
11-102	Ph(2-F-4-OMe)	Me	0	0	Me	H	OH
11-103 -	Ph(2-F-5-OMe)	Me	0	0	Me	H	OH
11-104	Ph(2-F-6-OMe)	Me	0	0	Me	H	OH
11-105	Ph(3-F-4-Me)	Me	0	0	Me	H	OSO₂Pr
11-106	Ph(3-F-5-Me)	Me	0	0	Me	H	OH
11-107	Ph(2-F-3-Me)	Me	0	0	Me	H	OH
11-108	Ph(2-F-4-Me)	Me	o	0	Me	H	OH
11-109	Ph(2-F-5-Me)	Me	0	0	Me	Me	OH
11-110	Ph(2-F-6-Me)	Me	0	0	Me	H	OH
11-111	Ph(3OMe-4F)	Me	0	0	Me	H	OH
11-112	Ph(2-OMe-3-F)	Me	0	0	Pr-i	H	OSO₂Ph(4-Me)
11-113	Ph(2-OMe-4-F)	Me	0	0	Me	H	OH
11-114	Ph(2-OMe-5-F)	Me	0	0	Me	H	OH
11-115	Ph(3-Me-4-F)	Me	0	0	Me	H	OH
11-116	Ph(2-Me-3-F)	Me	0	0	Me	H	OH
11-117	Ph(2Me-4F)	Me	0	0	Me	H	OH
11-118	Ph(2-Me-5-F)	Me	0	0	Me	H	OH
11-119	Ph(3-Cl-4-OMe)	Me	0	0	Me	Me	OH
11-120	Ph(3-Cl-5-OMe)	Me	0	0	Me	H	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 19]

Compound No.	R¹	R^z	Y	z	R²⁰	R²¹	R⁴
ΙΙΊ21	Ph(2Cl-3-OMe)	Me	0	0	Me	H	OH
11-122	Ph(2Cl-4OMe)	Me	0	o	Me	H	OSO₂Ph(4-Me)
11-123	Ph(2-Cl-5-OMe)	Me	0	o	Pr-i	H	OH
II-124	Ph(2-Cl-6-OMe)	Me	0	0	Me	H	OH
11-125	Ph(3-Cl-4-Me)	Me	0	0	Me	H	OH
II-126	Ph(3-Cl-5-Me)	Me	0	0	Me	Me	OH
11-127	Ph(2-Cl-3-Me)	Me	0	0	Me	H	OH
II-128	Ph(2-Cl-4-Me)	Me	0	o	Me	H	OH
11-129	Ph(2-Cl-5-Me)	Me	0	0	Me	H	OH
11-130	Ph(2-Cl-6-Me)	Me	0	0	Me	H	OH
11-131	Ph(3OMe-4-Cl)	Me	0	0	Me	H	OH
11-132	Ph(2OMe-3-Cl)	Me	0	0	Me	H	OSO₂Ph
11-133	Ph(2-OMe-4-Cl)	Me	0	o	Pr-i	H	OH
II-134	Ph(2OMe-5Cl)	Me	0	0	Me	H	OH
II-135	Ph(3-Me-4-Cl)	Me	0	0	Me	Me	OH
11-136	Ph(2-Me-3-CD	Me	0	0	Me	H	OH
11-137	Ph(2-Me-4-Cl)	Me	0	0	Me	H	OH
11-138	Ph(2-Me-5-Cl)	Me	0	0	Me	H	OH
11-139	Ph(3F-4-Cl)	Me	0	0	Me	H	OSO₂Ph(4-Me)
11-140	Ph(3-F-5-Cl)	Me	0	0	Me	H	OH
11-141	Ph(2-F-3-CD	Me	0	0	Me	H	OH
11-142	Ph(2-F-4-Cl)	Me	0	0	Me	H	OH
11-143	Ph(2-F-5-Cl)	Me	0	0	Me	H	OH
11-144	Ph(2-F-6-Cl)	Me -	0	o	Me	H	OH -----------
11-145	Ph(3-Cl-4-F)	Me	0	o	Me	H	OH
11-146	Ph(2-Cl-3-F)	Me	0	0	Me	Me	OH
11-147	Ph(2-Cl-4-F)	Me	0	0	Me	H	OH
11-148	PH2-C1-5-F)	Me	0	0	Pr-i	H	OH
II 149	Ph(3Me-4OMe)	Me	0	0	Me	H	OH
11-150	Ph(3-Me-5-OMe)	Me	0	0	Me	H	OH
11-151	Ph(2-Me-3-OMe)	Me	0	0	Me	H	OSO₂Ph(4-Me;
11-152	Ph(2-Me-4-OMe)	Me	0	0	Me	H	OH
11-153	Ph(2-Me-5-OMe)	Me	0	0	Me	H	OH
II-154	Ph(2-Me-6-OMe)	Me	0	0	Me	H	OH
IIT55	Ph(3-OMe-4-Me)	Me	0	0	Me	Me	OH
IIT56	Ph(2OMe-3-Me)	Me	0	0	Me	H	OH
11-157	Ph(2-OMe-4-Me)	Me	0	0	Me	H	OH
11-158	Ph(2-OMe-5-Me)	Me	0	o	Me	Me	OH
11-159	Ph(3-CN-4-OMe)	Me	0	0	Me	H	OH
11-160	Ph(3-OMe-4-CN)	Me	0	0	Me	H	OH
11-161	Ph(3-Me-4-CN)	Me	0	0	Pri	H	OSO₂Ph(4Me)

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 20]

Compound No.	R¹	R²	Y	z	R²⁰	R²¹	R⁴
11-162	Ph(3-CN-4-Me)	Me .	O	0	Me	H	OH
11-163	Ph(3-NO₂-4-OMe)	Me	O	o	Me	H	OH
Π-164	Ph(3-OMe-4-NO2)	Me	O	0	Me	H	OH
11-165	Ph(3-Me-4-NO2)	Me	O	0	Me	H	OH
11-166	Ph(3-NO₂-4-Me)	Me	O	0	Me	H	OH
11-167	Ph(3,5-F₂-5-OMe)	Me	O	0	Me	H	OH
11-168	Ph(3,5-F₂-5-Me)	Me	O	o	Me	Me	OH
11-169	Ph(3,4,5-(OMe)3)	Me	O	o	Me	H	OH
11-170	0	Me	O	0	Me	H	OH
11-171		Me	O	o	Me	H	OH
11-172	V	Me	O	0	Pri	H	0S0jPh(4Me)
11-173		Me	O	0	Me	H	OH
11-174		Me	O	0	Me	H	OH
11-175		Me	0	0	Me	Me	OH
11-176		Me	O	0	Me	H	OH
11-177		Me	0	0	Me	H	OH
11-178		Me	0	0	Me	H	OH
11-179		Me	0	0	Me	H	OH
11-180	-33	Me	0	0	Me	H	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 21]

Compound. No.	R¹	R²	Y	z	R²⁰	R²¹	R⁴
11-181		Me	O	0	Me	H	OH
II-182	--fl—	Me	0	0	Me	H	OH
11-183	——OMe	Me	0	0	Me	H	OH
Π-184		Me	0	0	Pri	H	OH
11-185	O^ci	Me	0	0	Me	Me	OH
11-186		Me	0	0	Me	H	OH
Π-187		Me	0	0	Me	H	OH
11-188	-Me	Me	o	0	Me	H	OH
11-189	v°........	Me	0	0	Me	H	OSO₂Ph(4-Me)
Π190		Me	0	0	Me	H	OH
Π-191	.Me	Me	0	0	Me	H	OH
Π-192		Me	o	0	Me	H	OH
11-193	Ν'θ	Me	0	0	Me	H	OH
ΙΙΊ94	—(^S~l >r	Me	0	0	Me	H	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 22]

Compound No.	R¹	R²	Y	z	R²⁰	R²¹	R⁴
IIT95	—(T	Me	0	0	Me	H	OH
11-196	N	Me	0	o	Me	H	OH
11-197	N^Me —ς Ύ	Me	0	0	Me	H	OH
II-198	N^Me s—,	Me	0	0	Me	H	OH
11-199		Me	0	o	Pr-i	Me	OH
11-200		Me	0	o	Me	H	OH
Π-201 11-202		Me Me	0 0	0 0	Me Me	H H	OH OH
11-203	^—nCZ/^s	Me	0	0	Me	H	OH
11-204	—θο₂	Me	0	0	Me	Me	OH
11-205	CH₂Ph	Me	0	o	Me	H	OH
11-206	CH₂CH₂Ph	Me	0	0	Me	H	OH
11-207	CH₂CH₂CH₂Ph	Me	o	0	Me	H	OH
11-208	CH₂CH=CHPh	Me	0	0	Me	H	OH
Π-209	CH₂C = CPh	Me	0	0	Me	H	OH
11-210	CH₂CH=NOMe	Me	0	0	Me	H	OH
11-211	CH₂CH=NOEt	Me	0	0	Me	H	OH
11-212	CH₂CH=NOPr-n	Me	0	0	Me	H	OH
11-213	CH₂CH=NOPh	Me	0	0	Me	Me	OH
11-214	CH₂CH(OMe)₂	Me	0	0	Me	H	OH
11-215	CH₂CHO	Me	0	0	Et	H	OH
11-216	nh₂	Me	0	0	Me	H	OH
11-217	NHMe	Me	0	0	Me	H	OH
11-218	NHEt	Me	0	0	Me	H	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 23]

Compound No.	R¹	R²	Y	z	R²⁰	R²¹	R⁴
11-219	NHPrn	Me	0	0	Me	H	OSO₂Ph(4-Me)
11-220	NHPr-i	Me	0	0	Me	H	OH
Π-221	NHBu-n	Me	O	0	Pr-i	H	OH
Π-222	NHBiri	Me	O	0	Me	H	OH
Π-223	NHBu-s	Me	O	0	Me	Me	OH
Π-224	NHCH₂Pr-c	Me	O	0	Me	H	OH
11-225	NHPen-n	Me	O	0	Me	H	OH
Π-226	NHHex-n	Me	O	0	Me	H	OH
11-227	NHCH₂CH₂CH₂C1	Me	O	0	Me	H	OH
Π-228	nhch₂ch₂ch₂f	Me	O	0	Me	H	OH
Π-229	NHCH₂CH₂OMe	Me	0	0	Me	H	OH
11-230	NMe₂	Me	0	0	Me	H	OH
Π-231	NEt₂	Me	0	0	Me	H	OH
II-232	N(Pr-n)₂	Me	0	0	Me	H	OH
11-233	N(Bu-n)₂	Me	0	0	Me	H	OH
11-234	N(Me)Et	Me	0	0	Me	Me	OH
11-235	N(Me)CH₂CH₂OMe	Me	0	0	Et	H	OH
Π-236	NHPh	Me	0	0	Me	H	OH
11-237	NHCH₂Ph	Me	0	0	Me	H	OH
11-238	N=CMe₂	Me	0	0	Me	H	OH
11-239	N=CEtz	Me	0	0	Me	H	OSO₂Ph(4-Me)
11-240	N=CHNMe₂	Me	0	0	Me	H	OH
Π-241	NHC(=O)Me	Me	0	0	Me	H	OH
11-242	N[C(=O)Me]₂	Me	0	0	Me	H	OH
Π-243	NHC(=O)OMe	Me	0	0	Pr-i	H	OH
Π-244	N[C(=O)OMe]₂	Me	0	0	Me	H	OH
11-245	NHSOzMe	Me	0	0	Me	H	OH
Π-246	NHSO₂Ph	Me	0	0	Me	Me	OH
Π-247	NHSO₂CH₂Ph	Me	0	0	Me	H	OH
11-248	OMe	Me	0	0	Et	H	OH
11-249	OEt	Me	0	0	Me	H	OH
11-250	OPrn	Me	0	0	Me	H	OH
11-251	OPri	Me	0	0	Me	H	OH
Π-252	OCH₂Pr-c	Me	0	0	Me	H	OH
11-253	OCH₂C1	Me	0	0	Me	H	OH
Π-254	OCHC1₂	Me	0	0	Me	H	OH
11-255	OCC1₃	Me	0	0	Me	Me	OH
11-256	OCH₂F	Me	0	0	Me	H	OH
11-257	ochf₂	Me	0	0	Me	H	OH
11-258	OCF3	Me	0	0	Me	H	OSO₂Ph(4-Me)
11-259	Ph	Et	0	0	Et	H	OH
11-260	Ph	Pr-i	0	0	Me	H	OH
11-261	Ph	chf₂	0	0	Me	H	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 24]

Compound No.	R¹	R²	Y	z	R²⁰	R²¹	R⁴
11’262	Ph	Ph	O	0	Me	H	OH
11-263	Ph	Me	O	s	Me	Me	OH
11-264	Ph	Me	S	s	Me	H	OH
11-265	Me	Me	0	s	Me	H	OH
Π-266	Me	Me	s	s	Me	H	OH
Π-267	Ph	Me	0	0	Pri	H	OSO₂Pr
11-268	Ph(4-0Et)	Me	0	0	Me	H	OH
Π-269	Ph(2-Ph)	Me	0	0	Me	H	OH
11-270	Ph(3-Ph)	Me	0	0	Me	H	OH
11-271	Ph(4-Ph)	Me	0	0	Me	H	OH

11-272	-Cl Af₃	Me	0	0	Me	Me	OH
	„ ^^0Me
	N=<
11-273	—(\ y	Me	0	0	Et	H	OSO₂Ph(4-Me)
	N-A
	OMe
		N=\
Π-274	Me	AJ	0	0	Me	H	OH
		N=\
11-275	Et	Aj	0	0	Me	H	OH
11-276	H	Me	0	0	Me	H	OH
11-277	CH₂CECF	Me	0	0	Me	H	OH
	Cl Cl
11-278	Ji	Me	0	0	Me	H	OH
11-279	ZV^C1	Me	0	0	Me	H	OH
	'^X/^C1
11-280	ch₂nh₂	Me	0	0	Me	H	OH
11-281	ch₂no₂	Me	0	0	Me	H	OH
Π-282	CH₂NHCH₃	Me	0	0	Me	H	OH
II-283	CH₂N(CH₃)₂	Me	0	0	Me	H	OH
11-284	CH2SCH2CF3	Me	0	0	Me	H	OH
Π-285	CH2SOCH2CF3	Me	0	0	Me	H	OH
11-286	CH2SO2CH2CF3	Me	0	0	Me	H	OH
11-287	CH₂OH	Me	0	0	Me	H	OH
11-288	CH₂OBn	Me	0	0	Me	H	OH
11-289	CH₂OCH₂Pr-c	Me	0	0	Me	H	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 25]

Compound No.	R¹	R²	Y	z	R²⁰	R²¹	R⁴
Π-290	CH₂OPh	Me	O	0	Me	H	OH
11-291	CH₂SPh	Me	O	0	Me	H	OH
Π-292	CH₂SOPh	Me	O	0	Me	H	OH
11-293	CH₂SO₂Ph	Me	O	0	Me	H	OH
11-294	CH₂CON(CH3)₂	Me	O	0	Me	H	OH
Π-295	CHaCOCHa	Me	O	0	Me	H	OH
Π-296	CH2OCOCH3	Me	O	0	Me	H	OH
Π-297	CH₂ON=CHCH3	Me	O	0	Me	H	OH
Π-298	C₂H4OC2H4SCH3	Me	O	0	Me	H	OH
11-299	C₂H4OC₂H4SOCH3	Me	O	0	Me	H	OH
Π-300	C2H4OC2H4SO2CH3	Me	O	0	Me	H	OH
11-301	CH2OCH₂CN	Me	O	0	Me	H	OH
11-302	ch₂cn	Me	O	0	Me	H	OH
Π-303	OCH₂CH=CH₂	Me	O	0	Me	H	OH
11-304	och₂chch	Me	O	0	Me	H	OH
11-305	OPr-c	Me	0	0	Me	H	OH
11-306		Me	0	0	Me	H	OH
11-307	CH₂-<T^Me O-N ^Me	Me	0	0	Me	H	OH
11-308	CH₂-<T O-N .0.	Me'	0	0	Me	H	OH
11-309	CH₂OCH₂~Y >	Me	0	0	Me	H	OH
11-310	CH₂CH₂OCH₂CH₂O-/^?_/ Ν=^	Me	0	0	Me	H	OH
II 311	Ph	H	0	0	Me	H	OH
11-312	Ph	ch₂ch=ch₂	0	0	Me	H	OH
Π-313	Ph	ch₂c^ch	0	0	Me	H	OH
11-314	Ph	Pr-c	0	0	Me	H	OH
Π-315	Ph	ch₂ch=cf₂	0	0	Me	H	OH
Π-316	Ph	ch₂c^cf	0	0	Me	H	OH
Π-317	Ph	CaHiOCHs	0	0	Me'	H	OH
Π-318	Ph	C2H4OC2H5	0	0	Me	H	OH
Π-319	Ph	CH(Me)OEt	0	0	Me	H	OH
Π-320	Ph	CHaOPr-c	0	0	Me	H	OH
11-321	Ph	CH(OCH₃)₂	0	0	Me	H	OH
Π-322	Ph	CH₂Ph	0	0	Me	H	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 26]

Compound No.	R¹	R²	Y	z	R²⁰	R²¹	R⁴
11-323	Ph		0	0	Me	H	OH
11-324	Ph	— Q	0	0	Me	H	OH
11-325	Ph	Me	0	o	Me	H	nh₂
Π-326	Ph	Me	0	0	Me	H	Cl
11-327	Ph	Me	0	0	Me	H	CN
11-328	Ph	Me	0	o	Me	H	NCS
Π-329	Ph	Me	0	0	Me	H	NCO
11-330	Ph	Me	0	0	Me	H	OCO₂H
11-331	Ph	Me	0	0	Me	H	OCO2CH3
11-332	Ph	Me	0	0	Me	H	OCO2CH₂Ph
Π-333	Ph	Me	0	0	Me	H	OMe
11-334	Ph	Me	0	o	Me	H	OEt
Π-335	Ph	Me	0	o	Me	H	OPr
II-336	Ph	Me	0	o	Me	H	OCH₂CH=CH₂
Π-337	Ph	Me	0	0	Me	H	och₂c^ch
11-338	Ph	Me	0	0	Me	H	OPrc
11-339	Ph	Me	0	o	Me	H	OBu-c
11-340	Ph	Me	0	0	Me	H	OPen-c
Π-341	Ph	Me	0	0	Me	H	OHex-c
Π-342	Ph	Me	0	0	Me	H	OCH2CN
Π-343	Ph	Me	0	0	Me	H	OCH₂Pr-c
11-344	Ph	Me	0	0	Me	H	OCOCH3
11-345	Ph	Me	0	0	Me	H	OCOCCh
11’346	Ph	Me	0	o	Me	H	OCOCH=CH₂
11-347	Ph	Me	0	0	Me	H	OCOCH=CF₂
11’348	Ph	Me	0	o	Me	H	ococh₂c=ch
11-349	Ph	Me	0	0	Me	H	ococh₂c=cf
11-350	Ph	Me	0	0	Me	H	OCH2CO2CH3
11’351	Ph	Me	0	0	Me	H	OPh
11-352	Ph	Me	0	0	Me	H	OCH2Ph
11-353	Ph	Me	0	o	Me	H	OCOPh
11-354	Ph	Me	0	o	Me	H	OCOCH₂Ph
11-355	Ph	Me	0	0	Me	H	OCH₂COPh
Π-356	Ph	Me	0	0	Me	H	OSO2CH2CF3
11-357	Ph	Me	0	o	Me	H	OSO₂CH₂Ph
Π-358	Ph	Me	0	o	Me	H	SCH₃
11-359	Ph	Me	0	o	Me	H	SOCHg
11-360	Ph	Me	0	0	Me	H	SO2CH3
11-361	Ph	Me	0	0	Me	H	SCH2CF3
11-362	Ph	Me	0	0	Me	H	SOCH2CF3
11-363	Ph	Me	0	0	Me	H	SO2CH2CF3

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 21\

Compound No.	R¹	R²	Y	z	R²⁰	R²¹	R⁴
11-364	Ph	Me	0	0	Me	H	SCH₂CH=CH₂
11-365	Ph	Me	0	0	Me	H	soch₂ch=ch₂
Π-366	Ph	Me	0	0	Me	H	so₂ch₂ch=ch₂
11-367	Ph	Me	0	0	Me	H	sch₂ch=ch
11-368	Ph	Me	0	o	Me	H	soch₂ch^ch
Π-369	Ph	Me	0	0	Me	H	so₂ch₂ch=ch
11-370	Ph	Me	0	o	Me	H	SCH₂Ph
11-371	Ph	Me	0	0	Me	H	SOPh
11'372	Ph	Me	0	0	Me	H	SOCH₂Ph
11-373	Ph	Me	0	o	Me	H	SO₂Ph
11-374	Ph	Me	0	0	Me	H	SO₂CH₂Ph
11-375	Ph	Me	0	0	Me	H	NIICH,
Π376	Ph	Me	0	0	Me	H	N(CH3)₂
11-377	Ph	Me	0	0	Me	H	NHCOCHa
11-378	Ph	Me	0	0	Me	H	OCH₂CH₂-<^3 N^
11-379	Ph	Me	0	0	Me	H	-Or
11-380	Ph	Me	0	0	Me	H	-ⁿOn
11-381	Ph	Me	o	0	Me	H	-u
11-382	Ph	Me	0	0	Me	H	—
11-383	Ph	Me	0	0	Me	H	ο/Λ N=

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 28]

R⁴ Ο Y V’-'X) Ϊ²
Compound No.	R¹	R²	Y	z	R⁴
ΠΙ1	Me	Me	O	0	OH
ΠΙ-2	Et	Me	O	0	OH
III-3	Pr-n	Me	O	0	OH
III-4	Pr-i	Me	O	0	OH
III-5	Bun	Me	0	0	OH
III 6	Bu-i	Me	0	0	OH
III-7	Bu-s	Me	0	0	OH
III-8	Bu-t	Me	0	0	OH
III-9	Hex-n	Me	0	0	OH
III-10	CH2CF3	Me	0	0	OH
III-11	CH₂CH=CH₂	Me	0	0	OH
III-12	CH₂C(Me)=CH₂	Me	0	0	OH
III-13	CH₂CH₂CH=CMe₂	Me	0	0	OH
III-14	CH₂CECH	Me	0	0	OH
III-15	CH₂CSCCH₃	Me	0	0	OH
HI-16	Pr-c	Me	0	0	OH
III· 17	Buc	Me	0	0	OH
III-18	Pen-c	Me	0	0	OH
III-19	Hex-c	Me	0	0	OH
ΙΠ-20	CH₂Pr-c	Me	0	0	OH
ΙΠ-21	CH₂Bu-c	Me	0	0	OH
ΙΠ-22	CH₂Pen-c	Me	0	0	OH
ΙΠ-23	CHzHex’c	Me	0	0	OH
III-24	CH₂CH=CC1₂	Me	0	0	OH
ΙΠ-25	CH₂CC1=CHC1	Me	0	0	OH
ΙΠ-26	CH₂CH₂CH=CC1₂	Me	0	0	OH
ΙΠ-27	CH₂CH₂C(Me)=CF₂	Me	0	0	OH
ΙΠ-28	CH₂CH₂CH2CH₂C(Me)=CF₂	Me	0	0	OH
ΠΙ-29	CH₂CH=CF₂	Me	0	0	OH
ΙΠ-30	CH₂CH₂OMe	Me	0	0	OH
ΙΠ-31	CH₂CH₂OEt	Me	0	0	OH
ΙΠ-32	CH(Me)CH₂OMe	Me	0	0	OH
ΙΠ-33	CH₂CH₂OCH₂CH₂OMe	Me	0	0	OH
III-34	CH₂CH₂OPr-n	Me	0	0	OH
ΙΠ-35	CH₂CH₂OPr-i	Me	0	0	OH
ΙΠ-36	CH₂CH₂OPr-c	Me	0	0	OH
III-37	CH₂CH₂OBu-c	Me	0	0	OH
ΙΠ-38	CH₂CH₂OPen-c	Me	0	0	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 29]

Compound No.	R¹	R²	Y	z	R⁴
Ill-39	CH₂CH₂OHex-c	Me	O	0	OH
ΠΙ-40	CH₂CH₂OCH₂CF₃	Me	O	0	OH
III-41	CH₂CH₂CH₂OMe	Me	O	0	OH
HI-42	CH=CHMe	Me	0	0	OH
ΠΙ-43	CH₂SMe	Me	O	0	OH
III-44	CH₂SPr-n	Me	O	0	OH
III-45	CH₂CH₂SMe	Me	O	0	OH
ΠΙ-46	CH₂CH₂SOMe	Me	O	0	OH
III-47	CH₂CH₂SO₂Me	Me	O	0	OH
ΠΙ-48	CH₂CH₂CH₂SMe	Me	O	0	OH
III-49	CH₂CH₂CH₂SO₂Me	Me	0	0	OH
III-50	Ph	Me	0	0	OH
III-51	Ph(2-Cl)	Me	0	0	OH
III-52	Ph(3-CD	Me	O	0	OH
III-53	Ph(4-Cl)	Me	O	0	OH
III-54	Ph(2-F)	Me	O	0	OH
III-55	Ph(3-F)	Me	O	0	OH
III-56	Ph(4-F)	Me	O	0	OH
HI-57	Ph(2-Me)	Me	O	0	OH
HI-58	Ph(3-Me)	Me	O	0	OH
HI-59	Ph(4-Me)	Me	O	0	OH
HI-60	Ph(2-OMe)	Me	O	0	OH
HI-61	Ph(3OMe)	Me	O	0	OH
HI-62	Ph(4-OMe)	Me	O	0	OH
III-63	Ph(2-CFa)	Me	O	0	OH
ΠΙ-64	PhO'CFa)	Me	0	0	OH
HI-65	Ph(4-CF3>	Me	0	0	OH
111-66	Ph(2NO₂)	Me	0	0	OH
HI-67	Ph(3-NO₂)	Me	0	0	OH
III-68	Ph(4-NO₂)	Me	o	0	OH
ΠΙ-69	Ph(2OCFs)	Me	o	0	OH
III-70	Ph(3-0CFs)	Me	o	0	OH
HI-71	PhUOCFj)	Me	0	0	OH
III-72	Ph(2-CN)	Me	0	0	OH
HI-73	Ph(3-CN)	Me	0	0	OH
III-74	Ph(4-CN)	Me	0	o	OH
III-75	Ph(3,4-F2>	Me	0	0	OH
III-76	Ph(3,5-F₂)	Me	0	0	OH
ΙΠ-77	Ph(2,3-F2)	Me	o	0	OH
ΙΠ-78	Ph(2,4-F2)	Me	0	0	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 30]

Compound No.	R¹	R²	Y	z	R⁴
HI-79	Ph(2,5-F₂)	Me	O	0	OH
III-80	Ph(2,6-F₂)	Me	O	0	OH
III-81	Ph(3,4-C12)	Me	O	0	OH
HI-82	Ph(3,5-C12)	Me	O	0	OH
HI-83	Ph(2,3-Cl₂)	Me	O	0	OH
ΙΠ-84	Ph(2,4-C12)	Me	O	0	OH
ΠΙ-85	Ph(2,5-Cl₂)	Me	O	0	OH
III-86	Ph(2,6-C12)	Me	O	0	OH
HI-87	Ph(3,4-Me₂)	Me	O	0	OH
III-88	Ph(3,5-Me₂)	Me	O	0	OH
ΙΠ-89	Ph(2,3-Me₂)	Me	O	0	OH
III-90	Ph(2,4-Me_z)	Me	O	0	OH
ΙΠ-91	Ph(2,5-Me₂)	Me	O	0	OH
ΠΙ-92	Ph(2,6-Me_z)	Me	O	0	OH
ΙΠ-93	Ph(3,4-(OMe)₂)	Me	O	0	OH
HI-94	Ph(3,5-(OMe)₂)	Me	O	0	OH
ΙΠ-95	Ph(2,3-(OMe)2)	Me	O	0	OH
ΙΠ-96	Ph(2,4-(OMe)₂)	Me	O	0	OH
ΠΙ-97	Ph(2,5-(OMe)₂)	Me	O	0	OH
ΙΠ-98	Ph(2,6-(OMe)₂)	Me	O	0	OH
ΠΙ-99	Ph(3-F-4-OMe)	Me	O	0	OH
III100	Ph(3F5OMe)	Me	O	0	OH
HI-101	Ph(2-F-3-OMe)	Me	O	0	OH
HI-102	Ph(2-F-4OMe)	Me	O	0	OH
III-103	Ph(2F-5-OMe)	Me	O	0	OH
HI-104	Ph(2-F-6-OMe)	Me	0	0	OH
HI-105	Ph(3-F-4-Me)	Me	0	0	OH
HI-106	Ph(3-F-5-Me)	Me	o	0	OH
HI-107	Ph(2-F-3-Me)	Me	0	0	OH
HI-108	Ph(2-F-4-Me)	Me	0	0	OH
HI-109	Ph(2-F5-Me)	Me	0	0	OH
HI-110	Ph(2-F-6-Me)	Me	o	o	OH
III-lll	Ph(3-OMe-4-F)	Me	o	0	OH
HI-112	Ph(2-OMe-3-F)	Me	0	0	OH
HI-113	Ph(2OMe-4F)	Me	0	0	OH
III-114	Ph(2OMe-5-F)	Me	0	0	OH
HI-115	Ph(3-Me-4-F)	Me	0	0	OH
HI-116	Ph(2-Me-3-F)	Me	0	0	OH
HI-117	Ph(2-Me-4-F)	Me	0	0	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 31]

Compound No.	R¹	R²	Y	z	R⁴
HI-118	Ph(2-Me-5-F)	Me	0	0	OH
111-119	Ph(3-Cl-4-OMe)	Me	0	0	OH
III-120	Ph(3-Cl-5-OMe)	Me	0	0	OH
III-121	Ph(2-Cl-3-OMe)	Me	0	0	OH
ΙΠ-122	Ph(2-Cl-4-OMe)	Me	0	0	OH
ΙΠ-123	Ph(2Cl-5OMe)	Me	0	0	OH
HI-124	Ph(2-Cl-6-OMe)	Me	0	0	OH
III-125	Ph(3Cl-4-Me)	Me	0	0	OH
ΠΙ-126	Ph(3Cl-5Me)	Me	0	0	OH
III-127	Ph(2-Cl-3-Me)	Me	0	0	OH
III-128	Ph(2-Cl-4-Me)	Me	0	0	OH
III-129	Ph(2-Cl-5-Me)	Me	0	0	OH
IH-130	Ph(2-Cl-6-Me)	Me	0	0	OH
III-131	Ph(3OMe-4-Cl)	Me	0	0	OH
III-132	Ph(2OMe-3CD	Me	0	0	OH
III-133	Ph(2-OMe-4-Cl)	Me	0	0	OH
III-134	Ph(2OMe-5-Cl)	Me	0	0	OH
III-135	Ph(3-Me-4-Cl)	Me	0	0	OH
III-136	Ph(2Me-3-CD	Me	0	0	OH
III-137	Ph(2-Me-4-Cfi	Me	0	0	OH
III-138	Ph(2-Me-5-Cl)	Me	0	0	OH
HI-139	Ph(3F-4-Cl)	Me	0	0	OH
III-140	Ph(3-F-5-Cl)	Me	0	0	OH
III-141	Ph(2-F-3CD	Me	0	0	OH
HI-142	Ph(2-F-4-Cl)	Me	0	0	OH
HI-143	Ph(2-F-5-Cl)	Me	o	0	OH
HI-144	Ph(2-F-6-Cl)	Me	0	0	OH
III-145	Ph(3-Cl-4-F)	Me	0	0	OH
III-146	PH2-C1-3-F)	Me	0	0	OH
HI-147	Ph(2-Cl-4-F)	Me	0	0	OH
HI-148	Ph(2-Cl-5-F)	Me	0	0	OH
HI-149	Ph(3-Me-4-OMe)	Me	0	0	OH
III-150	Ph(3-Me-5-OMe)	Me	0	0	OH
ΙΠ-151	Ph(2Me-3-OMe)	Me	0	0	OH
111*152	Ph(2-Me-4-OMe)	Me	0	0	OH
III-153	Ph(2Me-5-OMe)	Me	0	0	OH
ΙΠ-154	Ph(2-Me-6-OMe)	Me	0	0	OH
HI-155	Ph(3-OMe-4-Me)	Me	0	0	OH
HI-156	Ph(2-OMe-3-Me)	Me	0	0	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 32]

Compound No.	R¹	R²	Y	z	R⁴
HI-157	Ph(2-OMe-4-Me)	Me	O	0	OH
III-158	Ph(2OMe-5-Me)	Me	O	0	OH
111*159	Ph(3CN-4-OMe)	Me	0	0	OH
III-160	Ph(3-OMe-4-CN)	Me	0	0	OH
HI-161	Ph(3-Me-4-CN)	Me	O	0	OH
HI-162	Ph(3CN-4-Me)	Me	0	0	OH
HI-163	Ph(3NO₂-4-OMe)	Me	0	0	OH
111-164	Ph(3-OMe-4-NO2)	Me	O	0	OH
HI-165	Ph(3-Me-4-NO₂)	Me	O	o	OH
HI-166	Ph(3NO₂-4-Me)	Me	O	0	OH
HI-167	Ph(3,5-F₂-5-OMe)	Me	O	0	OH
III-168	Ph(3,5-F₂-5-Me)	Me	0	0	OH
HI-169	Ph(3,4,5-(OMe)3)	Me	O	o	OH
HI-170	-Q-o cr	Me	O	0	OH
HI-171		Me	O	0	OH
HI-172		Me	0	0	OH
HI-173	-O^-\ CK	Me	O	0	OH
III-174		Me	O	0	OH
HI-175		Me	O	0	OH
HI-176		Me	O	0	OH
HI-177		Me	O	0	OH
HI-178	Me	Me	O	0	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 33]

Compound No.	R¹	R²	Y	z	R⁴
HI-179		Me	O	0	OH
III-180		Me	O	0	OH
ΠΙ-181	-O	Me	0	0	OH
HI-182		Me	0	0	OH
HI-183	—OMe	Me	o	0	OH
111-164	——F	Me	0	0	OH
HI-185		Me	0	0	OH
HI-186		Me	0	0	OH
HI-187	N-”/^{- CF}®	Me	0	0	OH
HI-188	λα /==<^Me	Me	o	0	OH
HI-189	Ν'θ	Me	0	0	OH
HI-190	,-ζ!	Me	o	0	OH
ΙΠ-191	Me -σ	Me	0	0	OH
III-192		Me	0	0	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 34]

Compound No.	R¹	R²	Y	z	R⁴
		Me
III-193			Me	0	0	OH
	NT
	S-
III-194	-	J	Me	0	0	OH
	N
	S-	_-Me
III-195	-		Me	0	0	OH
	N'
	S—
ΠΙ-196	_		Me	O	0	OH
	N	Me
	^S~_A	_xMe
III-197			Me	O	0	OH
		''Me
	s-
HI-198		fl	Me	O	0	OH
		-s
HI-199			Me	O	0	OH

