RU2001117066A

RU2001117066A - Herbicide and Antidote Combinations

Info

Publication number: RU2001117066A
Application number: RU2001117066/04A
Authority: RU
Inventors: Франк Цимер; Лотар Вилльмс; Херманн Бирингер; Эрвин Хакер
Original assignee: Авентис Кропсайенс Гмбх
Priority date: 1998-11-21
Filing date: 1999-11-05
Publication date: 2003-06-27

Claims

1. Herbicidal active agent containing a mixture of

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

in which V means the radical (V1) - (V4)

where R is hydrogen, (C ₁ -C ₄ ) -alkoxycarbonyl, (C ₁ -C ₄ ) -haloalkoxycarbonyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkylsulfinyl, (C ₁ -C ₄ ) -alkylthio, COOH, cyano;

R ¹ means hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl, (C ₃ -C ₈ ) -cycloalkyl, (C ₃ -C ₈ ) -cycloalkenyl, (C ₁ -C ₄ ) -alkyl- (C ₃ -C ₈ ) -cycloalkyl, (C ₃ -C ₇ ) -halogenocycloalkyl, (C ₁ -C ₄ ) -alkylthio (C ₃ -C ₈ ) cycloalkyl, (C ₁ -C ₈ ) haloalkyl or (C ₂ -C ₈ ) haloalkenyl;

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

R ³ means hydrogen, (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, unsubstituted or substituted (C ₁ -C ₄ ) -alkyl, arylcarbonyl- (C ₁ -C ₄ ) -alkyl, unsubstituted or substituted by (C ₁ -C ₄ ) -alkyl, or aryl (C ₁ -C ₄ ) -alkyl, unsubstituted or substituted with (C ₁ -C ₄ ) -alkyl;

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

R ⁵ means (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, (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, halogen, substituted or unsubstituted aryl, tetrahydropyran-4-yl, tetrahydropyran-3-yl, tetrahydrothiopyran-3-yl, 1- methylthio-cyclopropyl, 2-ethylthiopropyl, or two R ⁵ radicals together are (C ₂ -C ₄ ) alkylene;

R ⁶ means hydroxy, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₈ ) -haloalkoxy, formyloxy, (C ₁ -C ₄ ) -alkylcarbonyloxy, (C ₁ -C ₄ ) -alkylsulfonyloxy, (C ₁ -C ₄ ) -alkylthio, (C ₁ -C ₄ ) -haloalkylthio, arylthio, aryloxy, (C ₁ -C ₄ ) -alkyl sulfinyl or (C ₁ -C ₄ ) -alkylsulfonyl;

R ⁷ means (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₃ -C ₈ ) -cycloalkyl, (C ₁ -C ₄ ) -alkyl- (C ₃ -C ₈ ) cycloalkyl or (C ₃ -C ₈ ) halogenocycloalkyl;

R ⁸ means a cyano group, (C ₁ -C ₄ ) -alkoxycarbonyl, (C ₁ -C ₄ ) -alkylcarbonyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkylsulfinyl, (C ₁ -C ₄ ) -alkylthio, (C ₁ -C ₄ ) -alkylaminocarbonyl or (C ₁ -C ₄ ) -dialkylaminocarbonyl;

1 = 0-6, and for 1≥2, the radicals R ⁵ may be the same or different from each other;

R ^{9 are the} same or different and mean a nitro, amino group, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl, halogen, (C ₁ -C ₄ ) -haloalkyl, (C ₂ -C ₄ ) -haloalkenyl, (C ₂ -C ₄ ) -haloalkynyl, (C ₁ -C ₄ ) -haloalkoxy, (C ₁ -C ₄ ) -haloalkylthio, (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 ) -alkoxy, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkylthio (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkylcarbonyl, (C ₁ -C ₄₎ -alkilaminosulfonil, (C ₁ -C ₄₎ -dialkilaminosulfonil, (C ₁ -C ₄₎ -alkilkarbamoil, (C ₁ -C ₄₎ dialkyl lkarbamoil, (C ₁ -C ₄₎ -alkoxy- (C ₁ -C ₄₎ -alkyl, phenoxy, cyano, aryl, alkylamino or dialkylamino;

q = 0, 1, 2, 3 or 4,

B. an effective amount of one or more substances acting as an antidote from the group:

a) compounds of formulas II, III and IV

where n '= 0-5;

T means 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 radical from the group of partially unsaturated or aromatic five-membered heterocycles with 1 to 3 heteroatoms in an N or O type ring, with at least one N atom and not more than one O atom in the ring, preferably a radical from the group ( W1) - (W4),

m '= 0 or 1;

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

R ¹⁸ , R ^{20 are the} same or different and 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 containing up to 3 heteroatoms, which through the N atom are bonded to the carbonyl the group in (II), respectively, in (III) and is unsubstituted or substituted by radicals from the group (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy or, optionally, substituted phenyl;

R ²⁴ means hydrogen or an unsaturated or saturated aliphatic hydrocarbon radical;

R ²⁵ means hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₁ -C ₆ ) -alkoxy 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 are the} same or different and 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 are the} same or different and 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 ) -haloalkenyl, (C ₁ -C ₄ ) -alkylcarbamoyl- (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenylcarbamoyl- (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 heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine q kl;

b) one or more compounds from the group:

1,8-naphthalic acid anhydride,

methyl diphenylmethoxyacetate,

cyanomethoxyimino (phenyl) acetonitrile (cyometrininyl),

1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile (oxabetrininyl),

4'-chloro-2, 2, 2-trifluoroacetophenone-O-1, 3-dioxolan-2-ylmethyl-

oxime (fluxophenim),

4,6-dichloro-2-phenylpyrimidine (fenchlorim),

(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-dimethylbenzoyl sulfamoyl) phenyl] -3-methylurea, 1- [4- (N-naphthoyl sulfamoyl) 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-chloro-o-tolyloxy) butyric acid,

(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

in which R ³⁰ means hydrogen, a hydrocarbon radical, an oxycarbon radical, a thiohydrocarbon radical or a heterocyclyl radical, each of the last four radicals being unsubstituted or substituted by one or more identical or different radicals from the group: halogen, cyano, nitro, amino, hydroxy -, a carboxy group, formyl, carbonamide, sulfonamide, and radicals of the formula —Z ^a —R ^a , each hydrocarbon part preferably containing 1-20 carbon atoms and the carbon-containing radical R ³⁰ containing, including substituents, respectfully 1-30 C atoms;

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

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

R ³² means the same or different halogen, cyano, nitro, amino, hydroxy, carboxy, formyl, CONH ₂ , SO ₂ NH ₂ or a radical of the formula —Z ^b —R ^b ;

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

R ³⁴ means the same or different halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, COMN ₂ , SO ