JP2002508369A - Herbicide 3- (benzoazol-4-yl) pyrimidinedione derivative - Google Patents

Abstract

  (57) [Summary] Formula I: Embedded image Wherein X represents oxygen or sulfur;¹Is hydrogen, amino, C₁~ C₆Alkyl or C₁~ C₆Represents haloalkyl; R^TwoIs hydrogen, halogen, C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₁~ C₆Alkylthio, C₁~ C₆Alkylsulfinyl or C₁~ C₆R represents alkylsulfonyl;^ThreeIs hydrogen, halogen or C₁~ C₆R represents alkyl;^FourRepresents hydrogen or halogen; R^FiveIs cyano, halogen, C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₁~ C ₆Alkoxy or C₁~ C₆Represents haloalkoxy; = Y- represents = NN- (R⁶)-, = C (ZR⁷) -N (R⁶)-, = C (ZR⁷) -O- or = C (ZR⁷) Represents -S-; R⁶Is C₁~ C₆Alkyl, C₁~ C_FourHaloalkyl, C_Three~ C₆Cycloalkyl, C_Three~ C₆Alkenyl, C_Three~ C₆Alkynyl, C₁~ C₆Alkylsulfonyl, (C ₁~ C₆Alkyl) carbonyl, (C₁~ C₆Haloalkyl) carbonyl, (C₁~ C₆Alkyl) thiocarbonyl, (C₁~ C₆Alkoxy) carbonyl, (C₁~ C ₆Alkoxy) thiocarbonyl or cyano, C₁~ C₆Alkoxy, C₁~ C₆Alkylthio, (C₁~ C₆Alkoxy) carbonyl, (C₁~ C₆Alkylamino) carbonyl, di (C₁~ C₆Alkyl) aminocarbonyl or (C₁~ C₆Alkyl) carbonyl optionally substituted with carbonyloxy₁~ C₆Z represents a chemical bond, oxygen, sulfur, -S (O)-, -S (O)_Two-, -NH- or -N (R⁸)-Represents; R⁷And R⁸Are independently of each other₁~ C₆Alkyl, C₁~ C₆Haloalkyl, hydroxy C₁~ C_FourAlkyl, cyano C₁~ C_FourAlkyl, C₁~ C_FourAlkoxy C₁~ C_FourAlkyl, C₁~ C_FourHaloalkoxy C₁~ C_FourAlkyl, C_Three~ C_FourAlkenyloxy C₁~ C_FourAlkyl, C_Three~ C_FourAlkynyloxy C₁~ C_FourAlkyl, C_Three~ C₈Cycloalkoxy C₁~ C_FourAlkyl, amino C₁~ C_FourAlkyl, C₁~ C_FourAlkylamino C₁~ C_FourAlkyl, di (C ₁~ C_FourAlkyl) amino C₁~ C_FourAlkyl, C₁~ C_FourAlkylthio C₁~ C_FourAlkyl, C₁~ C_FourHaloalkylthio C₁~ C_FourAlkyl, C_Three~ C_FourAlkenylthio C ₁~ C_FourAlkyl, C_Three~ C_FourAlkynylthio C₁~ C_FourAlkyl, C₁~ C_FourAlkylsulfinyl C₁~ C_FourAlkyl, C₁~ C_FourHaloalkylsulfinyl C₁~ C_FourAlkyl, C_Three~ C_FourAlkenylsulfinyl C₁~ C_FourAlkyl, C_Three~ C_FourAlkynyl sulfinyl C₁~ C_FourAlkyl, C₁~ C_FourAlkylsulfonyl C₁~ C_FourAlkyl, C₁~ C_FourHaloalkylsulfonyl C₁~ C_FourAlkyl, C_Three~ C_FourAlkenylsulfonyl C₁~ C_FourAlkyl, C_Three~ C_FourAlkynylsulfonyl C₁~ C_FourAlkyl, C_Three~ C₆Alkenyl, cyano C_Three~ C₆Alkenyl, C_Three~ C₆Haloalkenyl, C _Three~ C₆Alkynyl, cyano C_Three~ C₆Alkynyl, C_Three~ C₆Haloalkynyl, hydroxycarbonyl C₁~ C_FourAlkyl, (C₁~ C_FourAlkoxy) carbonyl C₁~ C_FourAlkyl, (C₁~ C_FourAlkylthio) carbonyl C₁~ C_FourAlkyl, aminocarbonyl C₁~ C_FourAlkyl, (C₁~ C_FourAlkylamino) carbonyl C₁~ C_FourAlkyl, di (C₁~ C_FourAlkyl) aminocarbonyl C₁~ C_FourAlkyl, di (C ₁~ C_FourAlkyl) phosphonyl C₁~ C_FourAlkyl, C_Three~ C₈Cycloalkyl, C_Three~ C₈Cycloalkyl C₁~ C_FourAlkyl, phenyl, phenyl C₁~ C_FourAlkyl, 3- to 7-membered heterocyclyl or heterocyclyl C₁~ C_FourAlkyl, wherein the heterocyclyl may each have a carbonyl or thiocarbonyl ring member, and the cycloalkyl, phenyl and heterocyclyl rings each have from 1 to 4 of the following groups: cyano, nitro, amino, Hydroxyl, carboxyl, halogen, C₁~ C_FourAlkyl, C₁~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourHaloalkoxy, C₁~ C_FourAlkylthio, C₁~ C_FourHaloalkylthio, C₁~ C_FourAlkylsulfonyl, C₁~ C_FourHaloalkylsulfonyl, (C₁~ C_FourAlkoxy) carbonyl, (C₁~ C_FourAlkyl) carbonyl, (C₁~ C_FourHaloalkyl) carbonyl, (C₁~ C_FourAlkyl) carbonyloxy, (C₁~ C_FourHaloalkyl) carbonyloxy and di (C₁~ C_FourAlkyl) amino, or if Z is a chemical bond, optionally⁷Further comprises hydrogen, hydroxyl, cyano, mercapto, amino, halogen, -CH (OH) -CH_Two-R⁹, -CH (halogen) -CH_Two-R⁹, -CH_Two-CH (halogen) -R⁹, -CH = CH-R⁹Or -CH = C (halogen) -R⁹(This R⁹Is hydroxycarbonyl, (C₁~ C_FourAlkoxy) carbonyl, (C₁~ C_FourAlkylthio) carbonyl, aminocarbonyl, (C₁~ C_FourAlkylamino) carbonyl or di (C₁~ C_FourAlkyl) representing aminocarbonyl) or R⁷And R⁸Are united into one to four C₁~ C_FourAn alkyl group, or one or two (C₁~ C_FourWhich may have an alkoxy) carbonyl group to form a 1,3-propylene, tetramethylene, pentamethylene or ethyleneoxyethylene chain]. Or an agriculturally useful salt of Compound I.

Description

DETAILED DESCRIPTION OF THE INVENTION

The present invention relates to a compound of formula I:

[0002]

Embedded imageWherein X represents oxygen or sulfur;¹Is hydrogen, amino, C₁~ C₆Alkyl or C₁~ C₆Represents haloalkyl; R^TwoIs hydrogen, halogen, C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₁~ C₆ Alkylthio, C₁~ C₆Alkylsulfinyl or C₁~ C₆Alkylsulfonyl
R;^ThreeIs hydrogen, halogen or C₁~ C₆R represents alkyl;^FourRepresents hydrogen or halogen; R^FiveIs cyano, halogen, C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₁~ C ₆ Alkoxy or C₁~ C₆Represents haloalkoxy; = Y- represents = NN- (R⁶)-, = C (ZR⁷) -N (R⁶)-, = C (ZR⁷)
-O- or = C (ZR⁷) Represents -S-; R⁶Is C₁~ C₆Alkyl, C₁~ C_FourHaloalkyl, C_Three~ C₆Cycloalkyl, C_Three~ C₆Alkenyl, C_Three~ C₆Alkynyl, C₁~ C₆Alkylsulfonyl, (C ₁ ~ C₆Alkyl) carbonyl, (C₁~ C₆Haloalkyl) carbonyl, (C₁~ C₆Alkyl) thiocarbonyl, (C₁~ C₆Alkoxy) carbonyl, (C₁~ C ₆ Alkoxy) thiocarbonyl or cyano, C₁~ C₆Alkoxy, C₁~ C₆Alkylthio, (C₁~ C₆Alkoxy) carbonyl, (C₁~ C₆Alkylamino)
Carbonyl, di (C₁~ C₆Alkyl) aminocarbonyl or (C₁~ C₆Al
C) optionally substituted with carbonyloxy₁~ C₆Z represents a chemical bond, oxygen, sulfur, -S (O)-, -S (O)_Two-, -NH- or -N (R⁸R)⁷And R⁸Are independently of each other₁~ C₆Alkyl, C₁~ C₆Haloal
Kill, hydroxy C₁~ C_FourAlkyl, cyano C₁~ C_FourAlkyl, C₁~ C_FourArco
Kishi C₁~ C_FourAlkyl, C₁~ C_FourHaloalkoxy C₁~ C_FourAlkyl, C_Three~ C_FourA
Lucenyloxy C₁~ C_FourAlkyl, C_Three~ C_FourAlkynyloxy C₁~ C_FourAlkyl
, C_Three~ C₈Cycloalkoxy C₁~ C_FourAlkyl, amino C₁~ C_FourAlkyl, C₁~ C_FourAlkylamino C₁~ C_FourAlkyl, di (C ₁ ~ C_FourAlkyl) amino C₁~ C_FourAlkyl, C₁~ C_FourAlkylthio C₁~ C_FourAl
Kill, C₁~ C_FourHaloalkylthio C₁~ C_FourAlkyl, C_Three~ C_FourAlkenylthio C ₁ ~ C_FourAlkyl, C_Three~ C_FourAlkynylthio C₁~ C_FourAlkyl, C₁~ C_FourAlkyl
Sulfinyl C₁~ C_FourAlkyl, C₁~ C_FourHaloalkylsulfinyl C₁~ C_FourA
Luquil, C_Three~ C_FourAlkenylsulfinyl C₁~ C_FourAlkyl, C_Three~ C_FourAlkini
Rusulfinyl C₁~ C_FourAlkyl, C₁~ C_FourAlkylsulfonyl C₁~ C_FourArchi
Le, C₁~ C_FourHaloalkylsulfonyl C₁~ C_FourAlkyl, C_Three~ C_FourAlkenyls
Ruphonyl C₁~ C_FourAlkyl, C_Three~ C_FourAlkynylsulfonyl C₁~ C_FourAlkyl,
C_Three~ C₆Alkenyl, cyano C_Three~ C₆Alkenyl, C_Three~ C₆Haloalkenyl, C _Three ~ C₆Alkynyl, cyano C_Three~ C₆Alkynyl, C_Three~ C₆Haloalkynyl, hide
Roxycarbonyl C₁~ C_FourAlkyl, (C₁~ C_FourAlkoxy) carbonyl C₁~ C_FourAlkyl, (C₁~ C_FourAlkylthio) carbonyl C₁~ C_FourAlkyl, amino carbonyl C₁~ C_FourAlkyl, (C₁~ C_FourAlkylamino) carbonyl C₁~ C_Four Alkyl, di (C₁~ C_FourAlkyl) aminocarbonyl C₁~ C_FourAlkyl, di (C ₁ ~ C_FourAlkyl) phosphonyl C₁~ C_FourAlkyl, C_Three~ C₈Cycloalkyl, C_Three ~ C₈Cycloalkyl C₁~ C_FourAlkyl, phenyl, phenyl C₁~ C_FourAlkyl, 3- to 7-membered heterocyclyl or heterocyclyl C₁~ C_FourAlkyl (this hetero
Cycyl may each have a carbonyl or thiocarbonyl ring member)
And the cycloalkyl, phenyl and heterocyclyl rings each have from 1 to 4
Groups: cyano, nitro, amino, hydroxyl, carboxyl, halogen, C₁ ~ C_FourAlkyl, C₁~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourHaloalkoxy, C₁~ C_FourAlkylthio, C₁~ C_FourHaloalkylthio, C₁~ C_FourArchi
Rusulfonyl, C₁~ C_FourHaloalkylsulfonyl, (C₁~ C_FourAlkoxy) cal
Bonil, (C₁~ C_FourAlkyl) carbonyl, (C₁~ C_FourHaloalkyl) carboni
Le, (C₁~ C_FourAlkyl) carbonyloxy, (C₁~ C_FourHaloalkyl) carbo
Nyloxy and di (C₁~ C_FourHaving a substituent selected from alkyl) amino
Or if Z is a chemical bond, optionally R⁷Further comprises hydrogen, hydroxyl, cyano, mercapto, amino, halogen, -CH (OH) -CH_Two-R⁹, -CH (c
Rogen) -CH_Two-R⁹, -CH_Two-CH (halogen) -R⁹, -CH = CH-R⁹ Or -CH = C (halogen) -R⁹(This R⁹Is hydroxycarbonyl, (C₁~ C_FourAlkoxy) carbonyl, (C₁~ C_FourAlkylthio) carbonyl, aminocarbonyl, (C₁~ C_FourAlkylamino) carbonyl or di (C₁~ C_FourAlkyl)
Represents aminocarbonyl) or R⁷And R⁸Are united into one to four C₁~ C_FourAn alkyl group, or one or two
(C₁~ C_Four1,3-propyl which may have an alkoxy) carbonyl group
Forms a len, tetramethylene, pentamethylene or ethyleneoxyethylene chain
A novel 3- (benzoazol-4-yl) pyrimidinedione derivative represented by the formula:
And agriculturally useful salts of compound I.

The invention further relates to the use of compound I as a herbicide, a herbicide composition comprising compound I as an active substance, a method for producing a compound I and a herbicide composition using compound I, And the intermediates of formulas III, IV and V for the preparation of compounds I.

[0004] WO 97/08170 includes certain 3- (benzox) as a herbicide.
) / Benzothiazol-7-yl) -6- (trifluoromethyl) uracil is disclosed. Other 3- (benzothiazol-7-yl) uracils and their use as herbicides and for drying / deciduous plants are described in WO 97/0817.
1. In particular, certain 3
-Benzisoxazol-7-yl-2,4- (1H, 3H) pyrimidine diion is the problem of WO 97/12886.

[0005] It is therefore an object of the present invention to provide novel herbicidally active urea compounds in which the target control of undesired plants is better than can be achieved with known compounds.

[0006] The present inventors have determined that the above object is achieved by providing 3- (benzoazol-4-yl) of formula I according to the present invention.
It has been found that this can be achieved by pyrimidinedione derivatives.

The present inventors have further found a herbicidal composition containing Compound I and exhibiting a very good herbicidal action. In addition, the present inventors have found methods for preparing these compositions and for controlling unwanted vegetation using Compound I.

[0008] Depending on the mode of substitution, the compounds of the formula I can have one or more chiral centers, in which case they exist as enantiomeric or diastereomeric mixtures. When compound I has at least one olefinic group, E / Z isomers may be present. The invention relates not only to the pure enantiomers or diastereomers, but also to mixtures thereof.

Formula I only illustrates one of the possible forms for some of the compounds of the present invention. Thus, these compounds I (R ⁷ are hydroxyl) may represent as a tautomer I 'a [-N = C (OH) - ← → -NH-CO-].

[0010]

Embedded image

Suitable agriculturally useful salts are mainly salts of these cations or acid addition salts of these acids, which cations or anions each have a detrimental effect on the herbicidal action of compound I. Do not give. Thus, suitable cations are, in particular, alkali metal ions, preferably sodium and potassium ions, alkaline earth metal ions, preferably calcium, magnesium and barium ions, and transition metal ions, preferably manganese, copper, zinc and iron ions. And, if necessary, an ammonium salt optionally having ₁ to ₄ C ₁ -C ₄ alkyl groups and / or phenyl or benzyl groups, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzyl Ammonium, and further, a phosphonium ion, a sulfonium ion (preferably, tri (C ₁ -C ₄ alkyl) sulfonium) and a sulfoxonium ion (preferably, tri (C ₁ -C ₄ alkyl) sulfoxonium.

Useful acid addition salt anions are mainly chloride, bromide, fluoride, bisulfate,
Sulfates, dihydrogen phosphates, phosphates, hydrogen phosphates, nitrates, bicarbonates, carbonates,
Xafluorosilicates, hexafluorophosphates, benzoates and also C ₁ ~ C_FourAnions of alkanoic acids, preferably formate, acetate, propiona
And butyrate. These are converted to the acid of the anion corresponding to I (preferably
Hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid).
Can be.

An organic group described in the definition of the substituents R ^{1 to} R ³ and R ^{5 to} R ⁹ , or a cycloalkyl ring,
The organic groups described as the groups of the phenyl ring and the heterocyclic ring represent common terms such as halogen, for example, to exemplify the members of the individual groups. All carbon chains are all alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, aminoalkyl, hydroxycarbonylalkyl, aminocarbonylalkyl, phenylalkyl, heterocyclylalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkyl Sulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkenyl, haloalkenyl, cyanoalkenyl, alkenyloxy, alkenylthio, alkenylsulfinyl,
The alkenylsulfonyl, alkynyl, haloalkynyl, cyanoalkynyl, alkynyloxy, alkynylthio, alkynylsulfinyl and alkynylsulfonyl moiety may be straight-chain or branched. The halogenated substituent preferably has 1 to 5 identical or different halogen atoms. Halogen atoms are each fluorine, chlorine, bromine or iodine.

