RU2001101986A

RU2001101986A - Herbicide and Protector Combinations

Info

Publication number: RU2001101986A
Application number: RU2001101986/04A
Authority: RU
Inventors: Франк Цимер; Лотар Вилльмс; Херманн Бирингер; Эрвин ХАККЕР
Original assignee: Авентис Кропсайенс Гмбх
Priority date: 1998-06-23
Filing date: 1999-06-09
Publication date: 2003-05-27

Claims

1. Herbicidal active agent containing a mixture

A. a herbicidally effective amount of one or more compounds of formula (I)

where V means the remainder of the group (V1) - (V4);

and the symbols and indices have the following meanings:

R is hydrogen, (C ₁ -C ₄ ) alkoxycarbonyl, (C ₁ -C ₄ ) haloalkoxycarbonyl, COOH, cyano;

R ¹ means hydrogen or a residue containing 1-7 carbon atoms, such as (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) -alkynyl, (C ₃ -C ₇ ) -cycloalkyl, (C ₃ -C ₇ ) -cycloalkenyl, (C ₁ -C ₄ ) -alkyl- (C ₃ -C ₇ ) -cycloalkyl, (C ₃ -C ₇ ) -halogenocycloalkyl, (C ₁ -C ₄ ) -alkylthiocycloalkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₂ -C ₄ ) -haloalkenyl;

R ² means hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxyl, (C ₁ -C ₄ ) -haloalkyl, halogen, (C ₁ -C ₄ ) -haloalkoxy, cyano, nitro ;

R ³ means hydrogen or a residue containing 1-4 carbon atoms, such as (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkylcarbonyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -haloalkylsulfonyl, arylsulfonyl, arylcarbonyl- (C ₁ -C ₄ ) -alkyl, aryl- (C ₁ -C ₄ ) -alkyl;

R ⁴ means hydrogen or a residue containing 1-7 carbon atoms, such as (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) -alkynyl, (C ₁ -C ₄ ) -haloalkyl, phenyl, benzyl;

R ⁵ means a residue containing 1-12 carbon atoms, such as (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) - alkyl

(C ₁ -C ₄ ) dialkoxy- (C ₁ -C ₄ ) alkyl, (C ₁ -C ₄ ) alkylthio group, halogen, substituted or unsubstituted aryl, tetrahydropyran-4-yl, tetrahydropyran-3-yl, tetrahydrothiopyran -3-yl, 1-methylthio-cyclopropyl, 2-ethylthiopropyl;

R ⁶ represents hydroxy or 1-4 carbon atom containing radical such as (C ₁ -C ₄₎ -alkoxy, (C ₁ -C ₄₎ -galogenalkoksil, formyloxy, (C ₁ -C ₄₎ -alkilkarboniloksigruppa, (C ₁ - C ₄ ) alkyl sulfonyloxy group, (C ₁ -C ₄ ) alkylthio group, (C ₁ -C ₄ ) haloalkylthio group, (C ₁ -C ₄ ) alkylsulfinyl, (C ₁ -C ₄ ) alkylsulfonyl;

R ⁷ means a residue containing 1-7 carbon atoms, such as (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₃ -C ₇ ) -cycloalkyl, (C ₁ -C ₄ ) - alkyl- (C ₃ -C ₇ ) -cycloalkyl, (C ₃ -C ₇ ) -halogenocycloalkyl;

R ⁸ means a cyano group or a residue containing 1-4 carbon atoms, such as (C ₁ -C ₄ ) -alkoxycarbonyl, (C ₁ -C ₄ ) -alkylcarbonyl, (C ₁ -C ₄ ) -alkyl-sulfonyl, (C ₁ - C ₄ ) alkylsulfinyl, (C ₁ -C ₄ ) alkylthio group, (C ₁ -C ₄ ) alkylaminocarbonyl, (C ₁ -C ₄ ) dialkyl aminocarbonyl;

m is an integer from 0 to 6;

and

Z means the remainder of the group (Zl) - (Z4):

and the symbols and indices have the following meanings:

R ⁹ means a nitro group, an amino group, a halogen or a residue containing 1-8 carbon atoms, such as (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) -alkynyl, (C ₁ -C ₄ ) -haloalkyl, (C ₂ -C ₄ ) -haloalkenyl, (C ₂ -C ₄ ) -haloalkynyl, (C ₁ -C ₄ ) -halo-alkoxy, (C ₁ -C ₄ ) -haloalkylthio a group, (C ₁ -C ₄ ) -alkoxycarbonyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkylsulfinyl, (C ₁ -C ₄ ) -alkylthio, arylsulfonyl, arylsulfinyl, arylthio (C ₁ -C ₄ ) -alkoxyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkoxyl, (C ₁ -C ₄ ) -alkylcarbonyl, (C ₁ -C ₄ ) -alkylaminosulfonyl, (C ₁ -C ₄₎ -dialkilaminosulfonil, (C ₁ -C ₄₎ -alkilkarb moil, (C ₁ -C ₄₎ -dialkilkarbamoil, (C ₁ -C ₄₎ -alkoxy- (C ₁ -C ₄₎ -alkyl, phenoxy, cyano, aryl, alkylamino, dialkylamino;

