KR20010033195A - Herbicides 3-(Benzazol-4-yl)Pyrimidine-Dione-Derivatives - Google Patents

Abstract

Novel 3- (benzazol-4-yl) pyrimidinedione derivatives of formula I and agriculturally useful salts of formula I.

<Formula I>

Where

X is hydrogen or sulfur;

R ¹ is hydrogen, amino, C ₁ -C ₆ alkyl or C ₁ -C ₆ -haloalkyl;

R ² is hydrogen, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, or C ₁ -C ₆ alkylsulfonyl;

R ³ is hydrogen, halogen or C ₁ -C ₆ alkyl;

R ⁴ is hydrogen or halogen;

R ⁵ is cyano, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₆ haloalkoxy;

= Y- is a group = NN (R ⁶ )-, = C (ZR ⁷ ) -N (R ⁶ )-, = C (ZR ⁷ ) -O- or = C (ZR ⁷ ) -S-;

R ⁶ is C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkylsulfonyl , (C ₁ -C ₆ alkyl) carbonyl, (C ₁ -C ₆ haloalkyl) carbonyl, (C ₁ -C ₆ alkyl) thiocarbonyl, (C ₁ -C ₆ alkoxy) carbonyl, (C ₁ -C ₆ alkoxy) thiocarbonyl, or cyano, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, (C ₁ -C ₆ alkoxy) carbonyl, (C ₁ -C ₆ alkylamino) carbonyl , a di (C ₁ -C ₆ alkyl) aminocarbonyl or (C ₁ -C ₆ alkyl) carbonyloxy C ₁ -C ₆ alkyl optionally substituted with,

Z is a chemical bond, oxygen, sulfur, -S (O)-,-S (O) _2- , -NH- or -N (R ⁸ )-;

R ⁷ and R ⁸ are independently

C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, hydroxy-C ₁ -C ₄ alkyl, cyano-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkoxy-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenyloxy-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkynyloxy-C ₁ -C ₄ alkyl, C ₃ -C ₈ cycloalkoxy-C ₁ -C ₄ alkyl,

Amino-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylamino-C ₁ -C ₄ alkyl, di (C ₁ -C ₄ alkyl) amino-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylthio- C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkylthio-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenylthio-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkynylthio-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylsulfinyl-C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkylsulfinyl-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenylsulfinyl-C _1- C ₄ alkyl, C ₃ -C ₄ alkynylsulfinyl-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylsulfonyl-C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkylsulfonyl-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenylsulfonyl-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkynylsulfonyl-C ₁ -C ₄ alkyl, C ₃ -C ₆ alkenyl, cyano-C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, cyano-C ₃ -C ₆ alkynyl, C ₃ -C ₆ haloalkynyl, hydroxycarbonyl-C ₁ -C ₄ alkyl, (C ₁ -C ₄ alkoxy) carbonyl-C ₁ -C ₄ alkyl, (C ₁ -C ₄ alkylthio) carbonyl-C ₁ -C ₄ alkyl, aminocarbonyl-C ₁ -C ₄ alkyl , (C ₁ -C ₄ alkyl, O No) carbonyl -C ₁ -C ₄ alkyl, di (C ₁ -C ₄ alkyl) amino carbonyl -C ₁ -C ₄ alkyl, di (C ₁ -C ₄ alkyl) -C ₁ -C ₄ alkyl sulfonyl Force , C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkyl-C ₁ -C ₄ alkyl, phenyl, phenyl-C ₁ -C ₄ alkyl, 3- to 7-membered heterocyclyl or heterocyclyl-C ₁ -C ₄ alkyl (each heterocyclyl ring may comprise a carbonyl or thiocarbonyl ring member),

Wherein each cycloalkyl, phenyl and heterocyclyl ring may be unsubstituted or attached with 1 to 4 substituents, where each substituent is cyano, nitro, amino, hydroxyl, carboxyl, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C _1- C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, (C ₁ -C ₄ alkoxy) carbonyl, (C ₁ -C ₄ alkyl) carbonyl, (C ₁ -C ₄ haloalkyl) carbonyl, (C ₁ -C ₄ alkyl) carbonyloxy, (C ₁ -C ₄ haloalkyl) carbonyloxy and di (C ₁ -C ₄ alkyl) amino, or

Or, if Z is a chemical bond, then R ⁷ , if desired, is also hydrogen, hydroxy, cyano, mercapto, amino, halogen, -CH (OH) -CH ₂ -R ⁹ , -CH (halogen) -CH _2- R ⁹ , -CH ₂ -CH (halogen) -R ⁹ , -CH = CH-R ⁹ or -CH = C (halogen) -R ⁹ , wherein R ⁹ is hydroxycarbonyl, (C ₁ -C ₄ Alkoxy) carbonyl, (C ₁ -C ₄ alkylthio) carbonyl, aminocarbonyl, (C ₁ -C ₄ alkylamino) carbonyl or di (C ₁ -C ₄ alkyl) aminocarbonyl),

Or R ⁷ and R ⁸ together are 1,3-propylene, tetra, unsubstituted or attached with 1 to 4 C ₁ -C ₄ alkyl groups or one or two (C ₁ -C ₄ alkoxy) carbonyl groups, respectively; Methylene, pentamethylene or ethyleneoxyethylene chains.

Description

Herbicide 3- (benzazol-4-yl) pyrimidinedione derivatives {Herbicides 3- (Benzazol-4-yl) Pyrimidine-Dione-Derivatives}

The present invention relates to novel 3- (benzazol-4-yl) pyrimidinedione derivatives of formula (I) and agriculturally useful salts of formula (I).

Where

X is hydrogen or sulfur;

R ¹ is hydrogen, amino, C ₁ -C ₆ alkyl or C ₁ -C ₆ -haloalkyl;

R ² is hydrogen, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, or C ₁ -C ₆ alkylsulfonyl;

R ³ is hydrogen, halogen or C ₁ -C ₆ alkyl;

R ⁴ is hydrogen or halogen;

R ⁵ is cyano, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₆ haloalkoxy;

= Y- is a group = NN (R ⁶ )-, = C (ZR ⁷ ) -N (R ⁶ )-, = C (ZR ⁷ ) -O- or = C (ZR ⁷ ) -S-;

R ⁶ is C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkylsulfonyl , (C ₁ -C ₆ alkyl) carbonyl, (C ₁ -C ₆ haloalkyl) carbonyl, (C ₁ -C ₆ alkyl) thiocarbonyl, (C ₁ -C ₆ alkoxy) carbonyl, (C ₁ -C ₆ alkoxy) thiocarbonyl, or cyano, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, (C ₁ -C ₆ alkoxy) carbonyl, (C ₁ -C ₆ alkylamino) carbonyl , a di (C ₁ -C ₆ alkyl) aminocarbonyl or (C ₁ -C ₆ alkyl) carbonyloxy C ₁ -C ₆ alkyl optionally substituted with,

Z is a chemical bond, oxygen, sulfur, -S (O)-,-S (O) _2- , -NH- or -N (R ⁸ )-;

R ⁷ and R ⁸ are independently

C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, hydroxy-C ₁ -C ₄ alkyl, cyano-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkoxy-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenyloxy-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkynyloxy-C ₁ -C ₄ alkyl, C ₃ -C ₈ cycloalkoxy-C ₁ -C ₄ alkyl,

Amino-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylamino-C ₁ -C ₄ alkyl, di (C ₁ -C ₄ alkyl) amino-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylthio- C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkylthio-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenylthio-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkynylthio-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylsulfinyl-C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkylsulfinyl-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenylsulfinyl-C _1- C ₄ alkyl, C ₃ -C ₄ alkynylsulfinyl-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylsulfonyl-C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkylsulfonyl-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenylsulfonyl-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkynylsulfonyl-C ₁ -C ₄ alkyl, C ₃ -C ₆ alkenyl, cyano-C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, cyano-C ₃ -C ₆ alkynyl, C ₃ -C ₆ haloalkynyl, hydroxycarbonyl-C ₁ -C ₄ alkyl, (C ₁ -C ₄ alkoxy) carbonyl-C ₁ -C ₄ alkyl, (C ₁ -C ₄ alkylthio) carbonyl-C ₁ -C ₄ alkyl, aminocarbonyl-C ₁ -C ₄ alkyl , (C ₁ -C ₄ alkyl, O No) carbonyl -C ₁ -C ₄ alkyl, di (C ₁ -C ₄ alkyl) amino carbonyl -C ₁ -C ₄ alkyl, di (C ₁ -C ₄ alkyl) -C ₁ -C ₄ alkyl sulfonyl Force , C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkyl-C ₁ -C ₄ alkyl, phenyl, phenyl-C ₁ -C ₄ alkyl, 3- to 7-membered heterocyclyl or heterocyclyl-C ₁ -C ₄ alkyl (each heterocyclyl ring may comprise a carbonyl or thiocarbonyl ring member),

Wherein each cycloalkyl, phenyl and heterocyclyl ring may be unsubstituted or attached with 1 to 4 substituents, where each substituent is cyano, nitro, amino, hydroxyl, carboxyl, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C _1- C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, (C ₁ -C ₄ alkoxy) carbonyl, (C ₁ -C ₄ alkyl) carbonyl, (C ₁ -C ₄ haloalkyl) carbonyl, (C ₁ -C ₄ alkyl) carbonyloxy, (C ₁ -C ₄ haloalkyl) carbonyloxy and di (C ₁ -C ₄ alkyl) amino, and

Or, if Z is a chemical bond, then R ⁷ , if desired, is also hydrogen, hydroxy, cyano, mercapto, amino, halogen, -CH (OH) -CH ₂ -R ⁹ , -CH (halogen) -CH _2- R ⁹ , -CH ₂ -CH (halogen) -R ⁹ , -CH = CH-R ⁹ or -CH = C (halogen) -R ⁹ , wherein R ⁹ is hydroxycarbonyl, (C ₁ -C ₄ alkoxy) carbonyl, (C ₁ -C ₄ alkylthio) carbonyl, aminocarbonyl, (C ₁ -C ₄ alkylamino) carbonyl or di (C ₁ -C ₄ alkyl) aminocarbonyl),

Or R ⁷ and R ⁸ together are 1,3-propylene, tetra, unsubstituted or attached with 1 to 4 C ₁ -C ₄ alkyl groups or one or two (C ₁ -C ₄ alkoxy) carbonyl groups, respectively; Methylene, pentamethylene or ethyleneoxyethylene chains.

In addition, the present invention

The use of a compound of formula I as a herbicide,

Herbicide compositions containing a compound of formula I as active substance,

A process for preparing a compound of formula I and a method for preparing a herbicide composition using a compound of formula I,

To control unnecessary plants with a compound of formula I, and

-Intermediates of formulas (III), (IV) and (V) for the preparation of compounds of formula

WO 97/08170 describes certain 3- (benzox / benzothiazol-7-yl) -6- (trifluoromethyl) uracil as herbicides. Other uses of 3- (benzothiazol-7-yl) uracil and herbicides, as well as the use of plants for drying / foliage, are taught in WO97 / 08171. WO97 / 12886 is the subject of certain 3-benzisoxazol-7-yl-2,4- (1H, 3H) pyrimidinediones known to have herbicidal and dry activity.

It is an object of the present invention to provide novel herbicidally active uracil compounds which allow for targeted regulation of unnecessary plants that are improved over known compounds.

The object of the present invention is achieved by the compound of formula I 3- (benzazol-4-yl) pyrimidinedione.

In addition, herbicide compositions containing compounds of formula (I) and having very good herbicidal activity have been found. Moreover, methods for preparing these compounds and methods for controlling unnecessary plants with Compound I have been found.

Depending on the substitution pattern, the compound of formula (I) may have one or more chiral centers which may exist as a mixture of enantiomers or diastereomers. If compound I has one or more olefinic radicals, E / Z isomers may also be possible. The present invention also relates to pure enantiomers or diastereomers and mixtures thereof.

Formula I represents only one possible version of some of the compounds according to the invention. Thus, for example, a compound I in which R ⁷ = hydroxy may be described as tautomer I '[-N = C (OH)-> → -NH-CO-].

Among the agriculturally useful salts suitable are mainly salts of these cations or acid addition salts of these acids (the cations or anions do not adversely affect the herbicidal activity of compound I, respectively). Thus, suitable cations are in particular ions of alkali metals (preferably sodium, potassium), alkaline earth metals (preferably calcium, magnesium and barium), and transition metals (preferably manganese, copper, zinc and iron), The ammonium ions may also have 1 to 4 C ₁ -C ₄ alkyl substituents and / or phenyl or benzyl substituents attached to the ammonium ions if desired, preferably diisopropylammonium, tetramethylammonium, tetrabutyl Ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C ₁ -C ₄ alkyl) sulfonium and sulfoxnium ions, preferably tri (C ₁ -C ₄ alkyl) sulfonium to be.

Anions of useful acid addition salts are mainly chlorides, bromides, florides, hydrogen sulfates, sulfates, dihydrogen phosphates, hydrogen phosphates, phosphates, nitrates, hydrogen carbonates, carbonates, hexafluorosilicates, hexafluoro Phosphates, benzoates, and anions of the C ₁ -C ₄ alkanoic acid (preferably formate, acetate, propionate and butyrate). They can be produced by reacting compound I with an acid of the corresponding anion (preferably hydrochloric acid, bromic acid, sulfuric acid, phosphoric acid or nitric acid).

The organic moieties (similar to the meaning of halogen) in the definitions of substituents R ¹ to R ³ and R ⁵ to R ⁹ or as radicals of a cycloalkyl, phenyl or heterocyclic ring are generic to the individual enumeration of the individual group members. Indicates a term. All carbon chains, ie all alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, aminoalkyl, hydroxycarbonylalkyl, aminocarbonylalkyl, phenylalkyl, heterocyclylalkyl, alkoxy, haloalkoxy, alkylthio, Haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkenyl, haloalkenyl, cyanoalkenyl, alkenyloxy, alkenylthio, alkenylsulfinyl, alkenylsulfonyl, alky Neyl, haloalkynyl, cyanoalkynyl, alkynyloxy, alkynylthio, alkynylsulfinyl and alkynylsulfonyl groups are straight or branched chains. Halogenated substituents preferably have one to five identical or different halogen atoms attached thereto. Halogen means in each case fluorine, chlorine, bromine or iodine.

Other meanings are for example:

-C ₁ -C ₄ alkyl: CH ₃ , C ₂ H ₅ , CH ₂ -C ₂ H ₅ , CH (CH ₃ ) ₂ , n-butyl, CH (CH ₃ ) -C ₂ H ₅ , CH ₂ -CH (CH ₃ ) ₂ or C (CH ₃ ) ₃ ;

-C ₁ -C ₄ haloalkyl: C ₁ -C ₄ alkyl radicals as mentioned above partially or completely substituted with fluorine, chlorine, bromine and / or iodine, for example CH ₂ F, CHF ₂ , CF ₃ , CH ₂ Cl, CH (Cl) ₂ , C (Cl) ₃ , chlorofluoromethyl, dichlorofluoromethyl, clodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromo Ethyl, 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 ₂ F ₅ , 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-trichloropropyl, CH ₂ -C ₂ F ₅ , CF ₂ -C ₂ F ₅ , 1- (fluoromethyl) -2-fluoro Methyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;

-C ₁ -C ₆ alkyl: -C ₁ -C ₄ alkyl as mentioned above, for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl , 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl , 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 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 ₃ , C ₂ H ₅ , CH ₂ -C ₂ H ₅ , CH (CH ₃ ) ₂ , n-butyl, C (CH ₃ ) ₃ , n-pentyl or n-hexyl;

-C ₁ -C ₆ haloalkyl: a C ₁ -C ₄ alkyl radical as mentioned above partially or wholly substituted with fluorine, chlorine, bromine and / or iodine, for example C ₁ -C ₄ halo Alkyl or 5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, Udekafluoropentyl, 6-fluoro-1-hexyl, 6-chloro-1-hexyl, 6-bromo-1-hexyl, 6-iodo-1-hexyl, 6,6,6-trichloro- One of the radicals referred to as 1-hexyl or dodecafluorohexyl;

-Cyano-C ₁ -C ₄ alkyl: CH ₂ CN, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cya Noprop-1-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl, 1-sia Nobut-2-yl, 2-cyanobut-2-yl, 3-cyanobut-2-yl, 4-cyanobut-2-yl, 1- (CH ₂ CN) eth-1-yl, 1- (CH ₂ CN) -1- (CH ₃ ) -eth-1-yl or 1- (CH ₂ CN) prop-1-yl;

-Hydroxy -C ₁ -C ₄ alkyl: CH ₂ OH, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxy-prop-1-yl, 2-hydroxy-prop-1-yl, 3 -Hydroxyprop-1-yl, 1-hydroxybut-1-yl, 2-hydroxybut-1-yl, 3-hydroxybut-1-yl, 4-hydroxybut-1-yl, 1-hydroxybut-2-yl, 2-hydroxybut-2-yl, 3-hydroxybut-2-yl, 4-hydroxybut-2-yl, 1- (CH ₂ OH) eth-1 -Yl, 1- (CH ₂ OH) -1- (CH ₃ ) -eth-1-yl, 1- (CH ₂ OH) prop-1-yl;

-Amino-C ₁ -C ₄ alkyl: CH ₂ NH ₂ , 1-aminoethyl, 2-aminoethyl, 1-aminoprop-1-yl, 2-aminoprop-1-yl, 3-aminoprop -1-yl, 1-aminobut-1-yl, 2-aminobut-1-yl, 3-aminobut-1-yl, 4-aminobut-1-yl, 1-aminobut-2-yl, 2-aminobut-2-yl, 3-aminobut-2-yl, 4-aminobut-2-yl, 1- (CH ₂ NH ₂ ) eth-1-yl, 1- (CH ₂ NH ₂ )- 1- (CH ₃ ) -eth-1-yl, 1- (CH ₂ NH ₂ ) prop-1-yl;

-Hydroxy carbonyl -C ₁ -C _{4 alkyl: CH 2 COOH, 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- (COOH) but-1-yl, 4- (COOH) but-1-yl, 1- (COOH) but-2-yl, 2- (COOH) but-2-yl, 3- (COOH) but-2-yl, 4- (COOH) but 2-yl, 1- (CH ₂ COOH) eth-1-yl, 1- (CH ₂ COOH) -1- (CH ₃ ) -eth-1-yl, 1- (CH ₂ COOH) prop-1 -Work;

-Aminocarbonyl-C ₁ -C ₄ alkyl: CH ₂ CONH ₂ , 1- (CONH ₂ ) ethyl, 2- (CONH ₂ ) ethyl, 1- (CONH ₂ ) prop-1-yl, 2- (CONH ₂ ) prop-1-yl, 3- (CONH ₂ ) prop-1-yl, 1- (CONH ₂ ) but-1-yl, 2- (CONH ₂ ) but-1-yl, 3- (CONH ₂ ) but-1-yl, 4- (CONH ₂ ) but-1-yl, 1- (CONH ₂ ) but- ₂ -yl, 2- (CONH ₂ ) but- ₂ -yl, 3- (CONH ₂ ) But-2-yl, 4- (CONH ₂ ) but- ₂ -yl, 1- (CH ₂ CONH ₂ ) eth-1-yl, 1- (CH ₂ CONH ₂ ) -1- (CH ₃ ) -et- 1-yl, 1- (CH ₂ CONH ₂ ) prop-1-yl;

-Phenyl-C ₁ -C ₄ alkyl: benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1- 1, 1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenyl But-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1- (benzyl) eth-1-yl, 1- (benzyl) -1- (CH ₃ ) -eth- 1-yl, 1- (benzyl) prop-1-yl, preferably benzyl or 2-phenylethyl;

-Heterocyclyl-C ₁ -C ₄ alkyl: heterocyclylmethyl, 1-heterocyclylethyl, 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-heterocyclylbut-2-yl, 2-heterocyclylbut-2-yl, 3-heterocyclylbut-2-yl, 4-heterocyclylbut 2-yl, 1- (heterocyclylmethyl) eth-1-yl, 1- (heterocyclylmethyl) -1- (CH ₃ ) -eth-1-yl, 1- (heterocyclylmethyl) pro P-1-yl, preferably heterocyclylmethyl or 2-heterocyclylethyl;

-C ₁ -C ₄ alkoxy: OCH ₃ , OC ₂ H ₅ , OCH ₂ -C ₂ H ₅ , OCH (CH ₃ ) ₂ , n-butoxy, OCH (CH ₃ ) -C ₂ H ₅ , OCH _2- CH (CH ₃ ) ₂ or C (CH ₃ ) ₃ , preferably OCH ₃ , OC ₂ H ₅ or OCH (CH ₃ ) ₂ ;

