[go: up one dir, main page]

WO2007011022A1 - Dérivé de 3-(isoquinoline-1-yl)quinoline - Google Patents

Dérivé de 3-(isoquinoline-1-yl)quinoline Download PDF

Info

Publication number
WO2007011022A1
WO2007011022A1 PCT/JP2006/314478 JP2006314478W WO2007011022A1 WO 2007011022 A1 WO2007011022 A1 WO 2007011022A1 JP 2006314478 W JP2006314478 W JP 2006314478W WO 2007011022 A1 WO2007011022 A1 WO 2007011022A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
different
atom
alkyl
same
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2006/314478
Other languages
English (en)
Japanese (ja)
Inventor
Hiroyuki Ito
Hiroyuki Komai
Kota Fujiwara
Harukazu Tanaka
Yasushi Tamagawa
Fumie Kajino
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsui Chemicals Agro Inc
Original Assignee
Sankyo Agro Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sankyo Agro Co Ltd filed Critical Sankyo Agro Co Ltd
Publication of WO2007011022A1 publication Critical patent/WO2007011022A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings

Definitions

  • the present invention relates to a 3- (isoquinoline-1-yl) quinoline derivative or a salt thereof, and an agrochemical composition containing them as an active ingredient.
  • Patent Document 1 and Patent Document 2 a 6-aryl phenanthridine compound in which a cyclohexane ring is formed between the 3-position and 4-position of a dihydroisoquinoline ring is used as a PDE4 inhibitor.
  • Patent Document 3 describes a 6-arylfuroisoquinoline compound that forms a dihydrofuran ring between positions 7 and 8 of the dihydroisoquinoline ring as an entry inhibitor. Forces There is no description of 3-dihydroisoquinoline-1-ylquinoline derivatives in which the isoquinoline ring is not condensed with another ring, and there is no description of the agricultural chemical composition (agricultural and horticultural fungicide).
  • Non-Patent Documents 1 to 4 describe the synthesis of 3- (isoquinoline-1-yl) quinoline compound, but do not describe an agrochemical composition (agricultural and horticultural fungicide). .
  • Patent Document 1 Pamphlet of International Publication No. 00Z42019
  • Patent Document 2 Pamphlet of International Publication No. 02Z06270
  • Patent Document 3 JP 2003Z 171381
  • Non-Patent Document 1 Indian Journal of Chemistry, 1969, 7 (10), 1010-1016
  • Non-Patent Document 2 Indian Journal of Chemistry, 1970, 8 (6), 505-508
  • Non-Patent Document 3 Indian Journal of Chemistry, 1985, 24B (7), 737-746
  • Non-Patent Document 4 Indian Journal of Chemistry, 1986, 25B (10), 1072-1078
  • An object of the present invention is to have an excellent bactericidal activity against various plant diseases.
  • An object of the present invention is to provide 3 (isoquinoline 1-yl) quinoline derivatives or salts thereof useful as active ingredients, and an agrochemical composition containing them as active ingredients.
  • the present invention provides 3 (isoquinoline 1-yl) quinoline derivatives or salts thereof, which are useful as active ingredients of agricultural chemical compositions, and agricultural chemical compositions containing them as active ingredients.
  • the object of the present invention is to have an excellent bactericidal activity against various plant diseases and to be useful as an active ingredient of an agrochemical composition.
  • 3 isoquinoline 1yl
  • quinoline derivative or a salt thereof and effective It is providing the agrochemical composition contained as a component.
  • the present invention can be used as an agrochemical composition, in particular, as an agricultural and horticultural fungicide, and exhibits excellent effects on various phytopathogenic fungi, particularly rice blast, which do not damage the host plant.
  • the present invention provides a general formula
  • Ring A and ring B may be the same or different
  • An optionally substituted benzene ring an optionally substituted C 1 -C cycloalkyl ring (
  • cycloalkyl ring may be partially unsaturated); or may be substituted, the same or different 1 to 4 identical, with the group forces also comprising oxygen, nitrogen and sulfur forces selected Or a 5- to 6-membered heteroaryl ring containing different ring-constituting heteroatoms, wherein the heteroaryl ring may be partially hydrogenated,
  • R 3 and R 4 may be the same or different
  • a group force that may be substituted with 1 to 3 substituents of the same or different ones selected from c to c alkyl groups; hydroxyl groups; rho, rogen atoms, c to c alkoxy groups, and phenoxy groups.
  • the group force may also be substituted with 1 to 3 substituents of the same or different one selected from a ⁇ C alkoxy group; a norogen atom, a C 1 -C alkoxy group and a phenoxy group.
  • ⁇ C alkylthio group consisting of a norogen atom, a C ⁇ C alkoxy group and a phenoxy group
  • Group power may also be substituted with the same or different 1 to 3 substituents selected C ⁇
  • Group power as basic force C 1 -C cycloalkyloxy group which may be substituted with the same or different 1 to 3 substituents selected; a nitrogen atom, a C 1 -C alkoxy group and a phenol
  • Phenoxy group force Group power C 1 -C alkenyl group optionally substituted by 1 to 3 selected or different substituents; a norogen atom, a C 1 -C alkoxy group and a phenyl group
  • Noxy group strength group power is selected by the same or different 1 to 3 substituents C to c-alkoxy group; a norogen atom, c to c alkoxy group and
  • Group power also may be substituted with the same or different 1 to 6 substituents selected; aryl group; a norogen atom, optionally substituted with 1 to 3 different halogens C -C alkyl group, C -C alkoxy group, 1 to 2 identical or different (amino group, nitro group, cyano optionally substituted by DC -C alkyl or acyl)
  • a mercapto group and a c to c alkylthio group force are also selected, the same or different
  • Aralkyl group which may be substituted with 1 to 6 substituents; halogen atom, C to C alkyl group which may be substituted with 1 to 3 different halogens, C to C
  • a group force selected from 1 to 6 substituents selected from the same or different may be an aralkylthio group; an acyl group; an acyloxy group; an acylthio group; or a cyano group, or
  • RR 2 , R 3 and R 4 Two of RR 2 , R 3 and R 4 are taken together to form a halogen atom, c-c alkyl.
  • a C 1 -C cycloalkyl ring optionally substituted with 1 to 3 substituents (wherein
  • the chloroalkyl ring may contain 1 to 3 heteroatoms selected from the group forces of oxygen, nitrogen and sulfur), or R 1 and R 2 ; or R 3 and R 4 are , Taken together to represent an oxo group, or R 1 and R 2 ; or R 3 and R 4 taken together represent a methylene group, or R 1 and R 3 or R 4 ; or R 2 and R 3 or R 4 together represent a single bond, Q is a nitrogen atom or a formula N—R 5 group (wherein R 5 is a hydrogen atom; a hydroxyl group, the same or different 1 to An amino group optionally substituted by two C 1 -C alkyl or acyl; Halogen atoms, c-c alkoxy groups and phenoxy groups
  • Atoms, c to c alkoxy groups, and phenoxy group forces are the same or selected
  • a C 1 -C alkoxy group optionally substituted with 1 to 3 different substituents
  • a C 1 -C alkylsulfinyl group optionally substituted with 1 to 3 substituents;
  • a C to C alkoxy group the same or different 1 to 2 C to C alkyl or
  • An amino group optionally substituted by a sil, a nitro group, a cyano group, a hydroxyl group, a mercapto group, and
  • Substituted with a group may be an aralkyloxy group; an acyl group; an acyloxy group; tri- (C
  • X may be the same or different when n is an integer from 2 to 4
  • a halogen atom from the group consisting of a norogen atom, a C to C alkoxy group and a phenoxy group C 1 -C alkyl optionally substituted with 1 to 3 identical or different substituents selected
  • 1 6 kill group selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group
  • 3 6 kill group selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group
  • a C 1 -C alkyl group optionally substituted with one or different 1 to 3 substituents;
  • An aryl group which may be substituted with 1 to 6 substituents; a halogen atom, a C to C alkyl group and a C to C alkoxy group which may be substituted with the same or different 1 to 3 halogens Group force selected heteroaryl group optionally substituted with 1 to 6 substituents of the same or different selected; a nonogen atom, a C to C alkoxy group and a phenoxy group
  • C group power is selected C-C alkoxy group which may be substituted with the same or different 1 to 3 substituents selected; group atom consisting of a nonogen atom, C-C alkoxy group and phenoxy group selected C 1 -C alkylthio group which may be substituted with the same or different 1 to 3 substituents; the same or different 1 to 3 group forces consisting of a nonogen atom, a C 1 -C alkoxy group and a phenoxy group are also selected It may be substituted with 1 substituent group, ie, a C alkyl sulfier group; a nitrogen atom, a C 1 to C alkoxy group, and a phenoxy group group power of the same or different selected 1 to 3 substituent groups Optionally substituted C 1 -C alkyl sulfol group; one or two C 2 -C alkyls which are the same or different
  • acyl group may be an amino group; an acyl group; a cyan group; or C
  • Y may be the same or different when m is an integer of 2 to 6,
  • a halogen atom from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group
  • 1 6 kill group selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group
  • 3 6 kill group selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group
  • a C 1 -C alkyl group optionally substituted with one or different 1 to 3 substituents;
  • An aryl group which may be substituted with 1 to 6 substituents; a halogen atom, a C to C alkyl group and a C to C alkoxy group which may be substituted with the same or different 1 to 3 halogens Group force selected heteroaryl group optionally substituted with 1 to 6 substituents of the same or different selected; a nonogen atom, a C to C alkoxy group and a phenoxy group
  • C group power is selected C-C alkoxy group which may be substituted with the same or different 1 to 3 substituents selected; group atom consisting of a nonogen atom, C-C alkoxy group and phenoxy group selected C 1 -C alkylthio group which may be substituted with the same or different 1 to 3 substituents; the same or different 1 to 3 group forces consisting of a nonogen atom, a C 1 -C alkoxy group and a phenoxy group are also selected It may be substituted with 1 substituent group, ie, a C alkyl sulfier group; a nitrogen atom, a C 1 to C alkoxy group, and a phenoxy group group power of the same or different selected 1 to 3 substituent groups Optionally substituted C 1 -C alkyl sulfol group; one or two C 2 -C alkyls which are the same or different
  • 1 6 16 substituted with a kill group or an acyl group may represent an amino group; an acyl group; a cyan group; or a hydroxyl group;
  • n an integer of 0 to 4
  • n an integer of 0 to 6
  • a bond containing a dotted line represents a single bond or a double bond
  • the bond including Q and the dotted line is a single bond
  • the bond including the other dotted line represents a single bond
  • cyclopropane ring cyclobutane ring, cyclopentane ring, cyclopentene ring, cyclohexane ring, cyclohexene ring, cycloheptane ring or cyclooctane.
  • a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclopentene ring, a cyclohexane ring or a cyclohexene ring and particularly preferably a cyclopentane ring or a cyclohexane ring. It is.