R ¹⁰ means substituted or unsubstituted benzyl, substituted or unsubstituted heteroaryl, heterocyclyl, heteroaryl- (C ₁ -C ₄ ) -alkyl, di- (C ₁ -C4 ₎ -alkylphosphono (C ₁ -C ₄ ) -alkyl or SF ₅ ;

R ^{11 the} same or different, mean hydrogen, (C ₁ -C ₄ ) -alkyl, halogen;

R ¹² identical or different, mean (C ₁ -C) -alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl, halogen, (C ₁ -C ₄ ) -haloalkyl, (C ₂ -C ₄ ) -halo-alkenyl, (C ₂ -C ₄ ) -haloalkynyl, (C ₁ -C ₄ ) -halo-alkoxy, (C ₁ -C ₄ ) -haloalkylthio, (C ₁ -C ₄ ) - alkoxycarbonyl, (C ₁ -C ₄ ) -alkyl-sulfonyl, (C ₁ -C ₄ ) -haloalkylsulfonyl, (C ₁ -C ₄ ) -alkylsulfinyl, (C ₁ -C ₄ ) -haloalkylsulfinyl, (C ₁ -C ₄ ) -alkylthio group, (C ₁ -C ₄ ) -alkoxyl, (C ₁ -C ₄ ) -alkylcarbonyl, (C ₁ -C ₄ ) -alkylamino-sulfonyl, (C ₁ -C ₄ ) -alkylamino-sulfonyl, (C ₁ -C ₄ ) -alkylcarbamoyl, (C ₁ -C ₄ ) -alkylcarbamoyl, (C ₁ -C ₄ ) -alkoxyalkyl, phenoxy groups y, nitro group, cyano group, aryl, di- (C ₁ -C ₄ ) -alkylphosphono (C ₁ -C ₄ ) -alkyl;

q is 0, 1, 2, 3 or 4;

r is 0, 1, 2 or 3;

t is 1 or 2;

u is 0, 1 or 2;

v is 1 or 2;

X ¹ is O, CR ¹⁴ R ¹⁵ , CHOH, C = O, C = NO (C ₁ -C ₄ ) -alkyl;

X ² is O, S, SO, SO ₂ , CH ₂ , NH, N- (C ₁ -C ₄ ) -alkyl, NSO ₂ is (C ₁ -C ₄ ) -alkyl;

U ¹ together with the carbon atoms connected to it forms a carbocycle or heterocycle, which may be aromatic or fully or partially saturated;

U ² means O, S, SO, SO ₂ , CH ₂ , NH, N- (C ₁ -C ₄ ) -alkyl, NSO ₂ - (C ₁ -C ₄ ) -alkyl;

R ¹³ is hydrogen, (C ₁ -C ₄ ) alkyl, (C ₃ -C ₇ ) cycloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) alkynyl, optionally substituted phenyl, optionally substituted benzyl, (C ₁ -C ₄ ) acyl;

R ¹⁴ , R ^{15 the} same or different, mean hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxyl, (C ₁ -C ₄ ) -haloalkoxyl, (C ₁ -C ₄ ) - an alkylthio group, a (C ₁ -C ₄ ) haloalkylthio group, or R ¹⁴ and R ¹⁵ together form one of the groups: —O— (CH ₂ ) ₂ —O—, —O— (CH ₂ ) ₃ —O—, —S - (CH ₂ ) ₂ -S-, -S- (CH ₂ ) ₃ -S-, - (CH ₂ ) ₄ -, - (CH ₂ ) ₅ -;

R ¹⁶ means (C ₁ -C ₂ ) -alkyl;

Y ¹ , Y ² mean SO ₂ or CO, provided that Y ¹ ≠ Y ² ;

and

B. Protectively effective amount of one or more compounds from groups a) - e):

a) the compounds of formulas (II) to (IV):

and the symbols and indices have the following meanings:

n ’means a natural number 1-5, preferably 1-3;

T is a (C ₁ or C ₂ ) alkanediyl chain which is unsubstituted or substituted by one or two (C ₁ -C ₄ ) -alkyl radicals or [(C ₁ -C ₃ ) alkoxy] carbonyl;

W means an unsubstituted or substituted divalent heterocyclic residue from the group of partially unsaturated or aromatic five-membered heterocycles with 1-3 heteroatoms in an N or O type ring, wherein the ring contains at least one N atom and at most one O atom;

m ’means 0 or 1;