-C ₁ -C ₄ haloalkoxy: a C ₁ -C ₄ alkoxy radical as described above partially or completely substituted with fluorine, chlorine, bromine and / or iodine, eg. OCH ₂ F, OCHF ₂ , OCF ₃ , OCH ₂ Cl, OCH (Cl) ₂ , OC (Cl) ₃ , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 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-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC ₂ F ₅ , 2-fluoropropoxy , 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2- Bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH ₂ -C ₂ F ₅ , OCF ₂ -C ₂ F ₅ , 1- (CH ₂ F) -2-fluoroethoxy, 1- (CH ₂ Cl) -2-chloroethoxy, 1- (CH ₂ Br) -2-bromoethoxy, 4-fluorobutoxy , 4-chlorobutoxy, 4-bro Butoxy or ethoxy unit nonafluorobutyl, preferably OCH ₂ F, OCF _3, dichloro difluoromethoxy, chloro-difluoromethoxy-ethoxy or 2,2,2-trifluoroethyl;

-C ₁ -C ₆ alkoxy: C ₁ -C ₄ alkoxy radicals as described above, or for example n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2, 2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy , 4-methylpentoxy, 1,1-dimethylbutoxy, 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 ₃ , OC ₂ H ₅ , OCH ₂ -C ₂ H ₅ , OCH (CH ₃ ) ₂ , n-butoxy, OC (CH ₃ ) ₃ , n-pentoxy, n-hexoxy;

-C ₁ -C ₆ haloalkoxy: as mentioned above in the C ₁ -C ₆ alkoxy radical, ie C ₁ -C ₄ haloalkoxy, partially or completely substituted with fluorine, chlorine, bromine and / or iodine One of the radicals or 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5,5,5-trichloro Rho-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;

-C ₁ -C ₄ alkylthio: SCH ₃ , SC ₂ H ₅ , SCH ₂ -C ₂ H ₅ , SCH (CH ₃ ) ₂ , n-butylthio, SCH (CH ₃ ) -C ₂ H ₅ , SCH ₂ -CH (CH ₃ ) ₂ or SC (CH ₃ ) ₃ , preferably SCH ₃ , or SC ₂ H ₅ ;

-C ₁ -C ₄ haloalkylthio: a C ₁ -C ₄ alkylthio radical as described above partially or completely substituted with fluorine, chlorine, bromine and / or iodine, eg. SCH ₂ F, SCHF ₂ , SCF ₃ , SCH ₂ Cl, SCH (Cl) ₂ , SC (Cl) ₃ , chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethyl Thio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2- Fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, SC ₂ F ₅ , 2- Fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropyl Thio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, SCH ₂ -C ₂ F ₅ , SCF _2- C ₂ F ₅ , 1- (CH ₂ F) -2-fluoroethylthio, 1- (CH ₂ Cl) -2-chloroethylthio, 1- (CH ₂ Br)- 2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or SCF ₂ -CF ₂ -C ₂ F ₅ , preferably SCH ₂ F, SCF ₃ , dichlorofluoro Chloromethylthio, chlorodifluoromethylthio or 2,2,2-trifluoroethylthio;

-C ₁ -C ₆ alkylthio: a C ₁ -C ₄ alkylthio radical as described above, or for example n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methyl Pentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3 , 3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1 -Ethyl-2-methylpropylthio, preferably SCH ₃ , SC ₂ H ₅ , SCH ₂ -C ₂ H ₅ , SCH (CH ₃ ) ₂ , n-butylthio, SCH (CH ₃ ) ₃ , n-pentyl Thio, n-hexylthio;

-C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl: C ₁ -C ₄ alkyl substituted with C ₁ -C ₄ alkoxy as described above, eg. CH ₂ -OCH ₃ , CH ₂ -OC ₂ H ₅ , n-propoxymethyl, CH ₂ -OCH (CH ₃ ) ₂ , n-butoxymethyl, (1-methylpropoxy) methyl, (2-methylprop Foxy) methyl, CH ₂ -OC (CH ₃ ) ₃ , 2- (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- (meth Methoxy) propyl, 2- (ethoxy) propyl, 2- (n-propoxy) propyl, 2- (1-methylethoxy) propyl, 2- (n-butoxy) propyl, 2- (1-methylprop Foxy) propyl, 2- (2-methylpropoxy) propyl, 2- (1,1-dimethylethoxy) propyl, 3- (methoxy) propyl, 3- (ethoxy) propyl, 3- (n-prop Foxy) propyl, 3- (1-methylethoxy) propyl, 3- (n-butoxy) propyl, 3- (1-methylpropoxy) propyl, 3- (2-methylpropoxy) propyl, 3- ( 1,1-dimethylethoxy) propyl, 2- (methoxy) butyl, 2- (ethoxy) butyl, 2- (n-propoxy) butyl, 2- (1-methylethoxy) butyl, 2- ( n-butoxy) butyl, 2- (1- Methylpropoxy) 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-methylpropoxy) butyl, 3 -(1,1-dimethylethoxy) butyl, 4- (methoxy) butyl, 4- (ethoxy) butyl, 4- (n-propoxy) butyl, 4- (1-methylethoxy) butyl, 4 -(n-butoxy) butyl, 4- (1-methylpropoxy) butyl, 4- (2-methylpropoxy) butyl, 4- (1,1-dimethylethoxy) butyl, preferably CH _2- OCH ₃ , CH ₂ -OC ₂ H ₅ , 2- (OCH ₃ ) ethyl or 2- (OC ₂ H ₅ ) ethyl;

-C ₁ -C ₄ haloalkoxy, -C ₁ -C ₄ alkyl: substituted by C ₁ -C ₄ haloalkoxy group as described above, -C ₁ -C ₄ alkyl, e. 2- (OCHF ₂ ) ethyl, 2- (OCF ₃ ) ethyl or 2- (OC ₂ F ₅ ) ethyl;

-C ₁ -C ₄ alkylthio -C ₁ -C ₄ alkyl: substituted by C ₁ -C ₄ alkylthio as described above, -C ₁ -C ₄ alkyl, e. CH ₂ -SCH ₃ , CH ₂ -SC ₂ H ₅ , n-propylthiomethyl, CH ₂ -SCH (CH ₃ ) ₂ , n-butylthiomethyl, (1-methylpropylthio) methyl, (2-methylpropyl Thio) methyl, CH ₂ -SC (CH ₃ ) ₃ , 2- (methylthio) ethyl, 2- (ethylthio) ethyl, 2- (n-propylthio) ethyl, 2- (1-methylethylthio) ethyl , 2- (n-butylthio) ethyl, 2- (1-methylpropylthio) ethyl, 2- (2-methylpropylthio) ethyl, 2- (1,1-dimethylethylthio) ethyl, 2- (methyl Thio) propyl, 2- (ethylthio) propyl, 2- (n-propylthio) propyl, 2- (1-methylethylthio) propyl, 2- (n-butylthio) propyl, 2- (1-methylpropyl Thio) propyl, 2- (2-methylpropylthio) propyl, 2- (1,1-dimethylethylthio) propyl, 3- (methylthio) propyl, 3- (ethylthio) propyl, 3- (n-propyl Thio) 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) Tyl, 2- (propylthio) butyl, 2- (1-methylethylthio) butyl, 2- (n-butylthio) butyl, 2- (1-methylpropylthio) butyl, 2- (2-methylpropylthio ) Butyl, 2- (1,1-dimethylethylthio) butyl, 3- (methylthio) butyl, 3- (ethylthio) butyl, 3- (n-propylthio) butyl, 3- (1-methylethylthio ) Butyl, 3- (n-butylthio) butyl, 3- (1-methylpropylthio) butyl, 3- (2-methylpropylthio) butyl, 3- (1,1-dimethylethylthio) butyl, 4- (Methylthio) butyl, 4- (ethylthio) butyl, 4- (n-propylthio) butyl, 4- (1-methylethylthio) butyl, 4- (n-butylthio) butyl, 4- (1- Methylpropylthio) butyl, 4- (2-methylpropylthio) butyl, 4- (1,1-dimethylethylthio) butyl, preferably CH ₂ -SCH ₃ , CH ₂ -SC ₂ H ₅ , 2- ( SCH ₃ ) ethyl or 2- (SC ₂ H ₅ ) ethyl;

-C ₁ -C ₄ haloalkylthio-C ₁ -C ₄ alkyl: C ₁ -C ₄ alkyl substituted with C ₁ -C ₄ haloalkylthio as described above, eg, 2- (SCHF ₂ ) ethyl, 2 -(SCF ₃ ) ethyl or 2- (SC ₂ F ₅ ) ethyl;

- (C ₁ -C ₄ alkyl) _{carbonyl: CO-CH 3, CO-} C 2 H 5, CO-CH 2 -C 2 H 5, CO-CH (CH 3) 2, n- butyl-carbonyl, CO -CH (CH ₃ ) -C ₂ H ₅ , CO-CH ₂ -CH (CH ₃ ) ₂ or CO-C (CH ₃ ) ₃ , preferably CO-CH ₃ or CO-C ₂ H ₅ ;

— (C ₁ -C ₄ haloalkyl) carbonyl: (C ₁ -C ₄ alkyl) carbonyl radicals partially or fully substituted with fluorine, chlorine, bromine and / or iodine as described above, eg. CO-CH ₂ F, CO-CHF ₂ , CO-CF ₃ , CO-CH ₂ Cl, CO-CH (Cl) ₂ , CO-C (Cl) ₃ , chlorofluoromethylcarbonyl, dichlorofluoromethylcar Carbonyl, chlorodifluoromethylcarbonyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbon Carbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2- Fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, CO-C ₂ F ₅ , 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-difluoropropylcarbone Carbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbone Carbonyl, 3,3,3-trifluoropropylcarbonyl, 3,3,3- Lee _{chloropropyl-carbonyl, CO-CH 2 -C 2 F} 5, CO-CF 2 -C 2 F 5, 1- (CH 2 F) 2-fluoro-ethyl-carbonyl, 1- (CH ₂ Cl) - 2-chloroethylcarbonyl, 1- (CH ₂ Br) -2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or nonafluorobutyl Carbonyl, preferably CO-CF ₃ , CO-CH ₂ Cl or 2,2,2-trifluoroethylcarbonyl;

— (C ₁ -C ₆ alkyl) carbonyl: one of the aforementioned (C ₁ -C ₄ alkyl) carbonyl radicals or for example n-pentyl-CO, 1-methylbutyl-CO, 2-methylbutyl- 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-methylpentyl-CO, 3-methylpentyl-CO, 4-methylpentyl-CO, 1,1-dimethylbutyl-CO, 1,2-dimethylbutyl-CO, 1,3-dimethyl Butyl-CO, 2,2-dimethylbutyl-CO, 2,3-dimethylbutyl-CO, 3,3-dimethylbutyl-CO, 1-ethylbutyl-CO, 2-ethylbutyl-CO, 1,1,2 -Trimethylpropyl-CO, 1,2,2--trimethylpropyl-CO, 1-ethyl-1-methylpropyl-CO, 1-ethyl-2-methylpropyl-CO, preferably CO-CH ₃ , CO -C ₂ H ₅ , CO-CH ₂ -C ₂ H ₅ , CO-CH (CH ₃ ) ₂ , n-butyl-CO, CO-C (CH ₃ ) ₃ , CO- (nC ₅ H ₁₁ ) or CO -(nC ₆ H ₁₃ );

-(C ₁ -C ₆ haloalkyl) carbonyl: (C ₁ -C ₆ alkyl) carbonyl rest, partially or fully substituted with fluorine, chlorine, bromine and / or iodine as described above, eg . CO-CH ₂ F, CO-CHF ₂ , CO-CF ₃ , CO-CH ₂ Cl, CO-CH (Cl) ₂ , CO-C (Cl) ₃ , chlorofluoromethylcarbonyl, dichlorofluoromethylcar Carbonyl, chlorodifluoromethylcarbonyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbon Carbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2- Fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, CO-C ₂ F ₅ , 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-difluoropropylcarbone Carbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbone Carbonyl, 3,3,3-trifluoropropylcarbonyl, 3,3,3- Lee _{chloropropyl-carbonyl, CO-CH 2 -C 2 F} 5, CO-CF 2 -C 2 F 5, 1- (CH 2 F) 2-fluoro-ethyl-carbonyl, 1- (CH ₂ Cl) - 2-chloroethylcarbonyl, 1- (CH ₂ Br) -2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or nonafluorobutyl Carbonyl, preferably CO-CF ₃ , CO-CH ₂ Cl or 2,2,2-trifluoroethylcarbonyl;

- (C ₁ -C ₄ alkyl) _{carbonyloxy: O-CO-CH 3,} O-CO-C 2 H 5, O-CO-CH 2 -C 2 H 5, O-CO-CH (CH 3) ₂ , O-CO-CH ₂ -CH ₂ -C ₂ H ₅ , O-CO-CH (CH ₃ ) -C ₂ H ₅ , O-CO-CH ₂ -CH (CH ₃ ) ₂ or O-CO- C (CH ₃ ) ₃ , preferably O—CO—CH ₃ or O—CO—C ₂ H ₅ ;

— (C ₁ -C ₄ haloalkyl) carbonyloxy: (C ₁ -C ₄ alkyl) carbonyl radicals partially or fully substituted with fluorine, chlorine, bromine and / or iodine as described above, eg. O-CO-CH ₂ F, O-CO-CHF ₂ , O-CO-CF ₃ , O-CO-CH ₂ Cl, O-CO-CH (Cl) ₂ , O-CO-C (Cl) ₃ , Chlorofluoromethylcarbonyloxy, dichlorofluoromethylcarbonyloxy, chlorodifluoromethylcarbonyloxy, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy, 2-bromoethylcarbonyloxy , 2-iodoethylcarbonyloxy, 2,2-difluoroethylcarbonyloxy, 2,2,2-trifluoroethylcarbonyloxy, 2-chloro-2-fluoroethylcarbonyloxy, 2 -Chloro-2,2-difluoroethylcarbonyloxy, 2,2-dichloro-2-fluoroethylcarbonyloxy, 2,2,2-trichloroethylcarbonyloxy, O-CO-C ₂ F ₅ , 2-fluoropropylcarbonyloxy, 3-fluoropropylcarbonyloxy, 2,2-difluoropropylcarbonyloxy, 2,3-difluoropropylcarbonyloxy, 2-chloropropylcarbonyl Oxy, 3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbono Nyloxy, 2-bromopropylcarbonyloxy, 3-bromopropylcarbonyloxy, 3,3,3-trifluoropropylcarbonyloxy, 3,3,3-trichloropropylcarbonyloxy, O- CO-CH ₂ -C ₂ F ₅ , O-CO-CF ₂ -C ₂ F ₅ , 1- (CH ₂ F) -2-fluoroethylcarbonyloxy, 1- (CH ₂ Cl) -2-chloro Ethylcarbonyloxy, 1- (CH ₂ Br) -2-bromoethylcarbonyloxy, 4-fluorobutylcarbonyloxy, 4-chlorobutylcarbonyloxy, 4-bromobutylcarbonyloxy or nonafluor Robutylcarbonyloxy, preferably O-CO-CF ₃ , O-CO-CH ₂ Cl or 2,2,2-trifluoroethylcarbonyloxy;

— (C ₁ -C ₆ alkyl) carbonyloxy: one of the aforementioned (C ₁ -C ₄ alkyl) carbonyloxy radicals or for example n-pentyl-COO, 1-methylbutyl-COO, 2-methyl Butyl-COO, 3-methylbutyl-COO, 2,2-dimethylpropyl-COO, 1-ethylpropyl-COO, n-hexyl-COO, 1,1-dimethylpropyl-COO, 1,2-dimethylpropyl-COO , 1-methylpentyl-COO, 2-methylpentyl-COO, 3-methylpentyl-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-dimethylbutyl-COO, 1-ethylbutyl-COO, 2-ethylbutyl-COO, 1,1 , 2-trimethylpropyl-COO, 1,2,2-trimethylpropyl-COO, 1-ethyl-1-methylpropyl-COO, or 1-ethyl-2-methylpropyl-COO, preferably O-CO-CH ₃ , O-CO-C ₂ H ₅ , O-CO-CH ₂ -C ₂ H ₅ , O-CO-CH (CH ₃ ) ₂ , n-butyl-COO, O-CO-C (CH ₃ ) ₃ , O-CO- (nC ₅ H ₁₁ ) or O-CO- (nC ₆ H ₁₃ );

- (C ₁ -C ₆ alkyl) _{thiocarbonyl: CS-CH 3, CS-} C 2 H 5, CS-CH 2 -C 2 H 5, CS-CH (CH 3) 2, CS- (nC 4 H ₉ ), CS-CH (CH ₃ ) -C ₂ H ₅ , CS-CH ₂ -CH (CH ₃ ) ₂ , CS-C (CH ₃ ) ₃ , CS- (nC ₅ H ₁₁ ), CS-CH ( CH ₃ ) -CH ₂ -C ₂ H ₅ , CS-CH ₂ -CH (CH ₃ ) -C ₂ H ₅ , CS-CH ₂ CH ₂ -CH (CH ₃ ) ₂ , CS-C (CH ₃ ) ₂ -C ₂ H ₅ , CS-CH (CH ₃ ) -CH (CH ₃ ) ₂ , CS-CH ₂ -C (CH ₃ ) ₃ , CS-CH (C ₂ H ₅ ) -C ₂ H ₅ , CS- (nC ₆ H ₁₃ ), CS-CH (CH ₃ )-(nC ₄ H ₉ ), CS-CH ₂ -CH (CH ₃ ) CH ₂ -C ₂ H ₅ , CS-CH ₂ CH ₂ -CH (CH ₃ ) -C ₂ H ₅ , CS-CH ₂ CH ₂ CH ₂ -CH (CH ₃ ) ₂ , CS-C (CH ₃ ) ₂ -CH ₂ -C ₂ H ₅ , CS-CH (CH ₃ ) -CH (CH ₃ ) -C ₂ H ₅ , CS-CH (CH ₃ ) -CH ₂ -CH (CH ₃ ) ₂ , CS-CH ₂ -C (CH ₃ ) ₂ -C ₂ H ₅ , CS-CH _2- CH (CH ₃ ) -CH (CH ₃ ) ₂ , CS-CH ₂ CH ₂ -C (CH ₃ ) ₃ , CS-CH (C ₂ H ₅ ) -CH ₂ -C ₂ H ₅ , CS-CH _2- CH (C ₂ H ₅ ) -C ₂ H ₅ , CS-C (CH ₃ ) ₂ -CH (CH ₃ ) ₂ , CS-CH (CH ₃ ) -C (CH ₃ ) ₃ , CS-C (CH ₃ ) (C ₂ H ₅ ) -C ₂ H ₅ , or CS-CH (C ₂ H ₅ ) -CH (CH ₃ ) ₂ , preferably CS-CH ₃ ,, CS-C ₂ H ₅ , CS-CH (CH ₃ ) ₂ or CS- (nC ₄ H ₉ );

- (C ₁ -C ₄ alkoxy) _{carbonyl: CO-OCH 3, CO-} OC 2 H 5, CO-OCH 2 -C 2 H 5, CO-OCH (CH 3) 2, n- butoxycarbonyl, CO-OCH (CH ₃ ) -C ₂ H ₅ , CO-OCH ₂ -CH (CH ₃ ) ₂ or CO-OC (CH ₃ ) ₃ , preferably CO-OCH ₃ or CO-OC ₂ H ₅ ;

-(C ₁ -C ₆ alkoxy) carbonyl: one of the aforementioned-(C ₁ -C ₄ alkoxy) carbonyl radicals or for example n-pentoxy-CO, 1-methylbutoxy-CO, 2- Methylbutoxy-CO, 3-methylbutoxy-CO, 2,2-dimethylpropoxy-CO, 1-ethylpropoxy-CO, n-hexoxy-CO, 1,1-dimethylpropoxy-CO,, 1,2-dimethylpropoxy-CO, 1-methylpentoxy-CO, 2-methylpentoxy-CO, 3-methylpentoxy-CO, 4-methylpentoxy-CO, 1,1-dimethylbutoxy- CO, 1,2-dimethylbutoxy-CO, 1,3-dimethylbutoxy-CO, 2,2-dimethylbutoxy-CO, 2,3-dimethylbutoxy-CO, 3,3-dimethylbutoxy- CO, 1-ethylbutoxy-CO, 2-ethylbutoxy-CO, 1,1,2-tremethylpropoxy-CO, 1,2,2-tremethylpropoxy-CO, 1-ethyl-1- Methylpropoxy-CO, 1-ethyl-2-methylpropoxy-CO, preferably CO-OCH ₃ , CO-OC ₂ H ₅ , CO-OCH ₂ -C ₂ H ₅ , CO-OCH (CH ₃ ) ₂ , n-butoxy-CO, CO-OC (CH ₃ ) ₃ , n-pentoxy-CO or n-hexoxy-CO;