  • the “5- to 6-membered heteroaryl ring” of ring A and ring B (wherein the heteroaryl ring may be partially hydrogenated) is, for example, a furan ring, a dihydrofuran ring, Thiophene ring, dihydrothiophene ring, pyrrole ring, oxazole ring, isoxazole ring, dihydroisoxazole ring, thiazole ring, isothiazole ring, imidazole ring, virazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring , A pyridine ring, a pyrazine ring, a pyridazine ring, an oxazine ring or a dihydrooxazine ring, preferably a furan ring, a thiophene ring, an oxazole
  • a “C to C alkyl group” (an alkyl group having 1 to 6 carbon atoms) such as R 1 or the like
  • C-c alkyl moiety such as "c-c alkoxy group” means either a straight or branched chain
  • a kill group (C-C alkyl group), and even more preferably a straight chain or straight chain having 1 to 3 carbon atoms.
  • Group or propyl group and most preferably a methyl group or an ethyl group.
  • a “C to C alk group” such as R 1 (alkal having 2 to 6 carbon atoms).
  • bur group proper 1-l-yl group, aryl group, iso-propyl group, but-1-ene-1-yl group, but-2-ene-1-yl group, but- yl 3—1—yl group, 2—methylpropylene 2—ene 1—yl group, 1 methylproper 2—ene 1—yl group, penter 1—ene 1—yl group, penter 2—one 1-yl group, penter 3-ene 1-yl group, penta-4-ene 1-yl group, 3-methylbuta-2-ene 1-yl group, 3-methylbutane 3-ene 1 Hexyl group, hexene 1-yl group, hexene 2-eneyl group, hexase-3 ene-1-yl group, hexene 4-ene-1-yl group, hexene-5-eneyl group, 4-methylpenter-3 1-yl group
  • bur group proper 1-l-yl group, aryl group, iso-prop
  • Group particularly preferably a vinyl group or an aryl group.
  • a “C to C alkyl group” such as R 1 (an alkyl having 2 to 6 carbon atoms).
  • ⁇ c-c alkynyl moiety '' such as ⁇ c-c alkynyloxy group '' is linear or
  • Etul Proper 1 in 1 group, Proper 2-in 1 group, Butter 1 in 1 group, Butter 3 in 1 group, 1 Methyl prop 2-in 1 1-yl Group, penta-1-1-in-1-yl group, penta-1-in-1-yl group, hex-1-in-1-yl group, hexer-5-in-1-yl group, and preferably Etul group or proper 2-in-1yl group (propargyl group), particularly preferably an ethur group.
  • the “aryl moiety” such as “aryl group” or “aryloxy group” such as R 1 is an aromatic hydrocarbon group having 6 to 14 carbon atoms, such as phenyl group, 1 naphthyl group. It may be a thiol group, a 2-naphthyl group, an anthracyl group, a phenanthryl group, or a acenaphthyl group, preferably a phenyl group, a 1-naphthyl group, or a 2-naphthyl group, and particularly preferably. Is a phenol group.
  • a “heteroaryl moiety” such as a “heteroaryl group” or “heteroaryloxy group” such as R 1 is partially hydrogenated by condensation with a benzene ring or the like.
  • Oxygen atoms, nitrogen atoms and sulfur nuclear power groups that may be converted to 5- to 7-membered heteroaryl groups containing 1 to 4 identical or different ring heteroatoms, such as furyl Group, phenyl, pyrrolyl, oxazolyl, isoxazolyl, dihydroisoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, birazyl Group, an azepinyl group or an oxazepine group, preferably a furyl group, a chenyl group, an oxazoly
  • Pyridyl group or virazyl group particularly preferably furyl group, -Group or pyridyl group.
  • benzene ring and condensed heteroaryl groups include, for example, benzofuranyl group, isobenzofuranyl group, benzochelyl group, indolyl group, isoindolyl group, indazolyl group, benzoxazolyl group, benzoisoxazolyl group.
  • benzothiazolyl group benzothiazolyl group, benzothiazolyl group, benzoxadiazolyl group, benzothiadiazolyl group, benzotriazolyl group, quinolyl group, isoquinolyl group, cinnolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, naphthyridinyl group Group, prill group, pteridyl group, carbazolyl group, carbolyl group, ataridyl group, 2-ataridyl, 3-ataridyl, 4-ataridyl, 9-attaridyl, phenoxazyl group, phenothiazyl group or phenazyl group, preferably , Benzofuryl group, benzothia There Le group - Lil group, quinolyl group, quinazolinyl group, or Nafuchiriji
  • Particularly preferred is a quinazolyl group or a naphthylyl group.
  • aralkyl moiety such as “aralkyl group” or “aralkyloxy group” such as R 1 is one or more hydrogen atoms of the “C 1 -C alkyl group”.
  • the atom is
  • a benzyl group for example, a benzyl group, a 1 naphthylmethyl group, a 2-naphthylmethyl group, an anthracenylmethyl group, a phenanthrylmethyl group, an acenaphthylmethyl group, a diphenylmethyl group, a 1 phenethyl group.
  • 2-phenethyl group 1 (1-naphthyl) ethyl group, 1- (2-naphthyl) ethyl group, 2- (1naphthyl) ethyl group, 2- (2naphthyl) ethyl group, 3-phenylpropyl group , 3— (1 naphthyl) propyl group, 3— (2 naphthyl) propyl group, 4 1-phenol butyl group, 4 1 (1 naphthyl) butyl group, 4— (2 naphthyl) butyl group, 5 phenol pentyl group , 5- (1-naphthyl) pentyl group, 5- (2 naphthyl) pentyl group, 6-phenylhexyl group or 6- (1-naphthyl) hexyl group, 6- (2naphthyl) hexyl group, a benzyl group 1 phenethyl group, 1-
  • C to C cycloalkyl group or “C to C cycloalkyloxy group” such as R 1 and the like
  • ⁇ C to C cycloalkyl moiety '' of, for example, cyclopropyl group, cyclobutyl group,
  • It may be an oral pentyl group or a cyclohexyl group, preferably a cyclopropyl group, a cyclobenzoyl group or a cyclohexyl group, and particularly preferably a cyclopentyl group or a cyclohexyl group.
  • Aryl group and the above-mentioned “heteroaryl group” group power which is a group which may be substituted with a selected substituent, for example, hydroxyiminomethyl group, N hydroxyethaneimido group, N hydroxypropane Imidoyl group, N hydroxybutaneimidoyl group, methoxyiminomethyl group, N-methoxyethaneimidoyl group, N ethoxyethaneimidoyl group, N butoxyalkaneimidoyl group, N allyloxettanimidoyl group, N-phenoxyethanimidoyl group, N-methoxypropaneimidoyl group, N-methoxybutanimidoyl group or N-methoxyhexanimidyl group, preferably hydroxyiminomethyl group, methoxyiminomethyl group, N-methoxyethaneimidoyl group, N-ethoxyethaneimidoyl group
  • the “halogen atom” such as R 1 is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably Is a fluorine atom or a chlorine atom, most preferably a fluorine atom.
  • an optionally substituted C to C alkyl group optionally substituted with 1 to 3 halogen atoms such as R 1, or “an optionally substituted C to C C
  • ⁇ c alkyl group and even more preferably, methyl group, ethyl group, propyl group,
  • the group force may also be selected from the same or different 1 to 3 substituents which may be substituted with a C to C alkyl group, or “optionally substituted C to C alkoxy.
  • c to c alkyl moiety such as “1 6 1 6 group” is, for example, the above “c to c alkyl group”.
  • It can be a 2-propyl group, 4 ethoxy 3 butur group, 3 phenoxy 2 butur group or 4 methoxy 3 chloro 2 butenyl group, preferably vinyl group, aryl group, 3 chloroallyl group Or a 3-methoxy-2-probe group, particularly preferably a bur group or an aryl group.
  • N 1 such as R 1 atom, C 1 -C alkoxy group and phenoxy group
  • the group force may also be substituted with the same or different 1 to 3 selected substituents, or a C 1 -C alkyl group ”or“ optionally substituted C 1 -C alkyl group ”.
  • 3-methoxy-2-propyl group 4-ethoxy-3-buturyl group, 3-phenoxy-2-buturyl group or 4-methoxy-4-chloro-2-buturyl group, preferably ethyl group, proper 2-in-1-yl Group, 3-chloro 2-propyl group or 4-bromo 2-butyl group, particularly preferably ethul group, proper 2-in-1-yl group or 3-chloro 2-propyl group.
  • R 1 or the like may be substituted with the same or different 1-2 C 1 -C alkyl groups.
  • amino group that may be substituted is preferably the same or different one of the above-mentioned “C 1 -C 4”.
  • Preferable is a dimethylamino group or a jetylamino group.
  • an “acyl moiety” such as “acyl group” or “acyloxy group” such as R 1 is a formyl group, a carbocycle group to which the “c to c alkyl group” is bonded ( c to c alkyl force
  • a carbonyl group (to which a “c to c alkylthio group” is bonded)
  • Carbon group preferably formyl group, c to alkylcarbonyl group (carbon).
  • a formyl group More preferably, a formyl group, a C-C alkylcarbonyl group, a benzoyl group, a C-
  • Acetyl, methylaminocarbol, dimethylaminocarboro, methoxycarbonyl, ethoxycarboro or benzoyl are preferred, and acetyl or methyl is most preferred. It is an aminocarbo group. C ⁇ group,
  • amino group optionally substituted with an acyl group is, for example, the above-mentioned “amino group optionally substituted with 1 to 2 identical C to C alkyl groups” or the same or different.
  • 1 to 2 of the “acyl groups” may be substituted amino groups, and preferably, the same or different 1 to 2 of the “acyl groups” may be substituted.
  • an amino group more preferably an acetylamino group, a benzoylamino group, a methoxycarboamino group, or a mono- or dimethylaminocarbonyl group, and particularly preferably an acetylamino group.
  • Substituted with the same or different 1 to 6 substituents may be an aryl group "or
  • the “aryl moiety” such as “substituted and optionally aryloxy” is, for example, a phenyl group, 2-, 3 or 4 methylphenol group, 2-, 3 or 4-methoxy group.
  • a group force consisting of a "norogen atom, a C-C alkyl group, a C-C alkoxy group, and a hydroxyl group force" such as R 1 is selected with the same or different 1 to 6 substituents selected.
  • Heteroaryl moiety such as “substituted, heteroaryl group” or “substituted, heteroaryloxy group” includes, for example, 2 pyridyl group, 3 pyridyl group, 4 pyridyl group Group, 5-methyl-2-pyridyl group, 3-isoxazolyl group, 5-isoxazolyl group, 5-methyl-3-isoxazolyl group, 4 pyrazolyl group, 5-pyrazolyl group, 2 furyl group, 3 furyl group, 3 thiazolyl group, 1 triazolyl group, 3 chael group, 3 isothiazolyl group, 2-oxazolyl group or 2-virazyl group, preferably 2 pyridyl group, 3 pyridyl group, 3 isoxazolyl group, 5 An isoxazolyl group, 5-methyl-3isoxazolyl group, 4 pyrazolyl group, 5 pyrazolyl group, 2 furyl group, 3 ful
  • an “aralkyl moiety” such as an aralkyl group ”substituted with the same or different 1 to 6 substituents, or an“ aralkyl moiety ”such as an“ aralkyloxy group ”may be an aralkyl group.
  • the substituent may be substituted on either or both of the aryl ring and the alkyl group constituting the aralkyl group.
  • Nyl group 1 phenethyl group, 2 phenethyl group, 3 phenylpropyl group, 2-, 3- or 4-methylbenzyl group, 2-, 3- or 4-methoxybenzyl group, 2-, 3- or 4 It can be a benzyl group, a 2-, 3-, or 4-fluorinated benzyl group, a 3 cyanobenzyl group, a 4 dimethylaminobenzyl group, or a 4 acetylaminobenzyl group, preferably a benzyl group, 2 phenethyl group, or 2 —, 3 or 4 Fluorobenzyl group.
  • One to four X can be substituted at any substitutable position on the A ring.
  • Y may be substituted at 1 to 6 substitutable positions on the pyridine ring condensed with the B ring.
  • Ring A is preferably an optionally substituted benzene ring, C-C cycloalkyl
  • a ring or a pyridine ring A ring or a pyridine ring
  • Ring A is more preferably an optionally substituted benzene ring or pyridine ring
  • Ring A is more preferably an optionally substituted benzene ring
  • Ring B is preferably an optionally substituted benzene ring, thiophene ring, oxazole ring, thiazole ring, pyridine ring, pyrazine ring, oxazine ring, dihydrooxazine ring.
  • Ring B is more preferably an optionally substituted benzene ring, pyridine ring or dihydroxazine ring.
  • ring B is more preferably a benzene ring or a pyridine ring which may be substituted
  • R ⁇ R 2 , R 3 and R 4 are preferably a hydrogen atom; a halogen atom; optionally substituted by 1 to 3 halogen atoms, which are the same or different, C to C Alkyl group; hydroxyl group; C to