R ¹⁷ , R ^{19 the} same or different, mean hydrogen, halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxyl, nitro group or (C ₁ -C ₄ ) -haloalkyl;

R ¹⁸ , R ^{20 are the} same or different, mean OR ²⁴ , SR ²⁴ or NR ²⁴ R ²⁵ or a saturated or unsaturated 3-7 membered heterocycle with at least one N atom and with up to three heteroatoms, which through N the atom is bonded to a carbonyl group in the compound of formula (II) or (III), and is unsubstituted or substituted by residues selected from the group consisting of (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxyl or unsubstituted or substituted phenyl;

R ²⁴ means hydrogen or an unsubstituted or substituted aliphatic hydrocarbon residue;

R ²⁵ means hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₁ -C ₆ ) -alkoxyl or substituted or unsubstituted phenyl;

R ²⁶ means hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₆ ) hydroxyalkyl, (C ₃ -C ₁₂ ) cycloalkyl or tri [(C ₁ -C ₄ ) alkyl] silyl;

R ²⁷ , R ²⁸ , R ^{29 the} same or different, mean hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₃ -C ₁₂ ) -cycloalkyl or substituted or unsubstituted phenyl;

R ²¹ means (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -haloalkenyl, (C ₃ -C ₇ ) cycloalkyl;

R ²² , R ²³ identical or different, mean hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) -alkynyl, (C ₁ -C ₄ ) - haloalkyl, (C ₂ -C ₄ ) -halogen-alkenyl, (C ₁ -C ₄ ) -alkylcarbamoyl- (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl-carbamoyl- (C ₁ - C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, dioxolanyl- (C ₁ -C ₄ ) -alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R ²² and R ²³ together form a substituted or unsubstituted heterocycle; or b) one or more compounds selected from the group consisting of: 1,8 naphthalic acid anhydride; methyl diphenylmethoxyacetate; cyanomethoxyimino (phenyl) acetonitrile (cyometrininyl); 1,3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile (oxabetrinyl); 4'-chloro-2,2,2-trifluoroacetophenone-O-1,3-dioxolan-2-ylmethyloxime (fluxophenim);

4,6-dichloro-2-phenylprimimidine (phenclorim); benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole); 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191); N- (4-methylphenyl) -N ’- (1-methyl-1-phenylethyl) urea (dimron); 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea; 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea; 1- [4- (N-4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea; 1- [4- (N-2-naphthoylsulfamoyl) phenyl] -3,3-dimethylurea; (2,4-dichlorophenoxy) acetic acid (2,4-D); (4-chlorophenoxy) acetic acid; (R, S) -2- (4-chloro-o-tolyloxy) propionic acid (mecoprop);

4- (2,4-dichlorophenoxy) butyric acid (2,4-DB); (4-chloro-o-tolyloxy) acetic acid (MCPA); 4- (4-chloro-o-tolyloxy) butyric acid; 4- (4-chlorophenoxy) butyric acid; 3,6-dichloro-2-methoxybenzoic acid (dicamba); 1- (ethoxycarbonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloro); as well as their salts and esters; c) N-acylsulfonamides of the formula (V) and their salts:

where R ³⁰ means hydrogen, hydrocarbon residue, hydrocarbon radical, hydrocarbon residue or heterocyclyl residue, each of the last four residues being unsubstituted or substituted by one or more, same or different residues selected from the group consisting of halogen, cyano group, nitro group , an amino group, hydroxyl, carboxyl, formyl, carbonamido group, sulfonamido group and residues of the formula —Z ^a R ^a ;

R ³¹ means hydrogen or (C ₁ -C ₄ ) -alkyl; or

R ³⁰ and R ³¹ together with a group of the formula —CO — N— mean the remainder of a 3-8 membered saturated or unsaturated ring;

R ³² in the case where n = 1, or R ³² , independently of each other, if n is greater than 1, means halogen, cyano, nitro group, amino group, hydroxyl, carboxyl, formyl, CONH ₂ , SO ₂ NH ₂ or a residue of the formula —Z ^d —R ^d ;

R ³³ means hydrogen or (C ₁ -C ₄ ) -alkyl;

R ³⁴ in case m = 1, or R ³⁴ , independently of each other, if m is greater than 1, mean halogen, cyano group, nitro group, amino group, hydroxyl, carboxyl, CHO, CONH ₂ , SO ₂ NH ₂ or a residue of the formula —Z ^c —R ^c ;