- (C ₁ -C ₄ alkoxy) carbonyl -C ₁ -C ₄ alkyl: as described above, - (C ₁ -C ₄ alkoxy) carbonyl-substituted C ₁ -C ₄ alkyl, which is exemplified by, CH ₂ - CO-OCH ₃ , CH ₂ -CO-OC ₂ H ₅ , CH ₂ -CO-OCH ₂ -C ₂ H ₅ , CH ₂ -CO-OCH (CH ₃ ) ₂ , n-butoxycarbonylmethyl, CH ₂ -CO-OCH (CH ₃ ) -C ₂ H ₅ , CH ₂ -CO-OCH ₂ -CH (CH ₃ ) ₂ , CH ₂ -CO-OC (CH ₃ ) ₃ , 1- (CO-OCH ₃ ) ethyl , 1- (CO-OC ₂ H ₅ ) ethyl, 1- (CO-OCH ₂ -C ₂ H ₅ ) ethyl, 1- [CH (CH ₃ ) ₂ ] ethyl, 1- (n-butoxycarbonyl) Ethyl, 1- (1-methylpropoxycarbonyl) ethyl, 1- (2-methylpropoxycarbonyl) ethyl, 2- (CO-OCH ₃ ) ethyl, 2- (CO-OC ₂ H ₅ ) ethyl, 2- (CO-OCH ₂ -C ₂ H ₅ ) ethyl, 2- [CH-OCH (CH ₃ ) ₂ ] ethyl, 2- (n-butoxycarbonyl) ethyl, 2- (1-methylpropoxycar Carbonyl) ethyl, 2- (2-methylpropoxycarbonyl) ethyl, 2- [CO-OC (CH ₃ ) ₃ ] ethyl, 2- (CO-OCH ₃ ) propyl, 2- (CO-OC ₂ H ₅ ) Propyl, 2- (CO-OCH ₂ -C ₂ H ₅ ) propyl, 2- [CH-OCH (CH ₃ ) ₂ ] propyl, 2- (n-butoxycarbonyl) propyl, 2- (1-methyl Proprol Carbonyl) propyl, 2- (2-propoxycarbonyl) propyl, 2- [CO-OC (CH 3) 3] propyl, 3- (CO-OCH ₃₎ propyl, 3- (CO-OC ₂ H ₅ ) propyl, 3- (CO-OCH ₂ -C ₂ H ₅ ) propyl, 3- [CH-OCH (CH ₃ ) ₂ ] propyl, 3- (n-butoxycarbonyl) propyl, 3- (1- Methylpropoxycarbonyl) propyl, 3- (2-methylpropoxycarbonyl) propyl, 3- [CO-OC (CH ₃ ) ₃ ] propyl, 2- (CO-OCH ₃ ) butyl, 2- (CO- OC ₂ H ₅ ) butyl, 2- (CO-OCH ₂ -C ₂ H ₅ ) butyl, 2- [CH-OCH (CH ₃ ) ₂ ] butyl, 2- (n-butoxycarbonyl) butyl, 2- (1-methylpropoxycarbonyl) butyl, 2- (2-methylpropoxycarbonyl) butyl, 2- [CO-OC (CH ₃ ) ₃ ] butyl, 3- (CO-OCH ₃ ) butyl, 3- (CO-OC ₂ H ₅ ) butyl, 3- (CO-OCH ₂ -C ₂ H ₅ ) butyl, 3- [CH-OCH (CH ₃ ) ₂ ] butyl, 3- (n-butoxycarbonyl) butyl , 3- (1-methylpropoxycarbonyl) butyl, 3- (2-methylpropoxycarbonyl) butyl, 3- [CO-OC (CH ₃ ) ₃ ] butyl, 4- (CO-OCH ₃ ) butyl , 4- (CO-OC ₂ H ₅ ) butyl, 4- (CO-OCH ₂ -C ₂ H ₅ ) butyl, 4- [CH-OCH (CH ₃ ) ₂ ] butyl, 4- (n-butoxide Cycarbonyl) butyl, 4- (1-methylpropoxycarbonyl) butyl, 4- (2-methylpropoxycarbonyl) butyl, 4- [CO-OC (CH ₃ ) ₃ ] butyl, preferably CH ₂ -CO-OCH ₃ , CH ₂ -CO-OC ₂ H ₅ , 1- (CO-OCH ₃ ) ethyl, 1- (CO-OC ₂ H ₅ ) ethyl;

- (C ₁ -C ₆ alkoxy) thiocarbonyl: for _{example, CS-OCH 3, CS-} OC 2 H 5, CS-OCH 2 -C 2 H 5, CS-OCH (CH 3) 2, CS- O (nC ₄ H ₉ ), CS-OCH (CH ₃ ) -C ₂ H ₅ , CS-OCH ₂ -CH (CH ₃ ) ₂ , CS-OC (CH ₃ ) ₃ , CS-O (nC ₅ H ₁₁ ), CS-OCH (CH ₃ ) -CH ₂ -C ₂ H ₅ , CS-OCH ₂ -CH (CH ₃ ) -C ₂ H ₅ , CS-OCH ₂ CH ₂ -CH (CH ₃ ) ₂ , CO- OCH ₂ -C (CH ₃ ) ₃ , CS-OCH (C ₂ H ₅ ) -C ₂ H ₅ , CS-O (nC ₆ H ₁₃ ), CS-OC (CH ₃ ) ₂ -C ₂ H ₅ , CS -OCH (CH ₃ ) -CH (CH ₃ ) ₂ , CS-OCH (CH ₃ )-(nC ₄ H ₉ ), CS-OCH ₂ -CH (CH ₃ ) -CH ₂ -C ₂ H ₅ , CS- OCH ₂ CH ₂ -CH (CH ₃ ) -C ₂ H ₅ , CS-OCH ₂ -CH ₂ -CH ₂ -CH (CH ₃ ) ₂ , CS-OC (CH ₃ ) -CH ₂ -C ₂ H ₅ , CS-OCH (CH ₃ ) -CH (CH ₃ ) -C ₂ H ₅ , CS-OCH (CH ₃ ) -CH ₂ -CH (CH ₃ ) ₂ , CS-OCH ₂ -C (CH ₃ ) ₂ -C ₂ H ₅ , CS-OCH ₂ -CH (CH ₃ ) -CH (CH ₃ ) ₂ , CS-OCH ₂ -CH ₂ -C (CH ₃ ) ₃ , CS-OC (C ₂ H ₅ ) -CH _2- C ₂ H ₅ , CS-OCH ₂ -CH (C ₂ H ₅ ) -C ₂ H ₅ , CS-OC (CH ₃ ) ₂ -CH (CH ₃ ) ₂ , CS-OCH (CH ₃ ) -C (CH ₃ ) ₃ , CS-OC (CH ₃ ) (C ₂ H ₅ ) -C ₂ H ₅ , or CS-OCH (C ₂ H ₅ ) -CH (CH ₃ ) ₂ , preferably CS-OCH ₃ or CS -OC ₂ H ₅ ;

- (C ₁ -C ₄ alkylthio) _{carbonyl: CO-SCH 3, CO-} SC 2 H 5, CO-SCH 2 -C 2 H 5, CO-SCH (CH 3) 2, CO-SCH 2 -CH ₂ -C ₂ H ₅ , CO-SCH (CH ₃ ) -C ₂ H ₅ , CO-SCH ₂ -CH (CH ₃ ) ₂ , or CO-SC (CH ₃ ) ₃ , preferably CO-SCH ₃ or CO-SC ₂ H ₅ ;

- (C ₁ -C ₄ alkylthio) carbonyl -C ₁ -C ₄ alkyl:, (C ₁ -C ₄ alkylthio) carbonyl a C ₁ -C ₄ alkyl, optionally substituted with for example, as described above, CH ₂ -CO-SCH ₃ , CH ₂ -CO-SC ₂ H ₅ , CH ₂ -CO-SCH ₂ -C ₂ H ₅ , CH ₂ -CO-SCH (CH ₃ ) ₂ , CH ₂ -CO-SCH _2- CH ₂ -C ₂ H ₅ , CH ₂ -CO-SCH (CH ₃ ) -C ₂ H ₅ , CH ₂ -CO-SCH ₂ -CH (CH ₃ ) ₂ , CH ₂ -CO-SC (CH ₃ ) ₃ , 1- (CO-SCH ₃ ) ethyl, 1- (CO-SC ₂ H ₅ ) ethyl, 1- (CO-SCH ₂ -C ₂ H ₅ ) ethyl, 1- [CO-SCH (CH ₃ ) ₂ ] Ethyl, 1- (CO-SCH ₂ -CH ₂ -C ₂ H ₅ ) ethyl, 1- [CO-SCH (CH ₃ ) -C ₂ H ₅ ] ethyl, 1- [CO-SCH ₂ -CH (CH ₃ ) ₂ ] ethyl, 1- [CO-SC (CH ₃ ) ₃ ] ethyl, 2- (CO-SCH ₃ ) ethyl, 2- (CO-SC ₂ H ₅ ) ethyl, 2- (CO-SCH ₂ -C ₂ H ₅ ) ethyl, 2- [CO-SCH (CH ₃ ) ₂ ] ethyl, 2- (CO-SCH ₂ -CH ₂ -C ₂ H ₅ ) ethyl, 2- [CO-SCH (CH ₃ ) -C ₂ H ₅ ] ethyl, 2- [CO-SCH ₂ -CH (CH ₃ ) ₂ ] ethyl, 2- [CO-SC (CH ₃ ) ₃ ] ethyl, 2- (CO-SCH ₃ ) propyl, 2- ( CO-SC ₂ H ₅ ) propyl, 2- (CO-SCH ₂ -C ₂ H ₅ ) propyl, 2- [CO-SCH (CH ₃ ) ₂ ] propyl, 2- (CO-SCH ₂ -CH ₂ -C ₂ H ₅ ) propyl, 2- [CO-SCH (CH ₃ ) -C ₂ H ₅ ] propyl, 2- [CO-SCH ₂ -CH (CH ₃ ) ₂ ] propyl, 2- [CO-SC (CH ₃ ) ₃ ] propyl, 3- (CO-SCH ₃ ) propyl, 3- (CO -SC ₂ H ₅ ) propyl, 3- (CO-SCH ₂ -C ₂ H ₅ ) propyl, 3- [CO-SCH (CH ₃ ) ₂ ] propyl, 3- (CO-SCH ₂ -CH ₂ -C ₂ H ₅ ) propyl, 3- [CO-SCH (CH ₃ ) -C ₂ H ₅ ] propyl, 3- [CO-SCH ₂ -CH (CH ₃ ) ₂ ] propyl, 3- [CO-SC (CH ₃ ) ₃ ] propyl, 2- (CO-SCH ₃ ) butyl, 2- (CO-SC ₂ H ₅ ) butyl, 2- (CO-SCH ₂ -C ₂ H ₅ ) butyl, 2- [CO-SCH (CH ₃ ) ₂ ] butyl, 2- (CO-SCH ₂ -CH ₂ -C ₂ H ₅ ) butyl, 2- [CO-SCH (CH ₃ ) -C ₂ H ₅ ] butyl, 2- [CO-SCH ₂ -CH (CH ₃ ) ₂ ] butyl, 2- [CO-SC (CH ₃ ) ₃ ] butyl, 3- (CO-SCH ₃ ) butyl, 3- (CO-SC ₂ H ₅ ) butyl, 3- (CO-SCH _2- C ₂ H ₅ ) butyl, 3- [CO-SCH (CH ₃ ) ₂ ] butyl, 3- (CO-SCH ₂ -CH ₂ -C ₂ H ₅ ) butyl, 3- [CO-SCH (CH ₃ ) -C ₂ H ₅ ] butyl, 3- [CO-SCH ₂ -CH (CH ₃ ) ₂ ] butyl, 3- [CO-SC (CH ₃ ) ₃ ] butyl, 4- (CO-SCH ₃ ) butyl, 4- (CO-SC ₂ H ₅ ) butyl, 4- (CO-SCH ₂ -C ₂ H ₅ ) butyl, 4- [CO-SCH (CH ₃ ) ₂ ] butyl, 4- (CO-SCH ₂ -CH ₂ -C ₂ H ₅ ) butyl, 4- [CO-SCH (CH ₃ ) -C ₂ H ₅ ] butyl, 4- [CO-SCH ₂ -CH (C H ₃ ) ₂ ] butyl, 4- [CO-SC (CH ₃ ) ₃ ] butyl, preferably CH ₂ -CO-SCH ₃ , CH ₂ -CO-SC ₂ H ₅ , 1- (CO-SCH ₃ ) Ethyl, 1- (CO-SC ₂ H ₅ ) ethyl;

-C ₁ -C ₆ -alkylsulfinyl: SO-CH ₃ , SO-C ₂ H ₅ , SO-CH ₂ -C ₂ H ₅ , SO-CH (CH ₃ ) ₂ , SO- (nC ₄ H ₉ ) , C ₁ -C ₄ alkylsulfinyl radicals such as SO—CH (CH ₃ ) —C ₂ H ₅ , SO—CH ₂ —CH (CH ₃ ) ₂ , SO—C (CH ₃ ) ₃ , or for example , SO- (nC ₅ H ₁₁ ), 1-methylbutyl-SO, 2-methylbutyl-SO, 3-methylbutyl-SO, 2,2-dimethylpropyl-SO, 1-ethylpropyl-SO, n-hexyl -SO, 1,1-dimethylpropyl-SO, 1,2-dimethylpropyl-SO, 1-methylpentyl-SO, 2-methylpentyl-SO, 3-methylpentyl-SO, 4-methylpentyl-SO, 1 , 1-dimethylbutyl-SO, 1,2-dimethylbutyl-SO,, 1,3-dimethylbutyl-SO, 2,2-dimethylbutyl-SO, 2,3-dimethylbutyl-SO, 3,3-dimethyl Butyl-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-methylpropyl-SO, preferably SO-CH ₃ , SO-C ₂ H ₅ , SO-CH ₂ -C ₂ H ₅ , SO-CH (CH ₃ ) ₂ , SO- ( nC ₄ H ₉ ), SO-C (CH ₃ ) ₃ , SO- (nC ₅ H ₁₁ ) or SO- (nC ₆ H ₁₃ );

-C ₁ -C ₄ alkylsulfinyl-C ₁ -C ₄ alkyl: C ₁ -C ₄ alkyl substituted with C ₁ -C ₄ alkylsulfinyl as described above, for example CH ₂ SOCH ₃ , CH ₂ SOC ₂ H ₅ , n-propylsulfinylmethyl, CH ₂ SOCH (CH ₃ ) ₂ , n-butylsulfinylmethyl, (1-methylpropylsulfinyl) methyl, (2-methylpropylsulfinyl) methyl, (1 , 1-dimethylethylsulfinyl) methyl, 2-methylsulfinylethyl, 2-ethylsulfinylethyl, 2- (n-propylsulfinyl) ethyl, 2- (1-methylethylsulfinyl) ethyl, 2- ( n-butylsulfinyl) ethyl, 2- (1-methylpropylsulfinyl) ethyl, 2- (2-methylpropylsulfinyl) ethyl, 2- (1,1-dimethylethylsulfinyl) ethyl, 2- (SOCH ₃ ) propyl, 3- (SOCH ₃ ) propyl, 2- (SOC ₂ H ₅ ) propyl, 3- (SOC ₂ H ₅ ) propyl, 3- (propylsulfinyl) propyl, 3- (butylsulfinyl) propyl, 4- (SOCH ₃ ) butyl, 4- (SOC ₂ H ₅ ) butyl, 4- (n-propylsulfinyl) butyl or 4- (n-butylsulfinyl) butyl, especially 2- (SOCH ₃ ) ethyl;

-C ₁ -C ₄ haloalkylsulfinyl -C ₁ -C ₄ alkyl:, -C ₁ -C ₄ haloalkylsulfinyl C ₁ -C ₄ substituted alkyl sulfinyl, e.g., 2- (2, as described above, 2,2-trifluoroethylsulfinyl) ethyl;

-C ₁ -C ₄ alkylsulfonyl: SO ₂ -CH ₃ , SO ₂ -C ₂ H ₅ , SO ₂ -CH ₂ -C ₂ H ₅ , SO ₂ -CH (CH ₃ ) ₂ , n-butylsulfonyl , SO ₂ -CH (CH ₃ ) -C ₂ H ₅ , SO ₂ -CH ₂ -CH (CH ₃ ) ₂ or SO ₂ -C (CH ₃ ) ₃ , preferably SO ₂ -CH ₃ , SO _2- C ₂ H ₅ ;

-C ₁ -C ₄ haloalkylsulfonyl: -C ₁ -C ₄ alkylsulfonyl radicals, eg, SO ₂ , partially or fully substituted with fluorine, chlorine, bromine and / or iodine as described above -CH ₂ F, SO ₂ -CHF ₂ , SO ₂ -CF ₃ , SO ₂ -CH ₂ Cl, SO ₂ -CH (Cl) ₂ , SO ₂ -C (Cl) ₃ , chlorofluoromethylsulfonyl, dichloro Fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-di Fluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl,, 2-chloro-2,2-difluoroethylsulfonyl, 2,2 -Dichloro-2-fluoroethylsulfonyl,, 2,2,2-trichloroethylsulfonyl, SO ₂ -C ₂ F ₅ , 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2, 2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfo , 2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl , SO ₂ -CH ₂ -C ₂ F ₅ , SO ₂ -CF ₂ -C ₂ F ₅ , 1- (fluoromethyl) -2-fluoroethylsulfonyl, 1- (chloromethyl) -2-chloroethyl Sulfonyl, 1- (bromomethyl) -2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl, preferably Preferably SO ₂ -CF ₃ , SO ₂ -CH ₂ Cl or 2,2,2-trifluoroethylsulfonyl;

-C ₁ -C ₆ alkylsulfonyl: C ₁ -C ₄ alkylsulfonyl radicals as described above, or for example SO _2- (nC ₅ H ₁₁ ), 1-methylbutyl-SO ₂ , 2-methyl Butyl-SO ₂ , 3-methylbutyl-SO ₂ , 2,2-di-methylpropyl-SO ₂ , 1-ethylpropyl-SO ₂ , n-hexyl-SO ₂ , 1,1-dimethylpropyl-SO ₂ , 1,2-dimethylpropyl-SO ₂ , 1-methylpentyl-SO ₂ , 2-methylpentyl-SO ₂ , 3-methylpentyl-SO ₂ , 4-methylpentyl-SO ₂ , 1,1-dimethylbutyl-SO ₂ , 1,2-dimethylbutyl-SO ₂ , 1,3-dimethylbutyl-SO ₂ , 2,2-dimethylbutyl-SO ₂ , 2,3-dimethylbutyl-SO ₂ , 3,3-dimethylbutyl-SO ₂ , 1-ethylbutyl-SO ₂ , 2-ethylbutyl-SO ₂ , 1,1,2-trimethylpropyl-SO ₂ , 1,2,2-trimethylpropyl-SO ₂ , 1-ethyl-1-methylpropyl -SO ₂ , or 1-ethyl- ₂ -methylpropyl-SO ₂ , preferably SO ₂ -CH ₃ , SO ₂ -C ₂ H ₅ , SO ₂ -CH ₂ -C ₂ H ₅ , SO ₂ -CH ( CH ₃ ) ₂ , SO _2- (nC ₄ H ₉ ), SO ₂ -C (CH ₃ ) ₃ , SO _2- (nC ₅ H ₁₁ ), or SO _2- (nC ₆ H ₁₃ );