  • a phenyl group or a naphthyl group which may be substituted with the same or different 1 to 3 substituents; a nitrogen atom, a C to C alkyl group, a C to C alkoxy group and a C to
  • C alkylthio group force can also be selected with the same or different 1 to 3 substituents
  • a phenylthio group optionally substituted by 3 substituents; a neurogenic atom, a C-C al
  • a benzyloxy group or a phenethyloxy group which may be substituted with the same or different 1 to 3 substituents; a nitrogen atom, a C 1 -C alkyl group, a C 1 -C alkoxy
  • Group and C-C alkylthio group forces are also selected the same or different 1-3 Benzylthio group or phenethylthio group; formyl group, c-c alkyl carbonyl group, c-c alkenyl carboxyl group, benzoyl
  • a C alkylaminocarbothio group or a force that is a cyano group, or
  • R 1 and R 2 ; or R 3 and R 4 forces together to represent an oxo group, or R 1 and R 2 ; or R 3 and R 4 forces together to represent a methylene group Or R 1 and R 3 or R 4 ; or R 2 and R 3 or R 4 forces together to represent a single bond,
  • R 2 , R 3 and R 4 are more preferably a hydrogen atom; a halogen atom; a C 1 -C alkyl group optionally substituted with 1 to 3 identical or different halogen atoms; a hydroxyl group C
  • substituents which may be the same or different, a phenyl group or a naphthyl group; a group consisting of a norogen atom, a C to C alkyl group and a C to C alkoxy group
  • substituents selected from: a phenoxy group; selected from the group consisting of a nonogen atom, a C to C alkyl group and a C to C alkoxy;
  • Xy group power chosen Benzyl group or phenethyl group, optionally substituted with the same or different 1 to 3 substituents selected; a nitrogen atom, a C to C alkyl group and C
  • ⁇ C Alkoxy group power is also selected group force is the same or different 1 to 3 substituents
  • ⁇ C Alkoxy group power is also selected group force is the same or different 1 to 3 substituents
  • 2 3 2 3 is a cyclohexylthio group or a c to c alkylamino carbonylthio group; or a cyano group.
  • Group force that can also be a group and C to C alkoxy group force same or different one to three selected
  • R 3 and R 4 forces together to represent an oxo group, or R 1 and R 2 ; or R 3 and R 4 forces together to represent a methylene group, or R 1 and R 3 or R 4 ; or R 2 and R 3 or R 4 forces together to represent a single bond,
  • R 2 , R 3 and R 4 are even more preferably substituted with 1 to 3 substituents of the same or different selected from a group consisting of a hydrogen atom; a halogen atom; a fluorine atom, a chlorine atom and a bromine atomic energy.
  • the group force may also be selected from the same or different substituents optionally substituted with 1 to 3 substituents.
  • Substituted with 1 to 3 substituents ! may! /, Benzyl group; benzyloxy group; benzylthio group; formyl group, C 1 -C alkyl carbo yl group, C 1 -C alkoxy carbo yl Group or c to c alkylaminocarbol group; acetyloxy group, c to c alkoxy force
  • R 1 and R 2 ; or R 3 and R 4 forces together to represent an oxo group, or R 1 and R 2 ; or R 3 and R 4 forces together, to form a methylene group.
  • R 2 , R 3 and R 4 are most preferably a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group or an ethyl group, or two of R 1 R 2 , R 3 and R 4 Together, they form a cyclobutyl ring, a cyclopentyl ring or a cyclohexyl ring,
  • Group power also may be substituted with the same or different 1 to 3 selected substituents, consisting of a C 1 to C alkyl group; a nitrogen atom, a C 1 to C alkoxy group and a phenoxy group
  • Group power may also be substituted with the same or different 1 to 3 substituents selected C ⁇
  • Phonyl group fluorine atom, chlorine atom and c to c alkoxy group force
  • Moyl group selected from the group consisting of a norogen atom, a c to c alkoxy group and a phenoxy group C to C alkaryl optionally substituted with 1 to 3 identical or different substituents
  • Xyl group group power that is also composed of a norogen atom, a C to C alkoxy group and a phenoxy group
  • C 1 -C 3 alkyloxy may be substituted with one or different 1 to 3 substituents
  • a benzyl group or a phenethyl group optionally substituted with 1 to 3 substituents; a nitrogen atom, optionally substituted with 1 to 3 different halogens C 1 to C
  • a C 1 -C alkyl group optionally substituted with 1 to 3 identical or different substituents;
  • a C 1 -C alkoxy group optionally substituted with 1 to 3 substituents;
  • C-C alkoxy group power also has the same or different 1 to 3 substituents selected
  • Benzyl group which may be substituted with the same or different 1 to 3 substituents which are also selected as a group force; Norogen atom, optionally substituted with 1 to 3 different halogens C to C Group power consisting of alkyl group and C to C alkoxy group
  • a group c to c alkyloxy group a group consisting of a fluorine atom, a chlorine atom, fluorine and chlorine;
  • C to C may be substituted with the same or different 1 to 3 substituents selected from
  • Benzyl group optionally substituted by 3 substituents; group power consisting of fluorine atom, chlorine atom, fluorine and chlorine, optionally substituted by 1 to 3 identical or different substituents The same selected from the group consisting of a good C to C alkyl group and a C to C alkoxy group
  • a bonyloxy group or a c to c alkylaminocarbonyloxy group A bonyloxy group or a c to c alkylaminocarbonyloxy group
  • R 5 is a hydrogen atom; a hydroxyl group; a fluorine atom and a chlorine atom group force.
  • a C 1 -C alkyl group which may be substituted with the same or different 1 to 3 selected substituents; a fluorine atom And a group power of chlorine nuclear power, which may be substituted with 1 to 3 identical or different substituents selected from C to C alkoxy groups; aryloxy groups; propargyloxy groups;
  • 2 5 2 5 2 5 is an aminocarbonyl group or a c to c alkyl group
  • R 5 is a hydrogen atom, a hydroxyl group, a methyl group, an ethyl group, a methoxy group, A group, an ethoxy group, an aryloxy group, a propargyloxy group, a benzyl group, a benzy
  • X is preferably an X force halogen atom; a C to C alkyl group which may be substituted with the same or different 1 to 3 substituents which are also selected as a group force consisting of a halogen nuclear atom;
  • a C to C alkyl group optionally substituted with 1 to 3 substituents; a fluorine atom, a salt
  • Force group power Force group that is optionally substituted with 1 to 3 substituents that may be substituted, such as a phenyl group or naphthyl group; fluorine atom, chlorine atom, bromine atom, fluorine, and chlorine force Group power consisting of C to C alkyl group and C to C alkoxy group which may be substituted with 1 to 3 identical or different substituents.
  • halogen atoms may be substituted with the same or different 1 to 3 substituents selected from C to C alkylthio groups; fluorine atom and chlorine atom group
  • X is preferably an X force halogen atom; C to C alkyl optionally substituted with 1 to 3 identical or different substituents
  • Substituted with 1 to 3 different substituents may be a phenol group; a fluorine atom, a chlorine atom, a methyl group, and a methoxy group force.
  • a hydrogen atom of a hydroxyl group may be substituted with a substituent selected from the group consisting of a-group, a phenyl group, a naphthyl group, a furyl group, a chael group, and a pyridyl group;
  • X is more preferably X is a halogen atom; a fluorine atom, a chlorine atom, and a bromine atomic force, or a group force that is the same or different and selected from 1 to 3 substituents.
  • X is even more preferably composed of X force halogen atom; fluorine atom and chlorine atom.
  • ⁇ C alkyl group selected from the group consisting of fluorine atom, chlorine atom, methyl group and methoxy group
  • N 0 to 2
  • X is particularly preferably an X force halogen atom or a C to C alkyl group, and n is n 14
  • X is most preferably X force is a fluorine atom, a chlorine atom or a methyl group, n is 0 to 2,
  • Y is preferably a repulsive halogen atom; a C to C alkyl group which may be substituted with the same or different 1 to 3 substituents selected from the group consisting of no and rogen atoms; Fluor
  • a C to C alkyl group optionally substituted with 1 to 3 substituents; a fluorine atom, a salt
  • Force group power Force group that is optionally substituted with 1 to 3 substituents that may be substituted, such as a phenyl group or naphthyl group; fluorine atom, chlorine atom, bromine atom, fluorine, and chlorine force Group power consisting of C to C alkyl group and C to C alkoxy group which may be substituted with 1 to 3 identical or different substituents.
  • substituents such as furyl, chenyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, pyridyl, birazyl, or Pyridazyl group; halogen nuclear power also selected C to C alkoxy optionally substituted with 1 to 3 identical or different substituents
  • halogen power may be selected by the same or different 1 to 3 substituents that may be selected.
  • C to C may be substituted with the same or different 1 to 3 substituents that are also selected
  • Y is preferably a Y-force halogen atom; a C-C alkyl which may be substituted with the same or different 1 to 3 substituents which are also selected as a group force consisting of a halogen nuclear power.
  • Substituted with 1 to 3 different substituents may be a phenol group; a fluorine atom, a chlorine atom, a methyl group, and a methoxy group force.
  • ⁇ may be substituted with 1 to 3 substituents, which are the same or different, selected from a halogen atom, a fluorine atom, a chlorine atom, and a bromine atomic force.
  • substituents which are the same or different, selected from a halogen atom, a fluorine atom, a chlorine atom, and a bromine atomic force.
  • a group selected from the group consisting of a c-c alkyl group and a c-c alkoxy group May be substituted with 1 to 3 different substituents, including a phenyl group; a furyl group, a chael group or a pyridyl group; a C to C alkoxy group; and 1 to 2 C to C alkyl groups.
  • an amino group or an acetylamino group a c to c alkyl carbo group,
  • a group, m is 0-2,
  • Y is even more preferably substituted with 1 to 3 substituents selected from the same or different Y force halogen atom; a group force consisting of a fluorine atom and a chlorine atom.
  • Y is particularly preferably a Y force halogen atom or a C to C alkyl group, and m is m 14.
  • Y is most preferably a repulsive fluorine atom, a chlorine atom or a methyl group, and an m force of 0 to 2.
  • the compound (I) of the present invention can be converted to a salt such as sulfate, hydrochloride, nitrate or phosphate.
  • a salt such as sulfate, hydrochloride, nitrate or phosphate.
  • These salts are included in the present invention as long as they can be used as agrochemical compositions (agricultural and horticultural fungicides).
  • the compound (I) of the present invention can be solvated, and these solvates are also encompassed in the present invention.
  • Such solvates are preferably hydrates.
  • the compound (I) of the present invention includes a compound having an asymmetric carbon.
  • the present invention contains one kind of optically active substance and several kinds of optically active substances in an arbitrary ratio. Also included is a mixture.
  • Me represents a methyl group
  • Et represents an ethyl group
  • Pr represents a propyl group
  • Vinyl represents a bur group
  • Allyl represents an aryl group
  • Ethynyl represents an ethul group.
  • Ph '' is a phenyl group
  • ⁇ Ac '' is a acetyl group