R ^a means a hydrocarbon residue or heterocyclyl residue, each of these residues unsubstituted or substituted by one or more, same or different residues selected from the group consisting of halogen, cyano group, nitro group, amino group, hydroxyl, mono - and di [(C ₁ -C ₄ ) -alkyl] amino groups, or an alkyl residue in which several non-adjacent CH ₂ groups are optionally replaced by an oxygen atom;

R ^b , R ^c independently from each other mean a hydrocarbon residue or heterocyclyl residue, each of these residues unsubstituted or substituted by one or more, same or different residues selected from the group consisting of halogen, cyano group, nitro group, amino group, hydroxyl, phosphoryl , halogen- (C ₁ -C ₄ ) -alkoxyl, mono- and di [(C ₁ -C ₄ ) -alkyl] amino groups, or an alkyl radical in which several non-adjacent CH ₂ groups are replaced, if necessary an oxygen atom;

Z ^a is a divalent group of the formula —O—, —S—, —CO—, —CS—, —CO — O—, —CO — S—, —O — CO—, —S — CO—, —SO—, -SO ₂ -, -NR * -, -CO-NR * -, -NR * -CO-, -SO ₂ -NR * - or -NR * -SO ₂ -, and the link on the right side of the corresponding divalent group means a bond with the residue R ^a , and R * in the last five residues, independently from each other, respectively, mean H, (C ₁ -C ₄ ) -alkyl or halogen- (C ₁ -C ₄ ) -alkyl;

Z ^b , Z ^c independently from each other, mean a direct bond or a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-, -O-CO- , -S-CO-, -SO-, -SO ₂ -, -NR * -, -SO ₂ -NR * -, -NR * -SO ₂ -, -CO-NR * - or -NR * -CO- wherein the link on the right side of the corresponding divalent group means a bond with the residue R ^b or R ^c , and R * in the last five residues, independently of one another, means, respectively, H, (C ₁ -C ₄ ) -alkyl or halogen - (C ₁ -C ₄ ) -alkyl;

n is an integer of 0-4; and m is an integer of 0-5; g) amides of acylsulfamoylbenzoic acid of the general formula (VI), if necessary, also in salt form,

where X ³ means CH or N;

R ³⁵ means hydrogen, heterocyclyl or a hydrocarbon residue, the last two of which may be substituted by one or more, same or different residues selected from the group consisting of halogen, cyano group, nitro group, amino group, hydroxyl, carboxyl, CHO, CONH ₂ , SO ₂ NH ₂ and Z ^a —R ^a ;

R ³⁶ means hydrogen, hydroxyl, (C ₁ -C ₆ ) -alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) -alkynyl, (C ₁ -C ₆ ) -alkoxyl, (C ₂ -C ₆ ) -alkenyloxy group, wherein the last five residues may be substituted by one or more, same or different residues selected from the group consisting of halogen, hydroxyl, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) alkoxy and (C ₁ -C ₄ ) alkylthio group; or

R ³⁵ and R ³⁶ together with the nitrogen atom connected to them mean a 3-8 membered, saturated or unsaturated cycle;

R ³⁷ means halogen, cyano group, nitro group, amino group, hydroxyl, carboxyl, CHO, CONH ₂ , SO ₂ NH ₂ and Z ^b -R ^b ;

R ³⁸ is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) alkenyl or (C ₂ -C ₄ ) -alkynyl;

R ³⁹ means halogen, cyano, nitro, amino, hydroxyl, carboxyl, phosphoryl, CHO, CONH ₂ , SO ₂ NH ₂ and Z ^c -R ^c ;

R ^a means (C ₂ -C ₂₀ ) -alkyl residue, the carbon chain of which is once or repeatedly interrupted by oxygen atoms; a heterocyclyl or hydrocarbon residue, wherein the last two radicals may be substituted by one or more, same or different residues selected from the group consisting of halogen, cyano group, nitro group, amino group, hydroxyl, mono and di [(C ₁ -C ₄ ) - alkyl] amino groups;

R ^b , R ^{c are the} same or different, mean (C ₂ -C ₂₀ ) -alkyl residue, the carbon chain of which is one or more times interrupted by oxygen atoms; a heterocyclyl or hydrocarbon residue, wherein the last two residues may be substituted by one or more, same or different residues selected from the group consisting of halogen, cyano group, nitro group, amino group, hydroxyl, phosphoryl, (C ₁ -C ₄ ) haloalkoxyl, mono- and di [(C ₁ -C ₄ ) -alkyl] amino groups;

Z ^a means a divalent group selected from the group consisting of O, S, CO, CS, C (O) O, C (O) S, SO, SO ₂ , NR ^d , C (O) NR _d or SO ₂ NR ^d ;

Z ^b , Z ^c identical or different, mean a direct bond or a divalent group selected from the group consisting of O, S, CO, CS, C (O) O, C (O) S, SO, SO ₂ , NR ^d , SO ₂ NR ^d or C (O) NR ^d ;

