SK7502000A3 - Herbicides 3-(benzazol-4-yl)pyrimidine-dione-derivatives - Google Patents

Abstract

The invention relates to 3-(benzazol-4-yl)pyrimidine-dione-derivatives of formula (I) and the salts thereof, whereby X = O, S; R<1> = H, NH2, C1-C6-alkyl, C1-C6-alkyl halide; R<2> = H, halogen, C1-C6-alkyl, C1-C6-alkyl halide, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl; R<3> = H, halogen, C1-C6-alkyl; R<4> = H, halogen; R<5> = CN, halogen, C1-C6-alkyl, C1-C6-alkyl halide, C1-C6-alkoxyl, C1-C6-alkoxyl halide; =Y- = a group =N-N(R<6>)-, =C(ZR<7>)-N(R<6>)-, =C(ZR<7>)-O-, =C(ZR<7>)-S-; R<6> = C1-C6-alkyl, C1-C4-alkyl halide, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkyl-SO2, C1-C6-alkyl-CO, C1-C6-alkyl halide-CO, C1-C6-alkyl-CS, C1-C6-alkoxyl-CO, C1-C6-alkoxyl-CS or optionally substituted C1-C6-alkyl; Z = chemical bond, O, S, -S(O)-, -SO2-, -NH-, -N(R<8>)-; R<7>, R<8> = C1-C6-alkyl, C1-C6-alkyl halide, hydroxy-C1-C4-alkyl, cyano-C1-C4-alkyl, C1-C4-alkoxyl-C1-C4-alkyl, C1-C4-alkoxyl halide-C1-C4-alkyl, C3-C4-alkenyloxyl-C1-C4-alkyl, C3-C4-alkynyloxyl-C1-C4-alkyl, C3-C8-cycloalkoxyl-C1-C4-alkyl, amino-C1-C4-alkyl, C1-C4-alkylamino-C1-C4-alkyl, di(C1-C4-alkyl)amino-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkylthio halide-C1-C4-alkyl, C3-C4-alkenylthio-C1-C4-alkyl, C3-C4-alkynylthio-C1-C4-alkyl, C1-C4-alkylsulfinyl-C1-C4-alkyl, C1-C4-alkylsulfinyl halide-C1-C4-alkyl, C3-C4-alkenylsulfinyl-C1-C4-alkyl, C3-C4-alkynylsulfinyl-C1-C4-alkyl, C3-C6-alkenyl, cyano-C3-C6-alkenyl, C3-C6-alkenyl halide, C3-C6-alkynyl, cyano-C3-C6-alkynyl, C3-C6-alkynyl halide, HO-CO-C1-C4-alkyl, (C1-C4-alkoxyl)CO-C1-C4-alkyl, (C1-C4-alkyl)CS-C1-C4-alkyl, H2N-CO-C1-C4-alkyl, C1-C4-alkyl-NHCO-C1-C4-alkyl, di(C1-C4-alkyl)NCO-C1-C4-alkyl, di(C1-C4-alkyl)phosphonyl-C1-C4-alkyl, optionally substituted C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkyl, 3- to 7-linked heterocyclyl or heterocyclyl-C1-C4-alkyl, whereby each heterocyclyl ring can contain a CO-ring link or CS-ring link, or provided that Z = chemical bond, R<7> also H, OH, CN, SH, NH2, halogen, -CH(OH)-CH2-R<9>, -CH(halogen)-CH2-R<9>, -CH2-CH(halogen)-R<9>, -CH=CH-R<9> or -CH=C(halogen)-R<9>, whereby R<9> = COOH, (C1-C4-alkoxyl)carbonyl, (C1-C4-alkylthio)carbonyl, CONH2, C1-C4-alkyl-NHCO or di(C1-C4-alkyl)NCO, or R<7> + R<8> = an optionally substituted 1,3-propylene-, tetramethylene-, pentamethylene- or ethylene oxyethylene-chain.

Description

Herbicidal derivatives of 3- (benzazol-4-yl) pyrimidinedione

Technical field

The present invention relates to novel 3- (benzazol-4-yl) pyrimidinedione derivatives

where the variables have the following meaning:

X is oxygen or sulfur;

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

R ² is hydrogen, halo, _Ci-C6 alkyl, _Ci-C6 haloalkyl, _Ci-C6 alkylthio, _Cl-C6 alkylsulfinyl or C6-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 = NN (R ⁶ ) -, = C (ZR ⁷ ) -N (R ⁶ ) -, = C (ZR ⁷ ) -O- or = C (ZR ⁷ ) -S-;

R ⁶ is a C, -C6-alkyl, Ci-C ₄ haloalkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -alkenyl, C ₃ -C ₆ -alkynyl, C _r C ₆ alkylsulfonyl, (C C ₆ -alkyl) carbonyl, (C 1 -C ₆ -haloalkylcarbonyl, (C 1 -C ₆ alkyl) thiocarbonyl, (C 1 -C ₆ -alkoxy) carbonyl, (C 1 -C ₆ -alkoxy) thiocarbonyl or C 1 -C ₆ -alkyl which may be substituted by cyano, C 1 -C 6 -alkoxy , C ₁ -C ₆ alkylthio, (C 1 -C ₆ -alkoxy) carbonyl, (C 1 -C ₆ -alkylamino) carbonyl, di (C 1 -C ₆ -alkyl) aminocarbonyl or (C ₁ -C ₆ -alkyl) carbonyloxy;

Z is a chemical bond, oxygen, sulfur, -S (O) -, -S (O) ₂ -NH- or -N (R ⁸ ) -;

R ⁷ and R ⁸ are independently of each other

A C -C alkyl, C -C haloalkyl, hydroxy-Ci-C4-alkyl, cyano-C4-alkyl, _{C1-C4alkoxy-Ci-C4-alkyl, C4-haloalkoxy-Ci-C4-alkyl,} C3- 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 -alkyl 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 -alkenyltioCi -C ₄ -alkyl, C ₃ -C ₄ -alkynyltio--C ₄ -alkyl, C ₄ alkylsulfinyl-C 4 alkyl, C _r C ₄ haloalkylsulfinyl-C 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 ₁ C 1 -C 4 -haloalkylsulfonyl- Cr _C4-alkyl, C ₃ -C 4 -alkenylsulfonyl-C ₄ -alkyl, C ₃ -C 4 -alkynylsulfonyl-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) carbonylC 1 -C ₄ alkyl, _{(Cl-C4-alkylthio)} carbonyl-C, -C4-alkyl, aminocarbonyl _{carbonyl-Ci-C4-alkyl,} (C _r C4-alkylamino) _{-carbonyl-Ci-C4-alkyl,} di (C, -C4-alkyl) aminocarbonyl-Ci-C4-alkyl, di _(Ci-C4 alkyl) phosphonyl-C4-alkyl,

C ₃ -CE-cycloalkyl, _{C3 -Ca-cycloalkyl-Ci-C4-alkyl,} phenyl, _{phenyl-Ci-C4-alkyl,} 3- to 7 or _{heterocyclyl-Ci-C4-alkyl,} wherein each heterocyclyl the ring may contain carbonyl or thiocarbonyl within the ring, and it is possible that each cycloalkyl, phenyl and heterocyclyl may be unsubstituted or carry one to four substituents in each case selected from the group consisting of: cyano, nitro, amino, hydroxyl, carboxyl, halogen, C4-alkyl, _Ci-C4 haloalkyl, _Ci-C4 alkoxy, C1 -C4 -haloalkoxy, C ₄ alkylthio, _Ci-C4 -haloalkyltio, C ₁ -C ₄ -alkylsulfonyl, C ₄ -haloalkylsulfonyl , _(C-C4 alkoxy) carbonyl, _(Ci-C4 alkyl) carbonyl, _(Ci-C4 haloalkyl) carbonyl, (Ci-C ₄ -alkyl) carbonyloxy, _(Ci-C4 haloalkyl) carbonyloxy and di (C 1 -C ₄ alkyl) amino, or when Z is a chemical bond, R ⁷ can also be hydrogen, hydroxyl, 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 ^{7 8} are together 1,3-propylene, tetramethylene, pentamethylene or ethyleneoxyethylene, which may in each case be unsubstituted or carry one to four C 1 -C 4 -alkyls or one or two (C 1 -C 4 -alkoxy) carbonyls;

and agriculturally useful salts of compounds I.

The invention further relates to

- use of compounds I as herbicides,

- herbicidal compositions containing compounds I as active substances,

- processes for preparing compounds I and herbicidal compositions using compounds I,

methods for controlling undesirable vegetation using compounds I and

- intermediates of formulas III, IV and V for the preparation of compounds I.

BACKGROUND OF THE INVENTION

WO 97/08170 discloses certain 3- (benzox / benzothiazol-7-yl) -6- (trifluoromethyl) uracils as herbicides. Other 3- (benzothiazol-7-yl) uracils and their use as herbicides and for desiccating or defoliating plants are described in WO 97/08171. WO 97/12886 discloses, inter alia, certain 3-benzisoxazol-7-yl-2,4- (1H, 3H) pyrimidinediones, which are said to have herbicidal and desiccant activity.

SUMMARY OF THE INVENTION

It is an object of the present invention to provide novel herbicidally active uracil compounds which allow for better targeted control of unwanted plants than that which was possible using known compounds.

We have found that this object is achieved by the present 3- (benzazol-4-yl) pyrimidinedione derivatives of formula I.

In addition, herbicidal compositions have been found which contain compounds I and which have very good herbicidal activity. In addition, processes have been found for preparing these compositions and methods for controlling undesirable vegetation using compounds I.

Depending on the substitution, the compounds of formula I may contain one or more chiral centers, where they exist in the form of enantiomers or diastereomeric mixtures. In the case of compounds I having at least one olefinic radical, E / Z isomers may also be possible. The present invention relates to pure enantiomers or diastereomers as well as mixtures thereof.

Formula I represents only one of the possible versions for some of the compounds of the invention. Thus, for example, compounds I where R ⁷ = hydroxyl can also be registered as tautomers 1 '[-N = C (OH) - <--> -NH-CO-j:

Suitable among the agriculturally useful salts are, in particular, the salts of those cations or acid addition salts of those acids whose cations or anions do not adversely affect the herbicidal activity of the compounds I. Thus, suitable cations are in particular alkali metal ions, preferably sodium and potassium, alkaline earth metal ions. preferably calcium, magnesium and barium, and transition metals, preferably manganese, copper, zinc and iron, as well as an ammonium ion which may carry one to four C 1 -C 4 alkyl substituents and / or phenyl or benzyl, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium , trimethylbenzylammonium, phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 -alkyl) sulfonium, and sulfoxonium ions, preferably tri (C 1 -C 4 -alkyl) sulfoxonium.

Anions of useful acid addition salts are in particular chloride, bromide, fluoride, hydrogen sulphate, sulphate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and C 1 -C 4 alkanoic acid anions, preferably format and acetate, propionate . They may be formed by reaction of I with an acid of the corresponding anion, preferably hydrochloric, hydrobromic, sulfuric, phosphoric or nitric acid.

Organic moieties - similar to those of halogen - which are mentioned in the definition of substituents R ¹ to R ³ and R ⁵ to R ⁹ or as radicals of cycloalkyl, phenyl or heterocyclic rings represent collective terms for the individual calculations of the individual group members. All carbon chains, i.e., each alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, aminoalkyl, hydroxycarbonylalkyl, aminocarbonylalkyl, phenylalkyl, heterocyclylalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkenyl, alkio, haloalkylsulfonyl, alkenyl, alkenyl, alkenyl, alkenyl, alkenyl, alkenyl, alkenyl, alkenylsulfinyl, alkenylsulfonyl, alkynyl, haloalkynyl, cyanoalkynyl, alkynyloxy, alkynylthio, alkynylsulfinyl and alkynylsulfonyl may be linear or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms. The meaning of halogen in each case is fluorine, chlorine, bromine or iodine.

Other meanings are:

- 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 ;

- Ci-C ₄ -haloalkyl: a C-C ₄ -alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, e.g. CH ₂ F, CHF ₂ , CF ₃ CH ₂ Cl, CH (CI) ₂ C (Cl) ₃ , chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromomethyl, 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, C2F5, 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, _CH2 -C2F _5, CF2-C2F5, l- (fluoromethyl) -

2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromomethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;

- C -C alkyl; C -C ₄ -alkyl radical as mentioned above or, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2dimethylbutyl, 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 nhexyl;

C 1 -C ₆ -haloalkyl: The C 1 -C ₆ -alkyl radical as mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, ie one or more of the radicals mentioned under C ₁ -C ₄ -haloalkyl or 5 -fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6-fluoro-1-hexyl 6-chloro-1-hexyl, 6-bromo-1-hexyl, 6-iodo-1-hexyl, 6,6,6-trichloro-1-hexyl or dodecafluorohexyl;

cyano-C 1 -C 4 alkyl: CH 2 CN, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl, 1-cyanobut-1-yl, 2-cyanobut-1- yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl, 3-cyanobut-2-yl, 4-cyanobut-

2-yl, 1- (CH ₂ CN) et-1-yl, 1- (CH ₂ CN) -1- (CH ₃ ) -et-1-yl or 1- (CH ₂ CN) prop-1-yl ;

hydroxy-C 1 -C ₄ -alkyl: CH ₂ OH, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxyprop-1-yl, 2-hydroxyprop-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) et-1-yl, 1- (CH ₂ OH) -1- (CH ₃ ) -et-1-yl or 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-aminobutyl- 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-amino-but-2-yl,

1- _{(CH2 NH2)} eth-1-yl, 1- _{(CH2 NH2)} -1- _(CH3) eth-1-yl or 1- _{(CH2 NH2)} prop-1-yl;

hydroxycarbonyl-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) et-1-yl, 1 (CH ₂ COOH) -1- (CH ₃ ) -et-1-yl or 1- (CH ₂ COOH) prop-1-yl;

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- _(CONH2) prop-1-yl, 1- _(CONH2) 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 ) et-1-yl, 1 (CH ₂ CONH ₂ ) -1- (CH ₃ ) -et-1-yl or 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-yl, 1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut- 2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, 1- (benzyl) et-1-yl, 1- (benzyl) -1- (methyl) et-1-yl or 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-yl,

1-heterocyclylbut-2-yl, 2-heterocyclylbut-2-yl, 3-heterocyclylbut-2-yl, 3-heterocyclylbut-2-yl, 4-heterocyclylbut-2-yl, 1- (heterocyclylmethyl) et-1-yl , 1- (heterocyclylmethyl) -1- (methyl) et-1-yl or 1- (heterocyclylmethyl) prop-1-yl, preferably heterocyclylmethyl or 2-heterocyclylethyl;

C 1 -C ₄ -alkoxy: OCH ₃₁ OC ₂ H ₅ , OCH ₂ -C ₂ H ₅ , OCH (CH ₃ ) ₂₁ n -butoxy, OCH (CH ₃ ) -C ₂ H ₅ , OCH ₂ -CH (CH _{3 12} or C (CH ₃ ) ₃ ; preferably OCH ₃ , OC ₂ H ₅ or OCH (CH ₃ ) ₂ ;

C ₁ -C ₄ -haloalkoxy: The C ₁ -C ₄ -alkoxy radical as mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, e.g. OCH ₂ F, OCHF ₂ , OCF ₃ , OCH ₂ Cl, OCH (CI) 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 1- (CH ₂ Br) -2-bromoethoxy, 4 -fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, preferably OCHF ₂ , OCF ₃ , dichlorofluoromethoxy, chlorodifluoromethoxy or 2,2,2-trifluoroethoxy;

C 1 -C 6 -alkoxy: C ₁ -C ₄ -alkoxy radical as mentioned above or, for example, npentoxy, 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 or n-hexoxy;

C 1 -C 6 -haloalkoxy: C 1 -C 6 -alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, ie one of the radicals mentioned under C 1 -C ₄ -haloalkoxy or 5-fluoro 1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5,5,5-trichloro-1-pentoxy, undecafluoropentoxy, 6-fluoro-1-hexoxy, 6 -chloro-1-hexoxy, 6-bromo-1-hexoxy, 6-iodo-

1-hexoxy, 6,6,6-trichloro-1-hexoxy or dodecafluorohexoxy;

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 ₅₁ SCH ₂ -CH (CH ₃ ) ₂ or SC ( CH ₃ ) ₃ , preferably SCH ₃ or SC ₂ H ₅ ;

C 1 -C ₄ -haloalkylthio: The C 1 -C ₄ -alkylthio radical as mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, e.g. SCH ₂ F, SCHF ₂ , SCF ₃ , SCH ₂ CI, SCH (CI) 2, SC (CI) ₃ , chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromomethylthio, 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 -fluórpropyltio.

3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3, 3-trichloropropylthio, SCH2-C2F5, SCF2-C2F5, 1- _(CH2 F) -2-fluoroethylthio, 1 (CH ₂ Cl) -2-chloroethylthio, 1- _(CH2 Br) -2-bromoethylthio, 4-fluorobutylthio 4-chlorobutylthio, 4-bromobutylthio or SCF2-CF2-C2F5, preferably SCHF ₂ , SCF ₃ , dichlorofluoromethylthio, chlorodifluoromethylthio or 2,2,2-trifluoroethylthio;

C 1 -C ₆ -alkylthio: C 1 -C ₄ -alkylthio radical as mentioned above or, for example, n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropythio, n-hexylthio, 1, 1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio,

2-methylpentylthio, 3-methylpentylthio, 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, SC (CH ₃ ) ₃ , n-pentylthio or n-hexylthio;

C 1 -C ₄ -alkoxy-C 1 -C 4 -alkyl: C 1 -C 4 -alkyl which is substituted by C 1 -C 4 -alkoxy as mentioned above, e.g. CH 2 CH 2 OCH _{3 R-OC2H5,} n-propoxymethyl, CH ₂ OCH (CH _{3) 2,} n-butoxymethyl, (l-methyl-propoxy) methyl, (2-methyl-propoxy) 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- (methoxy) propyl, 2- (ethoxy) propyl, 2- (n-propoxy) propyl, 2- (1-methylethoxy) propyl, 2 - (n-butoxy) propyl, 2- (1-methylpropoxy) propyl, 2- (2-methylpropoxy) propyl, 2- (1,1-dimethylethoxy) propyl, 3- (methoxy) propyl, 3- (ethoxy) - propyl, 3- (n-propoxy) propyl, 3- (1-methylethoxy) propyl, 3- (n-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-methyl-propoxy) butyl or 4 (1,1-dimethylethoxy) butyl, preferably CH ₂ OCH _3, CH 2-OC2H5, 2- _(OCH3) ethyl or 2 (OC ₂ H ₅₎ ethyl;

C ₁ -C ₄ -haloalkoxy-C ₁ -C ₄ -alkyl: C ₁ -C ₄ -alkyl ₁ which is substituted with C ₁ -C ₄ haloalkoxy as mentioned above, e.g. 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: C 1 -C ₄ -alkyl, which is substituted by a C 1 -C 4 -alkylthio group as mentioned above, e.g. CH ₂ -SCH ₃ , CH 2 -SC ₂ H 5, n-propylthiomethyl, CH ₂ -SCH (CH ₃ ) ₂ , n-butylthiomethyl, (1-methylpropylthio) methyl, (2-methylpropylthio) 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- (methylthio) propyl, 2- (ethylthio) propyl, 2- (n-propylthio) propyl, 2 (1-methylethylthio) propyl, 2- (n-butylthio) propyl, 2- (1-methylpropylthio) propyl, 2- (2-methylpropylthio) propyl, 2- (1,1-dimethylethylthio) propyl, 3- (methylthio) propyl, 3- ( ethylthio) propyl, 3 (n-propylthio) propyl, 3- (1-methylethylthio) propyl, 3- (n-butylthio) propyl, 3- (1-methylpropylthio) propyl, 3- (2-methylpropylthio) propyl, 3- (1,1-dimethylethylthio) propyl, 2- (methylthio) butyl, 2- (ethylthio) butyl, 2- (n-propylthio) butyl, 2- (1-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 -metylpropyltio) butyl or 4- (1,1 -dimetyletyltio) butyl, preferably CH2-SCH3, CH2-SC2H5, 2- _(SCH3) ethyl or 2- (SC2H5) ethyl;

C 1 -C 4 -haloalkylthio-C 1 -C 4 -alkyl: C 1 -C ₄ -alkyl, which is substituted by a C 1 -C 4 haloalkylthio group as mentioned above, e.g. 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-butylcarbonyl, 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 radical as mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, e.g. CO-CH ₂ F, CO-CHF ₂ , CO-CF ₃ , CO-CH ₂ Cl, CO-CH (Cl) ₂ , CO-C (Cl) ₃ , chlorofluoromethylcarbonyl, dichlorofluoromethylcarbonyl, chlorodifluoromethylcarbonyl, 2fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromomethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-

2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, CO-C2F5, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-difluoropropylcarbonyl,

2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl, 3,3,3-trichloropropylcarbonyl, CO-CH2-C2F5, CO- CF2-C2F5, 1 (CH ₂ F) -2-fluoroethylcarbonyl, 1 - (CH ₂ Cl) -2-chloroethylcarbonyl, 1 - (CH ₂ Br) -2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or nonafluorobutylcarbonyl, preferably CO-CF ₃ , CO-CH ₂ Cl or 2,2,2-trifluoroethylcarbonyl;

(C ₁ -C ₆ -alkyl) carbonyl: one of the above (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, 1,211 dimethylpropyl-CO, 1-methylpentyl-CO, 2-methylpentyl-CO, 3-methylpentyl-CO 4-methylpentyl-CO, 1,1-dimethylbutyl-CO, 1,2-dimethylbutyl-CO, 1,3-dimethylbutyl-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 or 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 Hn) or CO- (nC ₆ H ₃ );

(C 1 -C ₆ -haloalkyl) carbonyl: (C 1 -C 6 -alkyl) carbonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, e.g. CO-CH ₂ F, CO-CHF ₂ , CO-CF ₃ , CO-CH ₂ Cl, CO-CH (Cl) ₂ , COC (Cl) ₃ , chlorofluoromethylcarbonyl, dichlorofluoromethylcarbonyl, chlorodifluoromethylcarbonyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromomethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbonyl, 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-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromobropylcarbonyl , 3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl, 3,3,3-trichloropropylcarbonyl, CO-CH ₂ -C ₂ F ₅ , CO-CF ₂ -C ₂ F ₅ , 1- (CH ₂ F) -2- fluoroethylcarbonyl, 1- (CH ₂ Cl) -2-chloroethylcarbonyl, 1 (CH ₂ Br) -2-bromomethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or nonafluorobutylcarbonyl, preferably CO-CF ₃ , CO-CH ₂ Whether 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-COCH (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 radical as mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, e.g. O-CO-CH ₂ F, O-CO-CHF ₂ , O-CO-CF ₃ , O-CO-CH ₂ Cl, O-COCH (CI) ₂ , O-CO-C (Cl) ₃ , chlorofluoromethylcarbonyloxy, dichlorofluoromethylcarbonyloxy, chlorodifluoromethylcarbonyloxy, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy, 2-bromomethylcarbonyloxy, 2-iodoethylcarbonyloxy, 2,2-difluoroethylcarbonyloxy, 2,2,2-trifluoromethylcarbonyloxy, 2-chloroethyl 2-chloro 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-chloropropylcarbonyloxy, 3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbonyloxy, 2-bromopropylcarbonyloxy, 3-bromopropylcarbonyloxy, 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-chloroethylcarbonyloxy, 1- (CH2Br) -2-bromomethylcarbonyloxy, 4-fluorobutylcarbonyloxy, 4-chlorobutylcarbonyloxy, 4-bromobutylcarbonyloxy or nonafluorobutylcarbonyloxy, preferably O-CO-CF3, O-CO-CH2Cl or 2,2,2- trifluóretylkarbonyloxy;

(C 1 -C ₆ -alkyl) carbonyloxy: one of the above (C 1 -C ₄ -alkyl) carbonyloxy radicals, or, for example, n-pentyl-COO, 1-methylbutyl-COO, 2-methylbutyl-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-methylpentylCOO, 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, with preferably O-CO-CH3, O-CO-C ₂ H _5, O-CO-CH2-C2H5, O-COCH (CH ₃₎ 2, n-butyl-CO-O, O-CO-C _{(CH3) 3,} O-CO- (nC ₆ H 3) or O-CO- (n C ₆ H ₃ );

(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-in-CsHn), CSCH (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 C2 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 ₃ ), CS-CH (CH ₃ ) - (n C 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-CH2 CH (C 2 H ₅₎ C ₂ H _5, CS-C _(CH3) 2-CH _{(CH3) 2,} CS-CH _(CH3) - 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 ₂ -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 above (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-methylpentoxyCO, 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- WHAT,

3,3-dimethylbutoxy-CO, 1-ethylbutoxy-CO, 2-ethylbutoxy-CO, 1,1,2-trimethylpropoxyCO, 1,2,2-trimethylpropoxy-CO, 1-ethyl-1-methylpropoxy-CO or 1- ethyl-2-methylpropoxy-CO, preferably CO-OCH 3, CO-OC ₂ H ₅ , CO-OCH ₂ -C ₂ H ₅₁ CO-OCH (CH ₃ ) ₂ , n-butoxy-CO, CO-OC (CH 3 13, n-pentoxy-CO or n-hexoxy-CO;

(C 1 -C ₄ -alkoxy) carbonyl-C 1 -C ₄ -alkyl: C 1 -C ₄ -alkyl which is substituted with (C 1 -C ₄ alkoxy) carbonyl as mentioned above, e.g. CH ₂ -CO-OCH ₃₁ CH ₂ -CO-OC ₂ H ₅ , CH ₂ -CO-OCH ₂ -C ₂ H ₅ , CH ₂ -CO-OCH (CH ₃ ) ₂₁ n-butoxycarbonylmethyl, CH ₂ -COOCH ( 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- [CO-OCH _(CH3) 2] ethyl,

2- (n-butoxycarbonyl) ethyl, 2- [1 -metylpropoxykarbonyljetyl, 2- [2-metylpropoxykarbonyljetyl, 2- [CO-OC _(CH3) 3] ethyl, 2- _(CO-OCH3) propyl, 2- ( CO-OC ₂ H ₅ ) propyl, 2 (CO-OCH 2 -C ₂ H ₅ ) propyl, 2- [CO-OCH (CH 3) 2] propyl, 2- (n-butoxycarbonyl) propyl, 2 [1-methylpropoxycarbonyl] propyl, 2- [2-methylpropoxycarbonyl] propyl, 2- [COOC (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- [CO-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- [COOCH (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- (COOC ₂ H ₅ ) butyl, 3- (CO-OCH ₂ -C ₂ H ₅ ) butyl, 3- [CO-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- [CO-OCH (CH ₃ ) ₂ ] butyl, 4- (n-butoxycarbonyl) butyl, 4- [1-methylpropoxycarbonyl] butyl, 4- [2-methylpropoxycarbonyl] butyl or 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 or 1- (COOC 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, CSOCH (CH ₃ ) ₂ , CS-O (nC ₄ H ₉ ), CS- OCH (CH ₃ ) -C ₂ H ₅ , CS-OCH ₂ -CH (CH ₃ ) ₂₁ CSOC (CH ₃ ) _3i 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 Hi ₃ ), 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 ) ₂₁ CS-OC (CH ₃ ) ₂ -CH ₂ -C ₂ H _5i CS-OCH (CH ₃ ) -CH (CH ₃ ) -C ₂ H _5i csOCH ( 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 ) _2i 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 ) _2i 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 ) ₂₁ CO-SCH ₂ CH ₂ -C ₂ H ₅₁ CO-SCH (CH ₃ ) -C ₂ H _5; CO-SCH ₂ -CH (CH ₃ ) ₂ or COSC (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 -alkyl, which is substituted with (C 1 -C 4 alkylthio) carbonyl as mentioned above, e.g. _{CH2-CO-SCH3, CH2-CO-SC 2} H _5, CH ₂ SCH ₂ CO-C ₂ H _5, CH ₂ CO-SCH _{(CH3) CH2 21} -CO-SCH ₂ CH ₂ -C ₂ H ₅ , CH ₂ -COSCH (CH ₃ ) -C ₂ H _5i 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- (COSCH 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) 12} ] ethyl, 2- [CO-SC (CH ₃ ) ₃ ] ethyl, 2- (CO-SCH ₃ ) propyl, 2- (COSC ₂ H ₅ ) propyl, 2- (CO-SCH ₂ -C ₂ H) ₅ ) propyl, 2- [CO-SCH (CH ₃ ) ₂ ] propyl, 2- (COSCH 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- (COSCH 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- [COSCH (CH ₃ ) ₂ ] butyl, 2- (CO-SCH ₂ CH ₂ -) C ₂ H 5) butyl, 2- [C O-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- (COSC 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- [COSC (CH ₃ ) ₃ ] butyl, 4- (CO-SCH ₂ ) butyl, 4- (CO-SC ₂ H ₅ ) butyl, 4- (CO-SCH ₂ -C ₂ H ₅ ) butyl,

4- [CO-SCH _{(CH3) 2]} butyl, 4- (CO-SCH2CH2-C 2 H ₅₎ butyl, 4- [CO-SCH (CH 3) -C ₂ H _5] butyl, 4- _[CO-SCH2 -CH (CH 3) ₂ ] butyl or 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 or 1 - (CO-SC ₂ H ₅ ) ethyl;

_Cl-C6 alkylsulfinyl: _Ci-C4 alkylsulfinyl radicals such as _SO-CH3, SO-C ₂ H _{5 R} SO-CH2-C2H5, SO-CH _(CH3) 2, SO- (n-C ₄ H ₉₎ SO-CH (CH ₃ ) -C ₂ H ₅ , SO-CH ₂ -CH (CH ₃ ) ₂ or SO-C (CH ₃ ) ₃₁ or, for example, SO- (nC ₅ Hn), 1-methylbutyl-SO, 2-methylbutylSO, 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-dimethylbutyl-SO,

1-ethylbutyl-SO, 2-ethylbutyl-SO, 1,1,2-trimethylpropyl-SO, 1,2,2-trimethylpropyl-SO, 1-ethyl-1-methylpropyl-SO or 1-ethyl-2-methylpropyl-SO, preferably SO-CH3, SOC ₂ H _5, SO-CH2-C2H5, SO-CH _{(CH3) 2,} SO- (n-C ₄ H _9), SOC _{(CH3) 3,} -SO- (n-C ₅ H N ) and SO (n C6Hi _3);

C 1 -C ₄ -alkylsulfinyl-C 1 -C ₄ -alkyl: C 1 -C ₄ -alkyl which is substituted with C 1 -C ₄ -alkylsulfinyl as mentioned above, e.g. 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 _{4 -haloalkylsulfinyl-C-C4-alkyl: Ci-C4-alkyl} which is substituted by C _r C ₄ haloalkylsulfinyl as mentioned above, e.g. 2- (2,2,2-trifluoroethylsulfinyl) ethyl;

_{Ci-C4-alkylsulfonyl:} SO2-CH3, SO2-C2H5, SO2-CH2-C2H5, SO2-CH (CH3) 2, nbutylsulfonyl, 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 or SO ₂ -C ₂ H ₅ ;

C 1 -C ₄ -haloalkylsulfonyl: a C 1 -C ₄ -alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, e.g. SO ₂ -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, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromomethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloroethylsulfonyl, 2,2-dichloroethylsulfonyl fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, SO ₂ C ₂ F ₅ , 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 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-chloroethylsulfonyl, 1 - (bromomethyl) -2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl, preferably SO ₂ -CH ₂ Cl, SO ₂ - CF 3 or 2,2,2-trifluoroethylsulfonyl;

C 1 -C ₆ -alkylsulfonyl: C ₁ -C ₄ -alkylsulfonyl radical as mentioned above or, for example, SO ₂ - (n-C 5 H 11), 1-methylbutyl-SO ₂ , 2-methylbutyl-SO ₂ , 3-methylbutyl-SO ₂ ,

2,2-dimethylpropyl-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- _SO2, 3-methylpentyl-SO _2, 4-methylpentyl-SO _2, 1,1-dimetylbutylSO _2, 1,2-dimetylbutylSO _2, 1,3-dimetylbutylSO _2, 2,2-dimetylbutylSO _2, 2 , 3-dimethylbutyl-SO _2, 3,3-dimethylbutyl-SO _2, 1 _{etylbutylSO-2,} 2-etylbutylSO _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 - (n C ₅ H 11) or SO ₂ - (n-C ₆ H 13);

C 1 -C ₄ -alkylsulfonyl-C 1 -C ₄ -alkyl: C 1 -C ₄ -alkyl which is substituted with C 1 -C ₄ alkylsulfonyl as mentioned above, e.g. CH ₂ SO ₂ -CH 3, CH ₂ SO ₂ -C ₂ H ₅ ,

CH2 SO ₂ C 2 H _{5 R-CH2 CH2 SO2} CH _{(CH3) 2,} CH ₂ SO ₂ CH ₂ CH ₂ -C ₂ H _5, (1-methylpropylsulfonyl) methyl, (2-methylpropylsulfonyl) methyl, _CH2 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 _5i CH ₂ CH ₂ SO ₂ -CH ₂ -C ₂ H ₅ , CH ₂ CH ₂ SO ₂ -CH (CH ₃ ) _2i 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- _[SO2 --CH (CH3) _2] propyl, 3- _{(SO2 --CH2} CH2-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 or 4- [SO ₂ -C (CH 3) 3] butyl, especially CH ₂ CH ₂ SO ₂ CH ₃ or 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 which is substituted with C 1 -C 4 haloalkylsulfonyl as mentioned above, e.g. 2- (2,2,2-trifluoroethylsulfonyl) ethyl;