HI-200	AJ	f-Me	Me	O	0	OH
		S
HI-201			Me	O	0	OH
		^Me
111*202	—N		Me	O	0	OH
III-203	—N		Me	O	0	OH
III-204	—N	JSO₂	Me	O	0	OH
III-205	CH₂Ph		Me	O	0	OH
III-206	CH₂CH₂Ph		Me	O	0	OH
III-207	CH₂CH₂CH₂Ph		Me	O	0	OH
III-208	CH₂CH=CHPh		Me	O	0	OH
III-209	CH₂C = CPh		Me	O	0	OH
HI-210	CH₂CH=NOMe		Me	O	0	OH
111*211	CH₂CH=NOEt		Me	O	0	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 35]

Compound No.	R¹	R²	Y	z	R⁴
HI-212	CH₂CH=NOPrn	Me	0	0	OH
III-213	CH₂CH=NOPh	Me	O	0	OH
HI-214	CH₂CH(OMe)₂	Me	0	0	OH
III-215	CH₂CHO	Me	O	0	OH
III-216	nh₂	Me	O	0	OH
HI-217	NHMe	Me	O	0	OH
HI-218	NHEt	Me	0	0	OH
111*219	NHPr-n	Me	O	0	OH
III-220	NHPr-i	Me	O	0	OH
III-221	NHBu-n	Me	0	0	OH
HI-222	NHBu-i	Me	O	0	OH
III-223	NHBu-s	Me	O	0	OH
III-224	NHCH₂Pr-c	Me	O	0	OH
HI-225	NHPen-n	Me	O	0	OH
III-226	NHHex-n	Me	O	0	OH
HI-227	NHCH₂CH₂CH₂C1	Me	O	0	OH
III 228	NHCH₂CH₂CH₂F	Me	O	0	OH
HI-229	NHCH₂CH₂OMe	Me	O	0	OH
HI-230	NMe₂	Me	O	0	OH
HI-231	NEt2	Me	O	0	OH
HI-232	N(Pr-n)₂	Me	O	0	OH
HI-233	N(Bun)j	Me	O	0	OH
III-234	N(Me)Et	Me	O	0	OH
HI-235	N(Me)CH₂CH₂OMe	Me	O	0	OH
III-236	NHPh	Me	O	0	OH
HI-237	NHCH₂Ph	Me	O	0	OH
HI-238	N=CMe₂	Me	O	0	OH
HI-239	N=CEt₂	Me	O	0	OH
HI-240	N=CHNMe₂	Me	O	0	OH
HI-241	NHC(=O)Me	Me	0	0	OH
III-242	N[C(=O)Me]₂	Me	0	0	OH
HI-243	NHC(=0)OMe	Me	0	0	OH
III-244	N[C(=O)OMe]₂	Me	0	0	OH
HI-245	NHSOsMe	Me	0	0	OH
ΙΠ-246	NHSO₂Ph	Me	0	0	OH
III-247	NHSO₂CH₂Ph	Me	0	0	OH
HI-248	OMe	Me	0	0	OH
HI-249	OEt	Me	0	0	OH
HI-250	OPr-n	Me	0	0	OH
HI-251	OPr-i	Me	0	0	OH
HI-252	OCH₂Pr-c	Me	0	0	OH
HI-253	OCH₂C1	Me	0	0	OH
HI-254	OCHC12	Me	0	0	OH

WO 2012/002096

PCT/JP2011/062643

2018201082 14 Feb 2018 [Table 36]

Compound No.	R¹	R^z	Y	z	R⁴
HI-255	OCCI3	Me	O	0	OH
HI-256	OCH₂F	Me	O	0	OH
HI-257	OCHFj	Me	O	0	OH
III-258	OCF3	Me	O	0	OH
HI-259	Ph	Et '	O	0	OH
111'260	Ph	Pri	O	0	OH
HI-261	Ph	chf₂	O	0	OH
III-262	Ph	Ph	O	0	OH
HI-263	Ph	Me	O	s	OH
HI-264	Ph	Me	S	s	OH
HI-265	Me	Me	O	s	OH
III-266	Me	Me	s	s	OH
111-267	Ph	Me	0	0	SPh
HI-268	Ph(4-OEt)	Me	0	0	OH
HI-269	Ph(2-Ph)	Me	0	0	OH
HI-270	Ph(3-Ph)	Me	0	0	OH
HI-271	Ph(4-Ph)	Me	0	0	OH
	Me
HI-272	-aX ^Vxcf,	Me	0	0	OH
	.. ,OMe
	N=<
III-273	—/	Me	0	0	OH
	nA
	OMe
HI-274	Me	N=\	0	0	OH

		^N=\
III-275	Et		0	0	OH
III-276	H	Me	0	0	OH
HI-277	CHzC^CF	Me’	0	0	OH
	Cl Cl
HI-278		Me	0	0	OH
HI-279	/V^C1	Me	0	0	OH
HI-280	ch₂nh₂	Me	0	0	OH
ΠΙ-281	ch₂no₂	Me	0	0	OH
HI-282	ch₂nhch₃	Me	0	0	OH
III-283	CH₂N(CH₃)₂	Me	0	0	OH
IH-284	ch₂sch₂cf₃	Me	0	0	OH
HI-285	ch₂soch₂cf₃	Me	0	0	OH
HI-286	ch₂so₂ch₂cf₃	Me	0	0	OH
HI-287	ch₂oh	Me	0	0	OH
III-288	CHsOBn	Me	0	0	OH
HI-289	CH₂OCH₂Pr-c	Me	0	0	OH

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Compound No.	R¹	R²	Y	z	R⁴
III-290	CH₂OPh	Me	0	0	OH
111*291	CHsSPh	Me	0	0	OH
III-292	CHsSOPh	Me	0	0	OH
III-293	CH^C^Ph	Me	0	0	OH
III-294	CH₂CON(CH3)₂	Me	0	0	OH
HI-295	ch₂coch₃	Me	0	0	OH
III 296	CHsOCOCHa	Me	0	0	OH
III-297	ch₂on=chch₃	Me	0	0	OH
III-298	C₂H4OC₂H4SCH3	Me	0	0	OH
III-299	C₂H4OC₂H4SOCH₃	Me	0	0	OH
III-300	C₂H4OC₂H4SO2CH3	Me	0	0	OH
III 301	CH₂OCH₂CN	Me	0	0	OH
III-302	ch₂cn	Me	0	0	OH
HI-303	OCH₂CH=CH₂	Me	0	0	OH
III-304	OCH₂C = CH	Me	0	0	OH
HI-305	OPr-c	Me	0	0	OH
HI-306	^CH2O Me	Me	0	0	OH
III-307	CH₂—( 11 O-N ,Me	Me	0	0	OH
III-308	CH₂^T O-N	Me	0	0	OH
111*309	CH₂OCH₂-Y >	Me	0	0	OH
III-310	CH ₂CH ₂OCH ₂CH₂O-/^	Me	0	0	OH
HI-311	Ph	H	0	0	OH
ΠΙ-312	Ph	CH₂CH=CH₂	0	0	OH
III-313	Ph	CH₂CSCH	0	0	OH
111*314	Ph	Pr-c	0	0	OH
HI-315	Ph	CH₂CH=CF₂	0	0	OH
III-316	Ph	ch₂c=cf	0	0	OH
III-317	Ph	C2H4OCH3	0	0	OH
III-318	Ph	C2H4OC2H5	0	0	OH
III-319	Ph	CH(Me)OEt	0	0	OH
III-320	Ph	CH₂OPrc	0	0	OH
III-321	Ph	CH(OCH3)₂	0	0	OH
III-322	Ph	CH2PI1	0	0	OH
III-323	Ph		0	0	OH

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Compound No.	R¹	R²	Y	z	R⁴
III-324	Ph	—o	O	0	OH
III-325	Ph	Me	0	0	NH₂
III-326	Ph	Me	0	0	Cl
III-327	Ph	Me	0	0	CN
HI-328	Ph	Me	0	0	NCS
HI-329	Ph	Me	0	0	NCO
HI-330	Ph	Me	0	0	OCO₂H
HI-331	Ph	Me	0	0	OCO2CH3
HI-332	Ph	Me	0	0	0C0₂CH₂Ph
III-333	Ph	Me	0	0	OMe
HI-334	Ph	Me	o	0	OEt
HI-335	Ph	Me	o	0	OPr
HI-336	Ph	Me	0	0	OCH₂CH=CH₂
ΠΙ-337	Ph	Me	0	0	OCHzC^CH
HI-338	Ph	Me	o	0	OPr-c
III 339	Ph	Me	0	0	OBuc
HI-340	Ph	Me	0	0	OPenc
HI-341	Ph	Me	0	0	OHex-c
HI-342	Ph	Me	0	0	OCH₂CN
III-343	Ph	Me	0	0	OCH₂Pr-c
HI-344	Ph	Me	0	0	OCOCH3
III-345	Ph	Me	0	0	OCOCCI3
111*346	Ph	Me	o	0	OCOCH=CH₂
HI-347	Ph	Me	o	0	ococh=cf₂
III-348	Ph	Me	o	0	OCOCHzC^CH
III-349	Ph	Me	0	0	OCOCHzCSCF
HI-350	Ph	Me	o	0	OCH₂CO₂CH₃
HI-351	Ph	Me	0	0	OPh
HI-352	Ph	Me	0	0	OCH₂Ph
HI-353	Ph	Me	0	0	OCOPh
HI-354	Ph	Me	0	0	OCOCHjPh
III-355	Ph	Me	0	0	OCH₂COPh
HI-356	Ph	Me	0	0	OSO2CH2CF3
III-357	Ph	Me	0	0	OSO₂CH₂Ph
HI-358	Ph	Me	o	0	sch₃
III-359	Ph	Me	o	0	SOCH₃
III-360	Ph	Me	0	0	SO₂CH₃
HI-361	Ph	Me	0	0	SCHzCFs
III-362	Ph	Me	o	0	soch₂cf₃
HI-363	Ph	Me	0	0	SO2CH2CF3
HI-364	Ph	Me	o	0	sch₂ch=ch₂
HI-365	Ph	Me	0	0	soch₂ch=ch₂
HI-366	Ph	Me	0	0	so₂ch₂ch=ch₂

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Compound No.	R¹	R²	Y	z	R⁴
HI-367	Ph	Me	0	0	SCH₂CH=CH
HI-368	Ph	Me	0	0	SOCHzCH^CH
III-369	Ph	Me	0	0	SO2CH₂CH=CH
III-370	Ph	Me	0	0	SCH₂Ph
III-371	Ph	Me	0	0	SOPh
III-372	Ph	Me	0	0	SOCH₂Ph
III-373	Ph	Me	0	0	SO₂Ph
HI-374	Ph	Me	0	0	SO₂CH₂Ph
HI-375	Ph	Me	0	0	NHCHa
III-376	Ph	Me	0	0	N(CH₂)₂
HI-377	Ph	Me	0	0	NHCOCHs
III-378	Ph	Me	0	0	OCH₂CH₂^fA N=/
III-379	Ph	Me	0	0	Al
HI-380	Ph	Me	0	0	A —
HI-381	Ph	Me	0	0
HI-382	Ph	Me	0	0	—
HI-383	Ph	Me	0	0	₀-q

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	OH o 0
	^A] T\|i	-n'^r1
	^Α-αΛ %
	Me
Compound No.	R¹	Ai	A2	a₃
VI-1	Ph	C(CH3)₂	co	C(CH3)₂
VI-2	Ph	CHCHs	ch₂	ch₂
VI-3	Ph	ch₂	CHCHs	ch₂
VI-4	Ph	CHCH3	CHCH3	CHCHs
VI-5	Ph	C(CH3)₂	ch₂	CH₂
VI-6	Ph	ch₂	c(ch₃)₂	ch₂
VI-7	Ph	chch₃	ch₂	C(CH3)₂
VI-8	Ph	chch₃	ch₂.	CHCHs
VI-9	Ph	chch₃	chch₃	ch₂
VI-10	Ph	nch₃	co	ch₂
VI-11	Ph	C(CH3)₂	C(CHs)2	c(ch₃)₂
VI-12	Ph	C(CHs)₂	s	C(CH3)₂
VI 13	Ph	CiCHsla	so	C(CHs)₂
VI-14	Ph	C(CHs)2	so₂	C(CHs)₂
VI-15	Ph	C(CH3)₂	0	C(CH₃)₂
VI-16	Ph	C(CH3)₂	nch₃	C(CH₃)₂
VI-17	Me	C(CH3)₂	co	C(CH₃)₂
VI-18	Me	chch₃	ch₂	ch₂
VI-19	Me	ch₂	CHCH₃	ch₂
VI-20	Me	CHCHs	CHCHs	CHCHs
VI-21	Me	C(CH3)₂	ch₂	ch₂
VI-22	Me	ch₂	C(CHs)₂	ch₂
VI-23	Me	CHCHs	ch₂	C(CH3)₂
VI-24	Me	chch₃	ch₂	chch₃
VI-25	Me	CHCHs	CHCHs	ch₂
VI-26	Me	nch₃	CO	ch₂
VI-27	Me	C(CH3)₂	C(CH₃)₂	C(CH3)₂
VI-28	Me	C(CHs)₂	s	C(CH3)₂
VI-29	Me	C(CHs)2	so	C(CHs)₂
VI-30	Me	C(CHg)₂	so₂	C(CH3)₂
VI-31	Me	C(CHg>_Z	0	C(CHs)₂
VI-32	Me	C(CHs)₂	NCH_S	C(CH3)₂
VI-33	//—Me N-^	C(CHs)₂	co	C(CHs)₂
VI-34	—ζ p—Me N-^	CHCH₃	ch₂	ch₂

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Compound No.	R¹	A_x	A2	A3
VI-35	—ζ \~Me N~^	ch₂	CHCH₃	ch₂
VI-36	-ζ /—Me	chch₃	chch₃	chch₃
VI-37	—ζ /—Me N-^	C(CH3)₂	ch₂	ch₂
VI-38	/—Me	ch₂	C(CH3)₂	ch₂
VI-39	~ζ /—Me N-^	chch₃	ch₂	C(CH3)₂
VI-40	—G /—Me N-²⁷	chch₃	ch₂	chch₃
VI-41	~4 /—Me N—	chch₃	chch₃	ch₂
VI-42	-ζ. /—Me N-^	nch₃	co	ch₂
VI-43	-ζ /—Me	C(CH3)₂	C(CH3)₂	C(CH3)₂
VI-44	’ zA-Me N-^	C(CH3)₂	s	C(CHs)₂
VI-45	—ζ /—Me N—	C(CH3)₂	so	C(CH3)₂
VI-46	/—Me N—	C(CH3)₂	so₂	C(CH3)₂
VI-47	~4 /—Me n-7	C(CH3)₂	0	C(CH3)₂
VI-48	-4 /~Me	C(CH3)₂	nch₃	C(CH3)₂
VI-49	Ph(4-OMe)	C(CH3)₂	co	C(CH3)₂
VI-50	Ph(4-OMe)	chch₃	ch₂	ch₂
VI-51	Ph(4-0Me)	ch₂	chch₃	ch₂
VI-52	Ph(4-OMe)	CHCHs	CHCHs	CHCHs
VI-53	Ph(4OMe)	C(CH3)₂	CH₂	ch₂
VI-54	Ph(4-OMe)	ch₂	C(CH3)₂	ch₂
VI-55	Ph(4-OMe)	chch₃	ch₂	C(CH3)₂
VI-56	Ph(4-OMe)	chch₃	ch₂	chch₃
VI-57	Ph(4-OMe)	chch₃	chch₃	ch₂

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Compound No.	R¹	Ai	A2	A3
VI-58	Ph(4-OMe)	nch₃	co	ch₂
VI-59	Ph(4-OMe)	C(CH3)₂	C(CHg)₂	C(CHg)₂
VI-60	Ph(4-OMe)	C(CH3)₂	S	C(CHg)s
VI-61	Ph(4-OMe)	C(CH3)₂	SO	C(CHg)₂
VI-62	Ph(4OMe)	C(CH3)₂	so₂	C(CHg)₂
VI-63	Ph(4-OMe)	C(CH3)₂	0	C(CHg)₂
VI-64	Ph(4-OMe)	C(CHg)₂	NCHg	C(CHg)₂
VI-65	Ph(2,4-M_e2)	C(CH3)₂	CO	C(CHg)₂
VI-66	Ph(2,4-M_e2)	CHCHg	CH₂	CH₂
VI-67	Ph(2,4-Me2)	CH₂	CHCHg	ch₂
VI-68	Ph(2,4-Me2)	CHCHg	CHCHg	CHCHg
VI-69	Ph(2,4’Me₂)	C(CH3)₂	ch₂	CH₂
VI-70	Ph(2,4-Me2)	ch₂	C(CHg)₂	ch₂
VI-71	Ph(2,4-Me2)	CHCHg	ch₂	C(CHg)₂
VI-72	Ph(2,4-M_e2)	CHCHg	ch₂	CHCHg
VI-73	Ph(2,4-M_e2)	CHCHg	CHCHg	CH₂
VI-74	Ph(2,4'Me₂)	NCHg	CO	ch₂
VI-75	Ph(2,4-Me₂)	C(CHg)₂	C(CHg)₂	C(CHg)₂
VI-76	Ph(2,4’Me₂)	C(CHg)₂	s	C(CHg)₂
VI-77	Ph(2,4-Me₂)	C(CHg)₂ ...	so	C(CHg)₂
VI-78	Ph(2,4-Me₂)	C(CHg)₂	SO₂	C(CHg)₂
VI-79	Ph(2,4-M_e2)	C(CHg)₂	O	C(CHg)₂
VI-80	Ph(2,4-Me₂) Me	C(CH3)₂	NCHg	C(CHg)₂
VI-81	~V° _zMe	C(CHg)₂	CO	C(CHg)₂
VI-82	~v° _zMe	CHCHg	CH₂	CH₂
VI-83	V? Me	CH₂	CHCHg	ch₂
VI-84	_zMe	CHCHg	CHCHg	CHCHg
VI-85	_zMe	C(CHg)₂	ch₂	CH₂
VI-86	V? _zMe	ch₂	C(CHg)₂	ch₂
VI-87	N'⁰_ _zMe	CHCHg	CH₂	C(CHg)₂
VI-88		CHCHg	ch₂	CHCHg

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Compound No.	R¹	Aj	A2	a₃
VI-89	- Me	CHCH3	CHCH3	ch₂
VI-90	v° Me	nch₃	co	ch₂
VI-91	Me	C(CH3)₂	C(CHg)₂	C(CHs)₂
VI-92		C(CH3)₂	S	C(CH3)₂
VI-93	Me	C(CH3)₂	SO	C(CH3)₂
VI-94	Me	C(CH3)₂	so₂	C(CH3)₂
VI-95	Me	C(CH3)₂	0	0(0113)2
VI-96	Me '%Γθ	C(CHs)₂	nch₃	C(CH3)₂
VI-97	Ph(3,4,5-(OMe)3)	C(CH3)₂	co	C(CH3)₂

Preferred examples of the triazine derivative represented by Formula 1 of the invention or salt thereof include the followings.

A in Formula 1 is preferably A-l, A-3, or A-5, and more preferably A-l or A-3.

In A-l, Ai is preferably [XJ, A2 is preferably [X₃] or [X4], and A3 is preferably [X9].

In [Xi], R⁵ and R⁶ are preferably a hydrogen atom or a C]-C₆ alkyl group. In [X3], R⁸ and R⁹ are preferably a hydrogen atom or a Ci-Cg alkyl group. In [X9], R³⁵ and R³⁶ are preferably a hydrogen atom or a Ci-Ce alkyl group. Further, according to the preferred example of the invention, R⁵ in [Xi] and R³⁵ in [X9] bind to each other via a C1-C5 alkylene chain, preferably an ethylene chain, to form a ring.

In A-3, R²⁰ is preferably a Ci-Ce alkyl group and R²¹ is preferably a hydrogen atom or a Ci-Cg alkyl group.

In A-l and A-3, R⁴ is preferably a hydroxyl group, an O'M⁺(M⁺represents an alkali metal cation or an ammonium cation), or a C1-C10 alkylsulfonyloxy group.

In Formula 1, Y is preferably an oxygen atom.

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In Formula 1, R¹ is preferably a group selected from a group consisting of a C1-C12 alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₅-C₆cycloalkenyl group; a Ci-Cg haloalkyl group; a Ci-Cg halolalkenyl group; a Cj-Cg alkoxy Cj-Cg alkyl group; a Ci-Cg alkylthio Ci-Cg alkyl group; a C_rCg alkylsulfinyl Ci-Cg alkyl group; a Ci-C₆ alkylsulfonyl Ci-Cg alkyl group; a Ci-Cg alkoxycarbonyl Cj-Cg alkyl group; a phenyl group which may be substituted with a substituent group selected from Substituent group a; a phenyl Cj-Cg alkyl group which may be substituted with a substituent group selected from Substituent group a; and a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with one substituent group selected from Substituent group a or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group a, and when the heterocyclic group contains a sulfur atom, it may be oxidized to be present as sulfoxide or sulfone).

In Formula 1, R² is preferably a group selected from a group consisting of a Cj-Cg alkyl group; a Ci-Cg haloalkyl group; a phenyl group which may be substituted with a substituent group selected from Substituent group a; and a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with one substituent group selected from Substituent group a or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group a).

The triazine derivative compounds represented by Formula 1, i.e., the compounds of the invention, and their salts can be produced according to various methods. Representative examples of the production method are given below, but the invention is not limited to them.

The compound represented by following Formula la, which is one of the compounds of the invention, can be produced according to the method with the reaction scheme shown below. [Chem. 7]

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[la] (in the formula, R¹, R², Ai, A₂, A3, Y and Z have the same definitions as above and Q........

represents a leaving group like a halogen atom, an alkylcarbonyloxy group, an alkoxycarbonyloxy group, a haloalkylcarbonyloxy group, a haloalkoxycarbonyloxy group, a benzoyloxy group, a pyridyl group, and an imidazolyl group).

(Process 1)

By reacting the compound of Formula 3 and the compound of Formula 4a in a solvent in the presence of a base, the enolester compound of Formula 5a and/or Formula 5b can be produced.

Herein, the use amount of Formula 4a can be appropriately selected from the range of 0.5 to

10 mol per 1 mol of Formula 3. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base which can be used for the present process include organic amines like triethylamine, pyridine, 4-dimethylaminopyridine, Ν,Ν-dimethylaniline, and

1,8-diazabicyclo [5.4.0]undec-7-ene (DBU); metal carbonates like sodium carbonate, potassium carbonate, magnesium carbonate, and calcium carbonate; metal hydrogen carbonates like sodium hydrogen carbonate and potassium hydrogen carbonate; metal carboxylate salts represented by metal acetate salts like sodium acetate, potassium acetate, calcium acetate, and magnesium

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PCT/JP2011/062643 acetate; metal alkoxides like sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium methoxide, and potassium tertiary butoxide; metal hydroxides like sodium hydroxide, potassium hydroxide, calcium hydroxide, and magnesium hydroxide, and; metal hydrides like lithium hydride, sodium hydride, potassium hydride, and calcium hydride. The use amount of the base is appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula 3. Preferably, it is from 1.0 to 1.2 mol.

The solvent that can be used for the present process can be any solvent if it does not inhibit the progress of the reaction. Solvents including nitriles like acetonitrile; ethers like diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, monoglyme, and diglyme; halogenated hydrocarbons like dichloroethane, chloroform, carbon tetrachloride, and tetrachloroethane; aromatic hydrocarbons like benzene, chlorobenzene, nitrobenzene, and toluene; amides like Ν,Ν-dimethylformamide and Ν,Ν-dimethylacetamide; imidazolinones like l,3-dimethyl-2-imidazolinone, and; sulfur compounds like dimethyl sulfoxide can be used. Further, their mixture solvent can be also used.

The reaction temperature may be selected from the range of from -20°C to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0°C to 100°C. By using a phase transfer catalyst like quaternary ammonium salt, the reaction can be carried out in a two-phase system.

The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 5a and/or Formula 5b, which is the target compound of the reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

(Process 2)

Compound of Formula 5a and/or Formula 5b can be also produced by reacting the compound of Formula 3 and the compound of Formula 4b with a dehydrating condensing agent in a solvent, in the presence or absence of a base.

The use amount of Formula 4b that is used for the present process can be appropriately selected from the range of 0.5 to lOmolper 1 mol of Formula 3. Preferably, it is from 1.0 to 1.2

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Examples of the dehydrating condensing agent include dicyclohexyl carbodiimide (DCC),

N-(3-dimethylaminopropyl)-N’-ehtylcarbodiimide (EDC or WSC), N,N-carbonyldiimidazole,

2-chloro-l,3-dimethylimidazolium chloride, and 2-chloro-l-pyridinium iodide.

Examples of the base and the solvent which can be used for the present process include those described above for Process 1.

The reaction temperature may be selected from the range of from -20°C to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0°C to 100°C.

The compound of Formula 5 a and/or Formula 5b, which is the target compound of the reaction, can be separated and purified in the same manner as Process 1.

(Process 3)

Compound of Formula la can be produced by reacting the compound of Formula 5a and/or Formula 5b produced by Process 1 or Process 2 with a cyano compound in the presence of a base.

Examples of the base which can be used for the present process include those described above for Process 1. The use amount of the base can be appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula 5a and Formula 5b. Preferably, it is from 1.0 to 1.2 mol.

Examples of the cyano compound which can be used for the present process include potassium cyanide, sodium cyanide, acetone cyanohydrin, hydrogen cyanide, and a polymer supported with hydrogen cyanide. The use amount of the cyano compound can be appropriately selected from the range of 0.01 to 1.0 mol per 1 mol of Formula 5a and Formula 5b. Preferably, it is from 0.05 to 0.2 mol.

For the present process, a small amount of a phase transfer catalyst like crown ether can be also used.

Examples of the solvent which can be used for the present process include those described above for Process 1. The reaction temperature is selected from the range of from -20°C to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from

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0°C to 100°C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Further, according to the present process, compound of Formula la can be produced while using Formula 5a and/or Formula 5b produced by Process 1 or Process 2 without any separation.

(Process 4)

Compound of Formula la can be also produced by reacting the compound of Formula 3 and the compound of Formula 4c in the presence of a base or a Lewis acid.

The use amount of Formula 4c that is used for the present process can be appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula 3. Preferably, it is from 1.0 to 1.2 mol.

Examples of the Lewis acid include zinc chloride and aluminum chloride.

Examples of the base which can be used for the present process include those described above for Process 1. The use amount of the base that can be used for the present process can be appropriately selected from the range of 0.5 to lOmolper 1 mol of Formula 3. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present process include those described above for Process 1.

The reaction temperature is selected from the range of from -20°C to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0°C to 100°C.

After the completion of the reaction, compound of Formula la, which is produced according to Process 3 or Process 4, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

With regard to Formula la produced by Production method 1, the hydroxyl group in the cyclohexane ring can be converted to other substituent group according to the method with the following reaction scheme.

[Chem. 8]

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(in the formula, R¹, R², Ai, Az, A3, Y and Z each have the same definitions as above, R^4arepresents an amino group, a cyano group, an isothiocyanate group, an isocyanate group, a hydroxycarbonyloxy group, a Cj-Cg alkoxycarbonyloxy group, a benzyloxycarbonyloxy group which may be substituted with a substituent group selected from Substituent group a, a Cj-Cg alkoxy group, a Cz-Cg alkenyloxy group, a Cz-Cg alkynyloxy group, a C3-Cg cycloalkyloxy group, a cyanomethyleneoxy group, a C₃-Cg cycloalkyl Ci-Cg alkyloxy group, a Cj-Cg alkylcarbonyloxy group, a Ci-Cg haloalkylcarbonyloxy group, a Cz-Cg alkenylcarbonyloxy group, a Cz-Cg halolalkenylcarbonyloxy group, a Cz-Cg alkynylcarbonyloxy group, a Cz-Cg halolalkynylcarbonyloxy group, a Cj-Cg alkoxycarbonyl Ci-Cg alkoxy group, a phenyloxy group which may be substituted with a substituent group selected from Substituent group a, a benzyloxy group which may be substituted with a substituent group selected from Substituent group a, a phenylcarbonyloxy group which may be substituted with a substituent group selected from Substituent group a, a benzylcarbonyloxy group which may be substituted with a substituent group selected from Substituent group a, a phenylcarbonyl Ci-Cg alkyloxy group which may be substituted with a substituent group selected from Substituent group a, a Cj-Cio alkylsulfonyloxy group, a phenylsulfonyloxy group which may be substituted with a substituent group selected from Substituent group a, a benzylsulfonyloxy group which may be substituted with a substituent group selected from Substituent group a, a Ci-Cjg alkylthio group, a C1-C10 alkylsulfinyl group, a C1-C10 alkylsulfonyl group, a Cj-Cg haloalkylthio group, a Ci-Cg haloalkylsulfinyl group, a Ci-Cg haloalkylsulfonyl group, a Cz-Cg alkenylthio group, a Cz-Cg alkenylsulfinyl group, a Cz-Cg alkenylsulfonyl group, a Cz-Cg alkynylthio group, a Cz-Cg alkynylsulfinyl group, a Cz-Cg alkynylsulfonyl group, a phenylthio group which may be substituted with a substituent group selected from Substituent group a, a benzylthio group which may be substituted with a substituent group selected from Substituent group a, a phenylsulfinyl group which may be substituted with a substituent group selected from Substituent group a, a

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PCT/JP2011/062643 benzylsulfinyl group which may be substituted with a substituent group selected from Substituent group a, a phenylsulfonyl group which may be substituted with a substituent group selected from Substituent group a, a benzylsulfonyl group which may be substituted with a substituent group selected from Substituent group a, a Ci-Cio alkylamino group, a di(Ci-Cio alkyl)amino group, a Cj-Cg alkoxycarbonyl amino group, a Cj-Cg alkoxy group substituted with a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group a or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group a], a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group a or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group a], or a heterocyclic oxy group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group a or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group a], and X represents a halogen atom).

Specifically, the compound of Formula lb can be produced by reacting the compound of Formula la and a halogenating agent, and Formula lc can be produced by reacting the compound of Formula lb and a nucleophilic reagent in the presence of a base.

Examples of the halogenating agent that can be used for preparation of the compound of Formula lb from the compound of Formula la include thionyl chloride, thionyl bromide, phosphorus oxy chloride, phosphorus oxy bromide, phenyltrimethyl ammonium tribromide, and Meldrum’s acid tribromide. The use amount of the halogenating agent can be appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula la. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present process include those described above for Process 1 of Production method 1.

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The reaction temperature may be selected from the range of from -20°C to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0°C to

100°C.

Examples of the nucleophilic reagent for the process for obtaining Formula 1 c from Formula lb, which is a compound represented by the formula R^4a-H, include alcohols like methanol, ethanol, and benzyl alcohol; mercaptans like methyl mercaptan and ethyl mercaptan; amines like ammonia, methyl amine, and ethyl amine; phenols like p-cresol and phenol; thiophenols like p-chlorothiophenol; a Cj-Cg alkyl acids like acetic acid, and benzoic acids. The use amount of the nucleophilic reagent can be appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula lb. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base which can be used for the present process include those described above for Process 1 of Production method 1.

After the completion of the reaction, the compound of Formula 1c, which is produced according to this method, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

Compound of Formula 1c can be also produced by the method with the following reaction scheme.

[Chem. 9]

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electrophilic reagent

-

[1c] (in the formula, R¹, R², Ai, A2, A3, Y and Z each have the same definitions as above, R^4arepresents a hydroxycarbonyl group, a C|-Cg alkoxycarbonyl group, a benzyloxycarbonyl group which may be substituted with a substituent group selected from Substituent group a, a Ci-Cg alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a cyanomethylene group, a C₃-C₆ cycloalkyl Ci-C₆ alkyl group, a Ci-C₆ alkylcarbonyl group, a C1-C10 alkylthiocarbonyl group, a Ci-Cg haloalkylcarbonyl group, a C2-C6 alkenylcarbonyl group, a C2-C6 halolalkenylcarbonyl group, a C2-C6 alkynylcarbonyl group, a C2-C6 halolalkynylcarbonyl group, a Ci-C₆ alkoxycarbonyl Ci-C₆ alkyl group, a C1-C10 alkylsulfonyl group, a phenyl group which may be substituted with a substituent group selected from Substituent group a, a benzyl group which may be substituted with a substituent group selected from Substituent group a, a phenylcarbonyl group which may be substituted with a substituent group selected from Substituent group a, a benzylcarbonyl group which may be substituted with a substituent group selected from Substituent group a, a phenylsulfonyl group which may be substituted with a substituent group selected from Substituent group a, a phenylcarbonyl Ci-Cg alkyl group which may be substituted with a substituent group selected from Substituent group a, or a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group a or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group a]).

Specifically, the compound of Formula lc can be produced by reacting the compound of Formula la and an electrophilic reagent in a solvent in the presence or absence of a base.

The electrophilic reagent indicates a compound represented by the formula R^4b-L_a (L_arepresents a leaving group), and examples thereof include Ci-Cg alkyl halide like methyl iodide

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PCT/JP2011/062643 and propyl chloride; benzyl halide like benzyl bromide; Ci-Cg alkylcarbonyl halide like acetyl chloride and propionyl chloride; benzoyl halide like benzoyl chloride; C₂-Cg alkenylcarbonyl halide like methacryl chloride and crotonyl chloride; C₂-Cg alkynylcarbonyl halide like 4-pentynoyl chloride; Ci-Cg alkyl sulfonyl halide like methane sulfonyl chloride and ethane sulfonyl chloride; benzene sulfonyl halide like benzene sulfonyl chloride and p-toluene sulfonyl chloride; and di C|-Cg alkyl sulfate ester like dimethyl sulfate and diethyl sulfate. The use amount of the electrophilic reagent can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula la. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base which can be used for the present process include those described above for Process 1 of Production method 1. The use amount of the base can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula la. Preferably, it is from 1.0 to 1.2 mol.

After the completion of the reaction, the compound of Formula lc, which is a target compound of this process, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

Formula lc of the invention has many tautomers shown below, and they are all included in the invention.

[Chem.10]

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Compound of Formula Id can be also produced by the method with the following reaction scheme.

[Chem. 11]

(in the formula, R¹, R², R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, Y and Z each have the same definitions as

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2018201082 14 Feb 2018 above and Q represents a leaving group like a halogen atom, alkylcarbonyloxy group, an alkoxycarbonyloxy group, a haloalkylcarbonyloxy group, a haloalkoxycarbonyloxy group, a benzoyloxy group, a pyridyl group, and an imidazolyl group, as described above).

Specifically, compound of Formula Id can be produced by reacting the compound of

Formula 6a and the compound of Formula 4a in a solvent, in the presence of a Lewis acid.

The use amount of Formula 4a can be appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula 6a. Preferably, it is from 1.0 to 1.2 mol.