-C ₁ -C ₄ alkylsulfonyl-C ₁ -C ₄ alkyl: C ₁ -C ₄ alkyl substituted with C ₁ -C ₄ alkylsulfonyl as described above, eg CH ₂ SO ₂ -CH ₃ , CH ₂ SO ₂ -C ₂ H ₅ , CH ₂ SO ₂ -CH ₂ -C ₂ H ₅ , CH ₂ SO ₂ -CH (CH ₃ ) ₂ , CH ₂ SO ₂ -CH ₂ CH ₂ -C ₂ H ₅ , (1-methylpropylsulfonyl) methyl, (2-methylpropylsulfonyl) methyl, CH ₂ SO ₂ -C (CH ₃ ) ₃ , CH (CH ₃ ) SO ₂ -CH ₃ , CH (CH ₃ ) SO ₂ -C ₂ H ₅ , CH ₂ CH ₂ SO ₂ -CH ₃ , CH ₂ CH ₂ SO ₂ -C ₂ H ₅ , CH ₂ CH ₂ SO ₂ -CH ₂ C ₂ H ₅ , CH ₂ CH ₂ SO _2- CH (CH ₃ ) ₂ , CH ₂ CH ₂ SO ₂ -CH ₂ CH ₂ -C ₂ H ₅ , 2- (1-methylpropylsulfonyl) ethyl, 2- (2-methylpropylsulfonyl) ethyl, CH ₂ CH ₂ SO ₂ -C (CH ₃ ) ₃ , 2- (SO ₂ -CH ₃ ) propyl, 2- (SO ₂ -C ₂ H ₅ ) propyl, 2- (SO ₂ -CH ₂ -C ₂ H ₅ ) Propyl, 2- [SO ₂ -CH (CH ₃ ) ₂ ] propyl, 2- (SO ₂ -CH ₂ CH ₂ -C ₂ H ₅ ) propyl, 2- (1-methylpropylsulfonyl) propyl, 2- ( 2-methylpropylsulfonyl) propyl, 2- [SO ₂ -C (CH ₃ ) ₃ ] propyl, 3- (SO ₂ -CH ₃ ) propyl, 3- (SO ₂ -C ₂ H ₅ ) propyl, 3- (SO ₂ -CH ₂ -C ₂ H ₅ ) propyl, 3- [SO ₂ -CH (CH ₃ ) ₂ ] propyl, 3- (SO ₂ -CH ₂ CH ₂ -C ₂ H ₅ ) propyl, 3- (1-methylpropylsulfonyl ) Propyl, 3- (2-methylpropylsulfonyl) propyl, 3- [SO ₂ -C (CH ₃ ) ₃ ] propyl, 2- (SO ₂ -CH ₃ ) butyl, 2- (SO ₂ -C ₂ H ₅ ) butyl, 2- (SO ₂ -CH ₂ -C ₂ H ₅ ) butyl, 2- [SO ₂ -CH (CH ₃ ) ₂ ] butyl, 2- (SO ₂ -CH ₂ CH ₂ -C ₂ H ₅ ) Butyl, 2- (1-methylpropylsulfonyl) butyl, 2- (2-methylpropylsulfonyl) butyl, 2- [SO ₂ -C (CH ₃ ) ₃ ] butyl, 3- (SO ₂ -CH ₃ ) Butyl, 3- (SO ₂ -C ₂ H ₅ ) butyl, 3- (SO ₂ -CH ₂ -C ₂ H ₅ ) butyl, 3- [SO ₂ -CH (CH ₃ ) ₂ ] butyl, 3- ( SO ₂ -CH ₂ CH ₂ -C ₂ H ₅ ) butyl, 3- (1-methylpropylsulfonyl) butyl, 3- (2-methylpropylsulfonyl) butyl, 3- [SO ₂ -C (CH ₃ ) ₃ ] butyl, 4- (SO ₂ -CH ₃ ) butyl, 4- (SO ₂ -C ₂ H ₅ ) butyl, 4- (SO ₂ -CH ₂ -C ₂ H ₅ ) butyl, 4- [SO _2- CH (CH ₃ ) ₂ ] butyl, 4- (SO ₂ -CH ₂ CH ₂ -C ₂ H ₅ ) butyl, 4- (1-methylpropylsulfonyl) butyl, 4- (2-methylpropylsulfonyl) butyl , 4- [SO ₂ -C (CH ₃ ) ₃ ] butyl, in particular CH ₂ CH ₂ SO ₂ -CH ₃ , CH ₂ CH ₂ SO ₂ -C ₂ H ₅ ;

-C ₁ -C ₄ haloalkylsulfonyl-C ₁ -C ₄ alkyl: C ₁ -C ₄ alkyl substituted with C ₁ -C ₄ haloalkylsulfonyl as mentioned above, eg, 2- (2,2 , 2-trifluoroethsulfonyl) ethyl;

-C ₁ -C ₄ alkylamino-C ₁ -C ₄ alkyl: H ₃ C-NH, H ₅ C ₂ -NH-, n-propyl-NH-, 1-methylethyl-NH-, n-butyl-NH C ₁ -C, such as ₁ -methylpropyl-NH-, 2-methylpropyl-NH- and 1,1-dimethylethyl-NH-, preferably H ₃ C-NH, H ₅ C ₂ -NH- a C ₁ -C ₄ alkylamino substituted with a _4-alkyl, i.e., for _{example, CH 2 CH 2 -NH-CH} 3, CH 2 CH 2 -N (CH 3) 2, CH 2 CH 2 -NH-C 2 H ₅ , CH ₂ CH ₂ -N (C ₂ H ₅ ) ₂ ,

- (C ₁ -C ₄ alkyl) _{carbonyl: CO-NH-CH 3,} CO-NH-C 2 H 5, n- propylamino, CO-NH-CH (CH 3) 2, CO-NH-CH ₂ CH ₂ -C ₂ H ₅ , CO-NH-CH (CH ₃ ) -C ₂ H ₅ , CO-NH-CH ₂ -CH (CH ₃ ) ₂ , CO-NH-C (CH ₃ ) ₃ , preferably Preferably CO-NH-CH ₃ , CO-NH-C ₂ H ₅ ;

-(C ₁ -C ₆ alkylamino) carbonyl: one or one of the above-mentioned (C ₁ -C ₄ alkylamino) carbonyl radicals, for example CO-NH- (nC ₅ H ₁₁ ), 1-methylbutyl -NHCO-, 2-methylbutyl-NHCO-, 3-methylbutyl-NHCO-, 2,2-dimethylpropyl-NHCO-, 1-ethylpropyl-NHCO-, CO-NH- (nC ₆ H ₁₃ ), 1 , 1-dimethylpropyl-NHCO-, 1,2-dimethylpropyl-NHCO-, 1-methylpentyl-NHCO-, 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-NHCO-, 1,1,2-trimethylpropyl-NHCO-, 1,2,2-trimethylpropyl-NHCO- , 1-ethyl-1-methylpropyl-NHCO-, 1-ethyl-2-methylpropyl-NHCO-, preferably CO-NH-CH ₃ , CO-NH-C ₂ H ₅ , CO-NH-CH ₂ -C ₂ H ₅ , CO-NH-CH (CH ₃ ) ₂ , CO-NH- (nC ₄ H ₉ ), CO-NH-C (CH ₃ ) ₃ , CO-NH- (nC ₅ H ₁₁ ) or CO-NH- (nC ₆ H ₁₃ );

-(C ₁ -C ₄ alkylamino) carbonyl-C ₁ -C ₄ alkyl: as mentioned above (C ₁ -C ₄ alkylamino) carbonyl, preferably CO-NH-CH ₃ or CO-NH C ₁ -C ₄ alkyl substituted with —C ₂ H ₅ , for example CH ₂ -CO-NH-CH ₃ , CH ₂ -CO-NH-C ₂ H ₅ , CH ₂ -CO-NH-CH ₂ -C ₂ H ₅ , CH ₂ -CO-NH-CH (CH ₃ ) ₂ , CH ₂ -CO-NH-CH ₂ CH ₂ -C ₂ H ₅ , CH ₂ -CO-NH-CH (CH ₃ )- C ₂ H ₅ , CH ₂ -CO-NH-CH ₂ CH (CH ₃ ) ₂ , CH ₂ -CO-NH-C (CH ₃ ) ₃ , CH (CH ₃ ) -CO-NH-CH ₃ , CH ( CH ₃ ) -CO-NH-C ₂ H ₅ , 2- (CO-NH-CH ₃ ) ethyl, 2- (CO-NH-C ₂ H ₅ ) ethyl, 2- (CO-NH-CH ₂ -C ₂ H ₅ ) ethyl, 2- [CH ₂ -CO-NH-CH (CH ₃ ) ₂ ] ethyl, 2- (CO-NH-CH ₂ CH ₂ -C ₂ H ₅ ) ethyl, 2- [CO-NH -CH (CH ₃ ) -C ₂ H ₅ ] ethyl, 2- [CO-NH-CH ₂ CH (CH ₃ ) ₂ ] ethyl, 2- [CO-NH-C (CH ₃ ) ₃ ] ethyl, 2- (CO-NH-CH ₃ ) propyl, 2- (CO-NH-C ₂ H ₅ ) propyl, 2- (CO-NH-CH ₂ -C ₂ H ₅ ) propyl, 2- [CH ₂ -CO-NH -CH (CH ₃ ) ₂ ] propyl, 2- (CO-NH-CH ₂ CH ₂ -C ₂ H ₅ ) propyl, 2- [CO-NH-CH (CH ₃ ) -C ₂ H ₅ ] propyl, 2 -[CO-NH-CH ₂ CH (CH ₃ ) ₂ ] propyl, 2- [CO-NH-C (CH ₃ ) ₃ ] propyl, 3- (CO-NH-CH ₃ ) propyl, 3- (CO-NH-C ₂ H ₅ ) propyl, 3- (CO-NH-CH ₂ -C ₂ H ₅ ) propyl , 3- [CH ₂ -CO-NH-CH (CH ₃ ) ₂ ] propyl, 3- (CO-NH-CH ₂ CH ₂ -C ₂ H ₅ ) propyl, 3- [CO-NH-CH (CH ₃ ) -C ₂ H ₅ ] propyl, 3- [CO-NH-CH ₂ CH (CH ₃ ) ₂ ] propyl, 3- [CO-NH-C (CH ₃ ) ₃ ] propyl, 2- (CO-NH- CH ₃ ) butyl, 2- (CO-NH-C ₂ H ₅ ) butyl, 2- (CO-NH-CH ₂ -C ₂ H ₅ ) butyl, 2- [CH ₂ -CO-NH-CH (CH ₃ ) ₂ ] butyl, 2- (CO-NH-CH ₂ CH ₂ -C ₂ H ₅ ) butyl, 2- [CO-NH-CH (CH ₃ ) -C ₂ H ₅ ] butyl, 2- [CO-NH -CH ₂ CH (CH ₃ ) ₂ ] butyl, 2- [CO-NH-C (CH ₃ ) ₃ ] butyl, 3- (CO-NH-CH ₃ ) butyl, 3- (CO-NH-C ₂ H ₅ ) butyl, 3- (CO-NH-CH ₂ -C ₂ H ₅ ) butyl, 3- [CH ₂ -CO-NH-CH (CH ₃ ) ₂ ] butyl, 3- (CO-NH-CH ₂ CH _2- C ₂ H ₅ ) butyl, 3- [CO-NH-CH (CH ₃ ) -C ₂ H ₅ ] butyl, 3- [CO-NH-CH ₂ CH (CH ₃ ) ₂ ] butyl, 3- [ CO-NH-C (CH ₃ ) ₃ ] butyl, 4- (CO-NH-CH ₃ ) butyl, 4- (CO-NH-C ₂ H ₅ ) butyl, 4- (CO-NH-CH ₂ -C ₂ H ₅ ) butyl, 4- [CH ₂ -CO-NH-CH (CH ₃ ) ₂ ] butyl, 4- (CO-NH-CH ₂ CH ₂ -C ₂ H ₅ ) butyl, 4- [CO-NH -CH (CH ₃ ) -C ₂ H ₅ ] butyl, 4- [CO-NH-CH ₂ CH (CH ₃ ) ₂ ] butyl, 4- [CO-NH-C (CH ₃ ) ₃ ] butyl, preferably CH ₂ -CO-NH-CH ₃ , CH ₂ -CO -NH-C ₂ H ₅ , CH (CH ₃ ) -CO-NH-CH ₃ or CH (CH ₃ ) -CO-NH-C ₂ H ₅ ;

- di (C ₁ -C ₄ alkyl) _{amino: N (CH 3) 2,} N (C 2 H 5) 2, N, N- dipropylamino, N, N- dipropylamino, N, N- di ( 1-methylethyl) amino, N, N-dibutylamino, N, N-di (1-methylpropyl) amino, N, N-di (2-methylpropyl) amino, N, N-di (1,1 -Dimethylethyl) amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N- (1-methylethyl) 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-propylamino, N-ethyl-N- (1-methylethyl) amino, N-butyl-N-ethylamino, 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-propylamino, 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) amino, N-butyl-N- (2-methylpropyl) amino, N-butyl-N- (1,1-dimethyl Ethyl) amino, N- (1-methylpropyl) -N- (2-methylpropyl) amino, N- (1,1-dimethylethyl) -N- (1-methylpropyl) amino or N- (1,1 -Dimethylethyl) -N- (2-methylpropyl) amino, preferably N (CH ₃ ) ₂ or N (C ₂ H ₅ ) ₂ ;

- di (C ₁ -C ₄ alkyl) -C ₁ -C ₄ alkyl: for the above-mentioned de-as (C ₁ -C ₄ alkyl) C ₁ -C ₄ alkyl substituted with amino, for example, CH ₂ N (CH ₃ ) ₂ , CH ₂ N (C ₂ H ₅ ) ₂ , N, N-dipropylaminomethyl, N, N-di [CH (CH ₃ ) ₂ ] aminomethyl, N, N-dibutylaminomethyl , N, N-di- (1-methylpropyl) aminomethyl, N, N-di (2-methylpropyl) aminomethyl, N, N-di [C (CH ₃ ) ₃ ] aminomethyl, N-ethyl- N-methylaminomethyl, N-methyl-N-propylaminomethyl, N-methyl-N- [CH (CH ₃ ) ₂ ] aminomethyl, N-butyl-N-methylaminomethyl, N-methyl-N- ( 1-methylpropyl) aminomethyl, N-methyl-N- (2-methylpropyl) aminomethyl, N- [C (CH ₃ ) ₃ ] -N-methylaminomethyl, N-ethyl-N-propylaminomethyl, N-ethyl-N- [CH (CH ₃ ) ₂ ] aminomethyl, N-butyl-N-ethylaminomethyl, N-ethyl-N- (1-methylpropyl) aminomethyl, N-ethyl-N- (2 -methylpropyl) aminomethyl, N- ethyl _{-N- [C (CH 3) 3} ] _{aminomethyl, N- [CH (CH 3)} 2] -N- methyl-propylamino, N- butyl -N- profile Peel-aminomethyl, N- (1- methylpropyl) -N- methyl-propylamino, N- (2- methylpropyl) -N- _{propyl-aminomethyl, N- [C (CH 3)} 3] -N- propylamino methyl , N-butyl-N- (1-methylethyl) -aminomethyl, N- [CH (CH ₃ ) ₂ ] -N- (1-methylpropyl) aminomethyl, N- [CH (CH ₃ ) ₂ ]- N- (2-methylpropyl) aminomethyl, N- [C (CH ₃ ) ₃ ] -N- [CH (CH ₃ ) ₂ ] aminomethyl, N-butyl-N- (1-methylpropyl) aminomethyl, N-butyl-N- (2-methylpropyl) aminomethyl, N-butyl-N- [C (CH ₃ ) ₃ ] -aminomethyl, N- (1-methylpropyl) -N- (2-methylpropyl) Aminomethyl, N- [C (CH ₃ ) ₃ ] -N- (1-methylpropyl) aminomethyl, N- [C (CH ₃ ) ₃ ] -N- (2-methylpropyl) aminomethyl, N, N -Dimethylaminoethyl, N, N-diethylaminoethyl, N, N-di (n-propyl) aminoethyl, N, N-di [CH (CH ₃ ) ₂ ] aminoethyl, N, N-dibutylamino Ethyl, N, N-di- (1-methylpropyl) aminoethyl, N, N-di (2-methylpropyl) aminoethyl, N, N-di [C (CH ₃ ) ₃ ] aminoethyl, N-ethyl -N-methylaminoethyl, N- Til -N- propylamino-ethyl, N- methyl _{-N- [CH (CH 3) 2} ] aminoethyl, N- butyl -N- methyl-amino-ethyl, N- methyl -N- (1- methylpropyl) aminoethyl, N-methyl-N- (2-methylpropyl) aminoethyl, N- [C (CH ₃ ) ₃ ] -N-methylaminoethyl, N-ethyl-N-propylaminoethyl, N-ethyl-N- [CH (CH ₃ ) ₂ ] aminoethyl, N-butyl-N-ethylaminoethyl, N-ethyl-N- (1-methylpropyl) aminoethyl, N-ethyl-N- (2-methylpropyl) aminoethyl, N -Ethyl-N- [C (CH ₃ ) ₃ ] aminoethyl, N- [CH (CH ₃ ) ₂ ] -N-propylaminoethyl, N-butyl-N-propylaminoethyl, N- (1-methylpropyl ) -N-propylaminoethyl, N- (2-methylpropyl) -N-propylaminoethyl, N- [C (CH ₃ ) ₃ ] -N-propylaminoethyl, N-butyl-N- [CH (CH ₃ ) ₂ ] aminoethyl, N- [CH (CH ₃ ) ₂ ] -N- (1-methylpropyl) aminoethyl, N- [CH (CH ₃ ) ₂ ] -N- (2-methylpropyl) aminoethyl , N- [C (CH ₃ ) ₃ ] -N- [CH (CH ₃ ) ₂ ] aminoethyl, N-butyl-N- (1-methylpropyl) aminoethyl, N-butyl-N- (2-methyl Profile) Ah No-ethyl, N- butyl _{-N- [C (CH 3) 3} ] - amino-ethyl, N- (1- methylpropyl) -N- (2- methylpropyl) _{aminoethyl, N- [C (CH 3)} 3 ] -N- (1-methylpropyl) aminoethyl, N- [C (CH ₃ ) ₃ ] -N- (2-methylpropyl) aminoethyl, in particular N, N-dimethylaminoethyl or N, N-diethyl Aminoethyl;

- di (C ₁ -C ₄ alkyl) _{aminocarbonyl: CO-N (CH 3)} 2, CO-N (C 2 H 5), CO-N (CH 2 -C 2 H 5) 2, CO-N [CH (CH ₃ ) ₂ ] ₂ , N, N-dibutylaminocarbonyl, CO-N [CH (CH ₃ ) -C ₂ H ₅ ] ₂ , CO-N [CH ₂ -CH (CH ₃ ) ₂ ] ₂ , CO-N [C (CH ₃ ) ₃ ] ₂ , N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N- [CH (CH ₃ ) ₂ ] aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N- (1-methylpropyl) aminocarbonyl, N-methyl-N- (2-methylpropyl) aminocarbonyl, N -Methyl-N- [CH (CH ₃ ) ₂ ] aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N- (1-methylpropyl) aminocarbonyl, N-methyl-N- (2-methylpropyl) aminocarbonyl, N- [C (CH ₃ ) ₃ ] -N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N- [CH (CH ₃ ) ₂ ] aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N- (1-methylpropyl) aminocarbonyl, N-ethyl-N- (2-methylpropyl) aminocarbonyl, N-on Tyl-N- [C (CH ₃ ) ₃ ] aminocarbonyl, N- [CH (CH ₃ ) ₂ ] -N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N- (1- Methylpropyl) -N-propylaminocarbonyl, N- (2-methylpropyl) -N-propylaminocarbonyl, N- [C (CH ₃ ) ₃ ] -N-propylaminocarbonyl, N-butyl-N -[CH (CH ₃ ) ₂ ] aminocarbonyl, N- [CH (CH ₃ ) ₂ ] -N- (1-methylpropyl) aminocarbonyl, N- [CH (CH ₃ ) ₂ ] -N- ( 2-methylpropyl) aminocarbonyl, N- [C (CH ₃ ) ₃ ] -N- [CH (CH ₃ ) ₂ ] aminocarbonyl, N-butyl-N- (1-methylpropyl) aminocarbonyl, N-butyl-N- (2-methylpropyl) aminocarbonyl, N-butyl-N- [C (CH ₃ ) ₃ ] aminocarbonyl, N- (1-methylpropyl) -N- (2-methylpropyl ) Aminocarbonyl, N- [C (CH ₃ ) ₃ ] -N- (1-methylpropyl) aminocarbonyl, or N- [C (CH ₃ ) ₃ ] -N- (2-methylpropyl) aminocarbon Carbonyl, preferably CO-N (CH ₃ ) ₂ or CO-N (C ₂ H ₅ );

-Di (C ₁ -C ₆ alkyl) aminocarbonyl: one or more of the aforementioned di (C ₁ -C ₄ alkyl) aminocarbonyl radicals, for example N (CH ₃ )-(nC ₅ H ₁₁ ), N (C ₂ H ₅ )-(nC ₅ H ₁₁ ), N (CH ₂ -C ₂ H ₅ )-(nC ₅ H ₁₁ ), N (nC ₄ H ₉ )-(nC ₅ H ₁₁ ), N ( nC ₅ H ₁₁ )-(nC ₅ H ₁₁ ), N (nC ₆ H ₁₃ )-(nC ₅ H ₁₁ ), N (CH ₃ )-(nC ₆ H ₁₃ ), N (C ₂ H ₅ )-( nC ₆ H ₁₃ ), N (CH ₂ -C ₂ H ₅ )-(nC ₆ H ₁₃ ), N (nC ₄ H ₉ )-(nC ₆ H ₁₃ ), N (nC ₅ H ₁₁ )-(nC ₆ H ₁₃ ) or N (nC ₆ H ₁₃ ) ₂ ,

- di (C ₁ -C ₄ alkyl) amino carbonyl -C ₁ -C ₄ alkyl: di (C ₁ -C ₄ alkyl) aminocarbonyl, preferably CO-N (CH _{3) 2} as described above, Or C ₁ -C ₄ alkyl substituted with CO—N (C ₂ H ₅ ) ₂ . Eg CH ₂ -CO-N (CH ₃ ) ₂ , CH ₂ -CO-N (C ₂ H ₅ ) ₂ , CH (CH ₃ ) -CO-N (CH ₃ ) ₂ , or CH (CH ₃ )- CO-N (C ₂ H ₅ ) ₂ , preferably, CH ₂ -CO-N (CH ₃ ) ₂ or CH (CH ₃ ) -CO-N (CH ₃ ) ₂ ;