C 1 -C 4 -alkylamino-C 1 -C 4 -alkyl: C 1 -C 4 -alkyl, which is substituted by C 1 -C 4 -alkylamino, for example H ₃ C-NH-, H ₅ C ₂ -NH-, n-propyl-ΝΗ-, 1-methylethyl- NH-, n-butyl ΝΗ-, 1-methylpropyl-NH--, 2-methylpropyl-NH-- and 1,1-dimethylethyl-NH--, preferably H3 C-NH or C ₂ H ₅ NH, i.e. for example _CH2 CH ₂ -NH-CH _3, CH ₂ CH ₂ N (CH _{3) 2,} CH ₂ CH 2 -NH-C ₂ H ₅ or CH ₂ CH 2 N (C ₂ H 5) 2;

(C 1 -C 4 -alkylamino) carbonyl: CO-NH-CH 3, CO-NH-C ₂ H ₅ , n-propylamino, CO-NHCH (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 or CO-NH-C (CH ₃ ) ₃ , preferably CO-NH-CH 3 or CO-NH-C ₂ H ₅ ;

(C 1 -C ₆ -alkylamino) carbonyl: one of the (C 1 -C ₄ -alkylamino) carbonyl radicals mentioned above, or, for example, CO-NH- (nC ₅ Hn), 1-methylbutyl-NHCO-,

2-methylbutyl-NHCO-, 3-methylbutyl-NHCO-, 2,2-dimethylpropyl-NHCO-, 1-ethylpropylNHCO-, CO-NH- (nC ₆ Hi3), 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- or 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-NHCH (CH ₃ ) ₂ , CO-NH- (nC ₄ H ₉ ), CO-NH-C (CH ₃ ) ₃ , CO-NH- (nC ₅₎ Hn) or CO-NH- (nCeHn);

- (Ci -C ₄ -alkylamino) _{carbonyl-Ci-C4-alkyl: Ci-C4-alkyl} which is substituted by (C _r C ₄ alkylamino) carbonyl as mentioned above, preferably by _CO-NH-CH3 or CO NH-C ₂ H _{5 R} e.g. 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 ) _2i 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 ) _2i CH ₂ -CO-NH-C (CH ₃ ) ₃ , CH (CH ₃ ) -CO-NH-CH _3i CH (CH ₃ ) -CO-NH-C ₂ H _5i 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-NHCH (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- (CONH-CH ₃ ) propyl, 2- (CO-NH-C ₂ H ₅ ) propyl, 2- (CO -NH-CH ₂ -C ₂ H ₅ ) propyl, 2- [CH ₂ -CONH-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 _and 2- [CO-NH-C (CH ₃ )] ₃ ] propyl, 3- (CO-NHCH ₃ ) propyl, 3- (CO-NH-C ₂ H ₅ ) propyl, 3- (CO-NH-CH ₂ -C ₂ H ₅ ) propyl, 3- [CH ₂ -CO-NHCH (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-NHCH ₃ ) butyl, 2- (CO-NH-C ₂ H ₅ ) butyl, 2- (CO-NH-CH ₂ - C ₂ H ₅ ) butyl, 2- [CH ₂ -CO-NHCH (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-NHC 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-NHCH 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 ] 19 butyl or 4- [ CO-NH-C (CH ₃ ) 3] butyl, preferably CH ₂ -CO-NH-CH ₃ , CH ₂ -CO-NHC ₂ H ₅₁ 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 , Ν, Ν-dipropylamino, N, N-di (1-methylethyl) amino, Ν, Ν-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-dimethylethyl) amino, N- (1- methylpropyl) -N- (2-methylpropyl pyl) 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) amino-C 1 -C ₄ -alkyl: C 1 -C ₄ -alkyl, which is substituted with di (C ₁ -C ₄ -alkyl) amino as mentioned above, e.g. CH ₂ N (CH ₃ ) ₂ , CH ₂ N (C ₂ H ₅ ) ₂ , Ν, Ν-dipropylaminomethyl, N, N-di [CH (CH ₃ ) ₂ ] aminomethyl, N, N-dibutylaminomethyl, N, Nd i- (1-lpropyl) aminomethyl, N, N-di (2-methylpropyl) aminomethyl, N, N-di [C _{(CH3) 3]} aminomethyl, N-ethyl-N-methylaminomethyl, N-methyl-N propylaminomethyl, N-methyl-N- [CH _{(CH3) 2]} aminomethyl, N-butyl-N-methylaminomethyl, N-methyl-N- (1-methylpropyl) aminomethyl, N-methyl-N- (2-methylpropyl) aminomethyl N- [C _{(CH3) 3]} -N-methyl-N-ethyl-N-propylaminomethyl, N-ethyl-N- [CH _{(CH3) 2]} aminomethyl, N-butyl N-ethylaminomethyl, N-ethyl N- (1-methylpropyl) aminomethyl, N-ethyl-N- (2-methylpropyl) aminomethyl, N-ethyl-N- [C _{(CH3) 3]} aminomethyl, N- [CH _{(CH3) 2]} N propylaminomethyl, N-butyl-N-propylaminomethyl, N- (1-methylpropyl) -N-propylaminomethyl, N- (2-methylpropyl) -N-propylaminomethyl, N- [C _{(CH3) 3]} -N-propylaminomethyl, N- butyl-N- (1-methylethyl) aminomethyl, N- [CH _{(CH3) 2]} -N- (1-methylpropyl) aminomethyl, N- [CH _{(CH3) 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, Ν, Ν-dimethylaminoethyl, Ν, Ν- diethylaminoethyl, N, N-di (n-propyl) aminoethyl, N, Ndi [CH (CH ₃ ) ₂ ] aminoethyl, Ν, Ν-dibutylaminoethyl, N, N-di (1-methylpropyl) aminoethyl, N, N-di (2-methylpropyl) aminoethyl, N, N-di [C _(CH3) 3] aminoethyl, N-ethyl-N-methylaminoethyl, N-methyl-N-propylaminoethyl, N-methyl-N- [CH (CH 3) 2 aminoethyl, N-butyl-N-methylaminoethyl, N-methyl-N- (1-methylpropyl) aminoethyl, N-methyl-N- (2-methylpropyl) aminoethyl, N- [C (CH3) 3] -N-methylaminoethyl , N-ethyl-N-propylaminoethyl, N-ethyl-N [CH (CH3) 2] aminoethyl, N-butyl-N-ethylaminoethyl, N-ethyl-N- (1-methylpropyl) aminoethyl, N-ethyl-N- (2-methylpropyl) aminoethyl, N-ethyl-N- [C _(CH3) 3] aminoethyl, N- [CH _(CH3) 2] -Npropylaminoetyl, N-butyl-N-propylaminoethyl, N- (1-methylpropyl ) -N-propylaminoethyl, N- (2-methylpropyl) -N-propylaminoethyl, N- [C (CH3) 3] -N-propyl dinoethyl, N-butyl-N [CH _{(CH3) 2]} aminoethyl, N- [CH _{(CH3) 2]} -N- (1-methylpropyl) aminoethyl, N- [CH _{(CH3) 2]} -N- ( 2-methylpropyl) aminoethyl, N- [C (CH3) 3] -N- [CH (CH3) 2] aminoethyl, N-butyl-N- (1-methylpropyl) aminoethyl, N-butyl-N- (2-methylpropyl) aminoethyl, N-butyl-N- [C _(CH3) 3] aminoethyl, N- (1-methylpropyl) -N- (2-methylpropyl) aminoethyl, N- [C (CH3) 3] -N- (1- methyl propyl) aminoethyl or N- [C (CH 3) 3] -N- (2-methylpropyl) aminoethyl, especially N, N dimethylaminoethyl or Ν, Ν-diethylaminoethyl;

di (C 1 -C ₄ -alkyl) aminocarbonyl: CO-N (CH ₃ ) ₂ , 00-Ν (0 ₂ Η ₅ ), CO-N (CH ₂ -C ₂ H ₅ ) 2, CO N [CH (CH ₃ ) 2] 2, Ν, Ν-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] ₂₁ N-ethyl-N-methylaminocarbonyl, N-methyl-N-propyl aminocarbonyl, N-methyl-N- [CH _(CH3) 2] aminocarbonyl, N-butyl-N-methylamino carbonyl, N-methyl-N- ( 1-methylpropyl) aminocarbonyl, N-methyl-N- (2-methylpropyl) aminocarbonyl, N- [C (CH3) 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-ethyl-N [C (CH) ₃ ) 3] aminocarbonyl, N- [CH (CH ₃ ) 2] -N-propylaminocarbonyl, N-butyl-N-propyl aminocarbonyl, N- (1-methylpropyl) -N-propylaminocarbonyl, N- (2-methylpropyl) ) -N propylaminocarbonyl, N- [C _(CH3) 3] -N-propylaminocarbonyl, N-butyl-N- [CH _{(CH3) 2]} aminocarbonyl, N- [CH _{(CH3) 2]} -N- ( 1-methylpropyl) aminocarbonyl, N- [CH _{(CH3) 2]} -N- (2-methylpropyl) aminocarbonyl, N- [C _(CH3) 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 _{(CH3) 3]} -N- (1-methylpropyl) aminocarbonyl or N- [C _{(CH3) 3]} -N- ( 2-methylpropyl) aminocarbonyl, preferably CO-N (CH ₃ ) 2 or CO-N (C ₂ H 5) ₂ ;

di (C 1 -C 6 -alkyl) aminocarbonyl: one of the above di (C ₁ -C ₄ -alkyl) aminocarbonyl radicals, for example N (CH ₃ ) - (n-C 5 H n), N f C ₂ H 5 Xn-C 5 H n, N (CH ₂ -C ₂ H) ₅ ) (nC ₅ H 11), N (n C ₄ H ₉ ) - (n C ₅ H 11), Nin-C ₅ H 11 X 11 -C ₈ H ₁₁ ), N (n C ₆ H ₃ ) - (n C ₅ H ₁₁ ),

N _(CH3) - (n-C ₆ Hi _3), N (C ₂ H ₅₎ - (n-C ₆ Hi _3), N (CH 2 C ₂ H 5) - (n-C ₆ Hi _3), N (n-C ₄ H ₉ 1 - (nC ₆ H ₁₃ ), N (n-C 5 H 11) - (n C ₆ H ₃ ) or N (n C ₆ H ₃ ) ₂ ;

di (C ₁ -C ₄ -alkyl) aminocarbonyl-C 1 -C ₄ -alkyl: C 1 -C ₄ -alkyl, which is substituted with di (C 1 -C ₄ -alkyl) aminocarbonyl as mentioned above, preferably CON (CH ₃ ) ₂ or CO-N (C ₂ H ₅ ) ₂ , e.g. 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) phosphonyl-C 1 -C ₄ -alkyl: C 1 -C ₄ -alkyl which is substituted with di (C 1 -C ₄ alkyl) phosphonyl, for example -PO (OCH ₃ ) ₂ , -PO ( OC ₂ H 5) ₂ , Ν, Ν-dipropylphosphonyl, N, Ndi (1-methylethyl) phosphonyl, Ν, Ν-dibutylphosphonyl, N, N-di (1-methylpropyl) phosphonyl, N, Ndi (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-methyl phosphonyl, 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-methyl-ethyl) phosphonyl, N-butyl-N-ethylphosphonyl, N-ethyl-N- (1-methylpropyl) phosphonyl, N-ethyl-N- (2-methylpropyl) 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-dimethylethyl) -N-propylphosphonyl, N-butyl-N- (1-methylethyl) phosphonyl, N- (1-methylethyl) -N- (1-methylpropyl) phosphonyl, N - (1-methylethyl) -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-dimethyl-ethyl) 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 ) ₂ , e.g. 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-methyletenyl, 1-buten-1-yl, 1-buten-2-yl, 1-buten-3-yl, 2-butene- 1-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-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-en-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-1-yl, n-hex-1-en-1-yl, n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4- en-1-yl, n-hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1- yl,

4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-

2-en-1-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-en-1-yl, 2-methylpent-4en-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-Dimethyl-but-3-en-1-yl, 2,3-dimethyl-but-1-en-1-yl, 2,3-dimethyl-but-2-en-1-yl, 2,3-dimethyl-but-3-en-1- yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1- yl, 1-ethyl-but-3-en-1-yl, 2-ethyl-but-1-en-1-yl, 2-ethyl-but-2-en-1-yl, 2-ethyl-but-3-en-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 or 1- ethyl-2-methylprop-2-en-1-yl;

C ₃ -C ₆ -haloalkenyl: C ₃ -C 6 -alkenyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, e.g. 2- <chloralyl,

3-chloroalyl, 2,3-dichloroalyl, 3,3-dichloroalyl, 2,3,3-trichloralyl, 2,3-dichlorobut-2-enyl, 2-bromalyl, 3-bromalyl, 2,3-dibromalyl, 3, 3-dibromalyl, 2,3,3-tribromalyl or 2,3-dibromobut-2-enyl;

cyano-C ₃ -C 6 -alkenyl: for example 2-cyanoalyl, 3-cyanoalyl, 4-cyanobut-2enyl, 4cyanobut-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-yn-3-yl 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-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2- In-5-yl, 3-methylbut-1-in-3-yl, 3-methylbut-1-in-4-yl, n-hex-1-in-1-yl, n-hex-1-in-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, n23 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 and 4-methylpent-2-yn-5-yl, preferably prop-2-yn-1-yl;

C ₃ -C ₆ -haloalkynyl: _{C3 -C6} -alkynyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, e.g. 1,1-difluoroprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1- yl, 5-fluoropent-3-yn-1-yl or 6-fluorohex-4-yn-1-yl;

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

C ₃ -C 4 -alkenyloxy-C 1 -C 4 -alkyl: C 1 -C ₄ -alkyl, which is substituted by C 3 -C ₄ -alkenyloxy, for example allyloxy, but-1-en-3-yloxy, but-1-en-4 -yloxy, but-2-en-1-yloxy, 1-methylprop-2-enyloxy or 2-methylprop-2-enyloxy, e.g., allyloxymethyl, 2alyloxyethyl or but-1-en-4-yloxymethyl, especially 2-allyloxyethyl;

C3-C4-alkynyloxy-Ci-C4-alkyl: C4-alkyl which is substituted by C ₃ -C 4 alkynyloxy, such as propargyloxy, but-1-yn-3-yloxy, but-1-yn-4-yloxy, but 2-in-1-yloxy,

1-methylprop-2-ynyloxy or 2-methylprop-2-ynyloxy, preferably propargyloxy, i. for example propargyloxymethyl or 2-propargyloxyethyl, in particular 2-propargyloxyethyl;

C ₃ -C ₄ -alkenylthio-C 1 -C 4 -alkyl: C 1 -C ₄ -alkyl which is substituted by C 3 -C 4 alkenylthio, for example allylthio, but-1-en-3-ylthio, but-1-en-4- ylthio, but-2-en-1-ylthio, 1-methylprop-2-enylthio or 2-methylprop-2-enylthio, e.g., allylthiomethyl, 2alythioethyl or but-1-en-4-ylthiomethyl, especially 2- (allythio) ethyl;

C4alkinyltio C3-C, -C4-alkyl, Ci-C ₄ -alkyl, which is substituted by C 3 C4alkinyltio, such as propargylthio, but-1-yn-3-ylthio, but-1-yn-4-ylthio, but-2-yn-1-ylthio, 1-methylprop-2-ynylthio or 2-methylprop-2-ynylthio, preferably propargylthio, e.g., propargylthiomethyl or 2-propargylthioethyl, especially 2- (propargylthio) ethyl;

C ₃ -C ₄ -alkenylsulfinyl-C ₁ -C ₄ alkyl: _Ci-C4-alkyl which is substituted by C 3 C4alkenylsulfinylom, for example allylsulfinyl, but-1-en-3-ylsulfinyl, but-1-en-4 -ylsulfinyl, but-2-en-1-ylsulfinyl, 1-methylprop-2-enylsulfinyl or 2-methylprop-2-enylsulfinyl,

i for example allylsulfinylmethyl, 2-allylsulfinylethyl or but-1-en-4-ylsulfinylmethyl, in particular 2- (allylsulfinyl) ethyl;

C 3 -C 4 -alkynylsulfinyl-C4-alkyl. C 1 -C 4 -alkyl which is substituted with C 3 -C 4 alkynylsulfinyl, for example propargylsulfinyl, but-1-yn-3-ylsulfinyl, but-1-yn-4-ylsulfinyl, but-2-yn-1-ylsulfinyl, 1-methylprop-2-ynylsulfinyl or 2-methylprop-2-ylsulfinyl, preferably propargylsulfinyl, i for example propargylsulfinylmethyl or

2-propargylsulfinylethyl, especially 2- (propargylsulfinyl) ethyl;