Examples of the Lewis acid that can be used include organo lithium compounds like methyl lithium, ethyl lithium, n-butyl lithium, sec-butyl lithium, tert-butyl lithium, and benzyl lithium;

Grignard’s reagent like methyl magnesium iodide and ethyl magnesium bromide; metal compounds like lithium, potassium and sodium; organo copper compounds produced from Grignard’s reagent or organometallic compound and monovalent copper salt; alkali metal amides like lithium diisopropyl amide (LDA), and; organic amines like triethylamine, pyridine, 4-dimethylaminopyridine, Ν,Ν-dimethylaniline, and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

n-Butyl lithium and lithium diisopropyl amide (LDA) are particularly preferable. The use amount of Lewis acid can be appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula 5a. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present process include those described above for Process 1 of Production method 1. Diethyl ether and tetrahydrofuran are particularly 20 preferable. The reaction temperature is selected from the range of from -20°C to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0°C to 100°C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula Id, i.e., the target compound 25 of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

Formula Id of the invention has many tautomers shown below, and they are all included in the invention.

[Chem. 12]

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Production method 5>

Compound of Formula le can be also produced by the method with the following reaction scheme.

[Chem. 13]

• I Ο Oft 01 (in the formula, R , R , R , R , Y and Z each have the same definitions as above and Q represents a leaving group like a halogen atom, alkylcarbonyloxy group, an alkoxycarbonyloxy 10 group, a haloalkylcarbonyloxy group, a haloalkoxycarbonyloxy group, a benzoyloxy group, a pyridyl group, and an imidazolyl group, as described above).

Specifically, the compound of Formula 5c can be produced by reacting the compound of Formula 6 and the compound of Formula 4a in a solvent in the presence of a base, and the

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PCT/JP2011/062643 compound of Formula 1 e can be produced by reacting the compound of Formula 5c and a cyano compound in the presence of a base.

In the above reaction, use amount of Formula 4a for preparing Formula 5c from Formula 6 can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 6. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base and solvent that can be used include those described above for Process 1 of Production method 1. The reaction temperature is selected from the range of from -20°C to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0°C to 100°C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Examples of the cyano compound which can be used for the reaction above for obtaining Formula le from Formula 5c include potassium cyanide, sodium cyanide, acetone cyanohydrin, hydrogen cyanide, and a polymer supported with hydrogen cyanide. The use amount of the cyano compound can be appropriately selected from the range of 0.01 to 1.0 mol per 1 mol of Formula 6. Preferably, it is 0.05 to 0.2 mol.

Examples of the base that can be used include those described above for Process 1 of Production method 1. The use amount of the base can be appropriately selected from the range of 0.1 to 1.0 mol per 1 mol of Formula 6. Preferably, it is 1.0 to 1.2 mol.

After the completion of the reaction, the compound of Formula le, i.e., the target compound of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

Formula le of the invention has many tautomers shown below, and they are all included in the invention.

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Compound of Formula Ig in which the substituent group in the pyrazole ring is modified can be also produced from the compound of Formula 1 e by the method with the following reaction scheme.

[Chem. 15]

R²¹

O

R¹

------>- N

N _R 2 2a η Z nucleophilic J»_o '₂ reagent ^{π n} (in the formula, R¹, R², R²⁰, R²¹, Y and Z each have the same definitions as above, R^22arepresents an amino group, a cyano group, an isothiocyanate group, an isocyanate group, a hydroxycarbonyloxy group, a Cj-Ce alkoxycarbonyloxy group, a benzyloxycarbonyloxy group which may be substituted with a substituent group selected from Substituent group a, a Ci-Ce alkoxy group, a Cj-Cg alkenyloxy group, a Cj-Cg alkynyloxy group, a C₃-Cg cycloalkyloxy group, a cyanomethyleneoxy group, a C₃-Cg cycloalkyl Ci-Cg alkyloxy group, a Ci-Cg alkylcarbonyloxy

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2018201082 14 Feb 2018 group, a Ci-Q haloalkylcarbonyloxy group, a C2-C6 alkenylcarbonyloxy group, a C2-C6 halolalkenylcarbonyloxy group, a C2-C6 alkynylcarbonyloxy group, a C2-C6 halolalkynylcarbonyloxy group, a Cj-Ce alkoxycarbonyl Ci-Cg alkoxy group, a phenyloxy group which may be substituted with a substituent group selected from Substituent group a. a benzyloxy group which may be substituted with a substituent group selected from Substituent group a, a phenylcarbonyloxy group which may be substituted with a substituent group selected from Substituent group a, a benzylcarbonyloxy group which may be substituted with a substituent group selected from Substituent group a, a phenylcarbonyl Ci-Q alkyloxy group which may be substituted with a substituent group selected from Substituent group a, a C1-C10 alkylsulfonyloxy group, a phenylsulfonyloxy group which may be substituted with a substituent group selected from Substituent group a, a benzylsulfonyloxy group which may be substituted with a substituent group selected from Substituent group a, a C1-C10 alkylthio group, a C1-C10 alkylsulfinyl group, a C1-C10 alkylsulfonyl group, a Ci-C^ haloalkylthio group, a Ci-Cg haloalkylsulfinyl group, a Ci~C₆ haloalkylsulfonyl group, a C2-C6 alkenylthio group, a C2-C6 alkenylsulfmyl group, a Ci-Cg alkenylsulfonyl group, a Ci-Cg alkynylthio group, a Ci-Cg alkynylsulfinyl group, a C2-C6 alkynylsulfonyl group, a phenylthio group which may be substituted with a substituent group selected from Substituent group a, a benzylthio group which may be substituted with a substituent group selected from Substituent group a, a phenylsulfinyl group which may be substituted with a substituent group selected from Substituent group a, a benzylsulfinyl group which may be substituted with a substituent group selected from Substituent group a, a phenylsulfonyl group which may be substituted with a substituent group selected from Substituent group a, a benzylsulfonyl group which may be substituted with a substituent group selected from Substituent group a, a C1-C10 alkylamino group, a di(Ci-Cio alkyl)amino group, a Ci-Cg alkoxycarbonyl amino group, a Ci-Cg alkoxy group substituted with a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group a or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group a], a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or

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PCT/JP2011/062643 different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group a or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group a], or a heterocyclic oxy group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group a or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group a], and X represents a halogen atom).

Specifically, the compound of Formula If can be produced by reacting the compound of Formula le and a halogenating agent and Formula Ig can be produced by reacting it with a nucleophilic reagent.

Examples of the halogenating agent that can be used for the process of producing the compound of Formula If from the compound of Formula le include thionyl chloride, thionyl bromide, phosphorus oxychloride, phosphorus oxybromide, phenyltrimethyl ammonium tribromide, and Meldrum’s acid tribromide.

The use amount of the halogenating agent can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula le. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present process include those described above for Process 1 of Production method 1. The reaction temperature is selected from the range of from -20°C to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0°C to 100°C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

The nucleophilic reagent for the process for obtaining Formula Ig from Formula If is, for example, a compound represented by the formula R^22a-H, and examples thereof include alcohols like methanol, ethanol, and benzyl alcohol; mercaptans like methyl mercaptan and ethyl mercaptan; amines like ammonia, methyl amine, and ethyl amine; phenols like p-cresol and phenol; thiophenols like p-chlorothiophenol; Ci-Cg alkyl acids like acetic acid, and benzoic acids. The use amount of the nucleophilic reagent can be appropriately selected from the range of 0.1 to

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PCT/JP2011/062643 mol per 1 mol of Formula 1 f. Preferably, it is from 1.0 to 1.2 mol.

After the completion of the reaction, the compound of Formula Ig, i.e., the target compound of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

Production method 7>

Compound of Formula lg can be also produced by the method with the following reaction scheme.

[Chem. 16]

[1e] [1g] (in the formula, R¹, R², R²⁰, R²¹, Y and Z each have the same definitions as above, R^22brepresents a hydroxycarbonyl group, a Cj-Cg alkoxycarbonyl group, a benzyloxycarbonyl group which may be substituted with a substituent group selected from Substituent group a, a Ci-Cg alkyl group, a C2-C6 alkenyl group, a Cj-Cg alkynyl group, a C₃-Cg cycloalkyl group, a cyanomethylene group, a C3-C6 cycloalkyl Ci-Cg alkyl group, a Cj-Cg alkylcarbonyl group, a C1-C10 alkylthiocarbonyl group, a C]-Cg haloalkylcarbonyl group, a Cz-Cg alkenylcarbonyl group, a Cz-Cg halolalkenylcarbonyl group, a C2-C6 alkynylcarbonyl group, a C2-C6 halolalkynylcarbonyl group, a Ci-C₆ alkoxycarbonyl Ci-Cg alkyl group, a C1-C10 alkydsulfonyl group, a phenyl group which may be substituted with a substituent group selected from Substituent group a, a benzyl group which may be substituted with a substituent group selected from Substituent group a, a phenylcarbonyl group which may be substituted with a substituent

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WO 2012/002096 104 PCT/JP2011/062643 group selected from Substituent group a, a benzylcarbonyl group which may be substituted with a substituent group selected from Substituent group a, a phenylsulfonyl group which may be substituted with a substituent group selected from Substituent group a, a phenylcarbonyl Ci-Cg alkyl group which may be substituted with a substituent group selected from Substituent group a, or a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group a or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group a]).

Specifically, the compound of Formula Ig can be produced by reacting the compound of Formula le and an electrophilic reagent in a solvent, in the presence or absence of a base.

The electrophilic reagent that can be used indicates a compound represented by the formula R^22b-L_a (L_a represents a leaving group), and examples thereof include Ci-CL alkyl halide like methyl iodide and propyl chloride; benzyl halide like benzyl bromide; Ci-C₆ alkylcarbonyl halide like acetyl chloride and propionyl chloride; benzoyl halide like benzoyl chloride; C₂-Cg alkenylcarbonyl halide like methacryl chloride and crotonyl chloride; C₂-C₆ alkynylcarbonyl halide like 4-pentinoyl chloride; Ci-Cg alkyl sulfonyl halide methane sulfonyl chloride and ethane sulfonyl chloride; benzene sulfonyl halide like benzene sulfonyl chloride and p-toluene sulfonyl chloride; and di Cj-Cg alkyl sulfate ester like dimethyl sulfate and diethyl sulfate. The use amount of the electrophilic reagent can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula le. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base and the solvent which can be used for the present process include those described above for Process 1 of Production method 1.

The use amount of the base can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 1 e. Preferably, it is from 1.0 to 1.2 mol.

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Production method 8>

Compound of Formula lh can be also produced by the method with the following reaction scheme.

[Chem. 17]

[71 [fid] ft h] (in the formula, R¹, R², R²⁴, R²⁵, Y and Z each have the same definitions as above and Q represents a leaving group like a halogen atom, alkylcarbonyloxy group, an alkoxycarbonyloxy group, a haloalkylcarbonyloxy group, a haloalkoxycarbonyloxy group, a benzoyloxy group, a pyridyl group, and an imidazolyl group, as described above).

Specifically, the compound of Formula 5d can be produced by reacting the compound of Formula 7 and the compound of Formula 4a in a solvent, in the presence of a base, and the compound of Formula lh can be produced by reacting the compound of Formula 5d and a cyano compound in the presence of a base.

In the above reaction, use amount of Formula 4a for preparing Formula 5d from Formula 7 can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 7. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base that can be used include those described above for Process 1 of Production method 1. Use amount of the base can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 7. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used include those described above for Process 1 of Production method 1.

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Examples of the cyano compound which can be used for the reaction above for obtaining Formula Ih from Formula 5d include potassium cyanide, sodium cyanide, acetone cyanohydrin, hydrogen cyanide, and a polymer supported with hydrogen cyanide. The use amount of the cyano compound can be appropriately selected from the range of 0.01 to 1.0 mol per 1 mol of Formula 5d. Preferably, it is 0.05 to 0.2 mol.

Examples of the base that can be used include those described above for Process 1 of Production method 1. The use amount of the base can be appropriately selected from the range ofO.l to l.Omolper 1 mol ofFormula5d. Preferably, it is l.Oto 1.2 mol.

The reaction temperature is selected from the range of from -20°C to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0°C to 100°C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula Ih, i.e., the target compound of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

Formula Ih of the invention has many tautomers shown below, and they are all included in the invention.

[Chem. 18]

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Production method 9>

Compound of Formula li can be produced by the method with the following reaction scheme.

[Chem. 19]

acid

(Process 1)

(Process 2)

(Process 4) honh₂ -hci

(Process 5) honh₂-hci

(in the formula, R¹, R², R²⁴, Y and Z each have the same definitions as above, R²⁵ represents a Cj-Cg alkoxycarbonyl group, R²⁶ represents an alkoxy group, a haloalkoxy group, a cycloalkoxy group, or a dimethylamino group, and R²⁷ represents an alkyl group or a benzyl group).

(Process 1)

In this process, Formula 8a can be prepared by reacting Formula Ih and acid with or without using a solvent.

Examples of the acid that can be used for the present process include sulfonic acids like p-toluene sulfonic acid. Use amount of the acid can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula Ih. Preferably, it is from 1.0 to 1.2 mol.

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PCT/JP2011/062643 (Process 2)

By reacting Formula 8a and an ortho formic acid ester compound in N,N-dimethylacetamide dimethyl acetal compound or acetic anhydride, Formula 8b can be obtained. Use amount of Ν,Ν-dimethylacetamide dimethyl acetal and ortho formic acid ester can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 8a. Preferably, it is from 1.0 to 3.0 mol.

The reaction temperature is selected from the range of from -20°C to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0°C to 150°C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

(Process 3)

Formula 8c can be obtained by reacting Formula 8a and carbon disulfide, and without isolation, adding with alkyl halide like methyl iodide or benzyl halide like benzyl bromide. Use amount of carbon disulfide can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 8a. Preferably, it is from 1.0 to 1.2 mol. Use amount of the halide can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 8a. Preferably, it is 2.0 to 2.4 mol. Examples of the solvent that can be used for the present process include those described above for Process 1 of Production method 1.

(Process 4 & Process 5)

Formula li can be obtained by reacting Formula 8b or Formula 8c obtained from Process 2 or Process 3 above and hydroxylamine chloride in a solvent.

Use amount of hydroxylamine chloride can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 8b or Formula 8c. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from -20°C to the boiling point of an

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2018201082 14 Feb 2018 inert solvent used. Preferably, the reaction is carried out in the range of from 0°C to 100°C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula li, i.e., the target compound 5 of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

Hereinbelow, a method of producing synthetic intermediates of the compounds of the invention is given.

Production method 10>

Compound of Formula 3b can be produced by the method with the following reaction scheme.

[Chem. 20]

COOEt (Route b)

NHzNR^!CONH₂[15]

COOEt

RjNHNHj -----a[9] / , / m'nco / [14]

OOEt

COOEt (Route a)

R²

[io] ^COOEt

H [16]

COOEt plating agent [11a] r’nco ,

NHjNHj HjO -------NHjNHCONHR (Route c)

OOEt

COOEt (Routed)

R^NHNHj r'nCZ or [11] \ r'nHCOjR³⁰base\ base

^R 08] [12]

R’NCO [11a] . .

-----fc· NHjNRCONHR alkylating ^Atase

OOEt

COOEt

Μ [17b] (in the formula, R^], R², Y and Z each have the same definitions as above, R³⁰ represents a phenyl group or an alkyl group, and M¹ represents sodium, potassium or trimethylsilyl).

(Route a)

Specifically, compound of Formula 10 can be obtained by reacting the compound of

Formula 9 and diethyl ketomalonate. In addition, compound of Formula 13a can be obtained by reacting the compound of Formula 10 and the compound of Formula 11 or the compound of

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Formula 12 in the presence of a base.

Use amount of diethyl ketomalonate for the process of producing Formula 10 from Formula 9 can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 9. Preferably, it is from 1.0 to 1.2 mol.

Use amount of the compound of Formula 11 or the compound of Formula 12 for the process of producing Formula 13a from Formula 10 can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 10. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base that can be used for the present process include those described above for Process 1 of Production method 1. Use amount of the base can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 10. Preferably, it is from 1.0 to 1.2 mol.

(Route b)

Specifically, compound of Formula 15 can be obtained by reacting the compound of Formula 9 and the compound of Formula 14. In addition, compound of Formula 16 can be obtained by reacting the compound of Formula 15 and diethyl ketomalonate. In addition, compound of Formula 13a can be obtained by reacting the compound of Formula 16 and an alkylating agent in the presence of a base.

Use amount of the compound of Formula 14 for the process of producing Formula 15 from

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Formula 9 can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 9. Preferably, it is from 1.0 to 1.2 mol.

Use amount of diethyl ketomalonate for the process of producing Formula 16 from Formula can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 15. Preferably, it is from 1.0 to 1.2 mol.

Use amount of the alkylating agent for the process of producing Formula 13a from Formula can be appropriately selected from the range of 1.0 to 3.0 mol per 1 mol of Formula 16. Preferably, it is from 1.0 to 1.5 mol.

Examples of the alkylating agent that can be used include alkyl sulfates like dimethyl sulfate and diethyl sulfate; alkyl halides like methyl iodide, ethyl iodide, benzyl chloride, benzyl bromide, propargyl bromide, ethyl bromoacetate, and chloroacetonitrile, and; sulfonic acid esters like ethoxyethyl p-toluene sulfonate and cyclopentyhnethane sulfonate.

Examples of the base that can be used for the present process include those described above for Process 1 of Production method 1. Use amount of the base can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 16. Preferably, it is from 1.0 to 1.2 mol.

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(Route c)

Specifically, compound of Formula 17a can be obtained by reacting the compound of Formula Ila and hydrazine hydrate. In addition, compound of Formula 18 can be obtained by reacting the compound of Formula 17 and diethyl ketomalonate. In addition, compound of Formula 13a can be obtained by reacting the compound of Formula 18 and an alkylating agent in the presence of a base.

Use amount of hydrazine hydrate for the process of producing Formula 17a from Formula Ila can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 9. Preferably, it is from 1.0 to 1.2 mol.

Use amount of diethyl ketomalonate for the process of producing Formula 18 from Formula 17a can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 17a. Preferably, it is from 1.0 to 1.2 mol.

Use amount of the alkylating agent for the process of producing Formula 13a from Formula

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Preferably, it is from 1.0 to 1.5 mol.

Examples of the alkylating agent that can be used include alkyl sulfates like dimethyl sulfate and diethyl sulfate; alkyl halides like methyl iodide, ethyl iodide, benzyl chloride, benzyl bromide, propargyl bromide, ethyl bromoacetate, and chloroacetonitrile, and; sulfonic acid esters like ethoxyethyl p-toluene sulfonate and cyclopentylmethane sulfonate.

Examples of the base that can be used for the present process include those described above for Process 1 of Production method 1. Use amount of the base can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 18. Preferably, it is from 1.0 to 1.2 mol.

(Route d)

Specifically, compound of Formula 17b can be obtained by reacting the compound of Formula Ila and the compound of Formula 9. In addition, compound of Formula 13a can be obtained by reacting the compound of Formula 17b and diethyl ketomalonate, using an acid or a base depending on the condition.

Use amount of the compound of Formula 9 for the process of producing Formula 17b from Formula 11 a can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 9. Preferably, it is from 1.0 to 1.2 mol.

Examples of the acid that can be used include organic acids represented by organic sulfonic acid like p-toluene sulfonic acid, methane sulfonic acid, and benzene sulfonic acid; hydrogen halide acids represented by hydrochloric acid and hydrogen bromic acid, and; inorganic acids like sulfuric acid and phosphoric acid. These acids can be used either singly or in combination of two or more.

Examples of the base that can be used for the present process include those described above

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The reaction temperature is selected from the range of from -20°C to the boiling point of an 5 inert solvent used. Preferably, the reaction is carried out in the range of from 0°C to 100°C.

Use amount of diethyl ketomalonate for the process of producing Formula 13a from Formula 17b can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 10 17b. Preferably, it is from 1.0 to 1.2 mol.

Examples of the acid include organic acids like p-toluene sulfonic acid.

Examples of the base include organic bases like triethylamine and l,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and inorganic bases like sodium hydride, sodium methoxide, and sodium ethoxide.

After the completion of the reaction, the compound of Formula 13a, i.e., the target compound of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

(Route e)

Specifically, compound of Formula 3b can be obtained by hydrolyzing the compound of Formula 13a.

With regard to the process of obtaining the compound of Formula 3b from the compound of Formula 13a, the production can be carried out by hydrolysis in water, organic solvent, or a mixture solvent in the presence of an acid or a base.

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Examples of the base that can be used include those described above for Process 1 of Production method 1.

Use amount of the base can be appropriately selected from the range of 0.01 to 100 mol per mol of Formula 13a. Preferably, it is 0.1 to 10 mol.

Examples of the acid that can be used include inorganic acids like hydrochloric acid, hydrobromic acid, and sulfuric acid, and organic acids like acetic acid and trifluoroacetic acid.

Use amount of the acid can be appropriately selected from the range of 1 mol to excess amount per 1 mol of Formula 13a. Preferably, it is from 1 to 100 mol.

Examples of the organic solvent that can be used include a mixture solvent of water and an organic solvent. Examples of the organic solvent include alcohols like methanol and ethanol, ether like tetrahydrofuran, ketones like acetone and methyl isobutyl ketone, amides like Ν,Ν-dimethyl formamide and Ν,Ν-dimethyl acetamide, sulfur compounds like dimethyl sulfoxide and sulfolane, acetonitrile, and their mixture.

Use amount of the solvent is 0.01 to 100 L per 1 mol of Formula 13a. Preferably, it is 0.1 tolOL.

(Route f)

Specifically, compound of Formula 13b can be obtained by reacting the compound of Formula 13a and a sulfurizing agent. In addition, the compound of Formula 3b can be obtained by hydrolyzing the compound of Formula 13b.

Use amount of the compound of the sulfurizing agent for the process of producing Formula

13b from Formula 13a can be appropriately selected from the range of 1.0 to 8.0 mol per 1 mol of

Formula 13a. Preferably, it is from 1.0 to 4.0 mol.

Examples of the sulfurizing agent that can be used include diphosphorus pentoxide and 2,4-bis(4-methoxyphenyl)-l,3,2,4-dithiadiphosphetane-2,4-disulfide.

Use amount of the compound of the sulfurizing agent can be appropriately selected from the

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With regard to the process of obtaining the compound of Formula 3b from the compound of Formula 13b, the production can be carried out by hydrolysis in water, organic solvent, or a mixture solvent in the presence of an acid or a base.

Use amount of the base can be appropriately selected from the range of 0.01 to 100 mol per 1 mol of Formula 13b. Preferably, it is 0.1 to 10 mol.

Use amount of the acid can be appropriately selected from the range of 1 mol to excess amount per 1 mol of Formula 13b. Preferably, it is from 1 to 100 mol.

Use amount of the solvent is 0.01 to 100 Lper 1 mol of Formula 13b. Preferably, it is 0.1 to 10 L.

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After the completion of the reaction, the compound of Formula 3b, i.e., the target compound of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

Compound of Formula 3a can be produced according to the method with the following reaction scheme.

[Chem. 21]

[3b] [3a] (in the formula, R¹, R², Y and Z each have the same definitions as above and X represents a chlorine or a bromine).

Specifically, Formula 3a can be produced by reacting Formula 3b and an appropriate halogenating agent with or without a solvent.

Examples of the halogenating agent that can be used include oxalyl chloride and thionyl chloride.

Use amount of the halogenating agent can be appropriately selected from the range of 0.01 to 20 mol per 1 mol of Formula 3b. Preferably, it is from 1 to 10 mol.

Examples of the solvent include halogenated hydrocarbons like dichloromethane and chloroform, ethers like diethyl ether and tetrahydrofuran, and aromatic hydrocarbons like benzene and toluene.

Use amount of the solvent is 0.01 to 100 L per 1 mol of Formula 3b. Preferably, it is 0.1 to 10 L.

After the completion of the reaction, the compound of Formula 3a, i.e., the target compound

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Examples of the production intermediates [13a] and [3b], that can be described for the Production method 10, are shown in Table 44 to Table 67.

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2018201082 14 Feb 2018 [Table 44]

0 Y
	r¹ R²
Compound No.	R¹	R²	Y	z
IV-1	Me	Me	0	0
IV-2	Et	Me	0	0
IV-3	Pr-n	Me	0	0
IV-4	Pri	Me	0	0
IV-5	Bu-n	Me	0	0
IV-6	Bu-i	Me	0	0
IV-7	Bu-s	Me	0	0
IV-8	Bu-t	Me	0	0
IV-9	Hex-n	Me	0	0
IV-10	CH₂CF₃	Me	0	0
IV-11	ch₂ch=ch₂	Me	0	0
IV-12	CH₂C(Me)=CH₂	Me	0	0
IV-13	CH₂CH₂CH=CMe₂	Me	0	0
IV-14	CH₂CEECH	Me	0	0
IV-15	ch₂cecch₃	Me	0	0
TV-16	Pr-c	Me	0	0
IV-17	Bu’C	Me	0	0
TV-18	Pen-c	Me	0	0
IV-19	Hex-c	Me	0	0
IV-20	CH₂Pr-c	Me	o	0
IV-21	CH₂Buc	Me	0	0
IV-22	CH₂Pen-c	Me	0	0
IV-23	CH₂Hex-c	Me	0	0
IV-24	CH₂CH=CC1₂	Me	0	0
IV-25	ch₂cci=chci	Me	o	0
IV-26	ch₂ch₂ch=cci₂	Me	o	0
IV-27	CH₂CH₂C(Me)=CF₂	Me	o	0
IV-28	CH₂CH₂CH₂CH₂C(Me)=CF₂	Me	o	0
IV-29	CH₂CH=CF₂	Me	o	0
IV-30	CH₂CH₂OMe	Me	0	0
IV-31	CH₂CH₂OEt	Me	0	0
IV-32	CH(Me)CH₂OMe	Me	o	0
IV-33	CH₂CH₂OCH₂CH₂OMe	Me	0	0
IV-34	CH₂CH₂OPr-n	Me	0	0
IV-35	CH₂CH₂OPr-i	Me	o	0
IV-36	CH₂CH₂OPr-c	Me	0	0

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Compound No.	R¹	R²	Y	z
IV-37	CH₂CH₂OBu-c	Me	0	0
IV-38	CH₂CH₂OPenc	Me	0	0
IV-39	CH₂CH₂OHexc	Me	0	0
IV-40	CH₂CH₂OCH₂CF₃	Me	0	0
IV-41	CH₂CH₂CH₂OMe	Me	0	0
IV-42	CH-CHMe	Me	0	0
IV-43	CH₂SMe	Me	0	0
IV-44	CH₂SPrn	Me	0	0
IV-45	CH₂CH₂SMe	Me	0	0
IV-46	CHsSOMe	Me	0	0
IV-47	CH₂SO₂Me	Me	0	0
IV-48	CH₂CH₂CH₂SMe	Me	0	0
IV-49	CH₂CH₂CH₂SO₂Me	Me	0	0
IV-50	Ph	Me	0	0
IV-51	Ph(2-Cl)	Me	0	0
IV-52	Ph(3-C0	Me	0	0
IV-53	Ph(4-CD	Me	0	0
IV-54	Ph(2-F)	Me	0	0
IV-55	Ph(3-F)	Me	0	0
IV-56	Ph(4-F)	Me	0	0
IV-57	Ph(2-Me)	Me	0	0
IV-58	Ph(3-Me)	Me	0	0
IV-59	Ph(4-Me)	Me	0	0
IV-60	Ph(2-OMe)	Me	0	0
IV-61	Ph(3-OMe)	Me	0	0
IV-62	Ph(4-OMe)	Me	0	0
IV-63	Ph(2-CF3)	Me	0	0
IV-64	Phfe-CFg)	Me	0	0
IV-65	Ph(4-CFs)	Me	0	0
IV-66	Ph(2-NO₂)	Me	0	0
IV 67	Phte-NOji)	Me	0	0
IV-68	Ph(4-NO₂)	Me	0	0
IV-69	Ph(2-0CF;j)	Me	0	0
IV-70	Ph(3-OCF_S)	Me	0	0
IV-71	Ph(4-OCF3)	Me	0	0
IV-72	Ph(2-CN)	Me	0	0
IV-73	Ph(3-CN)	Me	0	0
IV-74	Ph(4-CN)	Me	0	0
IV-75	PhiSA-F^	Me	0	0

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Compound No.	R¹	R²	Y	z
IV-76	Ph(3,5-F2)	Me	0	0
IV-77	Ph(2,3-F2)	Me	0	0
IV-78	Ph(2,4-F2)	Me	0	0
IV-79	Ph(2,5-F₂)	Me	0	0
IV-80	Ph(2,6-F2)	Me	0	0
IV-81	Ph(3,4-Cl₂)	Me	0	0
IV-82	Ph(3,5-C12)	Me	0	0
TV-83	Ph(2,3-Cl₂)	Me	0	0
TV-84	Ph(2,4-C12)	Me	0	0
IV-85	Ph(2,5-C12)	Me	0	0
IV-86	Ph(2,6Cl₂)	Me	0	0
IV-87	Ph(3,4-M_e2)	Me	0	0
IV-88	ΡΙιίΒ,δ-Με^	Me	0	0
IV-89	Ph(2,3-Me₂)	Me	0	0
IV-90	Ph(2,4-Me₂)	Me	0	0
IV-91	Ph(2,5-Me₂)	Me	0	0
IV-92	Ph(2,6-Me₂)	Me	0	0
IV-93	Ph(3,4-(OMe)₂)	Me	0	0
IV-94	Ph(3,5-(OMe)2)	Me	0	0
IV-95	Ph(2,3 (OMe)s)	Me	0	0
. IV-96	Ph(2,4(OMe)2)	Me	0	0
TV-97	Ph(2,5-(OMe)₂)	Me	0	0
TV-98	Ph(2,6-(OMe)2)	Me	0	0
TV-99	Ph(3-F-4-OMe)	Me	0	0
IV-100	Ph(3-F-5-OMe)	Me	0	0
IV-101	Ph(2-F-3-OMe)	Me	0	0
IV-102	Ph(2-F-4-OMe)	Me	0	0
IV-103	Ph(2-F-5-OMe)	Me	0	0
IV-104	Ph(2-F-6-OMe)	Me	0	0
IV-105	Ph(3-F-4-Me)	Me	0	0
IV-106	Ph(3-F-5-Me)	Me	0	0
IV-107	Ph(2-F-3-Me)	Me	0	0
IV-108	Ph(2-F-4-Me)	Me	0	0
IV-109	Ph(2-F-5-Me)	Me	0	0
IV-110	Ph(2-F-6-Me)	Me	0	0
IV-111	Ph(3-OMe-4-F)	Me	0	0
TV-112	Ph(2OMe-3F)	Me	0	0
IV113	Ph(2-OMe-4-F)	Me	0	0
IV-114	Ph(2-OMe-5F)	Me	0	0

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Compound No.	R¹	R²	Y	z
IV-115	Ph(3Me-4-F)	Me	0	0
IV116	Ph(2Me-3-F)	Me	0	0
IV-117	Ph(2-Me-4-F)	Me	0	0
IV118	Ph(2-Me-5-F)	Me	0	0
IV-119	Ph(3Cl-4-OMe)	Me	0	0
IV-120	Ph(3Cl-5-OMe)	Me	0	0
IV-121	Ph(2-Cl-3-OMe)	Me	0	0
IV-122	Ph(2-Cl-4-OMe)	Me	0	0
IV-123	Ph(2-Cl-5-OMe)	Me	0	0
IV-124	Ph(2-Cl-6-OMe)	Me	0	0
IV-125	Ph(3-Cl-4-Me)	Me	0	0
IV-126	Ph(3-Cl-5-Me)	Me	0	0
IV-127	Ph(2-Cl-3-Me)	Me	0	0
IV-128	Ph(2-Cl-4-Me)	Me	0	0
IV-129	Ph(2-Cl-5-Me)	Me	0	0
IV-130	Ph(2-Cl-6-Me)	Me	0	0
IV-131	Ph(3-OMe-4-Cl)	Me	0	0
IV-132	Ph(2-OMe-3-Cl)	Me	0	0
IV-133	Ph(2-OMe-4-Cl)	Me	0	0
IV-134	Ph(2OMe-5CD	Me	0	0
IV-135	Ph(3Me-4-Cl)	Me	0	0
IV-136	Ph(2-Me-3-CD	Me	0	0
IV-137	Ph(2-Me-4-Cl)	Me	0	0
IV-138	Ph(2-Me-5-Cl)	Me	0	0
IV-139	Ph(3F-4-CD	Me	0	0
IV-140	Ph(3-F-5-Cl)	Me	0	0
IV-141	Ph(2-F-3-Cl)	Me	0	0
IV-142	Ph(2-F-4-Cl)	Me	0	0
IV-143	Ph(2-F-5-Cl)	Me	0	0
IV-144	Ph(2-F-6-CD	Me	0	0
IV-145	Ph(3Cl-4F)	Me	0	0
IV-146	Ph(2-Cl-3-F)	Me	0	0
IV-147	Ph(2-Cl-4-F)	Me	0	0
IV-148	Ph(2-Cl-5-F)	Me	0	o
IV-149	Ph(3-Me-4-OMe)	Me	0	0
IV150	Ph(3-Me-5-OMe)	Me	0	0
IV-151	Ph(2-Me-3-OMe)	Me	0	0
IV-152	Ph(2-Me-4-OMe)	Me	0	0
IV153	Ph(2Me-5OMe)	Me	0	0

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Compound No.	R¹	R²	Y	z
IV-154	Ph(2-Me-6-OMe)	Me	O	0
IV-155	Ph(3-OMe-4-Me)	Me	0	0
IV-156	Ph(2-OMe-3-Me)	Me	0	0
IV-157	Ph(2-OMe-4-Me)	Me	0	0
IV-158	Ph(2-OMe-5Me)	Me	0	0
IV-159	Ph(3-CN-4-OMe)	Me	0	0
IV-160	Ph(3-OMe-4-CN)	Me	0	0
IV-161	Ph(3-Me-4-CN)	Me	0	0
IV-162	Ph(3-CN-4-Me)	Me	0	0
IV-163	Ph(3-NO₂-4-OMe)	Me	0	0
IV-164	Ph(3OMe-4-NO2)	Me	0	0
IV-165	Ph(3-Me-4-NO2)	Me	0	0
IV-166	Ph(3-NO₂-4-Me)	Me	0	0
IV-16 7	Ph(3,5F₂-5OMe)	Me	0	0
IV-168	Ph(3,5-F₂-5-Me)	Me	0	0
IV-169	Ph(3,4,5-(OMe)3)	Me	0	0
IV-170	cr	Me	0	0
IV-171		Me	0	0
IV-172	V	Me	0	0
IV-173		Me	0	0
IV-174		Me	0	0
IV-175		Me	0	0
IV-176		Me	0	0
IV-177		Me	0	0

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Compound No.	R¹	R²	Y	z
IV-178		Me	O	0