R ^d means hydrogen, (C ₁ -C ₄ ) -alkyl or (C ₁ -C ₄ ) -haloalkyl;

n is an integer of 0-4; and

m in the case where X represents CH, means an integer of 0-5, and in the case where X represents N, means an integer of 0-4;

d) compounds of formula (VII):

where the symbols and indices have the following meanings: R ⁴⁰ means hydrogen; (C ₁ -C ₄ ) -alkyl; (C ₁ -C ₄ ) -alkyl substituted with (C ₁ -C ₄ ) -alkyl-X ⁴ or (C ₁ -C ₄ ) -halo-genoalkyl-X ⁴ ;

(C ₁ -C ₄ ) -haloalkyl, NO ₂ , CN, —COO-R ⁴³ , NR ₂ ⁴⁴ , SO ₂ NR ₂ ⁴⁵ or CONR ₂ ⁴⁶ ;

R ⁴¹ means hydrogen, halogen, (C ₁ -C ₄ ) -alkyl, CF ₃ , (C ₁ -C ₄ ) -alkoxyl or (C ₁ -C ₄ ) -haloalkoxy;

R ⁴² means hydrogen, halogen or (C ₁ -C ₄ ) -alkyl;

Q ¹ , Q ² , E, G, identical or different, mean —O—, —S—, —CR ₂ ⁴⁷ -, —CO—, NR ⁴⁸ or a group of formula (VIII):

C = CH-O-CR ₂ ^a - (CO) -A (VIII),

provided that

a) at least one of the groups Q ¹ , Q ² , E, G means a carbonyl group, one of these groups exactly means the remainder of the formula (VIII) and the group of the formula (VIII) is adjacent to the carbonyl group; and

b) two adjacent groups Q ¹ , Q ² , E and G at the same time cannot mean oxygen;

R ^{a the} same or different, mean hydrogen or (C ₁ -C ₈ ) -alkyl or both residues R _a together mean (C ₂ -C ₆ ) -alkylene;

And means R ^b -Y ³ - or -NR ₂ ⁴⁹ ;

X ⁴ is —O— or —S (O) p—;

Y ³ is —O— or —S—;

R ¹³ is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₈ ) -alkyl, (C ₃ -C ₆ ) alkenyloxy- (C ₁ -C ₈ ) -alkyl or phenyl- (C ₁ -C ₈ ) -alkyl, wherein the phenyl ring may be substituted with halogen, (C ₁ -C ₄ ) -alkyl, CF ₃ , methoxy or methyl S (O) _p ; (C ₃ -C ₆ ) alkenyl, (C ₃ -C ₆ ) haloalkenyl, phenyl- (C ₃ -C ₆ ) alkenyl, (C ₃ -C ₆ ) alkynyl, phenyl- (C ₃ -C ₆ ) -alkynyl, oxetanyl, furfuryl, tetrahydrofuryl;

R ⁴³ means hydrogen or (C ₁ -C ₄ ) -alkyl;

R ^{44 are the} same or different, are hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkylcarbonyl or both R ⁴⁴ residues together are (C ₄ -C ₅ ) -alkylene;

R ⁴⁵ , R ^{46 are the} same or different, are hydrogen, (C ₁ -C ₄ ) -alkyl, or both R ⁴⁵ and / or R ^{46 are} together (C ₄ -C ₅ ) -alkylene, with one CH _{2 being} the group can be replaced by O or S, or one or two CH ₂ groups can be replaced by —NR ^c -;

R ^c means hydrogen or (C ₁ -C ₈ ) -alkyl;

R ^{47 the} same or different, mean hydrogen, (C ₁ -C ₈ ) -alkyl, or both R ⁴⁷ residues together represent (C ₂ -C ₆ ) -alkylene;

R ⁴⁸ means hydrogen, (C ₁ -C ₈ ) -alkyl, substituted or unsubstituted phenyl, or benzyl unsubstituted or substituted on the phenyl ring;

R ^{49 the} same or different, mean hydrogen, (C ₁ -C ₈ ) -alkyl, phenyl, phenyl- (C ₁ -C ₈ ) -alkyl, and the phenyl ring can be substituted with F, Cl, Br, NO ₂ , CN, OCH ₃ , (C ₁ -C ₄ ) -alkyl or CH ₃ SO ₂ ; (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₈ ) -alkyl, (C ₃ -C ₆ ) alkenyl, (C ₃ -C ₆ ) -alkynyl or two R ⁴⁹ residues together represent (C ₄ —C ₅ ) -alkylene, wherein one CH ₂ group can be replaced by O or S, or one or two CH ₂ groups can be replaced by —NR ^d -;

R ^d means hydrogen or (C ₁ -C ₄ ) -alkyl;

m ″ means 0 or 1; ir means 0, 1 or 2;

including stereoisomers and agriculturally acceptable salts.