C ₃ -C 4 -alkenylsulfonyl-C 1 -C 4 -alkyl: C 1 -C 4 -alkyl which is substituted with C ₃ -C 4 alkenylsulfonyl, for example allylsulfonyl, but-1-en-3-ylsulfonyl, but-1-en-4-ylsulfonyl, but-2-ene -1-ylsulfonyl, 1-methylprop-2-enylsulfonyl or 2-methylprop-2enylsulfonyl, e.g., allylsulfonylmethyl, 2-allylsulfonylethyl or but-1-en-4-ylsulfonylmethyl, especially 2- (allylsulfonyl) ethyl;

C 3 -C ₄ -alkynylsulfonyl-C4-alkyl: _Ci-C4-alkyl which is substituted by C 3 C4alkinylsulfonylom, such as propargylsulfonyl, but-1-yn-3-ylsulfonyl, but-1-yn-4ylsulfonyl, but-2- in-1-ylsulfonyl, 1-methylprop-2-ynylsulfonyl or 2-methylprop-2-ylsulfonyl, preferably a propargylsulfonyl group, e.g., propargylsulfonylmethyl or 2-propargylsulfonylethyl, especially 2- (propargylsulfonyl) ethyl;

C 3 -C ₆ -cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or 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- (cyclopropyl) 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- (cyclobutyl) hexyl, 6- (cyclopentyl) hexyl, 6 - (cyclohexyl) hexyl, 6- (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-cyclopropyloxybutyl- 1-yl, 2-cyclopropyloxybut-1-yl, 3-cyclopropyloxybut-1-yl, 4-cyclopropyloxybut-1-yl, 1-cyclopropyloxybut-2-yl, 2-cyclopropyloxybut-2-yl, 3-cyclopropyloxybut-2 yl, 3-cyklopropyloxybut-2-yl, 4-cyklopropyloxybut-2-yl, 1 - (cyclopropyloxymethyl) eth-l-yl, 1 - (cyclopropyloxymethyl) -l _(CH3) 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-yl, 2- cyclobutyloxybut-1-yl, 3-cyclobutyloxybut-1-yl, 4-cyclobutyloxybut-1-yl, 1-cyclobutyloxybut-2-yl, 2-cyclobutyloxybut-2-yl, 3-cyclobutyloxybut-2-yl, 3-cyclobutyloxybut- 2-yl, 4-cyklobutyloxybut-2-yl, 1 - (cyclobutyloxymethyl) eth-l-yl, 1 - (cyclobutyloxymethyl) -l - _(CH3) eth-1-yl, 1 - (cyclobutyloxymethyl) prop-1- y 1, cyclopentyloxymethyl, 1-cyclopentyloxyethyl, 2-cyclopentyloxyethyl, 1-cyclopentyloxyprop-1-yl, 2-cyclopentyloxyprop-1-yl, 3-cyclopentyloxyprop-1-yl, 1-cyclopentyloxybut-1-yl, 2-cyclopentyloxybut-1- yl, 3-cyclopentyloxybutyl

1-yl, 4-cyclopentyloxybut-1-yl, 1-cyclopentyloxybut-2-yl, 2-cyclopentyloxybut-2-yl,

3-cyklopentyloxybut-2-yl, 3-cyklopentyloxybut-2-yl, 4-cyklopentyloxybut-2-yl, 1 (-cyclopentyloxymethyl) eth-l-yl, 1 - (-cyclopentyloxymethyl) -l - _(CH3) 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-cyklohexyloxybut-2-yl, 3-cyklohexyloxybut-2-yl, 4-cyklohexyloxybut-2-yl, 1- (cyclohexyloxymethyl) eth-1-yl, 1 - (cyclohexyloxymethyl) -l - _(CH3) eth-1 1- yl, 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, 3-cykloheptyloxybut-2-yl, 4-cykloheptyloxybut-2-yl, 1- (cykloheptyloxymetyl) eth-1-yl, 1 - (cykloheptyloxymetyl) -l - _(CH3) eth-1-yl, 1 - (cycloheptyloxymethyl) prop-1-yl, cyclooctyloxymethyl, 1-cyclooctyloxyethyl, 2-cyclooctyloxyethyl, 1cyclooctyloxyprop-1-yl, 2-cyclooctyloxyprop-1-yl, 3-cyclooctyloxyprop-1-yl, 1-cyclooctyloxybut-1-yl, 2-a yclooktyloxybut-1-yl, 3-cyclooctyloxybut-1-yl, 4-cyclooctyloxybut-1-yl, 1-cyclooctyloxybut-2-yl, 2-cyclooctyloxybut-2-yl, 3-cyclooctyloxybut-2-yl, 3-cyclooctyloxybut-2- yl, 4-cyclooctyloxybut-2-yl, 1- (cyclooctyloxymethyl) et-1-yl,

1- (cyclooctyloxymethyl) -1- (CH ₃ ) et-1-yl or 1- (cyclooctyloxymethyl) prop-1-yl, in particular C ₃ -C 6 -cycloalkoxymethyl or 2- (C ₃ -C ₆ -cycloalkoxy) ethyl,

3- to 7-membered heterocyclyl means not only a saturated, partially or fully unsaturated, but also an aromatic heterocycle having one to three heteroatoms selected from the group consisting of the following:

one to three nitrogen atoms, one to two oxygen atoms, and one or two sulfur atoms.

Examples of saturated heterocycles that may contain carbonyl or thiocarbonyl in the ring are:

oxiranyl, thiiranyl, aziridin-1-yl, aziridin-2-yl, diaziridin-1-yl, diaziridin-3-yl, oxethan-

2-yl, oxethan-3-yl, thietan-2-yl, thietan-3-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3- yl, tetrahydrothiophen-2-yl, tetrahydrothiophen-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4- yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-oxazolidin-2-yl, 1,3-oxazolidin-3-yl, 1,3-oxazolidin-4-yl, 1,3-oxazolidin-5-yl, 1,2-oxazolidin-2-yl, 1,2-oxazolidin-

3-yl, 1,2-oxazolidin-4-yl, 1,2-oxazolidin-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-5-yl, tetrahydropyrazol-1-yl, tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-

4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydropyran-4-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, 1,3-dioxane- 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, hexahydropyridazin-1-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazine- 1-yl, piperazin-2-yl, piperazin-3-yl, hexahydro-1,3,5-triazin-1-yl, hexahydro-1,3,5-triazin-2-yl, oxepan-2-yl, oxepan- 3-yl, oxepan-4-yl, thiopan-2-yl, thiopan-3-yl, thiopan-4-yl, 1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl, 1, 3-dioxepan-5-yl, 1,3-dioxepan-6-yl, 1,3-ditiepan-2-yl, 1,3-ditiepan-2-yl, 1,3-ditiepan-2-yl, 1,3- ditiepan-2-yl,

1,4-dioxepan-2-yl, 1,4-dioxepan-7-yl, hexahydroazepin-1-yl, hexahydroazepin-2-yl, hexahydroazepin-3-yl, hexahydroazepin-4-yl, hexahydro-1,3- diazepin-1-yl, hexahydro-1,3-diazepin-2-yl, hexahydro-1,3-diazepin-4-yl, hexahydro-1,4-diazepin-1-yl, and hexahydro-1,4-diazepine- 2-yl.

Examples of unsaturated heterocycles that may contain carbonyl or thiocarbonyl in the ring are: dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl, 1,3oxazolin-2-yl;

Preferred among heteroaromatic rings are 5- and 6-membered rings, e.g. furyl such as 2-furyl and 3-furyl, thienyl such as 2-thienyl and 3-thienyl, pyrrolyl such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl 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, thiazolyl such as 2-thiazolyl, 4-thiazolyl and 5-thiazolyl, imidazolyl such as 2-imidazolyl and 4-imidazolyl, oxadiazolyl such as 1,2,4oxadiazol-3-yl, 1,2 , 4-oxadiazol-5-yl and 1,3,4-oxadiazol-2-yl, thiadiazolyl such as e.g.

1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl and 1,3,4-thiadiazol-2-yl, triazolyl such as

1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl and 1,2,4-triazol-4-yl, pyridinyl such as 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl such as 3-pyridazinyl and 4-pyridazinyl, pyrimidinyl such as 2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl;

2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, in particular pyridyl, pyrimidyl, furanyl and thienyl.

All phenyl, carbocyclic and heterocyclic rings are preferably unsubstituted.

Preferred for use of the 3- (benzazol-4-yl) pyrimidinedione derivatives I as herbicides are those compounds I wherein the variables have the following meanings, in each case alone or in combination:

X is oxygen;

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, C6-alkyl, Cl-C6-haloalkyl or Ci-Ce-alkylsulfonyl, in particular trifluoromethyl;

R ³ is hydrogen;

R ⁴ is hydrogen, fluoro or chloro;

R ⁵ is cyano or halogen, especially chlorine;

= Y- is = NN (R ⁶ ) - or = C (ZR ⁷ ) -5-, especially = 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 C 1 -C ₆ -alkyl, which may be substituted by the following: cyano, (C 1 -C 6 -alkoxy) carbonyl, di (C 1 -C ₆ -alkyl) aminocarbonyl or (C 1 -C 6 -alkyl) carbonyloxy, in particular C 1 -C 6 _6- alkyl, C ₃ -C ₆ -alkynyl, C ₁ -C ₆ -alkylsulfonyl or (C 1 -C 6 -alkoxy) carbonyl,

Especially preferred are 3- (benzazol-4-yl) pyrimidinedione derivatives Ia = {I, wherein X = O, ^R1 = methyl, ^R2 = trifluoromethyl, ^R3 = H, ^R4 = fluoro, ^R5 = chloro and = = Y = C (ZR ⁷⁾ -N _(CH3) -}

especially compounds 1a. 1 to la.272, which are as follows:

Table 1

No. -ZR ⁷ IA.1 -H la.2 -ch ₃ la.3 -c ₃ h ₅ la.4 -nC ₃ H7 la.5 CH _{(CH3) 2} la.6 -nC ₄ H9 la.7 -CH ₂ -CH (CH ₃ ) ₂ la.8 -CH (CH ₃ ) -C ₂ H ₅ la.9 -C (CH ₃ ) ₃ la.10 -ch ₂ -ch = ch ₂ la.11 -ch ₂ -ch = ch-ch ₃ la.12 -ch ₂ -ch ₂ -ch = ch ₂ la.13 -ch ₂ -c = ch la.14 -ch ₂ -och ₃ la.15 -ch ₂ -ch ₂ -och ₃ la.16 -ch ₂ -cn

No. -ZR ⁷ Ia. 17 -CH ₂ -CH ₂ F la.18 -CH CFA Ia. 19 -CH ₂ -CH ₂ Cl la.20 CH2-CO-OCH3 la.21 -CH ₂ -CO-OC ₂ H ₅ la.22 -CH ₂ -CO-N (CH ₃ ) ₃ la.23 cyclobutyl la.24 cyclopentyl la.25 cyclohexyl la.26 phenyl la.27 -CH ₂ -cyclobutyl la.28 -CHrcyklopentyl la.29 -CH ₂ -cyclohexyl la.30 -CH ₂ -phenyl la.31 -no ₂ la.32 CN la.33 -F Ia. 34 -CI la.35 Br la.36 -och ₃ la.37 -OC ₂ H ₅ la.38 -O (nC ₃ H ₇ ) la.39 -OCH (CH _{3) 2} la.4O -O (nC ₄ H ₉ ) la.41 -OCH 2 -CH (CH ₃ ) ₂ la.42 -OCH (CH ₃ ) -C ₂ H ₅ la.43 OC _{(CH3) 3} la.44 -och ₂ -ch = ch ₂ la.45 -OCH 2 -CH = CH-CH ₃ la.46 -och ₂ -ch ₂ -ch = ch ₂ la.47 -OCH (CH ₃ ) -CH = CH ₂ la.48 -OCH2-C-CH la.49 -OCH (CH ₃ ) -C =CH la.50 -och ₂ -och ₃ la.51 -OCH ₂ -CH ₂ -OCH ₃ la.52 -och ₂ -cn la.53 -och ₂ -ch ₂ f la.54 -och ₂ -cf ₃ la.55 -och ₂ -co-och ₃ Ia. 56 -och ₂ -co-oc ₂ h ₅ la.57 -OCH ₂ -CO-N (CH ₃ ) ₂ la.58 O-cyclobutyl la.59 O-cyclopentyl la.60 O-cyclohexyl la.61 -O-phenyl la.62 -OCH ₂ -cyclobutyl la.63 -OCH ₂ -cyclopentyl

No. -ZR ⁷ la.64 -OCH 2 -cyclohexyl la.65 -OCH 2 phenyl la.66 -CH 2 -OH la.67 CH2-OCH 3 la.68 -nh ₂ la.69 NHCH3 la.70 -N (CH ₃ ) ₂ la.71 NH-C ₂ H ₅ la.72 -N (C ₃ H ₅ ) ₂ la.73 -NH- (nC ₃ H ₇ ) la.74 -N (nC ₃ H ₇ ) ₂ la.75 -NH- (nC ₄ H ₉ ) la.76 -N (nC ₄ H ₉ ) ₂ la.77 -NH-CH (CH _{3) 2} la.78 N [CH _{(CH3) 2] 2} la.79 -NH-CH ₂ -CH (CH 3) 2 la.80 -N (CH ₂ -CH (CH ₃ ) 2) 2 la.81 -nh-ch ₂ -ch = ch ₂ la.82 -N (CH ₂ -CH = CH ₂ ) 2 la.83 -NH-CH ₂ OCH la.84 -N (CH ₂ -C =CH) ₂ la.85 -CH ₂ -N (CH ₃ ) ₂ la.86 SH la.87 SCH3 la.88 -sc ₂ h ₅ la.89 -S- (nC ₃ H ₇ ) la.90 -S- (nC ₄ H ₉ ) la.91 -SCH _{(CH3) 2} la.92 -SCH ₂ -CH (CH ₃ ) ₂ la.93 -SCH (CH ₃ ) -C ₂ H ₅ la.94 -S-C (CH _{3) 3} la.95 -sch ₂ -ch = ch ₂ la.96 -sch ₂ -ch = ch-ch ₃ la.97 -SCH ₂ -CH ₂ -CH = CH ₂ la.98 -SCH _(CH3) -CH = CH ₂ la.99 -SCH 2-OCH Ia. 100 -SCH _(CH3) -C-CH la.101 -sch ₂ -och ₃ Ia. 102 -SCH ₂ CH ₂ OCH ₃ Ia. 103 -SCH 2-CN la.104 -SCH 2-CH 2 F Ia. 105 -sch ₂ -cf ₃ Ia. 106 -SCH 2-CH 2 Cl Ia. 107 -SCH ₂ -CO-OCH ₃ Ia. 108 -SCH 2-CO-OC2H5 Ia. 109 -SCH ₂ -CO-N (CH ₃ ) ₂