  • ⁇ MeMeIMD '' is an N-methoxymethanimidyl group
  • ⁇ Pyr '' is a pyridyl group
  • ⁇ Bn '' is a benzyl group
  • ⁇ CPr '' is cyclopropyl group
  • ⁇ cBu '' is cyclo A butyl group
  • “cPen” represents a cyclopentyl group
  • cHex represents a cyclohexyl group
  • Xn represents “5-PYR”, “6-PYR”.
  • rings ⁇ are 5-pyridyl ring, 6-pyridyl ring, 5-chael ring and 6-chael ring, respectively.
  • All of the substituents (Xn) are hydrogen atoms, and Xn force indicates a group other than the above
  • ring A is a benzene ring
  • the substituent is Xn itself
  • Ym is ⁇ 6 — PYR ”,“ 7—PYR ”,“ 8—PYR ”,“ 5, 8—PRA ”,“ 5, 7—OXZO ”,“ 5, 7—THA ”,“ 3H—5, 8—OXZN ”,
  • ring B is 6-pyridyl ring, 7-pyridyl ring, 8-pyridyl ring, 5 (nitrogen), 8 (nitrogen) -pyrazine ring, 5 (Oxygen), 7
  • HH, HH 5-Me H-40 H HH, HH 6 Me H-41 H, HH, HH 7- Me H-42 H, HH, HH 5-cHex H-43 H, HH, HH 5-Allyl H-44 H, HH, HH 5-Etynyl H-45 H , HH, HH 5-Ph H-46 H, HH, HH 5-Pyr H-47 H, HH, HH 6-MeO H-48 H, HH, HH 6J- (MeO) 2 H-49 H, HH, HH 5-MeS H-50 H, HH, HH 5-MeSO H-51 H, HH, HH 5-MeS02 H-52 H, HH, HH 5-MeNH H-53 H, HH, HH 5-Ac H- 54 H, HH, HH 5-CN H-55 H, HH, HH 5-MeMeIMD H-56 H, HH, Me HH H-57 H, HH,
  • suitable compounds are compound numbers 1 10, 1 35, 1 56, 1 — 77, 1 — 78, 1 — 100, 1 — 123, 1 — 129, 1 — 130, 1 — 131, 1—132, 1—133
  • Particularly preferred compounds are compound numbers
  • the compound (la) of the present invention can be produced by a known method described in Non-Patent Document 1 or the like, or by methods A to F described below.
  • ring A, ring B, R 2 , R °, R 4 , X, n, Y, and m have the same meaning as described above (where R 1 is bonded, R 3 is bonded to R 3 , and Is a single bond.)
  • Method A is a method for producing the compound (la) of the present invention by reacting a nitrile compound (II) and an alcohol compound (III) according to a litter reaction.
  • step A the nitrile compound (II) is reacted with the alcohol compound (III) in the presence of an acid in a solvent or in the absence of a solvent (preferably in the absence of a solvent).
  • the alcoholic compound (III) to be used is usually 1 to 6 mol, preferably 1.1 to 3.0 mol, per 1 mol of the nitrile compound (11).
  • the solvent used is not particularly limited as long as it does not inhibit the reaction.
  • hydrocarbons such as hexane, cyclohexane, and octane. Elements; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as dichloromethane, dichloromethane, chloroform and carbon tetrachloride; or dioxane, jetyl ether, tetrahydrofuran (THF) and ethers such as dibutyl ether, preferably hydrocarbons, aromatic hydrocarbons or halogenated hydrocarbons, and more preferably benzene or dichloroethane.
  • hydrocarbons such as hexane, cyclohexane, and octane. Elements; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as dichloromethane, dichloromethane, chlor
  • the acid used in this step is not particularly limited as long as it is used as an acid in a normal litter reaction.
  • inorganic acids such as sulfuric acid, phosphoric acid and perchloric acid; formic acid and trifluoroacetic acid
  • Carboxylic acids such as benzene sulfonic acid, toluene sulfonic acid and trifluoromethane sulfonic acid
  • Lewis acids such as tin tetrachloride and trifluoroboron, preferably inorganic acids, carboxylic acids Acids or sulfonic acids are preferable, and sulfuric acid or trifluoromethanesulfonic acid is more preferable.
  • the amount of the acid used is usually 1 to 20 moles per mole of the nitrile compound (11), and preferably 1 to 15 monolayers.
  • reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally ⁇ 20 ° C. to 100 ° C., preferably 0 ° C. to 80 ° C.
  • reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 15 minutes to 120 hours, preferably 30 minutes to 72 hours.
  • A-Torrui compound (II) is a known compound or a known method ⁇ for example, Non-Patent Document 5: Journal, Med, Medicinal, Chemistry (j. Med. m.), 22 ⁇ , page 816 (1979) ⁇ .
  • the alcohol compound (III) used in this step is a known compound, or a known method ⁇ for example, Non-Patent Document 6: Tetrahedron, 55 ⁇ , page 4595 (1999). Can be produced according to the method
  • the compound (lb) of the present invention can be produced by Method B described below.
  • ring A, ring B, R ⁇ R 3 , X, n, Y and m are as defined above (provided that, in the compound (la ′), R 1 is bonded).
  • the carbon atom to which R 3 is bonded is a single bond, and in the compound (lb), the carbon atom to which R 1 is bonded to the carbon atom to which R 3 is bonded in the compound (lb).
  • the bond is a double bond.
  • the compound (lb) of the present invention is produced by acidifying (dehydrogenating) the compound (la ′) in which R 2 and R 4 are hydrogen atoms in the compound (la) of the present invention. Is the method.
  • Step B is a step for producing the compound (lb) of the present invention by oxidizing (dehydrogenating) the compound (la ′) in a solvent in the presence of a catalyst.
  • the catalyst used in this step is not particularly limited as long as it is used for a normal oxidation (dehydrogenation) reaction.
  • it can be palladium carbon, acid platinum or Raney nickel, and preferably palladium. —Carbon.
  • the amount of the catalyst used is usually from 0.005 to 10 mol, and preferably from 0.05 to L0 mol, relative to 1 mol of the compound (la ′).
  • the solvent used in this step does not inhibit the reaction, and is not particularly limited as long as it is a solvent.
  • hydrocarbons such as hexane, cyclohexane, benzene, toluene and xylene; dichloromethane, Halogenated hydrocarbons such as chloroform and tetrasalt carbon; or ethers such as dioxane, jetyl ether, tetrahydrofuran (THF) and dibutyl ether, preferably hydrocarbons More preferably, it is toluene or xylene.
  • reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally 0 ° C to 200 ° C, preferably 20 ° C to 180 ° C.
  • reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 1 hour to 120 hours, preferably 3 hours to 72 hours.
  • Compound (Ic) of the present invention can be produced by Method C and Method D described below.
  • ring A, ring B, R 4 , X, n, Y, and m are as defined above (where R 1 is bonded, R 3 is bonded to R 3 , and the bond to the carbon atom is a single bond). is there.).
  • Method C is a method for producing compound (1) in which R 5 is a hydrogen atom in compound (Ic) of the present invention by reducing compound (la) of the present invention.
  • Step C is a step for producing compound (Ic ′) of the present invention by subjecting compound (la) to a reduction reaction in a solvent.
  • the reduction reaction used in this step is not particularly limited as long as it is used to reduce imine.
  • a catalytic reduction catalyst such as palladium carbon, platinum oxide and Raney nickel and hydrogen are used.
  • Catalytic hydrogenation reaction reaction using a combination of metal-acid such as zinc-acetic acid and tin-hydrochloric acid as the reducing agent; such as lithium aluminum hydride, sodium borohydride and sodium cyanoborohydride as the reducing agent
  • the reaction may be a reaction using a metal hydride, preferably a reaction using a metal hydride as a reducing agent, and more preferably a reaction using sodium borohydride as a reducing agent.
  • the amount of the metal-acid combination or metal hydride used is compound (la) 1 monolayer, but usually 0.5 to 20 monoles, which is preferred. ⁇ , 0.5 to 10 mono.
  • the hydrogen pressure used for the catalytic hydrogenation reaction is usually 1 to 10 atm, and preferably 1 to 2 atm.
  • the solvent used in this step does not inhibit the reaction, and is not particularly limited as long as it is a solvent.
  • hydrocarbons such as hexane, cyclohexane, benzene, toluene and xylene; dichloromethane, Halogenated hydrocarbons such as black mouth form and tetrasalt carbon; alcohols such as methanol, ethanol and 2-propanol; acids such as acetic acid, hydrochloric acid and sulfuric acid; or dioxane, jetyl ether, Ethers such as tetrahydrofuran (THF) and dibutyl ether can be used, preferably alcohols, and more preferably ethanol.
  • THF tetrahydrofuran
  • reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally 0 ° C to 200 ° C, preferably 20 ° C to 180 ° C.
  • reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 1 hour to 120 hours, preferably 2 hours to 72 hours.
  • ring A, ring B, X, n, Y and m represents the same meanings as defined above, R ° a is in R 5, which may be substituted C ⁇ C alkyl group, an optionally substituted C
  • Method D consists of alkylating, sulf-Louis ⁇ , sulfo-Louis ⁇ , sulfamoylation, aralkylation, acylation, silylation or phosphorylation of the compound (Ic,) of the present invention. This is a process for producing the compound (Ic ") of the invention.
  • step D compound (1) is converted to a compound in the presence of a base in a solvent.
  • R 5 a ′ has the same meaning as R 5 a except for the formyl group, and Z represents a halogen atom, particularly a chlorine, bromine or iodine atom.
  • R 5 is R 5 a to produce a compound (Ic ′′) of the present invention by reacting with a compound (IV) having the formula (IV) or a mixed acid anhydride of formic acid and acetic acid.
  • the amount of compound anhydride (IV) and the mixed acid anhydride of formic acid and acetic acid used is usually 1 to 130 monolayers for compound (Ic ') 1 monolayer, and preferably 1.1 to 1 10 monoles.
  • the base used in this step is not particularly limited as long as it is used as a base (deoxidizing agent) in a normal reaction.
  • alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium bicarbonate And alkali metal hydrogen carbonates such as potassium hydrogen carbonate; alkali metal hydrides such as sodium hydride, lithium hydride and potassium hydride; sodium hydroxide, potassium hydroxide and barium hydroxide Alkali metal hydroxides or alkaline earth metal hydroxides; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide; triethylamine, tributylamine, diisopropylethyla Min, N-methylmorpholine, pyridine, 4-((N, N-dimethylamino) pyri , N, N-dimethylaniline, N, N-jetylaniline, 1,5-diazabicyclo [4.3.0] noner-5-ene, 1,4
  • the amount of the base to be used is generally 1-30 mol, preferably 1.1-10 mol, per 1 mol of compound (IV).
  • the solvent used in this step does not inhibit the reaction, and is not particularly limited as long as it is a solvent.
  • hydrocarbons such as hexane, cyclohexane, benzene and toluene; Halogenated hydrocarbons such as chloromethane, dichloroethane, chloroform and tetrachloroethane; ethers such as dioxane, jetyl ether, tetrahydrofuran (THF) and ethylene glycol dimethyl ether; dimethylformamide, dimethylacetamide and Amides such as hexamethylphosphoric triamide (HMPA); ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; -tolyls such as acetonitrile and isobutyric-tolyl; or methyl acetate, Esters such as ethyl acetate and propyl acetate can be used,
  • reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally ⁇ 20 ° C. to 150 ° C., preferably 0 ° C. to 40 ° C.
  • reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 5 minutes to 120 hours, preferably 15 minutes to 48 hours.
  • Method E is a method for producing the compound (Id) of the present invention in which R 5 is a hydroxyl group by oxidizing and reducing the compound (la).
  • step E-1 the oxazolidine compound (V) is produced by reacting the compound (la) produced according to the above method A with an oxidizing agent in a solvent or non-solvent (preferably in a solvent). It is a process to do.
  • the solvent used is not particularly limited as long as it does not inhibit the reaction.