2. The herbicidal agent according to claim 1, characterized in that it includes a compound of formula (I), where the symbols and indices have the following meanings: R is hydrogen, (C ₁ -C ₄ ) alkoxycarbonyl; R ¹ is (C ₃ -C ₇ ) -cycloalkyl, (C ₁ -C ₄ ) -alkyl- (C ₃ -C ₇ ) -cycloalkyl; R ² means hydrogen; R ³ means hydrogen, (C ₁ -C ₄ ) -alkyl, arylsulfonyl, benzyl;

R ⁴ means (C ₁ -C ₄ ) -alkyl; R ⁵ means (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxyl; R ⁶ means hydroxyl, (C ₁ -C ₄ ) -alkoxyl; R ⁷ means (C ₃ -C ₇ ) -cycloalkyl; R ⁸ means a cyano group; m is an integer from 0 to 6; and

Z means the remainder of the group (Z1) - (Z4):

and the symbols and indices have the following meanings: R ⁹ means (C ₁ -C ₄ ) -alkyl, halogen, (C ₁ -C ₄ ) -halogenated, (C ₁ -C ₄ ) -halogen-alkoxyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkylsulfonyloxy group, (C ₁ -C ₄ ) -alkylsulfonylamino group, (C ₁ -C ₄ ) -alkoxycarbonyl;

R ¹⁰ means beneyl, triazolylmethyl, pyrazolylmethyl, thiazolylmethyl; di- (C ₁ -C ₄ ) -alkylphosphono- (C ₁ -C ₄ ) -alkyl;

R ¹¹ means (C ₁ -C ₄ ) -alkyl;

R ¹² is (C ₁ -C ₄ ) -alkyl, halogen, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -alkyl-sulfonyl, (C ₁ -C ₄ ) -alkoxycarbonyl;

q is 0, 1, 2, 3 or 4;

r is 0, 1, 2 or 3;

t is 1 or 2;

u is 0, 1 or 2;

v is 1 or 2;

X ¹ is O, CR ¹⁴ R ¹⁵ , CHOH, C = O, C = NO (C ₁ -C ₄ ) -alkyl;

X ² means SO ₂ ;

U ^1, together with its carbon atoms, forms a pyrazole, imidazole, pyrrole, pyridine, pyrimidine, thiazole, thienyl, oxazole or furan ring;

U ² means SO ₂ ;

R ¹³ is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₇ ) -cycloalkyl, (C ₂ -C ₄ ) alkenyl, (C ₂ -C ₄ ) -alkynyl, optionally substituted phenyl, optionally substituted benzyl, (C ₁ -C ₄ ) acyl;

R ¹⁴ , R ^{15 the} same or different, mean hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxyl, (C ₁ -C ₄ ) -haloalkoxyl, (C ₁ -C ₄ ) - an alkylthio group, a (C ₁ -C ₄ ) haloalkylthio group; or R ¹⁴ and R ¹⁵ together form one of the groups: —O— (CH ₂ ) ₂ —O—, —O— (CH ₂ ) ₃ —O—, —S— (CH ₂ ) ₂ —S—, —S - (CH ₂ ) ₃ -S-, - (CH ₂ ) ₄ -, - (CH ₂ ) ₅ -;

R ¹⁶ means (C ₁ -C ₂ ) -alkyl;

Y ¹ , Y ² mean SO ₂ or CO, provided that Y ¹ ≠ Y ² .

3. The herbicidal agent according to claim 1 or 2, characterized in that W in the formula (II) means a residue from the group (W1) to (W4)

and the symbols and indices have the following meanings:

m ’means 0 or 1;

R ²⁶ means hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₆ ) hydroxyalkyl, (C ₃ -C ₁₂ ) cycloalkyl or three [(C ₁ -C ₄ ) alkyl] silyl;

R ²⁷ , R ²⁸ , R ^{29 the} same or different, mean hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₃ -C ₁₂ ) -cycloalkyl or substituted or unsubstituted phenyl.