No. -ZR ⁷ Ia.110 -S-cyclobutyl la.111 S-cyclopentyl la.112 S-cyclohexyl la.113 S-phenyl la.114 -SCH 2-cyclobutyl la.115 -SCH 2-cyclopentyl la.116 -SCH 2-cyclohexyl la.117 -SCH ₂ -phenyl la.118 CH2-SCH3 la.119 -SO-CH 3 Ia. 120 -SO-C2H5 la.121 -SO- (n-C ₃ H ₇₎ Ia. 122 -SO- (nC ₄ H ₉ ) Ia. 123 -SO-CH _{(CH3) 2} Ia. 124 -SO-CH ₂ -CH (CH ₃ ) ₂ Ia. 125 -SO-CH (CH ₃₎ -C ₂ H ₅ Ia. 126 -SO-C _{(CH3) 3} Ia. 127 -so-ch ₂ -ch = ch ₂ la.128 -so-ch ₂ -ch = ch-ch ₃ la.129 -so-ch ₂ -ch ₂ -ch = ch ₂ Ia. 130 -SO-CH _(CH3) CH = _CH2 la.131 -SO-CH ₂ -C = CH Ia. 132 -SO-CH (CH ₃ ) -C ₅ CH Ia. 133 -so-ch ₂ -och ₃ Ia. 134 -so-ch ₂ -ch ₂ -och ₃ Ia. 135 -so-ch ₂ -cn Ia. 136 -so-ch ₂ -ch ₂ f Ia. 137 -SO-CH 2 -CF 3 Ia. 138 -so-ch ₂ -ch ₂ or Ia. 139 -so-ch ₂ -co-och ₃ Ia. 140 -so-ch ₂ -co-oc ₂ h ₅ la.141 -SO-CH ₂ -CO-N (CH ₃ ) ₂ Ia. 142 -SO-cyclobutyl Ia. 143 -SO-cyclopentyl la.144 -SO-cyclohexyl la.145 -SO-phenyl Ia. 146 _{-SO-CH2-cyclobutyl} Ia. 147 -SO-CH ₂ -cyclopentyl la.148 -SO-CH ₂ -cyclohexyl Ia. 149 _{-SO-CH2-phenyl} Ia. 150 -CH ₂ -SO-CH ₃ la.151 -so ₂ -ch ₃ Ia. 152 -SO ₂ -C ₂ H ₅ Ia. 153 -SO ₂ - (nC ₃ H ₇ ) Ia. 154 -SO ₂ - (nC ₄ Hg) Ia. 155 -SO ₂ -CH (CH ₃ ) ₂ Ia. 156 -SO ₂ -CH ₂ -CH (CH ₃ ) ₂

c. -ZR ⁷ Ia. 157 -SO ₂ -CH (CH ₃ ) -C ₂ H ₅ Ia. 158 -SO ₂ -C (CH ₃ ) ₃ Ia. 159 -so ₂ -ch ₂ -ch = ch ₂ Ia. 160 -so ₂ -ch ₂ -ch = ch-ch ₃ la.161 -so ₂ -ch ₂ -ch ₂ -ch = ch ₂ Ia. 162 -SO ₂ -CH (CH ₃ ) -CH = CH ₂ Ia. 163 -so ₂ -ch ₂ -c = ch Ia. 164 -SO ₂ -CH (CH ₃ ) -C =CH Ia. 165 -so ₂ -ch ₂ -och ₃ Ia. 166 -so ₂ -ch ₂ -ch ₂ -och ₃ Ia. 167 -With ₂ CH ₂ CN Ia. 168 -so ₂ -ch ₂ -ch ₂ f Ia. 169 _{-SO2 -CH2 -CF3} Ia. 170 -so ₂ -ch ₂ -ch ₂ ci la.171 -so ₂ -ch ₂ -co-och ₃ Ia. 172 _{-SO2-CH 2} -CO-OC _{2 H5,} Ia. 173 -SO ₂ -CH ₂ -CO-N (CH ₃ ) ₂ Ia. 174 -SO ₂ -cyclobutyl Ia. 175 -SO ₂ -cyclopentyl Ia. 176 -SO ₂ -cyclohexyl Ia. 177 -SO ₂ -phenyl Ia. 178 -SO ₂ -CH ₂ -cyclobutyl Ia. 179 -SO ₂ -CH ₂ -cyclopentyl Ia. 180 -SOrCHrcyklohexyl la.181 -SOrCHrfenyl Ia. 182 -CH ₂ -SO ₂ -CH ₃ Ia. 183 -CH ₂ -CH (Cl) -CO-OH Ia. 184 -CH ₂ -CH (CI) -CO-OCH ₃ Ia. 185 -CH ₂ -CH (CI) -CO-OC ₂ H ₅ Ia. 186 -CH ₂ -CH (CI) -CO-O (nC ₃ H ₇ ) Ia. 187 -CH ₂ -CH (CI) -CO-O (nC ₄ H ₉ ) Ia. 188 -CH ₂ -CH (CI) -CO-OCH (CH ₃ ) ₂ Ia. 189 -CH ₂ -CH (CI) -CO-OCH ₂ -CH (CH ₃ ) ₂ Ia. 190 -CH ₂ -CH (CI) -CO-OCH (CH ₃ ) -C ₂ H ₅ la.191 -CH ₂ -CH (CI) -CO-OC (CH ₃ ) ₃ Ia. 192 -CH ₂ -CH (Br) -CO-OH Ia. 193 -CH ₂ -CH (Br) -CO-OCH ₃ Ia. 194 -CH ₂ -CH (Br) -CO-OC ₂ H ₅ Ia. 195 -CH ₂ -CH (Br) -CO-O (nC ₃ H ₇ ) Ia. 196 -CH ₂ -CH (Br) -CO-O (nC ₄ H ₉ ) Ia. 197 -CH ₂ -CH (Br) -CO-OCH (CH ₃ ) ₂ Ia. 198 -CH ₂ -CH (Br) -CO-OCH ₂ -CH (CH ₃ ) ₂ Ia. 199 -CH ₂ -CH (Br) -CO-OCH (CH ₃ ) -C ₂ H ₅ la.200 -CH ₂ -CH (Br) -CO-OC (CH ₃ ) ₃ la.201 -CH = CH-CO-OH la.202 -ch = ch-co-och ₃ la.203 CH = CH-CO-OC _{2 H5,}

No. -ZR ⁷ la.204 -CH = CH-CO-O (nC ₃ H ₇ ) la.205 -CH = CH-CO-O (nC ₄ H ₉ ) la.206 -CH = CH-CO-OCH _(CH3) 2 la.207 -CH = CH-CO-OCH ₂ -CH (CH ₃ ) ₂ la.208 -CH = CH-CO-OCH (CH ₃ ) -C ₂ H ₅ Ia. 209 -CH = CH-CO-OC (CH ₃ ) ₃ la.210 CH = C (Cl) -CO-OH la.211 -CH = C (Cl) -CO-OCH ₃ la.212 -CH = C (Cl) -CO-OC ₂ H ₅ la.213 -CH = C (Cl) -CO-O (nC ₃ H ₇ ) la.214 -CH = C (Cl) -CO-O (nC ₄ H ₉ ) la.215 -CH = C (Cl) -CO-OCH (CH ₃ ) ₂ la.216 -CH = C (Cl) -CO-OCH ₂ -CH (CH ₃ ) ₂ la.217 -CH = C (Cl) -CO-OCH (CH ₃ ) -C ₂ H 5 la.218 -CH = C (Cl) -CO-OC (CH ₃ ) ₃ la.219 CH = C (Br) -CO-OH la.220 -CH = C (Br) -CO-OCH ₃ la.221 -CH = C (Br) -CO-OC ₂ H ₅ la.222 -CH = C (Br) -CO-O (nC ₃ H ₇ ) la.223 -CH = C (Br) -CO-O (nC ₄ H ₉ ) la.224 -CH = C (Br) -CO-OCH (CH ₃ ) 2 la.225 -CH = C (Br) -CO-OCH ₂ -CH (CH ₃ ) ₂ la.226 -CH = C (Br) -CO-OCH (CH ₃ ) -C ₂ H ₅ la.227 -CH = C (Br) -CO-OC (CH ₃ ) ₃ la.228 -CH ₂ -CH (Cl) -CO-NH ₂ la.229 -CH ₂ -CH (Cl) -CO-NH-CH ₃ la.230 -CH 2 -CH (Cl) -CO-N (CH ₃ ) ₂ la.231 -CH 2 -CH (Cl) -CO-NH-C ₂ H ₅ la.232 -CH 2 -CH (Cl) -CO-N (C ₂ H 5) 2 la.233 -CH 2 -CH (CI) -CO-NH- (nC ₃ H ₇ ) la.234 -CH ₂ -CH (Cl) -CO-N (nC ₃ H ₇ ) ₂ la.235 -CH ₂ -CH (CI) -CO-NH- (nC ₄ H ₉ ) la.236 -CH ₂ -CH (Cl) -CO-N (nC ₄ H ₉ ) 2 la.237 -CH ₂ -CH (Br) -CO-NH ₂ la.238 -CH 2 -CH (Br) -CO-NH-CH ₃ la.239 -CH ₂ -CH (Br) -CO-N (CH ₃ ) 2 la.240 -CH ₂ -CH (Br) -CO-NH-C ₂ H ₅ la.241 -CH 2 -CH (Br) -CO-N (C ₂ H ₅ ) 2 Ia. 242 -CH ₂ -CH (Br) -CO-NH- (nC ₃ H ₇ ) la.243 -CH ₂ -CH (Br) -CO-N (nC ₃ H ₇ ) 2 la.244 -CH 2 -CH (Br) -CO-NH- (nC ₄ H ₉ ) la.245 -CH ₂ -CH (Br) -CO-N (nC ₄ H ₉ ) ₂ la.246 -ch = ch-co-nh ₂ la.247 -ch = ch-co-nh-ch ₂ la.248 -CH = CH-CO-N (CH ₃ ) 2 la.249 CH = CH-CO-NH-C ₂ H ₅ la.250 -CH = CH-CO-N (C ₂ H ₅ ) ₂

No. -ZR ⁷ la.251 -CH = CH-CO-NH- (nC ₃ H ₇ ) la.252 -CH = CH-CO-N (nC ₃ H ₇ ) ₂ la.253 -CH = CH-CO-NH- (nC ₄ H ₉ ) Ia. 254 -CH = CH-CO-N (nC ₄ H ₉ ) ₂ la.255 -CH = C (Cl) -CO-NH ₂ la.256 -CH = C (Cl) -CO-NH-CH ₃ la.257 -CH = C (Cl) -CO-N (CH ₃ ) ₂ la.258 -CH = C (Cl) -CO-NH-C ₂ H ₅ la.259 -CH = C (Cl) -CO-N (C ₂ H ₅ ) ₂ la.260 -CH = C (CI) -CO-NH- (nC ₃ H ₇ ) la.261 -CH = C (Cl) -CO-N (nC ₃ H ₇ ) ₂ la.262 -CH = C (Cl) -CO-NH- (nC ₄ H ₉ ) la.263 -CH = C (Cl) -CO-N (nC ₄ H ₉ ) ₂ la.264 -CH = C (Br) -CO-NH ₂ la.265 -CH = C (Br) -CO-NH-CH ₃ la.266 -CH = C (Br) -CO-NH (CH ₃ ) ₂ la.267 -CH = C (Br) -CO-NH-C ₂ H ₅ la.268 -CH = C (Br) -CO-N (C ₂ H ₅ ) ₂ la.269 -CH = C (Br) -CO-NH- (nC ₃ H ₇ ) la.270 -CH = C (Br) -CO-N (nC ₃ H ₇ ) ₂ la.271 -CH = C (Br) -CO-NH- (nC ₄ H ₉ ) la.272 -CH = C (Br) -CO-N (nC ₄ H ₉ ) ₂

Particularly preferred 3- (benzazol-4-yl) pyrimidinedione derivatives are those of the formulas Ib to Ih, in particular compounds 1b.1-1b.272, which differ from the corresponding compounds 1a. 1-la.272 only by the fact that R ⁴ is hydrogen:

(Ib) Compound Ic. 1 - 1c.272, which differ from the corresponding compounds Ia - Ia - 272 only in that R ¹ is hydrogen:

H 0 N — ζ ^F 3 ^C - <N- 0 n ^ _/ n-ch ₃ zr7 "v (ic)

compounds 1d.1 - 1d.272, which differ from the corresponding compounds 1a.1 - 1a.272 only in that R ¹ and R ⁴ are hydrogen:

H O

\ l— FsC-n ' ^ 0 ' 0 N ^ N-CH 2 ^ZR? dd)

compounds le.1 - le.272, which differ from the corresponding compounds 1a.1 - la.272 only in that Y is = C (ZR ⁷ ) -N (SO ₂ CH ₃ ) -:

H ₃ C 0 H F ₃ C — C N- clay · " 0 N ^ N-SO ₂ -CH ₃ ZR 7 (Ie)

compounds 1f.1 - 1f.272, which differ from the corresponding compounds 1a.1 - 1a.272 only in that R ⁴ is hydrogen and Y is = C (ZR ⁷ ) -N (SO ₂ CH 3) -:

H ₃ C 0 ^X N — ζ F _{3 C} ^ f N- S = < ^CI 0 N ^ N-SO 2 ^-CH 2 ^{ZR 7} df)

Ig compounds. 1-72.272, which differ from the corresponding compounds Ia-Ia-1a272 only in that R ¹ is hydrogen and Y is = C (ZR ⁷ ) -N (SO 2 CH 3) -:

of compound Ih. 1 - lh.272, which differ from the corresponding compounds Ia. 1-la.272 only by the fact that R ¹ and R ⁴ is hydrogen and Y is = C (ZR ⁷ ) -N (SO ₂ CH ₃ ) -:

compound li.1 - li.272, which differ from the corresponding compounds la.1 - la.272 only in that Y is = C (ZR ⁷⁾ -O-;

compounds 1k.1 - 1k.272, which differ from the corresponding compounds 1a.1 - 1a.272 only in that = Y- is = C (ZR ⁷ ) -O- and R ⁴ is hydrogen:

H ₃ C 0 ^N y ° ™

compounds Im.1-Im.272, which differ from the corresponding compounds Ia-1a.272 only in that Y is = C (ZR ⁷ ) -O- and R ¹ is hydrogen:

H 0 N- clay · ⁰ ' 0 / \ S ^N ° ZR ^7/1 1 (Im)

compounds In.1 - In.272, which differ from the corresponding compounds Ia. 1-la.272 only by the fact that Y is = C (ZR ⁷ ) -O- and R ¹ and R ⁴ is hydrogen:

H O

N - ^F3C ^ _M ^N - in 0 ^N y ° zr ⁷ (in)

The 3- (benzazol-4-yl) pyrimidinedione derivatives of formula I can be obtained in various ways, for example by one of the following processes:

Procedure A)

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

H 0 R 4 N- ( R2- / N-Y-R5 L ¹ -alkyl or R 10 R 4 MK R ₂ - / _N - / - R 5 U-haloalkyl / in I I R 3 X n -y R3 \ N-Y (0 (R ¹ = H) (II) (1) (R ¹ H, NH ₂₎

L ¹ is typically a leaving group such as halogen, preferably chlorine, bromine or iodine, (halo) alkylsulfonyloxy, preferably methylsulfonyloxy or trifluoromethylsulfonyloxy, arylsulfonyloxy, preferably toluenesulfonyloxy, and alkoxysulfonyloxy, preferably methoxy- and ethoxy-sulfonyloxy.

The process is conveniently carried out in an inert organic solvent, for example a protic solvent such as lower alcohols, preferably methanol or ethanol, optionally mixed with water, or in an aprotic solvent such as an aliphatic or cyclic ether such as methyl tert-butyl ether, 1,2 - dimethoxyethane, tetrahydrofuran and dioxane, in an aliphatic ketone such as acetone, diethyl ketone and ethylmethylketone, in an amide such as dimethylformamide and N-methylpyrrolidone, in a sulfoxide such as dimethylsulfoxide, in a urea such as tetramethylurea and 1,3-dimethyltetrapyrid-2 (1H) carboxylic acid esters such as ethyl acetate or in a halogenated aliphatic or aromatic hydrocarbon such as dichloromethane, dichloroethane, chlorobenzene and dichlorobenzenes.

The process may, if desired, be carried out in the presence of a base, suitable bases being inorganic bases, e.g. carbonates such as sodium carbonate and potassium carbonate, bicarbonates such as sodium bicarbonate and potassium bicarbonate, or alkali metal hydrides such as sodium hydride and potassium hydride, and also organic bases, e.g. amines such as triethylamine, pyridine and Ν, Ν-diethylaniline, or alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide.

The amount of base and alkylating agent II is preferably in each case 0.5 to 2 times the molar amount with respect to the amount of the starting compound I (where R ¹ = hydrogen).

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

A preferred process variant consists in alkylating the salt I obtained by cyclization IV, wherein R ¹ = H, or V, wherein R ¹ = H, according to process D) without isolating it from the reaction mixture, which may still contain excess base, e.g. sodium hydride, sodium alkoxide or sodium carbonate.

If the salts of the compounds I, where R ¹ is hydrogen, cannot be prepared directly by the cyclization under basic conditions described as method D), they can also be obtained in a known manner from products of methods C) to F). To this end, for example, an aqueous solution of an inorganic or organic base is treated with a 3- (benzazol-4-yl) pyrimidinedione derivative I wherein R ¹ is hydrogen. Here, the salt formation is normally sufficiently rapid already at 20-25 ° C.

It is particularly preferred to prepare the sodium salt by dissolving the 3- (benzazol-4-yl) pyrimidinedione derivative I wherein R ¹ = hydrogen in aqueous sodium hydroxide solution at 20-25 ° C using approximately equivalent amounts of 3 (benzazol-4- yl) pyrimidinedione derivative I (wherein R ¹ = H) and sodium hydroxide. The corresponding salt of the 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 whose metal ion is other than the alkali metal ion can usually be prepared by double decomposition of the corresponding alkali metal salt in an aqueous medium and the ammonium, phosphonium, sulfonium and sulfoxonium salts using ammonia or phosphonium, sulfonium or sulfoxonium hydroxides.

Procedure B)

Reaction of a 3- (benzazol-4-yl) pyrimidinedione derivative of formula I wherein R ¹ is hydrogen with an electrophilic amine reagent in the presence of a base:

(I) = {R ¹ NH _2}

An amine reagent which has so far been particularly useful is 2,4-dinitrophenoxyamine, but it is also possible, for example, to use hydroxylamine-O-sulfonic acid (HOSA), which is already known in the literature as an amine reagent (see, for example, 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 can be carried out in a known manner (see, for example, 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, which discloses the amination of uracils).

The reaction is conveniently carried out in a polar solvent, for example dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide or ethyl acetate, which has hitherto 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 amine reagent is preferably in each case 0.5 times to twice the molar amount with respect to the amount of the starting compound.