Examples of other meanings include: C₁~ C_FourAlkyl: CH_Three, C_TwoH_Five, CH_Three-C_TwoH_Five, CH (CH_Three)_Two, N-bu
Chill, CH (CH_Three) -C_TwoH_Five, CH_Two-CH (CH_Three)_TwoOr C (CH_Three)_ThreeC₁~ C_FourHaloalkyl: partially or completely fluorine, chlorine, bromine and / or iodine
C substituted with a prime₁~ C_FourAlkyl, ie CH_TwoF, CHF_Two, CF_Three, CH_TwoCl, CH (Cl)_Two, C (Cl)_Three, Chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl
, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2
2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,
2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-
Trichloroethyl, C_TwoF_Five, 2-fluoropropyl, 3-fluoropropyl, 2
, 2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl
, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-
Bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloro
Propyl, CH_Two-C_TwoF_Five, CF_Two-C_TwoF_Five, 1- (CH_TwoF) -2-Fluoroethyl, 1- (CH_TwoCl) -2-chloroethyl, 1- (CH_TwoBr) -2-bromo
Ethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonaf
Fluorobutyl; C₁-C₆Alkyl: C as described above₁-C_FourAlkyl, or, for example, n-pentyl,
1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl
Ropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,
2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methyl
Pentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl
Chill, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl
Chill, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1
, 2-Trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1
-Methylpropyl or 1-ethyl-2-methylpropyl, preferably CH_Three, C_Two H_Five, CH_Two-C_TwoH_Five, CH (CH_Three)_Two, N-butyl, C (CH_Three)_Three, N-pliers
Or n-hexyl; C₁-C₆Haloalkyl: partially or completely fluorine, chlorine, bromine and / or iodine
The above-mentioned C substituted with₁-C₆Alkyl, ie C₁-C_FourStated in haloalkyl
One of the groups, or 5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5
-Bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro
-1-pentyl, undecafluoropentyl, 6-fluoro-1-hexyl, 6
-Chloro-1-hexyl, 6-bromo-1-hexyl, 6-iodo-1-hexyl
6,6,6-trichloro-1-hexyl or dodecafluorohexyl; cyano C₁-C_FourAlkyl: CH_TwoCN, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanopro
1-yl, 1-cyanobuta-1-yl, 2-cyanobuta-1-yl, 3-si
Anobta-1-yl, 4-cyanobuta-1-yl, 1-cyanobuta-2-yl,
2-cyanobuta-2-yl, 3-cyanobuta-2-yl, 4-cyanobuta-2-yl
Il, 1- (CH_TwoCN) -eth-1-yl, 1- (CH_TwoCN) -1- (CH_Three ) -Eth-1-yl or 1- (CH_TwoCN) -prop-1-yl; hydroxy C₁-C_FourAlkyl: for example, CH_TwoOH, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxyprop-1-yl, 2-hydroxypro
Pa-1-yl, 3-hydroxyprop-1-yl, 1-hydroxybut-1-y
2-Hydroxybut-1-yl, 3-hydroxybut-1-yl, 4-hydr
Roxybut-1-yl, 1-hydroxybut-2-yl, 2-hydroxy-2-
Yl, 3-hydroxybut-2-yl, 4-hydroxybut-2-yl, 1- (
CH_TwoOH) eth-1-yl, 1- (CH_TwoOH) -1- (CH_Three) -Eth-1-yl or 1- (CH_TwoOH) prop-1-yl; amino C₁-C_FourAlkyl: CH_TwoNH_Two, 1-aminoethyl, 2-aminoethyl
, 1-aminoprop-1-yl, 2-aminoprop-1-yl, 3-aminoprop
Pa-1-yl, 1-aminobut-1-yl, 2-aminobut-1-yl, 3-a
Minobut-1-yl, 4-aminobut-1-yl, 1-aminobut-2-yl,
2-aminobut-2-yl, 3-aminobut-2-yl, 4-aminobut-2-
Il, 1- (CH_TwoNH_Two) Eth-1-yl, 1- (CH_TwoNH_Two) -1- (CH_Three ) -Eth-1-yl or 1- (CH_TwoNH_Two) Prop-1-yl; hydroxycarbonyl C₁-C_FourAlkyl: for example, CH_TwoCOOH, 1- (COOH) ethyl, 2- (COOH) ethyl, 1- (COOH) prop-1-yl
, 2- (COOH) prop-1-yl, 3- (COOH) prop-1-yl, 1
-(COOH) but-1-yl, 2- (COOH) but-1-yl, 3- (CO
OH) but-1-yl, 4- (COOH) but-1-yl, 1- (COOH) butyl
Ta-2-yl, 2- (COOH) but-2-yl, 3- (COOH) but-2-
Yl, 4- (COOH) but-2-yl, 1- (CH_TwoCOOH) eth-1-yl, 1- (CH_TwoCOOH) -1- (CH_Three) -Eth-1-yl or 1- (CH_Two COOH) prop-1-yl; aminocarbonyl C₁-C_FourAlkyl: CH_TwoCONH_Two, 1- (CONH_Two) Ethyl, 2- (CONH)_Two) Ethyl, 1- (CONH)_Two) Prop-1-yl, 2- (
CONH_Two) Prop-1-yl, 3- (CONH)_Two) Prop-1-yl, 1- (C
ONH_Two) But-1-yl, 2- (CONH)_Two) But-1-yl, 3- (CONH) _Two ) But-1-yl, 4- (CONH_Two) But-1-yl, 1- (CONH)_Two) But-2-yl, 2- (CONH_Two) -2-yl, 3- (CONH)_Two) Pig-2-a
4- (CONH_Two) But-2-yl, 1- (CH_TwoCONH_Two) Eth-1-yl, 1- (CH_TwoCONH_Two) -1- (CH_Three) -Eth-1-yl or 1- (CH_Two CONH_Two) Prop-1-yl; heterocyclyl C₁-C_FourAlkyl: heterocyclylmethyl, 1-heterocyclyl
Ethyl, 2-heterocyclylethyl, 1-heterocyclylprop-1-yl,
2-heterocyclylprop-1-yl, 3-heterocyclylprop-1-yl,
1-heterocyclylbut-1-yl, 2-heterocyclylbut-1-yl, 3-
Heterocyclylbut-1-yl, 4-heterocyclylbut-1-yl, 1-hetero
Rocyclylbut-2-yl, 2-heterocyclylbut-2-yl, 3-heterocyclyl
Krillbut-2-yl, 4-heterocyclylbut-2-yl, 1- (heterocyclyl
Rylmethyl) eth-1-yl, 1- (heterocyclylmethyl) -1- (methyl)
Eth-1-yl or 1- (heterocyclylmethyl) prop-1-yl, preferably
Is heterocyclylmethyl or 2- (heterocyclyl) ethyl; C₁-C_FourAlkoxy: OCH_Three, OC_TwoH_Five, OCH_Two-C_TwoH_Five, OCH (CH_Three )_Two, N-butoxy, OCH (CH_Three) -C_TwoH_Five, OCH_Two-CH (CH_Three)_TwoOr C (CH_Three)_Three, Preferably OCH_Three, OC_TwoH_FiveOr OCH (CH_Three)_TwoC₁-C_FourHaloalkoxy: partially or completely fluorine, chlorine, bromine and / or
The above-mentioned C substituted by urine₁-C_FourAlkoxy, ie, OCH_TwoF, OCHF_Two, O
CF_Three, OCH_TwoCl, OCH (Cl)_Two, OC (Cl)_Three, Chlorofluoromethoki
Si, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroeth
Xy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2
-Difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-
Fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro
B-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC_TwoF_Five, 2-
Fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy
, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy
Si, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy
3,3,3-trifluoropropyl, 3,3,3-trichloropropoxy,
OCH_Two-C_TwoF_Five, OCF_Two-C_TwoF_Five, 1- (CH_TwoF) -2-Fluoroethoxy, 1- (CH_TwoCl) -2-chloroethoxy, 1- (CH_TwoBr) -2-bromoe
Toxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or
Nonafluorobutoxy, preferably OCHF_Two, OCF_Three, Dichlorofluorometh
Xy, chlorodifluoromethoxy or 2,2,2-trifluoroethoxy; C₁-C₆Alkoxy: C as described above₁-C_FourAlkoxy or, for example, n-pent
Xy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2
-Dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1,1-dimethyl
Tylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-meth
Tilpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethyl
Tilbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2
-Dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,
1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy
, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or
1-ethyl-2-methylpropoxy, preferably OCH_Three, OC_TwoH_Five, OCH_Two−
C_TwoH_Five, OCH (CH_Three)_Two, N-butoxy, OC (CH_Three)_Three, N-pentoxy or
Is n-hexoxy; C₁-C₆Haloalkoxy: partially or completely fluorine, chlorine, bromine and / or
The above-mentioned C substituted by urine₁-C₆Alkoxy, ie, C₁-C_FourWith haloalkoxy
One of the groups mentioned, or 5-fluoro-1-pentoxy, 5-chloro-1-pen
Toxic, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5,5
5-trichloro-1-pentoxy, undecafluoropentoxy, 6-fluoro
-1-hexoxy, 6-chloro-1-hexoxy, 6-bromo-1-hexoxy
, 6-iodo-1-hexoxy, 6,6,6-trichloro-1-hexoxy or
Dodecafluorohexoxy; C₁-C_FourAlkylthio: SCH_Three, SC_TwoH_Five, SCH_Two-C_TwoH_Five, SCH (CH _Three )_Two, N-butylthio, SCH (CH_Three) -C_TwoH_Five, SCH_Two-CH (CH_Three)_Threeor
Is SC (CH_Three)_Three, Preferably SCH_ThreeOr SC_TwoH_FiveC₁-C_FourHaloalkylthio: partially or completely fluorine, chlorine, bromine and / or
The above-mentioned C substituted by iodine₁-C_FourAlkylthio, ie, SCH_TwoF, SCHF_Two , SCF_Three, SCH_TwoCl, SCH (Cl)_Two, SC (Cl)_Three, Chlorofluorome
Tylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-f
Fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodo
Ethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethyl
Thio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoro
Ethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-tric
Loroethylthio, SC_TwoF_Five2,2-fluoropropylthio, 3-fluoropropyl
Thio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2
-Chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio
E, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifur
Oropropylthio, 3,3,3-trichloropropylthio, SCH_Two-C_TwoF_Five, SCF_Two-C_TwoF_Five, 1- (CH_TwoF) -2-Fluoroethylthio, 1- (CH_TwoCl) -2-Chloroethylthio, 1- (CH_TwoBr) -2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or SC
F_Two-CF_Two-C_TwoF_Five, Preferably SCH_TwoF, SCHF_Two, Dichlorofluorome
Tylthio, chlorodifluoromethylthio or 2,2,2-trifluoroethylthio
E; C₁-C₆Alkylthio: C as described above₁-C_FourAlkylthio or, for example, n-pen
Tylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio
E, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylchi
E, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methyl
Rupentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methyl
Rupentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio,
1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethyl
Butylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethyl
Butylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylp
Ropirthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methyl
Propylthio, preferably SCH_Three, SC_TwoH_Five, SCH_Two-C_TwoH_Five, SCH (CH _Three )_Two, N-butylthio, SC (CH_Three)_Three, N-pentylthio or n-hexylchi
E; C₁-C_FourAlkoxy C₁-C_FourAlkyl: C as described above₁-C_FourSubstituted with alkoxy
C₁-C_FourAlkyl, ie CH_TwoOCH_Three, CH_TwoOC_TwoH_Five, N-propoxymethyl, CH_Two-OCH (CH_Three)_Two, N-butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, CH_Two-OC (CH_Three)_Three2- (methoxy) ethyl, 2- (ethoxy) ethyl, 2- (n-propoxy) ethyl,
2- (1-methylethoxy) ethyl, 2- (n-butoxy) ethyl, 2- (1-
Methylpropoxy) ethyl, 2- (2-methylpropoxy) ethyl, 2- (1,
1-dimethylethoxy) ethyl, 2- (methoxy) propyl, 2- (ethoxy)
Propyl, 2- (n-propoxy) propyl, 2- (1-methylethoxy) pro
Pill, 2- (n-butoxy) propyl, 2- (1-methylpropoxy) propyl
, 2- (2-methylpropoxy) propyl, 2- (1,1-dimethylethoxy)
Propyl, 3- (methoxy) propyl, 3- (ethoxy) propyl, 3- (n-
Propoxy) propyl, 3- (1-methylethoxy) propyl, 3- (n-but
Xy) propyl, 3- (1-methylpropoxy) propyl, 3- (2-methylprop
(Ropoxy) propyl, 3- (1,1-dimethylethoxy) propyl, 2- (meth
Xy) butyl, 2- (ethoxy) butyl, 2- (n-propoxy) butyl, 2-
(1-methylethoxy) butyl, 2- (n-butoxy) butyl, 2- (1-methyl)
Rupropoxy) butyl, 2- (2-methylpropoxy) butyl, 2- (1,1-
Dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl
, 3- (n-propoxy) butyl, 3- (1-methylethoxy) butyl, 3- (
n-butoxy) butyl, 3- (1-methylpropoxy) butyl, 3- (2-methyl
Rupropoxy) butyl, 3- (1,1-dimethylethoxy) butyl, 4- (meth
Xy) butyl, 4- (ethoxy) butyl, 4- (n-propoxy) butyl, 4-
(1-methylethoxy) butyl, 4- (n-butoxy) butyl, 4- (1-methyl
Rupropoxy) butyl, 4- (2-methylpropoxy) butyl or 4- (1,1
-Dimethylethoxy) butyl, preferably CH_TwoOCH_Three, CH_TwoOC_TwoH_Five, 2- (OCH_Three) Ethyl or 2- (OC_TwoH_Five) Ethyl; C₁-C_FourHaloalkoxy C₁-C_FourAlkyl: C as described above₁-C_FourWith haloalkoxy
Replaced C₁-C_FourAlkyl, for example 2- (OCHF)_Two) Ethyl, 2- (OC F_Three) Ethyl or 2- (OC_TwoF_Five) Ethyl; C₁-C_FourAlkylthio C₁-C_FourAlkyl: C as described above₁-C_FourSubstitute with alkylthio
Done C₁-C_FourAlkyl, ie CH_TwoSCH_Three, CH_TwoSC_TwoH_Five, N-propylthiomethyl, CH_TwoSCH (CH_Three)_Two, N-butylthiomethyl, (1-methylpropylthio) methyl, (2-methylpropylthio) methyl, CH_TwoSC (CH_Three)_Three , 2- (methylthio) ethyl, 2- (ethylthio) ethyl, 2- (n-propyl)
Thio) ethyl, 2- (1-methylethylthio) ethyl, 2- (n-butylthio)
Ethyl, 2- (1-methylpropylthio) ethyl, 2- (2-methylpropylthio)
E) Ethyl, 2- (1,1-dimethylethylthio) ethyl, 2- (methylthio)
Propyl, 2- (ethylthio) propyl, 2- (n-propylthio) propyl,
2- (1-methylethylthio) propyl, 2- (n-butylthio) propyl, 2
-(1-methylpropylthio) propyl, 2- (2-methylpropylthio) pro
Pill, 2- (1,1-dimethylethylthio) propyl, 3- (methylthio) pro
Pill, 3- (ethylthio) propyl, 3- (n-propylthio) propyl, 3-
(1-methylethylthio) propyl, 3- (n-butylthio) propyl, 3- (
1-methylpropylthio) propyl, 3- (2-methylpropylthio) propyl
3- (1,1-dimethylethylthio) propyl, 2- (methylthio) butyl,
2- (ethylthio) butyl, 2- (n-propylthio) butyl, 2- (1-methyl
Ruethylthio) butyl, 2- (n-butylthio) butyl, 2- (1-methylpro
Pyrthio) butyl, 2- (2-methylpropylthio) butyl, 2- (1,1-di
Methylethylthio) butyl, 3- (methylthio) butyl, 3- (ethylthio) butyl
Tyl, 3- (n-propylthio) butyl, 3- (1-methylethylthio) butyl
, 3- (n-butylthio) butyl, 3- (1-methylpropylthio) butyl,
-(2-methylpropylthio) butyl, 3- (1,1-dimethylethylthio) butyl
Butyl, 4- (methylthio) butyl, 4- (ethylthio) butyl, 4- (n-pro
Pyrthio) butyl, 4- (1-methylethylthio) butyl, 4- (n-butylthio)
E) butyl, 4- (1-methylpropylthio) butyl, 4- (2-methylpropyl
Ruthio) butyl or 4- (1,1-dimethylethylthio) butyl, preferably C
H_TwoSCH_Three, CH_TwoSC_TwoH_Five, 2- (SCH_Three) Ethyl or 2- (SC_TwoH_Five) Etch
Le; C₁~ C_FourHaloalkylthio C₁~ C_FourAlkyl: C as described above₁~ C_FourHaloalkyl
C replaced with E₁~ C_FourAlkyl, that is, 2- (SCHF_Two) Ethyl, 2- (SC F_Three) Ethyl or 2- (SC_TwoF_Five) Ethyl; (C₁-C_FourAlkyl) carbonyl: CO—CH_Three, CO-C_TwoH_Five, CO-CH_Two -C_TwoH_Five, COCH (CH_Three)_Two, N-butylcarbonyl, CO-CH (CH_Three) -C_TwoH_Five, CO-CH_Two-CH (CH_Three)_TwoOr CO-C (CH_Three)_Three, Preferably CO-CH_ThreeOr CO-C_TwoH_Five,; (C₁-C_FourHaloalkyl) carbonyl: partially or completely fluorine, chlorine, bromine
And / or (C) substituted with iodine.₁-C_FourAlkyl) carbonyl group, immediately
Chi COCH_TwoF, COCHF_Two, COCF_Three, COCH_TwoCl, COCH (Cl)_Two , COC (Cl)_Three, Chlorofluoromethylcarbonyl, dichlorofluoromethylcarbonyl, chlorodifluoromethylcarbonyl, 2-fluoroethylcarbo
Nil, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodo
Ethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trif
Fluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-
Loro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoro
Ethylcarbonyl, 2,2,2-trichloroethylcarbonyl, COC_TwoF_Five, 2
-Fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-di
Fluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-
Loropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloroprop
Propyl carbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbo
Nil, 3,3,3-trifluoropropylcarbonyl, 3,3,3-trichloro
Propyl carbonyl, COCH_TwoC_TwoF_Five, COCF_TwoC_TwoF_Five, 1- (CH_TwoF) -2-Fluoroethylcarbonyl, 1- (CH_TwoCl) -2-chloroethylcarbonyl, 1- (CH_TwoBr) -2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or
Nafluorobutylcarbonyl, preferably COCF_Three, COCH_TwoCl or 2,2
, 2-trifluoroethylcarbonyl, (C₁-C₆Alkyl) carbonyl: (C₁-C_FourAlkyl) carbonyl group
Or n-pentyl-CO, 1-methylbutyl-CO, 2-meth
Butylbutyl-CO, 3-methylbutyl-CO, 2,2-dimethylpropyl-CO
, 1-ethylpropyl-CO, n-hexyl-CO, 1,1-dimethylpropyl
-CO, 1,2-dimethylpropyl-CO, 1-methylpentyl-CO, 2-me
Tylpentyl-CO, 3-methylpentyl-CO, 4-methylpentyl-CO,
1,1-dimethylbutyl-CO, 1,2-dimethylbutyl-CO, 1,3-dimethyl
Butylbutyl-CO, 2,2-dimethylbutyl-CO, 2,3-dimethylbutyl-
CO, 3,3-dimethylbutyl-CO, 1-ethylbutyl-CO, 2-ethylbutyl
Cyl-CO, 1,1,2-trimethylpropyl-CO, 1,2,2-trimethyl
Propyl-CO, 1-ethyl-1-methylpropyl-CO, or 1-ethyl-2
-Methylpropyl-CO, preferably COCH_Three, COC_TwoH_Five, COCH_TwoC_TwoH_Five , COCH (CH_Three)_Two, N-butyl-CO, COC (CH_Three)_Three, CO (n-C_Five H₁₁) Or CO (n-C₆H₁₃) ,; (C₁-C₆-Haloalkyl) carbonyl: partially or completely fluorine, chlorine, odor
(C) substituted with iodine and / or iodine₁-C₆Alkyl) carbonyl residue,
That is, COCH_TwoF, COCHF_Two, COCF_Three, COCH_TwoCl, COCH (Cl) _Two , COC (Cl)_Three, Chlorofluoromethylcarbonyl, dichlorofluoromethyl
Carbonyl, chlorodifluoromethylcarbonyl, 2-fluoroethylcarbo
Nil, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodo
Ethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trif
Fluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-
Loro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoro
Ethylcarbonyl, 2,2,2-trichloroethylcarbonyl, COC_TwoF_Five, 2
-Fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-di
Fluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-
Loropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloroprop
Propyl carbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbo
Nil, 3,3,3-trifluoropropylcarbonyl, 3,3,3-trichloro
Propyl carbonyl, COCH_TwoC_TwoF_Five, COCF_TwoC_TwoF_Five, 1- (CH_TwoF) -2-Fluoroethylcarbonyl, 1- (CH_TwoCl) -2-chloroethylcarbonyl, 1- (CH_TwoBr) -2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl, or
Nonafluorobutylcarbonyl, preferably COCF_Three, COCH_TwoCl or 2,
2,2-trifluoroethylcarbonyl; (C₁-C_FourAlkyl) carbonyloxy: OCOCH_Three, OCOC_TwoH_Five, OC O-CH_TwoC_TwoH_Five, OCOCH (CH_Three)_Two, OCOCH_TwoCH_TwoC_TwoH_Five, OCOH (CH_Three) C_TwoH_Five, OCOCH_TwoCH (CH_Three)_TwoOr OCOC (CH_Three)_Three, Good
Preferably OCOCH_ThreeOr OCOC_TwoH_Five; (C₁-C_FourHaloalkyl) carbonyloxy: partially or completely fluorine, chlorine
(C) substituted with bromine and / or iodine,₁-C_FourAlkyl) carbonyl,
For example, OCOCH_TwoF, OCOCHF_Two, OCOCF_Three, OCOCH_TwoCl, OCO
CH (Cl)_Two, OCOC (Cl)_Three, Chlorofluoromethylcarbonyloxy,
Dichlorofluoromethylcarbonyloxy, chlorodifluoromethylcarbonyl
Oxy, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy
Xy, 2-bromoethylcarbonyloxy, 2-iodoethylcarbonyloxy
, 2,2-difluoroethylcarbonyloxy, 2,2,2-trifluoroethyl
Carbonyloxy, 2-chloro-2-fluoroethylcarbonyloxy, 2-
Chloro-2,2-difluoroethylcarbonyloxy, 2,2-dichloro-2-
Fluoroethylcarbonyloxy, 2,2,2-trichloroethylcarbonyloxy
Kishi, OCOC_TwoF_Five, 2-fluoropropylcarbonyloxy, 3-fluoropropyl
Ropylcarbonyloxy, 2,2-difluoropropylcarbonyloxy, 2,
3-difluoropropylcarbonyloxy, 2-chloropropylcarbonyloxy
Si, 3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbonyl
Ruoxy, 2-bromopropylcarbonyloxy, 3-bromopropylcarboni
Ruoxy, 3,3,3-trifluoropropylcarbonyloxy, 3,3,3-
Trichloropropylcarbonyloxy, OCOCH_TwoC_TwoF_Five, OCOCF_TwoC_TwoF_Five , 1- (CH_TwoF) -2-Fluoroethylcarbonyloxy, 1- (CH_TwoCl)
-2-chloroethylcarbonyloxy, 1- (CH_TwoBr) -2-bromomethylcarbonyloxy, 4-fluorobutylcarbonyloxy, 4-chlorobutylca
Rubonyloxy, 4-bromobutylcarbonyloxy, or nonafluorobutyl
Carbonyloxy, preferably OCOCF_Three, OCOCH_TwoCl or 2,2,2-
Trifluoroethylcarbonyloxy; (C₁-C₆Alkyl) carbonyloxy: (C₁-C_FourAlkyl) cal
One of the carbonyloxy groups or, for example, n-pentyl-COO, 1-methylbutyi
-COO, 2-methylbutyl-COO, 3-methylbutyl-COO, 2,2-
Dimethylpropyl-COO, 1-ethylpropyl-COO, n-hexyl-CO
O, 1,1-dimethylpropyl-COO, 1,2-dimethylpropyl-COO,
1-methylpentyl-COO, 2-methylpentyl-COO, 3-methylpent
-COO, 4-methylpentyl-COO, 1,1-dimethylbutyl-COO,
1,2-dimethylbutyl-COO, 1,3-dimethylbutyl-COO, 2,2-
Dimethylbutyl-COO, 2,3-dimethylbutyl-COO, 3,3-dimethyl
Butyl-COO, 1-ethylbutyl-COO, 2-ethylbutyl-COO, 1,
1,2-trimethylpropyl-COO, 1,2,2-trimethylpropyl-CO
O, 1-ethyl-1-methylpropyl-COO, or 1-ethyl-2-methylpropyl
Ropyl-COO, preferably OCOCH_Three, OCOC_TwoH_Five, OCOCH_TwoC_TwoH_Five,
OCOCH (CH_Three)_Two, N-butyl-COO, OCOC (CH_Three)_Three, OCO (n
-C_FiveH₁₁) Or OCO (n-C₆H₁₃); (C₁-C₆Alkyl) thiocarbonyl: CSCH_Three, CSC_TwoH_Five, CSCH_Two C_TwoH_Five, CSCH (CH_Three)_Two, CS (n-C_FourH₉), CSCH (CH_Three) C_TwoH_Five , CSCH_TwoCH (CH_Three)_Two, CSC (CH_Three)_Three, CS (n-C_FiveH₁₁), CSC
H (CH_Three) CH_TwoC_TwoH_Five, CSCH_TwoCH (CH_Three) C_TwoH_Five, CSCH_TwoCH_TwoCH
(CH_Three)_Two, CSC (CH_Three)_TwoC_TwoH_Five, CSCH (CH_Three) CH (CH_Three)_Two, C SCH_TwoC (CH_Three)_Three, CSCH (C_TwoH_Five) C_TwoH_Five, CS (n-C₆H₁₃), CS
CH (CH_Three) (N-C_FourH₉), CSCH_TwoCH (CH_Three) CH_TwoC_TwoH_Five, CSCH _Two CH_TwoCH (CH_Three) C_TwoH_Five, CSCH_TwoCH_TwoCH_TwoCH (CH_Three)_Two, CSC (C
H_Three)_TwoCH_TwoC_TwoH_Five, CSCH (CH_Three) CH (CH_Three) C_TwoH_Five, CSCH (CH_Three ) CH_TwoCH (CH_Three)_Two, CSCH_TwoC (CH_Three)_TwoC_TwoH_Five, CSCH_TwoCH (CH_Three ) CH (CH_Three)_Two, CSCH_TwoCH_TwoC (CH_Three)_Three, CSCH (C_TwoH_Five) CH_TwoC_Two H_Five, CSCH_TwoCH (C_TwoH_Five) C_TwoH_Five, CSC (CH_Three)_TwoCH (CH_Three)_Two, CS
CH (CH_Three) C (CH_Three)_Three, CSC (CH_Three) (C_TwoH_Five) C_TwoH_FiveOr CSCH
(C_TwoH_Five) CH (CH_Three)_Two, Preferably CSCH_Three, CSC_TwoH_Five, CSCH_TwoC_Two H_Five, CSCH (CH_Three)_TwoOr CS (n-C_FourH₉); (C₁-C_FourAlkoxy) carbonyl: COOCH_Three, COOC_TwoH_Five, COOC H_TwoC_TwoH_Five, COOCH (CH_Three)_Two, N-butoxycarbonyl, COOCH (CH_Three) C_TwoH_Five, COOCH_TwoCH (CH_Three)_TwoOr COOC (CH_Three)_Three, Preferably
Is COOCH_ThreeOr COOC_TwoH_Five; (C₁-C₆Alkoxy) carbonyl: (C₁-C_FourAlkoxy) carbo
One of the nyl groups or, for example, n-pentoxy-CO, 1-methylbutoxy-C
O, 2-methylbutoxy-CO, 3-methylbutoxy-CO, 2,2-dimethyl
Propoxy-CO, 1-ethylpropoxy-CO, n-hexoxy-CO, 1,
1-dimethylpropoxy-CO, 1,2-dimethylpropoxy-CO, 1-methyl
Lupentoxy-CO, 2-methylpentoxy-CO, 3-methylpentoxy-C
O, 4-methylpentoxy-CO, 1,1-dimethylbutoxy-CO, 1,2-
Dimethylbutoxy-CO, 1,3-dimethylbutoxy-CO, 2,2-dimethyl
Butoxy-CO, 2,3-dimethylbutoxy-CO, 3,3-dimethylbutoxy
-CO, 1-ethylbutoxy-CO, 2-ethylbutoxy-CO, 1,1,2-
Trimethylpropoxy-CO, 1,2,2-trimethylpropoxy-CO, 1-
Ethyl-1-methylpropoxy-CO or 1-ethyl-2-methylpropoxy
-CO, preferably COOCH_Three, COOC_TwoH_Five, COOCH_TwoC_TwoH_Five, COOC
H (CH_Three)_Two, N-butoxy-CO, COOC (CH_Three)_Three, N-pentoxy-C
O or n-hexoxy-CO; (C₁-C_FourAlkoxy) carbonyl C₁-C_FourAlkyl: (C₁-C_FourAl
Coxy) carbonyl substituted C₁-C_FourAlkyl, for example CH_TwoCOOCH_Three , CH_TwoCOOC_TwoH_Five, CH_TwoCOOCH_TwoC_TwoH_Five, CH_TwoCOOCH (CH_Three)_Two,
n-butoxycarbonylmethyl, CH_TwoCOOCH (CH_Three) C_TwoH_Five, CH_TwoCO OCH_TwoCH (CH_Three)_Two, CH_TwoCOOC (CH_Three)_Three, 1- (COOCH_Three) Ethyl, 1- (COOC_TwoH_Five) Ethyl, 1- (COOCH)_TwoC_TwoH_Five) Ethyl, 1- [CH (CH_Three)_Two] Ethyl, 1- (n-butoxycarbonyl) ethyl, 1- [1-
Methylpropoxycarbonyl] ethyl, 1- [2-methylpropoxycarbonyl
Ethyl, 2- (COOCH_Three) Ethyl, 2- (COOC_TwoH_Five) Ethyl, 2- [COOCH (CH_Three)_Two] Ethyl, 2- (n-butoxycarbonyl) ethyl, 2-
[1-methylpropoxycarbonyl] ethyl, 2- [2-methylpropoxycal
Bonyl] ethyl, 2- [COOC (CH_Three)_ThreeEthyl, 2- (COOCH_Three) Propyl, 2- (COOC_TwoH_Five) Propyl, 2- (COOCH)_TwoC_TwoH_Five) Propyl, 2- [COOCH (CH_Three)_Two] Propyl, 2- (n-butoxycarbonyl) p
Ropyl, 2- [1-methylpropoxycarbonyl] propyl, 2- [2-methyl
Propoxycarbonyl] propyl, 2- [COOC (CH_Three)_Three] Propyl, 3-
(COOCH_Three) Propyl, 3- (COOC_TwoH_Five) Propyl, 3- (COOCH)_Two C_TwoH_Five) Propyl, 3- [COOCH (CH_Three)_Two] Propyl, 3- (n-butoki)
(Carbonyl) propyl, 3- [1-methylpropoxycarbonyl] propyl,
3- [2-methylpropoxycarbonyl] propyl, 3- [COOC (CH_Three)_Three ] Propyl, 2- (COOCH_Three) Butyl, 2- (COOC_TwoH_Five) Butyl, 2- (COOCH)_TwoC_TwoH_Five) Butyl, 2- [COOCH (CH_Three)_Two] Butyl, 2- (n-butoxycarbonyl) butyl, 2- [1-methylpropoxycarbonyl] butyl
Butyl, 2- [2-methylpropoxycarbonyl] butyl, 2- [COOC (CH _Three )_Three] Butyl, 3- (COOCH_Three) Butyl, 3- (COOC_TwoH_Five) Butyl, 3- (COOCH)_TwoC_TwoH_Five) Butyl, 3- [COOCH (CH_Three)_Two] Butyl, 3- (n-butoxycarbonyl) butyl, 3- [1-methylpropoxycarbonyl]
Butyl, 3- [2-methylpropoxycarbonyl] butyl, 3- [COOC (C
H_Three)_Three] Butyl, 4- (COOCH_Three) Butyl, 4- (COOC_TwoH_Five) Butyl, 4- (COOCH)_TwoC_TwoH_Five) Butyl, 4- [COOCH (CH_Three)_Two] Butyl, 4- (n-butoxycarbonyl) butyl, 4- [1-methylpropoxycarbonyl
] Butyl, 4- [2-methylpropoxycarbonyl] butyl or 4- [COO
C (CH_Three)_ThreeButyl, preferably CH_TwoCOOCH_Three, CH_TwoCOOC_TwoH_Five, 1- (COOCH_Three) Ethyl or 1- (COOC)_TwoH_Five) Ethyl; (C₁-C₆Alkoxy) thiocarbonyl: for example CSOCH_Three, CSOC_TwoH_Five , CSOCH_TwoC_TwoH_Five, CSOCH (CH_Three)_Two, CSO (n-C_FourH₉), CSO CH (CH_Three) C_TwoH_Five, CSOCH_TwoCH (CH_Three)_Two, CSOC (CH_Three)_Three, CS
O (n-C_FiveH₁₁), CSOCH (CH_Three) CH_TwoC_TwoH_Five, CSOCH_TwoCH (CH _Three ) C_TwoH_Five, CSOCH_TwoCH_TwoCH (CH_Three)_Two, COOCH_TwoC (CH_Three)_Three, CS
OCH (C_TwoH_Five) C_TwoH_Five, CSO (n-C₆H₁₃), CSOC (CH_Three)_TwoC_TwoH_Five , CSOCH (CH_Three) CH (CH_Three)_Two, CSOCH (CH_Three) (N-C_FourH₉),
CSOCH_TwoCH (CH_Three) CH_TwoC_TwoH_Five, CSOCH_TwoCH_TwoCH (CH_Three) C_TwoH_Five , CSOCH_TwoCH_TwoCH_TwoCH (CH_Three)_Two, CSOC (CH_Three)_TwoCH_TwoC_TwoH_Five, C
SOCH (CH_Three) CH (CH_Three) C_TwoH_Five, CSOCH (CH_Three) CH_TwoCH (CH _Three )_Two, CSOCH_TwoC (CH_Three)_TwoC_TwoH_Five, CSOCH_TwoCH (CH_Three) CH (CH_Three )_Two, CSOCH_TwoCH_TwoC (CH_Three)_Three, CSOC (C_TwoH_Five) CH_TwoC_TwoH_Five, CSO
CH_TwoCH (C_TwoH_Five) C_TwoH_Five, CSOC (CH_Three)_TwoCH (CH_Three)_Two, CSOCH (CH_Three) C (CH_Three)_Three, CSOC (CH_Three) (C_TwoH_Five) C_TwoH_FiveOr CSOCH
(C_TwoH_Five) CH (CH_Three)_Two, Preferably CSOCH_ThreeOr CSOC_TwoH_Five; (C₁-C_FourAlkylthio) carbonyl: COSCH_Three, COSC_TwoH_Five, COS CH_TwoC_TwoH_Five, COSCH (CH_Three)_Two, COSCH_TwoCH_TwoC_TwoH_Five, COSCH (CH_Three) C_TwoH_Five, COSCH_TwoCH (CH_Three)_TwoOr COSC (CH_Three)_Three, Preferred
K is COSCH_ThreeOr COSC_TwoH_Five; (C₁-C_FourAlkylthio) carbonyl C₁-C_FourAlkyl: (C₁-C_FourA
Alkylthio) carbonyl-substituted C₁-C_FourAlkyl, for example CH_TwoCOS CH_Three, CH_TwoCOSC_TwoH_Five, CH_TwoCOSCH_TwoC_TwoH_Five, CH_TwoCOSCH (CH_Three )_Two, CH_TwoCOSCH_TwoCH_TwoC_TwoH_Five, CH_TwoCOSCH (CH_Three) C_TwoH_Five, CH_Two COSCH_TwoCH (CH_Three)_Two, CH_TwoCOSC (CH_Three)_Three, 1- (COSCH_Three) Ethyl, 1- (COSC_TwoH_Five) Ethyl, 1- (COSCH_TwoC_TwoH_Five) Ethyl, 1- [COSCH (CH_Three)_Two] Ethyl, 1- (COSCH_TwoCH_TwoC_TwoH_Five)ethyl,
1- [COSCH (CH_Three) C_TwoH_Five] Ethyl, 1- [COSCH_TwoCH (CH_Three)_Two ] Ethyl, 1- [COSC (CH_Three)_Three] Ethyl, 2- (COSCH_Three) Ethyl, 2- (COSC_TwoH_Five) Ethyl, 2- (COSCH_TwoC_TwoH_Five) Ethyl, 2- [CO SCH (CH_Three)_Two] Ethyl, 2- (COSCH_TwoCH_TwoC_TwoH_Five) Ethyl, 2- [C
OSCH (CH_Three) C_TwoH_Five] Ethyl, 2- [COSCH_TwoCH (CH_Three)_Two]ethyl
, 2- [COSC (CH_Three)_Three] Ethyl, 2- (COSCH_Three) Propyl, 2- (COSC_TwoH_Five) Propyl, 2- (COSCH_TwoC_TwoH_Five) Propyl, 2- [COS CH (CH_Three)_Two] Propyl, 2- (COSCH_TwoCH_TwoC_TwoH_Five) Propyl, 2- [
COSCH (CH_Three) C_TwoH_Five] Propyl, 2- [COSCH_TwoCH (CH_Three)_Two]
Ropir, 2- [COSC (CH_Three)_Three] Propyl, 3- (COSCH_Three) Propyl, 3- (COSC_TwoH_Five) Propyl, 3- [COSCH (CH_Three)_Two] Propyl, 3
− (COSCH_TwoCH_TwoC_TwoH_Five) Propyl, 3- [COSCH (CH_Three) C_TwoH_FivePropyl, 3- [COSCH_TwoCH (CH_Three)_Two] Propyl, 3- [COSC (CH_Three)_Three] Propyl, 2- (COSCH_Three) Butyl, 2- (COSC_TwoH_Five) Butyl, 2- (COSCH_TwoC_TwoH_Five) Butyl, 2- [COSCH (CH_Three)_Two] Butyl, 2- (COSCH_TwoCH_TwoC_TwoH_Five) Butyl, 2- [COSCH (CH_Three) C_TwoH_FiveButyl, 2- [COSCH_TwoCH (CH_Three)_Two] Butyl, 2- [COSC (CH_Three) _Three ] Butyl, 3- (COSCH_Three) Butyl, 3- (COSC_TwoH_Five) Butyl, 3- (
COSCH_TwoC_TwoH_Five) Butyl, 3- [COSCH (CH_Three)_Two] Butyl, 3- (COSCH_TwoCH_TwoC_TwoH_Five) Butyl, 3- [COSCH (CH_Three) C_TwoH_Five] Butyl, 3- [COSCH_TwoCH (CH_Three)_Two] Butyl, 3- [COSC (CH_Three)_Three] Butyl, 4- (COSCH_Three) Butyl, 4- (COSC_TwoH_Five) Butyl, 4- (COS CH_TwoC_TwoH_Five) Butyl, 4- [COSCH (CH_Three)_Two] Butyl, 4- (COSC H_TwoCH_TwoC_TwoH_Five) Butyl, 4- [COSCH (CH_Three) C_TwoH_Five] Butyl, 4- [COSCH_TwoCH (CH_Three)_Two] Butyl or 4- [COSC (CH_Three)_ThreeButyl, preferably CH_TwoCOSCH_Three, CH_TwoCOSC_TwoH_Five, 1- (COSCH_Three) Etch
Or 1- (COSC_TwoH_Five) Ethyl; C₁-C₆Alkylsulfinyl: SOCH_Three, SOC_TwoH_Five, SOCH_TwoC_TwoH_Five,
SOCH (CH_Three)_Two, SO (n-C_FourH₉), SCH (CH_Three) C_TwoH_Five, SOCH_Two CH (CH_Three)_TwoOr SOC (CH_Three)_ThreeEtc. C₁-C_FourAlkylsulfinyl, or
Is, for example, SO (n-C_FiveH₁₁), 1-methylbutyl-SO, 2-methylbutyl-SO, 3-methylbutyl-SO, 2,2-dimethylpropyl-SO, 1-ethyl
Propyl-SO, n-hexyl-SO, 1,1-dimethylpropyl-SO, 1,
, 2-dimethylpropyl-SO, 1-methylpentyl-SO, 2-methylpent
Ru-SO, 3-methylpentyl-SO, 4-methylpentyl-SO, 1,1-di
Methylbutyl-SO, 1,2-dimethylbutyl-SO, 1,3-dimethylbutyl
-SO, 2,2-dimethylbutyl-SO, 2,3-dimethylbutyl-SO, 3,
3-dimethylbutyl-SO, 1-ethylbutyl-SO, 2-ethylbutyl-SO
, 1,1,2-trimethylpropyl-SO, 1,2,2-trimethylpropyl-
SO, 1-ethyl-1-methylpropyl-SO or 1-ethyl-2-methylpro
Pill-SO, preferably SOCH_Three, SOC_TwoH_Five, SOCH_TwoC_TwoH_Five, SOCH (
CH_Three)_Two, SO (n-C_FourH₉), SOC (CH_Three)_Three, SO (n-C_FiveH₁₁) Or SO (n-C₆H₁₃); C₁~ C_FourAlkylsulfinyl C₁~ C_FourAlkyl: C as described above₁~ C_FourAlkyls
C substituted with rufinyl₁~ C_FourAlkyl, for example CH_TwoSOCH_Three, CH_TwoS OC_TwoH_Five, N-propylsulfinylmethyl, CH_TwoSOCH (CH_Three)_Two, N-butylsulfinylmethyl, (1-methylpropylsulfinyl) methyl, (2
-Methylpropylsulfinyl) methyl, (1,1-dimethylethylsulfinyl)
Le) methyl, 2-methylsulfinylethyl, 2-ethylsulfinylethyl,
2- (n-propylsulfinyl) ethyl, 2- (1-methylethylsulfinyl)
E) ethyl, 2- (n-butylsulfinyl) ethyl, 2- (1-methylprop
Rusulfinyl) ethyl, 2- (2-methylpropylsulfinyl) ethyl, 2
-(1,1-dimethylethylsulfinyl) ethyl, 2- (SOCH_Three) Propyl, 3- (SOCH_Three) Propyl, 2- (SOC_TwoH_Five) Propyl, 3- (SOC_Two H_Five) Propyl, 3- (propylsulfinyl) propyl, 3- (butylsulfinyl) propyl, 4- (SOCH_Three) Butyl, 4- (SOC_TwoH_Five) Butyl, 4- (n-propylsulfinyl) butyl or 4- (n-butylsulfinyl) butyl
Chill, especially 2- (SOCH_Three) Ethyl; C₁~ C_FourHaloalkylsulfinyl C₁~ C_FourAlkyl: C as described above₁~ C_FourHaloa