  • organic acids such as formic acid and acetic acid; hexane, cyclohexane, benzene, toluene and Hydrocarbons such as xylene; halogenated hydrocarbons such as dichloromethane, dichloromethane, chloroform and carbon tetrachloride; alcohols such as methanol, ethanol and 2-propanol; or dioxane, jetyl ether, Ethers such as tetrahydrofuran (THF) and dibutyl ether can be used, preferably alcohols or hydrocarbons, more preferably alcohols, and particularly preferably methanol.
  • THF tetrahydrofuran
  • the oxidizing agent used in this step is not particularly limited as long as it is used in a reaction in which ordinary imine is oxidized to oxazolidine.
  • methacroperbenzoic acid, paranitroperbenzoic acid and Perbenzoic acids such as monoperoxyphthalic acid; peracids such as trifluoroperacetic acid, peracetic acid and formic acid; peroxides such as dimethyldioxolane; Hydroperoxides such as hydroxide, tamyl hydroperoxide and hydrogen peroxide, preferably perbenzoic acids, peracids or hydroperoxides under metal catalysis. More preferred are perbenzoic acids or peracids, and particularly preferred are metabenzoic perbenzoic acid or peracetic acid.
  • the amount of the oxidizing agent used is usually 1 to 20 moles per mole of the compound (la), and preferably 1 to 15 monolayers.
  • the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, but is usually 0 ° C to 200 ° C, preferably 10 ° C to 100 ° C.
  • reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 15 minutes to 120 hours, preferably 30 minutes to 72 hours.
  • Process E-2 is a process for producing N-xoxide compound (VI) by treating oxazolidine compound (V) with an acid in a solvent or non-solvent (preferably in a solvent). .
  • a solvent is used in this step, the solvent used is not particularly limited as long as it does not inhibit the reaction.
  • hydrocarbons such as hexane, cyclohexane, benzene, toluene and xylene; dichloromethane , Halogenated hydrocarbons such as dichloroethane, chloroform and carbon tetrachloride; or ethers such as dioxane, jetyl ether, tetrahydrofuran (THF) and dibutyl ether, preferably halogen.
  • Hydrocarbons and more preferably black mouth form.
  • the acid used in this step is not particularly limited.
  • inorganic acids such as sulfuric acid, formic acid, phosphoric acid and perchloric acid
  • sulfonic acids such as benzenesulfonic acid, toluenesulfonic acid and trifluoromethansulfonic acid
  • Lewis acids such as tin tetrachloride and trifluoroboron
  • inorganic acids or sulfonic acids preferably sulfuric acid or methanol sulfonic acid.
  • the amount of the acid used is usually 1 to 20 mol, preferably 1.1 to 15 mol, per 1 mol of the oxazolidin compound (V).
  • reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally ⁇ 20 ° C. to 100 ° C., preferably 0 ° C. to 80 ° C.
  • reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 15 minutes to 120 hours, preferably 30 minutes to 72 hours.
  • Step E-3 is a step for producing the compound (Id) of the present invention by subjecting the N-oxide compound (VI) to a reduction reaction in a solvent, except for the following conditions. It is performed in the same way as the process.
  • the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, but is usually 0 ° C to 200 ° C, preferably 10 ° C to 100 ° C.
  • reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 10 minutes to 72 hours, preferably 15 minutes to 24 hours.
  • R 5 b is an optionally substituted C to C alkoxy group in R 5 , C optionally substituted
  • it represents an aralkyloxy group or an acyloxy group (provided that R 1 is bonded and TV, a carbon atom and R 3 are bonded, and the bond between the carbon atom is a single bond).
  • Method F is a method for producing a compound (Ie) of the present invention in which R 5 is R 5 b by alkylating, alkenylating, alkynylating, aralkylating or acylating the compound (Id) of the present invention. It is.
  • Step F comprises compound (Id) in the presence of a base in a solvent with the formula
  • R 5 b ′ is a group excluding the formyl group, and a group excluding the oxygen atom (ie, excluding the formyloxy group, R 5 b is —O—R 5 b)).
  • Z represents a halogen atom (in particular, a chlorine, bromine or iodine atom).
  • the base used in this step is preferably an alkali metal carbonate or alkali metal hydride, more preferably an alkali metal hydride, and most preferably sodium hydride.
  • the solvent used in this step is preferably an amide or a ketone, more preferably an amide, and most preferably dimethylformamide.
  • reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally ⁇ 20 ° C. to 150 ° C., preferably 0 ° C. to 40 ° C.
  • reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 10 minutes to 120 hours, preferably 30 minutes to 72 hours.
  • the target compound of each reaction can be collected from the reaction mixture according to a conventional method.
  • the reaction mixture is appropriately neutralized, and if insoluble matter is present, it is appropriately removed by filtration, and then an organic solvent immiscible with water, such as ethyl acetate, is added, washed with water, and then containing the target compound.
  • the organic layer is separated and dried over anhydrous magnesium sulfate, and then the solvent is distilled off to obtain the target compound for each reaction.
  • the obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation or chromatography.
  • the step of producing the salt of the compound (I) of the present invention comprises the compound (la), (lb),
  • the acid used in the reaction is a hydrohalic acid (eg hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid), inorganic such as nitric acid, perchloric acid, sulfuric acid and phosphoric acid.
  • hydrohalic acid eg hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid
  • inorganic such as nitric acid, perchloric acid, sulfuric acid and phosphoric acid.
  • alkyl sulfonic acids eg methane sulfonic acid, trifluoromethane sulfonic acid and ethane sulfonic acid
  • aryl sulfonic acids eg benzene sulfonic acid and ⁇ -toluene sulfonic acid
  • carboxylic acids eg succinic acid and sulfur Acid
  • organic acid amide compounds such as saccharin, preferably nitric acid, sulfuric acid or methanesulfonic acid.
  • the amount of the acid used is usually 1 equivalent to 10 equivalents, and preferably 1 equivalent to 5 equivalents.
  • the solvent used in the reaction is not particularly limited as long as the reaction is not inhibited.
  • ethers such as ether, diisopropyl ether, tetrahydrofuran (THF) and dioxane; or methanol and ethanol And preferably are ether or methanol.
  • the reaction temperature is usually -20 ° C to 50 ° C, preferably -10 ° C to 30 ° C.
  • the reaction time varies depending on the type of solvent used and the temperature. ⁇ 1 hour.
  • the resulting salt is isolated by conventional methods. That is, it is isolated by filtration when it is precipitated as crystals, and is isolated as an aqueous solution by separating an organic solvent and water when it is water-soluble.
  • the compound (I) of the present invention is useful as an active ingredient of an agrochemical composition (particularly a pest control agent).
  • an agricultural and horticultural fungicide it exhibits an excellent control effect against diseases caused by various plant pathogens.
  • the auxiliary agent used can be a carrier, an emulsifier, a suspending agent, a dispersing agent, a spreading agent, a penetrating agent, a wetting agent, a thickening agent, a stabilizer, and the like, and can be appropriately added as necessary. .
  • the carrier used is divided into a solid carrier and a liquid carrier, and the solid carrier is starch, sugar, cellulose powder, cyclodextrin, activated carbon, soy flour, wheat flour, chaff flour, wood flour, fish flour and milk powder.
  • Animal or vegetable powders such as; or minerals such as talc, kaolin, bentonite, organic bentonite, calcium carbonate, calcium sulfate, sodium bicarbonate, zeolite, diatomaceous earth, white force, bonbon, clay, alumina, silica and sulfur powder
  • Liquid carrier can be powder; water; animal and vegetable oils such as soybean oil, nut oil and corn oil; alcohols such as ethyl alcohol and ethylene glycol; ketones such as acetone and methyl ethyl ketone Ethers such as dioxane and tetrahydrofuran; kerosene, kerosene, liquid paraffin, xylene, toluene Aliphatic Z aromatic hydrocarbons such as methylbenzene, tetramethylbenzene, cyclohexane and solvent naphtha; Halogenated hydrocarbons such as black mouth form and black mouth benzene; Acid amides such as dimethyl formamide Class:
  • the compounding mass ratio of the compound of the present invention to the adjuvant is usually 0.05: 99.95 to 90:10, and preferably 0.2: 99.8 to 80:20.
  • the concentration or amount used of the compound of the present invention varies depending on the target crop, method of use, formulation, application rate, etc., but in the case of foliage treatment, it is usually 0.1 to 10,000 ppm per active ingredient. In the case of soil treatment, it is usually 10-: LOOOOOgZha, preferably 100-10000 gZha.
  • the compound of the present invention may contain other pesticides such as insecticides, acaricides, attractants, nematicides, fungicides, antiviral agents, herbicides, and Z or plant growth as necessary. It can be mixed or used in combination with agents, and those used or combined are preferably insecticides, acaricides, nematicides or fungicides.
  • pesticides such as insecticides, acaricides, attractants, nematicides, fungicides, antiviral agents, herbicides, and Z or plant growth as necessary. It can be mixed or used in combination with agents, and those used or combined are preferably insecticides, acaricides, nematicides or fungicides.
  • the insecticides used are, for example, O, O Jetyl—O— (5 phenol—3-isoxazolyl) phosphorothioate (generic name: isoxathione), O, O dimethyl—O— (3— Methyl-4-tropho) thiophosphate (generic name: phetrothion), O, O Jethyl O- (2 isopropyl-4-methylpyrimidine-6 yl) thiophosphate (generic name: diazinon), O , S Organophosphate compounds such as dimethyl N-acetyl phosphoramidothioate (generic name: acephate) and O, O dimethyl S—1,2-diethoxycarbo-ruethyl dithiophosphate (generic name: malathion);
  • the fungicides used are, for example, Manganese ethylene bis (dithiocarbamate) (generic name: mannebu), zinc and manganese ethylenebis (dithiocarbamate) (generic name: manzeb) and 3, 3 ethylene.
  • Dithiocarnomate compounds such as bis (tetrahydro-4,6 dimethyl-2H-1,3,5-thiadiazine 2-thione (generic name: mirneb) (trichloromethylthio) cyclohexene 4-ene 1,2 dicarboximide (general N-halogenoalkyl, such as N- (l, 1, 2, 2-tetrachloroethylthio) cyclohexyl-4-ene-1,2-dicarboximide (generic name: captaphor) Thioimide compounds;
  • Halogenoaromatic compounds such as 4, 5, 6, 7-tetrachlorophthalic phthalide (generic name: fusalide) and tetrachlorophthalic isophthalic-tolyl (generic name: chlorothalic);
  • Methyl 1 (butylcarbamoyl) 2-benzimidazole carbamate (generic name: Benzimidazole compounds such as Benomyl);
  • Copper-based compounds such as cupric hydroxide (generic name: cupric hydroxide) and kappa 8-quinolinolate (generic name: quinoline copper);
  • Isoxazole compounds such as 3-hydroxy 5-methylisoxazole (generic name: hymexazole);
  • Benth anilide compounds such as a, a, ⁇ -trifluoro-3, monoisopropoxy o toluanilide (generic name: flutol) and 3'-isopropoxy-o tolurilide (generic name: meprol);
  • 1, 1-iminotazine-based compounds such as iminodi (otatamethylene) digadi-umtriacetate (generic name: iminotadine);