Procedure C)

Sulfurization of a 3- (benzazol-4-yl) pyrimidinedione derivative of formula I wherein X is oxygen:

(I) (X = O) (D (X = S))

Sulfurization is generally carried out in an inert solvent or diluent, for example in an aromatic hydrocarbon such as toluene and xylenes, in ether such as diethyl ether, 1,2-dimethoxyethane and tetrahydrofuran, or in an organic amine such as pyridine.

Particularly suitable sulfurizing agents are phosphorus pentasulfide and 2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphethane-2,4-dithione ("Lawesson's reagent").

Typically, one to five molar equivalents of the starting compound to be sulfurized will be sufficient to complete the reaction.

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

Procedure D)

Cyclization of an aryl urea of formula III or an arylanilide of formula IV in the presence of

(I) (X = O)

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

The cyclization is generally carried out in an inert organic solvent or diluent which is aprotic, for example in an aliphatic or cyclic ether such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, in an aromatic such as benzene or toluene, or in a polar solvent such as dimethylformamide or dimethylsulfoxide. Mixtures of a polar solvent and a hydrocarbon such as n-hexane are also suitable. Depending on the starting compound, water may also be suitable as a diluent.

Suitable bases are preferably alkali metal alkoxides, in particular sodium alkoxides, alkali metal hydroxides, in particular sodium hydroxide and potassium hydroxide, alkali metal carbonates, especially sodium carbonate and potassium carbonate, and metal hydrides, especially sodium hydride. When sodium hydride is used as the base, it has proven advantageous to carry out this process in an aliphatic or cyclic ether, in dimethylformamide or in dimethylsulfoxide.

Normally, 0.5 to 2 times the molar amount of the base relative to the amount of IV or V will be sufficient to carry out the reaction.

The reaction temperature is generally 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 process product is obtained as a metal salt, the metal corresponding to the cation of the base. The salt may be isolated and purified in a known manner, or if necessary converted by acid to the free compound I, wherein R ¹ = hydrogen.

Procedure E)

Treatment of substituted 2-aminoaniline with nitric acid

(Va) (|) {= Y- = NN (R ⁶ ) -}

The cyclization reaction can be carried out by known methods (see, for example, Houben-Weyl, Methoden der organischen Chemie, Georg Thieme Verlag Stuttgart, vol. E8d, 1st edition 1994, pp. 409-415).

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 include in particular dilute mineral acids such as 10% hydrochloric acid.

Nitrous acid is preferably prepared in situ by the addition of an alkali metal nitrite - alone or in aqueous solution - to a reaction mixture consisting of diaminobenzene in an acidic aqueous solution or in a carboxylic acid.

A suitable reaction temperature is in particular 0 to 20 ° C, very suitably about 5 ° C.

The starting materials are preferably used in approximately stoichiometric amounts, or the process is carried out with an excess of the theoretically expected amount of nitric acid, which is not more than 10 mole percent.

The following intermediate can be cyclized in a similar manner:

(VII)

Procedure F)

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

an acid derivative

(V) (I) (Z = chemical bond, O,

NH; R ⁷ = H, unsubstituted. or subst. alkyl, alkenyl or aryl

The condensation reaction of bifunctional benzenes V with carbonic acid derivatives or carboxylic acid derivatives is carried out in a known manner (see, for example, Houben-Weyl, Method in Organic Chemistry, Georg Thieme Veriag Stuttgart, Vol. E8c, 1st edition 1994, p. 247-284, Volume E8b, 1st Edition 1994, pp. 881-901; Volume E8a, 1st Edition 1993, pp. 1032-1078). Preferred carbonic acid or carboxylic acid derivatives are the corresponding anhydrides, chlorides, orthoesters, diimides, nitriles, trichloromethyl substituted compounds, isocyanates and thio analogues thereof.

Suitable solvents or diluents are, in particular, organic solvents, for example aromatic hydrocarbons such as benzene, toluene and o-, m-, p-xylene, halogenated hydrocarbons such as dichloromethane, 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 dimethylsulfoxide.

If desired, the reaction can be accelerated by the addition of catalytic amounts of acid. Particularly suitable acids are mineral acids such as hydrochloric acid or sulfonic acids such as p-toluenesulfonic acid. The amounts of acid are preferably 0.1 to 5 mole percent based on the amount of V.

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

The carbonic acid derivative or carboxylic acid derivative is used either in an approximately stoichiometric amount or in excess. If appropriate, a very large excess may be used or the process may be carried out without solvent. Preference is given to approximately stoichiometric amounts or an excess of up to 10 molar equivalents relative to the amount of V.

Substituted 2-aminophenols, -thiophenols and -anilines (V) are preferably obtained by reduction of the corresponding 2-nitrophenols, -thiophenols or -anilines VIII (see, for example,

Houben-Weyl, Methoden der organischen Chemie [Methods in Organic Chemistry],

Georg Thieme Verlag Stuttgart, Vol. X / 1.4. edition 1957, p. 431 et seq.):

Particularly suitable reducing agents are:

elemental metals such as iron, tin and zinc, hydrogen in the presence of suitable catalysts such as palladium or platinum on carbon or Raney nickel, or complex hydrides such as L 1 AlH ₄ and NaBH ₄ , with or without catalysts.

Depending on the reducing agent, suitable solvents are typically carboxylic acids such as acetic or propionic acid, alcohols such as methanol and ethanol, ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran and dioxane, aromatics such as benzene and toluene, and mixtures thereof.

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

The starting compounds are commonly used in approximately stoichiometric amounts; however, an excess of one or the other of up to about 10 mole percent may also be preferred in individual cases.

2-nitrophenols, -thiophenols and -anilines VIII can in turn be released from the corresponding protected nitro compounds IX:

(IX)

Protection = a common protecting group that protects phenols or thiophenols as ethers or an amino group as an amide.

Protecting groups can be eliminated by known methods (see, for example, Greene / Wuts: Protective Groups in Organic Synthesis, John Wiley & Sons, Inc., 2nd edition 1991, pp. 145 et seq. And pp. 279 et seq.).

Suitable elimination agents are in particular:

for alkylphenols: trimethylsilyl iodide, boron tribromide, boron tetrachloride, aluminum chloride, lithium chloride or hydrogen bromide;

for unsubstituted or substituted benzylphenols or thiophenols: boron trifluoride, hydrofluoric acid or hydrogen on the catalyst, preferably precious metal catalysts such as palladium or platinum.

Preferably, the solvent or diluent is chosen to be inert to the respective elimination reagent. When trimethylsilyl iodide, boron tribromide, boron trichloride or aluminum chloride halides are used, halogenated solvents such as dichloromethane, chloroform, carbon tetrachloride and dichloroethane are particularly preferred. Hydrogen bromide is preferably used in aqueous solution, with very particular preference as a 48% solution; lithium chloride is preferably used in polar solvents such as lower alcohols, dimethylsulfoxide and dimethylformamide; the hydrogenolytic methods are preferably carried out in lower alcohols or carboxylic acids alone or with the addition of a hydrogen transfer agent, for example cyclohexene and cyclohexadiene.

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

The elimination agent is preferably used in approximately stoichiometric amounts or in excess. The excess is particularly preferred between one and ten molar equivalents with respect to the amount of IX.

Finally, protected nitro compounds IX can be obtained in a known manner by nitration of (protected) phenols, thiophenols, or anilines X (see, for example, HoubenWeyl, Method in Organic Chemistry), Georg

Thieme Verlag Stuttgart, Vol. 10 / 1.1971, p. 479 et seq.):

Suitable nitrating agents are, in particular, nitric acid as a mixture with sulfuric acid or acetic anhydride, or nitronium salts, in particular nitronium tetrafluoroborate. The mixture of nitric and sulfuric acids may consist of any desired mass. ratios of the two components; mixtures are preferred where sulfuric acid predominates or acts as a solvent. This also applies to a mixture of nitric acid and acetic anhydride. Nitronium tetrafluoroborate is preferably used in aprotic polar solvents, for example acetonitrile or nitromethane.

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

When nitric acid is used as the reagent in nitration reactions, the process is preferably carried out with an approximately equimolar amount or particularly preferably with an excess of the nitrating agent. The excess may be a multiple of the amount of X. Nitrone tetrafluoroborate is preferably used in equimolar amounts relative to the substrate, or in a small excess of between 1.1 and 1.5 molar equivalents.

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

^R4 \ ^R \ O ₂ N— (R5 ΓΊ W I I N-Y N-Y (XI) (XII)

3- (Benzazol-4-yl) pyrimidinedione derivatives of formula I with one or more chiral centers are commonly obtained as enantiomeric or diastereomeric mixtures, which, if necessary, can be resolved to obtain substantially pure isomers by methods commonly used for this purpose, for example by crystallization or chromatography on an optically active adsorbate. Pure optically active isomers may be prepared preferably from the corresponding optically active starting materials.

The 3- (benzazol-4-yl) pyrimidinedione derivatives of formula I wherein R ¹ is hydrogen can be converted to salts in a manner known per se (see in this context, as described in process A)).

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

Procedure G)

Reaction of β-ketocarboxylic ester XIII with urea XIV:

(Cat.)

--- ►

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

The 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 form azeotropic mixtures, for example aromatics such as benzene, toluene and o-, m-, p-xylene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and chlorobenzene, aliphatic and cyclic ethers such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or cyclohexane, but also alcohols such as methanol and ethanol.

Suitable acid 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 ptoluenesulfonic acid, and acidic cation exchangers such as "Amberlyst 15" (Fluka).

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

XIV and the β-ketocarboxylic ester XIII are preferably used in approximately stoichiometric amounts, or the process is performed with a small excess of either component up to about 10 mole percent.

An amount of 0.5 to 2 mole percent catalyst based on the amount of one of the starting compounds will normally suffice.

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

Procedure H)

Reaction of enolether XV with urea XVI:

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

The reaction is preferably carried out in an inert organic solvent which is miscible with water, e.g. an aliphatic or cyclic ether such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or in a lower alcohol, especially ethanol, the reaction temperature being usually from 50 to 100 ° C, preferably the boiling point of the reaction mixture.

However, the reaction may also be carried out in an aromatic diluent such as benzene, toluene and o-, m-, p-xylene, where addition of either an acid catalyst such as hydrochloric acid and p-toluenesulfonic acid or a base such as an alkali metal alkoxide such as sodium methoxide and ethoxide is recommended. solution. In this process variant, the reaction temperature is again normally from 50 to 100 ° C, but preferably 60 to 80 ° C.

As regards the wt. ratios, here also applies what was stated for method G).

Procedure J)

Reaction of enaminoester XVII with isocyanate XVIII:

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

The reaction is preferably carried out in the presence of a substantially anhydrous aprotic organic solvent or diluent, for example an aliphatic or cyclic ether such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, an aliphatic or aromatic hydrocarbon such as n-hexane, benzene, toluene and o-, m-, p -ylene, a halogenated aliphatic hydrocarbon such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene, an aprotic polar solvent such as dimethylformamide, hexamethylphosphotriamide and dimethylsulfoxide, or in a mixture thereof.

If desired, the process can also be carried out in the presence of a metal hydride such as sodium hydride and potassium hydride, or an organic tertiary base such as triethylamine and pyridine, wherein the organic base may simultaneously act as a solvent.

The starting materials are preferably used in stoichiometric amounts, or the process is carried out with a small excess of one or the other component up to about 10 mole percent. If the process is carried out without solvent in the presence of an organic base, it will be present in a larger excess.

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

In a particularly preferred embodiment, the resulting enamine ester III is converted directly (i.e. in situ) by treatment with excess base according to process D) to the corresponding product I.

Procedure K)

Reaction of enaminoester XVII with urethane XIX:

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

This reaction is preferably carried out in an aprotic polar solvent or diluent such as dimethylformamide, 2-butanone, dimethylsulfoxide and acetonitrile, preferably in the presence of a base, for example an alkali metal alkoxide or alkaline earth metal alkoxide, especially sodium alkoxide such as sodium methoxide, alkali metal carbonate; an alkaline earth metal carbonate, especially sodium carbonate, or an alkali metal hydride such as lithium hydride and sodium hydride.

Typically, one or two equivalents of base relative to the amount of XVII or XIX will suffice.

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

As regards the wt. ratios of the starting compounds, here also what was stated for method G).

In a particularly preferred embodiment, the base is sodium alkoxide and the alcohol formed during the reaction is continuously distilled off. The enaminoesters IV obtained can be cyclized according to procedure D) without isolation from the reaction mixture to give the substituted benzothiazoles I salt (where R ¹ = H).

The urethanes XIX can in turn be prepared, for example, from carbonyl chlorides XX and anilines

XXI:

base

To avoid excess aniline, it is generally necessary to add an auxiliary base such as triethylamine, pyridine or alkali metal carbonates to scavenge the hydrogen chloride formed during the reaction. Pyridine is particularly suitable since it can be used simultaneously as a solvent.

Suitable solvents or diluents in addition to pyridine are, in particular, aromatic hydrocarbons such as benzene, toluene and o-, m-, p-xylene, halogenated hydrocarbons such as dichloromethane, 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.

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

The starting materials are preferably used either in approximately stoichiometric amounts, or no more than 10 mole percent of excess carbonyl chloride is selected.

The auxiliary base is commonly used in an approximately equimolar amount with respect to the amount of XX or XXI - or in excess up to about a molar double. When pyridine is used as the auxiliary base, an even higher excess is recommended where the process can be carried out without additional solvent.

Procedure L)

Reaction of isocyanate XXII with aniline derivative XXI:

(XXI)

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

This reaction is preferably carried out in substantially anhydrous aprotic organic solvents or diluents, for example in the presence of an aliphatic or cyclic ether such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, an aliphatic or aromatic hydrocarbon such as n-hexane, benzene, toluene and o. m-, p -ylene, a halogenated aliphatic hydrocarbon such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene, an aprotic polar solvent such as dimethylformamide, hexamethylphosphotriamide and dimethylsulfoxide, or in a mixture thereof.

If desired, the process may be carried out in the presence of a metal hydride such as sodium hydride and potassium hydride, an alkali metal or alkaline earth metal alkoxide such as sodium methoxide, sodium ethoxide and sodium tert-butoxide, or an organic nitrogen base such as triethylamine and pyridine. simultaneously as a solvent.

The starting materials are preferably used in approximately stoichiometric amounts, or one of the components is used in excess of up to about 20 mole percent. If the process is carried out without a solvent in the presence of an organic base, it will preferably be present in an even greater excess.

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

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

(IV) (R1 = Η)

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

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

To prepare enamine carboxylates IV, wherein R ¹ = amino, it is recommended to use a compound XXIV with an amino-protected (e.g. as a hydrazone).

Particularly suitable solvents or diluents are organic liquids which can be mixed with water to form an azeotropic mixture, for example aromatics such as benzene, toluene and o-, m-, p-xylene, or halogenated hydrocarbons such as carbon tetrachloride and chlorobenzene.

Particularly suitable catalysts are 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 Amberlyst 15 (Fluka).

Generally, a reaction temperature of from about 70 to 150 ° C is sufficient; however, in order to rapidly remove the reaction water, the process is preferably carried out at the boiling point of the reaction mixture.

XXIII and XXIV are commonly 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 (Procedure N)):

* ► (XXIII) (R 3 = H

(XXI)

H ₃ C (XXV)

The reaction is preferably carried out in an anhydrous inert aprotic solvent, for example in a halogenated hydrocarbon such as dichloromethane, chloroform, carbon tetrachloride and chlorobenzene, an aromatic hydrocarbon such as benzene, toluene and o-, m-, p-xylene, or an aliphatic or cyclic ether such as diethyl ether, dibutyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane.

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

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

Isocyanates XVIII can be obtained, for example, from aniline derivatives XXI according to procedure O):

(XVIII)

The process can be carried out in an inert, substantially anhydrous solvent or diluent or without solvents, wherein the aniline derivatives XXI are preferably reacted with phosgene, a "phosgene equivalent" such as diphosgene, triphosgene and carbonyldiimidazole, or with trichloromethyl chloroformate.

Particularly suitable solvents or diluents are aprotic organic solvents, for example dimethylformamide or aromatics such as toluene and o-, m-, p-xylene, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene, aliphatic or cyclic ethers such as 1,2 dimethoxyethane, tetrahydrofuran and dioxane, or esters such as ethyl acetate, and mixtures thereof.

The starting materials are preferably 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, for example in 0.5 to 2 molar amounts relative to the amount of XXI.

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

Aniline derivatives XXI, in turn, can be obtained by a known method (see, for example, Houben-Weyl, Methods in Organic Chemistry, Georg Thieme Verlag Stuttgart, Vol. XI / 1, 4th edition 1957, p. 431 et seq.) By reduction. the relevant nitroderivativesXXVI:

R5 reduction

--- ►

As regards reducing agents, solvents, reaction temperatures and wt. ratios, as described above for process F).