C substituted with alkylsulfinyl₁~ C_FourAlkyl, for example 2- (2,2,2-
Trifluoroethylsulfinyl) ethyl; C₁~ C_FourAlkylsulfonyl: SO_TwoCH_Three, SO_TwoC_TwoH_Five, SO_TwoCH_TwoC_TwoH_Five , SO_TwoCH (CH_Three)_Two, N-butylsulfonyl, SO_TwoCH (CH_Three) C_TwoH_Five, SO_TwoCH_TwoCH (CH_Three)_TwoOr SO_TwoC (CH_Three)_Three, Preferably SO_TwoCH_ThreeOr SO_TwoC_TwoH_FiveC₁~ C_FourHaloalkylsulfonyl: partially or completely fluorine, chlorine, bromine and
And / or the above-mentioned C substituted by iodine₁~ C_FourAlkylsulfonyl, such as SO_Two -CH_TwoF, SO_Two-CHF_Two, SO_Two-CF_Three, SO_Two-CH_TwoCl, SO_Two-CH (
Cl)_Two, SO_Two-C (Cl)_Three, Chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethyl
Tylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl,
2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2
2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl
2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2
-Fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, SO _Two -C_TwoF_Five, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl
Fonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2,
3-dichloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromo
Propylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3
3-trichloropropylsulfonyl, SO_Two-CH_Two-C_TwoF_Five, SO_Two-CF_Two-C _Two F_Five, 1- (fluoromethyl) -2-fluoroethylsulfonyl, 1- (chloro
Methyl) -2-chloroethylsulfonyl, 1- (bromomethyl) -2-bromoe
Tylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl
, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl, preferably S
O_Two-CH_TwoCl, SO_Two-CF_ThreeOr 2,2,2-trifluoroethylsulfonyl
C₁~ C₆Alkylsulfonyl: C described above₁~ C_FourAn alkylsulfonyl group, or
For example, SO_Two− (N−C_FiveH₁₁), 1-methylbutyl-SO_Two, 2-methylbutyl-SO_Two, 3-methylbutyl-SO_Two, 2,2-dimethylpropyl-SO_Two1-ethylpropyl-SO_Two, N-hexyl-SO_Two, 1,1-dimethylpropyl-
SO_Two, 1,2-dimethylpropyl-SO_Two, 1-methylpentyl-SO_Two, 2-methylpentyl-SO_Two, 3-methylpentyl-SO_Two, 4-methylpentyl-S
O_Two, 1,1-dimethylbutyl-SO_Two, 1,2-dimethylbutyl-SO_Two, 1,3-dimethylbutyl-SO_Two, 2,2-dimethylbutyl-SO_Two, 2,3-Dimethi
Rubutyl-SO_Two, 3,3-dimethylbutyl-SO_Two, 1-ethylbutyl-SO_Two , 2-ethylbutyl-SO_Two, 1,1,2-trimethylpropyl SO_Two, 1, 2,
2-trimethylpropyl-SO_Two, 1-ethyl-1-methylpropyl-SO_TwoOr
1-ethyl-2-methylpropyl-SO_Two, Preferably SO_TwoCH_Three, SO_TwoC_TwoH_Five , SO_TwoCH (CH_Three)_Two, SO_Two(N-C_FourH₉), SO_TwoC (CH_Three)_Three, SO_Two− (
n-C_FiveH₁₁) Or SO_Two(N-C₆H₁₃); C₁~ C_FourAlkylsulfonyl C₁~ C_FourAlkyl: C as described above₁~ C_FourAlkylsul
C substituted with honyl₁~ C_FourAlkyl, for example CH_TwoSO_TwoCH_Three, CH_TwoSO_Two C_TwoH_Five, CH_TwoSO_Two-CH_Two-C_TwoH_Five, CH_TwoSO_Two-CH (CH_Three)_Two, CH_TwoSO _Two -CH_TwoCH_Two-C_TwoH_Five, (1-methylpropylsulfonyl) methyl, (2-methylpropylsulfonyl) methyl, CH_TwoSO_Two-C (CH_Three)_Three, CH (CH_Three) SO_Two-CH_Three, CH (CH_Three) SO_Two-C_TwoH_Five, CH_TwoCH_TwoSO_Two-CH_Three, CH_Two CH_TwoSO_Two-C_TwoH_Five, CH_TwoCH_TwoSO_Two-CH_Two-C_TwoH_Five, CH_TwoCH_TwoSO_Two-CH (CH_Three)_Two, CH_TwoCH_TwoSO_Two-CH_TwoCH_Two-C_TwoH_Five, 2- (1-methylpropylsulfonyl) ethyl, 2- (2-methylpropylsulfonyl) ethyl, CH _Two CH_TwoSO_Two-C (CH_Three)_Three, 2- (SO_TwoCH_Three) Propyl, 2- (SO_TwoC_TwoH_Five ) Propyl, 2- (SO_Two-CH_Two-C_TwoH_Five) Propyl, 2- [SO_Two-CH (CH_Three)_Two] Propyl, 2- (SO_Two-CH_TwoCH_Two-C_TwoH_Five) Propyl, 2- (1-methylpropylsulfonyl) propyl, 2- (2-methylpropylsulfonyl)
Propyl, 2- [SO_Two-C (CH_Three)_ThreePropyl, 3- (SO_TwoCH_Three) Propyl, 3- (SO_TwoC_TwoH_Five) Propyl, 3- (SO_Two-CH_Two-C_TwoH_Five) Propyl, 3- [SO_Two-CH (CH_Three)_TwoPropyl, 3- (SO_Two-CH_TwoCH_Two-C_TwoH_Five)
Propyl, 3- (1-methylpropylsulfonyl) propyl, 3- (2-methyl
Propylsulfonyl) propyl, 3- [SO_Two-C (CH_Three)_ThreePropyl, 2- (SO_TwoCH_Three) Butyl, 2- (SO_TwoC_TwoH_Five) Butyl, 2- (SO_Two-CH_Two-C_Two H_Five) Butyl, 2- [SO_Two-CH (CH_Three)_TwoButyl, 2- (SO_Two-CH_TwoCH _Two -C_TwoH_Five) Butyl, 2- (1-methylpropylsulfonyl) butyl, 2- (2-methylpropylsulfonyl) butyl, 2- [SO_Two-C (CH_Three)_ThreeButyl, 3- (SO_TwoCH_Three) Butyl, 3- (SO_TwoC_TwoH_Five) Butyl, 3- (SO_Two-CH_Two -C_TwoH_Five) Butyl, 3- [SO_Two-CH (CH_Three)_TwoButyl, 3- (SO_Two-CH _Two CH_Two-C_TwoH_Five) Butyl, 3- (1-methylpropylsulfonyl) butyl, 3-
(2-methylpropylsulfonyl) butyl, 3- [SO_Two-C (CH_Three)_Three] Butyl, 4- (SO_TwoCH_Three) Butyl, 4- (SO_TwoC_TwoH_Five) Butyl, 4- (SO_Two-C
H_Two-C_TwoH_Five) Butyl, 4- [SO_Two-CH (CH_Three)_TwoButyl, 4- (SO_Two− CH_TwoCH_Two-C_TwoH_Five) Butyl, 4- (1-methylpropylsulfonyl) butyl,
4- (2-methylpropylsulfonyl) butyl or 4- [SO_Two-C (CH_Three)_Three Butyl, especially CH_TwoCH_TwoSO_Two-CH_ThreeOr CH_TwoCH_TwoSO_Two-C_TwoH_FiveC₁~ C_FourHaloalkylsulfonyl C₁~ C_FourAlkyl: C as described above₁~ C_FourHaloal
C substituted with kilsulfonyl₁~ C_FourAlkyl, for example 2- (2,2,2-tri
Fluoroethylsulfonyl) ethyl; C₁~ C_FourAlkylamino-C₁~ C_FourAlkyl: C₁~ C_FourAlkylamino, for example
If N_ThreeC-NH-, H_FiveC_Two-NH-, n-propyl-NH-, 1-methylethyl-NH-, n-butyl-NH-, 1-methylpropyl-NH-, 2-methylpro
Pill-NH- and 1,1-dimethylethyl-NH-, preferably N_ThreeC-NH- or H_FiveC_TwoC substituted with -NH-₁~ C_FourAlkyl, for example CH_TwoCH_TwoNHCH _Three , CH_TwoCH_TwoN (CH_Three)_Two, CH_TwoCH_TwoNHC_TwoH_FiveOr CH_TwoCH_TwoN (C_TwoH_Five )_Two; (C₁~ C_FourAlkylamino) carbonyl: CO-NH-CH_Three-, CO-NH-C_TwoH_Five-, N-propylamino, CO-NH-CH (CH_Three)_Two, CO-NH-
CH_TwoCH_Two-C_TwoH_Five, CO-NH-CH (CH_Three) -C_TwoH_Five, CO-NH-CH_Two CH (CH_Three)_TwoOr CO-NH-C (CH_Three)_Three, Preferably CO-NH-CH_Three -Or CO-NH-C_TwoH_Five-; (C₁~ C₆Alkylamino) carbonyl: the above-mentioned (C1-C4 alkylamino)
) One of the carbonyl groups or, for example, CO-NH- (nC_FiveH₁₁), 1-methylbutyl-NHCO-, 2-methylbutyl-NHCO-, 3-methylbutyl-
NHCO-, 2,2-dimethylpropyl-NHCO-, 1-ethylpropyl-
NHCO-, CO-NH- (n-C₆H₁₃), 1,1-dimethylpropyl-NHCO-, 1,2-dimethylpropyl-NHCO-, 1-methylpentyl-NHC
O-, 2-methylpentyl-NHCO-, 3-methylpentyl-NHCO-, 4
-Methylpentyl-NHCO-, 1,1-dimethylbutyl-NHCO-, 1,2
-Dimethylbutyl-NHCO-, 1,3-dimethylbutyl-NHCO-, 2,2
-Dimethylbutyl-NHCO-, 2,3-dimethylbutyl-NHCO-, 3,3
-Dimethylbutyl-NHCO-, 1-ethylbutyl-NHCO-, 2-ethylbutyl
Cyl-NHCO-, 1,1,2-trimethylpropyl-NHCO-, 1,2,2
-Trimethylpropyl-NHCO-, 1-ethyl-1-methylpropyl-NHC
O- or 1-ethyl-2-methylpropyl-NHCO-, preferably CO-NH
-CH_Three, CO-NH-C_TwoH_Five, CO-NH-CH_Two-C_TwoH_Five, CO-NH-CH
(CH_Three)_Two, CO-NH- (n-C_FourH₉), CO-NH-C (CH_Three)_Three, CO-
NH- (n-C_FiveH₁₁) Or CO-NH- (n-C₆H₁₃); (C₁~ C_FourAlkylamino) carbonyl C₁~ C_FourAlkyl: (C₁~ C_Four Alkylamino) carbonyl, preferably CO-NH-CH_ThreeOr CO-NH-C_TwoH_FiveC substituted with₁~ C_FourAlkyl, for example CH_Two-CO-NH-CH_Three, CH _Two -CO-NH-C_TwoH_Five, CH_Two-CO-NH-CH_Two-C_TwoH_Five, CH_Two-CO-N
H-CH (CH_Three)_Two, CH_Two-CO-NH-CH_TwoCH_Two-C_TwoH_Five, CH_Two-CO-
NH-CH (CH_Three) -C_TwoH_Five, CH_Two-CO-NH-CH_Two-CH (CH_Three)_Two, CH_Two-CO-NH-C (CH_Three)_Three, CH (CH_Three) CO-NH-CH_Three, CH (CH_Three) -CO-NH-C_TwoH_Five, 2- (CO-NH-CH_Three) Ethyl, 2- (CO
-NH-C_TwoH_Five) Ethyl, 2- (CO-NH-CH)_Two-C_TwoH_Five) Ethyl, 2- [CH_Two-CO-NH-CH (CH_Three)_Two] Ethyl, 2- (CO-NH-CH_TwoCH_Two -C_TwoH_Five) Ethyl, 2- [CO-NH-CH (CH_Three) -C_TwoH_Five] Ethyl, 2- [CO-NH-CH_Two-CH (CH_Three)_Two] Ethyl, 2- [CO-NH-C (CH_Three )_Three] Ethyl, 2- (CO-NH-CH_Three) Propyl, 2- (CO-NH-C)_TwoH_Five ) Propyl, 2- (CO-NH-CH)_Two-C_TwoH_Five) Propyl, 2- [CH_Two-CO
-NH-CH (CH_Three)_Two] Propyl, 2- (CO-NH-CH_TwoCH_Two-C_TwoH_Five)
Propyl, 2- [CO-NH-CH (CH_Three) -C_TwoH_Five] Propyl, 2- [CO-NH-CH_Two-CH (CH_Three)_Two] Propyl, 2- [CO-NH-C (CH_Three)_Three ] Propyl, 3- (CO-NH-CH_Three) Propyl, 3- (CO-NH-C)_TwoH_Five ) Propyl, 3- (CO-NH-CH)_Two-C_TwoH_Five) Propyl, 3- [CH_Two-CO
-NH-CH (CH_Three)_Two] Propyl, 3- (CO-NH-CH_TwoCH_Two-C_TwoH_Five)
Propyl, 3- [CO-NH-CH (CH_Three) -C_TwoH_Five] Propyl, 3- [CO-NH-CH_Two-CH (CH_Three)_Two] Propyl, 3- [CO-NH-C (CH_Three)_Three ] Propyl, 2- (CO-NH-CH_Three) Butyl, 2- (CO-NH-C)_TwoH_Five) Butyl, 2- (CO-NH-CH)_Two-C_TwoH_Five) Butyl, 2- [CH_Two-CO-NH
-CH (CH_Three)_Two] Butyl, 2- (CO-NH-CH_TwoCH_Two-C_TwoH_Five) Butyl,
2- [CO-NH-CH (CH_Three) -C_TwoH_Five] Butyl, 2- [CO-NH-CH_Two -CH (CH_Three)_Two] Butyl, 2- [CO-NH-C (CH_Three)_ThreeButyl, 3- (
CO-NH-CH_Three) Butyl, 3- (CO-NH-C)_TwoH_Five) Butyl, 3- (CO-NH-CH)_Two-C_TwoH_Five) Butyl, 3- [CH_Two-CO-NH-CH (CH_Three)_Two]
Butyl, 3- (CO-NH-CH_TwoCH_Two-C_TwoH_Five) Butyl, 3- [CO-NH-
CH (CH_Three) -C_TwoH_Five] Butyl, 3- [CO-NH-CH_Two-CH (CH_Three)_Two]
Butyl, 3- [CO-NH-C (CH_Three)_Three] Butyl, 4- (CO-NH-CH_Three ) Butyl, 4- (CO-NH-C_TwoH_Five) Butyl, 4- (CO-NH-CH)_Two-C_Two H_Five) Butyl, 4- [CH_Two-CO-NH-CH (CH_Three)_TwoButyl, 4- (CO
-NH-CH_TwoCH_Two-C_TwoH_Five) Butyl, 4- [CO-NH-CH (CH_Three) -C_Two H_Five] Butyl, 4- [CO-NH-CH_Two-CH (CH_Three)_Two] Butyl or 4- [C
O-NH-C (CH_Three)_ThreeButyl, preferably CH_Two-CO-NH-CH_Three, CH _Two -CO-NH-C_TwoH_Five, CH (CH_Three) CO-NH-CH_ThreeOr CH (CH_Three)-
CO-NH-C_TwoH_FiveJ (C₁~ C_FourAlkyl) amino: N (CH_Three)_Two, N (C_TwoH_Five)_Two, N, N-dipropylamino, N, N-di (1-methylethyl) amino, N, N-dibutylamine
Mino, N, N-di (1-methylpropyl) amino, N, N-di (2-methylpro
Pill) amino, N, N-di (1,1-dimethylethyl) amino, N-ethyl-N
-Methylamino, N-methyl-N-propylamino, N-methyl-N- (1-
Tylethyl) amino, N-butyl-N-methylamino, N-methyl-N- (1-
Methylpropyl) amino, N-methyl-N- (2-methylpropyl) amino, N
-(1,1-dimethylethyl) -N-methylamino, N-ethyl-N-propyl
Amino, N-ethyl-N- (1-methylethyl) amino, N-butyl-N-ethyl
Amino, N-ethyl-N- (1-methylpropyl) amino, N-ethyl-N-
(2-methylpropyl) amino, N-ethyl-N- (1,1-dimethylethyl)
Amino, N- (1-methylethyl) -N-propylamino, N-butyl-N-propyl
Ropylamino, N- (1-methylpropyl) -N-propylamino, N- (2-
Methylpropyl) -N-propylamino, N- (1,1-dimethylethyl) -N
-Propylamino, N-butyl-N- (1-methylethyl) amino, N- (1-
Methylethyl) -N- (1-methylpropyl) amino, N- (1-methylethyl
) -N- (2-methylpropyl) amino, N- (1,1-dimethylethyl) -N
-(1-methylethyl) amino, N-butyl-N- (1-methylpropyl) amido
, N-butyl-N- (2-methylpropyl) amino, N-butyl-N- (1,
1-dimethylethyl) amino, N- (1-methylpropyl) -N- (2-methyl
Propyl) amino, N- (1,1-dimethylethyl) -N- (1-methylpropyl
Ru) amino or N- (1,1-dimethylethyl) -N- (2-methylpropyl)
Amino, preferably N (CH_Three)_TwoOr N (C_TwoH_Five)_TwoJ (C₁~ C_FourAlkyl) amino C₁~ C_FourAlkyl: di (C₁~ C_FourArchi
C) amino-substituted C₁~ C_FourAlkyl, for example CH_TwoN (CH_Three)_Two, CH_TwoN
(C_TwoH_Five)_Two, N, N-dipropylaminomethyl, N, N-di [CH (CH_Three)_Two ] Aminomethyl, N, N-dibutylaminomethyl, N, N-di (1-methylpro
Pill) aminomethyl, N, N-di (2-methylpropyl) aminomethyl, N, N
-Di [C (CH_Three)_Three] Aminomethyl, N-ethyl-N-methylaminomethyl, N
-Methyl-N-propylaminomethyl, N-methyl-N- [CH (CH_Three)_Two]
Minomethyl, N-butyl-N-methylaminomethyl, N-methyl-N- (1-
Tylpropyl) aminomethyl, N-methyl-N- (2-methylpropyl) amino
Methyl, N- [C (CH_Three)_Three] -N-methylaminomethyl, N-ethyl-N-propyl
Ropylaminomethyl, N-ethyl-N- [CH (CH_Three)_Two] Aminomethyl, N-
Butyl-N-ethylaminomethyl, N-ethyl-N- (1-methylpropyl)
Minomethyl, N-ethyl-N- (2-methylpropyl) aminomethyl, N-ethyl
Ru-N- [C (CH_Three)_Three] Aminomethyl, N- [CH (CH_Three)_Two] -N-propyl
Aminomethyl, N-butyl-N-propylaminomethyl, N- (1-methyl
Ropyl) -N-propylaminomethyl, N- (2-methylpropyl) -N-pro
Pyraminomethyl, N- [C (CH_Three)_Three] -N-propylaminomethyl, N-butyl
Tyl-N- (1-methylethyl) aminomethyl, N- [CH (CH_Three)_Two] -N-
(1-methylpropyl) aminomethyl, N- [CH (CH_Three)_Two] -N- (2-me
Tylpropyl) aminomethyl, N- [C (CH_Three)_Three] -N- [CH (CH_Three)_Two]
Aminomethyl, N-butyl-N- (1-methylpropyl) aminomethyl, N-butyl
Tyl-N- (2-methylpropyl) aminomethyl, N-butyl-N- [C (CH _Three )_Three] Aminomethyl, N- (1-methylpropyl) -N- (2-methylpropyl
) Aminomethyl, N- [C (CH_Three)_Three] -N- (1-methylpropyl) aminometh
Chill, N- [C (CH_Three)_Three] -N- (2-methylpropyl) aminomethyl, N,
N-dimethylaminoethyl, N, N-diethylaminoethyl, N, N-di (n-
Propyl) aminoethyl, N, N-di [CH (CH_Three)_Two] Aminoethyl, N, N
-Dibutylaminoethyl, N, N-di (1-methylpropyl) aminoethyl, N
, N-di (2-methylpropyl) aminoethyl, N, N-di [C (CH_Three)_Three]
Minoethyl, N-ethyl-N-methylaminoethyl, N-methyl-N-propyl
Aminoethyl, N-methyl-N- [CH (CH_Three)_Two] Aminoethyl, N-butyl
-N-methylaminoethyl, N-methyl-N- (1-methylpropyl) amino
Chill, N-methyl-N- (2-methylpropyl) aminoethyl, N- [C (CH _Three )_Three] -N-methylaminoethyl, N-ethyl-N-propylaminoethyl, N
-Ethyl-N- [CH (CH_Three)_Two] Aminoethyl, N-butyl-N-ethylamido
Noethyl, N-ethyl-N- (1-methylpropyl) aminoethyl, N-ethyl
-N- (2-methylpropyl) aminoethyl, N-ethyl-N- [C (CH_{3) 3} ] Aminoethyl, N- [CH (CH_Three)_Two] -N-propylaminoethyl, N-butyl
Tyl-N-propylaminoethyl, N- (1-methylpropyl) -N-propyl
Aminoethyl, N- (2-methylpropyl) -N-propylaminoethyl, N-
[C (CH_Three)_Three] -N-propylaminoethyl, N-butyl-N- [CH (CH _Three )_Two] Aminoethyl, N- [CH (CH_Three)_Two] -N- (1-methylpropyl) a
Minoethyl, N- [CH (CH_Three)_Two] -N- (2-methylpropyl) aminoethyl
, N- [C (CH_Three)_Three] -N- [CH (CH_Three)_Two] Aminoethyl, N-butyl
-N- (1-methylpropyl) aminoethyl, N-butyl-N- (2-methyl
Ropyl) aminoethyl, N-butyl-N- [C (CH_Three)_Three] Aminoethyl, N-
(1-methylpropyl) -N- (2-methylpropyl) aminoethyl, N- [C
(CH_Three)_Three] -N- (1-methylpropyl) aminoethyl or N- [C (CH_Three )_Three] -N- (2-methylpropyl) aminoethyl, especially N, N-dimethylaminoethyl or N, N-diethylaminoethyl; di (C₁~ C_FourAlkyl) aminocarbonyl: CON (CH_Three)_Two, CON (C_Two H_Five)_Two, CON (CH_TwoC_TwoH_Five)_Two, CON [CH (CH_Three)_Two]_Two, N, N-dibutylaminocarbonyl, CON [CH (CH_Three) C_TwoH_Five]_Two, CON [CH_TwoCH (CH_Three)_Two]_Two, CON [C (CH_Three)_Three]_Two, N-ethyl-N-methylaminocar
Bonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N- [CH
(CH_Three)_Two] Aminocarbonyl, N-butyl-N-methylaminocarbonyl, N
-Methyl-N- (1-methylpropyl) aminocarbonyl, N-methyl-N- (
2-methylpropyl) aminocarbonyl, N- [C (CH_Three)_Three] -N-methyla
Minocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N
-[CH (CH_Three)_Two] Aminocarbonyl, N-butyl-N-ethylaminocarbo
Nyl, N-ethyl-N- (1-methylpropyl) aminocarbonyl, N-ethyl
-N- (2-methylpropyl) aminocarbonyl, N-ethyl-N- [C (CH _Three )_Three] Aminocarbonyl, N- [CH (CH_Three)_Two] -N-propylaminocarbo
Nyl, N-butyl-N-propylaminocarbonyl, N- (1-methylpropyl
) -N-propylaminocarbonyl, N- (2-methylpropyl) -N-propyl
Aminocarbonyl, N- [C (CH_Three)_Three] -N-propylaminocarbonyl,
N-butyl-N- [CH (CH_Three)_Two] Aminocarbonyl, N- [CH (CH_Three)_Two ] -N- (1-methylpropyl) aminocarbonyl, N- [CH (CH_Three)_Two]-
N- (2-methylpropyl) aminocarbonyl, N- [C (CH_Three)_Three] -N- [
CH (CH_Three)_Two] Aminocarbonyl, N-butyl-N- (1-methylpropyl)
Aminocarbonyl, N-butyl-N- (2-methylpropyl) aminocarbonyl
, N-butyl-N- [C (CH_Three)_Three] Aminocarbonyl, N- (1-methylpro
Pill) -N- (2-methylpropyl) aminocarbonyl, N- [C (CH_Three)_Three]
-N- (1-methylpropyl) aminocarbonyl or N- [C (CH_Three)_Three] -N
-(2-methylpropyl) aminocarbonyl, preferably CON (CH_Three)_TwoOr
CON (C_TwoH_Five)_TwoJ (C₁~ C₆Alkyl) aminocarbonyl: di (C₁~ C_FourAlkyl)
One of the minocarbonyl groups or, for example, N (CH_Three)-(N-C_FiveH₁₁), N
(C_TwoH_Five)-(N-C_FiveH₁₁), N (CH_Two-C_TwoH_Five)-(N-C_FiveH₁₁), N (n-C_FourH₉)-(N-C_FiveH₁₁), N (n-C_FiveH₁₁)-(N-C_FiveH₁₁), N (n-C₆H₁₃)-(N-C_FiveH₁₁), N (CH_Three)-(N-C₆H₁₃), N (C_TwoH_Five )-(N-C₆H₁₃), N (CH_Two-C_TwoH_Five)-(N-C₆H₁₃), N (n-C_FourH ₉ )-(N-C₆H₁₃), N (n-C_FiveH₁₁)-(N-C₆H₁₃), N (n-C₆H_{1 Three} )_TwoJ (C₁~ C_FourAlkyl) aminocarbonyl C₁~ C_FourAlkyl: di (C₁ ~ C_FourAlkyl) aminocarbonyl group, preferably CON (CH_Three)_TwoOr CON (C_TwoH_Five)_TwoC substituted with₁~ C_FourAlkyl, for example CH_TwoCON (CH_Three)_Two, C
H_TwoCON (C_TwoH_Five)_Two, CH (CH_Three) CON (CH_Three)_TwoOr CH (CH_Three) CO
N (C_TwoH_Five)_Two, Preferably CH_TwoCON (CH_Three)_TwoOr CH (CH_Three) CON (CH_Three)_TwoJ (C₁~ C_FourAlkyl) phosphonyl C₁~ C_FourAlkyl: The following di (C₁~ C_FourA
Alkyl) phosphonyl such as -PO (OCH_Three)_Two, -PO (OC_TwoH_Five)_Two, N, N-dipropylphosphonyl, N, N-di (1-methylethyl) phosphonyl,
N-dibutylphosphonyl, N, N-di (1-methylpropyl) phosphonyl,
N-di (2-methylpropyl) phosphonyl, N, N-di (1,1-dimethylethyl)
G) phosphonyl, N-ethyl-N-methylphosphonyl, N-methyl-N-propyl
Ruphosphonyl, N-methyl-N- (1-methylethyl) phosphonyl, N-butyl
-N-methylphosphonyl, N-methyl-N- (1-methylpropyl) phosphonyl
, N-methyl-N- (2-methylpropyl) phosphonyl, N- (1,1-dimethyl)
Ruethyl) -N-methylphosphonyl, N-ethyl-N-propylphosphonyl, N
-Ethyl-N- (1-methylethyl) phosphonyl, N-butyl-N-ethylphos
Phonyl, N-ethyl-N- (1-methylpropyl) phosphonyl, N-ethyl-N
-(2-methylpropyl) phosphonyl, N-ethyl-N- (1,1, -dimethyl
Ethyl) phosphonyl, N- (1-methylethyl) -N-propylphosphonyl, N
-Butyl-N-propylphosphonyl, N- (1-methylpropyl) -N-propyl
Ruphosphonyl, N- (2-methylpropyl) -N-propylphosphonyl, N- (
1,1-dimethylethyl) -N-propylphosphonyl, N-butyl-N- (1-
Methylethyl) phosphonyl, N- (1-methylethyl) -N- (1-methylpro
Pill) phosphonyl, N- (1-methylethyl) -N- (2-methylpropyl)
Suphonyl, N- (1,1-dimethylethyl) -N- (1-methylethyl) phospho
Nyl, N-butyl-N- (1-methylpropyl) phosphonyl, N-butyl-N-
(2-methylpropyl) phosphonyl, N-butyl-N- (1,1-dimethylethyl)
F) phosphonyl, N- (1-methylpropyl) -N- (2-methylpropyl)
Suphonyl, N- (1,1-dimethylethyl) -N- (1-methylpropyl) phos
Honyl or N- (1,1-dimethylethyl) -N- (2-methylpropyl) phos
Honyl, preferably -PO (OCH_Three)_TwoOr -PO (OC_TwoH_Five)_TwoC replaced with₁~ C_FourAlkyl, for example CH_TwoPO (OCH_Three)_Two, CH_TwoPO (OC_TwoH_Five)_Two, CH (CH_Three) PO (OCH_Three)_TwoOr CH (CH_Three) PO (OC_TwoH_Five)_TwoC_Three~ C₆Alkenyl: prop-1-en-1-yl, allyl, 1-methylether
Nil, 1-buten-1-yl, 1-buten-2-yl, 1-buten-3-yl,
2-buten-1-yl, 1-methylprop-1-en-1-yl, 2-methyl
Lopa-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methyl
Leprop-2-en-1-yl, n-penten-1-yl, n-penten-2-yl
Yl, n-penten-3-yl, n-penten-4-yl, 1-methylbuta-1
-En-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1
-En-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2
-En-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3
-En-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3
-En-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-di
Methylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-
Yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-ene-
1-yl, n-hex-1-en-1-yl, n-hex-2-en-1-yl
N-hex-3-en-1-yl, n-hex-4-en-1-yl, n-he
Oxa-5-en-1-yl, 1-methylpenta-1-en-1-yl, 2-methyl
Rupenta-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-
Methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl,
2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-i
4-Methylpent-2-en-1-yl, 1-methylpent-3-en-1
-Yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-ene
-1-yl, 4-methylpenta-3-en-1-yl, 1-methylpenta-4-
En-1-yl, 2-methylpenta-4-en-1-yl, 3-methylpenta-
4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethyl
Rubut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1
, 2-Dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-ene-
1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbuta
-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-
Dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-i
2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-yl
En-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethyl
Rubut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1
-Ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1
-Ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2
-Ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1
, 1,2-Trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop
Loper-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-i
Or 1-ethyl-2-methylprop-2-en-1-yl; C_Three~ C₆Haloalkenyl: partially or completely fluorine, chlorine, bromine and / or
The above-mentioned C substituted by iodine_Three~ C₆Alkenyl, for example 2-chloroallyl, 3
-Chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3
3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl
, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,
3,3-tribromoallyl or 2,3-dibromobut-2-enyl, especially 2-
Loroallyl, 3-chloroallyl or 3,3-dichloroallyl; cyano C_Three~ C₆Alkenyl: for example, 2-cyanoallyl, 3-cyanoallyl,
4-cyanobuta-2-enyl, 4-cyanobuta-3-enyl or 5-cyanopen
Ter-4-enyl; C_Three~ C₆Alkynyl: prop-1-yn-1-yl, prop-2-yn-1-yl
Yl, n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-butyl
Ta-1-yn-4-yl, n-but-2-yn-1-yl, n-penta-1-i
1-yl, n-penta-1-yn-3-yl, n-penta-1-yn-4-yl
Yl, n-penta-1-yn-5-yl, n-penta-2-yn-1-yl, n
-Pent-2-yn-4-yl, n-penta-2-yn-5-yl, 3-methyl
But-1-yn-3-yl, 3-methylbut-1-yn-4-yl, n-hexa
-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-y
N-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6
Yl, n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n
-Hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hexa
-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methylpenta-
1-in-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpen
Ta-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methyl
Penta-1-yn-1-yl, 4-methylpent-2-yn-4-yl or 4-
Methylpenta-2-yn-5-yl, preferably prop-2-yn-1-yl; C_Three~ C₆Haloalkynyl: partially or completely fluorine, chlorine, bromine and / or
The above-mentioned C substituted by iodine_Three~ C₆Alkynyl, for example, 1,1-difluorop
Loper-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chloro
Lobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl,
5-fluoropent-3-yn-1-yl or 6-fluorohex-4-yn-
1-yl; cyano C_Three~ C₆Alkynyl: for example, 3-cyanopropargyl, 4-cyanobu
Ta-2-yn-1-yl, 5-cyanopenta-3-yn-1-yl and 6-cia
Nohex-4-yn-1-yl; C_Three~ C_FourAlkenyloxy C₁~ C_FourAlkyl: the following C_Three~ C_FourAlkenyloxy
For example, allyloxy, but-1-en-3-yloxy, but-1-en-
4-yloxy, but-2-en-1-yloxy, 1-methylprop-2-e
C substituted with niloxy or 2-methylprop-2-enyloxy₁~ C_FourAl
Kill, for example, allyloxymethyl, 2-allyloxyethyl or but-1-ene
-4-yloxymethyl, especially 2-allyloxyethyl; C_Three~ C_FourAlkynyloxy C₁~ C_FourAlkyl: the following C_Three~ C_FourAlkynyloxy
For example, propargyloxy, but-1-yn-3-yloxy, but-1-
In-4-yloxy, but-2-yn-1-yloxy, 1-methylprop
2-ynyloxy or 2-methylprop-2-ynyloxy, preferably propa
C substituted with lugyloxy₁~ C_FourAlkyl, ie, for example, propargyloxy
Methyl or 2-propargyloxyethyl, especially 2-propargyloxyethyl
C_Three~ C_FourAlkenylthio C₁~ C_FourAlkyl: the following C_Three~ C_FourAlkenylthio,
For example, allylthio, but-1-en-3-ylthio, but-1-en-4-yl
Thio, but-2-en-1-ylthio, 1-methylprop-2-enylthio or
C substituted with 2-methylprop-2-enylthio₁~ C_FourAlkyl, ie
Allylthiomethyl, 2-allylthioethyl or but-1-en-4-ylthio
Methyl, especially 2- (allylthio) ethyl; C_Three~ C_FourAlkynylthio C₁~ C_FourAlkyl: the following C_Three~ C_FourAlkynylthio,
For example, propargylthio, but-1-yn-3-ylthio, but-1-yn-4
-Ylthio, but-2-yn-1-ylthio, 1-methylprop-2-ynylthio
O or substituted with 2-methylprop-2-ynylthio, preferably propargylthio
Done C₁~ C_FourAlkyl, i.e., for example, propargylthiomethyl or 2-propa
Lugylthioethyl, especially 2- (propargylthio) ethyl; C_Three~ C_FourAlkenylsulfinyl C₁~ C_FourAlkyl: the following C_Three~ C_FourAlkene
Rusulfinyl, for example allylsulfinyl, but-1-en-3-ylsulf
Inyl, but-1-en-4-ylsulfinyl, but-2-en-1-yls
Rufinyl, 1-methylprop-2-enylsulfinyl or 2-methylpropa
C substituted with -2-enylsulfinyl₁~ C_FourAlkyl, ie, for example, allyl
Sulfinylmethyl, 2-allylsulfinylethyl or but-1-en-4-
Ylsulfinylmethyl, especially 2- (allylsulfinyl) ethyl; C_Three~ C_FourAlkynyl sulfinyl C₁~ C_FourAlkyl: the following C_Three~ C_FourAlkini
Rusulfinyl, for example propargylsulfinyl, but-1-yn-3-yl
Sulfinyl, but-1-yn-4-ylsulfinyl, but-2-yn-1-
Ylsulfinyl, 1-methylprop-2-ynylsulfinyl or 2-methyl
Substituted with prop-2-ynylsulfinyl, preferably propargylsulfinyl
Done C₁~ C_FourAlkyl, ie, for example, propargylsulfinylmethyl or 2
-Propargylsulfinylethyl, especially 2- (propargylsulfinyl) e
Chill; C_Three~ C_FourAlkenylsulfonyl C₁~ C_FourAlkyl: the following C_Three~ C_FourAlkenyl
Sulfonyl, such as allylsulfonyl, but-1-en-3-ylsulfonyl,
But-1-en-4-ylsulfonyl, but-2-en-1-ylsulfonyl,
1-methylprop-2-enylsulfonyl or 2-methylprop-2-enyls
C substituted with ruphonyl₁~ C_FourAlkyl, ie, for example, allylsulfonylmethyl
, 2-allylsulfonylethyl or but-1-en-4-ylsulfonylmethyl
Especially 2- (allylsulfonyl) ethyl; C_Three~ C_FourAlkynylsulfonyl C₁~ C_FourAlkyl: the following C_Three~ C_FourAlkynyl
Sulfonyl, for example propargylsulfonyl, but-1-yn-3-ylsulfo
Nil, but-1-yn-4-ylsulfonyl, but-2-yn-1-ylsulfonyl
Nyl, 1-methylprop-2-ynylsulfonyl or 2-methylprop-2-i
C substituted with nylsulfonyl, preferably propargylsulfonyl₁~ C_FourAl
I.e., for example, propargylsulfonylmethyl or 2-propargylsulfo
Nylethyl, especially 2- (propargylsulfonyl) ethyl; C_Three~ C₆Cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or
Is cyclohexyl; C_Three~ C₈Cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl,
Cyclohexyl, cyclopentyl or cyclooctyl; C_Three~ C₈Cycloalkyl C₁~ C₆Alkyl: for example, cyclopropylmethyl,
Cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclope
Methyl, cyclooctylmethyl, 2- (cyclopropyl) ethyl, 2- (
Cyclobutyl) ethyl, 2- (cyclopentyl) ethyl, 2- (cyclohexyl)
) Ethyl, 2- (cyclopentyl) ethyl, 2- (cyclooctyl) ethyl, 3
-(Cyclopropyl) propyl, 3- (cyclobutyl) propyl, 3- (cyclo
Pentyl) propyl, 3- (cyclohexyl) propyl, 3- (cyclopentyl)
) Propyl, 3- (cyclooctyl) propyl, 4- (cyclopropyl) butyl
, 4- (cyclobutyl) butyl, 4- (cyclopentyl) butyl, 4- (cyclo
Hexyl) butyl, 4- (cyclopentyl) butyl, 4- (cyclooctyl) butyl
Tyl, 5- (cyclopropyl) pentyl, 5- (cyclobutyl) pentyl, 5-
(Cyclopentyl) pentyl, 5- (cyclohexyl) pentyl, 5- (cyclo
Pentyl) pentyl, 5- (cyclooctyl) pentyl, 6- (cyclopropyl
) Hexyl, 6- (cyclobutyl) hexyl, 6- (cyclopentyl) hexyl
, 6- (cyclohexyl) hexyl, 6- (cyclopentyl) hexyl or 6-
(Cyclooctyl) hexyl; C_Three~ C₈Cycloalkyloxy C₁~ C_FourAlkyl: cyclopropyloxymethyl
1-cyclopropyloxyethyl, 2-cyclopropyloxyethyl, 1-
Cyclopropyloxyprop-1-yl, 2-cyclopropyloxyprop-1
-Yl, 3-cyclopropyloxyprop-1-yl, 1-cyclopropyloxy
Sibut-1-yl, 2-cyclopropyloxybut-1-yl, 3-cyclopro
Pyroxybut-1-yl, 4-cyclopropyloxybut-1-yl, 1-cy
Clopropyloxybut-2-yl, 2-cyclopropyloxybut-2-yl
3-cyclopropyloxybut-2-yl, 4-cyclopropyloxybuta-
2-yl, 1- (cyclopropyloxymethyl) eth-1-yl, 1- (cyclo
Propyloxymethyl) -1- (CH_Three) Eth-1-yl, 1- (cyclopropylmethyloxy) prop-1-yl, cyclobutyloxymethyl, 1-cyclobutyl
Tyloxyethyl, 2-cyclobutyloxyethyl, 1-cyclobutyloxyp
Lopa-1-yl, 2-cyclobutyloxyprop-1-yl, 3-cyclobutyl
Oxyprop-1-yl, 1-cyclobutyloxybut-1-yl, 2-cyclo
Butyloxybut-1-yl, 3-cyclobutyloxybut-1-yl, 4-cy
Clobutyloxybut-1-yl, 1-cyclobutyloxybut-2-yl, 2
-Cyclobutyloxybut-2-yl, 3-cyclobutyloxybut-2-yl
, 4-cyclobutyloxybut-2-yl, 1- (cyclobutyloxymethyl)
Eth-1-yl, 1- (cyclobutyloxymethyl) -1- (CH_Three) Eth-1-yl, 1- (cyclobutyloxymethyl) prop-1-yl, cyclopentyl
Oxymethyl, 1-cyclopentyloxyethyl, 2-cyclopentyloxy
Tyl, 1-cyclopentyloxyprop-1-yl, 2-cyclopentyloxy
Prop-1-yl, 3-cyclopentyloxyprop-1-yl, 1-cyclope
Benzyloxybut-1-yl, 2-cyclopentyloxybut-1-yl, 3-
Cyclopentyloxybut-1-yl, 4-cyclopentyloxybut-1-y
1-cyclopentyloxybut-2-yl, 2-cyclopentyloxybuta
-2-yl, 3-cyclopentyloxybut-2-yl, 4-cyclopentylo
Xylbut-2-yl, 1- (cyclopentyloxymethyl) eth-1-yl, 1
-(Cyclopentyloxymethyl) -1- (CH_Three) Eth-1-yl, 1- (cyclopentyloxymethyl) prop-1-yl, cyclohexyloxymethyl,
1-cyclohexyloxyethyl, 2-cyclohexyloxyethyl, 1-cyclo
Rohexyloxyprop-1-yl, 2-cyclohexyloxyprop-1-yl
3-cyclohexyloxyprop-1-yl, 1-cyclohexyloxyb
Ta-1-yl, 2-cyclohexyloxybut-1-yl, 3-cyclohexyl
Oxybut-1-yl, 4-cyclohexyloxybut-1-yl, 1-cyclo
Hexyloxybut-2-yl, 2-cyclohexyloxybut-2-yl, 3
-Cyclohexyloxybut-2-yl, 4-cyclohexyloxybut-2-
Yl, 1- (cyclohexyloxymethyl) eth-1-yl, 1- (cyclohexyl
Siloxymethyl) -1- (CH_Three) Eth-1-yl, 1- (cyclohexyloxymethyl) prop-1-yl, cycloheptyloxymethyl, 1-cyclohep
Tyloxyethyl, 2-cycloheptyloxyethyl, 1-cycloheptyloxy
Ciprop-1-yl, 2-cycloheptyloxyprop-1-yl, 3-cyclo
Heptyloxyprop-1-yl, 1-cycloheptyloxybut-1-yl,
2-cycloheptyloxybut-1-yl, 3-cycloheptyloxybuta-1
-Yl, 4-cycloheptyloxybut-1-yl, 1-cycloheptyloxy
But-2-yl, 2-cycloheptyloxybut-2-yl, 3-cyclohepti
Oxybut-2-yl, 4-cycloheptyloxybut-2-yl, 1- (cy
Chloheptyloxymethyl) eth-1-yl, 1- (cycloheptyloxymethyl)
) -1- (CH_Three) Eth-1-yl, 1- (cycloheptyloxymethyl) prop-1-yl, cyclooctyloxymethyl, 1-cyclooctyloxyethyl
2-cyclooctyloxyethyl, 1-cyclooctyloxyprop-1-yl
Yl, 2-cyclooctyloxyprop-1-yl, 3-cyclooctyloxy
Prop-1-yl, 1-cyclooctyloxybut-1-yl, 2-cyclooctyl
Tyloxybut-1-yl, 3-cyclooctyloxybut-1-yl, 4-cy
Crooctyloxybut-1-yl, 1-cyclooctyloxybut-2-yl
, 2-cyclooctyloxybut-2-yl, 3-cyclooctyloxybuta-
2-yl, 4-cyclooctyloxybut-2-yl, 1- (cyclooctyl
Xymethyl) eth-1-yl, 1- (cyclooctyloxymethyl) -1- (C
H_Three) Eth-1-yl or 1- (cyclooctyloxymethyl) prop-1-yl, especially C_Three~ C₆Cycloalkoxymethyl or 2- (C_Three~ C₆Cycloalkoxy
)ethyl.