- di (C ₁ -C ₄ alkyl) -C ₁ -C ₄ alkyl sulfonyl _{Force: -PO (OCH 3) 2,} -PO (OC 2 H 5) 2, N, N- dipropyl phosphine sulfonyl, N, N -Di (1-methylethyl) phosphonyl, N, N-dibutylphosphonyl, N, N-di (1-methylpropyl) phosphonyl, N, N-di (2-methylpropyl) phosphonyl, N, N-di (1,1-dimethylethyl) phosphonyl, N-ethyl-N-methylphosphonyl, N-methyl-N-propylphosphonyl, 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-dimethylethyl)- N-methylphosphonyl, N-ethyl-N-propylphosphonyl, N-ethyl-N- (1-methylethyl) phosphonyl, N-butyl-N-ethylphosphonyl, N-ethyl-N- (1- Methylpropyl) phosphonyl, N-ethyl-N- (2-methipropyl) phosphonyl, N-ethyl-N- (1,1-dimethylethyl) phosphonyl, N- (1-methylethyl) -N-propyl Phosphonyl, N-butyl-N-propylphosphonyl, N- (1-methylpropyl) -N-propylphosphonyl, N- (2-methylpropyl) -N-propylphosphonyl, N- (1,1- Dime Ethyl) -N-propylphosphonyl, N-butyl-N- (1-methylethyl) phosphonyl, N- (1-methylethyl) -N- (1-methylpropyl) phosphonyl, N- (1-methyl Ethyl) -N- (2-methylpropyl) phosphonyl, N- (1,1-dimethylethyl) -N- (1-methylethyl) phosphonyl, N-butyl-N- (1-methylpropyl) phosphonyl , N-butyl-N- (2-methylpropyl) phosphonyl, N-butyl-N- (1,1-dimethylethyl) phosphonyl, N- (1-methylpropyl) -N- (2-methylpropyl) Phosphonyl, N- (1,1-dimethylethyl) -N- (1-methylpropyl) phosphonyl or N- (1,1-dimethylethyl) -N- (2-methylpropyl) phosphonyl, preferably -PO (OCH _{3) 2} or -PO (OC ₂ H ₅₎ di (C ₁ -C ₄ alkyl) C ₁ -C ₄ alkyl substituted with phosphonic sulfonyl, such as _2. Examples include CH ₂ -PO (OCH ₃ ) ₂ , CH ₂ -PO (OC ₂ H ₅ ) ₂ , CH (CH ₃ ) -PO (OCH ₃ ) ₂ or CH (CH ₃ ) -PO (OC ₂ H ₅ ) ₂ ;

-C ₃ -C ₆ -alkenyl: prop-1-en-1-yl, allyl, 1-methylethenyl, 1-buten-1-yl, 1-buten-2-yl, 1-butene-3 -Yl, 2-buten-1-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-ene-1 -Yl, 2-methylprop-2-en-1-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1 -Methylbut-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-ene-1 -Yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1, 2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-2-yl, n-hex-1-ene 1-yl, n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1- 1, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-ene 1-yl, 1-methylpent-2-en-1-yl, 2- Tilpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-ene-1- 1, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2- En-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl , 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3- Dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2- En-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-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-ene-1 -Yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1 -En-1-yl, It is 1-ethyl-2-methyl-prop-2-en-1-yl;

-C ₃ -C ₆ -haloalkenyl: As mentioned above, C ₃ -C ₆ -alkenyl, eg 2-chloro, partially or fully substituted with fluorine, chlorine, bromine and / or iodine Allyl, 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;

-Cyano-C ₃ -C ₆ -alkenyl: for example 2-cyanoallyl, 3-cyanoallyl, 4-cyanobut-2-enyl, 4-cyanobut-3-enyl or 5 Cyanopent-4-enyl;

-C ₃ -C ₆ -alkynyl: prop-1-yn-1-yl, prop-2-yn-1-yl, n-but-1-yn-1-yl, n-but-1- In-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn- 3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4- 1, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, n-hex-1-yn-1- 1, n-hex-1-yn-3-yl, n-hex-1-yn-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- Hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3- Methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl, 4-methylpent-2-yn-5-yl, preferably prop-2-yn-1-yl;

-C ₃ -C ₆ - haloalkynyl: fluorine, chlorine, bromine, and (or) a partially or entirely substituted with a C ₃ -C ₆ iodide as mentioned above-alkynyl, for example, 1, 1 -Difluoroprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobuty- 2-yn-1-yl, 5-fluoropent-3-yn-1-yl or 6-fluorohex-4-yn-1-yl;

-Cyano-C ₃ -C ₆ -alkynyl: for example 3-cyanopropargyl, 4-cyanobut-2-yn-1-yl, 5-cyanopent-3-yne-1 -Yl and 6-cyanohex-4-yn-1-yl;

-C ₃ -C ₄ -alkenyloxy-C ₁ -C ₄ -alkyl: allyloxy, but-1-en-3-yloxy, but-1-en-4-yloxy, but-2-ene- C ₁ -C ₄ -alkyl substituted with C ₃ -C ₄ -alkenyloxy, such as 1-yloxy, 1-methylprop-2-enyloxy or 2-methylprop-2-enyloxy, ie For example allyloxymethyl, 2-allyloxyethyl or but-1-en-4-yloxymethyl, especially 2-allyloxyethyl;

-C ₃ -C ₄ -alkynyloxy-C ₁ -C ₄ -alkyl: propargyloxy, but-1-yn-3-yloxy, but-1-yn-4-yloxy, but-2- Substituted with C ₃ -C ₄ -alkynyloxy, such as in-1-yloxy, 1-methylprop-2-ynyloxy or 2-methylprop-2-ynyloxy, preferably propargyloxy C ₁ -C ₄ -alkyl, eg, propargyloxymethyl or 2-propargyloxyethyl, especially 2- (propargyloxy) ethyl;

-C ₃ -C ₄ -alkenylthio-C ₁ -C ₄ -alkyl: allylthio, but-1-en-3-ylthio, but-1-en-4-ylthio, but-2-ene- C ₁ -C ₄ -alkyl substituted with C ₃ -C ₄ -alkenylthio such as 1-ylthio, 1-methylprop-2-enylthio or 2-methylprop-2-enylthio, ie eg For example, allylthiomethyl, 2-allylthioethyl or but-1-en-4-ylthiomethyl, especially 2- (allylthio) ethyl;

-C ₃ -C ₄ -alkynylthio-C ₁ -C ₄ -alkyl: propargylthio, but- ₁ -yn- ₃ -ylthio, but- _1- yn- ₄ -ylthio, but-2- Substituted with C ₃ -C ₄ -alkynylthio such as in-1-ylthio, 1-methylprop-2-ynylthio or 2-methylprop-2-ynylthio, preferably propargylthio C ₁ -C ₄ -alkyl, ie, for example, propargylthiomethyl or 2-propargylthioethyl, especially 2- (propargylthio) ethyl;

-C ₃ -C ₄ -alkenylsulfinyl-C ₁ -C ₄ -alkyl: allylsulfinyl, but-1-en-3-ylsulfinyl, but-1-en-4-ylsulfinyl, but-2-ene C ₁ -C ₄ -alkyl substituted with C ₃ -C ₄ -alkenylsulfinyl, such as -1-ylsulfinyl, 1-methylprop-2-enylsulfinyl or 2-methylprop-2-enylsulfinyl Ie, allylsulfinylmethyl, 2-allylsulfinylethyl or but-1-en-4-ylsulfinylmethyl, in particular 2- (allylsulfinyl) ethyl;

-C ₃ -C ₄ -alkynylsulfinyl-C ₁ -C ₄ -alkyl: propargylsulfinyl, but-1-yn-3-ylsulfinyl, but-1-yn- ₄ -ylsulfinyl, but-2- C ₃ -C ₄ -alkynylsulfinyl, such as in-1-ylsulfinyl, 1-methylprop-2-ynylsulfinyl or 2-methylprop-2-ynylsulfinyl, preferably propargylsulfinyl Substituted C ₁ -C ₄ -alkyl, eg, propargylsulfinylmethyl or 2-propargylsulfinylethyl, especially 2- (propargylsulfinyl) ethyl;

-C ₃ -C ₄ -alkenylsulfonyl-C ₁ -C ₄ -alkyl: allylsulfonyl, but-1-en-3-ylsulfonyl, but-1-en-4-ylsulfonyl, but-2-ene C ₁ -C ₄ -alkyl substituted with C ₃ -C ₄ -alkenylsulfonyl such as -1-ylsulfonyl, 1-methylprop-2-enylsulfonyl or 2-methylprop-2-enylsulfonyl Ie, allylsulfonylmethyl, 2-allylsulfonylethyl or but-1-en-4-ylsulfonylmethyl, in particular 2- (allylsulfonyl) ethyl;

-C ₃ -C ₄ -alkynylsulfonyl-C ₁ -C ₄ -alkyl: propargylsulfonyl, but-1-yn-3-ylsulfonyl, but-1-yn- ₄ -ylsulfonyl, but-2- C ₃ -C ₄ -alkynylsulfonyl, such as in-1-ylsulfonyl, 1-methylprop-2-ynylsulfonyl or 2-methylprop-2-ynylsulfonyl, preferably propargylsulfonyl Substituted C ₁ -C ₄ -alkyl, eg, propargylsulfonylmethyl or 2-propargylsulfonylethyl, especially 2- (propargylsulfonyl) ethyl;

-C ₃ -C ₆ -cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;

-C ₃ -C ₈ -cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl;

-C ₃ -C ₈ -cycloalkyl-C ₁ -C ₆ -alkyl: for example cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, cyclooctylmethyl, 2- (cyclo Propyl) ethyl, 2- (cyclobutyl) ethyl, 2- (cyclopentyl) ethyl, 2- (cyclohexyl) ethyl, 2- (cycloheptyl) ethyl, 2- (cyclooctyl) ethyl, 3- (cyclopropyl) Propyl, 3- (cyclobutyl) propyl, 3- (cyclopentyl) propyl, 3- (cyclohexyl) propyl, 3- (cycloheptyl) propyl, 3- (cyclooctyl) propyl, 4- (cyclopropyl) butyl, 4- (cyclobutyl) butyl, 4- (cyclopentyl) butyl, 4- (cyclohexyl) butyl, 4- (cycloheptyl) butyl, 4- (cyclooctyl) butyl, 5- (cyclopropyl) pentyl, 5- (Cyclobutyl) pentyl, 5- (cyclopentyl) pentyl, 5- (cyclohexyl) pentyl, 5- (cycloheptyl) pentyl, 5- (cyclooctyl) pentyl, 6- (cyclopropyl) hexyl, 6- (cyclo Butyl) hexyl, 6- (cyclopentyl) hexyl, 6- (cyclohexyl) hexyl, 6- (cycle Cycloheptyl) hexyl or 6- (cyclooctyl) hexyl;

-C ₃ -C ₈ -cycloalkyloxy-C ₁ -C ₄ -alkyl: cyclopropyloxymethyl, 1-cyclopropyloxyethyl, 2-cyclopropyloxyethyl, 1-cyclopropyloxyprop-1-yl, 2-cyclopropyloxyprop-1-yl, 3-cyclopropyloxyprop-1-yl, 1-cyclopropyloxybut-1-yl, 2-cyclopropyloxybut-1-yl, 3-cyclopropyl Oxybut-1-yl, 4-cyclopropyloxybut-1-yl, 1-cyclopropyloxybut-2-yl, 2-cyclopropyloxybut-2-yl, 3-cyclopropyloxybut-2-yl , 4-cyclopropyloxybut-2-yl, 1- (cyclopropyloxymethyl) eth-1-yl, 1- (cyclopropyloxymethyl) -1- (CH ₃ ) eth-1-yl, 1- ( Cyclopropylmethyloxy) prop-1-yl, cyclobutyloxymethyl, 1-cyclobutyloxyethyl, 2-cyclobutyloxyethyl, 1-cyclobutyloxyprop-1-yl, 2-cyclobutyloxyprop -1-yl, 3-cyclobutyloxyprop-1-yl, 1-cyclobutyloxybut-1- 1, 2-cyclobutyloxybut-1-yl, 3-cyclobutyloxybut-1-yl, 4-cyclobutyloxybut-1-yl, 1-cyclobutyloxybut-2-yl, 2-cyclobutyl Oxybut-2-yl, 3-cyclobutyloxybut-2-yl, 4-cyclobutyloxybut-2-yl, 1- (cyclobutyloxymethyl) eth-1-yl, 1- (cyclobutyloxymethyl ) -1- (CH ₃ ) eth-1-yl, 1- (cyclobutyloxymethyl) prop-1-yl, cyclopentyloxymethyl, 1-cyclopentyloxyethyl, 2-cyclopentyloxyethyl, 1- Cyclopentyloxyprop-1-yl, 2-cyclopentyloxyprop-1-yl, 3-cyclopentyloxyprop-1-yl, 1-cyclopentyloxybut-1-yl, 2-cyclopentyloxy But-1-yl, 3-cyclopentyloxybut-1-yl, 4-cyclopentyloxybut-1-yl, 1-cyclopentyloxybut-2-yl, 2-cyclopentyloxybut-2-yl, 3-cyclopentyloxybut-2-yl, 4-cyclopentyloxybut-2-yl, 1- (cyclopentyloxymethyl) eth-1-yl, 1- (cyclopentyloxymethyl) -1- (C H ₃ ) Eth-1-yl, 1- (cyclopentyloxymethyl) prop-1-yl, cyclohexyloxymethyl, 1-cyclohexyloxyethyl, 2-cyclohexyloxyethyl, 1-cyclohexyloxyprop -1-yl, 2-cyclohexyloxyprop-1-yl, 3-cyclohexyloxyprop-1-yl, 1-cyclohexyloxybut-1-yl, 2-cyclohexyloxybut-1-yl , 3-cyclohexyloxybut-1-yl, 4-cyclohexyloxybut-1-yl, 1-cyclohexyloxybut-2-yl, 2-cyclohexyloxybut-2-yl, 3-cyclohexyloxy But-2-yl, 4-cyclohexyloxybut-2-yl, 1- (cyclohexyloxymethyl) eth-1-yl, 1- (cyclohexyloxymethyl) -1- (CH ₃ ) eth-1- 1, 1- (cyclohexyloxymethyl) prop-1-yl, cycloheptyloxymethyl, 1-cycloheptyloxyethyl, 2-cycloheptyloxyethyl, 1-cycloheptyloxyprop-1-yl, 2- Cycloheptyloxyprop-1-yl, 3-cycloheptyloxyprop-1-yl, 1-cycloheptyloxybut-1-yl, 2-cycloheptyloxybut- 1-yl, 3-cycloheptyloxybut-1-yl, 4-cycloheptyloxybut-1-yl, 1-cycloheptyloxybut-2-yl, 2-cycloheptyloxybut-2-yl, 3- Cycloheptyloxybut-2-yl, 4-cycloheptyloxybut-2-yl, 1- (cycloheptyloxymethyl) eth-1-yl, 1- (cycloheptyloxymethyl) -1- (CH ₃ ) -1-yl, 1- (cycloheptyloxymethyl) prop-1-yl, cyclooctyloxymethyl, 1-cyclooctyloxyethyl, 2-cyclooctyloxyethyl, 1-cyclooctyloxyprop-1-yl , 2-cyclooctyloxyprop-1-yl, 3-cyclooctyloxyprop-1-yl, 1-cyclooctyloxybut-1-yl, 2-cyclooctyloxybut-1-yl, 3-cyclo Octyloxybut-1-yl, 4-cyclooctyloxybut-1-yl, 1-cyclooctyloxybut-2-yl, 2-cyclooctyloxybut-2-yl, 3-cyclooctyloxybut-2- 1, 4-cyclooctyloxybut-2-yl, 1- (cyclooctyloxymethyl) eth-1-yl, 1- (cyclooctyloxymethyl) -1- (CH ₃ ) eth-1-yl, 1- (Cycloocta Oxymethyl) prop-1-yl, especially C ₃ C ₆ - cycloalkyl alkoxymethyl or 2- (C ₃ C ₆ - cycloalkyl-alkoxy) ethyl.

Three to seven membered heterocyclyls are saturated, partially or fully unsaturated heterocyclyls, as well as one to three selected from the group consisting of one to three carbon atoms, one or two oxygen and one or two sulfur atoms It is to be understood as meaning aromatic, heterocycles having heteroatoms.

Examples of saturated heterocycles that may contain carbonyl or thiocarbonyl ring members include oxiranyl, tyranyl, aziridin-1-yl, aziridin-2-yl, diaziridin-1-yl, diadia Ziridin-3-yl, oxetan-2-yl, oxetan-3-yl, thiethan-2-yl, thiethan-3-yl, azetidin-1-yl, azetidin-2-yl, azet Thidin-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothiophen-2-yl, tetrahydrothiophen-3-yl, pyrrolidin-1-yl, pyrroli Din-2-yl, pyrrolidin-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-dioxathiolan-2-yl, 1, 3-dioxathiolan-4-yl, 1,3-dioxathiolan-5-yl, 1,3-oxazolidin-2-yl, 1,3-osazolidin-3-yl, 1,3- Oxazolidin-4-yl, 1,3-oxazolidin-5-yl, 1,2-oxazolidin-2-yl, 1,2-oxazolidin-3-yl, 1,2-oxazoli Din-4-yl, 1,2-oxazolidin-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, pyrrolidin-1-yl, pyrroli Din-2-yl, pyrrolidine -5-yl, tetrahydropyrazol-1-yl, tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydro Pyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydropyran-4-yl, pepperin-1-yl, piperidin-2-yl, piperidine -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-oxatian-2-yl, 1,3-oxatian-4-yl, 1,3-oxatian-5-yl, 1,3-oxatian-6-yl , 1,4-oxatian-2-yl, 1,4-oxatian-3-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, hexahydropyridazine-1 -Yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydro Pyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl, piperazin-3-yl, hexahi Rho-1,3,5-triazin-2-yl, hexahydro-1,3,5-triazin-2-yl, oxepan-2-yl, oxepan-3-yl, oxepan-4- 1, thiepan-2-yl, thiepan-3-yl, thiepan-4-yl, 1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl, 1,3-diox Cepan-5-yl, 1,3-dioxepan-6-yl, 1,3-dithiepane-2-yl, 1,4-dioxepan-2-yl, 1,4-dioxepan-7-yl , Hexahydroazin-1-yl, hexahydroazin-2-yl, hexahydroazin-3-yl, hexahydroazin-4-yl, hexahydro-1,3-diazepin-1-yl , Hexahydro-1,3-diazepin-2-yl, hexahydro-1,3-diazepin-4-yl, hexahydro-1,4-diazepin-1-yl and hexahydro-1,4- Diazepin-2-yl and the like.

Examples of unsaturated heterocyclyls including carbonyl or thiocarbonyl ring members include dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl, 1 , 3-oxazolin-2-yl and the like.

Preferred among the heteroaromatic rings are 5-membered and 6-membered rings, and examples include furyls such as 2-furyl and 3-furyl, thienyl such as 2-thienyl and 3-thienyl, 2-pyrrolyl and 3-pyrrolyl Pyrrolyl, such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, and isothiazolyl such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl Pyrazolyl, such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl, such as 2-oxazolyl, 4-oxazolyl and 5-oxazolyl, 2-thiazolyl, 4-thiazolyl and 5 Thiazolyl such as thiazolyl, imidazole such as 2-imidazole and 4-imidazole, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and Oxdiazolyl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl and 1,3, such as 1,3,4-oxadiazol-2-yl Thiadiazolyl, such as 4-thiadiazol-2-yl, 1,2,4-thiazol-1-yl, 1,2,4-thiazol-3-yl and 1,2,4-thiazole-4 Pyrazinyl, such as thiazolyl, 2-pyridinyl, 3-pyridinyl, and 4-pyridinyl, pyridazinyl, 3-pyridazinyl, 2-pyrimidinyl, 4- Pyrimidinyl, such as pyrimidinyl and 5-pyriminidyl, also 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, in particular pyridyl , Pyrimidyl, furanyl and thienyl.

All phenyl, carboxyl and heterocyclic rings are preferably unsaturated.

Preferred for use as a herbicide of 3- (benzazol-4-yl) pyrimidinedione derivative I are compounds of formula I, wherein the variables have the following meanings, in each case alone or in combination.

X is hydrogen;

R ¹ is hydrogen, amino or C ₁ -C ₆ alkyl, in particular hydrogen or C ₁ -C ₄ alkyl, particularly preferably hydrogen or methyl;

R ² is hydrogen, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, or C ₁ -C ₆ alkylsulfonyl, in particular trifluoromethyl;

R ³ is hydrogen;

R ⁴ is hydrogen, fluorine or chlorine;

R ⁵ is cyano or halogen, in particular chlorine;

= Y- is = NN (R ⁶ )-or = C (ZR ⁷ ) -S-, in particular = NN (R ⁶ )-;

R ⁶ is C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkylsulfonyl, (C ₁ -C ₆ alkyl) carbonyl, (C _1- C ₆ alkyl) thiocarbonyl, (C ₁ -C ₆ alkoxy) carbonyl or cyano, (C ₁ -C ₆ alkoxy) carbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl or (C _1- C ₁ -C ₆ alkyl substitutable with C ₆ alkyl) carbonyloxy, in particular C ₁ -C ₆ alkyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkylsulfonyl or (C ₁ -C ₆ alkoxy Carbonyl,

Also particularly preferably 3- (benzazol-4-yl) pyrimidinedione derivative Ia {＾ = I, wherein X = oxygen, R ¹ = methyl, R ² = trifluoromethyl, R ³ = hydrogen, R ⁴ = fluorine, R ⁵ = chlorine and = Y- = = C (ZR ⁷ ) -N- (CH ₃ )-}, in particular compounds Ia.1-Ia.272 below.