IV-179		Me	0	0
IV-180		Me	0	0
	N
IV-181		Me	0	0
IV-182	—ζ y)—Me	Me	0	0
	N—^f
IV-183	——OMe	Me	0	0
IV-184	-ΓΎ-f	Me	0	0
IV-185		Me	0	0
IV-186	—C>-^Br	Me	0	0
IV-187		Me	0	0
IV-188		Me	0	0
	_,Me
IV-189	v°	Me	0	0
IV-190		Me	o	0
IV-191	Ti	Me	o	0

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Compound No.	R¹	R²	Y	z
IV-205	CH₂Ph	Me	0	0
IV-206	CH₂CH₂Ph	Me	0	0
IV-207	CH₂CH₂CH₂Ph	Me	0	0
IV-208	CH₂CH=CHPh	Me	0	0
IV-209	CH₂C = CPh	Me	0	0
IV-210	CH₂CH=NOMe	Me	0	0
IV-211	CH₂CH=NOEt	Me	0	0
IV-212	CH₂CH=NOPr-n	Me	0	0
IV-213	CH₂CH=NOPh	Me	0	0
IV-214	CH₂CH(OMe)₂	Me	0	0
IV-215	CH₂CHO	Me	0	0
IV-216	nh₂	Me	0	0
IV-217	NHMe	Me	0	0
IV-218	NHEt	Me	0	0
IV-219	NHPr-n	Me	0	0
IV-220	NHPr-i	Me	0	0
IV-221	NHBu-n	Me	0	0
IV-222	NHBui	Me	0	0
IV-223	NHBu-s	Me	0	0
IV-224	NHCH₂Prc	Me	0	0
IV-225	NHPen-n	Me	0	0
IV-226	NHHex-n	Me	0	0
IV-227	NHCH₂CH₂CH₂C1	Me	0	0
IV-228	NHCH₂CH2CH₂F	Me	0	0
IV-229	NHCH₂CH₂OMe	Me	0	0
IV-230	NMe₂	Me	0	0
IV-231	NEt2	Me	0	0
IV-232	N(Pr-n)₂	Me	0	0
IV-233	N(Bu-n)₂	Me	0	0
IV-234	N(Me)Et	Me	0	0
IV-235	N(Me)CH₂CH₂OMe	Me	0	0
IV-236	NHPh	Me	0	0
IV-237	NHCH₂Ph	Me	0	0
IV-238	N=CMe₂	Me	0	0
IV-239	N=CEt₂	Me	0	0
IV-240	N=CHNMe₂	Me	0	0
IV-241	NHC(=O)Me	Me	0	0
IV-242	N[C(=O)Me]₂	Me	0	0
IV-243	NHC(=O)OMe	Me	0	0
IV-244	N[C(=O)OMe]₂	Me	0	0
IV-245	NHSO₂Me	Me	0	0

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Compound No.	R¹	R²	Y	z
IV-246	NHSO₂Ph	Me	0	0
IV-247	NHSO₂CH₂Ph	Me	0	0
IV-248	OMe	Me	0	0
IV-249	OEt	Me	0	0
IV-250	OPr-n	Me	0	0
IV-251	OPri	Me	0	0
IV-252	OCH₂Pr-c	Me	0	0
IV-253	OCH₂C1	Me	0	0
IV-254	OCHCI2	Me	0	0
IV-255	OCClg	Me	0	0
IV-256	OCH₂F	Me	0	0
IV-257	OCHF₂	Me	0	0
IV-258	ocf₃	Me	0	0
IV-259	Ph	Et	0	0
IV-260	Ph	Pr-i	0	0
IV-261	Ph	chf₂	0	0
IV-262	Ph	Ph	0	0
IV-263	Ph	Me	0	s
IV-264	Ph	Me	s	s
IV-265	Me	Me	0	s
IV-266	Me	Me	s	s
IV-267	Ph	Me	0	0
IV-268	Ph(4-0Et)	Me	0	0
IV-269	Ph(2-Ph)	Me	0	0
IV-270	Ph(3-Ph)	Me	0	0
IV-271	Ph(4-Ph) Me	Me	0	0
IV-272	aX ^X>xcf₃ N-°^Me	Me	0	0
IV-273	—)	Me	0	0
IV-274	Me	“Cd ⁿ=\	0	0
IV-275	Et.	--- V V	0	0
IV-276	JO	Me	0	0

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Compound No.	R¹	R²	Y	z
IV-277	Mes^b^	Me	0	0
IV-278	A	Me	0	0
IV-279	Π	Me	0	0
IV-280	Me If 1	Me	0	0
IV-281	jQ	Me	0	0
IV-282	Ph(2-Me-4-Br)		0	0
IV-283	Ph(2-Me-4-I)	Me	0	0
IV-284	Ph(2-Me-4-CF3)	Me	0	0
IV-285	Ph(2-Me-4-OCF3)	Me	0	0
IV-286	Ph(2-Pr-i)	Me	0	0
IV-287		Me	0	0
IV-288	Ph(2-Et)	Me	0	0
IV-289	Me-^b^	Me	0	0
IV-290	A	Me	0	0
IV-291	^O^Me	Me	0	s
IV-292		Me	0	0
IV-293	[j^N	Me	0	0
IV-294	CH₂COOBu-t	Me	0	0
IV-295	(C₇H₁₄)CH₃	Me	0	0
IV-296	(c₉h₁₈)ch₃	Me	0	o
IV-297	Ph(2-F,4-Cl,5OMe)	Me	0	0
IV-298	Ph(2,3,4-(OMe)3)	Me	0	0
IV-299	Ph(3,5-Cl₂-4-OMe)	Me	0	0
IV-300	Ph(3,5-Cl₂-4-SMe)	Me	0	0

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Compound No.	R¹	R²	Y	z
IV-301	Ph(3,5-Cl₂-4-SO₂Me)	Me	0	0
IV-302	Ph(3,4,5-F3)	Me	0	0
IV-303		Me	0	0
IV-304	-•O	Me	0	0
IV-305		Me	0	0
IV-306	Bu-n	N=\	0	0
IV-30 7	CH₂CH(CH3)₂		0	0
IV-308	Ph	Pen-n	0	0
IV-309	H	Me	0	0
IV-310	CH₂C^CF Cl. Cl	Me	0	0
IV-311	a,ci	Me	0	0
IV-312	'-^Cl	Me	0	0
IV-313	ch₂nh₂	Me	0	0
IV-314	ch₂no₂	Me	0	0
IV-315	CH2NHCH3	Me	0	0
IV-316	CH₂N(CH3)₂	Me	0	0
IV-317	ch₂sch₂cf₃	Me	0	0
IV-318	CH₂SOCH₂CF_s	Me	0	0
IV-319	ch₂so₂ch₂cf₃	Me	0	0
IV-320	ch₂oh	Me	0	0
IV-321	CH₂OBn	Me	0	0
IV-322	CH₂OCH₂Pr-c	Me	0	0
IV-323	CH₂OPh	Me	0	0
IV-324	CH₂SPh	Me	0	0
IV-325	CH₂SOPh	Me	0	0
IV-326	CH₂SO₂Ph	Me	0	0
IV-327	CH₂CON(CH3)₂	Me	0	0
IV-328	ch₂coch₃	Me	0	0
IV-329	ch₂ococh₃	Me	0	0

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Compound No.	R¹	R²	Y	z
IV-330	CH₂ON=CHCH₃	Me	O	0
IV-331	C₂H₄OC₂H₄SCH3	Me	O	0
IV-332	c₂h₄oc₂h₄soch₃	Me	0	0
IV-333	C₂H₄OC₂H₄SO₂CH3	Me	0	0
IV-334	ch₂och₂cn	Me	0	0
IV-335	ch₂cn	Me	0	0
IV-336	och₂ch=ch₂	Me	0	0
IV-337	OCH₂CECH	Me	0	0
IV-338	OPrc	Me	0	0
IV-339	ch₂·/^ cr Me	Me	0	0
IV-340	CH?^-\ T b'N	Me	0	0
IV-341	0Η₂-/ν^Μθ O-N	Me	0	0
IV-342	ch₂och₂-Y >	Me	0	0
IV-343	ΟΗ₂εΗ₂ΟΰΗ₂ΟΗ₂Ο-/~Λ N=/	Me	0	0
IV-344	Ph	H	0	0
IV-345	Ph	ch₂ch=ch₂	0	0
IV-346	Ph	ch₂cech	0	0
IV-347	Ph	Pre	0	0
IV-348	Ph	ch₂ch=cf₂	0	0
IV-349	Ph	ch₂cecf	0	0
IV-350	Ph	C2H4OCH3	0	0
IV-351	Ph	C₂H₄OC₂H_s	0	0
IV-352	Ph	CH(Me)OEt	0	0
IV-353	Ph	CH₂OPr-c	0	0
IV-354	Ph	CH(OCH3)₂	0	0
IV-355	Ph	CH₂Ph	0	0
IV-356	Ph	CH=CH-Ph	0	0
IV-357	Ph	CEC-Ph	0	0

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9 y i ^'N^Z &
Compound No.	R¹	R²	Y	z
v-i	Me	Me	O	0
V-2	Et	Me	0	0
V-3	Prn	Me	0	0
V-4	Pri	Me	0	0
V-5	Bu-n	Me	0	0
V-6	Bu-i	Me	0	0
V-7	Bu-s	Me	0	0
V-8	Birt	Me	0	0
V-9	Hex-n	Me	0	0
VTO	CH₂CF₃	Me	0	0
v-u	CH₂CH=CH₂	Me	0	0
VT2	CH₂C(Me)=CH₂	Me	0	0
V-13	CH₂CH₂CH=CMe₂	Me	0	0
V14	CH₂CECH	Me	0	0
VT5	CH₂CECCH₃	Me	0	0
V-16	Pr-c	Me	0	0
V-17	Bu-c	Me	0	0
V-18	Pen-c	Me	0	0
V-19	Hex-c	Me	0	0
V-20	CH₂Pr-c	Me	0	0
V-21	CH₂Bu-c	Me	0	0
V-22	CH₂Pen-c	Me	0	0
V-23	CH₂Hex-c	Me	0	0
V-24	CH₂CH=CC1₂	Me	0	0
V-25	ch₂cci=chci	Me	0	0
V-26	ch₂ch₂ch=cci₂	Me	0	0
V-27	CH₂CH₂C(Me)=CF₂	Me	0	0
V-28	CH₂CH₂CH₂CH₂C(Me)=CF₂	Me	0	0
V-29	CH₂CH=CF₂	Me	0	0
V-30	CH₂CH₂OMe	Me	0	0
V-31	CH₂CH₂OEt	Me	0	0
V-32	CH(Me)CH₂OMe	Me	0	0
V-33	CH₂CH₂OCH₂CH₂OMe	Me	0	0
V-34	CH₂CH₂OPr-n	Me	0	0
V-35	CH₂CH₂OPr-i	Me	0	0
V-36	CH₂CH₂OPr-c	Me	0	0
V-37	CH₂CH₂OBu-c	Me	0	0
V-38	CH₂CH₂OPen-c	Me	0	0

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Compound No.	R¹	R²	Y	z
V-39	CH₂CH₂OHex-c	Me	O	0
V-40	CH₂CH₂OCH₂CF₃	Me	O	0
V-41	CH₂CH₂CH₂OMe	Me	0	0
V-42	CH=CHMe	Me	0	0
V-43	CH₂SMe	Me	0	0
V-44	CH₂SPr-n	Me	0	0
V-45	CH₂CH₂SMe	Me	0	0
V-46	CH₂SOMe	Me	0	0
V-47	CH₂SO₂Me	Me	0	0
V-48	CH2CH₂CH₂SMe	Me	0	o
V-49	CH₂CH₂CH₂SO2Me	Me	0	o
V-50	Ph	Me	0	0
V-51	Ph(2-Cl)	Me	0	0
V-52	Ph(3-Cl)	Me	0	0
V-53	Ph(4-Cl)	Me	0	0
V-54	Ph(2-F)	Me	0	0
V-55	Ph(3-F)	Me	0	0
V-56	Ph(4-F)	Me	0	o
V-57	Ph(2-Me)	Me	0	0
. V-58	Ph(3-Me)	Me	0	0
V-59	Ph(4-Me)	Me	0	0
V-60	Ph(2-OMe)	Me	0	0
V-61	Ph(3-OMe)	Me	0	0
V-62	Ph(4-OMe)	Me	0	0
V-63	Ph(2-CF₃)	Me	0	0
V-64	Ph(3-CF₃)	Me	0	o
V-65	Ph(4-CFa)	Me	0	0
V-66	Ph(2-NO2)	Me	0	0
V-67	Ph(3-NO2)	Me	0	0
V-68	Ph(4-NO2)	Me	0	0
V-69	Ph(2-0CFs)	Me	0	0
V-70	PhG-OCFs)	Me	0	0
V-71	Ph(4OCFs)	Me	0	0
V-72	Ph(2-CN)	Me	0	0
V-73	Ph(3CN)	Me	0	0
V-74	Ph(4-CN)	Me	0	0
V-75	Ph(3,4-F2)	Me	0	0
V-76	Ph(3,5-F2)	Me	0	0
V-77	Ph(2,3F₂)	Me	0	0
V-78	Ph(2,4-F₂)	Me	0	0

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Compound No.	R¹	R²	Y	z
V-79	Ph(2,5-F₂)	Me	0	0
V-80	Ph(2,6-F2)	Me	0	0
V-81	Ph(3,4-C12)	Me	0	0
V-82	Ph(3,5-C12)	Me	0	0
V-83	Ph(2,3-C12)	Me	0	0
V-84	Ph(2,4-Cl₂)	Me	0	0
V-85	Ph(2,5-C12)	Me	0	0
V-86	Ph(2,6-Cl₂)	Me	0	0
V-87	Ph(3,4-Me2)	Me	0	0
V-88	Ph(3,5-Me2)	Me	0	0
V-89	Ph(2,3-Me2)	Me	0	0
V-90	Ph(2,4-Me2)	Me	0	o
V-91	Ph(2,5‘Me2)	Me	0	0
V-92	Ph(2,6-Mea)	Me	0	0
V-93	Ph(3,4-(OMe)2)	Me	0	0
V-94	Ph(3,5-(OMe)₂)	Me	0	0
V-95	Ph(2,3-(OMe)2)	Me	0	0
V-96	Ph(2,4-(OMe)2)	Me	0	0
V-97	Ph(2,5-(OMe)s)	Me	0	0
V-98	Ph(2,6(OMe)s)	Me	0	0
V-99	Ph(3-F-4-OMe)	Me	0	0
V-100	Ph(3-F-5-OMe)	Me	0	0
V-101	Ph(2-F-3OMe)	Me	0	0
V-102	Ph(2-F-4-OMe)	Me	0	0
V-103	Ph(2-F-5-OMe)	Me	0	0
V-104	Ph(2F-6OMe)	Me	0	0
V-105	Ph(3-F-4-Me)	Me	0	0
V-106	Ph(3-F-5-Me)	Me	0	o
V-107	Ph(2-F-3-Me)	Me	0	0
V-108	Ph(2-F-4-Me)	Me	0	0
V-109	Ph(2-F-5-Me)	Me	0	0
V-110	Ph(2-F-6-Me)	Me	0	0
V-lll	Ph(3-OMe-4-F)	Me	0	0
V-112	Ph(2-OMe-3-F)	Me	0	0
V-113	Ph(2-OMe-4-F)	Me	0	0
V-114	Ph(2-OMe-5-F)	Me	0	0
V-115	Ph(3Me-4-F)	Me	0	0
V-116	Ph(2-Me-3-F)	Me	0	0
V-117	Ph(2-Me-4-F)	Me	0	0

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2018201082 14 Feb 2018 [Table 59]

Compound No.	R¹	R²	Y	z
V-118	Ph(2-Me-5-F)	Me	0	0
V-119	Ph(3Cl-4OMe)	Me	0	0
V-120	Ph(3Cl-5-OMe)	Me	0	0
V-121	Ph(2-Cl-3-OMe)	Me	0	0
V-122	Ph(2-Cl-4-OMe)	Me	0	0
V-123	Ph(2-Cl-5OMe)	Me	0	0
V-124	Ph(2-Cl-6-OMe)	Me	0	0
V-125	Ph(3-Cl-4-Me)	Me	0	0
V-126	Ph(3-Cl-5-Me)	Me	0	0
V-127	Ph(2-Cl-3-Me)	Me	0	0
V-128	Ph(2Cl-4-Me)	Me	0	0
V-129	Ph(2-Cl-5-Me)	Me	0	0
V-130	Ph(2-Cl-6-Me)	Me	0	0
V-131	Ph(3-OMe-4-CD	Me	0	0
V-132	Ph(2-OMe-3-CD	Me	0	0
V-133	Ph(2-OMe-4-Cl)	Me	0	0
V-134	Ph(2-OMe-5-Cl)	Me	0	0
V-135	Ph(3-Me-4-Cl)	Me	0	0
V-136	Ph(2-Me-3-Cl)	Me	0	0
VT37	Ph(2Me-4CD	Me	0	0
V-138	Ph(2-Me-5-CD	Me	0	0
V-139	Ph(3-F-4-Cl)	Me	0	0
V-140	Ph(3-F-5-Cl)	Me	0	0
V-141	Ph(2-F-3-Cl)	Me	0	0
V-142	Ph(2-F-4-Cl)	Me	0	0
V-143	Ph(2F-5-Cl)	Me	0	0
V-144	Ph(2-F-6-Cl)	Me	0	0
V-145	Ph(3-Cl-4-F)	Me	0	0
V-146	Ph(2Cl-3-F)	Me	0	0
V-147	Ph(2-Cl-4-F)	Me	0	0
V-148	Ph(2Cl-5-F)	Me	0	0
V-149	Ph(3-Me-4-OMe)	Me	0	0
V-150	Ph(3-Me-5-OMe)	Me	0	0
V-151	Ph(2-Me-3OMe)	Me	0	0
V-152	Ph(2-Me-4-OMe)	Me	0	0
V-153	Ph(2-Me-5-OMe)	Me	0	0
V-154	Ph(2-Me-6-OMe)	Me	0	0
V-155	Ph(3-OMe-4-Me)	Me	0	0
V-156	Ph(2-OMe-3Me)	Me	0	0

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2018201082 14 Feb 2018 [Table 60]

Compound No.	R¹	R²	Y	z
V-157	Ph(2-OMe‘4-Me)	Me	O	0
VI58	Ph(2-OMe-5-Me)	Me	O	0
V-159	Ph(3-CN-4OMe)	Me	O	0
V-160	Ph(3OMe-4-CN)	Me	O	0
V-161	Ph(3-Me-4-CN)	Me	O	0
V-162	Ph(3-CN-4-Me)	Me	O	0
V-163	Ph(3-NO₂-4OMe)	Me	O	0
V-164	Ph(3OMe-4-NO₂)	Me	0	0
V-165	Ph(3-Me-4-NO₂)	Me	0	0
V-166	Ph(3-NO₂-4-Me)	Me	0	0
V-167	Ph(3,5-F₂-4-OMe)	Me	0	0
V-168	Ph(3,5-F₂-4-Me)	Me	0	0
V-169	Ph(3,4,5-(OMe)3)	Me	0	0
V-170		Me	0	0
	Tr
V-171		Me	0	0
V-172		Me	0	0

V-173	Ά /) \	Me	0	0
	0-⁷
V-174	HQ-0	Me	0	0
V-175		Me	0	0
V-176	-CH	Me	0	0

V-177		Me	0	0

V-178		Me	0	0
	Me θ

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2018201082 14 Feb 2018 [Table 61]

Compound No.	R¹	R²	Y	z
V-179	—	Me	a 0	0
V-180	—4 & N	Me	0	0
V-181	-O	Me	0	0
V-182	—'b—Me N—	Me	0	0
V-183	—^~OMe	Me	0	0
V-184	— N-^	Me	0	0
V-185	N-^	Me	0	0
V-186		Me	0	0
V-187	—{^-^CF3	Me	0	0
V-188		Me	0	0
	_^Me
V-189	V	Me	0	0
V-190	A	Me	0	0
V-191	.Me -ff	Me	0	0
V-192		Me	0	0

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2018201082 14 Feb 2018 [Table 62]

Compound No.	R¹	R²	Y	z
		^Me
V-193			Me	O	0
V-194			Me	O	0
	Sm·'
		-Me
V-195	Ν		Me	0	0

V-196	—<^S1 N^	^Me	Me	0	0
	s—,	^.Me
V-197	• -Λ 1 Ν'		Me	0	0
	s~
V-198		s	Me	0	0
V199	s-	-Me	Me	0	0
V-200	___/	Γ	Me	0	0
V-201		'Me	Me	0	0
V-202	—N	o	Me	0	0
V-203	—N	^Ss	Me	0	0
V-204	—N	'so₂	Me	0	0
V-205	CH₂Ph		Me	0	0
V-206	CH₂CH₂Ph		Me	0	0
V-207	CH₂CH₂CH₂Ph		Me	0	0
V-208	CH2CH-CHPI1		Me	0	0
V-209	CH₂C = CPh		Me	0	0
V-210	CH₂CH=NOMe		Me	0	0

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2018201082 14 Feb 2018 [Table 63]

Compound No.	R¹	R²	Y	z
V-211	CH₂CH=NOEt	Me	0	0
V-212	CH₂CH=NOPr-n	Me	0	0
V-213	CH₂CH-NOPh	Me	0	0
V-214	CH₂CH(OMe)₂	Me	0	0
V-215	CH₂CHO	Me	0	0
V-216	NH₂	Me	0	0
V-217	NHMe	Me	0	0
V-218	NHEt	Me	0	0
V-219	NHPrn	Me	0	0
V-220	NHPr-i	Me	0	0
V-221	NHBu-n	Me	0	0
V-222	NHBu-i	Me	0	0
V-223	NHBu-s	Me	0	0
V-224	NHCHaPr-c	Me	0	0
V-225	NHPeirn	Me	0	0
V-226	NHHex-n	Me	0	0
V-227	NHCH₂CH₂CH₂C1	Me	0	0
V-228	nhch₂ch₂ch₂f	Me	0	0
V-229	NHCHsCHsOMe	Me	0	0
V-230	NMe₂	Me	0	0
V-231	NEtg	Me	0	0
V-232	N(Pr-n)₂	Me	0	0
V-233	N(Bu-n)₂	Me	0	0
V-234	N(Me)Et	Me	0	0
V-235	N(Me)CH₂CH₂OMe	Me	0	0
V-236	NHPh	Me	0	0
V-237	NHCH₂Ph	Me	0	0
V-238	N=CMe₂	Me	0	0
V-239	N=CEt₂	Me	0	0
V-240	N-CHNMe₂	Me	0	0
V-241	NHC(=O)Me	Me	0	0
V‘242	N[C(=O)Me]₂	Me	0	0
V-243	NHC(=O)OMe	Me	0	0
V-244	N[C(=O)OMe]₂	Me	0	0
V-245	NHSOzMe	Me	0	0
V-246	NHSO₂Ph	Me	0	0
V‘247	NHSO₂CH₂Ph	Me	0	0
V-248	OMe	Me	0	0
V-249	OEt	Me	0	0
V-250	OPr-n	Me	0	0
V-251	OPr-i	Me	0	0
V-252	OCH₂Pr-c	Me	0	0
V-253	OCH₂C1	Me	0	0
V-254	ochci₂	Me	0	0

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2018201082 14 Feb 2018 [Table 64]

Compound No.	R¹	R²	Y	z
V-255	OCC1₃	Me	0	0
V-256	OCH2F	Me	0	0
V-257	ochf₂	Me	0	0
V-258	OCF₃	Me	0	0
V-259	Ph	Et	0	0
V-260	Ph	Pri	0	0
V-261	Ph	CHF₂	0	0
V-262	Ph	Ph	0	0
V-263	Ph	Me	0	s
V-264	Ph	Me	s	s
V-265	Me	Me	0	s
V-266	Me	Me	s	s
V-267	Ph	Me	0	0
V-268	Ph(40Et)	Me	0	0
V-269	Ph(2-Ph)	Me	0	0
V-270	Ph(3-Ph)	Me	0	0
V-271	Ph(4-Ph) Me	Me	0	0
V-272	aX N=<^0Me	Me	0	0
V-273	^NXOMe	Me	0	0
V-274	Me	—	0	0
V-275	Et CKJSL	—	0	0
V-276	j\| 1	Me	0	0
V-277 V-278	Me^N^ A '^^'Me	Me Me	0 0	0 0
V-279		Me	0	0

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2018201082 14 Feb 2018 [Table 65]

Compound No.	R¹	R²	Y	z
	/^Cl
V-280		Me	0	0
V-281	jl!	Me	0	0

V-282	Ph(2-Me-4-Br)	Me	0	0
V-283	Ph(2-Me-5-l)	Me	0	0
V-284	Ph(2-Me-5-CF₃)	Me	0	0
V-285	Ph(2-Me-6-OCF3)	Me	0	0
V-286	Ph(2-Pr-i)	Me	0	0
	OMe
V-287		Me	0	0
V-288	Ph(2-Et)	Me	0	0

V-289	A	Me	0	0

V-290	JQ .Me	Me	0	0
V-291	1	Me	0	s


V-292		Me	0	0
V-293		Me	0	0
V-294	CH^COOBu-t	Me	0	0
V-295	(c₇h₁₄)ch₃	Me	0	0
V-296	(C₉H₁₈)CH₃	Me	0	0
V-297	Ph(2-F,4-Cl,5-OMe)	Me	0	0
V-298	Phfc.S.WMels)	Me	0	0
V-299	Ph(3,5-Cl₂-4-OMe)	Me	0	0
V-300	Ph(3,5-Cl₂-4-SMe)	Me	0	0
V-301	Ph(3,5-Cl₂-4-SO₂Me)	Me	0	o
V-302	Ph(3,4,5-F3)	Me	0	0
V-303	—	Me	0	0

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Compound No.	R¹	R²	Y	z
V-304	-o	Me	O	0

V-305	χι	Me	O	0
V-306	Bun	—	0	0
V-307	CH₂CH(CH₃)₂		0	0
V-308	Ph	Penn	0	0
V-309	H	Me	0	0
V-310	CH₂C = CF	Me	o	0
V-311		Me	0	0
V-312	λόι	Me	0	0
V-313	ch₂nh₂	Me	0	0
V-314	ch₂no₂	Me	0	0
V-315	ch₂nhch₃	Me	0	0
V-316	CH₂N(CH3)₂	Me	0	0
V-317	ch₂sch₂cf₃	Me	0	0
V-318	ch₂soch₂cf₃	Me	0	0
V-319	ch₂so₂ch₂cf₃	Me	0	0
V-320	CHzOH	Me	0	0
V-321	CH₂OBn	Me	0	0
V-322	CH₂OCH₂Prc	Me	0	0
V-323	CH₂OPh	Me	0	0
V-324	CH₂SPh	Me	0	0
V-325	CH₂SOPh	Me	0	0
V-326	CH₂SO₂Ph	Me	0	0
V-327	CH₂CON(CH3)₂	Me	0	0
V-328	ch₂coch₃	Me	0	0
V-329	ch₂ococh₃	Me	0	0
V-330	ch₂on=chch₃	Me	0	0
V-331	c₂h₄oc₂h₄sch₃	Me	0	0
V-332	c₂h₄oc₂h₄soch₃	Me	0	0
V-333	c₂h₄oc₂h₄so₂ch₃	Me	0	0

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Compound No.	R¹	R²	Y	z
V-334	CH2OCH2CN	Me	O	0
V-335	CH2CN	Me	O	0
V-336	OCH₂CH=CH₂	Me	O	0
V-337	och₂c=ch	Me	O	0
V-338	OPr-c	Me	O	0
V-339	CH₂-<p	Me	O	0
V-340	O-N	Me	O	0
V-341	^ch^Q[^m'	Me	O	0
V-342	CH₂OCH₂-< >	Me	O	0
V-343	ch₂ch ₂och ₂ch	Me	O	0
V-344	Ph	H	O	0
V-345	Ph	ch₂ch=ch₂	O	0
V-346	Ph	ch₂c=ch	O	0
V-347	Ph	Pr-c	O	0
V-348	Ph	CH₂CH=CF₂	O	0
V-349	Ph	CHsC^CF	O	0
V-350	Ph	C2H4OCH3	O	0
V-351	Ph	C2H4OC2H.5	O	0
V-352	Ph	CH(Me)OEt	O	0
V-353	Ph	CH₂OPr-c	O	0
V-354	Ph	CH(OCHa)₂	O	0
V-355	Ph	CH₂Ph	O	0
V-356	Ph	CH=CH-Ph	O	0
V-357	Ph	CsC-Ph	O	0
V-358	Ph(3,4,5-CD	Me	O	0
V-359	N(Me)Ph N=r-^Me	Me	O	0
V-360	αΣ_μ.	Me	0	0
V-361	—(' zAMe N-^	Me	0	0
V-362	CH₂CO(Bu-t)	Me	0	0
V-363	Ph(2,3,5,6-F4)	Me	0	0
V-364	Ph[(3,5-(CF3)21	Me	0	0
V-365	CH₂C(Me)-NOMe	Me	0	0
V-366	Ph(2,4,6-Me3)	Me	0	0
V-367	Ph(2,3,4,5,6-F5)	Me	0	0
V-368	N(Et)Ph	Me	0	0
V-369	N(Pr-i)Ph	Me	0	0
V-370	N(Me)Ph(4-F)	Me	0	0
V-371	CH₂C(Me)=NOEt	Me	0	0

Compounds of the invention have an excellent herbicidal activity and some of them show

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PCT/JP2011/062643 excellent selectivity between crops and weeds and are usefill as an agrochemical composition for farmland, especially as herbicides. In other words, the compounds of the invention have a herbicidal activity for various weeds during foliage treatment, soil treatment, seed dressing treatment, soil blending treatment, soil treatment before sowing, treatment at the time of sowing, soil treatment after sowing, soil covering and blending treatment at the time of sowing, and soil treatment before and after sowing for no-tillage fanning of a field for cultivating agrohorticultural plants.

Hereinbelow, examples of the weeds are given, but the invention is not limited to them; weeds of Onagraceae family: Oenothera erythrosepala, Oenothera laciniata;

weeds of Ranunculaceae family: Ranunculus muricatus, Ranunculus sardous;

weeds of Polygonaceae family: Polygonum convolvulus, Polygonum lapathifolium, Polygonum pensylvanicum, Polygonum persicaria, Rumex crispus, Rumex obtusifolius, Poligonum cuspidatum, Polygonum pensylvanicum, Persicaria longiseta, Persicaria lapathifolia, Persicaria nepalensis;

weeds of Portulacaceae family: Portulaca oleracea;

weeds of Caryophyllaceae family: Stellaria media, Cerastium glomeratum, Stellaria alsine, Spergula arvensis, Stellaria aquatica;

weeds of Chenopodiaceae family: Chenopodium album, Kochia scoparia, Chenopodium album, Chenopodium ficifolium;

weeds of Amaranthaceae family: Amaranthus retroflexus, Amaranthus hybridus, Amaranthus palmeri, Amaranthus spinosus, Amaranthus rudis, Amaranthus albus, Amaranthus viridus, Amaranthus lividus;

weeds of Brassicaceae family: Raphanus raphanistrum, Sinapis arvensis, Capsella bursa-pastoris, Lepidium virginicum, Thlaspi arvense, Descurarinia sophia, Rorippa indica, Rorippa islandica, Sisymnrium officinale, Cardamine flexuosa, Nasturtium officinale, Draba nemorosa;

weeds of Fabaceae family: Sesbania exaltata, Cassia obtusifolia, Desmodium tortuosum, Trifolium repens, Vicia sativa, Medicago lupulina, Vicia hirsuta; Kummerowia striata, Medicago polymorpha, Vicia angustifolia, Aeschynomene indica;

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PCT/JP2011/062643 weeds of Malvaceae family: Abutilon theophrasti, Sida spinosa;

weeds of Violet family: Viola arvensis, Viola tricolor;

weeds of Rubiaceae family: Galium aparine;

weeds of Convolvulaceae family: Ipomoea hederacea, Ipomoea purpurea, Ipomoea hederacea var integriuscula, Ipomoea lacunosa, Convolvulus arvensis, Ipomoea indica, Ipomoea coccinea, Ipomoea triloba;

weeds of Lamiaceae family: Lamium purpureum, Lamium amplexicaule, Stachys arvensis;

weeds of Solanaceae family: Datura stramonium, Solanum nigrum, Physalis angulata, Solanum americanum, Solanum carolinense;

weeds of Scrophulariaceae family: Veronica persica, Veronica arvensis, Veronica hederaefolia;

weeds of Asteraceae family: Xanthium pensylvanicum, Helianthus annuus, Matricaria chamomilla, Matricaria perforata or inodora, Chrysanthemum segetum, Matricaria matricarioides, Ambrosia artemisiifolia, Ambrosia trifida, Erigeron canadensis, Artemisia princeps, Solidago altissima, Taraxacum officinale, Anthemis cotula, Breea setosa, Sonchus oleraceus, Helianthus tuberosus, Cirsium arvense, Bidens frondosa, Bidens pilosa, Centurea cyanus, Cirsium vulgare, Lactuca scariola, Rudbeckia hirta, Rudbeckia laciniata, Rudbeckia laciniata var. hortensis Bailey, Senecio vulgais, Silybum marianum, Sonchus asper, Sonchus arvensis, Salsola kali, Bidens ftondosa, Eclipta ptostrata, Bidense tipartita, Senecio madagascariensis, Coreopsis lanceolata, Rudbeckia laciniata;

weeds of Boraginaceae family: Myosotis arvensis;

weeds of Asclepiadaceae family: Asclepias syriaca;

weeds of Euphorbiaceae family: Euphorbia helioscopia, Euphorbia maculata, Acalypha australis;

weeds of Geraniaceae family: Geranium carolinianum:

weeds of Oxalidaceae family: Oxalis corymbosa;

weeds of Cucurbitaceae family: Sicyos angulatus;

weeds of Poaceae family: Echinochloa crus-galli, Setaria viridis, Setaria faberi, Digitaria sanguinalis, Eleusine indica, Poa annua, Alopecurus myosuroides, Avena fatua, Sorghum

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PCT/JP2011/062643 halepense, Agropyron repens, Bromus tectorum, Cynodone dactylon, Panicum dichotomiflorum,

Panicum texanum, Sorghum vulgare, Alopecurus geniculatus, Lolium multiflorum, Lolium rigidum, Setaria glauca, Beckmannia syzigachne;

weeds of Commelinaceae family: Commelina communis;

weeds of Equisetaceae family: Equisetum arvense;

weeds of Papaveraceae family: Papaver rhoeas;

weeds of Cyperaceae family: Cyperus iria, Cyperus rotundus, Cyperus esculentus.

Compounds of the invention do not exhibit any phytotoxicity which causes a problem in major crops like Zea mays, Triticum aestivum, Hordeum vulgare, Oryza sativa, Sorghum bicolor, Glycine max, Gossypium spp., Beta vulgaris, Arachis hypogaea, Helianthus annuus, Brassica napus, buck wheat, sugar cane, and tobacco, and horticultural crops like flowers and vegetables.