4. The herbicidal agent according to any one of claims 1 to 3, containing a tread of the formula (II) and / or (III), in which the symbols and indices have the following meanings:

R ¹⁸ , R ^{20 are} —OR ²⁴ ;

R ²⁴ means hydrogen, (C ₁ -C ₁₈ ) -alkyl, (C ₃ -C ₁₈ ) -cycloalkyl, (C ₂ -C ₈ ) -alkenyl and (C ₂ -C ₁₈ ) -alkynyl, the carbon-containing groups being substituted by one or more residues R ⁵⁰ ;

R ⁵⁰ identical or different, mean halogen, hydroxyl, (C ₁ -C ₈ ) -alkoxyl, (C ₁ -C ₈ ) -alkylthio group, (C ₂ -C ₈ ) -alkenylthio group, (C ₂ -C ₈ ) -alkiniltio group, a (C ₂ -C ₈₎ -alkenilok-sigruppu, (C ₂ -C ₈₎ -alkiniloksigruppu, (C ₃ -C ₇₎ -cycloalkyl, (C ₃ -C ₇₎ cycloalkoxy, cyano, mono - and di [(C ₁ -C ₄ ) -alkyl] amino group, carboxyl, (C ₁ -C ₈ ) -alkoxycarbonyl, (C ₂ -C ₈ ) -alkenyloxycarbonyl, (C ₁ -C ₈ ) -alkylthiocarbonyl, (C ₂ -C ₈ ) -alkynyloxycarbonyl, (C ₁ -C ₈ ) -alkylcarbonyl, (C ₂ -C ₈ ) -alkenylcarbonyl, (C ₂ -C ₈ ) -alkynylcarbonyl, 1- (hydroxyimino) - (C ₁ -C ₆ ) -alkyl, 1 - [(C ₁ -C ₄ ) -alkylimino] - (C ₁ -C ₄ ) -alk il, 1 - [(C ₁ -C ₄ ) alkoxyimino] - (C ₁ -C ₆ ) -alkyl, (C ₁ -C ₈ ) -alkylcarbonylamino, (C ₂ -C ₈ ) -alkenylcarbonylamino, (C ₂ - C ₈ ) -alkynylcarbonylamino group, aminocarbonyl, (C ₁ -C ₈ ) -alkyl-aminocarbonyl, di [(C ₁ -C ₆ ) -alkyl] aminocarbonyl, (C ₂ -C ₆ ) -alkenylaminocarbonyl, (C ₂ -C ₆ ) -alkynylaminocarbonyl, (C ₁ -C ₈ ) -alkoxycarbonylamino group, (C ₁ -C ₈ ) -alkylaminocarbonylamino group, (C ₁ -C ₆ ) -alkylcarbonyloxy group which is unsubstituted or substituted with R ⁵¹ , (C ₂ -C ₆₎ -alkenyl-carbonyloxy, (C ₂ -C ₆₎ -alkinilkarboniloksigruppu, (C ₁ -C ₈₎ -alkylsulfonyl, phenyl, feni - (C ₁ -C ₆₎ -alkoxy, phenyl- (C ₁ -C ₆₎ -alkoxycarbonyl, phenoxy, phenoxy- (C ₁ -C ₆₎ -alkoxy, phenoxy (C ₁ -C ₆₎ -alkoxycarbonyl, phenylcarbonyloxy , phenylcarbonylamino group, phenyl- (C ₁ -C ₆ ) -alkylcarbonylamino group, wherein the last 9 residues in the phenyl ring are unsubstituted or are substituted once or more with R ⁵² ; SiR ' ₃ , -O-SiR' ₃ , R ' ₃ Si- (C ₁ -C ₆ ) -alkoxyl, -CO-O-NR' ₂ , -ON = CR ' ₂ , -N = CR' ₂ , - O-NR ' ₂ , -NR' ₂ , -CH (OR ') ₂ , -O- (CH ₂ ) _m -CH (OR') ₂ , -CR '″ (OR') ₂ , -O- (CH ₂ ) _m CR '"(OR") ₂ or R ″ O-CHR'"CHCOR" - (C ₁ -C ₆ ) alkoxyl;

R ⁵¹ identical or different, mean halogen, nitro group, (C ₁ -C ₄ ) -alkoxyl and unsubstituted or substituted by one or more Y phenyl radicals;

R ⁵² identical or different, mean halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxyl, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -haloalkoxy or nitro ;

R 'identical or different, mean hydrogen, (C ₁ -C ₄ ) -alkyl unsubstituted or substituted by one or more R ⁵² residues phenyl or two R' residues together form a (C ₂ -C ₆ ) alkanediyl chain;

R "identical or different, means a (C ₁ -C ₄ ) -alkyl or two R radicals together form a (C ₂ -C ₆ ) alkanediyl chain;

R '"means hydrogen or (C ₁ -C ₄ ) -alkyl;

m is 0, 1, 2, 3, 4, 5, or 6.