Furthermore, particularly preferred 3- (benzazol-4-yl) pyrimidinedione derivatives are derivatives of the formulas Ib to Ih, in particular,

Compounds Ib.1 = Ib.272, different from the formulas Ia.1-Ia.272, corresponding only in that R ⁴ is hydrogen:

A compound Ic.1 = Ic.272 which differs from the formulas Ia.1-Ia.272 only corresponding in that R ¹ is hydrogen:

A compound Id.1 = Id.272 which differs from the formulas Ia.1-Ia.272 only corresponding in that R ¹ and R ⁴ are hydrogen

A compound Ie.1 = Ie.272 which differs from the formulas Ia.1-Ia.272 only corresponding in that = Y- is = C (ZR ⁷ ) -N (SO ₂ CH ₃ )-:

A compound different from Formulas Ia.1-Ia.272 If.1 = If.272, only corresponding that R ⁴ is hydrogen and = Y- is = C (ZR ⁷ ) -N (SO ₂ CH ₃ )-

A compound Ig.1 = Ig.272 which differs from the corresponding formulas Ia.1-Ia.272 only in that R ¹ is hydrogen and = Y- is = C (ZR ⁷ ) -N (SO ₂ CH ₃ )-

A compound Ih.1 = Ih which differs from the formulas Ia.1-Ia.272 only in that R ¹ and R ⁴ are hydrogen and = Y- is = C (ZR ⁷ ) -N (SO ₂ CH ₃ )- .272:

A compound Ii.1 = Ii.272 which differs from the formulas Ia.1-Ia.272 only corresponding to the fact that = Y- is = C (ZR ⁷ ) -O-:

A compound Ik.1 = Ik.272 which differs from the formulas Ia.1-Ia.272 only corresponding that = Y- is = C (ZR ⁷ ) -O- and R ⁴ is hydrogen:

c- A compound different from formulas Ia.1-Ia.272, wherein only = Y- is = C (ZR ⁷ ) -O- and R ¹ is hydrogen Im.1 = Im.272:

A compound In.1 = In.272 differing from the formulas Ia.1-Ia.272 only corresponding that = Y- is = C (ZR ⁷ ) -O- and R ¹ and R ⁴ are hydrogen;

The 3- (benzazol-4-yl) pyrimidinedione derivatives of formula (I) can be obtained in a variety of ways, for example by one of the following methods.

Method A):

Reaction of 3- (benzazol-4-yl) pyrimidinedione derivative I with compound II in which R ¹ is hydrogen in a known manner:

In the formula, L ¹ is halogen, preferably chlorine, bromine or iodine; (Halo) alkylsulfonyloxy, preferably methylsulfonyloxy or trifluoromethylsulfonyloxy; Arylsulfonyloxy, preferably toluenesulfonyloxy; And conventional leaving groups such as alkoxysulfonyloxy, preferably methoxysulfonyloxy or ethoxysulfonyloxy.

The process is usually carried out in an inert organic solvent, for example in a lower alcohol, preferably in a protonic solvent such as methanol or ethanol (as a mixture with water if desired), or for example methyl tert-butyl ether Aliphatic or cyclic ethers such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane; Aliphatic ketones such as acetone, diethyl ketone and ethyl methyl ketone; Amides such as dimethylformamide and N-methylpyrrolidone; Sulfoxides such as dimethyl sulfoxide; Ureas such as tetramethylurea and 1,3-dimethyltetrahydro-2 (1H) -pyrimidinone; Carboxylic acid esters such as ethyl acetate; Or aprotic solvents such as halogenated aliphatic or aromatic hydrocarbons such as dichloromethane, dichloroethane, chlorobenzene and dichlorobenzene.

If desired, the process can be carried out in the presence of a base, and suitable bases include, for example, carbonates such as sodium carbonate and potassium carbonate, hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, or sodium Inorganic bases such as alkali metal hydrides such as hydrides and potassium hydrides, and amines such as, for example, triethylamine, pyridine and N, N-diethylaniline, or sodium methoxide, sodium ethoxide and potassium tert- Organic bases such as alkali metal alkoxides such as butoxide.

The amount of base and alkylating agent II is preferably from 0.5 to 2 times the molar amount in each case, based on the amount of starting compound I, wherein R ¹ = hydrogen.

In general, the reaction temperature is from 0 ° C. to the boiling point of the reaction mixture, in particular from 0 ° C. to 60 ° C.

A preferred process variant is to alkylate the salt of I, obtained by cyclization of IV (here R ¹ = H) or V (here R ¹ = H) according to process D) without isolation from the reaction mixture, which is still an example. For example, it may contain an excess of base such as sodium hydride, sodium alkoxide or sodium carbonate.

If a salt of compound I, wherein R ¹ is hydrogen, cannot be prepared directly by cyclization under basic conditions as described in method D), it can also be obtained by known methods from the process product of methods C) to F). For this purpose, for example, an aqueous solution of an inorganic or organic base is treated with 3- (benzazol-4-yl) pyrimidinedione derivative I, wherein R ¹ = H. At this time, salt formation is usually sufficiently fast even at low temperatures of 20 to 25 ° C.

It is particularly advantageous to prepare sodium salts by dissolving 3- (benzazol-4-yl) pyrimidinedione derivative I (where R ¹ = H) in an aqueous sodium hydroxide solution at 20-25 ° C., wherein 3- (benzazole The 4-yl) pyrimidinedione derivative I (where R ¹ = H) and sodium hydroxide use about the same equivalents. The corresponding salt of 3- (benzazol-4-yl) pyrimidinedione derivative I can then be isolated, for example, by precipitation with a suitable inert solvent or by evaporation of the solvent.

Salts of 3- (benzazol-4-yl) pyrimidinedione derivatives I, in which the metal ions are other than alkali metal ions, can usually be prepared by double decomposition of the corresponding alkali metal salts in aqueous solution, ammonium, phosphonium, Sulfonium and sulfoxonium salts can be prepared with ammonia or phosphonium, sulfonium or sulfoxium hydroxides.

Course B)

Reaction of the electrophilic amination reaction with the 3- (benzazol-4-yl) pyrimidinedione derivative of formula I, wherein R ¹ = H, in the presence of a base:

Amination reactions which prove to be particularly suitable are 2,4-dinitrophenoxyamines, but it is also possible to use, for example, hydroxylamine-O-sulfonic acid (HOSA), which is previously known as amination reaction from the literature (eg See, E. Hofer et al., Synthesis 1983, 466, W. Friedrichsen et al., Heterocycles 20 (1983) 1271, H. Hart et al., Tetrahedron Lett. 25 (1984) 2073 , B. Vercek et al., Monatsh. Chem. 114 (1983) 789, G. Sosnousky et al., Z. Naturforsch. 38 (1983) 884, RS Atkinson et al., J. Chem. Soc. Perkin Trans. 1987, 2787).

The amination reaction can be carried out in a known manner (see, eg, T. Sheradsky, Tetrahedron Lett. 1968, 1909, MP Wentland et al., J. Med. Chem 27 (1984) 1103) and in particular EP-A 240 194, EP-A 476 697 and EP-A 517 181 to teach the amination of uracil).

The reaction is usually carried out in a polar solvent such as dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, or ethyl acetate, which has proved to be particularly suitable.

Suitable bases are, for example, alkali metal carbonates such as potassium carbonate, alkali metal alkoxides such as sodium methoxide and potassium tert-butoxide or alkali metal hydrides such as sodium hydride.

The amount of base and amination reactant is preferably 0.5 to 2 times the molar amount in each case based on the amount of starting compound.

Course C)

Sulfation reaction of 3- (benzazol-4-yl) pyrimidinedione derivatives of Formula I, wherein X = oxygen:

Generally, the sulfidation is carried out in an inert solvent or diluent, for example in aromatic hydrocarbons such as toluene and xylene, diethyl ether, 1,2-dimethoxyethane and organic amines such as pyridine or tetrahydrofuran. .

Particularly suitable sulfiding reagents include phosphorus (V) sulfide and 2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2,4-dithion ("Laweson reagent"). )to be.

Usually, 1 to 5 times the molar amount based on the starting material to be sulfided will be sufficient to substantially complete the reaction.

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

Course D)

Cyclization reaction of arylurea of formula III or arylanilide of formula IV in the presence of a base:

In the formula, L ² is lower alkyl, preferably C ₁ -C ₄ -alkyl, or phenyl.

Generally, the cyclization reaction is carried out in an inert organic solvent or diluent which is aprotic, for example aliphatic or cyclic ethers such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, aromatic solvents such as benzene or toluene, or It is carried out in a polar solvent such as dimethylformamide or dimethyl sulfoxide. Mixtures of polar solvents and hydrocarbons such as n-hexane are also suitable. Depending on the starting material, water may also be suitable as a diluent.

Suitable bases are preferably alkali metal alkoxides, especially sodium alkoxides; Alkali metal hydroxides, in particular sodium hydroxide and potassium hydroxide; Alkali metal carbonates, in particular sodium carbonate and potassium carbonate; Metal hydrides, in particular sodium hydride. When using sodium hydride as the base, it has proved advantageous to carry out the reaction in aliphatic or cyclic ethers, dimethylformamide or dimethyl sulfoxide.

Usually, 0.5 to 2 molar amounts of base, based on the amount of IV or V, will be sufficient to successfully carry out the reaction.

In general, the reaction temperature is from -78 ° C to the boiling point of the reaction mixture, in particular from -60 to 60 ° C.

When R ¹ in formula III or IV is hydrogen, the reaction product is obtained as a metal salt, which corresponds to the cation of the base used. The salts can be isolated and purified in a known manner or, if desired, can be converted by acid to give free compound I wherein R ¹ = hydrogen.

Course E)

Treatment of substituted 2-aminoaniline Va with nitrous acid

The cyclization can be carried out by known methods (see, for example, Houben-Weyl, Methoden der organischen Chemie (Methods in Organic Chemistry), Georg Thieme Verlag Stuttgart, Vol. E8d, 1st Edition 1994, pp. 409-415). ] Reference).

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

The nitrous acid is preferably prepared in-situ by adding alkali metal nitrite-as a substance or as an aqueous solution-to the reaction mixture, where it consists of an acidic aqueous solution or diaminobenzene in carboxylic acid.

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

The starting materials can be suitably used in approximately stoichiometric amounts, or the reaction can be carried out using nitrous acid in excess of 10 mol% in excess of the theoretically expected amount.

The following intermediates can be cyclized in a similar manner:

Course F)

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

The reaction of condensing the bifunctional benzene V with a carboxylic acid derivative or a carboxylic acid derivative is carried out in a manner known per se (see, for example, Houben-Weyl, Methoden der organischen Chemie (Methods in Organic Chemistry), Georg Thieme). Verlag Stuttgart, Vol. E8c, 1st Edition 1994, pp. 247-284; Vol. E8b, 1st Edition 1994, pp. 881-901; Vol. E8a, 1st Edition 1993, pp. 1032-1078). Preferred carboxylic acid derivatives or carboxylic acid derivatives are the corresponding anhydrides, acid chlorides, ortho esters, diimides, nitriles, trichloromethyl-substituted compounds, isocyanates and their thio analogs.

Suitable solvents / diluents are, in particular, organic solvents such as benzene, toluene and aromatic hydrocarbons such as o-, m-, p-xylene; Halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane; Lower alcohols such as methanol and ethanol; Aliphatic or cyclic ethers such as dimethoxyethane, tetrahydrofuran and dioxane; Carboxylic esters such as ethyl acetate; Or aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide.

If desired, a catalytic amount of acid can be added to accelerate the reaction. Suitable acids are, in particular, mineral acids such as hydrochloric acid or sulfonic acids such as p-toluenesulfonic acid. The amount of acid is preferably 0.1 to 5 mole%, based on the amount of V.

The reaction temperature is preferably 20 ° C. to the reflux temperature of the reaction mixture, in particular 60 ° C. to the reflux temperature.

Carboxylic acid derivatives or carboxylic acid derivatives are used in approximately stoichiometric amounts or in excess. If appropriate, too much excess may be used or the reaction may be carried out without solvent. Preferred is an approximately stoichiometric amount or an excess of up to 10 molar equivalents based on the amount of V.

Substituted 2-aminophenol, -thiophenol and -aniline (V) are appropriately obtained by reducing the corresponding 2-nitrophenol, -thiophenol or -aniline VIII (see, for example, Houben-Weyl, Methoden der organischen Chemie). (Methods in Organic Chemistry), Georg Thieme Verlag Stuttgart, Vol. XI / 1, 4th Edition 1957, p. 431 et seq.

Suitable reducing agents, in particular,

-Elemental metals such as iron, tin and zinc

Hydrogen in the presence of a suitable catalyst such as palladium or platinum or Raney nickel on charcoal, or

Complex hydrides such as LiAlH ₄ and NaBH ₄ with or without catalyst.

Depending on the reducing agent, suitable solvents are usually carboxylic acids such as acetic acid or propionic acid; Alcohols such as methanol and ethanol; Ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran and dioxane; Aromatic compounds such as benzene and toluene; And mixtures thereof.

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

Starting compounds are usually used in approximately stoichiometric amounts; In individual cases, however, up to about 10 mole% of excess of one or other components may also be advantageous.

2-nitrophenol, -thiophenol and aniline VIII can be liberated from the corresponding protective nitro compound IX:

Protectiveization = Conventional protecting groups protecting phenol or thiophenol with ethers or amino groups with amides.

Protecting groups can be removed by known methods (see, eg, Greene / Wuts: Protective Groups in Organic Synthesis, John Wiley & Sons, Inc., 2nd Edition 1991, p. 145 et seq. And p. 279 et seq. ] Reference).

Suitable removal reagents, in particular:

For alkylphenols: trimethylsilyl iodide, boron tribromide, boron trichloride, aluminum trichloride, lithium chloride or hydrogen bromide;

For unsubstituted or substituted benzylphenols or -thiophenols: precious metal catalysts such as boron trifluoride, hydrofluoric acid or hydrogen / catalysts, preferably palladium or platinum.

The solvent / diluent is preferably selected to be inert to the removal reagent. When using halides such as trimethylsilyl iodide, boron tribromide, boron trichloride or aluminum trichloride, halogenated solvents such as dichloromethane, chloroform, carbon tetrachloride and dichloroethane are particularly preferred. Hydrogen bromide is preferably used in aqueous solution, very particularly preferably as a 48% concentration solution; Lithium chloride is preferably used in polar solvents such as lower alcohols, dimethyl sulfoxide and dimethylformamide; The hydrocracking process is preferably carried out in lower alcohols or carboxylic acids, with or without addition of hydrogen transfer agents such as cyclohexene and cyclohexadiene.

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

The removal reagent is preferably used in an approximately stoichiometric amount or in excess. The excess is particularly preferably between 1 and 10 molar equivalents based on the amount of IX.

Finally, the protected nitro compound IX can be obtained in a known manner by nitrating (protected) phenol, thiophenol or aniline (see, eg, Houben-Weyl, Methoden der organischen Chemie (Methods in Organic Chemistry), Georg Thieme Verlag Stuttgart, Vol. 10/1, 1971, p. 479 et seq.

Suitable nitration reagents are, in particular, nitric acid, or nitronium salts, in particular nitronium tetrafluoroborate, as a mixture with sulfuric acid or acetic anhydride. The mixture consisting of nitric acid and sulfuric acid may consist of any desired weight ratio of the two components; Preferably sulfuric acid is a mixture which either predominates or acts as a solvent. Similarly, in the case of mixtures of nitric acid and acetic anhydride.

Nitronium tetrafluoroborate is preferably used in an aprotic polar solvent, for example acetonitrile or nitromethane.

The reaction temperature is generally -80 ° C to 80 ° C, in particular -20 ° C to 30 ° C.

When using nitric acid reagents in the nitration reaction, the reaction is preferably carried out with approximately the same molar amount or particularly preferably with an excess of nitration reagent. The excess may be several times the amount of X. Nitronium tetrafluoroborate is preferably used in the same molar amount compared to the substrate or in a slight excess between 1.1 and 1.5 molar equivalents.

The following intermediates can also be nitrated in a similar manner:

3- (benzazol-4-yl) pyrimidinedione derivatives of formula (I) having one or more chiral centers are usually obtained as enantiomers or diastereomeric mixtures, which if desired are for example crystallized or optically active It can be separated by methods commonly used for this purpose, such as chromatography on phosphorus adsorbents, to produce substantially pure isomers. Pure optically active isomers can be advantageously prepared from the corresponding optically active starting moles.

The 3- (benzazol-4-yl) pyrimidinedione derivatives of formula I, wherein R ¹ = H, can be converted to their salts in a known manner (see notes mentioned herein for process A).

The arylureas of formula III are novel. They can be prepared by methods known per se, for example, one of the following methods:

Course G)

Reaction of β-ketocarboxylic acid ester XIII with urea XIV:

L ² in the formula is lower alkyl, preferably C ₁ -C ₄ -alkyl, or phenyl.

This process is preferably carried out under substantially anhydrous conditions in an inert solvent or diluent, particularly preferably in the presence of an acidic or basic catalyst.

Suitable solvents or diluents are, in particular, organic solvents which are miscible with water to give an azeotropic mixture, for example aromatics such as benzene, toluene and o-, m-, p-xylene, methylene chloride, chloroform, carbon tetrachloride and Halogenated hydrocarbons such as chlorobenzene, aliphatic and cyclic ethers such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or cyclohexane, but alcohols such as methanol and ethanol are also possible.

Suitable acidic catalysts are preferably strong mineral acids such as sulfuric acid and hydrochloric acid, phosphorus-containing acids such as orthophosphoric acid and polyphosphoric acid, organic acids such as p-toluenesulfonic acid, and "Amberlyst 15" (Fluka). Acidic cation exchanger).

Examples of suitable basic catalysts are alkali metal hydrides such as sodium hydride and particularly preferably alkali metal alkoxides such as sodium methoxide and sodium ethoxide.

XIV and β-ketocarboxylic acid ester XIII are suitably used in approximately stoichiometric amounts or are carried out with one or another component in a slight excess of up to about 10 mole%.

A catalyst in an amount of 0.5 to 2 mole percent, based on the amount of one of the starting compounds, will usually be sufficient.

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

Course H)

Reaction of Enol Ether XV with Urea XVI:

L ² and L ³ in each case are lower alkyl, preferably C ₁ -C ₄ -alkyl, or phenyl.

The reaction is preferably carried out in an inert organic solvent which can be miscible with water, for example in aliphatic or cyclic ethers such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or in lower alcohols, in particular ethanol The reaction temperature is usually 50 to 100 ° C., preferably the boiling point of the reaction mixture.

However, the reaction may also be carried out in aromatic diluents such as benzene, toluene and o-, m-, p-xylene, in which case acidic catalysts such as hydrochloric acid and p-toluenesulfonic acid or for example sodium methoxide and sodium It is recommended to add a base such as an alkali metal alkoxide such as ethoxide. In this process variant, again, the reaction temperature is usually between 50 and 100 ° C, preferably between 60 and 80 ° C.

As for the weight ratio, what is mentioned with respect to method G) also applies here.

Course J)

Reaction of Enaminoester XVII with Isocyanate XVIII:

L ² in the formula is lower alkyl, preferably C ₁ -C ₄ -alkyl, or phenyl.

The reaction is substantially anhydrous aprotic organic solvents or diluents, for example aliphatic or cyclic ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, n-hexane, benzene, toluene and aliphatic or aromatic hydrocarbons such as o-, m-, p-xylene, halogenated aliphatic hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene, dimethylformamide, hexamethyl phosphoric triamide and dimethyl Suitably in the presence of an aprotic polar solvent such as sulfoxide, or mixtures thereof.

If desired, the process may be carried out in the presence of metal hydride bases such as sodium hydride and potassium hydride, or organic tertiary bases such as triethylamine and pyrimidine, and it is possible for the organic base to act simultaneously as a solvent. .

The starting materials are suitably used in stoichiometric amounts, or the process is carried out in small excess of one or other components of up to about 10 mol%. If the process is carried out in the presence of an organic base and in the absence of a solvent, the organic base will be present in large excess.

The reaction temperature is preferably -80 to 50 ° C, in particular -60 to 30 ° C.

In a particularly preferred embodiment, the resulting enamine ester III is converted directly to the excess base (ie “in situ”) according to process D) to give the corresponding product of I.

Course K)

Reaction of Enaminoester XVII with Urethane XIX:

In the formula, L ² and L ⁴ are independently of each other lower alkyl, preferably C ₁ -C ₄ -alkyl, or phenyl.