Further, the compounds of the invention are useful for effective elimination of various weeds which cause a trouble in no-tillage farming of soybean, com, and wheat, and they do not exhibit any problematic phytotoxicity to crops.

Accroding to many treatment methods like soil treatment before cultivation; soil treatment after cultivation but before or after sowing; soil treatment after harrowing but before or after sowing, or treatment before or after transplanting a seedling; treatment at the time of transplanting a seedling; desalination treatment after transplanting a seedling; and foliage treatment, the compounds of the invention can exhibit an herbicidal activity for many problematic weeds in paddy field that are described below.

Hereinbelow, examples of the weeds are given, but the invention is not limited to them: weeds of Poaceae family: Echinochloa oryzicola; Echinochloa crus-galli, Leptochloa chinensis, Isachne globosa, Paspalum distichum, Leersia sayanuka, Leersia oryzoides;

weeds of Scrophulariaceae family: Lindemia procumbens, Lindemia dubia, Dopatrium junceum, Gratiola japonica, Lindemia angustifolia, Limnophila sessiliflora;

weeds of Lythraceae family: Rotala indica, Ammannia multiflora;

weeds of Elatinacease family: Elatine triandra;

weeds of Cyperacease family: Cyperus difformis, Scirpus hotarui, Eleocharis acicularis, Cyperus serotinus, Eleocharis kuroguwai, Fimbristylis miliacea, Cyperus flaccidus, Cyperus

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PCT/JP2011/062643 globosus, Scirpus juncoides, Scirpus wallichii, Scirpus nipponicus, Fimbristylis autumnalis,

Scirpus tabemaemontani, Scirpus juncoides Rocxb., Scirpus lineolatus Franch. et Savat., Cyperus orthostachyus Franch. et Savat., Cyperus orthostachyus Franch. et Savat., Eleocharis congesta D.

Don, Scirpus planicuhnis Fr. Schm.;

weeds ofPontederiacease family: Monochoria vaginalis, Monochoria korsakowii, Heteranthera limosa;

weeds of Alismatacease family: Sagittaria pygmaea, Sagittaria trifolia, Alisma canaliculatum, Sagittaria aginashi;

weeds of Potamogetonacease family: Potamogeton distinctus;

weeds of Eruocaulacease family: Eriocaulon cinereum;

weeds of Apiaccase family: Oenanthe j avanica;

weeds of Asteracease family: Eclipta prostrata, Bidens tripartita;

weeds of Commelinacease family: Murdannia keisak;

weeds of Characease family: Chara braunii;

weeds of Lemnacease family: Spirodela polyrhiza;

Hepaticae: Ricciocarpus natans;

Zygnemataceae: Spirogyra arcla.

Further, the compounds of the invention show no phytoxicity to paddy rice according to any cultivation method including direct sowing or transplanting of paddy rice followed by cultivation.

Further, the compounds of the invention can be used for controlling a wide spectrum of weeds thriving in a lot for industrial facilities like a slope of a levee, a riverbed, a shoulder and a slope of a road, a railway site, park spaces, grand, a parking lot, an airport, a factory and a storage facility, a non-crop land like fallow fields, and vacant lots in city, which needs the weed control, or an orchard, a pasture land, a grass land, a forest land, etc.

Moreover, according to foliage treatment, water-surface application, etc., the compounds of the invention can exhibit a herbicidal activity for water weeds which occur in river, waterway, canal, reservoir, etc., wherein the water weeds include Pontederiaceae family: Eichhomia crassipes; Salvinia natans family: Azolla imbricata, Azolla japonica, Salvinia natanas; Araceae family: Pistia stratiotes; Haloragaceae family: Myriophyllum brasilensa, Myriophyllum

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PCT/JP2011/062643 verticillatum; Myriophyllum spicatum; Myriophyllum matogrossense; Azollaceae family: Azolla cristata; Scrophulariacease family: Veronica anagallis-aquatica; Amaranthaceae family: Altemanthera philoxeroides; Gymnocoronis spilanthoides; Poaceate family: Spartina anglica; Apiaceae family: Hydrocotyle ranunculoides; Hydrocharitaceae family: Hydrilla verticillata, Egeria densa; Cabpmbaceae family: Cabomba caroliniana; and Lemnaceae family: Woiffia globosa.

The agrohorticultural plants described in the invention include crops like com, rice, wheat, barley, rye, sorghum, cotton, soybean, peanuts, buck wheat, sugar beet, rapeseed, sun flower, sugar cane, and tobacco; vegetable like vegetables of Solanaceae (eggplant, tomato, bell pepper, pepper, potato, etc.), vegetables of Cucurbitaceae (cucumber, pumpkin, zucchini, water melon, melon, etc.), vegetables of Cruciferae (daikon, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.), vegetables of Compositae (burdock, crown daisy, artichoke, lettuce, etc.), vegetables of Liliaceae (scallion, onion, garlic, asparagus, etc.), vegetables of Apiaceae (carrot, parsley, celery, parsnip, etc.), vegetables of Chenopodiaceae (spinach, leaf beet, etc.), vegetables of Lamiaceae (beefsteak plant, mint, basil, etc.), vegetables like strawberry, sweet potato, yam, and taro; kernel fruits (apple, western pear, Japanese pear, Chinese quince, quince, etc.), stone fruits (peach, plum, nectarine, Japanese apricot, cherry, apricot, prune, etc.), mandarins (tangerine, orange, lemon, lime, grape fruits, etc.), nuts (chestnut, walnut, hazelnut, almond, pistachio, cashewnut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), fruits like grape, persimmon, olive, loquat, banana, coffee, date, coconut, and oil nut; trees other than fruit tree like tea, mulberry, roadside trees (ash tree, birch, American flowering dogwood, eucalyptus, gingko, lilac, maple tree, oak tree, poplar tree, redbud tree, liquidambar, sycamore, zelkova, Japanese arborvitae, Japanese fir, hemlock spruce, juniper, pine tree, spruce, yew, elm, a horse chestnut, etc.), coral, Buddist pine, cedar, Japanese cypress, croton, spindle tree, Photinia glabra, etc.; grasses like turf (turf, gold turf, etc.), Bermuda grasses (Cynodon dactylon, etc.), bentgrasses (creeping bentgrass, Agrostis alba L., Agrostis capillaries, etc.), bluegrasses (Kentucky bluegrass, Poa trivialis L., etc.), fescues (tall fescue, chewings fescue, Festuca rabra L., etc.), rye grasses (Lolium temulentum L., Lolium perenne L., etc.), orchard grass, timothy, etc.; oil crops like oil coconut, Jatropha curcas, etc.; flowers (rose,

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PCT/JP2011/062643 carnation, mum, prairie gentian, common gypsophila, gerbera, marigold, salvia, petunia, verbena, tulip, Chinese aster, Gentiana scabra var. buergeri, lily, pansy, cyclamen, orchid, lily of the valley, lavender, stock, cauliflower, primula, poincetia, gladiolus, cattleya, daisy, verbena, cymbidium, begonia, etc.); a foliage plant, etc., but the invention is not limited thereto.

The agrohorticultural plant described in the invention includes a plant given with resistance to HPPD inhibitor like Isoxaflutole, ALS inhibitor like Imazetaphyr and tifensulfuron methyl, EPSP synthase inhibitor like glifosate, glutamine synthase inhibitor like glufosinate, acetyl CoA carboxylase inhibitor like sethoxydim, PPO inhibitor like flumioxazin, and herbicides like bromoxinil, dicamba and 2,4-D according to classic breeding method or genetic recombination method.

Examples of the agrohorticultural plant given with resistance according to classic breeding include rapeseed, wheat, sun flower, rice, and com that are resistant to imidazoloinone-based ALS inhibitor like Imazetaphyr, and they are already commercially available in the name of Clearfield <trade name>.

Similarly, there is soybean resistant to sulfonylurea-based ALS inhibitor like tifensulfuron metil as produced by classic breeding method, and it is already commercially available in the trade name of STS Soybean. Similarly, examples of the agrohorticultural plant given with resistance to an acetyl CoA carboxylase inhibitor like trione-oxime based or aryloxyphenoxy propionic acid-based herbicides according to classic breeding include SR Com. The horticultural plant given with resistance to acetyl CoA carboxylase is described in Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA), Vol 87, pages 7175 to 7179 (1990), etc. Further, a mutant acetyl CoA carboxylase which is resistant to acetyl CoA carboxylase inhibitor is reported in Weed Science Vol. 53, pages 728 to 746 (2005), and by introducing a mutant gene of acetyl CoA carboxylase to a plant by genetic recombination technique or by introducing mutation for giving resistance to acetyl CoA carboxylase of crops, a plant which is resistant to an acetyl CoA carboxylase inhibitor can be produced. Further, by having site-specific amino acid substitution mutation on a gene of crops based on introduction of a nucleic acid with base substitution mutation to a plant cell as represented by chimeraplasty technique (Gura T. 1999. Repairing the Genome’s Spelling

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Mistakes. Science 285:316-318), a plant which is resistant to acetyl CoA carboxylase inhibitor/herbicides can be produced.

Examples of the agrohorticultural plant given with resistance according to genetic recombination technique include com, soybean, cotton, rapeseed, and sugar beet that are resistant to glyfosate, and they are already commercially available in the name of RoundupReady <trade name>, AgrisureGT, etc. Similarly, there are com, soybean, cotton, and rapeseed varieties that are produced to be resistant to glufosinate by genetic recombination technique, and they are already commercially available in the name of LibertyLink <trade name>, etc. Similarly, cotton having resistance to bromoxinil is also made available by genetic recombination technique and is already commercially available in the trade name of BXN.

The agrohorticultural plant includes a plant which is engineered by genetic recombination technique to synthesize a selective toxin like Baciullus spp., for example.

Examples of the insecticidal toxin expressed in a genetically engineered plant include an insecticidal protein originating from Bacillus cereus or Bacillus popilliae; δ-endotoxin originating from Bacillus thuringiensis like CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl, and Cry9C, and insecticidal proteins like VIP1, VIP2, VIP3, and VIP3A; insecticidal proteins originating from a nematode; animal-produced toxins like scorpion toxin, spider toxin, bee toxin, and insect specific neurotoxin; filamentous fungus toxin; plant lectin; agglutinin; protease like trypsin inhibitor, serine protease, patatin, cistatin, and papain inhibitor; ribosome inactivating proteins (RIP) like lysine, com-RIP, abrin, saporin, and briodin; enzymes for steroid metabolism like 3-hydroxysteroid oxidase, ecdisteroid-UDP-glycosyl transferase, and cholesterol oxidase; ecdysone inhibitor; HMG-CoA reductase; ion channel inhibitors like sodium channel inhibitor and potassium channel inhibitor; juvenile hormone esterase; natriuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; and glucanase.

Examples of the toxins expressed in a genetically engineered plant include a hybrid toxin, a partially deleted toxin, and a modified toxin of an insecticidal protein like δ-endotoxin including CrylAb, CrylAc, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl, and Cry9C, and insecticidal proteins including VIP 1, VIP2, VIP3, and VIP3A. The hybrid toxin is produced by new combination of domains having different proteins based on recombination technique. Examples

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In the modified toxin, one or more amino acids of a natural type toxin are replaced with other amino acids.

Examples of the toxins and recombinant plants capable of producing the toxins are described in EP-A-0374753, WO93/07278, WO95/34656, EP-A-0427529, EP-A-451878, and W003/052073, and the like.

The toxins contained in such recombinant plant can provide a plant with a resistance to harmful insects of Coleoptera, harmful insects of Diptera, and harmful insects of Lepidoptera.

A genetically engineered plant which contains one or more pesticidal harmful insect-resistant gene and expresses one or more toxins is known, and some are already commercially available. Examples of the genetically engineered plant include YieldGard <trade name> (com variety which expresses Cryl Ab toxin), YieldGard Rootworm <trade name> (com variety which expresses Cry3Bbl toxin), YieldGard Plus <trade name> (com variety which expresses CrylAb and Cry3Bbl toxin), Herculex I <trade name> (com variety which expresses phosphinotricine N-acetyl transferase (PAT) to give resistance to CiylFa2 toxin and glufosinate), NuCOTN33B <trade name> (cotton variety which expresses Cryl Ac toxin), Bollgard I <trade name> (cotton variety which expresses CrylAc toxin), Bollgard II <trade natne> (cotton variety which expresses CrylAc and Cry2Ab toxin), VIPCOT <trade name> (cotton variety which expresses VIP toxin), NewLeaf <trade name> (potato variety which expresses Cry3A toxin), NatureGard <trade name> Agrisure <trade natne>GT Advantage (GA21 glyfosate resistant trait), Agrisure <trade name> CB Advantage (Btll Com Borer (CB) trait), and Protecta <trade name>.

The agrohorticultural plant includes a plant which is genetically engineered to have an ability of producing an anti-pathogenic substance having selective activity.

Examples of the anti-pathogenic substance include PR proteins (PRPs, described in EP-A-0392225); ion channel inhibitors like sodium channel inhibitor and calcium channel inhibitor (KPI, KP4, KP6 toxin that are produced by virus are known); stilbene synthase; bibenzyl synthase; chitinase; glucanase; and a substance produced by a microorganism like peptide antibiotics, antibiotics having heterocycle, and a protein factor related to resistance to plant disease (referred to as plant disease resistant gene, and described in W003/000906).

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Such anti-pathogenic substances and plants genetically engineered to produce the substances are described in EP-A-03 92225, WO95/33818, and EP-A-0353191, etc.

The agrohorticultural plant includes a plant which is given with useful traits like a trait of having modified oil components or a trait for producing enhanced amount of amino acid according to genetic recombination technique. Examples thereof include VISTfVE <trade name> (low-linolenic soybean having reduced linden content) or high-lysine (high oil) com (com having enhanced amount of lysine or oil).

Further, there is also a stack variety in which multiple traits of classic herbicidal trait or herbicides-resistant gene, pesticidal insect-resistant gene, anti-pathogenic substance-producing gene, and useful traits like a trait of having modified oil components or a trait for producing enhanced amount of amino acid are combined.

The agrochemical composition of the invention contains the triazine derivative of the invention or a salt thereof, and an agriculturally acceptable carrier. The agrochemical composition of the invention may contain additive components that may be normally employed for agrochemical formulations, as needed.

Examples of the additive components include carriers such as solid carrier and liquid carrier, surface active agent, binder, tackifier, thickener, coloring agent, spreader, sticker, antifreezing agent, anticaking agent, collapsing agent, decomposition inhibitor and the like.

If necessary, an antiseptic agent, a piece of plant (soybean powder, tobacco powder, walnut powder, wheat powder, wood powder, hulls, wheat hulls, outer hulls, sawdust, pulp flock, com stalk, nut shell, fruit core chips, etc.) and the like may also be employed as additive components.

These additive components may be used alone or in combination of two or more kinds.

The above additive components will be described.

Examples of the solid carrier include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomite; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride; organic solid carriers such as synthetic silicic acid, synthetic silicate, starch, cellulose and plant powder; plastic carriers such as polyethylene, polypropylene and polyvinylidene chloride; and the like. These may be used alone or in combination of two or more kinds.

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Examples of the liquid carrier include alcohols classified broadly into monohydric alcohols such as methanol, ethanol, propanol, isopropanol and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol and glycerin; polyhydric alcohol derivatives such as propylene based glycol ether; ketones such as acetone, methylethyl ketone, methylisobutyl ketone, diisobutyl ketone, and cyclohexanone; ethers such as ethyl ether, dioxane, cellosolve, dipropyl ether and tetrahydrofuran; aliphatic hydrocarbons such as n-paraffin, naphthene, isoparaffin, kerosene and mineral oil; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha and alkylnaphthalene; halogenated hydrocarbons such as dichloroethane, chloroform and carbon tetrachloride; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate and dimethyl adipate; lactones such as γ-butyrolactone; amides such as Ν,Ν-dimethylformamide, N,N-diethylformamide, Ν,Ν-dimethyllacetamide and N-alkyl pyrrolidinone; nitriles such as acetonitrile; sulfur compounds such as dimethylsulfoxide; vegetable oils such as soybean oil, canola oil, cottonseed oil and castor oil; water; and the like. These may be use alone or in combination of two or more kinds.

The surface active agent is not particularly limited, but preferred are those either turning into a gel in water or exhibiting swelling property. Examples thereof include non-ionic surface active agents such as sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formaldehyde condensate, polyoxyethylene polyoxypropylene block polymer, alkylpolyoxyethylene polypropylene block polymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzylphenyl ether, polyoxyalkylene styrylphenyl ether, acetylene diol, polyoxyalkylene-added acetylene diol, polyoxyethylene ether silicone, ester silicone, fluorine-based surface active agent, polyoxyethylene castor oil, and polyoxyethylene hydrogenated castor oil; anionic surface active agents such as alkyl sulfate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkylphenyl ether sulfate, polyoxyethylene styrylphenyl ether sulfate, alkyl benzene sulfonate, lignin sulfonate,

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PCT/JP2011/062643 alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, naphthalenesulfonic acid formaldehyde condensate salt, alkylnaphthalenesulfonic acid formaldehyde condensate salt, fatty acid salt, polycarboxylate, N-methyl-fatty acid sarcosinate, resin acid salt, polyoxyethylene alkyl ether phosphate, and polyoxyethylene alkylphenyl ether phosphate; cationic surface active agents such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, and alkyldimethylbenzalkonium chloride; amino acid or betaine type amphoteric surface active agents; and the like.

These surface active agents may be used alone or in combination of two or more kinds.

Examples of the binder or tackifier include carboxymethyl cellulose and a salt thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol having an average molecular weight of 6,000 to 20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000 natural phospholipids (for instance, cephalic acid, lecithin) and the like.

Examples of the thickener include water-soluble polymers such as xanthan gum, guar gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxy vinyl polymer, acrylic polymer, starch derivative and polysaccharide; fine inorganic powders such as high purity bentonite and white carbon; and the like.

Examples of the coloring agent include inorganic pigments such as iron oxide, titanium oxide and Prussian blue; organic dyes such as alizarin dye, azo dye and metal phthalocyanine dye; and the like.

Examples of the extender agent include silicone surface active agent, cellulose powder, dextrin, processed starch, polyaminocarboxylic acid chelate compound, crosslinked polyvinylpyrrolidone, maleic acid-styrenes-methacrylic acid copolymer, half ester of polyhydric alcohol polymer with dicarboxylic anhydride, water-soluble salt of polystyrene sulfonate and the like.

Examples of the spreader include various surface active agents such as dialkyl sodium sulfosuccinate, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether and polyoxyethylene fatty acid ester, paraffin, terpene, polyamide resin, polyacrylate,

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PCT/JP2011/062643 polyoxyethylene, wax, polyvinylalkyl ether, alkylphenol-formaldehyde condensate, synthetic resin emulsion and the like.

Examples of the antifreezing agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, glycerin, and the like.

Examples of the anticaking agent include polysaccharides such as starch, alginic acid, mannose and galactose, polyvinylpyrrolidone, white carbon, ester gum, petroleum resin and the like.

Examples of the collapsing agent include sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, copolymer of methacrylic acid ester, polyvinylpyrrolidone, polyaminocarboxylic chelate compound, sulfonated styrene-isobutylene-maleic anhydride copolymer, starch-polyacrylonitrile graft copolymer and the like.

Examples of the decomposition inhibitor include desiccants such as zeolite, quicklime and magnesium oxide; antioxidants that are based on phenol, amine, sulfur and phosphoric acid; ultraviolet absorbers that are based on salicylic acid, benzophenone or the like; and the like.

Examples of the antiseptic agent include potassium sorbate, l,2-benzthiazolin-3-one and the like.

According to the agrochemical composition of the invention, in the case where the additive components described above are included, the content ratio of the carrier (weight base) is generally selected from 5 to 95%, preferably from 20 to 90%, the content ratio of the surface active agent is generally selected from 0.1 to 30%, preferably from 0.5 to 10%, and the content ratio of other additives are selected from 0.1 to 30%, preferably from 0.5 to 10%.

The agrochemical composition of the invention can be used in any forms such as liquid formulation, emulsifiable concentrate, wettable powder, dust, oil solution, water dispersible granule, flowable, granule, Jumbo formulation, and suspoemulsion.

On the occasion of use, the agrochemical composition can be sprayed after being diluted in an adequate concentration or be used directly.

The agrochemical composition of the invention can be used for foliage application, soil application, water-surface application or the like. The agrochemical composition of the

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PCT/JP2011/062643 invention, in particular the herbicides, is used for soils, i.e., farmland of fields and paddy fields in which agrohorticultural plants are cultivated.

For the agrochemical composition of the invention, the blending ratio of active component according to the invention is arbitrarily selected as needed. In the case of dust, granule or the like, the ratio should be arbitrarily selected from 0.01 to 10% (by weight), preferably from 0.05 to 5% (by weight). In the case of emulsifiable concentrate, wettable powder or the like, the ratio should be arbitrarily selected from 1 to 50% (by weight), preferably from 5 to 30% (by weight). In addition, in the case of a flowable agent or the like, the ratio should be arbitrarily selected from 1 to 40% (by weight), preferably from 5 to 30% (by weight).

The application amount of the agrochemical composition according to the invention varies depending on a kind of a compound to be used, target weed, growth pattern, environmental conditions, formulation for use or the like. In the case of a direct use of dust, granule or the like, the amount should be arbitrarily selected from 1 g to 50 kg, preferably from 10 g to 10 kg per hectare as an active component. Further, in the case of using in a liquid form, for example, in the case of emulsifiable concentrate, wettable powder, flowable agent or the like, the amount should be arbitrarily selected from 0.1 to 50,000 ppm, preferably from 10 to 10,000 ppm.

The agrochemical composition of the invention has an excellent herbicidal activity, and therefore is useful as herbicides in particular.

According to purpose of use, the agrochemical composition of the invention may be formulated, mixed or used in combination with at least one additional agrochemically active component, for example, a plant disease control component, a pesticidal component, an acaricidal component, an nematocidal component, a synergistic agent component, an attracting component, a repellent component, a herbicidal component, a safener component, a microbial pesticidal component, a plant growth control component, a fertilizer component, a soil improving agent, etc.

When the composition is used in combination with other agrochemically active component or fertilizer, the preparation of each individual component may be mixed with others at the time of use. Further, each preparation of an individual component may be used in order, or used with an interval of some days. When the preparations are used with an interval of some days, they may be applied with an interval of 1 day to 40 days, for example, although it may vary depending

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According to the agrochemical composition of the invention, when a mixture of at least one compound selected from the triazine derivatives represented by Formula 1 and their salt and at least one kind selected from other agrochemically active components is used, they are generally used in weight ratio of 100 : 1 to 1 : 100, preferably 20 : 1 to 1 : 20, and particularly 10 : 1 to 1 :

10.

Among other agrochemically active components that may be mixed or used in combination with the compound of the invention in the agrochemical composition of the invention, examples of known herbicides or plant growth control agents are described below, but the invention is not limited thereto.

[Herbicides]

Al. Acetyl CoA carboxylase (ACCase) inhibition type herbicides (Al-1) Aryl oxy phenoxy propionic acid-based compound: clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, diclofop-P-methyl, fenoxaprop-P-ethyl, fluazifop-butyl, fluazifop-P-butyl, haloxyfop, haloxyfop-etotyl, haloxyfop-P, metamifop, propaquizafop, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, and fenthiaprop-ethyl (Al-2) Cyclohexane dione-based compound: alloxydim, butroxydhn, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, and tralkoxydim (Al-3) Phenyl pyrazoline-based compound: aminopyralid, and pinoxaden

B. Acetolactate synthase (ALS) inhibition type herbicides (B-l) Imidazolinone-based compound: imazamethabenz-methyl, imazamox, imazapic (including salts with amine or the like), imazapyr (including salts with isopropylamine or the like), imazaquin, and imazethapyr (B-2) Pyrimidinyloxy benzoic acid-based compound: bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, and pyrimisulfan (B-3) Sulfonylamino carbonyl triazolinone-based compound: flucarbazone-sodium, thiencarbazone (including sodium salt, methyl ester, or the like), propoxycarbazone-sodium, procarbazone-sodium (B-4) Sulfonylurea-based compound: amidosulfuron, azimsulfuron, bensulfuron-methyl,

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PCT/JP2011/062643 chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfulon-methyl-sodium, mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron-sodium, triflusulfuron-methyl, tritosulfuron, orthosulfamuron, propyrisulfuron, metazosulfuron, and flucetosulfuron (B-5) Triazolopyrimidine-based compound: cloransulam-methyi, diclosulam, florasulatn, flumetsulam, metosulam, penoxsulam, pyroxsulam, and HNPC-C-9908 (code number)

Cl. Herbicides 1 for photosystem II photosynthesis inhibition (Cl-1) Phenylcarbamate-based compound: desmedipham and phenmedipham (Cl-2) Pyridazinone-based compound: chloridazon and brompyrazon (Cl-3) Triazine-based compound: ametryn, atrazine, cyanazine, desmetryne, dimethametryn, eglinazine-ethyl, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryn, and trietazine (Cl-4) Triazinone-based compound: metamitron and metribuzin (Cl-5) Triazolinone-based compound: amicarbazone (Cl-6) Uracil-based compound: bromacil, lenacil, and terbacil

C2. Herbicides 2 for photosystem II photosynthesis inhibition (C2-1) Amide-based compound: pentanochlor and propanil (C2-2) Urea-based compound: chlorbromuron, chlorotoluron, chloroxuron, dimefuron, diuron, ethidimuron, fenuron, fluometuron, isoproturon, isouron, linuron, methabenzthiazuron, metobromuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron, and metobenzuron

C3. Herbicides 3 for photosystem II photosynthesis inhibition (C3-1) Benzothiadiazone-based compound: bentazone (C3-2) Nitrile-based compound: bromofenoxim, bromoxynil (including ester form with butyric acid, octanoic acid and heptanoic acid), and ioxynil (C3-3) Phenyl pyrazine-based herbicide compound: pyridafol, and pyridate

D. Photosystem I radical generation type herbicides

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PCT/JP2011/062643 (D-l) Bipyridinium-based compound: diquat and paraquat dichloride

E. Protoporpyrinogen oxidase (PPO) inhibition herbicides (E-l) Diphenyl ether-based compound: acifluorfen-sodium, bifenox, chlomethoxyfen, ethoxyfen-ethyl, fluoroglycofen-ethyl, fomesafen, lactofen, and oxyfluorfen (E-2) N-Phenylphthalimide-based compound: cinidon-ethyl, flumiclorac-pentyl, flumioxazin, and chlorphthalim (E-3) Oxy diazole-based compound: oxadiargyl and oxadiazon (E-4) Oxazolidinedione-based compound: pentoxazone (E-5) Phenylpyrazole-based compound: fluazolate and pyraflufen-ethyl (E-6) Pyrimidinedione-based compound: benzfendizone, butafenacil, and saflufenacil (E-7) Thiadiazole-based compound: fluthiacet-methyl and thidiazimin (E-8) Triazolinone-based compound: azafenidin, carfentrazone-ethyl, sulfentrazone, and bencarbazone (E-9) Other compounds: flufenpyr-ethyl, profluazol, pyraclonil, SYP-298 (code number), and SYP-300 (code number)

Fl. Phytoene desaturase (PDS) inhibition herbicides (Fl-1) Pyridazinone-based compound: norflurazon (Fl-2) Pyrimidine carboxamide-based compound: diflufenican and picolinafen (Fl-3) Other compounds: beflubutamid, fluridone, flurochloridone, and flurtamone

F2. 4-Hydroxyphenylpyruvate deoxygenase (HPPD) inhibition herbicides (F2-1) Callistemon-based compound: mesotrione (F2-2) Isoxazole-based compound: pyrasulfotole, isoxaflutole, and isoxachlortole (F2-3) Pyrazole-based compound: benzofenap, pyrazolynate, and pyrazoxyfen (F2-4) Triketone-based compound: sulcotrione, tefuryltrion, tembotrione, pyrasulfotole, topramezone, bicyclopyrone, and 4-chloro-5-(l,3-dioxocyclohexa-2-yl) carbonyl-2,3 -dihydrobenzothiophene-1,1 -dioxide

F3. Carotenoid biosynthesis inhibition (unknown target) herbicides (F3-1) Diphenyl ether-based compound: aclonifen (F3-2) Isoxazolidinone-based compound: clomazone

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G EPSP synthase synthesis inhibition (aromatic amino acid biosynthesis inhibition) type herbicides (G-l) Glycine-based compound: glyphosate (including salts with sodium, amine, propylamine, isopropylamine, dimethylamine, and trimesium)

H. Glutamine synthesis inhibition herbicides (H-l) Phosphinic acid-based compound: bilanafos, glufosinate (including salts with amine or sodium)

I. Dihydropteroic acid (DHP) inihibition herbicides (1-1) Carbamate-based compound: asulam

KI. Microtubule association inhibition type herbicides (Kl-1) Benzamide-based compound: propyzamide and tebutam (KI-2) Benzoic acid-based compound: chlorthal-dimethyl (Kl-3) Dinitroaniline-based compound: benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, and trifluralin (KI-4) Phosphoroamidate-based compound: amiprofos-methyl and butamifos (Kl-5) Pyridine-based compound: dithiopyr and thiazopyr

K2. Mitosis/Microtubule tissue formation inhibition herbicides (K2-1) Carbamate-based compound: carbetamide, chlorpropham, propham, swep, and karbutilate

K3. Very long-chain fatty acid (VLCFA) synthase inhibition herbicides (K3-1) Acetamide-based compound: diphenamid, napropamide, and naproanilide (K3-2) Chloroacetamide-based compound: acetochlor, alachlor, butachlor, butenachlor, diethatyl-ethyl, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, pethoxamid, pretilachlor, propachlor, propisochlor, S-metolachlor, and thenylchlor (K3-3) Oxyacetamide-based compound: flufenacet and mefenacet (K3-4) Tetrazolinone-based compound: fentrazamide (K3-5) Other compounds: anilofos, bromobutide, cafenstrole, indanofan, piperophos, fenoxasulfone, pyroxasulfone, and ipfencarbazone

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L. Cellulose synthesis inhibition herbicides (L-l) Benzamide-based compound: isoxaben (L-2) Nitrile-based compound: dichlobenil, chlorthiamid (L-3) Triazolocarboxamide-based compound: flupoxame

M. Uncoupler (cell membrane distraction) type herbicides (M-l) Dinitrophenol-based compound: dinotcrb and DNOC (including salts with amine or sodium)

N. Lipid bioxynthesis (excluding ACCase inhibition) inhibition herbicides (N-l) Benzofuran-based compound: benfuresate and ethofumesate (N-2) Halogenated carboxylic acid-based compound: dalapon, flupropanate, and TCA (including salts with sodium, potassium, or ammonia) (N-3) Phosphorodithioate-based compound: bensulide (N-4) Thiocarbamate-based compound: butylate, cycloate, dimepiperate, EPTC, esprocarb, molinate, orbencarb, pebulate, prosulfocarb, thiobencarb, tiocarbazil, tri-allate, and vernolate

O. Auxin synthesis inhibition herbicides (Ο-l) Benzoic acid-based compound: chloramben, 2,3,6-TBA, and dicamba (including salts with amine, diethyl amine, triethanolamine, isopropylamine, sodium, or lithium) (0-2) Phenoxy carboxylic acid-based compound: 2,4,5-T, 2,4-D (including salts with amine, diethyl amine, isopropylamine, diglycolamine, sodium, or lithium), 2,4-DB, clomeprop, dichlorprop, dichlorprop-P, MCPA, MCPA-thioethyl, MCPB (including sodium salt and ethyl ester), mecoprop (including salts with sodium, potassium, isopropylamine, triethanol amine, and dimethylamine), and mecoprop-P (0-3) Pyridine carboxylic acid-based compound: clopyralid, fluroxypyr, picloram, triclopyr, and triclopyr-butotyl (0-4) Quinoline carboxylic acid-based compound: quinclorac and quinmerac (0-5) Other compounds: benazolin

P. Auxin transport inhibition type herbicides (P-1) Phthalamates-based compound: naptalam (including salts with sodium) (P-2) Semicarbazone-based compound: diflufenzopyr

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Z. Herbicides with unknown mode of action

Flamprop-M (including methyl, ethyl, and isopropyl ester), flamprop (including methyl, ethyl, and isopropyl ester), chlorflurenol-methyl, cinmethylin, cumyluron, daimuron, methyldymuron, difenzoquat, etobenzanid, fosamine, pyributicarb, oxaziclomefone, acrolein, AE-F-150944 (code number), aminocyclopyrachlor, cyanamide, heptamaloxyloglucan, indaziflam, triaziflam, quinoclamine, endothal-disodium, phenisopham, BDPT, BAU-9403 (code number), SYN-523 (code number, SYP-249 (code number), JS-913 (code number), IR-6396 (code number), metiozolin, Triafamone, HW-02 (code number), and BCS-AA10579 (code number) [Plant growth controlling compounds]

1-Methylcyclopropene, 1-naphthylacetamide, 2,6-diisopropylnaphthalene, 4-CPA, benzylaminopurine, ancymidol, aviglycine, carvone, chlormequat, cloprop, cloxyfonac, cloxyfonac-potassium, cyclanilide, cytokinins, daminodide, dikegulac, dimethipin, ethephon, ethychlozate, flumetralin, flurenol, flurprimidol, forchlorfenuron, gibberellin acid, inabenfide, indol acetic acid, indol butyric acid, maleic hydrazide, mefluidide, mepiquat chloride, n-decanol, paclobutrazol, prohexadione-calcium, prohydrojasmon, sintofen, thidiazuron, triacontanol, trinexapac-ethyl, uniconazole, uniconazole-P, and ecolyst

Hereinbelow, known safeners which may be mixed or used in combination with the compound of the invention are exemplified, but the invention is not limited thereto: benoxacor, furilazole, dichlormid, dicyclonone, DKA-24 (Nl,N2-diallyl-N2-dichloroacetylglycinamide), AD-67(4-dichloroacetyl-l-oxa-4-azaspiro[4.5]decane), PPG-1292 (2,2-dichloro-N-(l ,3-dioxan-2-yl methyl)-N-(2-propenyl)acetamide), R-29148 (3-dichloroacetyl-2,2,5-trimethyl-l,3-oxazolidine), cloquintcet-mexyl, naphthalic anhydride (1,8-naphthalic anhydride), mefenpyr-diethyl, mefenpyr, mefenpyr-ethyl, fenchlorazole O ethyl, fenclorim, MG-191 (2-dichloromethyl-2-methyl-1,3-dioxane), cyometrinil, flurazole, fluxofenim, isoxadifen, isoxadifen-ethyl, tnecoprop, MCPA, daimuron, 2,4-D, MON4660 (code number), oxabetrinil, cyprosulfamide, lower alkyl substituted benzoic acid, and ΊΊ-35 (code number).

Among other herbicidically active components that may be mixed or used in combination with the compound of the invention, known plant disease control agents are described below, but

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1. Nucleic acid biosynthesis inhibitor acyl alanine compound: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, and metalaxyl-M; oxazolidinone-based compound: oxadixyl;

butylol lactone-based compound: clozylacon and ofurace; hydroxy-(2-amino)pyrimidine-based compound: bupirimate, dimethirimol, and ethirimol; isoxazole-based compound: hymexazol;

isotahiazolone-based compound: octhilinone;

carboxylic acid-based compound: oxolinic acid

2. Mitosis and cell differentiation inhibitor benzimidazole-based compound: benomyl, carbendazim, fuberidazole, and thiabendazole; thiophanate-based compound: thiophanate and thiophanate-methyl;

N-phenylcarbamate-based compound: diethofencarb;

toluamide-based compound: zoxamide;

phenylurea-based compound: pencycuron;

pyridinylmethyl benzamide-based compound: fluopicolide

3. Respiration inhibitor pyrimidine amine-based compound: diflumetorim;

carboxamide-based compound: benodanil, flutolanil, mepronil, fluopyram, fenfuram, carboxin, oxycarboxin, thifluzamide, bixafen, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, and boscalid;

methoxy acrylate-based compound: azoxystrobin, enestroburin, picoxystrobin, and pyraoxystrobin;

methoxycarbamate-based compound: pyraclostrobin, pyrametostrobin;

oxyiminoacetate compound: kresoxim-methyl and trifloxystrobin; oxyiminoacetamide-based compound: dimoxystrobin, metominostrobin, and orysastrobin; oxazolidinedione-based compound: famoxadone;

dihydrodioxadine-based compound: fluoxastrobin;

imidazolinone-based compound: fenamidone;

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cyanoimidazole-based compound: cyazofamid;

sulfamoyltriazole-based compound: amisulbrom;

dinitrophenylcrotonic acid-based compound: binapacryl, meptyldinocap, and dinocap;

2,6-dinitroaniline-based compound: fluazinam;

pyrimidinone hydrazone-based compound: ferimzone;

triphenyl tin-based compound: TPTA, TPTC, ΤΡΊΉ;

thiophenecarboxamide-based compound: silthiofam;

triazolopyrimidyl amine-based compound: ametoctradin

4. Amino acid and protein synthesis inhibitor anilino pyrimidine-based compound: cyprodinil, mepanipyrim, and pyrimethanil; enopyranuronic acid-based antibiotics: blasticidin-S and mildiomycin; hexopyranosyl-based antibiotics: kasugamycin;

glucopyranosyl-based antibiotics: streptomycin; tetracycline-based antibiotics: oxytetracycline;

other antibiotics: gentamycin

5. Preparation acting on signal transduction pathway quinoline-based compound: quinoxyfen;

quinazoline-based compound: proquinazid;

phenylpyrrol-based compound: fenpiclonil and fludioxonil;

dicarboxyimide-based compound: chlozolinate, iprodione, procymidone, and vinclozolin

6. Lipid and cell membrane synthesis inhibitor phosphorothiorate-based compound: edifenphos, iprobenfos, and pyrazophos; dithiolane-based compound: isoprothiolane;

aromatic hydrocarbon-based compound: biphenyl, chloroneb, dicloran, quintozene, tecnazene, and tolclofos-methyl;

1,2,4-thiadiazole-based compound: etridiazole;

carbamate-based compound: iodocarb, propamocarb-hydrochloride, and prothiocarb; cinnamic amide-based compound: dimethomorph and flumorph;

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mandelic amide-based compound: mandipropamid;

Bascillus subtilis and bactericidal lipopeptide product: Bacillus subtilis (strain: QST 713)

7. Sterol biosynthesis inhibitor piperazine-based compound: triforine;

pyridine-based compound: pyrifenox;

pyrimidine-based compound: fenarimol and nuarimol;

imidazole-based compound: imazalil, oxpoconazole-fumarate, pefurazoate, prochloraz, and triflumizole;

triazole-based compound: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, furconazole, furconazole-cis, and quinconazole;

morpholine-based compound: aldimorph, dodemorph, fenpropimorph, and tridemorph;

piperidine-based compound: fenpropidin and piperalin;

spiroketal amine-based compound: spiroxamine;

hydroxy anilide-based compound: fenhexamid;

thiocarbamate-based compound: pyributicarb;

aryl amine-based compound: naftifine and terbinafine

8. Glucan biosynthesis inhibitor glucropyranosyl-based antibiotics: validamycin;

peptidyl pyridine nucleotide compound: polyoxin

9. Melanine synthesis inhibitor isobenzofuranone-based compound: phthalide;

pyrroloquinoline-based compound: pyroquilon;

triazolobenzothiazole-based compound: tricyclazole;

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propionamide-based compound: fenoxanil

10. Preparation for inducing resistance to plant disease benzothiadiazole-based compound: acibenzolar-S-methyl;

benzoisothiazole-based compound: probenazole;

thiadiazole carboxamide-based compound: tiadinil and isotianil;

natural product: laminarin

11. Preparation with unknown mode of action or multiple mode of action copper compound: copper hydroxide, copper dioctanoate, copper oxychloride, copper sulfate, cuprous oxide, oxine-copper, Bordeaux mixture, and copper nonyl phenol sulphonate;

sulfur compound: sulfur;

dithiocarbamate-based compound: ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb, ziram, and cufraneb;

phthalimide-based compound: captan, folpet, and captafol;

chloronitrile-based compound: chlorothalonil;

sulfamide-based compound: dichlofluanid, tolylfluanid;

guanidine-based compound: guazatine, iminoctadine-albesilate, and iminoctadine-triacetate, dodine;

other compounds: anilazine, dithianon, cymoxanil, vfosetyl (ahninium, calcium, and sodium), phosphorous acid and salts, tecloftalam, triazoxide, flusulfamide, diclomezine, methasulfocarb, ethaboxam, cyflufenamid, metrafenone, potassium bicarbonate, sodium bicarbonate, BAF-045 (code number), BAG-010 (code number), benthiazole, bronopol, carvone, chinomethionat, dazomet, DBEDC, debacarb, dichlorophen, difenzoquat-methyl sulfate, dimethyl disulfide, diphenylamine, ethoxyquin, flumetover, fluoroimide, flutianil, fluxapyroxad, furancarboxylic acid, metam, nabam, natamycin, nitrapyrin, nitrothal-isopropyl, o-phenylphenol, oxazinylazole, oxyquinoline sulfate, phenazine oxide, polycarbamate, pyriofenone, S-2188 (code number), silver, SYP-Z-048 (code number), tebufloquin, tolnifanide, trichlamide, mineral oils, and organic oils

12. Microorganisms and products of microorganisms

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Agrobacterium radiobacter, Fermented product from Aspergillus spp., Bacillus spp., Harpin protein, Erwinia carotovora, Fusarium oxysporum, Gliocladium spp., Laccase, Pseudomonas spp.,

Talaromyces spp., Trichoderma spp., Extract from mushroom, and Bacteriophage

Among other herbicidically active components that may be mixed or used in combination with the compound of the invention, known pesticides, acaricides, nematocides, and synergistic agents are described below, but the invention is not limited thereto.

[Pesticides, acaricids & nematocides]

1. Acetylcholine esterase inhibitor:

(1 A) carbamate compound: alanycarb, aldicarb, aldoxycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, 3,5-xylyl methylcarbamate(XMC), and xylylcarb (IB) organo phosphorus compound: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diamidafos, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, DSP, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fenthion, fonofos, fosthiazate, fosthietan, heptenophos, isamidofos, isazophos, isofenphos-methyl, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, oxydeprofos, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propaphos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, thionazin, triazophos, trichlorfon, vamidothion, dichlofenthion, imicyafos, isocarbophos, mesulfenfos, and flupyrazofos

2. GABA receptor (chloride channel) inhibitor (2A) cyclodiene organic chloride-based compound: chlordane, endosulfan, and gamma-BCH

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3. Preparation acting on sodium channel (3A) pyrethroid-based compound: acrinathrin, allethrin [including d-cis-trans and d-trans], bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, and cyfluthrin [including beta-], cyhalothrin [including gamma- and lambda-], cypermethrin [including alpha-, beta-, theta-, and zeta-], cyphenothrin [including (lR)-trans-isomers], deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, and tau-fluvalinate [including tau-], halfenprox, imiprothrin, metofluthrin, permethrin, and phenothrin [including (lR)-trans-isomer], prallethrin, profluthrin, pyrethrine, resmethrin, RU15525 (code number), silafluofen, tefluthrin, tetramethrin, tralomethrin, transfluthrin, ZXI8901 (code number), fluvalinate, tetramethylfluthrin, and meperfluthrin (3B) DDT-based compound: DDT, methoxychlor

4. Nicotinic acetylchloine receptor agonist/antagonist (4A) neonicotinoid-based compound: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam (4B) nicotine-based compound: nicotine-sulfate

5. Nicotinic acetylchloine receptor allosteric activator spinosyn-based compound: spinetoram and spinosad

6. Chloride channel activating preparation avermectin, milbemycin-based compound: abamectin, emamectin benzoate, lepimectin, milbemectin, ivermectin, and polynactins

7. Juvenile hormone preparation diofenolan, hydroprene, kinoprene, methothrin, fenoxycarb, and pyriproxyfen

8. Preparation with non-specific mode of action (multiple mode of action)

1,3-dichloropropene, DCIP, ethylene dibromide, methyl bromide, chloropicrin, and sulfuryl fluoride

9. Feeding inhibitor pymetrozine, flonicamid and pyrifluquinazon

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10. Mite growth controlling agent clofentezine, diflovidazin, hexythiazox, and etoxazole

11. Preparation for disrupting insect intima

BT preparation:

12. ATP biosynthesis enzyme inhibitor diafenthiuron;

organo tin compound: azocyclotin, cyhexatin, and fenbutatin oxide;

propargite, tetradifon

13. Uncoupler chlorfenapyr and DNOC

14. Preparation for blocking nicotinic acetylchloine channel nereistoxin-based compound: bensultap, cartap, thiocyclam, and thiosultap

15. Chitin biosynthesis inhibitor (type 0) benzoylurea-based compound: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, and fluazuron

16. Chitin biosynthesis inhibitor (type 1) buprofezin

17. Molting inhibitor (for Diptera) cyromazine

18. Ecdysone agonist (for promoting molting) diacylhydrazine-based compound: chromafenozide, halofenozide, methoxyfenozide, and tebufenozide

19. Octopamine agonist amitraz

20. Mitochondrial electron transport chain (complex III) inhibitor cyflumetofen, hydramethylnon, acequinocyl, fluacrypyrim, and cyenopyrafen

21. Mitochondrial electron transport chain (complex I) inhibitor

ΜΕΊΊ acaricides: fenazaquin, fenpyroximate, pyridaben, pyrimidifen, tebufenpyrad, and

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22. Sodium channel inhibitor indoxacarb and metaflumizon

23. Lipid biosynthesis inhibitor tetronic-based insecticides/acaricides: spirodiclofen, spiromesifen, and spirotetramat

24. Mitochondrial electron transport chain (complex IV) inhibitor aluminium phosphide, phosphine, zinc phosphide, calcium cyanide, and phosphine

25. Neuronal inhibitor preparation (unknown mode of action) bifenazate

26. Aconitase inhibitor sodium fluoroacetate

27. Preparation acting on ryanodine receptor chlorantraniliprole, flubendiamide and cyantraniliprole

28. Other preparations (unknown mode of action) azadirachtin, amidoflumet, benclothiaz, benzoximate, bromopropylate, chinomethionat, CL900167 (code number), cryolite, dicofol, dicyclanil, dienochlor, dinobuton, fenbutatin oxide, fenothiocarb, fluensulfone, flufenerim, flusulfamide, karanjin, metham, methoprene, methoxyfenozide, methyl isothiocyanate, pyridalyl, pyrifluquinazon, sulcofuron-sodium, sulflramid, and sulfoxaflor

29. Synergistic agent piperonyl butoxide and DEF.

Hereinafter, production methods of the compound of Formula 1 according to the compound of the invention, formulation examples, and applications will be described in detail with reference to Examples below. However, the invention is not limited to these Examples in any way. In the description below, % means percent by weight and parts means parts by weight. [Example 1]

Production of 6-(2-hydroxy-6-oxo cyclohexa-1 -enecarbonyl)-2-methyl-4-phenyl-1,2,4-triazine-3,5(2H, 4H)-dione (Compound No.

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1- 50) (1) Production of 2-methyI-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l ,2,4-triazine-6-carbonyl chloride

0.93 g (3.76 mmol) of

2- methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid and 0.72 g (5.64 mmol) of oxalyl chloride were dissolved in dichloromethane (20 ml). To the mixture, a drop of N,N-dimethylfoimamide was added and stirred at room temperature for 2 hours. The reaction solution was concentrated to obtain 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carbonyl chloride as a pale yellow oily substance.

(2) Production 6-(2-hydroxy-6-oxo cyclohexa-1 -enecarbonyl)-2-methyl-4-phenyl-1,2,4-triazine-3,5 (2H, 4H)-dione

0.63 g (5.64 mmol) of 1,3-cyclohexanedione and 0.57 g (5.64 mmol) of triethylamine were dissolved in dichloromethane (20 ml) under ice cooling. To the mixture, the dichloromethane solution (10 ml) of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carbonyl chloride produced from the above (1) was slowly added dropwise, and stirred for 30 minutes under ice cooling. The reaction mixture was extracted with chloroform, and the organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residues obtained were dissolved in acetonitrile (20 ml), added with 0.57 g (5.64 mmol) of triethylamine and 0.03 g (0.38 mmol) of acetone cyanohydrin, and refluxed for 30 minutes under heating. After concentration under reduced pressure, the residues were dissolved in water and washed with ethyl acetate. The aqueous layer was acidified by using citric acid, extracted with chloroform, dried over magnesium sulfate, and concentrated under reduced pressure. The crystals obtained were washed with methanol to obtain 0.36 g of the target compound (yield 28%).

Melting point: 182 to 185°C [Example 2]

Production of

6-(5-hydroxy-1 -methyl-1 El-pyrazole-4-carbonyl)-2-methyl-4-phenyl-1,2,4-triazine-3,5(2H,

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4H)-dione (Compound No. 11-50)

1.50 g (6.07 mmol) of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid and 1.16 g (9.10 mmol) of oxalyl chloride were dissolved in dichloromethane (30 ml). To the mixture, a drop of Ν,Ν-dimethylformamide was added and stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure to obtain 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carbonyl chloride as a pale yellow oily substance.

Next, 1.22 g (9.10 mmol) of l-methyl-5-hydroxypyrazole hydrochloride and 1.53 g (15.17 mmol) of triethylamine were added to dichloromethane (30 ml) under ice cooling. To the mixture, the dichloromethane solution (15 ml) of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carbonyl chloride was slowly added dropwise, and stirred for 30 minutes. The reaction mixture was extracted with chloroform, and the organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residues obtained were dissolved in acetonitrile (30 ml), added with 0.92 g (9.10 mmol) of triethylamine and 0.05 g (0.61 mmol) of acetone cyanohydrin, and refluxed for 30 minutes under heating. The reaction mixture was concentrated under reduced pressure, and then the residues were dissolved in water and washed with ethyl acetate. The aqueous layer was acidified by using citric acid, extracted with chloroform, dried over magnesium sulfate, and concentrated under reduced pressure. The crystals obtained were washed with methanol to obtain 0.40 g of the target compound (yield 20%).

Melting point: 197 to 199°C [Example 3]

Production of 6-(2-hydroxy-4-oxobicyclo[3.2.1]octa-2-en-yl carbonyl]-2-methyl-4-phenyl-l,2,4-triazine-3,5(2H, 4H)-dione (CompoundNo. III-50)

1.00 g (4.04 mmol) of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid and 1.03 g (8.09 mmol) of oxalyl chloride were dissolved in dichloromethane (20 ml). To the mixture, a drop of Ν,Ν-dimethylformamide was added and stirred at room temperature for 2 hours. The reaction

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2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carbonyl chloride as a pale yellow oily substance.

Next, 0.83 g (6.07 mmol) of bicyclo[3.2.1]octane-2,4-dione and 0.61 g (6.07 mmol) of triethylamine were dissolved in dichloromethane (20 ml) under ice cooling. To the solution, the dichloromethane solution (10 ml) of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carbonyl chloride that is prepared previously was slowly added dropwise. After stirring for 30 minutes under ice cooling, the reaction mixture was extracted with chloroform, and the organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residues obtained were dissolved in acetonitrile (20 ml), added with 0.61 g (6.07 mmol) of triethylamine and 0.03 g (0.4 mmol) of acetone cyanohydrin, and refluxed for 30 minutes under heating. The reaction mixture was concentrated under reduced pressure, and then the residues were dissolved in water and washed with ethyl acetate. The aqueous layer was acidified by using citric acid, extracted with chloroform, dried over magnesium sulfate, and concentrated under reduced pressure. The crystals obtained were washed with methanol to obtain 0.70 g of the target compound (yield 47%).

Melting point: 163 to 165°C [Example 4]

Production of

-isopropyl-4-(2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-yl carbonyl)-lH-pyrazole-5-yl propane-1-sulfonate (Compound No. 11-267)

0.85 g (2.60 mmol) of 6-(5-hydroxy-l-isopropyl-lH-pyrazol-4-yl carbonyl)-2-methyl-4-phenyl-l,2,4-triazine-3,5(2H, 4H)-dione was dissolved in 20 ml of dichloromethane. To the solution, 0.27 g (2.60 mmol) of triethylamine and 0.37 g (2.60 mmol) of 1 -propane sulfonyl chloride were added at room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure, and the residues were purified by silica gel column chromatography (hexane : ethyl acetate = 1 : 1) to obtain 0.71 g of the target compound (yield 63%).

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Melting point: 51 to 53 °C [Example 5]

Production of

2-methyl-3,5-dioxo-4-(4-chlorophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid (Compound No. V-53) (1) Production of diethyl 2-(2-mcthylhydrazono) malonatc

5.00 g (0.0287 mol) of diethyl ketomalonate was dissolved in 30 ml ethanol. To the solution, 1.45 g (0.0316 mol) of methyl hydrazine was added and stirred for 7 hours at 60°C followed by further stirring overnight at room temperature. The reaction mixture was concentrated under reduced pressure and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residues were purified by silica gel column chromatography (hexane : ethyl acetate = 1 : 1) to obtain 5.28 g of the target compound (yield 91%).

(2) Production of ethyl 4-(4-chlorophenyl)-2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid ester

2.00 g (9.89 mmol) of diethyl 2-(2-methylhydrazono) malonate and 1.50 g (9.89 mmol) of DBU were dissolved in 50 ml of tetrahydrofuran. To the solution, the tetrahydrofuran (10 ml) solution of 4-chlorophenyl isocyanate (3.34 g, 21.7 mmol) was slowly added dropwise at room temperature, and stirred over night. The reaction mixture was concentrated under reduced pressure, and the residues were extracted with ethyl acetate, washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residues were purified by silica gel column chromatography (hexane : ethyl acetate = 7 : 1) to obtain 2.00 g of the target compound (yield 65%).

(3) Production of 2-methyl-3,5-dioxo-4-(4-chlorophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid

2.00 g (6.46 mmol) of ethyl 2-methyl-4-(4-chlorophenyl)-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid ester was stirred at room temperature for 2 days in a mixed solvent of acetic acid (30 ml) and cone, hydrochloric acid (30 ml). The reaction mixture was concentrated under reduced pressure to obtain 1.88 g of

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Melting point: 234 to 236°C [Example 6]

Production of 2,4-dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid (Compound No. V-l) (1) Production of 2-methylsemicarbazide g (282.1 mmol) of methyl hydrazine was dissolved in 60 ml of tetrahydrofuran. To the solution, 25 g (217 mmol) of trimethylsilyl isocyanate was slowly added dropwise at 0°C and further stirred for 1 hour. To the reaction mixture, 40 ml of methanol was added and stirred for 5 hours at 40°C. The reaction mixture was concentrated to obtain 18 g of 2-methyl semicarbazide as a pale yellow solid (yield 93%).

¹H-NMRiCDa₃,TMS) δίρρτη):

3.15(3H,s), 3.80(2H,br), 5.61(2H,br) (2) Production of ethyl 2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid ester

35.2 g (202 mmol) of diethyl ketomalonate and 18 g (202 mmol) of 2-methyl semicarbazide were dissolved in 200 ml ethanol, and then refluxed under heating for 36 hours. The reaction solution was concentrated to obtain 31 g of ethyl 2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid ester as a white solid (yield 78%).

’H-NMR(CDC1₃,IMS) Nppm):

1.39(3H,tJ=7.1Hz), 3.72(3H,s), 4.42(2H,qJ=7.1Hz), 9.38(lH,br) (3) Production of ethyl

2,4-dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester

2.0 g (10.0 mmol) of ethyl 2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid ester, 1.9 g (13.5 mmol) of potassium carbonate, and 1.8 g (12.5 mmol) of methyl iodide were added to 20 ml of Ν,Ν-dimethylformamide, and stirred for 2 hours at 60°C. Upon the completion of the reaction, the reaction solution was added with water, and then extracted with ethyl acetate. The organic layer obtained was dried over anhydrous magnesium sulfate and

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2.4- dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-l,2,4-triazme-6-carboxylic acid ester (yield 86%). ^!H-NMR(CDC13,TMS) 0fppm):

1.40(3H,tJ=7.1Hz), 3.38(3H,s), 3.74<3H,s), 4.42(2H,qJ=7.1Hz) (4) Production of 2,4-dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid

1.8 g (8.41 mmol) of ethyl

2.4- dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-l,2,4-triazinc-6-carboxylic acid ester was stirred at room temperature for 24 hours in a mixed solvent of acetic acid (30 ml) and cone, hydrochloric acid (30 ml). The reaction solution was concentrated to obtain 1.40 g of

2,4-dimethyl-3,5-dioxo-2,3,4,5-tctrahydro-l,2,4-triazine-6-carboxylic acid as a white solid (yield 90%).

Melting point: 220 to 223°C ’H-NMRfCDCl^TMS) δφρτη):

3.48(3H,s),3.88(3H,s) [Example 7]

Production of 2-ethyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid (Compound No. V-259) (1) Production of ethyl 3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1.2,4-triazine-6-carboxylic acid ester

9.0 g (0.0517 mol) of diethyl ketomalonate and 7.81 g (0.0517 mol) of 2-phenyl semicarbazide were stirred in 50 ml xylene for 1 hour at 100°C. The reaction mixture was refluxed under heating, and by adding sodium methoxide (8.37 g, 0.155 mol) in small portions, the reaction was completed. After cooling to room temperature, the reaction mixture was neutralized with 1 N aqueous hydrochloric acid solution, extracted with ethyl acetate, and dried over magnesium sulfate. The reaction mixture was concentrated under reduced pressure and the residues were isolated and purified by silica gel column chromatography (hexane : ethyl acetate = 2 : 1) to obtain 6.18 g of the target compound (yield 46%).

(2) Production of ethyl

2-ethyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid ester

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1.50 g (5.74 mmol) of ethyl

3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid ester was dissolved in 30 ml of Ν,Ν-dimethylformamide, added with 60% sodium hydride (0.23 g, 5.74 mmol) under ice cooling, and further stirred for 30 minutes. The mixture was added with ethyl iodide (0.90 g, 5.74 mmol) and stirred. After raising to room temperature, an aqueous solution of ammonium chloride was added to terminate the reaction. The resultant was extracted with diethyl ether, dried over magnesium chloride, and concentrated under reduced pressure. The residues were purified by silica gel column chromatography to obtain 1.33 g of the target compound (yield 80%).

(3) Production of 2-ethyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid

1.30 g (4.49 mmol) of ethyl 2-ethyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazme-6-carboxylic acid ester was dissolved in 30 ml ethanol, added with a 25% aqueous solution of sodium hydroxide (1.29 g, 8.09 mmol), and stirred overnight. After dilution by adding water, the aqueous layer was washed with diethyl ether. The aqueous layer was acidified by adding 6 N aqueous hydrochloric acid solution, and then extracted with ethyl acetate. After drying over magnesium sulfate and concentration under reduced pressure, 1.10 g of the target compound was obtained (yield 94%). [Example 8]

Production of 2,4-dimethyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid (Compound No. V-265) (1) Production of ethyl

2,4-dimethyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester

2.00 g (9.89 mmol) of diethyl 2-(2-methylhydrazono) malonate and 1.50 g (9.89 mmol) of l,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were dissolved in 50 ml of tetrahydrofuran. To the solution, the tetrahydrofuran (10 ml) of methylisothiocyanate (1.58 g, 21.7 mmol) was slowly added dropwise and stirred overnight. The reaction mixture was concentrated under reduced pressure, extracted with ethyl acetate, washed with water, and dried over magnesium sulfate. The residues obtained after concentration under reduced pressure were purified by silica gel

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(2) Production of

2.4- dimethyl-5-oxo-3 -thioxo-2,3,4,5 -tetrahydro-1,2,4-triazine-6-carboxylic acid

2.30 g (0.01 mol) of ethyl

2.4- dimcthyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid ester was stirred overnight at room temperature in a mixed solvent of acetic acid (30 ml) and cone, hydrochloric acid (30 ml). The reaction mixture was concentrated under reduced pressure to obtain 2.01 g of the target compound (yield; quantitative).

[Example 9]

Production of

2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5 -tetrahydro-1,2,4-triazine-6-carboxylic acid (Compound No. V-72) (1) Production of ethyl 2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid ester

2.0 g (9.89 mmol) of diethyl 2-(2-methylhydrazono) malonate and 3.3 g (21.8 mmol) of l,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were dissolved in 20 ml of tetrahydrofuran. To the solution, 4.9 g (20.8 mmol) of phenyl-2-cyanophenylcarbamate was added at room temperature and stirred for 1 hour at the same temperature. After that, the mixture was refluxed under heating for 3 hours. The reaction solution was concentrated and the residues were extracted with ethyl acetate. The organic layer obtained was washed with water and an aqueous solution of citric acid in order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residues were purified by silica gel column chromatography (hexane : ethyl acetate = 2 : 1) to obtain 2.3 g of ethyl 2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-l,2,4-triazme-6-carboxylic acid ester (yield 78%).

te-NMRiCDCb/IMS) 8(ppm):

1.40(3H,tJ=7.1Hz),3.81(3H»,4.45(2H,q_rr=7.1HzX739(lHAJ=8OHz),

7.60-7.64(lHm), 7.75-7.80(lH^n), 7.85(lH,dJ=7.6Hz)

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2018201082 14 Feb 2018 (2) Production of 2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2.3,4,5-tetrahydro-l,2.4-triazme-6-carboxylic acid

2.3 g (7.65 mmol) of ethyl 2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid ester was stirred for 24 hours at room temperature in a mixed solvent of acetic acid (30 ml) and cone, hydrochloric acid (30 ml). The reaction solution was concentrated under reduced pressure to obtain 1.8 g of 2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-l,2,4-triazme-6-carboxylic acid as a white solid (yield 90%).

Melting point: 213 to 215°C ‘H-NMR/DMSCTdfc IMS) 8(ppm):

3.65(3H,s), 7.67(lH,dJ=8.0Hz), 7.70-7.75(lHjn), 7.90-7.96(lH,m),

8.09(111,dJ=74Hz), 14.02(lH,br) [Example 10]

Production of 2-methyl-3.5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid (Compound No. V-50) (1) Production of ethyl

2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid ester

2.0 g (9.89 mmol) of diethyl 2-oxomalonate and 0.04 g (0.2 mmol) of p-toluene sulfonic acid were dissolved in 50 ml of toluene. To the solution, 2.5 g (15.2 mmol) of

1- methyl-N-phenylhydrazine carboxamides was added at room temperature, and then stirred for 2 hours with reflux under heating. The reaction mixture was cooled to room temperature and added with 0.08 g (0.5 mmol) of l,8-diazabicyclo[5.4.0]undec-7-ene (DBU) followed by stirring at room temperature for two hours. The reaction solution was washed with water and dried over magnesium sulfate. The solvent was distilled off to obtain ethyl

2- methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid ester.

(2) Production of

2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l ,2,4-triazine-6-carboxylic acid

Ethyl 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-l,2,4-triazine-6-carboxylic acid ester

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Melting point: 195 to 198°C ‘H-NMRfDMSO-cU'IMSja/ppm):

3.59(3H,s), 729-7.3 l(2Hm), 7.43-7.54(3Hm), 13.64(lH,bs)

Physical property values (melting point or refractive index) of the compound of the invention represented by Formula 1, which has been synthesized according to the above Examples, are shown in Table 68 to Table 70 including above Examples. Herein, * means 15 refractive index.

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2018201082 14 Feb 2018 [Table 68]

Compound No.	Melting Point(t) or Refractive Index (no²⁰)
1-2	87-89
1-3	1.5530*
1-5	1.5630*
1-9	1.5380*
110	124125
Ill	97-98
1-14	126129
1-16	116118
1-19	132-134
1-27	1.5460*
1-41	1.5495*
1-43	98101
1-47	155157
1-50	182185
1-51	184-185
1-52	187 190
1-53	182-183
1-54	174176
1-55	209-212
1-56	181-183
1-57	135136
1-58	198199
1-59	190-193
1-60	190191
1-61	186-187
1-62	137-139
1-63	166169
1-64	89-92
1-65	184-187
1-66	151-152
1-67	174-177
1-68	208-210
1-71	130-131
1-72	166169
1-73	181-184
1-74	108-111
1-75	173-176
1-76	242-245
1-77	192-194
1-78	149-151
1-79	161163
1-80	98101
I 81	158161
1-82	212-215

Compound No.	Melting Point(t) or Refractive Index (hd²°)
1-83	191-194
1-84	124-127
1-85	235-238
1-86	199-202
1-87	197198
1-88	160-163
1-89	190193
1-90	164-166
1-91	89-91
1-92	245-247
1-93	168169
1-94	155-157
1-96	151153
1-98	155157
1-99	178181
I 105	186188
1106	228-231
1107	212-215
1-108	167169
1-109	166168
1110	151152
1-111	196199
1-115	144147
1-116	176179
1-117	140-143
1-118	140 143
1-119	191-194
1-120	191-194
1-125	148-151
1-126	126129
1-127	237-240
1-128	217 220
1-129	155158
1-131	204-205
1-134	215-217
1-135	152-154
1136	156157
1-137	154-157
1-138	123126
1-149	175178
1-155	196199
1-167	183185
I 169	178180
1-170	213-215

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2018201082 14 Feb 2018 [Table 69]

Compound No.	Melting Pointffc) or Refiractive Index (ηη^Ζ°)
1-179	215-218
1-182	159-161
IT83	138141
1-184	100-103
1-185	108-111
1-187	180-183
1-189	190-193
1-198	135137
I 199	169170
1-202	161-162
1-203	188-191
1-204	201-204
1-205	87-90
1-259	150-153
1-260	152-154
1-261	190193
1-262	103106
1-263	174-176
1-265	164167
1-268	201-204
1-269	112-115
I 270	172-175
1-271	251-254
I 272	204 207
I 274	101T03
1-275	89-92
1-276	167T70
1-277	96 99
1-278	98-101
I 279	218-220
1-280	168-171
1-281	146-147
1-282	148-151
1-283	172-175
1-284	160T62
1-285	149-152
1-286	88-91
1-287	155-158
1-288	94-97
1-289	215-218
1-290	138141
1-291	194197
1-292	167169

Compound No.	Melting PointCC) or Refiractive Index (nn²⁰)
1-293	158-160
1-294	113-115
1-295	1.5360*
1-296	1.5300*
1-297	89-92
1-298	148-150
1-299	212-215
1-300	203-205
Ί-301	274-277
1-302	222-224
1-303	62-65
1-304	148T51
1-307	58-61
1-328	58-61
1-463	131T34
1-464	168170
1-465	211-213
1-466	89-92
1-467	211-214
1-468	128130
1-469	172-174
1-470	147T48
1-471	1.5620*
1-472	162 164
1-473	143T46
1-474	70-73
1-475	83-86
1-476	191193
1-477	149 151
1-478	1.5270*
1-479	1.5450*
1-480	179T81
11-50	197-199
11-267	51-53
HI-50	163-165
III-62	158-159
VI-1	151-154
VI-5	145-148
VI-6	145T46
VI-7	163-166
VI-65	93-96
VI-97	158T60

Compound number and 'H-NMR data (standard; TMS, δ (ppm) value) are given below.

Data without a name of solvent are measured by using CDCfi.

Compound No. I-1:

2.04-2.10(2Hjn), 2.45-2.49(2Hm), 2.76-2.80(21 Lm), 3.56(3114

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3.65(3¾). 16.05(lH,br)

Compound No. 1-3:

0.92(3H,tJ=6.00Hz), 1.69(2H,qJ=6.00Hz), 2.03-2. 11(21¾).

2.45-2.49(21¾). 2.75-2.79(21¾). 3.64(3¾). 3.89(2H,U=6.00Hz),

16.05(lH,br)

Compound No. 1-4:

1.49(6H,d, 1=6.00¾). 2.03-2.1 1(21¾). 2.44-2.49(21¾). 2.74-2.79(21¾).

3.61(3¾). 5.07(lH,sepU=6.00Hz), 16.08(lH,br)

Compound No. 1-5:

0.95(314,(1=7.2¾). 1.32-1.43(21¾). 1.59-1.68(2^1),2.03-2.10(21¾).

2.45-2.49(21¾). 2.75-2.79(21¾). 3.64(3¾). 3.92(2H,(J=6.9IIz), 16.05(lH,br)

Compound No. 1-9:

0.88(3¾ 1=6.6¾). 120-1.40(61¾). 1.58-1.64(21¾).2.03-2.12(21¾).

2.44-2.48(21¾). 2.75-2.79(21¾). 3.64(3¾). 3.89-3.94(21¾).

16.04(lH,br)

CompoundNo. 1-27:

1.65(3H,U=3.00Hz),2.03-2.09(2H,m),2.31-2.36(21¾).2.44-2.49(21¾).

2.74-2.79(21¾).3.64(3¾).4.01(2H,(J=6.00),16.00(lHbr)

CompoundNo. 1-41:

[0251]

1.89-1.97(21¾).2.04-2.11(21¾).2.44-2.48(21¾).3.31(3¾).

3.44(211,(1=6.0¾). 3.64(3¾). 4.03(211,(3=7.0¾). 16.04(lH,br) CompoundNo. 1-75:

2.05-2.11(21¾). 2.45-2.49(21¾). 2.75-2.80(21¾). 3.69(3¾).

7.05-7.09(11¾). 7.14-7.21(11¾). 7.24-7.33(11¾). 15.99(1¾) CompoundNo. 1-76:

2.04-2.09(21¾). 2.46-2.50(21¾). 2.75-2.80(21¾). 3.69(3¾).

6.88-6.96(31¾). 15.97(1¾)

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Compound No. 1-77:

2.03-2.09(2Hjn), 2.45-2.49(2Hjn), 2.75-2.78(2Hpn), 3.71(3¾).