The 3- to 7-membered heterocyclyl is one to three heteroatoms selected from one to three nitrogen atoms, one or two oxygen atoms and one or two sulfur atoms. Is understood to mean not only saturated heterocycles (heterocycles) or partially or completely unsaturated heterocycles (heterocycles) but also aromatic heterocycles (heterocycles).

Examples of saturated heterocycles which may have a carbonyl or thiocarbonyl ring member include: oxiranyl, thiranyl, aziridin-1-yl, aziridin-2-yl,
Diaziridin-1-yl, diaziridin-3-yl, oxetan-2-yl, oxetan-3-yl, thietane-2-yl, thietane-3-yl, azetidin-
1-yl, azetidin-2-yl, azetidin-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothiophen-2-yl, tetrahydrothiophen-3-yl, pyrrolidin-1-yl, pyrrolidin-
2-yl, pyrrolidin-3-yl, 1,3-dioxolan-2-yl, 1,3-
Dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-oxazolidine-2-yl, 1,3- Oxazolidin-3-yl, 1,3-oxazolidine-4-yl, 1,3-oxazolidine-5-yl, 1,2-oxazolidine-2
-Yl, 1,2-oxazolidin-3-yl, 1,2-oxazolidin-4-yl, 1,2-oxazolidin-5-yl, 1,3-dithiolan-2-yl, 1,
3-dithiolan-4-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-5-yl, tetrahydropyrazol-1-yl, tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydropyran- 2
-Yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, piperidin-1-yl, piperidin-2 -Yl, piperidin-3-yl, piperidin-4-yl, 1,3-dioxan-2-yl,
1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-oxathian-2-yl, 1,3-oxathian-
4-yl, 1,3-oxathian-5-yl, 1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl, morpholin-2-yl, Morpholin-3-yl, morpholin-4-yl, hexahydropyridazin-1-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl, hexahydropyrimidin-2-yl Yl, hexahydropyrimidin-4-yl, hexahydropyrimidine-
5-yl, piperazin-1-yl, piperazin-2-yl, piperazin-3-yl, hexahydro-1,3,5-triazin-1-yl, hexahydro-1,3
, 5-Triazin-2-yl, oxepan-2-yl, oxepan-3-yl,
Oxepan-4-yl, Thiepan-2-yl, Thiepan-3-yl, Thiepan-
4-yl, 1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl, 1,3-dioxepan-5-yl, 1,3-dioxepan-6-yl, 1,3
-Dithiepan-2-yl, 1,3-dithiepan-4-yl, 1,3-dithiepan-5-yl, 1,3-dithiepan-6-yl, 1,4-dioxepan-2-yl, 1,4 Dioxepan-7-yl, hexahydroazepin-1-yl, hexahydroazepin-2-yl, hexahydroazepin-3-yl, hexahydroazepin-4-yl, hexahydro-1,3-diazepin-1-yl , Hexahydro-1,3-diazepin-2-yl, hexahydro-1,3-diazepin-4-yl
Yl, hexahydro-1,4-diazepin-1-yl and hexahydro-1,4
-Diazepin-2-yl.