This reaction is advantageously carried out in aprotic polar solvents or diluents such as dimethylformamide, 2-butanone, dimethyl sulfoxide and acetonitrile, advantageously having a base such as an alkali metal alkoxide or an alkaline earth metal alkoxide, in particular sodium methoxide Suitably in the presence of sodium alkoxides, alkali metal carbonates or alkaline earth metal carbonates, especially sodium carbonate, or alkali metal hydrides such as lithium hydride and sodium hydride.

One or two molar moles of base based on the amount of XVII or XIX will usually be sufficient.

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

Regarding the weight ratio of the starting compounds, what is said about method G) also applies here.

In a particularly preferred embodiment, sodium alkoxide is used as the base, and the alcohol formed during the reaction is continuously distilled off. The resulting enaminoester IV can be cyclized according to process D) without isolation from the reaction mixture to produce a salt of substituted benzothiazole I, wherein R ¹ = H.

Urethane XIX can, for example, be prepared from carbonyl chloride XX and aniline XXI:

In order to avoid excess aniline, it is generally necessary to add auxiliary bases such as triethylamine, pyridine or alkali metal carbonate to capture the hydrogen chloride formed during the reaction. Pyridine is particularly suitable because it can be used simultaneously as a solvent.

Suitable solvents / diluents other than pyridine are, in particular, aromatic hydrocarbons such as benzene, toluene and o-, m-, p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane, lower alcohols such as methanol and ethanol, dimethicone Aliphatic or cyclic ethers such as methoxyethane, tetrahydrofuran and dioxane, carboxylic acid esters such as ethyl acetate, or aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide.

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

Starting materials are suitably used in approximately stoichiometric amounts, or excess carbonyl chloride of up to 10 mol% is selected.

Auxiliary bases are usually used in approximately equivalent molar amounts based on the amount of XX or XXI, or in excess of up to about twice the molar amount. If pyridine is used as the auxiliary base, more excess is also recommended, in which case the process can be carried out without additional solvent.

Course L)

Reaction of isocyanate XXII with aniline derivative XXI:

L ² is lower alkyl, preferably C ₁ -C ₄ -alkyl, or phenyl.

This reaction is carried out in substantially anhydrous aprotic organic solvents or diluents, for example aliphatic or cyclic ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, n-hexane, benzene, Aliphatic or aromatic hydrocarbons such as toluene and o-, m-, p-xylene, halogenated aliphatic hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene, dimethylformamide, hexamethyl phosphoric triamide And aprotic polar solvents such as dimethyl sulfoxide, or mixtures thereof.

If desired, the process can be carried out with metal hydride bases such as sodium hydride and potassium hydride, alkali or alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide, or triethylamine and pyrimidine It can be carried out in the presence of an organic nitrogen base, and it is possible for the organic base to act simultaneously as a solvent.

The starting materials are suitably used in approximately stoichiometric amounts, or one of the components is carried out in excess of up to about 20 mol%. If the process is carried out in the presence of an organic base and in the absence of a solvent, the organic base will be advantageously present in a greater excess.

The reaction temperature is generally from -80 to 150 ° C, preferably from -30 ° C to the boiling point of the reaction mixture.

Arylanilides of formula IV are also novel; They can also be prepared in a known manner, for example by reacting amide XXIII with urethane XXIV according to process M):

L ² is lower alkyl, preferably C ₁ -C ₄ -alkyl, or phenyl.

This reaction is advantageously carried out under atmospheric pressure in substantially an aprotic solvent / diluent, particularly preferably in the presence of an acidic catalyst.

To prepare enamine carboxylate IV, wherein R ¹ = amino, it is recommended to use compound XXIV with an amino group protected (eg as hydrazone).

Suitable solvents / diluents are, in particular, organic emulsions which can be mixed with water to give an azeotropic mixture, for example aromatics such as benzene, toluene and o-, m-, p-xylene, or carbon tetrachloride and chlorobenzene Halogenated hydrocarbons.

Suitable catalysts are, in particular, strong mineral acids such as sulfuric acid, organic acids such as p-toluenesulfonic acid, phosphorus-containing acids such as orthophosphoric acid and polyphosphoric acid, or acidic cation exchangers such as "amberlist 15" (fluka) to be.

In general, a reaction temperature of about 70 to 150 ° C. is sufficient; However, in order to quickly remove the water produced in the reaction, the process is properly carried out at the boiling point of the reaction mixture.

XXIII and XXIV are usually used in approximately stoichiometric amounts; Preferably, XXIV is used in a slight excess of up to about 20 mole percent.

Amide XXIII can be prepared as follows (process N)):

The reaction is preferably carried out in anhydrous inert aprotic solvents, for example halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and chlorobenzene, benzene, toluene and aromatic hydrocarbons such as o-, m-, p-xylene, or diethyl It is carried out in aliphatic or cyclic ethers such as ether, dibutyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane.

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

XXV and XXI are usually used in approximately stoichiometric amounts, or one of the components is used in excess of up to about 10 mole percent.

Isocyanate XVIII can be obtained, for example, from the aniline derivative XXI according to process O):

The process can be carried out in an inert, substantially anhydrous solvent or diluent, or without solvent, and the aniline derivative XXI is preferably used with "phosphene equivalents" such as phosgene, diphosgene, triphosgene and carbonyldiimidazole. Or trichloromethyl chloroformate.

Suitable solvents or diluents are, in particular, aprotic organic solvents such as dimethylformamide or toluene and aromatics such as o-, m-, p-xylene, methylene chloride, chloroform, 1,2-dichloroethane and chlorobenzene Aliphatic or cyclic ethers such as halogenated hydrocarbons, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or esters such as ethyl acetate, and mixtures thereof.

Starting materials are suitably used in approximately stoichiometric amounts, or one of the components is used in excess of up to about 200 mole percent.

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

The reaction temperature is generally from -20 ° C to the reflux temperature of the solvent or reaction mixture.

The aniline derivative XXI can, in turn, be obtained in a manner known per se by reducing the nitro derivative XXVI (for example, Houben-Weyl, Methoden der organischen Chemie (Methods in Organic Chemistry), Georg Thieme Verlag Stuttgart, Vol. .XI / 1, 4th Edition 1957, p. 431 et seq.].

With regard to reducing agents, solvents, reaction temperatures and weight ratios, reference may be made to those mentioned for process F) above.

Compounds XXVIII and XXI may also contain one or more chiral centers, in which case they are usually obtained as a mixture of enantiomers or diastereomers. If desired, the mixture may be separated into substantially pure isomers by methods commonly used for this purpose, such as, for example, crystallization or chromatography on optically active adsorbents. Pure optically active isomers may also be prepared, for example, from the corresponding optically active starting materials.

Unless otherwise specified, all of the above processes are carried out under atmospheric pressure or under the inherent pressure of the reaction mixture. Generally, the reactants are used in molar ratios of 0.95: 1 to 5: 1.

In general, the reaction mixture is in a manner known per se, for example by diluting the reaction solution with water and then isolating the product by filtration, crystallization or solvent extraction, or removing the solvent, residual in a mixture of water and a suitable organic solvent. The work-up is performed by distributing water and working up the organic layer to produce the product.

Compound I and its agriculturally useful salts are suitable as herbicides, both in the form of isomeric mixtures and pure isomers. Herbicide compositions comprising I have the effect of very well controlling plant growth in non-cultivated areas, especially when applied at high rates. In crops such as wheat, rice, corn, soybeans and cotton, they work against broadleaf weeds and grass weeds without causing substantial harm to cultivated plants. This effect is mainly observed in low ratio applications.

Depending on the method of application, Compound I or herbicidal compositions comprising the same may be used in a larger number of cultivated plants to remove undesirable plants. Examples of suitable crops are as follows: alium sepa, ananas comosus, arachis hippogagia, asparagus opininalis, beta vulgaris spec. Altishima, Beta Bulgarias Specs. Rapha, Brassica Napus Bar. Napus, Brassica Napus Bar. Napo Brassica, Brassica Rafa Bar. Silvestris, Camellia sinensis, Carthamus tinctorius, Karya illinoinsis, citrus limon, citrus sinensis, copea arabica (copea canepora, copea riberica), cucumis satibus, cynodon Dactilone, Doucus Carota, Ellace Guininsis, Pragaria Besca, Glycine Max, Gossipium Hirthumum, (Gossipium Arboreum, Gossipium Herbaceum, Gossipibitifolium), Helianthus Annuus, Hevea Brasiliensis, Hordeum Bvlgari, Humulus Lupulus, Ipomoea Batatas, Juglanz Regia, Lance Culinarys, Rium Ushitatimumm, Ricopersicone Lycofericum, Malus Spec., Manihot Esculenta, Medicago Sativa, Musa Spec., Nicotiana Tabacum (N. Rustica), Olea Europaa, Oriza Sativa, Paseolus Lunatus, Paseolus Vulgaris, P Abies, Pinus Spec., Pisum Sativa, Prunus Abium, Prunus Persica, Pirrus Communis, Rives Sylvester, Ricinus Communis, Sakarum Officinarum, Cecale Cereale, Solanum Tuberosum, Sorghum Vicolo (S. Bulgari), Theobroma Cacao, Tripolium Pratense, Triticum Astiboom, Triticum Durum, Bisia Pava, Vitis Vinifera and Zea Mys.

In addition, the compound I can also be used in crops that have developed resistance to the action of herbicides by breeding, including genetic engineering methods.

Compound I or herbicidal compositions comprising the same are, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreads or particulates Furnace, spray, spray, dusting, spread or injection can be used. The form of use depends on the intended purpose; In all cases, the finest possible distribution of the active ingredient according to the invention should be ensured.

Suitable inert auxiliaries are substantially the mineral oil portions of medium to high boiling media, such as kerosine and diesel oils, as well as coal tar oils and oils of vegetable or animal origin, for example paraffin, tetrahydronaphthalene, alkylated naphthalene and their Aliphatic, cyclic and aromatic hydrocarbons such as derivatives, alkylated benzenes and derivatives thereof, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, amines such as N-methylpyrrolidone and water Strong polar solvents such as

Aqueous use forms can be prepared from particulates dispersible in water by the addition of emulsion concentrates, suspensions, pastes, wettable powders or water. To prepare emulsions, pastes or oil dispersions, the substance itself or the substance dissolved in oil or solvent may be homogenized in water by wetting agents, tackifiers, dispersants or emulsifiers. Alternatively, concentrates consisting of the active substances, wetting agents, tackifiers, dispersants or emulsifiers and, where appropriate, solvents or oils can be prepared, which concentrates are suitable for dilution with water.

Suitable surfactants include aromatic sulfonic acids (eg ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid), fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates Alkali metal salts, alkaline earth metal salts and ammonium salts, and salts of sulfated hexa-, hepta- and octadecanol, and fatty acid alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, naphthalene or naphthalenesulfonic acid and phenols And condensates of formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl-, octyl- or nonylphenols, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohols, Fatty acid alcohol / ethylene oxide condensates, ethoxylated caster oils, polyoxyethylene alkyl ethers or polyox Propylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste is a liquid or methylcellulose.

Powders, spreading materials and dusts can be prepared by mixing or bonding the active materials with a solid carrier.

Fines (eg coated fines, impregnated fines and homogeneous fines) can be prepared by binding the active ingredient to a solid carrier. Solid carriers include silica, silica gel, silicate, talc, kaolin, limestone, lime, chalk, church clay, ocher, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, powdered synthetic materials ( ground synthetic material), fertilizers such as ammonium sulphate, ammonium phosphate, ammonium nitrate, urea, and botanical products such as grain flour, bark flour, wood flour and nutshell flour, cellulose powder, or other solid carriers.

The concentration of the active ingredient I in the preparations ready for use can vary within wide ranges. In general, the formulation comprises about 0.001 to 98% by weight, preferably 0.01 to 95% by weight of one or more active ingredients. The active ingredient is used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

The following formulation examples illustrate the preparation of such a product:

I. 20 parts by weight of compound 1 was prepared by adding 80 parts by weight of alkylated benzene, 10 parts by weight of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid N-monoethanolamide, and 5 parts by weight of calcium dodecylbenzenesulfonate. And 5 parts by weight of an adduct of 40 moles of ethylene oxide and 1 mole of castor oil. The solution is poured into 100,000 parts by weight of water and finely distributed therein to produce an aqueous dispersion comprising 0.02% by weight of active ingredient.

II. 20 parts by weight of compound No. 2 was prepared by 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of 7 moles of ethylene oxide and 1 mole of isooctylphenol, and 1 mole by 40 moles of ethylene oxide. Is dissolved in a mixture consisting of 10 parts by weight of the adduct of castor oil. The solution is poured into 100,000 parts by weight of water and finely distributed to produce an aqueous dispersion comprising 0.02% by weight of active ingredient.

III. 20 parts by weight of the active ingredient No. 4 is a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction having a boiling point of 210 to 280 ° C. and 10 parts by weight of an addition of 40 moles of ethylene oxide and 1 mole of castor oil. Dissolve in The solution is poured into 100,000 parts by weight of water and finely distributed to produce an aqueous dispersion comprising 0.02% by weight of active ingredient.

IV. 20 parts by weight of the active ingredient No. 6 is thoroughly mixed with 3 parts by weight of sodium diisobutylnaphthalene-α-sulfonate, 17 parts by weight of lignosulfonic acid sodium salt from the sulfite waste solution and 60 parts by weight of powdered silica gel, and the mixture is Mill with a hammer mill. The mixture is finely distributed in 20,000 parts by weight of water, producing a spray mixture comprising 0.1% by weight of active ingredient.

V. 3 parts by weight of active ingredient No. 8 is mixed with 97 parts by weight of finely divided kaolin. This produces a dust comprising 3% by weight of active ingredient.

VI. 20 parts by weight of active ingredient No. 12 is closely related to 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. Mix. This produces a stable oily dispersion.

VII. 1 part by weight of compound No. 14 is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. The mixture can be serially diluted with water to produce the active ingredient of the desired concentration. This yields a stable emulsion concentrate.

VIII. 1 part by weight of compound 19, 80 parts by weight of cyclohexanone and Wetolol 31 (Wettol EM 31 = nonionic emulsifier based on ethoxylated castor oil; BASF AG) is dissolved in a mixture of 20 parts by weight. The mixture can then be diluted with water to produce the active ingredient in the desired concentration. This yields a stable emulsion concentrate.

The active ingredient I or herbicidal composition can be applied in pre- or post-emergency. If a cultivated plant does not tolerate the active ingredient well, spray the herbicidal composition with the help of a spray device in such a way that it reaches the undesirable leaves or bare soil surfaces that grow below, while avoiding contact with the leaves of sensitive cultivated plants. (Post-orientation, lay-by).

Depending on the control target, season, target plant and growth stage, the application rate of active ingredient I is from 0.001 to 3.0, preferably from 0.01 to 1.0 kg / ha active substance (a.s.).

To broaden the range of action and achieve synergism, 3- (benzazol-4-yl) pyrimidinedione derivatives I can be mixed and applied with a large number of other herbicidal or growth-regulating active ingredient groups. Suitable components for the mixture are, for example, 1,2,4-thiadiazole, 1,3,4-thiadiazole, amides, aminophosphoric acid and derivatives thereof, aminotriazoles, anilides, aryloxy / heteroaryloxyalka Nosane and its derivatives, benzoic acid and its derivatives, benzothiadiazinone, 2- (heteroyl / aroyl) -1,3-cyclohexanedione, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF _3- Phenyl derivatives, carbamate, quinolinecarboxylic acid and derivatives thereof, chloroacetanilide, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid and derivatives thereof, dihydrobenzofuran, dihydrofuran-3-one, Dinitroaniline, dinitrophenol, diphenyl ether, dipyridyl, halocarboxylic acid and derivatives thereof, urea, 3-phenyluracil, imidazole, imidazolinone, N-phenyl-3,4,5,6 Tetrahydrophthalimide, oxadiazole, oxirane, phenol, aryloxy- and heteroaryloxy Phenoxypropion ester, phenylacetic acid and derivatives thereof, 2-phenylpropionic acid and derivatives thereof, pyrazole, phenylpyrazole, pyridazine, pyridinecarboxylic acid and derivatives thereof, pyrimidyl ether, sulfonamide, sulfonylurea, triazine , Triazinone, triazolinone, triazolecarboxamide and uracil.

It may also be advantageous to apply Compound I alone or in combination with other herbicides, and also as a mixture with other crop protection agents, for example insecticides or phytopathogenic fungi or bacterial control agents. Compatibility with mineral salt solutions used to treat nutrient and trace element deficiencies is also important. Non-plant-toxic oils and oil concentrates may also be added.

Preparation Example:

Example 1

3- [7-chloro-5-fluoro-1-methyl-1H-benzotriazol-4-yl] -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (Compound 2)

0.12 g of methyl iodide was mixed at 20 ° C. with 0.25 g of 3- [7-chloro-5-fluoro-1-methyl-1H-benzotriazol-4-yl] -6-trifluoromethyl-2,4 ( 1H, 3H) -pyrimidinedione, 0.12 g of potassium carbonate and 20 ml of anhydrous dimethylformamide was added dropwise. The reaction mixture was subsequently stirred for an additional 18 hours and then treated with 50 ml of water. The mixture was then extracted three times with 20 ml of ethyl acetate in each case. 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 (eluant: cyclohexane / ethyl acetate = 1: 1). Yield: 0.07 g;

Example 2

3- [7-chloro-5-fluoro-1-methyl-1H-benzotriazol-4-yl] -6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione (Compound 1 )

0.43 g of ethyl 3-amino-4,4,4-trifluorobut-2-enoate in 3 ml of dimethylformamide was added to 0.13 in 7 ml of anhydrous dimethylformamide at 0 ° C. over 15 minutes under nitrogen atmosphere. to g sodium methoxide. The mixture was first stirred at 10 ° C. for an hour and a half followed by a solution of 0.57 g of ethyl 7-chloro-5-fluoro-1-methyl-1H-benzotriazol-4-ylcarbamate in 20 ml of dimethylformamide. It was added dropwise to the reaction mixture over 15 minutes. The mixture was then heated to 20 ° C. and stirring continued for 5 minutes. The mixture was then heated to 60 ° C. and 0.35 g of 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) was added. Finally, stirring was continued for 4 hours at 120 ° C and 18 hours at 20 ° C.

For work-up, the mixture was poured into 100 ml of 10% aqueous potassium carbonate solution. The valuable product was extracted with diethyl ether (2 times 50 ml) and the remaining aqueous layer was brought to pH 1 with hydrochloric acid and then extracted with ethyl acetate (30 ml 3 times).

The mixed organic layer was then washed with about 20 ml of saturated aqueous sodium chloride solution and 30 ml of 10% by weight aqueous lithium chloride solution, then dried over sodium sulfate and finally concentrated. Yield: 0.25 g;

Step 2.1

2-chloro-4-fluoro-N-trifluoroacetylaniline

144.3 g of trifluoroacetic anhydride in 150 ml of diethyl ether was added dropwise at 0 ° C. to 100 g of 2-chloro-4-fluoroaniline in 800 ml of anhydrous diethyl ether. After the mixture was heated to 20 ° C., 500 ml of water were added. The organic layer was separated, washed three times with water, dried over sodium sulfate and finally concentrated. Yield: 151.5 g;

Step 2.2

3-chloro-5-fluoro-2N-trifluoroacetylaminonitrobenzene

375 ml of 98% strength nitric acid was slowly added dropwise to 75 g of 2-chloro-4-fluoro-N-trifluoroacetylaniline in 753 ml of acetic anhydride at -5 ° C. The mixture was then stirred at -5 ° C for one hour and then heated to 20 ° C. The course of the reaction was monitored by high pressure liquid chromatography on RP ¹⁾ -18 column (eluant: acetonitrile / water = 7: 3). As soon as the starting material was no longer detected, the reaction mixture was poured into ice-cold saturated aqueous sodium chloride solution. The valuable solid product was subsequently separated off, washed with water and dried for several hours in a drying oven at 20 ° C. under reduced pressure. Yield: 62.3 g;

¹⁾ reverse phase, silica gel phase

Step 2.3

3-Chloro-5-fluoro-2- (N-methyl-N-trifluoroacetylamino) -nitrobenzene

12.0 g of methyl iodide was added to a mixture of 16.1 g of 3-chloro-5-fluoro-2N-trifluoroacetylaminonitrobenzene, 11.6 g of potassium carbonate and 100 ml of anhydrous dimethylformamide. The reaction mixture was then stirred at 20 ° C. for 18 h and then 500 ml of water were added. The mixture was then extracted three times with 100 ml of ethyl acetate each. The mixed organic layer was dried over sodium sulfate and finally concentrated.