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne un dérivé de 3-(isoquinoline-1-yl)quinoline (I), un sel dudit dérivé et une composition agrochimique les contenant en tant qu’ingrédients actifs, en particulier un bactéricide agricole et horticole présentant un excellent effet sur une variété d’agents pathogènes de plantes (en particulier pour la pyriculariose du riz) sans entraîner de dommage pour une plante hôte. L’invention concerne plus spécifiquement un dérivé de 3-(isoquinoline-1-yl)quinoline (I) représenté par la formule (I) (où l’anneau A et l’anneau B sont un anneau de benzène ou analogue ; R1 à R4 sont H, un halogène, un alkyle, OH, un groupe alkoxy ou analogue ; Q est N, N-R5 (où R5 est H, OH, un groupe alkyle ou analogue) ; X est un halogène, un alkyle ou analogue ; Y est un halogène, un groupe alkyle ou analogue ; n est compris entre 0 et 4 ; m est compris entre 0 et 6 ; et une liaison incluant une ligne en pointillé est une liaison simple ou une liaison double) ou un sel de celui-ci.
PCT/JP2006/314478 2005-07-22 2006-07-21 Dérivé de 3-(isoquinoline-1-yl)quinoline Ceased WO2007011022A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2005212324 2005-07-22
JP2005-212324 2005-07-22