Examples of unsaturated heterocycles (heterocyclyls) which may contain carbonyl or thiocarbonyl ring members include: dihydrofuran-2-yl, 1,2-oxazoline-3- Yl, 1,2-oxazolin-5-yl, 1,3-oxazolin-2-yl.

Preferred among the heteroaromatic rings are those having a 5- or 6-membered structure, for example, furyls such as 2-furyl and 3-furyl, thienyls such as 2-thienyl and 3-thienyl, 2- Pyrrolyl such as pyrrolyl and 3-pyrrolyl, 3-isoxazolyl,
Isoxazolyl such as 4-isoxazolyl and 5-isoxazolyl, isothiazolyl such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl and 5 Oxazolyl such as -oxazolyl, thiazolyl such as 2-thiazolyl, 4-thiazolyl and 5-thiazolyl, imidazolyl such as 2-imidazolyl and 4-imidazolyl, 1,2,4-oxadiazole-3
Oxadiazolyl, such as -yl, 1,2,4-oxadiazol-5-yl and 1,3,4-oxadiazol-2-yl, 1,2,4-thiadiazol-3-yl, 1,2,2 4-thiadiazol-5-yl and 1,3,4-thiadiazole-
Thiadiazolyl such as 2-yl, 1,2,4-triazol-1-yl, 1,2,2
Triazolyl such as 4-triazol-3-yl and 1,2,4-triazol-4-yl, pyridinyl such as 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl such as 3-pyridazinyl and 4-pyridazinyl, 2 Pyrimidinyl such as -pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, furthermore 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, especially pyridyl, pyrimidyl, furanyl and Thienyl.

Preferably, all phenyl rings, carbocycles and heterocycles are unsubstituted.

[0020] 3- (Benzoazol-4-yl) pyrimidinedione derivative I as a herbicide
For use, the symbols preferably have the following meanings, in which case
Preferably used alone or in combination: X represents oxygen; R¹Is hydrogen, amino or C₁~ C₆Alkyl, especially hydrogen or C₁~ C_FourR represents alkyl, particularly preferably hydrogen or methyl;^TwoIs hydrogen, halogen, C₁~ C₆Alkyl, C₁~ C₆Haloalkyl or C₁~ C ₆ R represents alkylsulfonyl, especially trifluoromethyl;^ThreeRepresents hydrogen; R^FourRepresents hydrogen, fluorine or chlorine; R^FiveRepresents cyano or halogen, especially chlorine; = Y- is NN (R⁶)-Or = C (ZR⁷) Represents -S-; R⁶Is C₁~ C₆Alkyl, C_Three~ C₆Alkenyl, C_Three~ C₆Alkynyl, C₁~ C ₆ Alkylsulfonyl, (C₁~ C₆Alkyl) carbonyl, (C₁~ C₆Alkyl) thiocarbonyl, (C₁~ C₆Alkoxy) carbonyl or cyano, (C₁~ C₆Alkoxy) carbonyl, di (C₁~ C₆Alkyl) aminocarbonyl or (C₁~ C₆Alkyl) carbonyl optionally substituted with carbonyloxy₁~ C₆Al
Kill, especially C₁~ C₆Alkyl, C_Three~ C₆Alkynyl, C₁~ C₆Alkylsulfoni
Or (C₁~ C₆Represents alkoxy) carbonyl.

Furthermore, a 3- (benzoazol-4-yl) pyrimidinedione derivative Ia @ X
Is oxygen, R¹Is methyl, R^TwoIs trifluoromethyl, R^ThreeIs hydrogen, R^FourIs fluorine, R ^Five Is chlorine, and = Y- is = C (ZR⁷) -N (CH_Three)-Corresponds to I.｝:

[0022]

Embedded image Are particularly preferred, and the following compounds Ia. 1 to Ia. 272 is highly preferred:

[0023]

[Table 1]

[Table 2]

[Table 3]

[Table 4]

[Table 5]

[Table 6]

[Table 7]

[Table 8]

Furthermore, 3- (benzoazol-4-yl) pyrimidinedione derivatives of the formulas Ib to Ih are particularly preferred, especially the corresponding compounds Ia. 1 to Ia. 272 is different from compound Ib.272 only in that R ⁴ is hydrogen. 1 to Ib. 272:

[0025]

Embedded image

The corresponding compound Ia. 1 to Ia. 272 which differ from Ic.272 only in that R ¹ is hydrogen. 1 to Ic. 272:

[0027]

Embedded image

The corresponding compound Ia. 1 to Ia. 272 is different from Compound Id. 272 only in that R ¹ and R ⁴ are hydrogen. 1 to Id. 272:

[0029]

Embedded image

The corresponding compound Ia. 1 to Ia. 272 A, Y is ^{= C (ZR 7) -N (} SO 2 CH 3) - only in a point different compounds Ie. 1 to Ie. 272:

[0031]

Embedded image

The corresponding compound Ia. 1 to Ia. 272 except that R ⁴ is hydrogen and Y is ＲC (ZR ⁷ ) —N (SO ₂ CH ₃ ) —. 1-If. 272:

[0033]

Embedded image

The corresponding compound Ia. 1 to Ia. 272 except that R ¹ is hydrogen and Y is ＲC (ZR ⁷ ) —N (SO ₂ CH ₃ ) —. 1 to Ig. 272:

[0035]

Embedded image

The corresponding compound Ia. 1 to Ia. 272 is different from Compound Ih. 272 only in that R ¹ and R ⁴ are hydrogen and Y is ＣC (ZR ⁷ ) —N (SO ₂ CH ₃ ) —. 1 to I h. 272:

[0037]

Embedded image

The corresponding compound Ia. 1 to Ia. 272 A, Y is = C (ZR ⁷⁾ compounds that differ only Ii by -O- der Ru point. 1 to Ii. 272:

[0039]

Embedded image

The corresponding compound Ia. 1 to Ia. 272. Compound Ik. 272 which is different only in that Y is ＣC (ZR ⁷ ) —O— and R ⁴ is hydrogen. 1 to Ik. 272:

[0041]

Embedded image

The corresponding compound Ia. 1 to Ia. 272 A, Y is = C (ZR ⁷⁾ -O-, its to differ only in that R ¹ is a hydrogen compound Im. 1 to Im. 272:

[0043]

Embedded image

The corresponding compound Ia. 1 to Ia. 272 is a compound In. Which differs only in that Y is ＣC (ZR ⁷ ) —O— and R ¹ and R ⁴ are hydrogen. 1 to In. 272:

[0045]

Embedded image

The 3- (benzoazol-4-yl) pyrimidinedione derivatives of the formula I can be obtained in various ways, for example in one of the following ways: Method A) 3- (benzo) Reaction of an azole-4-yl) pyrimidinedione derivative I (R ¹ is hydrogen) with a compound II by a method known per se:

[0047]

Embedded image

L ¹ is a conventional leaving group such as halogen (preferably chlorine, bromine or iodine), (halo) alkylsulfonyloxy (preferably methylsulfonyloxy or trifluoromethylsulfonyloxy), arylsulfonyloxy ( Preferably, they are toluenesulfonyloxy) and alkoxysulfonyloxy (preferably, methoxysulfonyloxy or ethoxysulfonyloxy).

The process may be carried out in a protic solvent such as an inert organic solvent such as a lower alcohol (preferably methanol or ethanol), optionally as a mixture with water, or in an aprotic solvent such as an aliphatic or Cyclic ethers (eg, methyl t
tert-butyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane), aliphatic ketones (eg, acetone, diethyl ketone and ethyl methyl ketone), amides (eg, dimethylformamide and N-methylpyrrolidone), sulfoxides (eg, dimethyl Sulfoxide), urea (eg, tetramethylurea and 1,3-dimethyltetrahydro-2 (1H) -pyrimidinone),
It is common to work in carboxylic esters (eg, ethyl acetate), or halogenated aliphatic or aromatic hydrocarbons (eg, methylene chloride, dichloroethane, chlorobenzene, and dichlorobenzene).

If necessary, this method may be performed in the presence of a base. Suitable bases are inorganic bases such as carbonates (eg, sodium and potassium carbonate), bicarbonates (eg, sodium and potassium bicarbonate), alkali metal hydrides (eg, sodium hydride and potassium hydride) ), Further organic bases such as amines (e.g. triethylamine, pyridine and N, N-diethylaniline),
Or alkali metal alkoxides (e.g., sodium methoxide, sodium ethoxide, and potassium tert-butoxide).

The amounts of the base and the alkylating agent II are each preferably 0.5 to 2 times the molar amount of the starting compound I (R ¹ is hydrogen).

In general, the reaction temperature is between 0 ° C. and the boiling point of the reaction mixture, especially between 0 and 60 ° C.

A preferred variant is the cyclization of IV (R ¹ is hydrogen) or V (R ¹ is hydrogen) by method D), which is obtained without isolation from the reaction mixture of the salt of I (hydrogen (Which may contain an excess of a base such as sodium chloride, sodium alkoxide or sodium carbonate).

If these salts of compound I (R ¹ is hydrogen) cannot be obtained directly by cyclization under basic conditions as described in method D), the compounds of methods C) to F) It is obtained from the processed product in a manner known per se. For this, for example, an aqueous solution of an inorganic or organic base is treated with 3- (benzo-4-yl) pyrimidinedione derivative I (R ¹ is hydrogen). Here, usually at about 20-25 ° C., the salt forms sufficiently quickly.

At 20 to 25 ° C., about equimolar amount of 3- (benzoazol-4-yl) pyrimidinedione derivative I (R ¹ is hydrogen) is dissolved in about equimolar amount of aqueous sodium hydroxide solution. Obtaining the sodium salt is particularly effective. The corresponding salt of the 3- (benzoazol-4-yl) pyrimidindione derivative I can then be isolated by precipitation with a suitable inert solvent or by evaporating the solvent.

The salt of the 3- (benzazol-4-yl) pyrimidinedione derivative I in which the metal ion is an alkali metal ion is usually obtained by metathesis of an aqueous solution of the corresponding alkali metal salt, and comprises ammonia or phosphonium, By using a sulfonium or sulfoxonium hydroxide, ammonium, phosphonium, sulfonium and sulfoxonium salts can also be obtained.

Method B) Reaction of a 3- (benzoazol-4-yl) pyrimidinedione derivative of formula I (R ¹ is hydrogen) with an electrophilic aminating reagent in the presence of a base:

[0058]

Embedded image

The aminating reagent that has been particularly effective so far has been 2,4-dinitrophenoxyamine, but it is also possible to use, for example, hydroxylamine-O-sulfonic acid (HOSA). This HOSA is already known in the literature as an aminating reagent (eg, E. Hofer et al., Synthesis 1983, 466; W. Friedrichse
n et al., Heterocycles 20 (1983) 1271; H. Hart ea al., Tetrahedron Lett.
25 (1984) 2073; B. Vercek et al., Monatsh. Chem. 114 (1983) 789; G. Sos
nousky et al., Z. Naturforsch. 38 (1983) 884; RS Atkinson et al., J. C.
hem. Soc. Perkin Trans. 1987, 2787).

The amination is carried out in a manner known per se (eg, T. Sheradsky, Tetrah
edron Lett. 1968, 1909; MP Wentland et al., J. Med. Chem. 27 (1984) 11
03, and especially EP-A 240 194, EP-A 476697 and EP-A 51
7181 (these describe amination of uracil), see).

The reaction is usually carried out in polar solvents which have hitherto been particularly suitable, for example in dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide or in ethyl acetate.

Suitable bases are, for example, alkali metal salts (eg potassium carbonate), alkali metal alkoxides (eg sodium methoxide and potassium tert-butoxide), or alkali metal hydrides (eg sodium hydride).

The amounts of the base and the aminating agent are each preferably 0.5 to 2 times the molar amount of the starting compound.

Method C) Sulfurization of a 3- (benzoazol-4-yl) pyrimidinedione derivative of formula I (R ¹ is oxygen):

[0065]

Embedded image

Generally, sulfidation is carried out with an inert solvent or diluent such as an aromatic hydrocarbon (eg, toluene and xylene), an ether (eg, diethyl ether, 1,2-dimethoxyethane and tetrahydrofuran), or an organic amine (eg, Pyridine).

Particularly suitable sulfurizing reagents are phosphorus (V) sulfide and 2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2,4-dithione (“Lawess
on reagent ”).

Usually, an equimolar to 5-fold molar amount relative to the starting compound to be sulfurized is sufficient to carry out a substantially complete reaction.

The reaction temperature is usually from 20 to 200 ° C., preferably from 40 ° C. to the boiling point of the reaction mixture.

Method D) Cyclization of an arylurea of the formula III or an arylanilide of the formula IV in the presence of a base:

[0071]

Embedded image L ² represents lower alkyl (preferably C ₁ -C ₄ alkyl) or phenyl.

In general, the cyclization is carried out with an aprotic inert organic solvent or diluent, such as an aliphatic or cyclic ether (eg, 1,2-dimethoxyethane, tetrahydrofuran and dioxane), an aromatic compound (eg, benzene) Or toluene) or a polar solvent (eg, dimethylformamide or dimethylsulfoxide).
Mixtures of polar solvents and hydrocarbons (eg, n-hexane) are also suitable. Depending on the starting compound, water may also be suitable as a diluent.

Suitable bases are alkali metal alkoxides, especially sodium alkoxides
Preferred are alkali metal hydroxides (particularly sodium hydroxide and potassium hydroxide), alkali metal carbonates (particularly sodium carbonate and potassium carbonate), and metal hydrides (particularly sodium hydride). If sodium hydride is used as base, the process is advantageously carried out in aliphatic or cyclic ethers, dimethylformamide or dimethylsulfoxide.

Usually, a molar amount of 0.5 to 2 times the amount of IV or V is sufficient to carry out the reaction well.

In general, the reaction temperature ranges from (−78 ° C.) to the boiling point of the reaction mixture, in particular (−60)
６０60 ° C.

When R ^{1 of} formula III or IV is hydrogen, the processed product is obtained as a salt of a metal corresponding to the cation of the base used. The salt may be isolated and purified in a manner known per se, or, if desired, may be converted with an acid to give the free compound I (R ¹ is hydrogen).

Method E) Treatment of a Substituted 2-Aminoaniline Va with Nitrite:

[0078]

Embedded image

The cyclization reaction can be carried out by a method known per se (for example, Houben-Weyl,
Methoden der Organischen Chemie [Methods in Organic Chemistry], Georg
Thieme Verlag Stuttgart, Vol. E8d, First Edition 1994, pp. 409-415).