Yield: 16.3 g;

Step 2.4

3-chloro-5-fluoro-2-methylaminonitrobenzene

173 ml of 1-normal sodium hydroxide solution was added to 16.3 g of 3-chloro-5-fluoro-2- (N-methyl-N-trifluoroacetylamino) nitrobenzene solution in 173 ml of ethanol. The mixture was then stirred for 1 hour and then diluted with 500 ml of water. Then extracted three times with 80 ml of ethyl acetate. The mixed organic layer was washed with water, dried over sodium sulfate and finally concentrated. Yield: 10.1 g;

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 of absolute ethanol. The mixture was then heated to 50 ° C. and 0.94 g of sodium borate in 55 ml of absolute ethanol was added dropwise in such a way that the temperature of the mixture did not exceed 60 ° C. For work-up, the mixture was poured into 1 l of ice water and brought to pH 14 with sodium hydroxide solution. The mixture was then extracted three times with 100 ml of tert-butyl methyl ether. The combined organic layers were washed with water, dried over sodium sulfate and finally concentrated. Yield: 7.5 g;

Step 2.6

7-chloro-5-fluoro-1-methylbenzotriazole

A solution of 3.25 g sodium nitrite in 19 ml of water was added at 5 ° C. to 7.5 g of 2-amino-6-chloro-4-fluoro-N-methylaniline in 117 ml of 10% strength hydrochloric acid. The reaction mixture was stirred at 5 ° C. for one hour and then diluted with 200 ml of water. The solid was then separated off, washed with 3 x 50 ml of water and vacuum dried in a vacuum drying oven at 20 ° C. Yield: 7.2 g;

Step 2.7

7-chloro-5-fluoro-1-methyl-4-nitrobenzotriazole

0.65 ml of 98% strength nitric acid was slowly added dropwise to 1.5 g of 7-chloro-5-fluoro-1-methylbenzotriazole in 28 ml of concentrated sulfuric acid at -20 ° C. The mixture was then stirred at 0 ° C. for one hour and then heated to 20 ° C. Agitation was then continued for 18 hours, and the reaction mixture was then poured into 500 ml of ice water. The solid was separated, washed with water and dried in a 20 ° C. vacuum drying oven. Yield: 1.66 g;

Step 2.8

4-amino-7-chloro-5-fluoro-1-methylbenzotriazole

1.66 g of 7-chloro-5-fluoro-1-methyl-4-nitrobenzotriazole was reduced to tin dichloride / sodium borate in a similar manner as in step 2.5. Yield: 1.27 g;

Step 2.9

Ethyl 7-chloro-5-fluoro-1-methyl-1H-benzotriazol-4-ylcarbamate

2.28 g of ethyl chloroformate was slowly added dropwise to 13 ml of anhydrous pyridine at 0 ° C., and then the mixture was stirred at this temperature for 15 minutes. Then, 1.27 g of 4-amino-7-chloro-5-fluoro-1-methylbenzotriazole in 20 ml of pyridine was added dropwise at 0 ° C. Stirring was then continued at 0 ° C. for the first 30 minutes, then 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. The mixture was then extracted three times with 50 ml of tert-butyl methyl ether. The mixed organic layer was washed with 100 ml of water and then concentrated. 50 ml of diethyl ether was added to the residue. The undissolved components were separated and washed with 3 x 30 ml of diethyl ether. The mixed ether layer was concentrated. Yield: 0.37 g;

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 I.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 in a similar manner as in Example 1. The crude product was purified by chromatography on silica gel (eluant: cyclohexane / ethyl acetate = 2: 1). Yield: 1.4 g;

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 is 0.5 g of 3- [7-chloro-5-fluoro-1-methyl-2-trifluoromethyl-1H-benzimidazol-4-yl ] -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione, 2.35 g of potassium carbonate and 5 ml of ethyl acetate mixture were added. The mixture was stirred at 20 ° C. for 18 h and then diluted with 50 ml of ethyl acetate. The resulting mixture was washed with 3 x 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;

Example 5

3- [7-chloro-5-fluoro-1-methyl-2-trifluoromethyl-1H-benzimidazol-4-yl] -6-trifluoromethyl-2,4 (1H, 3H)- Pyrimidinedione (Compound 4)

4.31 g of ethyl 3-amino-4,4,4-trifluorobut-2-enoate in 20 ml of dimethylformamide was added to 0.82 g of sodium hydride in 50 ml of anhydrous dimethylformamide at 0-5 ° C. Added dropwise. The mixture was then stirred at the same temperature for 1 hour and then 7-chloro-5-fluoro-4-isocyanato-1-methyl-2-trifluoromethylbenzimidazole in 40 ml of dimethylformamide ( From step 5.4) was added at -30 ° C. Stirring was continued for 1 hour at -30 ° C and further 1 hour at 20 ° C. For work-up, the reaction mixture was carefully poured into 200 ml of ice water. Acidification with 10% strength hydrochloric acid gave a solid which was filtered, washed with water and dried in a vacuum drying oven at 20 ° C. After purification by flash chromatography (eluant: cyclohexane / ethyl acetate = 2: 1), 5.08 g of valuable product were obtained.

After the solids have been separated off, the filtrate is extracted three times with 200 ml of tert-butyl methyl ether and the mixed ether layers are washed and dried over sodium sulphate to concentrate the valuable products still remaining in the filtrate (2.46 g). Isolated.

Total yield: 7.54 g;

Step 5.1

7-chloro-5-fluoro-1-methyl-2-trifluoromethylbenzimidazole

15.5 g of 3-chloro-5-fluoro-2- (N-methyl-N-trifluoroacetylamino) nitrobenzene (step 2.3) in a tin dichloride / without isolating intermediates in a similar manner as in step 2.5 Reduction with sodium boronate gave the corresponding amino compound, which spontaneously cyclized upon removal of water to yield a valuable product. Yield: 9.32 g;

Step 5.2

7-chloro-5-fluoro-1-methyl-4-nitro-2-trifluoromethylbenzimidazole

46.3 ml of 98% strength nitric acid was slowly added dropwise to 9.65 g of 7-chloro-5-fluoro-1-methyl-2-trifluoromethyl-benzimidazole in 96.5 ml of acetic anhydride at 0 ° C. The mixture was stirred at 0 ° C. for 1 h and then carefully heated to 20 ° C. (When the exothermic reaction started, the temperature was kept below 25 ° C. by an ice bath.) The reaction mixture was first stirred for a further 2 hours at 20 ° C. successively and then poured into an ice-cold saturated aqueous sodium chloride solution. The solid formed was separated, washed with water and dried at 20 ° C. in a vacuum drying oven. Yield: 8.5 g;

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-trifluoromethyl-benzimidazole were reduced by tin dichloride / sodium borate in a similar manner as in step 2.5. Yield: 6.3 g;

Step 5.4

7-chloro-5-fluoro-4-isocyanato-1-methyl-2-trifluoromethyl-benzimidazole

23.32 g of diphosgene was added to 6.3 g of 4-amino-7-chloro-5-fluoro-1-methyl-2-trifluoromethylbenzimidazole in 100 ml of anhydrous toluene. The mixture was subsequently refluxed for 6 hours in succession. The reaction mixture was further stirred at 20 ° C. for 18 h and then concentrated. The crude product obtained was reacted directly without purification to give the final product I.4.

Example 6

3- [7-chloro-1,2-dimethyl-5-fluoro-1H-benzimidazol-4-yl] -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyri Middinedione (Compound 8)

0.33 g of 3- [7-chloro-1,2-dimethyl-5-fluoro-1H-benzimidazol-4-yl] -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidine Dione was alkylated with methyl iodide in a similar manner as in Example 1. Yield: 0.04 g;

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 from step 7.4 was prepared in a similar manner as in Example 5 to ethyl 3-amino-4,4,4-trifluoro React with lobut-2-enoate. The crude product was purified by medium pressure liquid chromatography (eluent: ethyl acetate / methanol = 15: 1). Yield: 0.7 g;

Step 7.1

7-chloro-1,2-dimethyl-5-fluorobenzimidazole

100 ml of 10% strength hydrochloric acid was added to 6.96 g 2-amino-6-chloro-4-fluoro-N-methylaniline (from step 2.5) in 4.1 g acetic anhydride. The mixture was then refluxed for 4 hours. After cooling, the mixture was taken in ice water. Then it was carefully neutralized with an aqueous sodium carbonate solution. The solid crude product that formed was separated, washed with water and dried in a vacuum drying oven at 20 ° C. Yield: 7.92 g;

Step 7.2

7-chloro-1,2-dimethyl-5-fluoro-4-nitrobenzimidazole

98% concentration nitric acid was added dropwise to 7.92 g of 7-chloro-1,2-dimethyl-5-fluorobenzimidazole in 139 ml of concentrated sulfuric acid above -5 ° C and below 0 ° C, during which the reaction proceeded to RP- Monitored by high performance liquid chromatography on 18 columns (HPLC; eluent: acetonitrile / water = 1: 1). As soon as the starting material was no longer detected, the reaction mixture was poured into ice water and the pH was adjusted to 14 with sodium hydroxide solution. The solid was separated, washed with water and dried at 20 ° C. in a vacuum drying oven. The two regioisomeric nitro compounds formed were separated by flash chromatography on silica gel (eluant: ethyl acetate; the first eluted product was the desired regioisomer). Yield: 5.6 g;

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 by tin dichloride / sodium borate in a similar manner as in step 2.5. The crude product obtained 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-fluorobenzimidazole was reacted with diphosgene in a similar manner as in step 5.4. The crude product was reacted directly without again separating to give the final product I.7.

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 were mixed in 100 ml of 1,2-dichloroethane, then the mixture was packed into a glass holder for a pressure vessel and heated at 120 ° C. for 5 hours in a sealed pressure vessel. During this process, the inherent pressure of the vessel rose to about 5 bar. The vessel was then cooled. The clear product solution was diluted with dilute aqueous potassium carbonate solution. The organic layer was dried over sodium sulfate and finally concentrated. The crude product was purified by flash chromatography using a short column (eluant: cyclohexane / tert-butyl methyl ether = 8: 2). Yield: 0.5 g;

Step 8.1

3- [4-chloro-6-fluoro-3-methoxy-2-nitrophenyl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione

The nitrated acid consisting of 20.4 ml of concentrated sulfuric acid and 25.5 ml of 98% strength nitric acid is cooled to -20 ° C and 51.0 g of 3- [4-chloro-6-fluoro-3-methoxy in 1 l of concentrated sulfuric acid. Phenyl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione was added dropwise slowly. After the addition was complete, stirring was continued at −20 ° C. for 30 minutes. The reaction mixture was then stirred into 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;

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 is added to 57.0 g of 3- [4-chloro-6-fluoro-3-methoxy-2-nitrophenyl] -1-methyl-6-trifluoro in about 500 ml of anhydrous dimethylformamide. To methyl-2,4- (1H, 3H) -pyrimidinedione. The mixture was then stirred at 80-90 ° C. for 3 hours. After cooling, 1 l of water was added to the reaction mixture. The valuable product was extracted with 3 x 200 ml of methyl tert-butyl ether. The ether layer was washed repeatedly with water, dried and finally concentrated. Yield: 46.1 g;

Step 8.3

3- [2-amino-4-chloro-6-fluoro-3-hydroxyphenyl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione

34 g of iron powder at 65 ° C. slightly at a time, 46.0 g of 3- [4-chloro-6-fluoro-3-hydroxy-2-nitrophenyl in 423 ml of water and 36.8 ml of concentrated hydrochloric acid ] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione. The mixture was then refluxed for 3 hours. After cooling, the mixture was shaken with 500 ml of ethyl acetate. Celite ; Manville Corporation) was used to remove residual inorganic material from the organic layer. The filtrate was dried over sodium sulfate and finally concentrated. Yield: 37.5 g;

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 dissolved in 30 g of anhydrous methanol in 0.5 g of 3- [2-amino-4-chloro-6-fluoro-3-hydroxyphenyl] -1-methyl-6-trifluoro To a solution of methyl-2,4- (1H, 3H) -pyrimidinedione (from step 8.3) was added. The mixture was then refluxed for 20 hours. Solvent and excess ortho ester were then removed under reduced pressure. The residue was taken up in ethyl acetate. The organic layer was washed with water and then dried over sodium sulfate and finally concentrated. The crude product was purified by flash chromatography (eluant: cyclohexane / tert-butyl ether = 3: 1). Yield: 0.26 g;

Example 10

3- [7-chloro-5-fluoro-2-methoxybenzoxazol-4-yl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H) -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 (From step 8.3) was reacted with tetramethyl orthocarbonate in a similar manner as in Example 9. Yield: 0.7 g;

In addition to the 3- (benzazol-4-yl) pyrimidinedione derivatives of formula (I) described above, other compounds prepared or that may be prepared in a similar manner are listed in Table 2 below:

Application example

The herbicide activity of 3- (benzazol-4-yl) pyrimidinedione derivative I was demonstrated by the following greenhouse experiment.

The culture vessel used is a plastic pot containing loam sand having about 3.0% humus soil as substrate. Seeds of the test plants were sown separately for each species.

In the case of pre-germination, the active ingredient suspended or emulsified in water was added directly after sowing through a fine spray nozzle. The container was gently watered to promote germination and then covered with a clear plastic hood until the plant took root. If this cover is not adversely affected by the active ingredient, this cover causes uniform germination of the test plant.

In the case of post-germination, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredient suspended or emulsified in water. Test plants for this purpose were either seeded directly or grown in the same container, or grown separately as seedlings and transplanted into the test container a few days before treatment. The rate of application in the post-emergence treatment was 15.6 or 7.8 g / ha as. (Active ingredient).

Depending on the species, the plants were placed at 10-25 ° C or 20-35 ° C. The test period lasted for 2-4 weeks. During this time the plants were groomed and the plants' response to each treatment was evaluated.

Evaluation was made in the range of 0-100. 100 means no plant bud or at least complete destruction of the aerobic part of the plant, and 0 means no damage or normal assumed process.

Plants used in greenhouse experiments belong to the following species.

Scientific name English name Amaranthus retroflexus Red Root Pigweed Cenopodium Alboom Spicy Liquor (Goursfoot) Gallium Afarin Catch with Bedro Soranum Nigrum Black nightshade Veronica Bell Speedwell Bell

Rate of application 15.6 and 7.8 g / ha a.s. Compound No. 18 in post-emergence had a very good herbicidal effect against the weeds described above.

Claims (9)

Novel 3- (benzazol-4-yl) pyrimidinedione derivatives of formula I and agriculturally useful salts of formula I. <Formula I> Where X is hydrogen or sulfur; R ¹ is hydrogen, amino, C ₁ -C ₆ alkyl or C ₁ -C ₆ -haloalkyl; R ² is hydrogen, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, or C ₁ -C ₆ alkylsulfonyl; R ³ is hydrogen, halogen or C ₁ -C ₆ alkyl; R ⁴ is hydrogen or halogen; R ⁵ is cyano, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy or C ₁ -C ₆ haloalkoxy; = Y- is a group = NN (R ⁶ )-, = C (ZR ⁷ ) -N (R ⁶ )-, = C (ZR ⁷ ) -O- or = C (ZR ⁷ ) -S-; R ⁶ is C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkylsulfonyl , (C ₁ -C ₆ alkyl) carbonyl, (C ₁ -C ₆ haloalkyl) carbonyl, (C ₁ -C ₆ alkyl) thiocarbonyl, (C ₁ -C ₆ alkoxy) carbonyl, (C ₁ -C ₆ alkoxy) thiocarbonyl, or cyano, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, (C ₁ -C ₆ alkoxy) carbonyl, (C ₁ -C ₆ alkylamino) carbonyl , a di (C ₁ -C ₆ alkyl) aminocarbonyl or (C ₁ -C ₆ alkyl) carbonyloxy C ₁ -C ₆ alkyl optionally substituted with, Z is a chemical bond, oxygen, sulfur, -S (O)-,-S (O) _2- , -NH- or -N (R ⁸ )-; R ⁷ and R ⁸ are independently C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, hydroxy-C ₁ -C ₄ alkyl, cyano-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkoxy-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenyloxy-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkynyloxy-C ₁ -C ₄ alkyl, C ₃ -C ₈ cycloalkoxy-C ₁ -C ₄ alkyl, Amino-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylamino-C ₁ -C ₄ alkyl, di (C ₁ -C ₄ alkyl) amino-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylthio- C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkylthio-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenylthio-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkynylthio-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylsulfinyl-C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkylsulfinyl-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenylsulfinyl-C _1- C ₄ alkyl, C ₃ -C ₄ alkynylsulfinyl-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkylsulfonyl-C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkylsulfonyl-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenylsulfonyl-C ₁ -C ₄ alkyl, C ₃ -C ₄ alkynylsulfonyl-C ₁ -C ₄ alkyl, C ₃ -C ₆ alkenyl, cyano-C ₃ -C ₆ alkenyl, C ₃ -C ₆ haloalkenyl, C ₃ -C ₆ alkynyl, cyano-C ₃ -C ₆ alkynyl, C ₃ -C ₆ haloalkynyl, hydroxycarbonyl-C ₁ -C ₄ alkyl, (C ₁ -C ₄ alkoxy) carbonyl-C ₁ -C ₄ alkyl, (C ₁ -C ₄ alkylthio) carbonyl-C ₁ -C ₄ alkyl, aminocarbonyl-C ₁ -C ₄ alkyl , (C ₁ -C ₄ alkyl, O No) carbonyl -C ₁ -C ₄ alkyl, di (C ₁ -C ₄ alkyl) amino carbonyl -C ₁ -C ₄ alkyl, di (C ₁ -C ₄ alkyl) -C ₁ -C ₄ alkyl sulfonyl Force , C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ cycloalkyl-C ₁ -C ₄ alkyl, phenyl, phenyl-C ₁ -C ₄ alkyl, 3- to 7-membered heterocyclyl or heterocyclyl-C ₁ -C ₄ alkyl (each heterocyclyl ring may comprise a carbonyl or thiocarbonyl ring member), Wherein each cycloalkyl, phenyl and heterocyclyl ring may be unsubstituted or attached with 1 to 4 substituents, where each substituent is cyano, nitro, amino, hydroxyl, carboxyl, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C _1- C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, (C ₁ -C ₄ alkoxy) carbonyl, (C ₁ -C ₄ alkyl) carbonyl, (C ₁ -C ₄ haloalkyl) carbonyl, (C ₁ -C ₄ alkyl) carbonyloxy, (C ₁ -C ₄ haloalkyl) carbonyloxy and di (C ₁ -C ₄ alkyl) amino, or Or, if Z is a chemical bond, then R ⁷ , if desired, is also hydrogen, hydroxy, cyano, mercapto, amino, halogen, -CH (OH) -CH ₂ -R ⁹ , -CH (halogen) -CH _2- R ⁹ , -CH ₂ -CH (halogen) -R ⁹ , -CH = CH-R ⁹ or -CH = C (halogen) -R ⁹ , wherein R ⁹ is hydroxycarbonyl, (C ₁ -C ₄ Alkoxy) carbonyl, (C ₁ -C ₄ alkylthio) carbonyl, aminocarbonyl, (C ₁ -C ₄ alkylamino) carbonyl or di (C ₁ -C ₄ alkyl) aminocarbonyl), Or R ⁷ and R ⁸ together are 1,3-propylene, tetra, unsubstituted or attached with 1 to 4 C ₁ -C ₄ alkyl groups or one or two (C ₁ -C ₄ alkoxy) carbonyl groups, respectively; Methylene, pentamethylene or ethyleneoxyethylene chains. The method of claim 1, X is hydrogen; R ¹ is hydrogen, amino or C ₁ -C ₆ alkyl; R ² is hydrogen, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, or C ₁ -C ₆ alkylsulfonyl; R ³ is hydrogen; R ⁴ is hydrogen, fluorine or chlorine; R ⁵ is cyano or halogen; R ⁶ is C ₁ -C ₆ alkyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkylsulfonyl or (C ₁ -C ₆ alkoxy) carbonyl, wherein the novel 3- (benzazole-4 -Yl) pyrimidinedione derivatives. 3. Use of the 3- (benzazol-4-yl) pyrimidinedione derivative I or its salt as agriculturally useful as a herbicide as claimed in claim 1. 3- (benzazol-4-yl) pyrimidinedione derivatives of formula I or salts thereof as claimed in claim 1 and at least one liquid and / or solid carrier and if necessary at least one surfactant Herbicide composition containing. Herbicidally active amounts of at least one 3- (benzazol-4-yl) pyrimidinedione derivative of formula (I) or salt thereof as claimed in claim 1, and at least one inert liquid and / or solid carrier and A method of making a pharmaceutically active composition comprising mixing one or more surfactants if necessary. At least one of the 3- (benzazol-4-yl) pyrimidinedione derivatives of formula (I) or salts thereof as claimed in claim 1 in a herbicidally active amount to act on plants, their environment or seeds Unnecessary plant control method, including that. Arylurea of Formula III. Wherein L ² is C ₁ -C ₄ -alkyl or phenyl and R ¹ -R ⁵ and Y are as defined in claim 1. Arylanilide of Formula IV. Wherein L ² is C ₁ -C ₄ -alkyl or phenyl and R ¹ -R ⁵ and Y are as defined in claim 1. Substituted 2-aminophenol, -thiophenol or -aniline of formula (V). Wherein the variables X and R ¹ -R ⁶ are as defined in claim 1.