Compounds XXVIII and XXI may also contain one or more chiral centers, which are conveniently obtained in the form of enantiomeric or diastereomeric mixtures. If desired, these mixtures can be resolved into substantially pure isomers by methods conventionally used for this purpose, for example by crystallization or by chromatography on an optically active adsorbate. Pure optically active isomers can also be prepared, for example, from the corresponding optically active starting materials.

Unless otherwise stated, all of the processes described above are preferably carried out at atmospheric pressure or under the actual pressure of the reaction mixture. The reactants are generally used in a molar ratio of 0.95: 1 to 5: 1.

The reaction mixtures are generally worked up by known methods, for example by diluting the reaction solution with water and then isolating the product by filtration, crystallization or solvent extraction, or removing the solvent, partitioning the residue in a mixture of water and a suitable organic solvent and treating the organic phase to give the product.

The compounds I and their agriculturally useful salts are suitable both as herbicides in the form of isomer mixtures and in the form of pure isomers. The herbicidal compositions containing the compounds of formula I show very good vegetation control on non-cultivated areas, especially at high application rates. For crops such as wheat, rice, maize, soybeans and cotton, they act against broadleaf weeds and grass weeds without significantly damaging crop plants. This effect is especially observed at low application rates.

Depending on the application method used, the compounds of formula (I) or compositions containing them can additionally be used in several other crop plants to remove unwanted plants. Examples of suitable crop plants are:

Allium cepa, Pineapple comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. Silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica); arboreum (Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiiiensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Medus spec. Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum cerin , Solanum tuberosum, Sorghum bicolor (s. Vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vitia faba, Vitis vinifera and Zea mays.

In addition, the compounds I can also be used in crops which have been rendered tolerant to the action of herbicides by breeding, including genetic engineering methods.

The compounds of the formula I or herbicidal compositions containing them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, as well as highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, powders, coating materials or granules. spraying, atomizing, dusting, coating or watering. The forms of use depend on the intended purposes; in any case, they should guarantee the finest possible distribution of the active ingredients according to the invention.

Suitable inert excipients include, but are not limited to: medium to high boiling mineral oil fractions, for example, kerosene and naphtha, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffin, tetrahydronaphthalene, alkylated naphthalenes and derivatives thereof, alkylated benzenes and derivatives thereof, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, e.g. amines such as N-methylpyrrolidone and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders, or water dispersible granules by the addition of water. In the preparation of emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, an adhesive, a dispersing agent or an emulsifier. However, it is also possible to prepare concentrates composed of the active substance, wetting agent, adhesive, dispersing agent or emulsifier and, if necessary, solvent or oil, and these concentrates are suitable for dilution with water.

Suitable surfactants are alkali metal, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e.g. Ligno-, phenol-, naphthalene-, and dibutylnaphthalenesulfonic acid, and fatty acids, alkyl- and alkylaryl sulfonates, alkyl sulfates, lauryl ether sulfates and sulfates of fatty alcohols, and salts of sulfated hexa-, hepta- and octadecanols, and glycol ethers of fatty alcohols, condensate and its derivatives with formaldehyde, condensates of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl and tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohols, isotridecyl alcohol oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste sludge or methylcellulose.

Powders, sieving materials and dusts can be prepared by mixing or binding the active ingredients to a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneous granules may be prepared by binding the active ingredients to solid carriers. Solid carriers are mineral clays such as silica, silica, silicates, talc, kaolin, limestone, lime, chalk, clay, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as sulfate ammonium, ammonium phosphate, ammonium nitrate, ureas and products of vegetable origin, such as cereal flour, tree bark meal, wood and nut shell meals, cellulose powders and other solid carriers.

The concentration of the active compounds of the formula I in the finished preparations can be varied within wide ranges. In general, the formulations comprise about 0.001 to 98% by weight, preferably 0.01 to 95% by weight. at least one active ingredient. The active ingredients are used in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

DETAILED DESCRIPTION OF THE INVENTION

The following formulations illustrate the preparation of such products:

I. 20 wt. parts of compound no. 1 is dissolved in a mixture consisting of 80 wt. parts by weight of alkylated benzene, 10 wt. 5 parts by weight of an adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid N-monoethanolamide; parts by weight of calcium dodecylbenzenesulfonate and 5 wt. parts of an adduct of 40 moles of ethylene oxide and 1 mole of beaver oil. Pouring the solution into 100,000 wt.

parts by weight of water and thoroughly mixing to obtain an aqueous dispersion containing 0.02 wt. active ingredient.

II. 20 wt. parts of compound no. 2 is dissolved in a mixture consisting of 40 wt. parts by weight of cyclohexanone, 30 wt. parts by weight of isobutanol, 20 wt. parts by weight of an adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol and 10 wt. parts of an adduct of 40 moles of ethylene oxide and 1 mole of beaver oil. Pouring the solution into 100,000 wt. parts by weight of water and thoroughly mixing to obtain an aqueous dispersion containing 0.02 wt. active ingredient.

III. 20 wt. parts of the active ingredient no. 4 is dissolved in a mixture consisting of 25 wt. parts by weight of cyclohexanone, 65 wt. parts by weight of a mineral oil fraction having a boiling point of 210 to 280 ° C and 10 wt. parts of an adduct of 40 moles of ethylene oxide and 1 mole of beaver oil. Pouring the solution into 100,000 wt. parts by weight of water and thoroughly mixing to obtain an aqueous dispersion containing 0.02 wt. active ingredient.

IV. 20 wt. parts of the active ingredient no. 6 is thoroughly mixed with 3 wt. parts by weight of sodium diisobutylnaphthalene-α-sulfonate, 17 wt. parts by weight of lignosulfonic acid from the sulphated waste sludge and 60 wt. The mixture was ground in a hammer mill. By thoroughly mixing the mixture in 20,000 wt. parts of water to obtain a spray composition comprising 0.1 wt. active ingredient.

3 wt. parts of the active ingredient no. 8 are mixed with 97 wt. parts of finely ground kaolin. In this way, a dust is obtained which contains 3 wt. active ingredient.

VI. 20 wt. parts of the active ingredient no. 12 is thoroughly mixed with 2 wt. parts by weight of calcium dodecylbenzenesulfonate, 8 wt. parts by weight of polyglycol ether of fatty alcohol, 2 wt. parts by weight of sodium condensate of phenol, urea and formaldehyde and 68 wt. parts of paraffin mineral oil. A stable oil dispersion is thus obtained.

VII. 1 wt. part of compound no. 14 is dissolved in a mixture consisting of 70 wt. parts by weight of cyclohexanone, 20 wt. parts by weight of ethoxylated isooctylphenol and 10 wt. parts of ethoxylated beaver oil. The mixture can then be diluted with water to obtain the desired concentration of the active ingredient. A stable emulsion concentrate is thus obtained.

VIII. 1 wt. part of compound no. 19 is dissolved in a mixture consisting of 80 wt. parts by weight of cyclohexanone and 20 wt. parts of Wettol® EM 31 (= nonionic emulsifier based on ethoxylated beaver oil; BASF AG). The mixture can then be diluted with water to obtain the desired concentration of active ingredient. A stable emulsion concentrate is thus obtained.

The active ingredients I or the herbicidal compositions can be applied before or after emergence. If some crop plants are less tolerant of the active ingredients, application techniques may be used in which the herbicidal compositions are sprayed using a spraying device in such a way that they come in as little contact as possible or do not come into contact with leaves of susceptible crop plants. below them, or with uncovered soil (additional application, lay-by).

Depending on the intended purpose, the season, the target plants and the growth stage, the rate of application of the active ingredient is 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active ingredient (OJ).

In order to broaden the spectrum of action and to achieve synergistic effects, the 3- (benzazol-4-yl) pyrimidinedione derivatives I may be mixed and applied together with a large number of representatives of other groups of herbicidal or growth-regulatory active ingredients. Suitable components in the mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy / heteroaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2- (hetaroyl / aroyl) -1,3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF ₃ -phenyl derivatives, carbamates, quinolinecarboxylic acid and derivatives thereof, chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, cyanides pyridine carboxylic seline and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.

In addition, it may be advantageous to apply the compounds of the formula I alone or in combination with other herbicides also in the form of a mixture with other other plant protection agents, for example pest control agents, phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions which are used to treat the lack of nutritional and trace elements. Non-phytotoxic oils and oil concentrates may also be added.

Synthesis examples:

Example 1

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

0.12 g of methyl iodide was added dropwise at 20 ° C to a mixture of 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 absolute dimethylformamide. The reaction mixture was then stirred for an additional 18 hours and 50 mL of water was added. Then the mixture was extracted three times with 20 ml of ethyl acetate each. The combined organic phases were washed with water, dried over sodium sulfate and concentrated. The crude product was purified by silica gel chromatography (eluent: cyclohexane / ethyl acetate = 1: 1). Yield: 0.07 g;

¹ H NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 7.45 (d, 1H), 6.45 (s, 1H), 4.55 (s, 3H),

3.60 (s, 3H).

Example 2

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

0.43 g of ethyl 3-amino-4,4,4-trifluorobut-2-enoate in 3 ml of dimethylformamide was added at 0 ° C over 15 minutes under a nitrogen atmosphere to 0.13 g of sodium methoxide in 7 ml of absolute dimethylformamide. The mixture was stirred for one and a half hours at 10 ° C, after which a solution of 0.57 g ethyl was added dropwise to the reaction mixture.

Of 7-chloro-5-fluoro-1-methyl-1H-benzotriazol-4-ylcarbamate in 20 mL of dimethylformamide over 15 minutes. The mixture was then warmed to 20 ° C and stirring was continued for 5 minutes. The mixture was heated to 60 ° C and 0.35 g of 1,8-diazabicyclo [5.4.0] undec-7ene (DBU) was added. Stirring was continued for 4 hours at 120 ° C and 18 hours at 20 ° C.

The mixture was worked up by pouring into 100 ml of 10% w / v aqueous potassium carbonate. The target product was extracted with diethyl ether (2 x 50 ml) and after adjusting the pH of the aqueous phase to 1 with hydrochloric acid, extracted with ethyl acetate (3 x 30 ml).

The combined organic phases were then washed with approximately 20 ml of saturated aqueous sodium chloride solution and 30 ml of 10% w / w aqueous lithium chloride solution, after which they were dried over sodium sulfate and concentrated. Yield: 0.25 g;

¹ H NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 10.25 (br, 1H), 7.45 (d, 1H), 6.30 (s, 1H), 4.60 (s, 3H).

Step 2.1

2-Chloro-4-fluoro-N-trifluoroacetylaniline

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

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

Step 2.2

3-Chloro-5-fluoro-2-N-trifluóracetylaminonitrobenzén

375 ml of 98% nitric acid was slowly added dropwise at -5 ° C to 75 g of 2-chloro-4-fluoro-N-trifluoroacetylaniline in 753 ml of acetic anhydride. The mixture was then stirred at -5 ° C for 1 hour, then warmed to 20 ° C. The progress of the reaction was monitored by HPLC (RP ¹⁾ -18 (eluent: acetonitrile / water = 7: 3). When it was no longer possible to detect the starting material, the reaction mixture was poured into ice saturated aqueous sodium chloride solution. The solid target product was then collected, washed with water and dried for several hours in a drying oven under reduced pressure at 20 ° C. Yield: 62.3 g;

¹ H NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 8.50 (br, 1H), 7.80 (dd, 1H), 7.60 (dd, 1H). Step 2.3

3-Chloro-5-fluoro-2- (N-methyl-N-trifluoro-acetylamino) 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 absolute dimethylformamide. The reaction mixture was then stirred at 20 ° C for 18 hours, after which 500 mL of water was added. Then the mixture was extracted three times with 100 ml of ethyl acetate each. The combined organic extracts were dried over sodium sulfate and concentrated. Yield: 16.3 g;

¹ H NMR (270 MHz, in CDCl 3): δ [ppm] = 7.80 (m, 1H), 7.60 (m, 1H), 3.40 (s, 3H). Step 2.4

3-Chloro-5-fluoro-2-metylaminonitrobenzén

173 ml of 1 N sodium hydroxide solution was added to a solution of 16.3 g of 3-chloro-5-fluoro-2- (N-methyl-N-trifluoroacetylamino) nitrobenzene in 173 ml of ethanol. The reaction mixture was then stirred for 1 hour, after which it was diluted with 500 ml of water. Then, ¹ ) the reverse phase was extracted, on silica gel three times with 80 ml of ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate and concentrated. Yield: 10.1 g;

¹ H NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 7.70 (dd, 1H), 7.35 (dd, 1H), 6.70-6.50 (br, 1H), 3.10 (d, 3H).

Step 2.5

2-Amino-6-chloro-4-fluoro-N-methylaniline

55.94 g of stannous chloride 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 so that the temperature of the mixture did not exceed 60 ° C. The mixture was worked up by pouring into 1 L of ice-water, after which the pH was adjusted to 14 with sodium hydroxide solution. Then the mixture was extracted three times with 100 ml of tert-butyl methyl ether each. The combined organic phases were washed with water, dried over sodium sulfate and concentrated. Yield: 7.5 g;

¹ H NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 6.50 (dd, 1H), 6.35 (dd, 1H), 3.90-3.60 (br, 3H), 2.65 (s, 3H).

Step 2.6

7-Chloro-5-fluoro-1-methylbenzotriazole

A solution of 3.25 g of 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% hydrochloric acid. After stirring at 5 ° C for one hour, the reaction mixture was diluted by adding 200 mL of water. The solid phase was then separated, washed with 3 x 50 ml of water and dried in a vacuum oven at 20 ° C. Yield: 7.2 g;

¹ H NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 7.60 (dd, 1H), 7.30 (dd, 1H), 4.55 (s, 3H). Step 2.7

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

0.65 mL of 98% nitric acid was slowly added dropwise at -20 ° C to

1.5 g of 7-chloro-5-fluoro-1-methylbenzotriazole in 28 ml of concentrated sulfuric acid.

The mixture was then stirred at 0 ° C for 1 hour, after which it was heated to 20 ° C. Stirring was continued for 18 hours and the reaction mixture was then poured into 500 ml of ice-water. The solid phase was separated, washed with water and dried in a vacuum oven at 20 ° C. Yield: 1.66 g;

¹ H NMR (270 MHz, in _CDCl3): δ [ppm] = 7.50 (d, 1H), 4.65 (s, 3H).

Step 2.8

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

1.66 g of 7-chloro-5-fluoro-1-methyl-4-nitrobenzotriazole was reduced with stannous chloride / sodium borate in a manner similar to that described in step 2.5. Yield: 1.27 g;

¹ H NMR (250 MHz, v (CD ₃ ) ₂ SO): δ [ppm] = 7.45 (d, 1H), 6.25 (br, 2H), 4.45 (s, 3H), 4 30 (q, 2H); 1.35 (t, 3H).

Step 2.9

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

2.28 g of ethyl chloroformate was added slowly dropwise to 13 ml of absolute pyridine at 0 ° C, after which 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. The mixture was stirred for 30 minutes at 0 C C when it was warmed to 20 a C and then stirred for 18 hours. The reaction mixture was finally poured into 100 mL of 10% hydrochloric acid. The mixture was then extracted three times with 50 ml of tert-butyl methyl ether each time. The combined organic phases were washed with 100 ml of water and concentrated.

To the residue was added 50 mL of diethyl ether. The undissolved component was separated and washed with 3x30 ml diethyl ether. The combined ether phases were concentrated. Yield: 0.37 g;

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

Example 3

3- [7-Chloro-5-fluoro-1-methyl-2-trifluoromethyl-1H-benzimidazol-4-yl] -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (compound 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 to Example 1. The crude product was purified by silica gel chromatography (eluent: cyclohexane / ethyl acetate = 2: 1). Yield: 1.4 g;

¹ H NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 7.35 (d, 1H), 6.40 (s, 1H), 4.30 (s, 3H),

3.55 (s, 3H).

Example 4

3- [7-Chloro-5-fluoro-1-methyl-2-trifluoromethyl-1H-benzimidazol-4-yl] -1-amino-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (compound 6 )

0.25 g of 2,4-dinitro-O-aminophenol was added to a mixture of 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. After stirring at 20 ° C for 18 h, the mixture was diluted by adding 50 mL of ethyl acetate. The resulting mixture was washed with 3 x 30 mL water, dried over sodium sulfate, and concentrated. The crude product was purified by medium pressure liquid chromatography (MPLC; eluent: cyclohexane / ethyl acetate = 2: 1). Yield: 0.4 g;

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

Example 5

3- [7-Chloro-5-fluoro-1-methyl-2-trifluoromethyl-1H-benzimidazol-4-yl] -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (compound 4)

4.31 g of ethyl 3-amino-4,4,4-trifluorobut-2-enoate in 20 ml of dimethylformamide was added dropwise at 0-5 ° C to 0.82 g of sodium hydride in 50 ml of absolute dimethylformamide. The mixture was then stirred for one hour at the same temperature, after which 7-chloro-5-fluoro-4-isocyanato-1-methyl-2-trifluoromethylbenzimidazole (from step 5.4) in ml of dimethylformamide was added at -30 ° C. Stirring was continued for one hour at -30 ° C and for another hour at 20 ° C.