7.11-7.14(lHm), 7.18-7.33(2Hpn), 15.95(1¾)

Compound No. 1-79:

2.04-2.10(2H,m), 2.45-2.50(2Hm), 2.75-2.79(2Hpn), 3.70(3H,s),

7.10-724(3Hpn), 15.96(1¾)

Compound No. 1-80:

2.01-2.08(2Hjn), 2.46-2.49(2Hpn), 2.75-2.78(2H,m), 3.71(3¾).

7.05-7.08(2Hpn), 7.4O-7.48(lHm), 15.93(1¾)

Compound No. 1-81:

[0252]

2.05-2.08(2Hm), 2.45-2.50(2Hpn), 2.75-2.80(2ILm), 3.69(3H,s)_:

7.14-7.19(lH,m),7.43(lH,dJ=2.5), 7.57(1 H,dJ=8.5), 15.97(1¾) Compound No. 1-295:

0.85-0.89(3Hpn), 126-1.32(10H/n), 1.57-1.65(2Hpn), 2.05-2.12(2Hjn),

2.44- 2.49(2Hpn),2.75-2.79(2Hpn), 3.64(3¾). 3.88-3.93(2Hpu),

16.04(lH,br)

CompoundNo. 1-296:

0.854).90(3¾^ 125-1.36(14¾). 1.59-1.69(2Hpn), 2.05-2.09(2¾).

2.44- 2.49(2Hpn),2.74-2.79(2Hpn), 3.64(3¾). 3.88-3.93(2Hpn), 16.04<lH,br)

CompoundNo. 1-306:

0.96(3H,tJ=7.15), 1.39-1.46(2Hjn), 1.69-1.71(2Hpn),2.05-2.09(2Hpn),

2.44- 2.48(2Hpn), 4.01(2H,U=7.69), 7.32-7.36(2Hpn), 7.56-7.59(lHpn),

7.83-7.88(lHpn), 8.61-8.63(lHpn), 16.05(lH,br)

CompoundNo. 1-308:

0.88-0.92(3Hpn), 0.354).37(4Hpn)_: 0.79-1,82(2Hm), 2.03-2.07(2Hpn),

2.44- 2.49(2Hm), 2.73-2.78(2Hpn)_: 4.01(2H,tJ=7.69), 7.28-7.30(2Hpn),

7.43-7.53(3Hjm), 16.06(lH,br)

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Compound No. 1-339:

1.84-2.11(4Hjn), 2.44-2.48(2Η^η), 2.74-2.78(2Hdn), 3.64(3H,s),

3.69-3.92(3H,m), 4.074.34(2Hm),16.04{lH,br)

Compound No. 1-462:

1.30(3 H,tJ=7.66),2.03-2.07(2Hjn),2.45-2.49(2am),2.69-2.77(4H4n),

3.68(3H,s), 7.28-730(lHin), 7.77-7.73(lHgn), 8.51(lH,s), 16.03(lH,br)

Physical property values of the production intermediate [13a] and [3b] are given in Table 70 and Table 71.

[Table 70]

Compound No.	Melting Point CO)
IV-116	111-114
IV117	100102
IV-118	118121
IV-136	131133
IV-137	102-105
IV-138	122125
IV-182	107-108
IV185	50-53
IV-197	122-125
IV-259	84-86
IV-260	107-109
IV-261	132-135
IV-275	102103
IV-276	46-49
IV-278	171-172
IV-280	137-140
IV-284	136-137
IV-285	112114
IV-287	140-142
IV-288	101-102
IV-290	124-127
IV-291	137-138

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2018201082 14 Feb 2018 [Table 71]

Compound No.	Melting PointCt)
VI	220-223
V-2	165-168
V-3	113-115
V-4	122-125
¥-5	98100
V-9	99-102
v-io	127129
VI1	82-84
¥14	142144
V-16	155158
V-27	114117
V-41	90-91
V-43	145146
V-47	144147
V-50	195198
V-51	154157
V-52	118-120
V-53	234-236
V-54	95-98
V-55	95-98
V-56	212-215
V-57	150152
V-58	196-199
V-60	145-146
V-61	173-174
V-66	164-166
V-67	200-203
V-68	206-209
V-72	213-215
V-73	221 224
V-87	162 165
V-88	227-230
V-89	184-186
V-90	156-159
V-91	179-181
V-92	207-210
V-93	220-223
V-99	166169
V-105	169171
V-106	231-234
V-107	166 169
V-108	153156
V-109	197-198
V-110	194-197
V-lll	187-190
V115	188191
V-l 19	205-208
V-125	173-175
V 127	135 138
V-128	186-188
V-129	198-201

Compound No.	Melting PointCt)
V-131	201-204
V-135	224-227
V149	216-218
V-155	229-231
V-167	211-212
V169	199-202
V-170	177-180
V-179	237-240
V184	158161
V189	200-201
V-202	200-203
V-203	164-167
V-204	199-202
V-268	201-204
V-269	155-157
V-270	184-187
V-271	208-211
V-272	100-102
V-273	202-205
V-275	166169
V-282	193 196
V-283	186 189
V-291	175-178
V-294	204-207
V-295	105107
V-296	106-108
V-297	176-179
V-298	145146
V-299	241-244
V 300	245-248
V 301	259-261
V-302	211-212
V-303	152-155
V-304	140-143
V-305	166-167
V-328	143-146
V-358	240-243
V-359	91-94
V-360	240-242
V-361	155-158
V-362	148-151
V-363	189192
V-364	213-216
V-365	75-78
V-366	218-221
V-367	192-195
V-368	153156
V-369	111-113
V-370	100103
V-371	80-83

Compound number and ’H-NMR data (standard; TMS, δ (ppm) value) for the production

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Compound No. IV-19:

1.19-1.41(3H,m), 1.39(3H,t,J=5.3Hz), 1.56-1.66(3H,m), 1.83-1.87(2H,m),

2.37(2H,dq,J=3.3Hz,12.1Hz), 3.68(3H,s), 4.41(2H,q,J=7.1Hz), 4.73(lH,tt,J=3.3Hz,12.1Hz)

Compound No. IV-50:

1.39(3H,t,J=7.1Hz), 3.71(3H,s), 4.43(2H,q,J=7.1Hz), 7.24-7.26(2H,m),

7.49-7.57(3H,m)

Compound No. IV-53:

1.39(3H,t,J=5.3Hz), 3.77(3H,s), 4.43(2H,q,J=5.3Hz), 7.18(2H,d,J=6.4Hz),

7.49(2H,d,J=6.4Hz)

Compound No. IV-56:

1.39(3 H,t,3=7.1 Hz), 3.77(3H,s), 4.43(2H,q,J=7.1Hz), 7.20-7.22(4H,m)

Compound No. IV-59:

1.39(3H,t, 1=7.1 Hz), 2.41(3H,s), 3.77(3H,s), 4.42(2H,q,J=7.1Hz),

7.10(2H,d,J=8.3Hz), 7.31(2H,d,J=8.3Hz)

Compound No. IV-62:

1.39(3 H,t, 3=7.1 Hz), 3.76(3H,s), 3.84(3H,s), 4.43(2H,q,J=7.1Hz),

7.01 (2H,d,J=9.0Hz), 7.14(2H,d,J=9.0Hz)

Compound No. IV-63:

1.39(3H,t,3=7.1Hz), 3.78(3H,s), 4.43(2H,q,J=7.1Hz), 7.30(lH,d,J=7.7Hz),

7.67(1H,t,3=7.7), 7.74(lH,dt,3=1.lHz,7.7Hz), 7.84(1 H,dd,3=1.1 Hz,7.7Hz)

Compound No. IV-64:

1.40(3H,t,3=7.1Hz), 3.78(3H,s), 4.44(2H,q,J=7.1Hz), 7.44(lH,d,J=8.0Hz),

7.54(lH,s), 7.66(lH,t,J=8.0Hz), 7.75(lH,d,J=8.0Hz)

Compound No. IV-65:

1.40(3H,t,J=5.3Hz), 3.79(3H,s), 4.44(2H,q,J=5.3Hz), 7.39(2H,d,J=6.2Hz),

7.79(2H,d,J=6.2Hz)

Compound No. IV-71:

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1.39(3H,t,J=7.1Hz), 3.78(3H,s), 4.43(2H,q,J=7.1Hz), 7.28(2H,d,J=8.5Hz), 7.36(2H,d,J=8.5Hz)

Compound No. IV-74:

1.39(3H,t,J=7.1Hz), 3.78(3H,s), 4.44(2H,qJ=7.1Hz),

7.39(2H,dd,J=l ,9Hz,6.6Hz), 7.82(2H,dd,J=l .9Hz,6.6Hz)

Compound No. IV-78:

1.40(3H,t,J=7.1Hz), 3.79(3H,s), 4.43(2H,q,J=7.1Hz), 6.99-7.05(2Hjn),

7.22-7.28(lH,m)

Compound No. IV-93:

1.39(3H,tJ=7.1Hz), 3.77(3H,s), 3.78(6H,s), 4.43(2H,q,J=7.1Hz),

6.35(2H,d,J=2.2Hz), 6.55(111,t,J=2.2Hz)

Compound No. IV-96:

1,39(3H,M=7.1 Hz), 3.76(6H,s), 3.83(3H,s), 4.42(2H,q,>7.1Hz), 6.55-6.59(2H,m), 7.05(lH,d,J=9.1Hz)

Compound No. IV-134:

1.40(3H,t,J=5.3Hz), 3.77(3H,s), 3.79(3H,s), 4.43(2H,q,J=5.3Hz), 6.97(lH,d,J=6.8Hz), 7.17(lH,d,J=2.0Hz), 7.41(lH,dd,J=2.0Hz,6.8Hz)

Compound No. IV-179:

1.39(3H,t,J=5.3Hz), 3.77(3H,s), 4.43(2H,q,J=5.3Hz), 7.32(lH,d,J=5.7Hz), 20 7.46(lH,dd,J=5.7Hz,3.7Hz), 7.92(lH,dt,J=l.lHz,5.7Hz),

8.68(lH,dt,J=3.7Hz,l.lHz)

Compound No. IV-198:

1.40(3H,t,J=5.3Hz), 3.78(3H,s), 4.43(2H,q,J=5.3Hz), 7.07-7.12(2H,m), 7.42(lH,dd,J=l.lHz, 4.0Hz)

Compound No. IV-259:

1.39(3H,t,J=7.1Hz), 1.43(3H,t,J=7.1Hz), 4.17(2H,q,J=7.1Hz), 4.43(2H,q,J=7.1Hz), 7.21-7.26(2H,m), 7.44-7.55(3H,m)

Compound No. IV-260:

1.39(3H,t,J=7.1Hz), 1.43(6H,d,J=6.8Hz), 4.42(2H,q,J=7.1Hz),

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5.01(lH,p,J=6.8Hz), 7.22-7.26(2H,m), 7.46-7.55(3H,m)

Compound No. IV-261:

1.40(3H,t,J=7.1Hz), 4.46(2H,q,J=7.1Hz), 7.23-7.26(2H,m), 7.47(lH,t,J=57.8Hz), 7.51-7.66(3H,m)

Compound No. IV-262:

1.39(3H,t,J=7.1Hz), 4.44(2H,q,J=7.1Hz), 7.26-7.60(1 OH,m)

Compound No. IV-265:

1.40(3H,t,J=7.1Hz), 3.71(3H,s), 4.05(3H,s), 4.44(2H,q,J=7.1Hz)

Compound No. IV-286:

1.19-1.17(6H,dd,J=7.0 HzJ=2.2 Hz), 1.41-1.37(3H,t,J=7.0Hz),

2.65-2.58(lH,sept.,J=7.0Hz), 3.78(3H,s), 4.46-4.39(211,q,J=7.0Hz), 7.05-7.03(lH,d.J=8.0Hz), 7.33-7.29(lH,m), 7.47-7.46(2H,d,J=4.0 Hz)

Compound No. V-19: (solvent for measurement: DMSO-dg)

1.09-1.34(3Hqn), 1.59-1.64(2ELm), 1.76-1.80(2Hm), 2.22(2H,dqd=3.3Hz,12.3Hz),3.51(3H,s).4.54(lH,tLJ=3.3Hz,l2.3Hz), 13.53(lH,bs)

Compound No. V-50:(solvent for measurementDMSO-cf)

3.59(3H,s), 7.29-7.3 l(2H^n),7.43-7.54(3Efin\ 13.64{lH,bs)

Compound No. V-53 :(solvent for measuiementDMSO-de)

3.59(3H,s), 7.35(2H,ddJ=l .6Hz,5.0Hz), 7.59(2H,ddJ=l .6Hz,5.0Hz), 13.66(lH,bs)

Compound No. V-56:(solvent for measurementDMSO-ds)

3.59(3H,s), 7.34-7.37(4H,m)_: 13.65(lH,bs)

Compound No. V-59:(solvent for measurementDMSO-de)

2.36(3H,s)_: 3.58(3H,s), 7.17(2HdJ-8.3Hz)_: 7.30(2H,d>8.3Hz), 13.62(lH,bs)

Compound No. V-62:(solvent for measurementDMSO-ds)

3.39(3H,s), 3.74(3H,s), 6.93(2H,dJ=9.0), 7.39(2H,cU=9.0Hz),

9.54(lH,bs)

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Compound No. V-63 {solvent for measurement:DMSO-dg)

3.62(3H,s), 7.64(1 H,dJ=7.7Hz), 7.75(lH,tJ=7.68Hz), 7.87-7.94(2Hjn),

13.90(lH,bs)

Compound No. V-64 {solvent for measurementrDMSO-dg)

3.41(3Hs), 7.46(lH,dJ=6.0Hz), 7.60(lH,U=6.0Hz), 7.82(lH,dJ=6.0Hz),

7.97(144,s),9.90(lH,bs)

Compound No. V-65{solvent for mcasurcmentiDMSO-dg)

3.60(3H,s)₅ 7.58(2H,dJ=8.3Hz), 7.92(241,dJ=8.3IIz), 13.69(144» [0259]

Compound No. V-71: (solvent for measurement: DMSO-dg)

3.59(34», 7.47(2H,dfJ=9.3HzL.2Hz), 7.54(2H,dJ=9.3Hz), 13.67(1H»

CompoundNo. V-75:

3.92(3H,s), 7.03-7.06(144», 7.13-7.18(14»), 7.35-7.41(14»)

CompoundNo. V-76:

3.92(34», 7.85-7.87(21»), 7.00-7.12(14»)

CompoundNo. V-77:

3.94(344,s), 7.07-7.11(14»), 729-7.31(14»), 7.38-7.42(lILm)

CompoundNo. V-78:(solvent for measurementDMSO-dg)

3.61(341,s)_;7.25-7.3l(lHjn),7.49-7.58(2Hm),13.79(lH,bs)

CompoundNo. V-79:

3.94(3H,s), 7.05-7.07(lHjn), 727-7.32(2Hjn)

CompoundNo. V-80:

3.94(3H,s),7.12-7.18(2H/n),7.52-7.61(lffm)

CompoundNo. V-81 {solvent for measurementDMSO-dg)

3.60(3H,s), 7.37(lH,dJ=8.5Hz), 7.69(14fs), 7.82(lH,dJ=7.7Hz)

Compound No. V-82:

3.92(3H,s), 7.20(2H,s), 7.56(144^)

CompoundNo. V-83:

3.93(3H,s), 7.25(lH,dJ=10.4), 7.44(1^=8.0), 7.68(lH,dJ=l 1.7)

CompoundNo. V-84:

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3.93(3H,s), 721(lH,dJ=15.6), 7.45-7.48(lHjn), 7.68(lH,dJ=2.4Hz)

Compound No. V-85:

3.93(3H,s), 7.33(lH,dJ=5.7), 7.49-7.58(2ILm)

Compound No. V-86:

3.95(3H,s), 7.45-7.56(2Hjn)

Compound No. V-93/solvent for measurementDMSO-de)

3.58(3H,s), 3.74(6H,s), 7.52(2H,dJ=2.2Hz), 6.59(1 H,/J=2.2Hz), 13.63(lH,bs)

Compound No. V-96:(solvent for measurementiDMSO-cLj

3.59(3H,s), 3.73(3H,s), 3.82(3Iis), 7.62(lH,ddJ=2.5Hz,8.8Hz),

6.71(lHs), 7.16(lH,cU=8.5Hz), 13.76(lH,bs)

Compound No. V-134: (solvent for measurement: DMSO-de)

3.60(3H,s), 3.76(3H,s), 7.23(lH,dJ=9.1Hz), 7.43(1 H,dJ=2.8Hz), 7.54(11LddJ=2.8IIz, 9.1Hz), 13.84(lH,bs)

Compound No. V-l 70:(solvent for measurement:DMSO-dg)

3.58(3H,s), 6.10(2H,s), 6.78(lH,diU=l ,0Hz,6.2Hz), 6.89(1 HdJ=1.0Hz),

7.01(lH,dJ=6.2Hz), 13.63(lH,bs)

CompoundNo. V-179:(solventformeasurementDMSO-d6)

3.60(3H,s), 7.49(1 H,dJ=7.7Hz), 7.55(lH,dddJ=l.lHz,5.0Hz,7.7Hz), 8.05(lH,dfJ=1.9Hz,7.7Hz),8.62(lH,ddJ=l.lHz,5.0Hz)

CompoundNo. V-198:(solvent for measurement:DMSO-d6)

3.57(3H,s), 7.07-7.10(2Hjn), 7.63(lH,ddJ=1.9Hz,5.2Hz)

CompoundNo. V-259:(solvent for measuiementiDMSQ-dg)

1,09(3H,tJ=5.3Hz), 3.96(2H,qJ=5.3Hz), 7.32-7.37(2Hm), 7.45-7.54(3Hm), 9.51 (lH>bs)

CompoundNo. V-261 /solvent for measurementiDMSO-de)

7.36-7.53(5Hm), 7.82(1 H,Lj=42.9Hz)

Compound No. V-265/solvent for measurementDMSO-cf)

3.53(3H,s), 3.90(3H,s)

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Compound No. V-268{solvent for measurementDMSO-cf)

1.45(3H,t),3.91(3H,s),4.09(2H,q),7.04(2H,d),7.15(2H,d) [0261] <Formulation example 1> Wettable powder parts of the compound (1-1), 0.5 parts of polyoxyethylene octylphenyl ether, 0.5 parts of sodium β-naphthalene sulfonate formalin condensate, 20 parts of diatomaceous earth, and 69 parts of clay were mixed and pulverized to give a wettable powder.

<Formulation example 2> Flowable agent parts of roughly crushed compound (1-1) were dispersed in 69 parts of water, and added with 200 ppm of silicone AF-118N (trade name, manufactured by Asahi Kasei Corporation) while 10 simultaneously adding 4 parts of polyoxyethylene styryl phenyl ether sulfonate and 7 parts of ethylene glycol. After mixing for 30 minutes by high-speed mixer, the mixture was pulverized using a wet-type pulverizer to give a flowable agent.

<Formulation example 3> Emulsifiable concentrate parts of the compound (I-1), 60 parts of a mixture of xylene and isophorone (1:1 mixture), and 10 parts of a mixture of polyoxyethylene sorbitan alkylate, polyoxyethylene alkylaryl polymer, and alkylaryl sulfonate were mixed well to give an emulsifiable concentrate.

<Formulation example 4> Granules parts of the compound (I-1), 80 parts of extender in which talc and bentonite are mixed in ratio of 1 to 3, 5 parts of white carbon, and 5 parts of a mixture of polyoxyethylene sorbitan alkylate, polyoxyethylene alkylaryl polymer, and alkylaryl sulfonate were added with 10 parts of water. After kneading well, the resulting paste was extruded through a sieve (diameter; 0.7 mm) followed by drying. By cutting it to have length of 0.5 to 1 mm, granules were obtained.

Effect of the compounds of the invention is explained by way of following test examples.

<Test example 1> Test for determining herbicidal activity by paddy field soil treatment

A100 cm² wide plastic pot was filled with a paddy field soil and, after watering and shuffling, seeds of each of Echinochloa oryzicola, Monochoria vaginalis, and Scirpus juncoides Rocxb. were sowed and watered to a depth of 3 cm. On the next day, the wettable powder obtained in view of Formulation example 1 was diluted with water and applied on water surface. The application amount was 1000 g of effective component per hectare. After that, the plants

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[Table 72]

Index Number Herbicidal Effects

100% of herbicidal effects (complete death)

90% or more and less than 100% of herbicidal effects

80% or more and less than 90% of herbicidal effects

70% or more and less than 80% of herbicidal effects

60% or more and less than 70% of herbicidal effects

50% or more and less than 60% of herbicidal effects

40% or more and less than 50% of herbicidal effects

30% or more and less than 40% of herbicidal effects

20% or more and less than 30% of herbicidal effects

10% or more and less than 20% of herbicidal effects

0% or more and less than 10% of herbicidal effects

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Compound No.	Echinochloa oryzicola
I-l	10
1-2	10
1-3	10
1-4	9
1-5	10
1-9	8
1-10	10
141	10
1-14	10
1-16	9
1-19	10
1-27	10
1-41	8
1-43	10
1-50	10
1-51	10
1-52	10
1-53	10
1-54	10
1-55	10
1-56	10
1-57	10
1-58	10
1-59	10
1-60	10
1-61	8
1-63	10
1-64	10
1-65	10
1-66	10
1-67	10
1-68	10
1-71	10
1-72	10
1-73	10
1-74	10
1-75	10
1-76	10
1-77	10
1-78	10
1-79	10
1-80	10
1-81	10
1-82	8

Compound No.	Echinochloa oryzicola
1-83	10
1-84	10
1-85	10
1-86	10
1-87	9
1-88	10
1-89	10
1-90	9
1-91	10
1-92	10
1-93	8
1-96	8
1-99	10
1-105	10
1-106	10
1-107	10
1-108	10
1-109	10
1-110	10
1411	10
1-115	10
1-116	10
1-117	10
1-118	10
1-119	9
1-120	8
1-125	10
1-126	10
1-127	10
1-128	8
1-129	10
1-131	9
1-134	10
T135	10
1-136	9
1-137	10
1-138	10
1149	9
1-155	10
1-169	10
1-170	10
1-179	10
1-184	10
1-185	8

Compound No.	Echinochloa oryzicola
1-187	10
1-198	8
1-199	9
1-202	10
1-203	10
1-205	7
1-259	10
1-260	10
1-261	8
1-263	10
1-265	10
1-268	10
1-269	8
1-270	8
1-271	8
1-272	7
1-273	9
1-274	8
1-275	9
1-276	8
1-277	9
1-278	8
1-279	8
1-280	10
1-281	10
1-282	10
1-283	10
1-284	10
1-285	10
1-286	10
1-287	10
1-288	10
1-289	10
1-292	10
1-294	9
1-297	10
1-298	10
1-299	10
1-300	10
1-301	10
1-302	10
1-303	10
1-304	10
1-307	8

Compound	Echinochloa
No.	oryzicola
1-328	10
1-339	10
1-463	10
1-464	10
1-465	10
1-466	8
T468	10
1-469	10
1-470	10
1-471	10
1-473	8
1-474	10
1-475	10
1-476	10
1-477	10
1-478	10
1-479	10
1-480	10
III-50	10
ΙΠ-62	8
VI-1	10
VI-5	10
VI-6	10
VI-7	10
VI-65	10
VI-97	10
V-300	10
V-358	10
V-359	8
V-362	10
V-363	10
V-364	10
V-365	10
V-367	8
V-368	10
V-369	10
V-370	10
V-371	10

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Compound No.	Monochoria vaginalis	Compound No.	Monochoria vaginalis
1-1	10	1-82	10
1-2	10	1-83	10
1-3	10	1-84	10
1-4	9	1-85	10
1-5	10	1-86	10
1-9	8	1-87	10
1-10	10	1-88	10
Ill	10	1-89	10
1-14	10	1-90	10
1-16	9	1-91	10
119	10	1-92	10
1-27	10	1-93	10
1-41	8	1-94	10
1-43	10	1-96	10
1-47	10	1-99	10
1-50	10	1-105	10
1-51	10	1-106	10
1-52	10	1-107	10
1-53	7	1-108	10
1-54	10	1-109	10
1-55	10	IT10	10
1-56	10	I-111	10
1-57	10	1-115	10
1-58	10	1-116	10
1-59	10	1-117	10
1-60	10	1-118	10
1-61	10	1-119	10
1-62	8	1-120	10
1-63	10	1-125	10
1-64	10	1-126	10
1-65	10	1-127	10
1-66	10	1-128	9
1-67	10	1-129	10
1-68	10	1-131	10
1-71	10	1-134	10
1-72	10	1-135	10
1-73	10	1-136	10
1-74	10	1-137	10
1-75	10	1-138	10
1-76	10	1-149	10
1-77	10	1155	10
1-78	10	1169	10
1-79	10	1-170	10
1-80	10	1179	10
1-81	10	1-182	8

Compound No.	Monochoria vaginalis
1-183	10
1-184	10
1-185	9
1-187	10
1-189	10
1-198	10
IT99	8
1-202	10
1-203	10
1-204	8
1-205	10
1-259	10
1-260	10
1-261	10
1-262	8
1-263	10
T265	10
1-268	10
1-269	8
1-270	8
1-271	8
1-272	8
1-273	9
1-274	8
1-275	10
1-276	8
1-277	9
1-278	9
1-279	8
1-280	10
1-281	10
1-282	10
1-283	10
1-284	10
1-285	10
1-286	10
1-287	10
1-288	10
1-289	10
1-290	10
1-291	10
1-292	10
1-293	10
T294	9
1-297	10

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Compound No.	Monochoria vaginalis
1-298	10
1-299	10
1-300	10
1-301	10
1-302	10
1-303	10
1-304	10
1-306	9
1-307	9
1-308	8
1-328	10
1-339	10
1-462	10
1-463	10
1-464	10
1-465	10
1-466	10
1-467	10
1-468	10
1-469	10
1-470	10
1-471	10
1-472	10
1-473	10
1-474	10
1-475	10
1-476	10
1-477	10
1-478	10
1-479	10
11-50	8
11-267	8
III-50	10
III-62	10
VI-1	10
VI-5	10
VI-6	10
VI-7	10
VI-65	10
VI-97	10
V-291	8
V-300	10
V-358	10
V-359	10
V-360	10

Compound No.	Monochoria vaginalis
V-361	10
V-362	10
V-363	10
V-364	10
V-365	10
V-366	10
V-367	10
V-368	10
V-369	10
V-370	10
V-371	10

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[Table 76]
Compound No.	S. juncoides Rocxb.
I-l	10
1-2	10
1-3	10
1-4	10
1-5	10
1-9	8
1-10	10
1-11	10
1-14	10
1-16	10
1-19	10
1-27	10
1-41	10
1-43	10
1-47	10
1-50	10
1-51	10
1-52	10
1-53	10
1-54	10
1-55	10
1-56	10
1-57	10
1-58	10
1-59	10
1-60	10
1-61	10
1-63	10
1-64	10
1-65	10
1-66	10
1-67	10
1-68	10
1-71	10
1-72	10
1-73	10
1-74	10
1-75	10
1-76	10
1-77	10
1-78	10
1-79	10
1-80	10
1-81	10
1-82	10
1-83	10

Compound. No.	S. juncoides Rocxb.
1-84	10
T85	10
1-86	10
1-87	10
1-88	10
1-89	10
1-90	10
1-91	10
1-92	10
1-93	10
1-94	10
1-96	10
1-99	10
1-105	10
1-106	10
1-107	10
1-108	10
1-109	10
1-110	10
1-111	10
1-115	10
1-116	10
1-117	10
1-118	10
1-119	10
1-120	10
1-125	10
1-126	10
1-127	10
1-128	10
1-129	10
1-131	10
1-134	10
1-135	10
1-136	10
1-137	10
1-138	10
1-149	10
1-155	10
1169	10
1-170	10
1-179	10
1-182	9
1-183	10
1-184	10
1-185	9

Compound No.	S. juncoides Rocxb.
1-187	10
1-189	10
1-198	10
1-199	9
1-202	10
1-203	10
1-205	10
1-259	10
1-260	10
1-261	8
1-263	10
1-265	10
1-268	10
1-269	10
1-270	8
1-271	10
1-272	8
1-273	10
1-274	4
1-275	8
1-276	9
1-277	10
1-278	10
1-279	10
1-280	10
1-281	10
1-282	10
1-283	10
1-284	10
1-285	10
1-286	9
1-287	10
1-288	10
1-289	10
1-290	10
1-291	10
1-292	10
1-293	10
1-294	9
1-297	10
1-298	10
1-299	10
1-300	10
1-301	10
1-302	10
1-303	10

Compound No.	S. juncoides Rocxb.
1-304	10
1-307	8
1-328	10
1-339	10
1-462	10
1-463	10
1-464	10
1-465	10
1-466	10
1-467	10
1-468	10
1-469	10
1-470	10
1-471	10
1-472	8
1-473	8
T474	10
1-475	10
1-476	10
1-477	10
1-478	9
1-479	10
1-480	10
11-50	7
III-50	10 .
III-62	10
VI-1	10
VI-5	10
VI-6	10
VI-7	10
VI-65	10
VI-97	10
V-300	10
V-358	10
V-359	10
V-360	10
V-361	10
V-362	10
V-363	10
V-364	10
V-365	10
V-366	8
V-367	8
V-368	10
V-369	10
V-370	10
V-371	9

<Test example 2> Test for determining herbicidal activity by field soil treatment

A 80 cm² wide plastic pot was filled with a field soil and seeds of each of Echinochloa crus-galli, foxtail, Indian millet, and A. retroflexus were sowed and then covered with soil.

The

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Table 72 for determining the herbicidal effects. The results are shown in Table 77 to Table 80.

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Compound	Echinochloa	Compound	Echinochloa
No.	crus-galli	No.	crusgalli
I-l	8	1-92	9
1-2	10	1-93	7
1-3	10	1-98	7
1-4	9	1-99	8
1-5	10	1-105	9
1-9	7	1-106	10
1-10	10	1-107	8
Ill	10	1-109	9
1-14	10	1-110	7
1-16	9	1-111	9
1-19	8	1-115	9
1-27	10	1-116	10
1-41	9	1-117	10
1-43	10	1-118	10
1-50	10	1-119	8
1-51	10	1-120	8
1-52	10	1-125	7
1-53	8	1-127	10
1-54	10	1-128	8
1-55	10	1-129	9
1-56	10	1-131	9
1-57	10	1-134	10
1-58	10	T135	9
T60	10	1-137	10
T61	8	1-138	9
1-63	10	1-149	8
1-64	10	1-167	8
1-65	10	1-169	10
1-66	10	1-179	10
1-67	10	1-182	7
1-68	10	1-184	8
1-71	10	1-185	9
1-72	9	1-187	7
1-73	9	1-198	7
1-74	10	1-199	9
1-75	9	1-202	10
1-76	10	1-203	9
1-77	9	1-259	10
1-78	10	1-260	10
1-79	9	1-265	10
1-80	9	1-269	8
1-81	9	1-270	8
1-82	9	1-271	10
1-83	9	1-273	9
1-84	9	1-274	7
1-85	9	1-275	8
1-86	10	1-276	9
1-87	9	1-277	8
1-88	8	1-278	9
1-89	9	1-279	7
1-90	8	1-280	9
1-91	9	1-281	9

Compound No.	Echinocbloa crus-galli
1-282	10
1-283	9
1-284	10
1-285	10
1-286	10
1-287	10
1-288	10
1-289	9
1-292	7
1-294	9
1-297	10
1-298	7
1-299	9
1-302	7
1-303	9
1-304	10
1-307	7
1-339	8
1-471	7
1-474	7
1-475	7
1-476	7
1-477	9
1-478	9
1-479	9
1-480	8
VI-5	8
VI-7	10
V-300	7
V-365	7
V-368	7
V-369	7
V-370	7
V-371	9

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Compound No.	Setaria viridis
1-1	7
1-2	7
1-3	10
1-4	9
1-5	7
1-10	10
Ill	7
1-14	10
1-16	9
1-19	8
1-41	7
1-50	10
1-51	10
1-52	10
1-54	10
1-55	10
1-56	10
1-57	.10
1-58	8
1-63	10
1-66	10
1-67	10
1-68	10
1-71	6
1-72	10
1-73	⁸
1-74	7
1-75	7
1-76	9
1-77	9
1-79	10
1-80	9
¹⁸¹	7
1-82	9
1-83	9

Compound No.	Setaria viridis
1-84	9
1-85	9
1-86	9
1-87	6
1-89	8
1-91	10
1-92	9
1-93	6
1-98	7
1-99	6
1-105	7
1-109	6
Mil	7
1-116	9
1-117	7
1-118	9
1-127	8
1-128	9
1-129	10
1-131	7
1-134	10
1-136	8
1-137	9
1-155	7
1-169	10
1-179	10
1-202	9
1-260	5
1-265	10
1-269	9
1-270	7
1-271	10
1-276	9
1-277	8
1-278	9

Compound No.	Setaria viridis
1-280	8
1-281	9
1-282	10
1-283	8
1-284	8
1-285	10
1-286	9
1-288	9
1-289	7
1-294	7
1-297	9
1-298	7
1-299	10
1-303	9
1-304	9
VI-7	10
VI-65	7

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Compound No.	Abutilon theophrasti	Compound No.	Abutilon theophrasti	Compound No.	Abutilon theophrasti
1-1	9	1-83	10	1-167	10
1-2	10	1-84	10	1-169	9
T3	10	1-85	10	1-170	10
1-4	9	1-86	9	T179	10
1-5	10	1-87	9	1-182	10
1-10	10	1-88	10	1-183	10
1-11	9	1-89	10	1-184	10
1-14	10	1-90	10	1-185	10
1-16	9	1-91	10	1-187	9
1-27	10	1-92	10	1189	10
1-41	8	1-93	10	1-198	10
I-5O	10	1-94	10	1-199	10
1-51	10	1-96	10	1-202	9
1-52	10	1-98	7	1-259	8
1-53	10	1-99	9	1-260	10
1-54	10	1-105	9	1-261	10
1-55	10	1-106	10	1-263	8
1-56	10	1-107	10	1-265	10
1-57	10	1-108	8	1-268	8
1-58	10	1109	10	1-269	9
1-59	10	1-110	10	1-271	10
T60	10	1-111	9	1-273	7
1-61	10	1-115	9	1-274	8
1-63	10	1-116	10	1-275	10
1-64	10	1-117	10	1-276	10
1-65	10	1-118	9	1-277	7
T66	10	IT19	9	1-279	10
1-67	10	1-120	9	1-280	9
1-68	10	1-125	8	1-281	9
1-71	10	1-126	10	1-282	9
1-72	10	1-127	10	1-283	9
1-73	10	1-128	10	1-284	9
1-74	10	1-129	10	1-285	10
1-75	10	1-131	9	1-286	9
1-76	10	1-134	10	1-287	9
1-77	10	1-135	9	1-288	9
1-78	10	1-136	9	1-289	9
1-79	10	IT37	10	1-290	10
1-80	9	1-138	9	1-291	10
1-81	10	1-149	10	1-292	9
1-82	9	1-155	10	1-293	10

Compound No.	Abutilon theophrasti
1-294	9
1-297	9
1-298	10
1-299	10
T300	10
1-302	10
1-303	9
1-304	10
1-306	7
1-307	9
1-339	10
1-462	10
1-463	10
1-465	10
1-470	7
1-471	10
1-474	10
1-475	7
1-476	10
1-477	10
1-478	10
1-479	10
1-480	10
VI-1	10
VI-5	10
VI-6	9
VI-7	10
VI-65	10
V-61	8
V-300	9
V-358	10
V-361	10
V-364	7
V-365	10
V-368	10
V-369	7
V-370	10
V-371	10

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Compound No.	Amaranthus retroflexus
1-1	10
1-2	10
1-3	10
1-4	io
1-5	10
1-9	10
1-10	10
1-11	10
1-14	10
1-16	10
1-19	8
1-27	10
1-41	10
1-43	10
1-47	10
1-50	10
1-51	10
1-52	10
1-53	10
1-54	10
1-55	10
1-56	9
1-57	10
1-58	10
1-59	10
1-60	10
1-61	10
1-63	10
1-64	10
1-65	10
1-66	10
1-67	10
1-68	10
1-71	10
1-72	10
1-73	10
1-74	10
1-75	10
1-76	10
1-77	10
1-78	10
1-79	10
1-80	10
1-81	10

Compound No.	Amaranthus retroflexus
1-82	10
1-83	10
1-84	10
1-85	10
1-86	10
1-87	9
1-88	10
1-89	10
1-90	10
1-91	10
1-92	10
1-93	10
1-94	10
1-96	10
1-99	10
1-105	10
1-106	10
1-107	10
1-108	10
1-109	10
1-110	10
Illi	10
1-115	9
1116	10
1-117	10
1-118	10
1-119	10
1-120	10
1-125	10
1-126	10
1-127	10
1-128	10
1-129	10
1-131	10
1-134	10
1-135	10
1-136	9
1137	10
1-138	10
1-149	10
1-155	10
1-167	10
1-169	10
1-170	10

Compound No.	Amaranthus retroflexus
1-179	9
1-182	10
1-183	8
1-184	10
1-185	10
1-187	10
1189	10
1-198	10
1-199	10
1-202	10
1-203	7
1-259	10
1-260	10
1-263	10
1-265	10
1-268	10
1-269	10
1-270	10
1-271	10
1-272	8
1-273	10
1-274	7
1-275	10
1-276	10
1-277	8
1-278	10
1-279	10
1-280	10
1-281	10
1-282	10
1-283	10
1-284	10
1-285	10
1-286	10
1-287	10
1-288	10
1-289	10
1-290	8
1-291	8
1-294	10
1-297	10
1-298	10
1-299	10
1-300	10

Compound No.	Amaranthus retroflexus
1-302	10
1-303	10
1-304	10
1-306	10
1-307	10
1-308	10
T339	10
1-462	9
1-463	7
1-464	7
1-465	10
1-468	7
1-470	8
1-471	10
1-474	10
1-475	7
1-476	10
1-477	10
1-478	10
1-479	10
T480	10
VI-1	10
VI-5	10
VI-6	10
VI-7	10
VI-65	10
V-300	10
V-358	10
V-361	8
V-362	7
V-364	8
V-365	10
V-368	10
V-369	7
V-370	10
V-371	10

<Test example 3> Test for determining herbicidal activity by field foliage treatment

A 80 cm² wide plastic pot was filled with a field soil and seeds of each of Indian millet and

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A. retroflexus were sowed and then incubated for 2 weeks in a green house. The wettable powder produced with reference to the Formulation example 1 was diluted water, and applied from the air to entire body of the plant as foliage treatment by using a small sprayer in an amount of 1000 liters per hectare so that the effective component is 1000 g per hectare. After that, the plants were cultivated in a greenhouse, and on day 14 after the treatment, evaluation was made by the criteria described in Table 72 for determining the herbicidal effects. The results are shown in Table 81 to Table 84.