The reaction is preferably carried out in an acidic aqueous medium, but lower carboxylic acids such as, for example, acetic acid are also suitable diluents. A suitable acidic aqueous medium is in particular a dilute mineral acid, for example 10% strength hydrochloric acid.

The nitrite is preferably obtained substantially or in situ by adding the alkali metal nitrite in aqueous solution to the reaction mixture consisting of diaminobenzene in an acidic aqueous solution or carboxylic acid.

Suitable reaction temperatures are in particular from 0 to 20 ° C., very preferably about 5 ° C.

The starting compounds are expediently used in about stoichiometric amounts, or the process is carried out using a theoretically expected excess (up to 10 mol%) of nitrous acid.

The following intermediates can be cyclized in a similar manner:

[0085]

Embedded image

Method F) Condensation of a substituted 2-aminophenol, 2-aminothiophenol or 2-aminoaniline (V) with a carbonate or carboxylic acid derivative:

[0087]

Embedded image

The condensation reaction between the difunctionalized benzene V and the carbonic acid derivative or the carboxylic acid derivative is carried out by a method known per se (for example, Houben-Weyl, Methoden der Organischen Ch.
emie [Methods in Organic Chemistry], Georg Thieme Verlag Stuttgart, Chapter E
8c, 1st edition 1994, pp. 247-284; E8b, 1st edition 1994, pp. 881-901; E8a,
First Edition, 1993, pp. 1032-1078).

Preferred carbonic acid or carboxylic acid derivatives are the corresponding anhydrides, acid chlorides, orthoesters, diimides, nitriles, trichloromethyl-substituted compounds, isocyanates and their thio analogs.

Suitable solvents / diluents are especially organic solvents such as aromatic hydrocarbons (eg benzene, toluene and o-, m-, p-xylene), halogenated hydrocarbons (eg methylene chloride, chloroform and Dichloroethane), lower alcohols (eg, methanol, ethanol), aliphatic or cyclic ethers (eg, dimethoxyethane, tetrahydrofuran and dioxane), carboxylic esters (eg, ethyl acetate), or aprotic polar solvents (eg, Dimethoxyformamide and dimethylsulfoxide).

[0091] If desired, the reaction can be promoted by adding a catalytic amount of an acid. Suitable acids are in particular mineral acids (for example, hydrochloric acid) or sulfonic acids (for example, p-toluenesulfonic acid). The amount of the acid is preferably from 0.1 to 5 mol% based on the amount of V.

The reaction temperature is from 20 ° C. to the reflux temperature of the reaction mixture, especially from 60 ° C. to the reflux temperature.

The carbonic acid or carboxylic acid derivative is used in about a stoichiometric amount or in excess. If appropriate, a large excess may be used or the process may be carried out in the absence of a solvent. Preferably, it is about stoichiometric or an excess of up to 10 molar equivalents, based on the amount of V.

The substituted 2-aminophenol, -thiophenol and -aniline (V) are conveniently obtained by reducing the corresponding 2-nitrophenol, -thiophenol or -aniline VIII (see, for example, Houben-Weyl, Methoden). der Organische
n Chemie [Methods in Organic Chemistry], Georg Thieme Verlag Stuttgart,
Vol. XI / 1, 4th ed. 1957, p. 431 et seq.):

[0095]

Embedded image

Suitable reducing agents include, inter alia, the following: metallic elements such as iron, tin and zinc, suitable catalysts such as palladium or platinum on charcoal, or hydrogen in the presence of Raney nickel, or complex hydride in the presence or absence of a catalyst, for example, LiAlH ₄ and Na BH _4.

Depending on the reducing agent, the solvent is usually a carboxylic acid (eg, acetic acid and propionic acid), an alcohol (eg, methanol and ethanol), an ether (eg, diethyl ether, methyl tert-butyl ether, tetrahydrofuran and dioxane). , Aromatic compounds (benzene and toluene), and mixtures thereof.

The reaction can be carried out at a temperature of (-100) ° C. to the boiling point of the reaction mixture.

The starting compounds are usually employed in about stoichiometric amounts; however, in each case, it may be advantageous to use one or the other component in an excess of up to about 10 mol%.

2-Nitrophenol, -thiophenol and -aniline VIII can each be released from the corresponding protected nitro compound IX:

[0101]

Embedded image "Protection" is a common protecting group that protects a phenol or thiophenol as an ether or an amino group as an amide.

This protecting group can be removed by a method known per se (for example, Green
n / Wuts: Protective Groups in Organic Synthesis, John Wiley & Sons, Inc.,
Second Edition, 1991, p. 145 and below and p. 279 and below).

Suitable elimination reagents include in particular: For alkylphenols: trimethylsilyl iodide, boron tribromide, boron trichloride, aluminum trichloride, lithium chloride or hydrogen bromide; unsubstituted or For substituted benzylphenols or benzylthiophenols: boron trifluoride, hydrofluoric acid or hydrogen / catalyst, preferably noble metals (eg palladium or platinum).

The solvent / diluent is preferably chosen such that it is inert towards the desorbing agent. When a halide is used, trimethylsilyl iodide, boron tribromide, boron trichloride or aluminum trichloride, and halogenated solvents (eg, methylene chloride, chloroform, carbon tetrachloride, and dichloroethane) are particularly preferred. Hydrogen bromide is preferably used in aqueous solution, very preferably as a 48% strength solution; lithium chloride is preferably used in polar solvents (eg lower alcohols, dimethylsulfoxide and dimethylformamide); hydrogenation The decomposition method is preferably performed in a lower alcohol or carboxylic acid with or without the addition of hydrogen transfer agents (eg, cyclohexene and cyclohexadiene).

The temperature of the elimination reaction is preferably from 0 ° C. to the boiling point of the reaction mixture.

The elimination reagent is preferably used in about a stoichiometric amount or in excess. In case of excess, it is particularly preferred that it is between 1 and 10 molar equivalents relative to the amount of IX.

Finally, the protected nitro compounds IX are obtained in a manner known per se by nitrating (protected) phenols, thiophenols or anilines X (for example,
Houben-Weyl, Methoden der Organischen Chemie [Methods in Organic Chemist
ry], Georg Thieme Verlag Stuttgart, Volume 10/1, 1971, p. 479 et seq.):

[0108]

Embedded image

Suitable nitrating reagents are in particular nitric acid, mixtures of nitric acid with sulfuric acid or acetic anhydride, or nitronium salts, especially nitronium tetrafluoroborate. Mixtures of nitric acid and sulfuric acid can bring the two components by weight to the desired proportions; mixtures in which the proportion of sulfuric acid is significantly higher or in which sulfuric acid acts as a solvent are preferred. The same is true for a mixture of nitric acid and acetic anhydride. Nitronium tetrafluoroborate is preferably used in an aprotic polar solvent such as acetonitrile or nitromethane.

[0110] The reaction temperature is generally (-80) to 80 ° C, particularly (-20) to 30 ° C.

If an agent, ie nitric acid, is used in the nitration reaction, this method is preferably carried out using about an equimolar amount, or particularly preferably an excess of the nitrating reagent. If it is in excess, it can be several times the amount of X. The nitronium tetrafluoroborate is preferably used in an equimolar amount relative to the substrate or in a slight excess between 1.1 and 1.5 molar equivalents.

In a similar manner, the following intermediates can also be nitrated:

[0113]

Embedded image

The 3- (benzoazol-4-yl) pyrimidinedione derivatives of the formula I containing one or more chiral centers are usually obtained as enantiomeric or diastereomeric mixtures, which can be optionally decomposed. Substantially pure isomers can be obtained by methods commonly used for this purpose, such as crystallization or chromatography on optically active adsorption. Pure optically active isomers are advantageously obtained from the corresponding optically active starting materials.

These 3- (benzoazol-4-yl) pyrimidinedione derivatives of the formula I (R ¹ Can be converted into its salts in a manner known per se (see in this connection what is described in method A)).

The aryl ureas of the formula III are new. These are obtained in a manner known per se, for example in one of the following methods: Method G) Reaction of β-ketocarboxylic esters XIII with ureas XIV:

[0117]

Embedded image L ² is lower alkyl (preferably C ₁ -C ₄ alkyl) or phenyl.

The process is preferably carried out in an inert solvent or diluent, particularly preferably in the presence of an acid or base catalyst, in a substantially anhydrous state.

Suitable solvents or diluents are, in particular, organic solvents which are miscible with water to give an azeotrope, such as aromatic compounds (eg benzene, toluene and o-, m-, p-xylene)
, Halogenated hydrocarbons (eg, methylene chloride, chloroform, carbon tetrachloride and chlorobenzene), aliphatic and cyclic ethers (eg, 1,2-dimethoxyethane, tetrahydrofuran and dioxane), or cyclohexane, and methanol and ethanol. Alcohol.

Suitable acid catalysts include strong mineral acids (eg, sulfuric acid and hydrochloric acid), phosphorus-containing acids (eg, orthophosphoric acid and polyphosphoric acid), organic acids (eg, p-toluenesulfonic acid), and acid cation exchangers (For example, “Amberlyst 15” (manufactured by Fluka)) is preferable.

Examples of suitable base catalysts include alkali metal hydrides (eg, sodium hydride)
And particularly preferred are alkali metal alkoxides (eg, sodium methoxide and sodium ethoxide).

XIV and β-ketocarboxylic acid ester XIII are conveniently used in about stoichiometric amounts, or the process is carried out using one or more other components in a slight excess up to about 10 mole%. Is

It will usually be sufficient to use from 0.5 to 2 mol% of catalyst, based on one amount of starting compound.

The reaction is generally carried out at 60 to 120 ° C., preferably at the boiling point of the reaction mixture, in order to quickly remove the water formed.

Method H) Reaction of enol ether XV with urea XVI:

[0126]

Embedded image L ² and L ³ are each lower alkyl (preferably C ₁ -C ₄ alkyl) or phenyl.

The reaction is usually carried out in an inert organic solvent miscible with water, for example aliphatic or cyclic ethers (for example 1,2-dimethoxyethane, tetrahydrofuran and dioxane), or lower alcohols (particularly ethanol). Is carried out at 50 to 100 ° C., preferably at the boiling point of the reaction mixture.

However, the reaction is carried out with an aromatic diluent (eg, benzene, toluene and o-,
m-, p-xylene), in which case an acid catalyst (eg, hydrochloric acid and p-toluenesulfonic acid) or a base catalyst (eg, alkali metal alkoxides such as sodium methoxide and sodium ethoxide) It is recommended to add On the other hand, in this variant, the reaction temperature is usually 50-100 ° C,
The temperature is preferably from 60 to 80 ° C.

As regards the mass ratio, the proportions described in method G) apply here.

Method J) Reaction of Enaminoester XVII with Isocyanate XVIII:

[0131]

Embedded image L ² is lower alkyl (preferably C ₁ -C ₄ alkyl) or phenyl.

The reaction is carried out in a substantially anhydrous aprotic organic solvent or diluent, such as an aliphatic or cyclic ether (eg, diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane), an aliphatic or aromatic Hydrocarbons (eg, n-
Hexane, benzene, toluene and o-, m-, p-xylene, halogenated aliphatic hydrocarbons (eg, methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene), aprotic polar solvents (Eg, dimethylformamide, hexamethylphosphoric triamide and dimethylsulfoxide),
Alternatively, the reaction is performed in the presence of a mixture thereof.

If desired, the method can be carried out in the presence of a metal hydride base (eg, sodium and potassium hydride), or an organic tertiary base (eg, triethylamine and pyridine). Can simultaneously act as a solvent.

The starting compounds are expediently used in about stoichiometric amounts, or the process is carried out using one or more other components in a slight excess up to about 10 mol%. If the process is performed in the absence of a solvent in the presence of an organic base, the latter will be present in large excess.

The reaction temperature is preferably (−80) to 50 ° C., particularly preferably (−60) to 30 ° C.
° C.

In a particularly preferred embodiment, the obtained enamine ester III is converted directly (for example in situ) according to method D) with an excess of base to obtain the corresponding product of the desired I.

Method K) Reaction of enaminoester XVII with urethane XIX:

[0138]

Embedded image L ² and L ⁴ are independently of each other lower alkyl (preferably C ₁ -C ₄ alkyl)
Or phenyl.

The reaction is conveniently carried out in an aprotic polar solvent or diluent such as dimethylformamide, 2-butanone, dimethylsulfoxide and acetonitrile, advantageously a base such as an alkali metal alkoxide or an alkaline earth metal alkoxide ( In particular, the reaction is carried out in the presence of a sodium alkoxide such as sodium methoxide), an alkali metal carbonate or an alkaline earth metal carbonate (particularly, sodium carbonate), or an alkali metal hydride (eg, lithium hydride and sodium hydride). Will be

It will usually be sufficient to use from 1 to 2 moles of base relative to the amount of XVII or XIX.

The reaction temperature is generally from 80 to 180 ° C., and the boiling point of the reaction mixture is preferred.

As regards the weight ratios of the starting compounds, the proportions specified in method G) apply here.

In a particularly preferred embodiment, sodium alkoxide is used as the base and the alcohol formed during the reaction is distilled off continuously. The resulting enaminoester IV can be cyclized by method D) without isolation from the reaction mixture to give the salt of a substituted benzothiazole I (R ¹ is hydrogen).

Urethane XIX is obtained, for example, from carbonyl chloride XX and aniline XXI:

[0145]

Embedded image

In order not to make the aniline excessive, it is generally necessary to add an auxiliary base such as triethylamine, pyridine or an alkali metal carbonate to remove the hydrogen chloride formed during the reaction. Pyridine is suitable because it can be used simultaneously as a solvent.

Suitable solvents / diluents over pyridine are, in particular, aromatic hydrocarbons (eg benzene, toluene and o-, m-, p-xylene), halogenated hydrocarbons (eg methylene chloride, chloroform and dichloroethane). , Lower alcohols (methanol and ethanol), aliphatic or cyclic ethers (eg, dimethoxyethane, tetrahydrofuran and dioxane), carboxylic esters (eg, ethyl acetate)
Or an aprotic polar solvent (for example, dimethylformamide and dimethylsulfoxide).

The reaction temperature is generally from 0 ° C. to the reflux temperature of the reaction mixture.

The starting materials are expediently used in about stoichiometric amounts or a maximum of 10 mol% excess of carbonyl chloride is chosen.

The auxiliary base is usually used in an approximately equimolar amount or an excess of up to about 2 times the amount of XX or XXI. If pyridine is used as auxiliary base, even a large excess is recommended, in which case the method can be carried out without further addition of solvent.

Method L) Reaction of isocyanate XXII with aniline derivative XXI:

[0152]

Embedded image L ² is lower alkyl (preferably C ₁ -C ₄ alkyl) or phenyl.

The reaction is conveniently carried out in a substantially anhydrous aprotic organic solvent or diluent, for example, aliphatic or cyclic ethers (eg, diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane), fatty acids Aromatic or aromatic hydrocarbons (eg, n-hexane, benzene, toluene and o-, m-, p-xylene)
, Halogenated aliphatic hydrocarbons (eg, methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene), aprotic polar solvents (
For example, dimethylformamide, hexamethylphosphoric triamide and dimethyl sulfoxide), or a mixture thereof.

Optionally, the method may comprise a metal hydride base (eg, sodium hydride and potassium hydride), an alkali metal alkoxide or an alkaline earth metal alkoxide (eg, sodium methoxide, sodium ethoxide, and potassium t).
tert-butoxide), or an organic nitrogen base (e.g., triethylamine and pyridine), which can simultaneously act as a solvent.

The starting compounds are expediently used in about stoichiometric amounts, or one of the components is
Used in excess of up to mol%. If the process is carried out in the absence of a solvent in the presence of an organic base, the latter will advantageously be present in large excess.

The reaction temperature is generally from (−80) to 150 ° C., and from (−30) ° C.
The boiling point of the reaction mixture is preferably used.

The arylanilides of the formula IV are also novel; they also include, for example, amide X
It is obtained in a manner known per se by reacting XIII with urethane XXIV by method M):

[0158]

Embedded image L ² is lower alkyl (preferably C ₁ -C ₄ alkyl) or phenyl.

The reaction is advantageously carried out at normal pressure in a substantially anhydrous solvent or diluent, particularly preferably in the presence of an acid catalyst.

To obtain an enamine carboxylate IV where R ¹ is amino, it is recommended to use a compound XXIV containing a protected amino group (such as, for example, a hydrazone).

Suitable solvents / diluents are especially organic fluids which can be mixed with water to obtain an azeotrope, such as aromatic compounds (eg benzene, toluene and o-, m-, p-xylene) or halogenated hydrocarbons (eg, carbon tetrachloride and chlorobenzene).

Suitable catalysts are especially strong mineral acids (eg, sulfuric acid), organic acids (eg, p-toluenesulfonic acid), phosphorus-containing acids (eg, orthophosphoric acid and polyphosphoric acid), or acid cation exchangers (eg, , "Amberlyst 15" (Fluka).

In general, it is sufficient for the reaction temperature to be between about 70 and 150 ° C .; however, in order to quickly remove the water obtained in the reaction, the process is expediently carried out at the boiling point of the reaction mixture.

XXIII and XXIV are usually used in about stoichiometric amounts; it is preferred to use XXIV in a slight excess up to about 20 mol%.

The amide XXIII is obtained as follows (Method N):

[0166]

Embedded image

The reaction is carried out in an anhydrous, inert, aprotic solvent such as a halogenated hydrocarbon (
For example, methylene chloride, chloroform, carbon tetrachloride and chlorobenzene), aromatic hydrocarbons (eg, benzene, toluene, and o-, m-, p-xylene),
Or in an aliphatic or cyclic ether (eg diethyl ether, dibutyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane).

The reaction temperature is generally between about 70 and 140 ° C., in particular between 100 and 120 ° C.

XXV and XXI are usually used in about stoichiometric amounts, or one of the components is used in an excess of up to about 10 mol%.

The isocyanates XVII are obtained, for example, by the method O) from the aniline derivatives XXI:

[0171]

Embedded image

The process can be carried out in an inert, substantially anhydrous solvent or diluent, or in the absence of a solvent, wherein the aniline derivative XXI is converted to phosgene, ie, a “phosgene equivalent”. Product ", for example, diphosgene, triphosgene and carbonyldiimidazole, or with trichloromethylchloroformate.

Suitable solvents or diluents are especially aprotic organic solvents such as dimethylformamide or aromatic compounds (eg toluene and o-, m-, p-
-Xylene), halogenated hydrocarbons (eg, methylene chloride, chloroform, 1
, 2-dichloroethane and chlorobenzene), aliphatic or cyclic ethers (eg, 1,2-dimethoxyethane, tetrahydrofuran and dioxane), or esters (eg, ethyl acetate), and mixtures thereof.

The starting materials are expediently used in about stoichiometric amounts or one of the components is
Used in excess of up to mol%.

Depending on the aniline derivative XXI used, it may be advantageous to add a base such as triethylamine, for example, in a molar amount of 0.5 to 2 times the amount of XXI.

[0176] The reaction temperature is generally from (-20) ° C to the reflux temperature of the solvent or the reaction mixture.

The aniline derivative XXI can be obtained in a manner known per se by reducing the corresponding nitro derivative XXVI (Houben-Weyl, Methoden der Organischen).
Chemie [Methods in Organic Chemistry], Georg Thieme Verlag Stuttgart, Volume XI / 1, 4th Edition, 1957, 431 pages):

[0178]

Embedded image

With respect to the reducing agent, the solvent, the reaction temperature and the mass ratio, reference can be made to those described in the above-mentioned method F).

Compounds XXVIII and XXI may contain one or more chiral centers, in which case they are usually obtained as an enantiomeric or diastereomeric mixture. If desired, the mixture can be separated into the substantially pure isomers by methods customary for this purpose, for example by crystallization on an optically active adsorbate or by chromatography. Pure optically active isomers can also be obtained, for example, from the corresponding optically active starting materials.

Unless otherwise stated, all the methods described above can be carried out under normal pressure or under pressures which are specific to the reaction mixture. Generally, the reaction material is 0.95: 1 to
Used in a 5: 1 molar ratio.

In general, the reaction mixture is isolated by, for example, diluting the reaction solution with water and then filtering, crystallizing or extracting with a solvent, or removing the solvent and removing water with a suitable organic solvent. Work-up is carried out in a manner known per se by separating the residue in the mixture and working up the organic layer to give the product.

Compound I and its agriculturally useful salts, in the form of a mixture of isomers or of pure isomers, are suitable as herbicides. Herbicidal compositions containing I are effective at controlling vegetation in non-cultivated areas, especially at high application rates. These compositions act on weeds and pastures that remain extensive in crops such as wheat, rice, corn, soy, and cotton without substantially damaging the cultivated plants. This effect is mainly observed at low application rates.

Depending on the difference in the method of application, Compound I or herbicidal compositions containing them,
In addition, many cultivated plants can be used for the removal of unwanted plants. Suitable crops include the following: onion (Allium cepa) pineapple (Ananas comosus) peanut (Arachis hypogaea) asparagus (Asparagus officinalis sapyaspathibusaparispathibusaparisgasi.) Brassica napus var.napu
s) Turnip orchid (var. napoplasica) (Brassica napus va)
r. napobrassica Sugar beet (var. sylvestris) (Brassica rapa var.s)
ilvestris Camellia sinensis Safflower (Carthamus tinctorius) Carya illinoinensis Lemon (Citrus limon) Natsumi coffee (Citrus sinafi senafiensa sifenafies)
a, Coffea liverica)] Cucumber (Cucumis sativus) Cypressum cypress (Cydonon dactylon) Carrot (Daucus carota) Oil palm (Elays guiengi beans)
oreum, Gossypium herbaceum, Gossypium
vitifolium)] sunflower (Helianthus annuus) rubber tree (Hevea brasiliensis) barley (Hordeum vulgare) Humulus lupulus (Humulus lupulus) American potatoes (Ipomoea batatas) Juglans (Juglans regia) lentils (Lens culinaris) flax (Linum usitatissimum) tomato (Lycopersicon lycopersicum) apple Genus (Malus spec.) Keyhot mackerel (Manihot esculenta) Purple coconut palm (Medicago sativa) Musa spec. (Nicorusta tabacum (N. rustica)) (Olea europaea) Rice (Oryza sativa) Adzuki (Phaseolus lunatus) Gougling cowpea (Phaseolus vulgaris) Spruce (Picea abies) Pinus spumus prais mosaic Pyrus communis Currants (Rives sylvestre) Castor (Ricinus communis) Sugarcane (Saccharum officinarum) Rye (Secale cereal) Potato (Solanum tuberosa mulco sorghum) obroma cacao) red clover (Trifolium pratense) wheat (Triticum aestivum) Toriteikamu, drum (Triticum durum) broad bean (Vicia faba) grapes (Vitis vinifera) corn (Zea mays).

In addition, Compound I can be used in crops that are resistant to the action of herbicides as a result of cultivation including genetic engineering methods.

The compounds I or herbicidal compositions containing them can be used, for example, in aqueous solutions, powders, suspensions, highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oily dispersions It can be used in the form of pastes, dusts, dusts or granules by spraying, misting, dusting, dusting or pouring. The form of use is determined based on the purpose of use. In each case, the finest possible distribution of the active substances according to the invention is to be ensured.

Suitable inert auxiliaries are the following: medium to high boiling mineral oil fractions (for example kerosene or diesel oil, furthermore coal tar oil), and vegetable or animal sources Oils, aliphatic, cyclic and aromatic hydrocarbons (eg, paraffin, tetrahydronaphthalene, alkyl-substituted naphthalene or derivatives thereof, alkyl-substituted benzene or derivatives thereof), alcohols (eg, methanol, ethanol, propanol, butanol, cyclohexanol) ), Ketones (eg, cyclohexanone), highly polar solvents (eg, amines such as N-methylpyrrolidone, water)
. Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by the addition of water. The preparation of emulsions, pastes or oil dispersions can be carried out as such or by dissolving the substance in oil or solvents and homogeneously mixing in water with a wetting agent, tackifier, dispersant or emulsifier. . Alternatively, concentrates consisting of the active substance, wetting agents, tackifiers, dispersing or emulsifying agents and, if necessary, solvents or oils can be prepared, which are suitable for dilution with water.