Publications (1)

Publication Number Publication Date
WO2007011022A1 true WO2007011022A1 (fr) 2007-01-25

Family

ID=37668893

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2006/314478 Ceased WO2007011022A1 (fr) 2005-07-22 2006-07-21 Dérivé de 3-(isoquinoline-1-yl)quinoline

Country Status (2)

Country Link
TW (1) TW200740788A (fr)
WO (1) WO2007011022A1 (fr)

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009081579A1 (fr) 2007-12-26 2009-07-02 Nippon Soda Co., Ltd. Composé hétérocyclique contenant de l'azote et bactéricide pour utilisation en agriculture et horticulture
WO2009144935A1 (fr) 2008-05-28 2009-12-03 日本曹達株式会社 Composés hétérocycliques azotés et fongicides destinés à un usage agricole et horticole
JP2010006746A (ja) * 2008-06-27 2010-01-14 Mitsui Chemicals Agro Inc 植物病害防除組成物及びそれを施用する植物病害の防除方法
WO2010018686A1 (fr) 2008-08-12 2010-02-18 日本曹達株式会社 Dérivé hétérocyclique azoté, et agent bactéricide agricole ou horticole
WO2010125782A1 (fr) * 2009-04-28 2010-11-04 日本曹達株式会社 Composé hétérocyclique contenant de l'azote et bactéricide agricole ou horticole
EP2103214A4 (fr) * 2006-12-01 2011-01-12 Mitsui Chemicals Agro Inc Agent de traitement de sols ou de graines comprenant un composé quinoléine ou un sel de celui-ci en tant que substance active, ou procédé pour lutter contre une maladie de plante l'utilisant
JP2011012017A (ja) * 2009-07-01 2011-01-20 Mitsui Chemicals Agro Inc キノリン系化合物を含有する植物病虫害防除剤および防除方法
WO2011037128A1 (fr) * 2009-09-28 2011-03-31 日本曹達株式会社 Composé hétérocyclique contenant de l'azote et sel de celui-ci et bactéricide à usage agricole et horticole
WO2011077514A1 (fr) 2009-12-22 2011-06-30 三井化学アグロ株式会社 Composition permettant de lutter contre des maladies végétales et procédé de lutte contre des maladies végétales par application de la composition
JPWO2009119089A1 (ja) * 2008-03-27 2011-07-21 日本電気株式会社 含窒素複素環化合物及び農園芸用殺菌剤
JP2011162472A (ja) * 2010-02-09 2011-08-25 Nippon Soda Co Ltd 含窒素ヘテロ環化合物またはその塩、ならびに農園芸用殺菌剤
WO2012161071A1 (fr) 2011-05-20 2012-11-29 日本曹達株式会社 Composé hétérocyclique azoté et agent bactéricide agricole ou horticole
WO2013047751A1 (fr) * 2011-09-29 2013-04-04 三井化学アグロ株式会社 Procédé de fabrication de dérivé de 3,4-dihydroisoquinoléine
WO2013047750A1 (fr) * 2011-09-29 2013-04-04 三井化学アグロ株式会社 Procédé de fabrication de dérivé de 3,4-dihydroisoquinoléine, et corps intermédiaire de cette fabrication
WO2013047749A1 (fr) * 2011-09-29 2013-04-04 三井化学アグロ株式会社 Procédé de fabrication de dérivé de 4,4-difluoro-3,4-dihydroisoquinoléine
JPWO2011081174A1 (ja) * 2010-01-04 2013-05-13 日本曹達株式会社 含窒素ヘテロ環化合物ならびに農園芸用殺菌剤
WO2015132133A1 (fr) * 2014-03-04 2015-09-11 Syngenta Participations Ag Dérivés hétérobicycliques microbiocides
WO2015141867A1 (fr) 2014-03-20 2015-09-24 Mitsui Chemicals Agro, Inc. Composition de lutte contre une maladie de plante, et procédé de lutte contre une maladie de plante par application de cette dernière
CN105325435A (zh) * 2009-12-22 2016-02-17 三井化学Agro株式会社 植物病害防除组合物及施用其的植物病害的防除方法
WO2017090664A1 (fr) * 2015-11-25 2017-06-01 三井化学アグロ株式会社 Composé quinoxalylisoquinoline
CN106834135A (zh) * 2016-12-26 2017-06-13 西北农林科技大学 一种诱导葡萄痂囊腔菌产孢的方法
US9795135B2 (en) 2013-07-24 2017-10-24 Bayer Cropscience Aktiengesellschaft Binary fungicidal composition
WO2018065182A1 (fr) * 2016-10-04 2018-04-12 Basf Se Composés de quinoléine réduits en tant qu'agents antifuni
WO2018116072A1 (fr) 2016-12-20 2018-06-28 Pi Industries Ltd. Composés hétérocycliques
WO2018134127A1 (fr) * 2017-01-23 2018-07-26 Basf Se Composés de pyridine fongicides
JP2018525392A (ja) * 2015-08-12 2018-09-06 シンジェンタ パーティシペーションズ アーゲー 殺微生物二環式複素環式誘導体
WO2018184882A1 (fr) * 2017-04-06 2018-10-11 Basf Se Composés de pyridine
WO2018190326A1 (fr) * 2017-04-10 2018-10-18 三井化学アグロ株式会社 Composition de lutte contre les nuisibles contenant un composé pyridone et un composé à base de quinoléine et procédé de lutte contre les nuisibles, et nouveau composé à base de quinoléine
JP2019151631A (ja) * 2018-03-02 2019-09-12 国立大学法人 岡山大学 植物病害防除剤及び植物病害の防除方法
US11064697B2 (en) 2015-07-24 2021-07-20 Basf Se Pyridine compounds useful for combating phytopathogenic fungi
WO2022223376A1 (fr) 2021-04-20 2022-10-27 Syngenta Crop Protection Ag Dérivés de quinoléine/quinoxaline isoquinoline microbiocides
WO2024068656A1 (fr) 2022-09-28 2024-04-04 Syngenta Crop Protection Ag Compositions fongicides

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005070917A1 (fr) * 2004-01-23 2005-08-04 Sankyo Agro Company, Limited 3-(dihydro(tetrahydro)isoquinolin-1-yl)quinolines

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005070917A1 (fr) * 2004-01-23 2005-08-04 Sankyo Agro Company, Limited 3-(dihydro(tetrahydro)isoquinolin-1-yl)quinolines

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHAKRAVORTI S.S.: "Isoquinolylquinoline Derivatives: Part I -Synthesis of Some 3-(3',4'-Dihydroisoquinolyl-I')-4-substituted Quinoline Derivatives as Possible Spasmolytic Agents", INDIAN JOURNAL OF CHEMISTRY, vol. 7, no. 10, 1969, pages 1010 - 1016, XP003007738 *
CHAKRAVORTI S.S.: "Isoquinolylquinoline Derivatives: Part III- Synthesis of Some 4-Substituted 3-(3',4'-Dihydro-1'-isoquinolyl)quinoline Derivatives as Possible Antifilarial Agents", INDIAN JOURNAL OF CHEMISTRY, vol. 24B, no. 7, 1985, pages 737 - 746, XP002989511 *
CHAKRAVORTI S.S.: "Synthesis of Some Isoquinolylpyrazolo[3,4-b]-pyridine Derivatives as Possible Antifilarial Agents", INDIAN JOURNAL OF CHEMISTRY, vol. 16B, no. 2, 1978, pages 161 - 163, XP003007739 *
DAS M.: "Isoquinolylquinoline Derivatives: Part IV -Synthesis of Some 4-Substituted 3-(3',4'-Dihydro-3'-methyl-1'-isoquinolyl)-7-chloro-quinoline Derivatives as Possible Trypanocidal Agents", INDIAN JOURNAL OF CHEMISTRY, vol. 25B, no. 10, 1986, pages 1072 - 1078, XP002989512 *