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Compound	Echinochloa	Compound	Echinochloa	Compound	Echinochloa	Compound	Echinochloa
No.	crus-galli	No.	crus-galli	No.	crus-galli	No.	crus-galli
I-l	8	1-81	10	1-169	9	1-300	9
1-2	9	1-82	10	1-170	10	1-302	10
1-3	9	1-83	10	1-179	10	1-303	8
1-4	9	1-84	9	1-182	8	1-304	10
1-5	10	1-85	9	1-184	10	1-328	7
1-9	10	1-86	9	1-185	10	1-339	9
1-10	8	1-87	9	1-187	8	1-463	7
1-11	9	1-88	8	1-198	10	1-465	8
1-14	9	1-89	9	1199	10	1-467	8
1-16	9	1-90	8	1-202	9	1-468	9
1-19	10	1-91	9	1-203	6	1-469	10
1-27	9	1-92	10	1-259	10	1-470	8
1-41	10	1-93	9	1-260	8	1-471	9
1-43	8	1-96	7	1-263	9	1-474	7
1-50	10	1-98	Ί	1-265	8	1-475	9
1-51	10	T99	9	1-268	7	1-476	7
1-52	10	1-105	10	1-269	10	1-477	9
1-53	8	1-106	10	1-270	9	1-478	8
1-54	10	1-107	7	1-271	10	1-479	9
1-55	10	1-109	10	1-272	6	1-480	9
1-56	10	1-110	9	1-273	10	III-50	10
1-57	10	Till	10	1-274	9	VI-1	10
Ί-58	10	1-115	10	1-275	9	VI-5	10
1-59	7	1-116	9	1-276	10	VI-6	8
1-60	10	1-117	9	1-277	10	VI-7	10
1-61	9	1-118	9	1-278	10	VI-65	9
1-63	10	1-119	9	1-279	9	VI-97	7
1-64	10	1-120	9	1-280	9	V-300	8
1-65	8	1-125	10	1-281	9	V-358	8
1-66	10	1-126	9	1-282	8	V-360	8
1-67	10	1-127	10	1-283	8	V-362	9
1-68	10	1-128	9	1-284	9	V-363	10
1-71	10	1-129	10	1-285	9	V-364	8
1-72	10	1-131	10	1-286	10	V-365	9
1-73	10	1-134	10	1-287	8	V-368	7
1-74	9	1-135	10	1-288	9	V-369	9
1-75	10	1-136	9	1-289	9	V-370	7
1-76	10	1-137	10	1-292	8	V-371	8
1-77	10	1-138	8	1-294	9
1-78	10	1-149	8	1-297	9
1-79	10	1155	9	1-298	10
1-80	10	1-167	10	1-299	8

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Compound No.	Setaria viridis
1-1	8
1-2	10
1-3	9
1-4	9
1-5	10
1-10	7
Ill	. 9
1-14	10
1-16	9
1-19	10
1-27	6
1-41	10
1-43	8
1-50	10
1-51	10
1-52	10
1-54	10
1-55	10
1-56	10
1-57	10 ..
1-58	10
1-60	9
1-63	10
1-66	10
1-67	10
1-68	8
1-71	9
1-72	10
Γ-73	10
1-74	9
1-75	10
1-76	9
1-77	10
1-78	10
1-79	10
1-80	7
1-81	10
1-82	10
1-83	10
1-84	10
1-85	10

Compound No.	Setaria viridis
1-86	9
1-89	10
1-90	7
1-91	10
1-92	10
1-93	9
1-105	7
1-109	7
1-116	9
1-117	9
1118	10
1-126	7
1-127	10
1-128	10
1-129	9
1-134	10
1-136	9
1-137	10
1-138	8
1-155	7.......
1-167	8
1-169	9
1-179	10
1-184	8
1-185	9
1-187	8
1-199	8
1-202	9
1-261	7
1-263	9
1-265	9
1-269	8
1-271	7
1-274	8
1-275	8
1-276	10
1-277	9
1-278	10
1-281	7
1-282	7
1-284	7

Compound No.	Setaria viridis
1-285	9
1-286	10
1-288	10
1-289	7
1-297	9
1-298	8
1-302	10
1-303	10
1-304	10
1-328	7
1-463	7
1-464	7
1-465	10
1-468	9
1-469	10
1-470	9
1-471	10
1-475	7
1-479	7
VI-1	10
VI-5	10
VI-6	10
VI-7	10
VI-65	7
VI-97	10
V-300	8
V-358	10
V-362	9
V-363	10
V-364	9
V-365	10
V-369	7

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Compound No.

M

1-2

1-3

1-4

1-5

1-9

1-10

I'll

1-14

1-16

1-19

1-27

1-41

1-43

1-47

1-50

1-51

1-52

1-53

T54

1-55

1-56

1-57

1-58

1-59

1-60

1-61

1-62

1-63

T64

T65

1-66

1-67

1-68

1-71

1-72

1-73

1-74

1-75

1-76

1-77

1-78

1-79

1-80

1-81

1-82

1-83

1-84

Abutilon theophrasti

Compound No.

1-85

1-86

1-87

1-88

1-89

1-90

1-91

T92

1-93

1-94

1-96

1-98

T99 1-105 1-106 1-107 1-108 1-109 1-110 Illi 1-115 1-116 1-117 1-118 1-119 1-120 1-125 1-126 1-127 1-128 1-129 1-131 1-134 1-135 1-136 1-137 1-138 1-149 1-155 1-167 1-169 1-170 1-179 1-182 1-183 1-184 1-185 1-187

Abutilon theophrasti io

Compound

No.

IT89

1-198

1-199

1-202

T203

1-205

1-259

1-260

1-261

T263

1-265

1-268

T269

1-270

1-271

1-272

1-273

1-274

1-275

1-276

1-277

1-278

1-279

1-280

1-281

1-282

1-283

1-284

1-285

1-286

1-287

1-288

T289

1-290

1-291

1-292

1-293

1-294

1-295

1-297

1-298

1-299

1-300

1-301

1-302

1-303

1-304

1-306

Abutilon theophrasti '

Compound No.

T307

1-308

1-328

1-339

1-462

1-463

1-464

1-465

T466

1-467

1-468

T469

T470

1-471

1-472

1-473

1-474

1-475

1-476

1-477

1-478

1-479

I-480

II-50

II-267

III-50

III-62

VI-1

VI-5

VI-6

VI-7 VI-65 VI-97 V-300 V-358 V-359 V-360 V-361 V-362 V-363 V-364 V-365 V-366 V-367 V-368 V-369 V-370 V-371

Abutilon theophrasti io

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Compound. No.	Aznaranthus retroflexus
I-l	10
1-2	10
1-3	9
1-4	9
1-5	10
1-9	10
1-10	10
1-11	10
1-14	10
1-16	10
1-19	10
1-27	9
1-41	10
1-43	10
1-47	10
1-50	10
1-51	10
1-52	10
1-53	10
1-54	10
1-55	10
1-56	10
1-57	10
1-58	10
1-59	10
1-60	10
1-61	10
1-62	10
1-63	10
1-64	10
1-65	10
1-66	10
1-67	10
1-68	10
1-71	10
1-72	10
1-73	10
1-74	10
1-75	10
1-76	10
1-77	10
1-78	10
1-79	10
1-80	10
1-81	10
1-82	10
1-83	10
1-84	10

Compound No.	Amaranthus retroflexus
1-85 1-86 1-87 1-88 T89 1-90 1-91 1-92 1-93 1-94 1-96 1-98 1-99 1-105 1-106 1-107 1-108 1-109 1-110 Mil 1-115 1-116 1-117 1-118 1-119 1-120 1-125 1-126 1-127 1-128 1-129 1-131 1-134 1-135 1-136 1-137 1138 1-149 1-155 1-167 1-169 1-170 1-179 1182 1183 1-184 1-185 1-187	10 10 10 10 10 10 10 10 10 10 10 8 10 10 10 10 10 9 9 10 10 8 8 10 10-- 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 8 10 10 9 10 10 10 10

Compound No.	Amaranthus retroflexus
1-189	10
1-198	10
1-199	9
1-202	9
1-203	10
1-204	7
T205	10
1-259	10
T260	10
1-261	10
1-263	10
1-265	10
1-268	10
1-269	10
1-270	10
1-271	10
1-272	10
1-273	10
1-274	9
1-275	9
1-276	10
1-277	10
1-278	10
1-279	10
1-280	10
1-281	9
1-282	8
1-283	8
1-284	9
1-285	8
1-286	10
1-287	10
1-288	10
1-289	10
1-290	10
1-291	10
1-292	10
1-293	10
1-294	8
1-295	8
1-297	8
1-298	10
1-299	10
1-300	10
1-301	10
1-302	10
1-303	10
1-304	10

Compound No.	Amaranthus retroflexus
1-306	7
T307	9
1-328	10
1-339	10
1-462	10
1-463	10
1-464	10
1-465	10
1-466	10
1-467	10
1-468	10
1-469	10
1-470	10
1-471	10
1-472	10
1-473	3
1-474	9
1-475	9
1-476	10
1-477	10
1-478	10
1-479	10
1-480	10
11-50	10
III-50	10
III-62	10
VI-1	10
VI-5	10
VI-6	10
VI-7	10
VI-65	10
VI-97	10
V-300	10
V-358	10
V-359	10
V-360	10
V-361	10
V-362	10
V-363	10
V-364	10
V-365	10
V-366	10
V-368	9
V-369	9
V-370	10
V-371	10

As a result of the tests, it was found that the compounds of the invention have an excellent herbicidal activity.

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1. A method of controlling the growth of undesirable weeds comprising applying a agrochemical composition, wherein the weeds belongs to a family selected from the group consisting of Onagraceae family, Ranunculaceae family, Polygonaceae family, Portulacaceae family, Caryophyllaceae family, Chenopodiaceae family, Amaranthaceae family, Brassicaceae family, Fabaceae family, Malvaceae family, Violet family, Rubiaceae family, Convolvulaceae family, Lamiaceae family, Scrophulariaceae family, Asteraceae family, Boraginaceae family, Asclepiadaceae family, Euphorbiaceae family, Geraniaceae family, Oxalidaceae family, Cucurbitaceae family, Poaceae family, Commelinaceae family, Equisetaceae family, Papaveraceae family, Cyperaceae family, Lythraceae family, Elatinacease family, Cyperacease family, Pontederiacease family, Alismatacease family, Potamogetonacease family, Eruocaulacease family, Apiacease family, Asteracease family, Commelinacease family, Characease family, Lemnacease family, Pontederiaceae family, Salvinia natans family, Araceae family, Haloragaceae family, Azollaceae family, Poaceate family, Apiaceae family, Hydrocharitaceae family, Cabpmbaceae family, and Lemnaceae family;

and the agrochemical composition comprises a triazine derivative or a salt thereof, wherein the triazine derivative is represented by Formula I, wherein

R¹ represents a hydrogen atom; a C1-C12 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C3-C6 cycloalkenyl group, a C3-C6 cycloalkyl C1-C6 alkyl group, a Ci-Ce haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a C3-C6

208

2018201082 16 Feb 2018 halocycloalkyl group, a C3-C6 halocycloalkyl Ci-Ce alkyl group, an amino Ci-Ce alkyl group, a nitro Ci-Ce alkyl group, a Ci-Ce alkylamino Ci-Ce alkyl group, a di(Ci-Ce alkyl)amino Ci-Ce alkyl group, a Ci-Ce alkylthio Ci-Ce alkyl group, a Cj-C'e alkylsulfinyl Cj-CV, alkyl group, a CiCe alkylsulfonyl Ci-Ce alkyl group, a Ci-Ce haloalkylthio Cj-C'e alkyl group, a Ci-Ce haloalkylsulfinyl Cj-Ce alkyl group, a Cj-Ce haloalkylsulfonyl Cj-Ce alkyl group, a Cj-Ce alkoxy Ci-Ce alkyl group, a hydroxy Ci-Ce alkyl group, a phenyl Cj-Ce alkoxy Ci-Ce alkyl group (phenyl in the group may be substituted with one substituent group selected from Substituent group oc or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group a), a Ci-Ce alkoxy Ci-Ce alkoxy Ci-Ce alkyl group, a C3-C6 cycloalkyloxy Ci-Ce alkyl group, a C3-C6 cycloalkyl Ci-Ce alkyloxy C1-C6 alkyl group, a phenyloxy Cj-CJ alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group cc), a phenylthio Cj-C'6 alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group oc), a phenylsulfinyl Ci-Ce alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a), a phenylsulfonyl Ci-Ce alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group cc), a C1-C6 haloalkoxy CiCe alkyl group, a phenyl group which may be substituted with one or more substituents selected from the Substituent group cc, a phenyl Ci-Ce alkyl group which may be substituted with one or more substituents selected from the Substituent group a, a phenyl C2-C6 alkenyl group which may be substituted with one or more substituents selected from the Substituent group cc, a phenyl C2-C6 alkynyl group which may be substituted with one or more substituents selected from the Substituent group cc, a C1-C6 alkoxyimino Ci-Ce alkyl group, a phenoxyimino Ci-Ce alkyl group which may be substituted with one or more substituents selected from the Substituent group oc, a di(Ci-C6 alkoxy)Ci-C6 alkyl group, a (R³¹R³²N-C=O)Ci-C6 alkyl group, a C1-C6 alkoxycarbonyl Ci-Ce alkyl group, a C1-C6 alkylcarbonyl Ci-Ce alkyl group, a Ci-Ce alkylcarbonyloxy Ci-Ce

209

2018201082 16 Feb 2018 alkyl group, a Ci-Ce alkylidene aminooxy Ci-Ce alkyl group, a formyl Ci-Ce alkyl group, a CiCe alkylthio Ci-Ce alkoxy Ci-Ce alkyl group, a Ci-Ce alkylsulfinyl Ci-Ce alkoxy Ci-Ce alkyl group, a Ci-C₆ alkylsulfonyl Ci-Ce alkoxy Ci-Ce alkyl group, a cyano Ci-Ce alkoxy Ci-Ce alkyl group, a cyano Ci-Ce alkyl group, a C2-C6 alkylidene amino group, a di(Ci-Cio alkyl)amino CiCe alkylidene amino group, a NR³¹R³² group, a Ci-Ce alkoxy group, a C2-C6 alkenyloxy group, a C2-C6 alkynyloxy group, a C3-C6 cycloalkyloxy group, a C3-C6 cycloalkyl Ci-Ce alkyloxy group, a C1-C6 haloalkoxy group, a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone], a Ci-Ce alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a], a Ci-Ce alkoxy Ci-Ce alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a], or a Ci-Ce alkoxy CiCe alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a];

R² represents a hydrogen atom, a Ci-Ce alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a Ci-Ce haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a Ci-Ce alkoxy Ci-Ce alkyl group, a C3-C6 cycloalkyloxy Ci-Ce alkyl

210

2018201082 16 Feb 2018 group, a di(Ci-C6 alkoxy) Ci-Ce alkyl group, a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a), a phenyl group which may be substituted with one or more substituents selected from the Substituent group a, a phenyl Ci-Ce alkyl group which may be substituted with one or more substituents selected from the substituent group a, a phenyl C2-C6 alkenyl group which may be substituted with one or more substituents selected from the Substituent group a, or a phenyl C2-C6 alkynyl group which may be substituted with one or more substituents selected from the substituent group a,

Y and Z represent an oxygen atom or a sulfur atom,

A represents any one of the following formula A-l to A-5,

A-1 A-2 A-3 A-4 A-5

R⁴ represents a hydroxyl group, O’M’ (M⁺ represents an alkali metal cation or an ammonium cation), an amino group, a halogen atom, a cyano group, an isothiocyanate group, an isocyanate group, a hydroxycarbonyloxy group, a C1-C6 alkoxycarbonyloxy group, a benzyloxycarbonyloxy group which may be substituted with a substituent group selected from Substituent group a, a C1-C6 alkoxy group, a C2-C6 alkenyloxy group, a C2-C6 alkynyloxy group, a C3-C6 cycloalkyloxy group, a cyanomethylene oxy group, a C3-C6 cycloalkyl C1-C6 alkyloxy group, a C1-C6 alkylcarbonyloxy group, a C1-C6 haloalkylcarbonyloxy group, a C2-C6 alkenylcarbonyloxy group, a C2-C6 haloalkenylcarbonyloxy group, a C2-C6 alkynylcarbonyloxy

211

2018201082 16 Feb 2018 group, a C2-C6 haloalkynylcarbonyloxy group, a Ci-Ce alkoxycarbonyl Ci-Ce alkoxy group, a phenyloxy group which may be substituted with one or more substituents selected from the Substituent group ot, a benzyloxy group which may be substituted with one or more substituents selected from the Substituent group a, a phenylcarbonyloxy group which may be substituted with one or more substituents selected from the Substituent group a, a benzylcarbonyloxy group which may be substituted with one or more substituents selected from the substituent group a, a phenylcarbonyl Ci-Ce alkyloxy group which may be substituted with one or more substituents selected from the Substituent group a, a C1-C10 alkylsulfonlyoxy group, a Ci-Ce haloalkylsulfonlyoxy group, a phenylsulfonyloxy group which may be substituted with one or more substituents selected from the Substituent group a, a benzylsulfonyloxy group which may be substituted with one or more substituents selected from the Substituent group a, a C1-C10 alkylthio group, a C1-C10 alkylsulfinyl group, a C1-C10 alkylsulfonyl group, a Ci-Ce haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a Ci-Ce haloalkylsulfonyl group, a C2-C6 alkenylthio group, a C2-C6 alkenylsulfinyl group, a C2-C6 alkenylsulfonyl group, a C2-C6 alkynylthio group, a C2-C6 alkynylsulfinyl group, a C2-C6 alkynylsulfonyl group, a phenylthio group which may be substituted with one or more substituents selected from the Substituent group a, a benzylthio group which may be substituted with one or more substituents selected from the Substituent group a, a phenylsulfinyl group which may be substituted with one or more substituents selected from the Substituent group a, a benzylsulfinyl group which may be substituted with one or more substituents selected from the Substituent group a, a phenylsulfonyl group which may be substituted with one or more substituents selected from the substituent group a, a benzylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group a, a C1-C10 alkylamino group, a di(Ci-Cio alkyl)amino group, a C1-C6 alkoxycarbonylamino group, a C1-C6 alkoxy group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to

212

2018201082 16 Feb 2018 identical or different substituents selected from the Substituent group a), a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a), or a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a),

Ai represents a group represented by the following formula

R⁵ /R⁶ —c[Xd

R⁷ —N— [Χ₂]

A2 represents a group represented by the following formula

^R \ z^r9	0 II	⁽0_)n	_r33 I
—c—	—c—	—s—	—0—	—N—

[X3] [ X4 ] [ X5 ] [ X₆ ] [ x 7 ]

A3 represents a group represented by the following formula

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R³⁴ _{r35 r}36 —c— [Xe] [Xs] n represents 0, 1, or 2,

R⁵, R⁶, R⁸, R⁹, R³⁵ and R³⁶ each independently represent a hydrogen atom or a Ci-Ce alkyl group, wherein, R⁵ and R⁸ may be joined together to form a C2-C5 alkylene chain or a C2C5 alkenylene chain, and may form a ring together with adjacent carbon atoms, and R⁵ and R³⁵may be joined together to form a C1-C5 alkylene chain to form a ring with adjacent carbon atoms,

R⁷, R³³, and R³⁴ each independently represent a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, or a C1-C6 alkoxy group,

R¹⁴, R¹⁵, R¹⁶, and R¹⁷ each independently represent a hydrogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, or a benzyl group which may be substituted with one or more substituents selected from the Substituent group a,

R¹⁸ represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyanomethyl group, or a benzyl group,

R²⁰ represents a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, or a C3-C6 cycloalkyl C1-C6 alkyl group,

R²¹ represents a hydrogen atom, a C1-C6 alkyl group, or a halogen atom,

R²³ represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group, a C1-C10 alkylthio group, a C1-C10 alkylsulfinyl group, a C1-C10 alkylsulfonyl group, a phenylthio group which may be substituted with one or more substituents selected from the Substituent group a, a benzylthio group which may be substituted with one or more substituents selected

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2018201082 16 Feb 2018 from the Substituent group a, a phenylsulfinyl group which may be substituted with one or more substituents selected from the Substituent group a, a benzylsulfinyl group which may be substituted with one or more substituents selected from the Substituent group a, a phenylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group ct, or a benzylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group a;

R²⁴ represents a hydrogen atom, a halogen atom, a cyano group, a Ci-Ce alkyl group, a C3-C6 cycloalkyl group, or a Ci-Ce alkoxycarbonylamino group;

r25 _rep_resent_{s a} Ci-Ce alkoxycarbonyl group, a cyano group, or a nitro group;

R³¹ and R³² each independently represent a hydrogen atom, a Ci-Ce alkyl group, a phenyl group which may be substituted with one or more substituents selected from the substituent group a, a benzyl group which may be substituted with one or more substituents selected from the Substituent group a, a Ci-Ce alkoxy Ci-Ce alkyl group, a Ci-Ce alkylcarbonyl group, a CiC10 alkylthio carbonyl group, a Ci-Ce alkoxycarbonyl group, a Ci-Ce haloalkyl group, a C3-C6 cycloalkyl group, a C3-C6 cycloalkyl C1-C6 alkyl group, a C1-C6 alkylsulfonyl group,a phenylsulfonyl group which may be substituted with one or more substituents selected from the substituent group a, a benzylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group a, a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group a), or a C1-C6 alkyl group substituted with a heterocyclic group in which the heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents

215

2018201082 16 Feb 2018 selected from the Substituent group cc), wherein, R³¹ and R³² may be joined together to form a 5to 6-membered ring with adjacent nitrogen atom, and the one or more carbon atoms in the ring may be substituted with a sulfur atom and/or an oxygen atom;

wherein, Substituent group a represents a group selected from the group consisting of:

a halogen atom; a hydroxyl group, a Ci-Ce alkyl group, a C3-C6 cycloalkyl group, a C3-C6 cycloalkyl C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a C3-C6 halocycloalkyl group, a C3-C6 halocycloalkyl C1-C6 alkyl group, a C1-C6 alkoxy group, a C3-C6 cycloalkyloxy group, a C2-C6 alkenyloxy group, a C2-C6 alkynyloxy group, a C1-C6 alkylcarbonyloxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, an amino group, a C1-C6 alkylcarbonylamino group, a mono(Ci-C6 alkyljamino group, a di(Ci-C6 alkyljamino group, a hydroxy C1-C6 alkyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkylthio C1-C6 alkyl group, a C1-C6 alkylsulfinyl C1-C6 alkyl group, a C1-C6 alkylsulfonyl C1-C6 alkyl group, a C1-C6 haloalkylthio C1-C6 alkyl group, a C1-C6 haloalkylsulfinyl C1-C6 alkyl group, a C1-C6 haloalkylsulfonyl C1-C6 alkyl group, a cyano C1-C6 alkyl group, a C1-C6 alkoxy C1-C6 alkoxy group, a C3-C6 cycloalkyl C1-C6 alkyloxy group, a C1-C6 haloalkoxy C1-C6 alkoxy group, a cyano C1-C6 alkoxy group, a C1-C6 acyl group, a C1-C6 alkoxyimino C1-C6 alkyl group, a carboxyl group, a C1-C6 alkoxycarbonyl group, a carbamoyl group, a mono(Ci-C6 alkyljaminocarbonyl group, a di(Ci-C6 alkyljaminocarbonyl group, a nitro group, a cyano group, a phenyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group β), a heterocyclic group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group β), a heterocyclic oxy group comprising 2 to 10

216

Claims

R¹ and R² are independently selected from Cl-Cl
2 alkyl, or phenyl substituted with one or more substituents selected from the substituent group a, wherein substituent group a is a halogen atom;

R⁴ is hydroxyl; and Y and Z are both oxygen.
3. The method of claim 2, wherein:

R¹ is a phenyl substituted with 1 to 5 halogen atoms selected from chloro or fluoro; and

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R² is methyl, ethyl or propyl.
4. The method of claim 2, wherein

R¹ is phenyl, substituted at any of carbon of the phenyl ring with fluoro and

R² is methyl.
5. The method of claim 1, wherein the agrochemical composition further comprises an additional agrochemically active component, wherein the additional agrochemically active component is herbicide selected from the group consisting of Acetyl Co A carboxylase (ACCase) inhibition type herbicide, an Acetolactate synthase (ALS) inhibition type herbicides, a Herbicides 1 for photosystem II photosynthesis inhibition, Herbicides 2 for photosystem II photosynthesis inhibition, Photosystem I radical generation type herbicides, Protoporpyrinogen oxidase (PPO) inhibition herbicides, Phytoene desaturase (PDS) inhibition herbicides, Carotenoid biosynthesis inhibition, EPSP synthase synthesis inhibition (aromatic amino acid biosynthesis inhibition) type herbicides, Glutamine synthesis inhibition herbicides, Dihydropteroic acid (DHP) inihibition herbicides, Microtubule association inhibition type herbicides, Mitosis/Microtubule tissue formation inhibition herbicides, very long-chain fatty acid (VLCFA) synthase inhibition herbicides, Cellulose synthesis inhibition herbicides, Uncoupler (cell membrane distraction) type herbicides, Lipid bioxynthesis (excluding ACCase inhibition) inhibition herbicides, Auxin synthesis inhibition herbicides, and Auxin transport inhibition type herbicides.
6. The method of claim 1, wherein the agrochemical composition further comprises an additional agrochemically active component, wherein the additional agrochemically active component is a plant growth controlling compound selected from the group consisting of 1Methylcyclopropene, 1-naphthylacetamide, 2,6-diisopropylnaphthalene, 4-CPA,

218

2018201082 16 Feb 2018 benzylaminopurine, ancymidol, aviglycine, carvone, chlormequat, cloprop, cloxyfonac, cloxyfonac-potassium, cyclanilide, cytokinins, daminozide, dikegulac, dimethipin, ethephon, ethychlozate, flumetralin, flurenol, flurprimidol, forchlorfenuron, gibberellin acid, inabenfide, indol acetic acid, indol butyric acid, maleic hydrazide, mefluidide, mepiquat chloride, n-decanol, paclobutrazol, prohexadione-calcium, prohydrojasmon, sintofen, thidiazuron, triacontanol, trinexapac-ethyl, uniconazole, uniconazole-P, and ecolyst.
7. The method of claim 1, wherein the agrochemical composition further comprises an additional agrochemically active component, wherein the additional agrochemically active component is a safener selected from the group consisting of benoxacor, furilazole, dichlormid, dicyclonone, DKA-24 (N1 ,N2-diallyl-N2-dichloroacetylglycinamide), AD-67 (4-dichloroacetyl1 -oxa-4-azaspiro[4.5]decane), PPG-1292 (2,2-dichloro-N-( 1,3-dioxan-2-ylmethyl)-N-(2propenyl)acetamide), R-29148 (3-dichloroacetyl-2,2,5-trimethyl-l,3-oxazolidine), cloquintcetmexyl, naphthalic anhydride (1,8-naphthalic anhydride), mefenpyr-diethyl, mefenpyr, mefenpyrethyl, fenchlorazole-ethyl, fenclorim, MG-191 (2-dichloromethyl-2-methyl-l,3-dioxane), cyometrinil, flurazole, fluxofenim, isoxadifen, isoxadifen-ethyl, mecoprop, MCPA, daimuron, 2,4-D, MON4660, oxabetrinil, cyprosulfamide, lower alkyl substituted benzoic acid, and TI-35.
8. The method of claim 1, wherein the agrochemical composition further comprises an additional agrochemically active component, wherein the additional agrochemically active component is a plant disease control agent selected from the group consisting of Nucleic acid biosynthesis inhibitor, Mitosis and cell differentiation inhibitor, Respiration inhibitor, Amino acid and protein synthesis inhibitor, signal transduction pathway inhibitor, Lipid and cell membrane synthesis inhibitor, Sterol biosynthesis inhibitor, Glucan biosynthesis inhibitor, Melanine synthesis inhibitor, plant disease resistance inducer, Microorganisms and products of microorganisms.

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2018201082 16 Feb 2018
9. The method of claim 1, wherein the agrochemical composition further comprises an additional agrochemically active component, wherein the additional agrochemically active component is a pesticide, a acaricid or a nematocide selected from the group consisting of Acetylcholine esterase inhibitor, GAB A receptor (chloride channel) inhibitor, sodium channel modulator, Nicotinic acetylchloine receptor agonist/antagonist, Nicotinic acetylchloine receptor allosteric activator, Chloride channel activator, Juvenile hormone, Feeding inhibitor, Mite growth controlling agent, ATP biosynthesis enzyme inhibitor, Uncoupler, nicotinic acetylchloine channel blocker, Chitin biosynthesis inhibitor, Molting inhibitor, Ecdysone agonist, Octopamine agonist, Mitochondrial electron transport chain (complex III) inhibitor, Mitochondrial electron transport chain (complex I) inhibitor, Sodium channel inhibitor, Lipid biosynthesis inhibitor, Mitochondrial electron transport chain (complex IV) inhibitor, Neuronal inhibitor, Aconitase inhibitor, and agent on ryanodine receptor.
10. The method of claim 1, wherein the weeds are water seeds and belongs to a family selected from the group consisting of Pontederiaceae family, Salvinia natans family, Araceae family, Haloragaceae family, Azollaceae family, Scrophulariacease family, Amaranthaceae family, Poaceate family, Apiaceae family, Hydrocharitaceae family, Cabpmbaceae family, and Lemnaceae family.
11. The method of claim 1, wherein the weeds are at a location selected from the group consisting of a slope of a levee, a riverbed, a shoulder and a slope of a road, a railway site, park spaces, grand, a parking lot, an airport, a factory and a storage facility, a non-crop land and vacant lots in city, an orchard, a pasture land, a grass land, and a forest land.
12. The method of claim 1, wherein the agrochemical composition applied at a location where an agrohorticultural plant is cultivated.
13. The method of claim 12, wherein the agrohorticultural plant is cultivated in a farmland.

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2018201082 16 Feb 2018
14. The method of claim 12, wherein the agrohorticultural plant is cultivated in a field or a paddy field.
15. The method of claim 12, wherein the agrochemical composition was applied during foliage treatment, soil treatment, seed dressing treatment, soil blending treatment, soil treatment before sowing, treatment at the time of sowing, soil treatment after sowing, soil covering and blending treatment at the time of sowing, or soil treatment before and after sowing for no-tillage farming of a field for cultivating the agrohorticultural plant.
16. The method of claim 12, wherein the agrohorticultural plant is selected from the group consisting of crop, vegetable, fruit, mandarin, nut, berry, tree, grass, grass, oil crop, flower, fescue, and foliage plant.
17. The method of claim 12, wherein the agrohorticultural plant is given resistance to a herbicide.
18. The method of claim 17, wherein the agrohorticultural plant has resistance to HPPD inhibitor, ALS inhibitor, EPSP synthase inhibitor, glutamine synthase inhibitor, acetyl CoA carboxylase inhibitor, or PPO inhibitor.
19. The method of claim 17, wherein the agrohorticultural plant has one or more traits selected from the group consisting of having herbicides-resistant gene, having pesticidal insectresistant gene, having anti-pathogenic substance-producing gene, having modified oil components, and producing enhanced amount of amino acid are combined.