Suitable surfactants include: alkali metal salts, alkaline earth metals of aromatic sulfonic acids (eg, lignin sulfonic acid, phenol sulfonic acid, naphthalene sulfonic acid, dibutyl naphthalene sulfonic acid). Salts and ammonium salts; fatty acid, alkyl sulfonate, alkyl aryl sulfonate, alkyl sulfate, lauryl ether sulfate and fatty alcohol sulfate, each alkali metal salt, alkaline earth metal salt and ammonium salt; sulfated hexadecanol; Salts of heptadecanol and octadecanol; salts of fatty alcohol glycol ethers; condensation products of sulfonated naphthalene and its derivatives with formaldehyde; naphthalene or naphthalenesulfonic acid with phenol and formaldehyde Condensation products with aldehyde, polyoxyethylene octyl phenol ether, ethoxylated isooctyl phenol, ethoxylated octyl phenol, ethoxylated nonyl phenol, alkyl phenyl polyglycol ether,
Tributylphenyl polyglycol ether, alkylaryl polyether alcohol, isotridecyl alcohol, fatty alcohol / ethylene oxide condensate, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, Sorbit ester, lignin-sulfite waste liquor and methylcellulose.

Powders, dusts and dusts can be prepared by mixing or grinding the active substances with a solid carrier material.

Granules (eg, coated granules, impregnated granules and homogeneous granules) can be prepared by binding the active substance to a solid carrier material. Examples of solid carrier materials include mineral earths (eg, silica, silica gel, silicates, talc, kaolin, limestone, lime, chalk, calcareous clay, calcareous yellow clay, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate , Magnesium oxide, ground synthetic materials), fertilizers (eg, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea), and vegetable products (eg, flour, bark, wood and walnut flour, cellulose powder), or other solids Carrier material.

The concentration of the active ingredient I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise at least one active ingredient in an amount of about 0.001 to 98% by weight, preferably 0.01 to 95% by weight. Active ingredient is 90-100%
(Preferably by NMR spectrum), preferably 95-100%.

The preparation of the compounds I according to the invention is illustrated by the following preparation examples: I: 20 parts by weight of compound no. 1 with 80 parts by weight of alkylated benzene, 10
Parts by mass of an ethylene oxide (8-10 mol) adduct of oleic acid N-monoethanolamide (1 mol), 5 parts by mass of calcium dodecylbenzenesulfonate and 5 parts by mass of ethylene oxide (1 mol) of castor oil (1 mol) 40 mol) dissolved in a mixture of adducts. The solution is poured into 100,000 parts by weight of water and finely dispersed therein, whereby an aqueous dispersion containing 0.02% by weight of active ingredient is obtained.

II: 20 parts by mass of Compound No. 2, 40 parts by weight of cyclohexanone, 30
Dissolved in a mixture consisting of parts by mass of isobutanol, 20 parts by mass of an ethylene oxide (7 mol) adduct of isooctylphenol (1 mol) and 10 parts by mass of an ethylene oxide (40 mol) adduct of castor oil (1 mol) Let it. This solution is
Pour into 00000 parts by weight of water and finely disperse therein, whereby an aqueous dispersion containing 0.02% by weight of active ingredient is obtained.

III: 20 parts by mass of the active ingredient No. 4, 25 parts by mass of cyclohexanone,
It is dissolved in a mixture consisting of 65 parts by weight of a mineral oil (fraction with a boiling point of 210-280 ° C.) and 10 parts by weight of an ethylene oxide (40 mol) adduct of castor oil (1 mol). The solution is poured into 100,000 parts by weight of water and finely dispersed therein, whereby an aqueous dispersion containing 0.02% by weight of active ingredient is obtained.

IV: 20 parts by mass of active ingredient No. 6 was completely mixed with 3 parts by weight of sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of sodium salt of lignosulfonic acid (obtained from waste sulfite) and 60 parts by weight of finely divided silica gel, The mixture is then ground with a hammer mill. Finally, add this mixture to 2
Dispersed in 0000 parts by weight of water, whereby a spray mixture containing 0.1% by weight of active ingredient is obtained.

V: 3 parts by mass of active ingredient No. 8 with 97 parts by weight of finely divided kaolin
This gives a dust containing 3% by weight of active ingredient.

VI: 20 parts by mass of active ingredient No. 12 is first mixed with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of phenol / urea / formaldehyde condensate and 68 parts by weight of paraffin mineral oil, This gives a stable oily dispersion.

VII: 1 part by weight of compound no. 14 with 70 parts by weight of cyclohexanone, 2
It is dissolved in a mixture consisting of 0 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. The mixture is then diluted with water to give the desired concentration of the active ingredient. This gives a stable emulsion concentrate.

VIII: 1 part by weight of compound no. 19, 80 parts by weight of cyclohexanone and 20 parts by weight of Uettoru (TM) EM31 is dissolved in a mixture consisting of (Wettol ^R EM31; produced by BASF; nonionic emulsifier based on ethoxylated castor oil). Thereafter, the mixture is diluted with water to give the desired concentration of active ingredient. This gives a stable emulsion concentrate.

The active ingredient I or the herbicidal composition is applied by a pre- or post-method. If some cultivated plants show little tolerance to the active ingredient, they can adhere to the leaves of undesired plants growing underneath or in the exposed soil, but have as little contact as possible with the leaves of sensitive cultivated plants As described above, the herbicidal composition can be sprayed by a spraying device (direct spraying, lay-by).

The rate of application of the active substance I depends on the purpose of the application, the season, the plant concerned and the stage of growth, and ranges from 0.001 to 3.0 kg of active substance per 0.01 km ² (ha) (a. s.), preferably from 0.01 to 1.0 kg.

To extend the range of action and to obtain synergy, 3- (benzoazole-4-
The yl) pyrimidinedione derivatives I can be mixed with the active ingredients of many other representative groups of herbicides or growth inhibitors and can be applied therewith. Suitable components for mixing include, for example, 1,2,4-thiadiazole,
, 3,4-thiadiazole, amide, aminophosphonic acid and its derivatives, aminotriazole, anilide, aryl / heteroaryloxyalkanoic acid and its derivatives, benzoic acid and its derivatives, benzothiadiazinone, 2- (heteroaroyl / aroyl) 1,3-cyclohexanedione, heteroaryl aryl ketones, benzyl iso oxazolidinone, meta -CF ₃ - phenyl derivatives, Karubame over preparative, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines, Dichloropropionic acid and its derivatives, dihydrobenzofuran, dihydrofuran-3-one, dinitroaniline, dinitrophenol, diphenyl ether, dipyridyl, halocarboxylic acid and its derivatives, urea, Enyluracil, imidazole, imidazolinone, N-phenyl-3,4,5,6-tetrahydrophthalimide, oxadiazole, oxirane, phenol, aryloxy- or heteroaryloxy-phenoxypropionate, phenylacetic acid and derivatives thereof, 2 -Phenylpropionic acid and its derivatives, pyrazole, phenylpyrazole, pyridazine, pyridinecarboxylic acid and its derivatives, pyrimidyl ether, sulfonamide, sulfonylurea, triazine, triazinone, triazolinone, triazolecarboxamide and uracil.

Furthermore, it is advantageous to apply the compounds I, alone or in combination with other herbicides, together with other cultivated plant protection agents, such as insecticides or plant fungicides or bactericides. obtain. It is also important to be able to mix with mineral salt solutions used for the cure of symptoms such as seedling deficiency, rare element deficiency, etc. Oils and oil concentrates that are harmless to plants can also be added.

Production Examples Example 1 3- [7-chloro-5-fluoro-1-methyl-1H-benzotriazol-4-yl] -1-methyl-6-trifluoromethyl-2,4 (1H,
3H) -Pyrimidinedione (Compound 2) At 20 ° C., 0.25 g of 3- [7-chloro-5-fluoro-1-methyl-1H
-Benzotriazol-4-yl] -6-trifluoromethyl-2,4 (1H,
To a mixture consisting of 3H) -pyrimidinedione, 0.12 g of potassium carbonate and 20 ml of anhydrous dimethylformamide, 0.12 g of methyl iodide was added dropwise. The reaction mixture was then stirred for a further 18 hours and treated with 50 ml of water. afterwards,
The reaction mixture was extracted three times with 20 ml each of ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate and finally concentrated. The crude product was purified by chromatography on silica gel (eluent: cyclohexane / ethyl acetate = 1: 1).

Yield: 0.07 g; ¹ H-NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 7.45 (d,
1H), 6.45 (s, 1H), 4.55 (s, 3H), 3.60 (s, 3H)
.

Example 2 3- [7-Chloro-5-fluoro-1-methyl-1H-benzotriazol-4-yl] -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione ( Compound 1) A solution obtained by dissolving 0.43 g of ethyl 3-amino-4,4,4-trifluorobut-2-enoate in 3 ml of dimethylformamide was added to a sodium atmosphere at 0 ° C. for 15 minutes under a nitrogen atmosphere. 0.13 g of methoxide was added to a solution dissolved in 7 ml of anhydrous dimethylformamide. The mixture is first stirred at 10 ° C. for 1.5 hours,
A solution of 0.57 g of ethyl 7-chloro-5-fluoro-1-methyl-1H-benzotriazol-4-ylcarbamate in 20 ml of dimethylformamide was added dropwise to the above reaction mixture over 15 minutes. The mixture is then brought to 20 ° C.
And continued stirring for 5 minutes. Thereafter, the mixture is heated to 60 ° C. and
35 g of 1.8-diazabicyclo [5.4.0] undec-7-ene (DBU)
Was added. Finally, stirring was continued at 120 ° C. for 4 hours and further at 20 ° C. for 18 hours.

For working up, the reaction mixture was poured into 100 ml of a 10% strength by weight aqueous potassium carbonate solution. The desired product was extracted with diethyl ether (2 × 50 ml) and the pH of the resulting aqueous layer was brought to 1 with hydrochloric acid followed by ethyl acetate (3.
(3 times with 0 ml).

Thereafter, the organic layer was collected, and about 20 ml of a saturated sodium chloride aqueous solution and 30 ml
Was washed with a 10% by weight aqueous solution of lithium chloride, dried over sodium sulfate and finally concentrated.

Yield: 0.25 g; ¹ H-NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 10.25 (b
r, 1H), 7.45 (d, 1H), 6.30 (s, 1H), 4.60 (s, 3H)
H).

Step 2.1: 2-Chloro-4-fluoro-N-trifluoroacetylaniline A solution of 144.3 g of trifluoroacetic anhydride in 150 ml of diethyl ether was added at 0 ° C. to 2-chloro-4-fluoro 100 g of aniline was added dropwise to a solution of 800 ml of anhydrous diethyl ether. After heating the mixture to 20 ° C.,
500 ml of water were added. The organic layer was separated, washed three times with water, then dried over sodium sulfate and finally concentrated.

Yield: 151.5 g; ¹ H-NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 8.35 (br
, 1H), 8.25 (dd, 1H), 7.20 (dd, 1H), 7.05 (dt
, 1H).

Step 2.2: 3-Chloro-5-fluoro-2N-trifluoroacetylaminonitrobenzene 375 ml of 98% strength nitric acid was added at (-5) ° C. to 2-chloro-4-fluoro-N
-75 g of trifluoroacetylaniline were slowly added dropwise to a solution of 753 ml of acetic anhydride. Thereafter, the mixture was stirred at (-5) ° C for 1 hour and heated to 20 ° C. The progress of the reaction was monitored by high pressure liquid chromatography on a RP-18 column (reverse phase-18 column on silica gel) (eluent: acetonitrile / water = 7: 3). As soon as the starting material was no longer detectable, the reaction mixture was poured into ice-cold saturated aqueous sodium chloride solution. The desired solid product is then separated,
It was washed with water and dried in a drying oven at 20 ° C. under reduced pressure for several hours.

Yield: 62.3 g; ¹ H-NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 8.50 (br)
, 1H), 7.80 (dd, 1H), 7.60 (dd, 1H).

Step 2.3: 3-Chloro-5-fluoro-2- (N-methyl-N-trifluoroacetylamino) nitrobenzene 12.0 g of methyl iodide was converted to 16.1 g of 3-chloro-5- Fluoro-2N
To a mixture consisting of trifluoroacetylaminonitrobenzene, 11.6 g of potassium carbonate and 100 ml of anhydrous dimethylformamide. Then the reaction mixture was stirred at 20 ° C. for 18 hours and 500 ml of water were added. Thereafter, the mixture was extracted three times with 100 ml of ethyl acetate each. The combined organic layers were dried over sodium sulfate and finally concentrated.

Yield: 16.3 g; ¹ H-NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 7.80 (m,
1H), 7.60 (m, 1H), 3.40 (s, 3H).

Step 2.4: 3-Chloro-5-fluoro-2-methylaminonitrobenzene 173 ml of sodium hydroxide solution was added to 16.3 g of 3-chloro-5-fluoro-2- (N-methyl-N- Trifluoroacetylamino) nitrobenzene
Added to a solution dissolved in 73 ml of ethanol. Then the mixture was stirred for 1 hour and diluted with 500 ml of water. Thereafter, extraction was performed three times with 80 ml of ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate and finally concentrated.

Yield: 10.1 g; ¹ H-NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 7.70 (dd
, 1H), 7.35 (dd, 1H), 6.70 to 6.50 (br, 1H), 3.
10 (d, 3H).

Step 2.5: 2-amino-6-chloro-4-fluoro-N-methylaniline 55.94 g of tin dichloride dihydrate was added to 10.1
g of 3-chloro-5-fluoro-2-methylaminonitrobenzene in 207 ml
Was added to a solution dissolved in absolute ethanol. The mixture was then heated at 50 ° C., and a solution of 0.94 g of sodium boranate in 55 ml of absolute ethanol was added dropwise so that the temperature of the mixture did not exceed 60 ° C. For work-up, the mixture was poured into 1 L (liter) of ice water and the pH was brought to 14 with sodium hydroxide solution. Thereafter, the mixture was extracted three times with 100 ml of tert-butyl methyl ether. The organic layer is collected, washed with water, dried over sodium sulfate,
Finally concentrated.

Yield: 7.5 g; ¹ H-NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 6.50 (dd
, 1H), 6.35 (dd, 1H), 3.90-3.60 (br, 3H), 2.
65 (s, 3H).

Step 2.6: 7-Chloro-5-fluoro-1-methylbenzotriazole An aqueous solution obtained by dissolving 3.25 g of sodium nitrite in 19 ml of water was added at 5 ° C. to 2-
7.5 g of amino-6-chloro-4-fluoro-N-methylaniline at a concentration of 10%
Was added to a solution dissolved in 117 ml of hydrochloric acid. After the reaction mixture was stirred at 5 ° C. for 1 hour, it was diluted with 200 ml of water. Thereafter, the solid was separated, washed with 3 × 50 ml of water and dried at 20 ° C. in a vacuum drying oven.

Yield: 7.2 g; ¹ H-NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 7.60 (dd
, 1H), 7.30 (dd, 1H), 4.55 (s, 3H).

Step 2.7: 7-Chloro-5-fluoro-1-methyl-4-nitrobenzotriazole 0.65 ml of 98% strength nitric acid was added at (−20) ° C. to 7-chloro-5-fluoro-1. -1.5 g of methylbenzotriazole was slowly dropped into a solution of 28 ml of concentrated sulfuric acid. Thereafter, the mixture was stirred at 0 ° C. for 1 hour and heated to 20 ° C.
Stirring was then continued for 18 hours, after which the reaction mixture was poured into 500 ml of ice water.
The solid was separated, washed with water and dried in a vacuum drying oven at 20 ° C.

Yield: 1.66 g; ¹ H-NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 7.50 (d,
1H), 4.65 (s, 3H).

Step 2.8: 4-Amino-7-chloro-5-fluoro-1-methylbenzotriazole 1.66 g of 7-chloro-5-fluoro-1-methyl-4-nitrobenzotriazole was added to Step 2 Reduction with tin dichloride / sodium boranate in a manner analogous to that described in 5.5.

Yield: 1.27 g; ¹ H-NMR (250 MHz, in (CD ₃ ) ₂ SO): δ [ppm] = 7.45 (d, 1H), 6.25 (br, 2H), 4. 45 (s, 3H), 4.30 (q
, 2H), 1.35 (t, 3H).

Step 2.9: Ethyl 7-chloro-5-fluoro-1-methyl-1H-benzotriazol-4-ylcarbamate 2.28 g of ethyl chloroformate are slowly added at 0 ° C. to 13 ml of anhydrous pyridine. It was added dropwise and the mixture was stirred at this temperature for 15 minutes. Then, 4-amino-7
20 ml of -chloro-5-fluoro-1-methylbenzotriazole 1.27 g
Was added dropwise at 0 ° C. Stirring was then firstly continued at 0 ° C. for 30 minutes, after which the mixture was heated at 20 ° C. and stirred again for 18 hours. Finally, the reaction mixture was poured into 100 ml of 10% strength hydrochloric acid. Thereafter, the mixture is quenched with 50 ml t
Extracted three times with tert-butyl methyl ether. The combined organic layers were washed with 100 ml of water and concentrated. 50 ml of diethyl ether were added to the residue. Undissolved components were separated and washed with 3 × 30 ml of diethyl ether. The ether layer was collected and concentrated.

Yield: 0.37 g; ¹ H-NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 7.35 (d,
1H), 6.90 (br, 1H), 4.55 (s, 3H).

Example 3 3- [7-Chloro-5-fluoro-1-methyl-2-trifluoromethyl-1H-benzimidazol-4-yl] -1-methyl-6-trifluoromethyl-2, 4 (1H, 3H) -pyrimidinedione (Compound 1.5) 2.46 g of 3- [7-chloro-5-fluoro-1-methyl-2-trifluoromethyl-1H-benzimidazol-4-yl]- 6-trifluoromethyl-
2,4 (1H, 3H) -pyrimidinedione was alkylated with methyl iodide by a method similar to that described in Example 1. The crude product was purified by chromatography on silica gel (eluent: cyclohexane / ethyl acetate = 2: 1).

Yield: 1.4 g; ¹ H-NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 7.35 (d,
1H), 6.40 (s, 1H), 4.30 (s, 3H), 3.55 (s, 3H)
.

Example 4: 3- [7-Chloro-5-fluoro-1-methyl-2-trifluoromethyl-1H-benzimidazol-4-yl] -1-amino-6-trifluoromethyl-2, 4 (1H, 3H) -pyrimidinedione (compound 6) 0.25 g of 2,4-dinitro-O-aminophenol was added to 0.5 g of 3- [
7-Fluoro-1-methyl-2-trifluoromethyl-1H-benzimidazol-4-yl] -6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione, 2.35 g of carbonic acid It was added to a mixture consisting of potassium and 5 ml of ethyl acetate. The mixture was stirred at 20 ° C. for 18 hours and then diluted with 50 ml of ethyl acetate. The resulting mixture was washed with 3 × 30 ml of water, dried over sodium sulfate and finally concentrated. The crude product was purified by medium pressure liquid chromatography (MPLC; eluent: cyclohexane / ethyl acetate = 2: 1).

Yield: 0.4 g; ¹ H-NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 7.35 (d,
1H), 6.30 (s, 1H), 4.65 (s, 2H), 4.25 (s, 3H)
.

Example 5: 3- [7-Chloro-5-fluoro-1-methyl-2-trifluoromethyl-1H-benzimidazol-4-yl] -6-trifluoromethyl-2
, 4 (1H, 3H) -pyrimidinedione (compound 4) A solution prepared by dissolving 4.31 g of ethyl 3-amino-4,4,4-trifluorobut-2-enoate in 20 ml of dimethylformamide was treated with 0 to 5 0.82 at ° C
g of sodium hydride was added dropwise to a solution of 50 ml of anhydrous dimethylformamide. Thereafter, the mixture was stirred at the same temperature for 1 hour, and 7-chloro-5-fluoro-4-isocyanato-1-methyl-2-trifluoromethylbenzimidazole (from step 5.4) was dissolved in 40 ml of dimethylformamide. The solution,
(−30 ° C.). Stirring was then continued at (-30) C for 1 hour and at 20 C for another hour.

For working up, the reaction mixture was carefully poured into 200 ml of ice water. A solid was obtained by acidification with 10% strength hydrochloric acid, which was filtered off, washed with water and dried at 20 ° C. in a vacuum drying oven. Purification by flash chromatography (eluent: cyclohexane / ethyl acetate = 2: 1), 5.08 g of desired product
I got

After separation of the solid, the desired product still remaining in the filtrate (2.46 g)
The filtrate was extracted three times with 0 ml tert-butyl methyl ether, the combined ether layers were washed, they were dried over sodium sulfate and isolated by concentration.

Total yield: 7.54 g; ¹ H-NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 7.40 (d,
1H), 6.30 (s, 1H), 4.30 (s, 3H).

Step 5.1: 7-Chloro-5-fluoro-1-methyl 2-trifluoromethylbenzimidazole 15.5 g of 3-chloro-5-fluoro-2- (N-methyl-N-trifluoroacetyl Amino) nitrobenzene (step 2.3) is reduced with tin disodium / sodium boranate by a method analogous to that described in step 2.5 without isolation of the intermediate to the corresponding amino compound The amino compound was then spontaneously cyclized with removal of water to give the desired product.

Yield: 9.32 g; ¹ H-NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 7.45 (d,
1H), 7.20 (d, 1H), 4.25 (s, 3H).

Step 5.2: 76.3-chloro-5-fluoro-1-methyl-4-nitro-2-trifluoromethylbenzimidazole 46.3 ml of 98% strength nitric acid are added at 0 ° C. to 7-chloro-5- 9.65 g of fluoro-1-methyl-2-trifluoromethylbenzimidazole was added to acetic anhydride.
The solution was slowly dropped into 5 ml of the solution. After the mixture was stirred at 0 ° C. for 1 hour,
Heat carefully to 20 ° C. (Because an exothermic reaction takes place, the temperature is kept below 25 ° C. in an ice bath.) The reaction mixture was then first stirred at 20 ° C. for a further 2 hours and then poured into ice-cold saturated aqueous sodium chloride solution. The solid formed is separated, washed with water and
It was dried in a vacuum drying oven at 0 ° C.

Yield: 8.5 g; ¹ H-NMR (400 MHz, in CDCl ₃ ): δ [ppm] = 7.40 (d,
1H), 4.35 (s, 3H).

Step 5.3: 4-Amino-7-chloro-5-fluoro-1-methyl-2-trifluoromethylbenzimidazole 8.71 g of 7-chloro-5-fluoro-1-methyl-4-nitro -2-Trifluoromethylbenzimidazole was reduced using a method similar to that described in step 2.5 using tin dichloride / sodium boranate.

Yield: 6.3 g; ¹ H-NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 7.05 (d,
1H), 4.45 (br, 2H), 4.20 (s, 3H).

Step 5.4: 7-Chloro-5-fluoro-4-isocyanato-1-methyl-2
-Trifluoromethylbenzimidazole 23.32 g of diphosgene are added to a solution of 6.3 g of 4-amino-7-chloro-5-fluoro-1-methyl-2-trifluoromethylbenzimidazole in 100 ml of anhydrous toluene. Was added. The mixture was then refluxed for 6 hours. The reaction mixture was stirred at 20 ° C. for a further 18 hours and then concentrated. The crude product obtained is reacted directly without purification to give the final product I.I. 4 was obtained.

Example 6: 3- [7-Chloro-1,2-dimethyl-5-fluoro-1H-benzimidazol-4-yl] -1-methyl-6-trifluoromethyl-2,4 (
1H, 3H) -pyrimidinedione (compound 8) 0.33 g of 3- [7-chloro-1,2-dimethyl-5-fluoro-1H-benzimidazol-4-yl] -6-trifluoromethyl-2, 4 (1H, 3H
) -Pyrimidinedione was alkylated with methyl iodide by a method similar to that described in Example 1.

Yield: 0.04 g; ¹ H-NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 7.10 (d,
1H), 6.40 (s, 1H), 4.00 (s, 3H), 3.55 (s, 3H)
, 2.55 (s, 3H).

Example 7: 3- [7-Chloro-1,2-dimethyl-5-fluoro-1H-benzimidazol-4-yl] -6-trifluoromethyl-2,4 (1H, 3H)
-Pyrimidinedione (Compound 7) 7-chloro-1,2-dimethyl-5-fluoro-4-isocyanatobenzimidazole of Step 7.4 was converted to ethyl 3-amino-4,4,4-trifluorobuta-
The 2-enoate was reacted in a manner analogous to that described in Example 5. The crude product was purified by medium pressure liquid chromatography (eluent: ethyl acetate / methanol = 15: 1).

Yield: 0.7 g; ¹ H-NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 7.15 (d,
1H), 6.20 (s, 1H), 4.05 (s, 3H), 2.55 (s, 3H)
.