The reaction mixture was worked up by careful pouring into 200 ml of ice-water. Acidification with 10% hydrochloric acid gave a solid which was filtered off, washed with water and dried in a vacuum oven at 20 ° C. Purification by flash chromatography (eluent: cyclohexane / ethyl acetate = 2: 1) gave 5.08 g of the target product.

After separation of the solid, the target product still remaining in the filtrate (2.46 g) was isolated by extracting the filtrate three times with 200 ml of tert-butyl methyl ether, washing the combined ether phases, drying them over sodium sulfate and concentrating.

Total yield: 7.54 g;

¹ H NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 7.40 (d, 1H), 6.30 (s, 1H), 4.30 (s, 3H).

Step 5.1

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

15.5 g of 3-chloro-5-fluoro-2- (N-methyl-N-trifluoroacetylamino) nitrobenzene (step 2.3) was reduced with stannous chloride / sodium borate without isolation of the intermediate in a manner similar to step 2.5 to give the corresponding amino compound , which then spontaneously cyclized to eliminate water to obtain the target product. Yield: 9.32 g;

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

Step 5.2

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

46.3 mL of 98% nitric acid was slowly added dropwise at 0 ° C to

9.65 g of 7-chloro-5-fluoro-1-methyl-2-trifluoromethyl-benzimidazole in 96.5 ml of acetic anhydride.

After stirring at 0 ° C for one hour, the mixture was carefully warmed to 20 ° C. (In case an exothermic reaction started, the temperature was kept below 25 ° C with an ice bath.) The reaction mixture was then stirred for another two hours at 20 ° C and then poured into an ice saturated aqueous sodium chloride solution. The resulting solid phase was separated, washed with water and dried in a vacuum oven at 20 ° C.

Yield: 8.5 g;

¹ H NMR (400 MHz, in _CDCl3): δ [ppm] = 7.40 (d, 1H), 4.35 (s, 3H).

Step 5.3

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

8.71 g of 7-chloro-5-fluoro-1-methyl-4-nitro-2-trifluoromethylbenzimidazole was reduced with stannous chloride / sodium borate in a manner similar to that described in step 2.5. Yield: 6.3 g;

¹ H NMR (270 MHz, in _CDCl3): δ [ppm] = 7.05 (d, 1H), 4.45 (br, 2H), 4.20 (s, 3H). Step 5.4

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

23.32 g of diphosgene were added to 6.3 g of 4-amino-7-chloro-5-fluoro-1-methyl-2-trifluoromethylbenzimidazole in 100 ml of absolute toluene. The mixture was then refluxed for 6 hours. After stirring an additional 18 hours at 20 ° C, the reaction mixture was 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) -pyrimidinedione (Compound 8)

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

¹ H NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 7.10 (d, 1H), 6.40 (s, 1H), 4.00 (s, 3H),

3.55 (s, 3H); 2.55 (s, 3H).

Example 7

3- [7-Chloro-1,2-dimethyl-5-fluoro-1H-benzimidazol-4-yl] -6-trifluoromethyl-2,4 (1H, 3H) pyrimidinedione (compound 7)

The 7-chloro-1,2-dimethyl-5-fluoro-4-isocyanatobenzimidazole from step 7.4 was reacted with ethyl 3-amino-4,4,4-trifluorobut-2-enoate in a manner similar to Example 5. The crude product Purified by medium pressure liquid chromatography (eluent: ethyl acetate / methanol = 15: 1). Yield: 0.7 g;

¹ H NMR (270 MHz, in CDCl ₃ ): δ [ppm] = 7.15 (d, 1H), 6.20 (s, 1H), 4.05 (s, 3H),

2.55 (s, 3H).

Step 7.1

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

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

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

Step 7.2

7-Chloro-1,2-dimethyl-5-fluoro-4-nitrobenzimidazole% nitric acid was added dropwise at -5 to at most 0 ° C to 7.92 g of 7-chloro-1,2-dimethyl-5-fluorobenzimidazole in 139 ml of concentrated sulfuric acid, during which time the progress of the reaction was monitored by high performance liquid chromatography (HPLC) on an RP-18 column (eluent: acetonitrile / water = 1: 1). When the starting material was no longer detectable, the reaction mixture was poured into ice-water, after which the pH was adjusted to 14 with sodium hydroxide solution. The solid phase was separated, washed with water and dried in a vacuum oven at 20 ° C. The two regioisomeric nitro compounds that formed were separated by flash chromatography on silica gel (eluent: ethyl acetate; the product that eluted first was the desired regioisomer). Yield: 5.6 g;

¹ H NMR (400 MHz, in _CDCl3): δ [ppm] = 7.05 (d, 1H), 4.10 (s, 3H), 2.65 (s, 3H). Step 7.3

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

5.6 g of 7-chloro-1,2-dimethyl-5-fluoro-4-nitrobenzimidazole were reduced with stannous chloride / sodium borate in a manner similar to that described in step 2.5. The crude product obtained was used directly without purification in step 7.4. Yield: 4.1 g.

Step 7.4

7-Chloro-1,2-dimethyl-5-fluoro-4-izokyanatobenzimidazol

4.1 g of 4-amino-7-chloro-1,2-dimethyl-5-fluorobenzimidazole was reacted with the diphosgene in a similar manner as in step 5.4. The crude product obtained was reacted directly without purification 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 dichloromethylenimmonium chloride were added. 100 ml

1,2-dichloroethane, after which the mixture was poured into a glass pressure vessel holder and heated at 120 ° C in a sealed pressure vessel for 5 hours. During this process, the vessel's self-pressure has risen to approximately 5 bar. The vessel was then cooled. The clear product solution was washed with dilute aqueous potassium carbonate solution.

The organic phase was dried over sodium sulfate and concentrated.

The crude product was purified by flash chromatography using a short column (eluent:

cyclohexane / tert-butyl methyl ether = 8: 2). Yield: 0.5 g;

^{@ 1} H NMR (270 DEG, in CDCl3): .delta. [Ppm] = 6.85 (d, 1H), 6.4 (s, 1H), 3.6 (s, 3H),

3.25 (s, 6H).

Step 8.1

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

A nitration mixture consisting of 20.4 ml of concentrated sulfuric acid and 25.5 ml of 98% nitric acid was slowly added dropwise with cooling to -20 ° C to 51.0 g of 3- [4-chloro-6-fluoro-3- methoxyphenyl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione in 1 L of concentrated sulfuric acid. When addition was complete, stirring was continued for 30 minutes at -20 ° C. The reaction mixture was then stirred into 1 L of ice-water. The resulting solid phase was separated, washed with water and dried in a vacuum oven at 20 ° C. Yield: 57.0 g;

¹ H NMR (270 MHz, in CDCl 3): δ [ppm] = 7.55 (d, 1H), 6.35 (s, 1H), 4.05 (s, 3H),

3.55 (s, 3H).

Step 8.2

3- [4-chloro-6-fluoro-3-hydroxy-2-nitro-phenyl] -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) pyrimidinedione

19.0 g of lithium chloride was added to 57.0 g of 3- [4-chloro-6-fluoro-3-methoxy-2-nitrophenyl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione in about 500 mL of absolute dimethylformamide. 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 target product was extracted with 3 x 200 mL tert-butyl methyl ether. The ether phase was washed repeatedly with water and then dried and concentrated. Yield: 46.1 g;

¹ H NMR (250 MHz, VCDC _3): δ [ppm] = 7.65 (d, 1H), 6.35 (s, 1H), 3.60 (s, 3H). Step 8.3

3- [2-Amino-4-chloro-6-fluoro-3-hydroxyphenyl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H) pyrimidinedione g powder was added in small portions at 65 ° C up to 46,0 g 3- [4-chloro-

6-Fluoro-3-hydroxy-2-nitrophenyl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione in

423 ml of water and 36.8 ml of concentrated hydrochloric acid. The mixture was then refluxed for 3 hours. After cooling, the mixture was shaken with 500 mL of ethyl acetate. The organic phase was freed of residual inorganic substances by filtration through Celite® (Manville Corporation). The filtrate was dried over sodium sulfate and concentrated. yield:

37.5 g;

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

Example 9

3- [7-Chloro-5-fluorobenzoxazol-4-yl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione (Compound 12)

0.5 g of trimethyl orthoformate was added to a solution of 0.5 g of 3- [2-amino-4-chloro-6-fluoro-3-hydroxyphenyl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H) - of pyrimidinedione (from step 8.3) in 30 mL of absolute methanol. The mixture was then refluxed for 20 hours. The solvent with excess orthoester was then removed under reduced pressure. The residue was dissolved in ethyl acetate. The organic phase was washed with water, dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography (eluent: cyclohexane / tert-butyl methyl ether = 3: 1). Yield: 0.26 g;

¹ H NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 8.20 (s, 1H), 7.40 (d, 1H), 6.40 (s, 1H),

3.60 (s, 3H).

Example 10

3- [7-Chloro-5-fluoro-2-methoxybenzoxazol-4-yl] -1-methyl-6-trifluoromethyl-2,4- (1H, 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 manner similar to Example 9. Yield: 0.7 g;

¹ H NMR (250 MHz, in CDCl ₃ ): δ [ppm] = 7.10 (d, 1H), 6.40 (s, 1H), 4.20 (s, 3H),

3.60 (s, 3H).

In addition to the 3- (benzazol-4-yl) pyrimidinedione derivatives of the formula I described above, the following Table 2 lists the following which have been prepared or can be prepared in a similar manner:

r * Table 2

ABOUT

2-i αΓo

M

LL O

m LL O

CO LL O αΓ o

uo h-

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Examples of use

The herbicidal action of 3- (benzazol-4-yl) pyrimidinedione derivatives I was demonstrated in the following greenhouse experiments:

The culture vessels were plastic pots containing clay sand with approximately 3.0% humus as substrate. The seeds of the experimental plants were sown separately for each species.

In the pre-emergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing using finely atomizing nozzles. The containers were lightly irrigated to promote germination and growth, and then covered with translucent plastic covers until the plants were rooted. This cover provided uniform germination of the experimental plants, unless germination was adversely affected by the active ingredients.

In the post-emergence treatment, the experimental plants were first grown to a height of 3 to 15 cm, depending on the structure of the plant, and then treated with the active ingredients suspended or emulsified in water. Therefore, the test plants were either sown directly and grown in the same pots, or grown separately as seedlings and transplanted to the experimental pots a few days before treatment. The post-emergence treatment rate was 15.6 or 7.8 g / ha. from. (active ingredient).

Depending on the species, the plants were kept at 10-25 ° C or 20-35 ° C. The experiment lasted 2 to 4 weeks. During this time, the plants were harvested and their response to individual treatments evaluated.

Evaluation was carried out on a scale of 0 to 100. 100 means no plant emergence or complete destruction of at least the aerial parts and 0 means no damage or normal growth.

Plants used in greenhouse experiments belonged to the following species:

Amaranthus retroflexus

Chenopodium album

Gallium aparine

Solanum nigrum

Veronica species

At application rates of 15.6 and 7.8 g / ha. from. upon emergence, compound no. 18 very good herbicidal activity against the above weeds.

Claims (9)

PATENT CLAIMS A 3- (benzazol-4-yl) pyrimidinedione derivative of formula I wherein the variables have the following meanings: X is oxygen or sulfur; R ¹ is hydrogen, amino, C ₁ -C ₆ -alkyl or C 1 -C ₆ -haloalkyl; R ² is hydrogen, halogen, -C ₆ alkyl, C6-haloalkyl, C ₁ -C ₆ alkylthio, -C ₆ alkylsulfinyl or _C-C6 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 = 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, Ο ₃ -β-alkynyl, C 1 -C 6 -alkylsulfonyl, (C ₁ -C ₆ -alkyl) carbonyl, (C 1 -C ₆ -alkyl) ₆ -haloalkyl) carbonyl, (C6-alkyl) thiocarbonyl, (C6-alkoxy) carbonyl, (C6-alkoxy) thiocarbonyl or _C-C6 alkyl, optionally substituted with cyano, -C ₆ -alkoxy, C ₆ -C -alkylthio, (C ₁ -C ₆ -alkoxy) carbonyl, (C 1 -C ₆ -alkylamino) carbonyl, di (C 1 -C 6 -alkyl) aminocarbonyl or (C ₁ -C ₆ -alkyl) carbonyloxy; Z is a chemical bond, oxygen, sulfur, -S (O) -, -S (O) 2 -, -NH- or -N (R ⁸ ) -; R ⁷ and R ⁸ are independently of each other Dripped alkyl, -C ₆ -haloalkyl, hydroxy-C _r C ₄ -alkyl, cyano-C-C ₄ -alkyl, C _r C ₄ alkoxy-C ₄ alkyl, C ₄ -C ₄ -haloalkoxy-- alkyl, C ₃ -C ₄ -alkenyloxy-C ₁ -C ₄ alkyl, C ₃ -C ₄ -alkyloxy-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 -alkyl 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 _{C4alkenyltio-4} alkyl, C 3 -C ₄ -alkynyltio-C ₁ -C ₄ -alkyl _l C _r C _{4 alkylsulfinyl-Ci-4} alkyl, _{Ci-C4-haloalkylsulfinyl-Ci-C4-alkyl,} C 3 -C ₄ -alkenylsulfinyl--C ₄ alkyl, C ₃ -C ₄ -alkynylsulfinyl-C ₄ alkyl, C _{4 alkylsulfonyl-Ci-C4-alkyl,} Cr C ₄ -haloalkylsulfonyl-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 ₆ -alkoxy) -C ₄ -alkylthio) carbonyl-C 1 -C ₄ alkyl, _{aminocarbonyl-Ci-C4-alkyl, (Ci-C4} alkylamino) _{-carbonyl-Ci-C4-alkyl,} di _(Ci-C4 alkyl) _{aminocarbonyl-Ci-C4-alkyl,} di _(Ci-C4 alkyl) phosphonyl-C -C ₄ -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C ₄ -alkyl, phenyl, phenyl-C 1 -C ₄ -alkyl, 3-7 membered heterocyclyl or heterocyclyl-C ₁ -C ₄ -alkyl, wherein each heterocyclyl ring may contain a carbonyl or a thiocarbonyl within the ring, and wherein each cycloalkyl, phenyl and heterocyclyl may be unsubstituted or carry one to four substituents in each case selected from the group consisting of: cyano, nitro, amino, hydroxyl, carboxyl, halogen, CrC ₄ alkyl, -C ₄ -haloalkyl, -C ₄ -alkoxy, C _r C ₄ -haloalkoxy, -C ₄ alkylthio, -C -haloalkyltio _4, C ₄ alkylsulfonyl, -C ₄ haloalkylsulfonyl, _(Ci-C4 alkoxy) carbonyl, ( -C ₄ -alkyl) carbonyl, _(Ci-C4 haloalkyl) carbonyl, _(Ci-C4 alkyl) carbonyloxy, _(Ci-C4 haloalkyl) carbonyloxy and di (Ci-C ₄ alkyl) amino, or when Z is a chemical bond, R ⁷ can also be hydrogen, hydroxyl, 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 are together 1,3-propylene, tetramethylene, pentamethylene or etylénoxyetylén, which may in each case be unsubstituted or may carry one to four C _r C ₄ alkyl or one or two _(Ci-C4 alkoxy) carbonyl; or an agriculturally useful salt of Compound I. A 3- (benzazol-4-yl) pyrimidinedione derivative of formula I according to claim 1, characterized in that: X is oxygen, R ¹ is hydrogen, amino or C 1 -C 6 -alkyl, R ² is hydrogen, halogen, alkyl dripped, -C ₆ -haloalkyl or _C-C6 alkylsulfonyl, R ³ is hydrogen, R ⁴ is hydrogen, fluoro or chloro, 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. Use of a 3- (benzazol-4-yl) pyrimidinedione derivative I or an agriculturally useful salt thereof according to claim 1 as a herbicide. A herbicidal composition comprising a herbicidally effective amount of at least one 3- (benzazol-4-yl) pyrimidinedione derivative of the formula I or a salt I according to claim 1 and at least one liquid and / or solid carrier and, if necessary, at least one surface. active substance. Process for the preparation of herbicidally active compositions, characterized in that it comprises mixing a herbicidally effective amount of at least one 3 (benzazol-4-yl) pyrimidinedione derivative of the formula I or a salt I according to claim 1 and at least one liquid and / or solid carrier; if desired, at least one surfactant. 6. A method of controlling undesirable vegetation which comprises allowing a herbicidally effective amount of at least one 3 (benzazol-4-yl) pyrimidinedione derivative of formula I or a salt I according to claim 1 to act on plants, their environment or seeds. An aryl urea of formula III (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. 8. arylanilides IV (IV), wherein L ² is C _r C ₄ alkyl or phenyl, and R ¹ - R ⁵ and Y are as according to of 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.