Cited By (63)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2007326412B2 (en) * 2006-12-01 2013-05-02 Mitsui Chemicals Crop & Life Solutions, Inc. Soil- or seed-treating agent comprising quinoline compound or salt thereof as active ingredient, or method for control of plant disease using the same
EP2103214A4 (fr) * 2006-12-01 2011-01-12 Mitsui Chemicals Agro Inc Agent de traitement de sols ou de graines comprenant un composé quinoléine ou un sel de celui-ci en tant que substance active, ou procédé pour lutter contre une maladie de plante l'utilisant
US8729093B2 (en) 2006-12-01 2014-05-20 Mitsui Chemicals Agro, Inc. Soil treating agent or seed treating agent comprising quinoline compounds or salts thereof as active ingredient, or method for preventing plant diseases by using the same
WO2009081579A1 (fr) 2007-12-26 2009-07-02 Nippon Soda Co., Ltd. Composé hétérocyclique contenant de l'azote et bactéricide pour utilisation en agriculture et horticulture
JPWO2009119089A1 (ja) * 2008-03-27 2011-07-21 日本電気株式会社 含窒素複素環化合物及び農園芸用殺菌剤
WO2009144935A1 (fr) 2008-05-28 2009-12-03 日本曹達株式会社 Composés hétérocycliques azotés et fongicides destinés à un usage agricole et horticole
JPWO2009144935A1 (ja) * 2008-05-28 2011-10-06 日本曹達株式会社 含窒素ヘテロ環誘導体および農園芸用殺菌剤
JP2010006746A (ja) * 2008-06-27 2010-01-14 Mitsui Chemicals Agro Inc 植物病害防除組成物及びそれを施用する植物病害の防除方法
WO2010018686A1 (fr) 2008-08-12 2010-02-18 日本曹達株式会社 Dérivé hétérocyclique azoté, et agent bactéricide agricole ou horticole
US8557738B2 (en) 2008-08-12 2013-10-15 Nippon Soda Co., Ltd. Nitrogen-containing heterocyclic derivative and fungicide for agricultural and horticultural use
JPWO2010125782A1 (ja) * 2009-04-28 2012-10-25 日本曹達株式会社 含窒素複素環化合物及び農園芸用殺菌剤
WO2010125782A1 (fr) * 2009-04-28 2010-11-04 日本曹達株式会社 Composé hétérocyclique contenant de l'azote et bactéricide agricole ou horticole
JP2011012017A (ja) * 2009-07-01 2011-01-20 Mitsui Chemicals Agro Inc キノリン系化合物を含有する植物病虫害防除剤および防除方法
US9062024B2 (en) 2009-09-28 2015-06-23 Nippon Soda Co., Ltd. Nitrogen-containing heterocyclic compound and salt thereof, and a fungicide for agricultural and horticultural use
WO2011037128A1 (fr) * 2009-09-28 2011-03-31 日本曹達株式会社 Composé hétérocyclique contenant de l'azote et sel de celui-ci et bactéricide à usage agricole et horticole
US11805779B2 (en) 2009-12-22 2023-11-07 Mitsui Chemicals Crop & Life Solutions, Inc. Plant disease control composition and method for controlling plant disease by applying the same
EP3150069A1 (fr) 2009-12-22 2017-04-05 Mitsui Chemicals Agro, Inc. Composition de contrôle de phytopathologie et procédé de contrôle de phytopathologie par application de la composition
US12310365B2 (en) 2009-12-22 2025-05-27 Mitsui Chemicals Crop & Life Solutions, Inc. Plant disease control composition and method for controlling plant disease by applying the same
CN105325435A (zh) * 2009-12-22 2016-02-17 三井化学Agro株式会社 植物病害防除组合物及施用其的植物病害的防除方法
CN105325423A (zh) * 2009-12-22 2016-02-17 三井化学Agro株式会社 植物病害防除组合物及施用其的植物病害的防除方法
US9288986B2 (en) 2009-12-22 2016-03-22 Mitsui Chemicals Agro, Inc. Plant disease control composition and method for controlling plant disease by applying the same
US10806141B2 (en) 2009-12-22 2020-10-20 Mitsui Chemicals Agro, Inc. Plant disease control composition and method for controlling plant disease by applying the same
CN102665414B (zh) * 2009-12-22 2015-11-25 三井化学Agro株式会社 植物病害防除组合物及施用其的植物病害的防除方法
US10091996B2 (en) 2009-12-22 2018-10-09 Mitsui Chemicals Agro, Inc. Plant disease control composition and method for controlling plant disease by applying the same
CN105325423B (zh) * 2009-12-22 2017-11-14 三井化学Agro株式会社 植物病害防除组合物及施用其的植物病害的防除方法
CN105325435B (zh) * 2009-12-22 2017-10-31 三井化学Agro株式会社 植物病害防除组合物及施用其的植物病害的防除方法
WO2011077514A1 (fr) 2009-12-22 2011-06-30 三井化学アグロ株式会社 Composition permettant de lutter contre des maladies végétales et procédé de lutte contre des maladies végétales par application de la composition
US8772200B2 (en) 2010-01-04 2014-07-08 Nippon Soda Co., Ltd. Nitrogen-containing heterocyclic compound and agricultural fungicide
JPWO2011081174A1 (ja) * 2010-01-04 2013-05-13 日本曹達株式会社 含窒素ヘテロ環化合物ならびに農園芸用殺菌剤
JP2011162472A (ja) * 2010-02-09 2011-08-25 Nippon Soda Co Ltd 含窒素ヘテロ環化合物またはその塩、ならびに農園芸用殺菌剤
US9060517B2 (en) 2011-05-20 2015-06-23 Nippon Soda Co., Ltd. Nitrogenated heterocyclic compound and agricultural or horticultural fungicide
WO2012161071A1 (fr) 2011-05-20 2012-11-29 日本曹達株式会社 Composé hétérocyclique azoté et agent bactéricide agricole ou horticole
WO2013047750A1 (fr) * 2011-09-29 2013-04-04 三井化学アグロ株式会社 Procédé de fabrication de dérivé de 3,4-dihydroisoquinoléine, et corps intermédiaire de cette fabrication
US9193706B2 (en) 2011-09-29 2015-11-24 Mitsui Chemicals Agro, Inc. Method for producing 3,4-dihydroisoquinoline derivatives and production intermediates of same
US9150538B2 (en) 2011-09-29 2015-10-06 Mitsui Chemicals Agro, Inc. Method for producing 4, 4-difluoro-3,4-dihydroisoquinoline derivatives
WO2013047751A1 (fr) * 2011-09-29 2013-04-04 三井化学アグロ株式会社 Procédé de fabrication de dérivé de 3,4-dihydroisoquinoléine
CN103814023B (zh) * 2011-09-29 2015-09-23 三井化学Agro株式会社 4,4-二氟-3,4-二氢异喹啉衍生物的制造方法
US9499515B2 (en) 2011-09-29 2016-11-22 Mitsui Chemicals Agro, Inc. Method for producing 3,4-dihydroisoquinoline derivatives and production intermediates of same
WO2013047749A1 (fr) * 2011-09-29 2013-04-04 三井化学アグロ株式会社 Procédé de fabrication de dérivé de 4,4-difluoro-3,4-dihydroisoquinoléine
JPWO2013047750A1 (ja) * 2011-09-29 2015-03-26 三井化学アグロ株式会社 ３，４−ジヒドロイソキノリン誘導体の製造方法およびそれらの製造中間体
JPWO2013047751A1 (ja) * 2011-09-29 2015-03-26 三井化学アグロ株式会社 ３，４−ジヒドロイソキノリン誘導体の製造方法
CN103814023A (zh) * 2011-09-29 2014-05-21 三井化学Agro株式会社 4，4－二氟－3，4－二氢异喹啉衍生物的制造方法
JPWO2013047749A1 (ja) * 2011-09-29 2015-03-26 三井化学アグロ株式会社 ４，４−ジフルオロ−３，４−ジヒドロイソキノリン誘導体の製造方法
US9795135B2 (en) 2013-07-24 2017-10-24 Bayer Cropscience Aktiengesellschaft Binary fungicidal composition
WO2015132133A1 (fr) * 2014-03-04 2015-09-11 Syngenta Participations Ag Dérivés hétérobicycliques microbiocides
JP2017508752A (ja) * 2014-03-04 2017-03-30 シンジェンタ パーティシペーションズ アーゲー 殺微生物性二環式複素環式誘導体
US9896454B2 (en) 2014-03-04 2018-02-20 Syngenta Participations Ag Microbiocidal heterobicyclic derivatives
US10201158B2 (en) 2014-03-20 2019-02-12 Mitsui Chemicals Agro, Inc. Plant disease control composition and method for controlling plant disease by application of same
WO2015141867A1 (fr) 2014-03-20 2015-09-24 Mitsui Chemicals Agro, Inc. Composition de lutte contre une maladie de plante, et procédé de lutte contre une maladie de plante par application de cette dernière
KR20160134727A (ko) 2014-03-20 2016-11-23 미쓰이가가쿠 아그로 가부시키가이샤 식물 병해 방제 조성물 및 그것을 시용하는 식물 병해의 방제 방법
US11064697B2 (en) 2015-07-24 2021-07-20 Basf Se Pyridine compounds useful for combating phytopathogenic fungi
JP2018525392A (ja) * 2015-08-12 2018-09-06 シンジェンタ パーティシペーションズ アーゲー 殺微生物二環式複素環式誘導体
US10906897B2 (en) 2015-08-12 2021-02-02 Syngenta Participations Ag Microbiocidal heterobicyclic derivatives
WO2017090664A1 (fr) * 2015-11-25 2017-06-01 三井化学アグロ株式会社 Composé quinoxalylisoquinoline
WO2018065182A1 (fr) * 2016-10-04 2018-04-12 Basf Se Composés de quinoléine réduits en tant qu'agents antifuni
WO2018116072A1 (fr) 2016-12-20 2018-06-28 Pi Industries Ltd. Composés hétérocycliques
CN106834135A (zh) * 2016-12-26 2017-06-13 西北农林科技大学 一种诱导葡萄痂囊腔菌产孢的方法
WO2018134127A1 (fr) * 2017-01-23 2018-07-26 Basf Se Composés de pyridine fongicides
WO2018184882A1 (fr) * 2017-04-06 2018-10-11 Basf Se Composés de pyridine
WO2018190326A1 (fr) * 2017-04-10 2018-10-18 三井化学アグロ株式会社 Composition de lutte contre les nuisibles contenant un composé pyridone et un composé à base de quinoléine et procédé de lutte contre les nuisibles, et nouveau composé à base de quinoléine
JP2019151631A (ja) * 2018-03-02 2019-09-12 国立大学法人 岡山大学 植物病害防除剤及び植物病害の防除方法
WO2022223376A1 (fr) 2021-04-20 2022-10-27 Syngenta Crop Protection Ag Dérivés de quinoléine/quinoxaline isoquinoline microbiocides
WO2024068656A1 (fr) 2022-09-28 2024-04-04 Syngenta Crop Protection Ag Compositions fongicides

Also Published As

Publication number Publication date
TW200740788A (en) 2007-11-01

Similar Documents

Publication Publication Date Title
WO2007011022A1 (fr) Dérivé de 3-(isoquinoline-1-yl)quinoline
CN108137570B (zh) 杀微生物的噁二唑衍生物
JP5502738B2 (ja) 殺有害生物剤として有用なスピロ複素環ピロリジンジオン誘導体
WO2005070917A1 (fr) 3-(dihydro(tetrahydro)isoquinolin-1-yl)quinolines
US5824802A (en) 1-alkyl-4-benzoyl-5-hydroxypyrazole compounds and their use as herbicides
US20100035756A1 (en) Triazolophyridine derivatives as herbicides
EP3197276B1 (fr) Pyridino/pyrimidino-thiazoles herbicides
RS54772B1 (sr) Antiparazitska jedinjenja dihidroazola i kompozicije koje ih sadrže
KR101350123B1 (ko) 1-알킬-5-벤조일-1ｈ-테트라졸 유도체의 제조 방법
TW200950703A (en) Pesticidal condensed-ring aryl compounds
EA019495B1 (ru) Спирогетероциклические n-оксипиперидины в качестве пестицидов
CN103124733B (zh) 除草的异噁唑并[5,4-b]吡啶
HU215210B (hu) N-aril-1,2,4-triazolo[1,5-a]piridin-2-szulfonamid-származékok, intermedierjeik: előállításuk, alkalmazásuk, valamint hatóanyagként ezeket a vegyületeket tartalmazó herbicid készítmények
WO2002038562A1 (fr) Derives de triazolone bicycliques et herbicides contenant ces derniers
JP2015504889A (ja) 除草性イソオキサゾロ［５，４−ｂ］ピリジン
EP2049498A1 (fr) Composés de pyrimidine pour la lutte contre les champignons nuisibles et le cancer
EP2855437A1 (fr) Thioamides d'acide n-(tétrazol-5-yl)- et n-(triazol-5-yl)aryle carboxylique et leur utilisation comme herbicides
TW201638076A (zh) 新穎之異噻唑醯胺類，其製備方法及其作為除草劑及／或植物生長調節劑之用途
EP2831084B1 (fr) Thiazolopyridinone à effet herbicide et insecticide
CN105777733B (zh) 一种含异恶唑啉的四氢邻苯二甲酰亚胺类化合物及其用途
WO2005095380A1 (fr) Compose amine cyclique et agent pesticide
EP1076656A2 (fr) Nouveaux herbicides
WO1997028127A1 (fr) Derives de pyridone et herbicides
PT2324010E (pt) Compostos insecticidas de fenil- ou de piridil-piperidina
AU2019266197B2 (en) Endoparasitic depsipeptides

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC DATED 11.04.2008

NENP Non-entry into the national phase

Ref country code: JP

122 Ep: pct application non-entry in european phase

Ref document number: 06768356

Country of ref document: EP

Kind code of ref document: A1