Step 7.1: 7-Chloro-1,2-dimethyl-5-fluorobenzimidazole 100 ml of 10% strength hydrochloric acid are added to 6.96 g of 2-amino-6-chloro-4-
Fluoro-N-methylaniline (from step 2.5) was added to a solution of 4.1 g of acetic anhydride. The mixture was then refluxed for 4 hours. After cooling, the mixture was taken up in ice water. Thereafter, the mixture was carefully neutralized with an aqueous sodium carbonate solution. The solid crude product formed was separated off, washed with water and dried at 20 ° C. in a vacuum drying oven.

Yield: 7.92 g; ¹ H-NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 7.25 (dd
, 1H), 6.95 (dd, 1H), 4.00 (s, 3H), 2.55 (s, 3H)
H).

Step 7.2: 7-Chloro-1,2-dimethyl-5-fluoro-4-nitrobenzimidazole (-5) At a temperature of not more than 0 ° C., 98% nitric acid was added to 7.92 g of 7-chloroform. -1,2
-Dimethyl-5-fluorobenzimidazole was added dropwise to a solution of 139 ml of concentrated sulfuric acid, and the progress of the reaction was monitored by high pressure liquid chromatography (HPLC) on an RP-18 column (eluent: acetonitrile / water = 1). : 1). As soon as the starting material was no longer detectable, the reaction mixture was poured into ice-water and brought to pH 14 with sodium hydroxide solution. The solid was separated, washed with water and dried at 20 ° C. in a vacuum drying oven. The two stereoisomeric nitro compounds formed were separated by flash chromatography on silica gel (eluent: ethyl acetate; the first product eluted was the desired stereoisomer).

Yield: 5.6 g; ¹ H-NMR (400 MHz, in CDCl ₃ ): δ [ppm] = 7.05 (d,
1H), 4.10 (s, 3H), 2.65 (s, 3H).

Step 7.3: 4-amino-7-chloro-1,2-dimethyl-5-fluorobenzimidazole 5.6 g of 7-chloro-1,2-dimethyl-5-fluoro-4-nitrobenzimidazole Was reduced using tin dichloride / sodium boranate in a manner analogous to that described in step 2.5. The obtained crude product was used directly in step 7.4 without purification.

Yield: 4.1 g.

Step 7.4: 7-Chloro-1,2-dimethyl-5-fluoro-4-isocyanatobenzimidazole 4.1 g of 4-amino-7-chloro-1,2-dimethyl-5-fluorobenzo Imidazole was reacted with diphosgene in a manner similar to that described in step 5.4. The crude product obtained is reacted directly without further purification to give the final product I.I. 7 was obtained.

Example 8: 3- [7-Chloro-2-dimethylamino-5-fluorobenzoxazol-4-yl] -1-methyl-6-trifluoromethyl-2,4- (1H
(3H) -pyrimidinedione (compound 19) 1.0 g of 3- [2-amino-4-chloro-6-fluoro-3-hydroxyphenyl] -1-methyl-6-trifluoromethyl-2,4- ( 1H, 3H) -pyrimidinedione and 0.5 g of dichloromethyleneimmonium chloride
methyleneimmonium chloride) in 100 ml of 1,2-dichloroethane, take this mixture into a pressure-resistant glass holder, and place in a sealed pressure-resistant container.
Heated at 20 ° C. for 5 hours. During this process, the intrinsic pressure of the vessel rose to about 5 bar. Then the container was cooled. The pure product solution was washed with dilute aqueous potassium carbonate.

The organic layer was dried over sodium sulfate and finally concentrated. The crude product was purified by flash chromatography using a short column (eluent: cyclohexane / tert-butyl methyl ether = 8: 2).

Yield: 0.5 g; ¹ H-NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 6.85 (d,
1H), 6.4 (s, 1H), 3.6 (s, 3H), 3.25 (s, 6H).

Step 8.1: 3- [4-Chloro-6-fluoro-3-methoxy-2-nitrophenyl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidine Dione A nitrated acid consisting of 20.4 ml of concentrated sulfuric acid and 25.5 ml of 98% strength nitric acid was added to 51.0 g of 3- [4-chloro-6-fluoro-3-methoxy) while cooling to (-20) ° C. Phenyl] -1-methyl-6-trifluoromethyl-2,4- (
1H, 3H) -pyrimidinedione was slowly dropped into a solution of 1 L of concentrated sulfuric acid. After the addition, stirring was continued at (−20) ° C. for 30 minutes. Thereafter, the reaction mixture was stirred in 1 L of ice water. The solid formed was separated, washed with water and dried in a vacuum drying oven at 20 ° C.

Yield: 57.0 g; ¹ H-NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 7.55 (d,
1H), 6.35 (s, 1H), 4.05 (s, 3H), 3.55 (s, 3H)
.

Step 8.2: 3- [4-Chloro-6-fluoro-3-hydroxy-2-nitrophenyl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H)-
Pyrimidinedione 19.0 g of lithium chloride was converted to 57.0 g of 3- [4-chloro-6-fluoro-3-methoxy-2-nitrophenyl] -1-methyl-6-trifluoromethyl-2,4- ( 1H, 3H) -Pyrimidinedione was added to a solution of about 500 ml of anhydrous dimethylformamide. Then the mixture was stirred at 80-90 ° C. for 3 hours. After cooling, 1 L of water was added to the reaction mixture. Desired product is 3 × 2
Extracted with 00 ml of methyl tert-butyl ether. The ether layer was washed repeatedly with water and dried and finally concentrated.

Yield: 46.1 g; ¹ H-NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 7.65 (d,
1H), 6.35 (s, 1H), 3.60 (s, 3H).

Step 8.3: 3- [2-Amino-4-chloro-6-fluoro-3-hydroxyphenyl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H)-
Pyrimidinedione 34.0 g of iron powder are mixed at 65 ° C. with 46.0 g of 3- [4-chloro-6-fluoro-3-hydroxy-2-nitrophenyl] -1-methyl-6-trifluoromethyl-2. , 4- (1H, 3H) -pyrimidinedione in 423 ml of water and 36.
It was added little by little to an aqueous solution dissolved in 8 ml of concentrated hydrochloric acid. The mixture was then refluxed for 3 hours. After cooling, the mixture was shaken well with 500 ml of ethyl acetate. The organic layer, Cerrito (registered trademark) (Celite ^R: Manville Corp.) was removed from the inorganic material to more remaining to filtration using. The filtrate was dried over sodium sulfate and finally concentrated.

Yield: 37.5 g; ¹ H-NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 6.65 (d,
1H), 6.40 (s, 1H), 3.60 (s, 3H).

Example 9: 3- [7-Chloro-5-fluorobenzoxazol-4-yl]
-1-Methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione (Compound 12) 0.5 g of trimethyl orthoformate was added to 0.5 g of 3- [2-amino-4-chloro -6-Fluoro-3-hydroxyphenyl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione (from step 8.3)
It was added to a solution dissolved in 0 ml of anhydrous methanol. Thereafter, the mixture was refluxed for 20 hours. The solvent and excess orthoester were then removed under reduced pressure. The residue was dissolved in ethyl acetate. The organic layer is washed with water and then dried over sodium sulfate,
Finally concentrated. The crude product was purified by flash chromatography (
Eluent: cyclohexane / tert-butyl methyl ether = 3: 1).

Yield: 0.26 g; ¹ H-NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 8.20 (s,
1H), 7.40 (d, 1H), 6.40 (s, 1H), 3.60 (s, 3H)
.

Example 10: 3- [7-Chloro-5-fluoro-2-methoxybenzoxazol-4-yl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3
H) -Pyrimidinedione (Compound 14) 1.0 g of 3- [2-amino-4-chloro-6-fluoro-3-hydroxyphenyl] -1-methyl-6-trifluoromethyl-2,4- (1H (3H) -pyrimidinedione (according to step 8.3) with tetramethyl orthocarbonate in Example 9
The reaction was carried out by a method similar to the method described in (1).

Yield: 0.7 g; ¹ H-NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 7.10 (d,
1H), 6.40 (s, 1H), 4.20 (s, 3H), 3.60 (s, 3H)
.

In addition to the 3- (benzoazol-4-yl) pyrimidinedione derivatives of the above Formula I, other compounds that are, or can be, prepared in an analogous manner are listed in Table 2 below. Listed:

[0268]

[Table 9]

[Table 10]

[Table 11]

[Use Example] The herbicidal action of the 3- (benzoazol-4-yl) pyrimidinedione derivative I was shown in the following greenhouse experiment. A plastic flower pot was used as a cultivation vessel, and loamy sand containing about 3.0% humus was used as a culture medium. The seeds of the test plants were sown for each type. In the case of the pre-emergence treatment, the active ingredient suspended or emulsified in water was directly sprayed using a fine spray nozzle after seeding. The container was lightly watered to promote budding and growth, and then covered with clear plastic until the plants took root. As long as the active ingredient does not harm, this coating leads to a uniform emergence of the test plants. By post-emergence treatment, the test plants were only treated with the active ingredients suspended or emulsified in water after reaching a plant height of 3 to 15 cm, depending on the growth type. For this purpose, the test plants can be directly sown and cultivated in the same container, or they can be initially planted separately as seedlings and transplanted into test containers two to three days before the treatment takes place. . The post application rate was 15.6 g or 7.8 g of active substance per hectare. Each test plant was kept at 10 to 25 ° C or 20 to 35 ° C depending on the type, and the experimental period was set to 2 to 4 weeks. During this time, the test plants were managed and the response to each treatment was evaluated. The evaluation was performed using a scale of 0-100. On this scale, 100 indicates that the plant has not sprouted at all, or at least that the parts above the ground have been destroyed, and 0 indicates that there has been no damage and normal growth has occurred. The plants used in the greenhouse experiments were of the following types:

[0270]

[Table 12]

The post-application rate was 15.6 g / 0.01 km ² (1 hectare) and 7. 8 g, Compound No. No. 18 showed an extremely good herbicidal effect on the above-mentioned weeds.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl.⁷ Identification symbol FI Theme coat II (reference) C07D 413/04 C07D 417/04 417/04 239/54 Z (81) Designated country EP (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE), EA (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), AL, AU, BG, BR, BY, CA , CN, CZ, GE, HU, ID, IL, IN, JP, KR, KZ, LT, LV, MK, MX, NO, NZ, PL, RO, RU, SG, SI, SK, TR, UA, US, VN (72) Inventor Menges, Marx Germany, D-64625, Bensheim, Jako-Prael-Strasse, 18 (72) Inventor Menke, Olaf Germany, D-67317, Altreiningen, Lerchenweg, 3 (72) Inventor Scheffer, Peter Germany, -67308, Ottersheim, Römerstraße, 1 (72) Inventor Zagar, Cyril Germany, D-67061, Ludwigshafen, Georg-Helberg-Strasse, 31 (72) Inventor Heistracher, Elisabeth Germany, D -68159, Mannheim, Day 3. 4 (72) Inventor Otten, Martina Germany, D-67069, Ludwigshafen, Gunterstrasse, 28 (72) Inventor Walter, Helmut Germany, D-67283, Obrichheim, Grünstater, Strasse, 82 (72) Inventor Westphalen, Carl-Otto Germany, D-67346, Speyer, Mouthbergweg, 58 F term (reference) 4C063 AA01 BB02 CC29 CC42 CC52 CC62 DD26 DD29 EE03 4H011 AB01 BA01 BB09 BB10 BC01 BC03 BC05 BC07 BC08 BC14 BC18 BC19 BC20 BC22 DA02 DA14 DA16 DD03 DH10 [Continued from abstract] Lucil, Amino C₁~ C_FourAlkyl, C₁~ C_FourAlkyl amino C₁~ C_FourAlkyl, di (C ₁~ C_FourAlkyl) amino C₁~ C_FourAlkyl, C₁~ C_FourAlkylthio C₁~ C_FourAl Kill, C₁~ C_FourHaloalkylthio C₁~ C_FourAlkyl, C_Three ~ C_FourAlkenylthio C ₁~ C_FourAlkyl, C_Three~ C_FourAlkynylthio C₁~ C_FourAlkyl, C₁~ C_FourAlkylsulfinyl C₁~ C_FourAlkyl, C₁~ C_FourHaloalkylsulfinyl C₁~ C_FourAlkyl, C_Three~ C_FourAlkenylsulfinyl C₁~ C_FourAlkyl, C_Three~ C_FourAlkynyl sulfinyl C₁~ C_FourAlkyl, C₁~ C_FourAlkylsulfonyl C₁ ~ C_FourAlkyl, C₁~ C_FourHaloalkylsulfonyl C₁~ C_FourAlkyl, C_Three~ C_FourAlkenylsulfonyl C₁~ C_Four Alkyl, C_Three~ C_FourAlkynylsulfonyl C₁~ C_FourAl Kill, C_Three~ C₆Alkenyl, cyano C_Three~ C₆Alkenyl, C_Three~ C₆Haloalkenyl, C _Three~ C₆Alkynyl, cyano C_Three~ C₆Alkynyl, C_Three~ C₆Haloalkynyl, hydroxycarbonyl C₁~ C_FourAlkyl, (C₁~ C_FourAlkoxy) carbonyl C₁~ C_FourAlkyl, (C₁~ C_FourAlkylthio) carbonyl C₁~ C_FourAlkyl, aminocarbonyl C₁~ C_FourAlkyl, (C₁~ C_FourAlkylamino) carbonyl C₁~ C_FourAlkyl, di (C₁~ C_FourAlkyl) aminocarbonyl C₁~ C_FourAlkyl, di (C ₁~ C_FourAlkyl) phosphonyl C₁~ C_FourAlkyl, C_Three~ C₈Cycloalkyl, C_Three~ C₈Cycloalkyl C₁~ C_FourAlkyl, phenyl, phenyl C₁~ C_FourAlkyl, 3- to 7-membered heterocyclyl or heterocyclyl C₁~ C_FourAlkyl, which may have carbonyl or thiocarbonyl ring members, respectively, and the cycloalkyl, phenyl and heterocyclyl rings each have from 1 to 4 of the following groups: cyano, nitro, amino , Hydroxyl, carboxyl, halogen, C₁~ C_FourAlkyl, C₁ ~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourHello alkoxy, C₁~ C_FourAlkylthio, C₁~ C_FourHaloalkirthio, C₁~ C_FourAlkylsulfonyl, C₁~ C_FourHaloalkylsulfonyl, (C₁~ C_FourAlkoxy) carbonyl, (C₁~ C_FourAlkyl) carbonyl, (C₁~ C_FourHaloalkyl) carbonyl, (C₁~ C_FourAlkyl) carbonyloxy, (C₁~ C_FourHaloalkyl) carbonyloxy and di (C₁~ C_FourAlkyl) amino, or if Z is a chemical bond, optionally R⁷Further comprises hydrogen, hydroxyl, cyano, mercapto, amino, halogen, -CH (OH) -CH_Two-R⁹, -CH (halogen) -CH_Two-R⁹, -CH_Two -CH (halogen) -R⁹, -CH = CH-R⁹Or -CH = C (halogen) -R⁹(This R⁹Is hydroxycarbonyl, (C₁~ C_FourAlkoxy) carbonyl, (C₁~ C_FourAlkylthio) carbonyl, aminocarbonyl, (C₁~ C_FourAlkylamino) carbonyl or di (C₁~ C_FourAlkyl) aminocarbonyl) or R⁷And R⁸Are united into one to four C₁~ C_FourAn alkyl group or one or two (C₁~ C_FourAlkoxy) which may have a carbonyl group and form a 1,3-propylene, tetramethylene, pentamethylene or ethyleneoxyethylene chain]. Or an agriculturally useful salt of Compound I.

Claims (9)

[Claims] 1. A compound of the formula I:Wherein X represents oxygen or sulfur;¹Is hydrogen, amino, C₁~ C₆Alkyl or C₁~ C₆Represents haloalkyl; R^TwoIs hydrogen, halogen, C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₁~ C₆ Alkylthio, C₁~ C₆Alkylsulfinyl or C₁~ C₆Alkylsulfonyl
R;^ThreeIs hydrogen, halogen or C₁~ C₆R represents alkyl;^FourRepresents hydrogen or halogen; R^FiveIs cyano, halogen, C₁~ C₆Alkyl, C₁~ C₆Haloalkyl, C₁~ C ₆ Alkoxy or C₁~ C₆Represents haloalkoxy; = Y- represents = NN- (R⁶)-, = C (ZR⁷) -N (R⁶)-, = C (ZR⁷)
-O- or = C (ZR⁷) Represents -S-; R⁶Is C₁~ C₆Alkyl, C₁~ C_FourHaloalkyl, C_Three~ C₆Cycloalkyl, C_Three~ C₆Alkenyl, C_Three~ C₆Alkynyl, C₁~ C₆Alkylsulfonyl, (C ₁ ~ C₆Alkyl) carbonyl, (C₁~ C₆Haloalkyl) carbonyl, (C₁~ C₆Alkyl) thiocarbonyl, (C₁~ C₆Alkoxy) carbonyl, (C₁~ C ₆ Alkoxy) thiocarbonyl or cyano, C₁~ C₆Alkoxy, C₁~ C₆Alkylthio, (C₁~ C₆Alkoxy) carbonyl, (C₁~ C₆Alkylamino)
Carbonyl, di (C₁~ C₆Alkyl) aminocarbonyl or (C₁~ C₆Al
C) optionally substituted with carbonyloxy₁~ C₆Z represents a chemical bond, oxygen, sulfur, -S (O)-, -S (O)_Two-, -NH- or -N (R⁸R)⁷And R⁸Are independently of each other₁~ C₆Alkyl, C₁~ C₆Haloal
Kill, hydroxy C₁~ C_FourAlkyl, cyano C₁~ C_FourAlkyl, C₁~ C_FourArco
Kishi C₁~ C_FourAlkyl, C₁~ C_FourHaloalkoxy C₁~ C_FourAlkyl, C_Three~ C_FourA
Lucenyloxy C₁~ C_FourAlkyl, C_Three~ C_FourAlkynyloxy C₁~ C_FourAlkyl
, C_Three~ C₈Cycloalkoxy C₁~ C_FourAlkyl, amino C₁~ C_FourAlkyl, C₁~ C_FourAlkylamino C₁~ C_FourAlkyl, di (C ₁ ~ C_FourAlkyl) amino C₁~ C_FourAlkyl, C₁~ C_FourAlkylthio C₁~ C_FourAl
Kill, C₁~ C_FourHaloalkylthio C₁~ C_FourAlkyl, C_Three~ C_FourAlkenylthio C ₁ ~ C_FourAlkyl, C_Three~ C_FourAlkynylthio C₁~ C_FourAlkyl, C₁~ C_FourAlkyl
Sulfinyl C₁~ C_FourAlkyl, C₁~ C_FourHaloalkylsulfinyl C₁~ C_FourA
Luquil, C_Three~ C_FourAlkenylsulfinyl C₁~ C_FourAlkyl, C_Three~ C_FourAlkini
Rusulfinyl C₁~ C_FourAlkyl, C₁~ C_FourAlkylsulfonyl C₁~ C_FourArchi
Le, C₁~ C_FourHaloalkylsulfonyl C₁~ C_FourAlkyl, C_Three~ C_FourAlkenyls
Ruphonyl C₁~ C_FourAlkyl, C_Three~ C_FourAlkynylsulfonyl C₁~ C_FourAlkyl,
C_Three~ C₆Alkenyl, cyano C_Three~ C₆Alkenyl, C_Three~ C₆Haloalkenyl, C _Three ~ C₆Alkynyl, cyano C_Three~ C₆Alkynyl, C_Three~ C₆Haloalkynyl, hide
Roxycarbonyl C₁~ C_FourAlkyl, (C₁~ C_FourAlkoxy) carbonyl C₁~ C_FourAlkyl, (C₁~ C_FourAlkylthio) carbonyl C₁~ C_FourAlkyl, amino carbonyl C₁~ C_FourAlkyl, (C₁~ C_FourAlkylamino) carbonyl C₁~ C_Four Alkyl, di (C₁~ C_FourAlkyl) aminocarbonyl C₁~ C_FourAlkyl, di (C ₁ ~ C_FourAlkyl) phosphonyl C₁~ C_FourAlkyl, C_Three~ C₈Cycloalkyl, C_Three ~ C₈Cycloalkyl C₁~ C_FourAlkyl, phenyl, phenyl C₁~ C_FourAlkyl, 3- to 7-membered heterocyclyl or heterocyclyl C₁~ C_FourAlkyl (this hetero
Cycyl may each have a carbonyl or thiocarbonyl ring member)
And the cycloalkyl, phenyl and heterocyclyl rings each have from 1 to 4
Groups: cyano, nitro, amino, hydroxyl, carboxyl, halogen, C₁ ~ C_FourAlkyl, C₁~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourHaloalkoxy, C₁~ C_FourAlkylthio, C₁~ C_FourHaloalkylthio, C₁~ C_FourArchi
Rusulfonyl, C₁~ C_FourHaloalkylsulfonyl, (C₁~ C_FourAlkoxy) cal
Bonil, (C₁~ C_FourAlkyl) carbonyl, (C₁~ C_FourHaloalkyl) carboni
Le, (C₁~ C_FourAlkyl) carbonyloxy, (C₁~ C_FourHaloalkyl) carbo
Nyloxy and di (C₁~ C_FourHaving a substituent selected from alkyl) amino
Or if Z is a chemical bond, optionally R⁷Further comprises hydrogen, hydroxyl, cyano, mercapto, amino, halogen, -CH (OH) -CH_Two-R⁹, -CH (c
Rogen) -CH_Two-R⁹, -CH_Two-CH (halogen) -R⁹, -CH = CH-R⁹ Or -CH = C (halogen) -R⁹(This R⁹Is hydroxycarbonyl, (C₁~ C_FourAlkoxy) carbonyl, (C₁~ C_FourAlkylthio) carbonyl, aminocarbonyl, (C₁~ C_FourAlkylamino) carbonyl or di (C₁~ C_FourAlkyl)
Represents aminocarbonyl) or R⁷And R⁸Are united into one to four C₁~ C_FourAn alkyl group, or one or two
(C₁~ C_Four1,3-propyl which may have an alkoxy) carbonyl group
Forms a len, tetramethylene, pentamethylene or ethyleneoxyethylene chain
3- (benzoazol-4-yl) pyrimidinedione derivative represented by the formula:
Agriculturally useful salts of Compound I. 2. X represents oxygen, R¹Is hydrogen, amino or C₁~ C₆Represents alkyl, R^TwoIs hydrogen, halogen, C₁~ C₆Alkyl, C₁~ C₆Haloalkyl or C₁~ C ₆ R represents alkylsulfonyl,^ThreeRepresents hydrogen, R^FourRepresents hydrogen, fluorine or chlorine;^FiveRepresents cyano or halogen;⁶Is C₁~ C₆Alkyl, C_Three~ C₆Alkynyl, C₁~ C₆Alkylsulfonyl or (C₁~ C₆3. The 3-(-) of formula I according to claim 1, which represents (alkoxy) carbonyl.
Benzoazol-4-yl) pyrimidinedione derivatives. 3. Use of the 3- (benzoazol-4-yl) pyrimidinedione derivative I according to claim 1 or an agriculturally useful salt thereof as a herbicide. 4. A herbicidally effective amount of at least one of the formula I according to claim 1.
At least one liquid and / or solid carrier, and optionally at least one salt of 3- (benzoazol-4-yl) pyrimidinedione derivative or I
A herbicidal composition comprising a surfactant. 5. A herbicidally effective amount of at least one of the formula I according to claim 1.
At least one liquid and / or solid carrier, and optionally at least one salt of 3- (benzoazol-4-yl) pyrimidinedione derivative or I
A method for producing a herbicidally active composition, comprising mixing two kinds of surfactants. 6. A herbicidally effective amount of at least one of the formula I according to claim 1.
Species of 3- (benzoazol-4-yl) pyrimidinedione derivatives or salts of I
A method for controlling undesired vegetation on a plant, its environment or seeds. 7. A compound of the formula III: Wherein L ² represents C ₁ -C ₄ alkyl or phenyl, and R ¹ -R ⁵ and Y are as defined in claim 1. 8. A compound of formula IV: Wherein L ² represents C ₁ -C ₄ alkyl or phenyl, and R ¹ -R ⁵ and Y have the same meanings as in claim 1. 9. A compound of the formula V: [Wherein the symbols X and R ^{1 to} R ⁶ have the same meanings as in claim 1]. 2-substituted 2-aminophenol, 2-thiophenol or 2-aniline.