5. The herbicidal agent according to any one of claims 1 to 4, containing a tread of the formula (II) and / or (III), in which the symbols and indices have the following meanings:

R ²⁴ means hydrogen, (C ₁ -C ₈ ) -alkyl or (C ₃ -C ₇ ) -cycloalkyl, wherein the aforementioned carbon-containing residues are unsubstituted or are substituted once or twice with halogen or substituted once or twice with residues R ⁵⁰ ;

R ^{50 are the} same or different, are hydroxyl, (C ₁ -C ₄ ) alkoxy, carboxyl, (C ₁ -C ₄ ) alkoxycarbonyl, (C ₂ -C ₆ ) alkenyloxycarbonyl, (C ₂ -C ₆ ) alkynyloxy -carbonyl, 1- (hydroxy-imino) - (C ₁ -C ₄ ) -alkyl, 1 - [(C ₁ -C ₄ ) -alkylimino] - (C ₁ -C ₄ ) -alkyl and 1 - [(C ₁ -C ₄ ) alkoxyimino] - (C ₁ -C ₄ ) -alkyl; -SiR ' ₃ , -ON = CR' ₂ , -N = CR ' ₂ , -NR' ₂ and -O-NR ' ₂ , where R', identical or different, mean hydrogen, (C ₁ -C ₄ ) - alkyl or in pairs form a (C ₄ -C ₅ ) alkane-diyl chain;

R ²⁷ , R ²⁸ , R ^{29 the} same or different, mean hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₆ ) -haloalkyl, (C ₃ -C ₇ ) -cycloalkyl or phenyl, which is unsubstituted or substituted by one or more residues selected from the group consisting of halogen, cyano group, nitro group, amino group, mono- and di [(C ₁ -C ₄ ) -alkyl] amino group, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -alkoxyl, (C ₁ -C ₄ ) -haloalkoxy, (C ₁ -C ₄ ) -alkylthio and (C ₁ -C ₄ ) -alkylsulfonyl;

R ²⁶ means hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₆ ) hydroxyalkyl, (C ₃ -C ₇ ) cycloalkyl or three [(C ₁ -C ₄ ) alkyl] silyl;

R ¹⁷ , R ^{19 the} same or different, mean hydrogen, halogen, methyl, ethyl, methoxy group, ethoxy group, (C ₁ or C ₂ ) -halogenated.

6. The herbicidal agent according to any one of claims 1 to 5, containing a protector of formula (II), and the symbols and indices have the following meanings:

R ¹⁷ means hydrogen, halogen, nitro group or (C ₁ -C ₄ ) -halogenated;

n ’means 1, 2 or 3;

R ¹⁸ means a residue of the formula OR ²⁴ ;

R ²⁴ means hydrogen, (C ₁ -C ₈ ) -alkyl or (C ₃ -C ₇ ) -cycloalkyl, wherein the aforementioned carbon-containing residues are unsubstituted or are substituted once or twice by the same or different halides or up to twice substituted by the same or different residues selected from the group consisting of hydroxyl, (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkoxycarbonyl, (C ₂ -C ₆ ) alkenyloxycarbonyl, (C ₂ -C ₆ ) alkynyloxycarbonyl , 1- (hydroxyimino) - (C ₁ -C ₄ ) -alkyl, 1 - [(C ₁ -C ₄ ) -alkylimino] - (C ₁ -C ₄ ) -alkyl, 1 - [(C ₁ -C ₄ ) -alkoxyimino] - (C ₁ -C ₄ ) -alkyl and residues of the formulas -SiR ' ₃ , -ON = R ' ₂ , -N = CR' ₂ , -NR ' ₂ and -O-NR' ₂ , and the residues R 'in the above formulas, the same or different, mean hydrogen, (C ₁ -C ₄ ) -alkyl or in pairs form (C ₄ or C ₅ ) alkanediyl;

R ²⁷ , R ²⁸ , R ^{29 the} same or different, mean hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₆ ) -haloalkyl, (C ₃ -C ₇ ) -cycloalkyl or phenyl, which is unsubstituted or substituted by one or more residues selected from the group consisting of halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxyl, nitro group, (C ₁ -C ₄ ) -halogen-alkyl and (C ₁ -C ₄ ) haloalkoxyl; and

R ²⁶ means hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₆ ) hydroxyalkyl, (C ₃ -C ₇ ) cycloalkyl or tri [(C ₁ -C ₄ ) alkyl] silyl.

7. The herbicidal agent according to any one of claims 1 to 6, characterized in that the mass ratio of herbicide: tread is from 1: 100 to 100: 1.

8. The herbicidal agent according to any one of claims 1 to 7, characterized in that it contains another herbicide.

9. The herbicidal agent of claim 8, wherein the other herbicide is sulfonylurea.

10. A method for controlling weeds in crops, characterized in that a herbicidally effective amount of a combination of a herbicide with a tread according to any one of claims 1 to 9 is applied to weeds, plants, plant seeds or the area on which the plants grow.

11. The method according to claim 10, characterized in that the plants are a group of plants consisting of corn, wheat, rye, barley, oats, rice, sorghum, cotton and soy.

12. The method according to claim 10 or 11, characterized in that the plants are altered by genetic engineering.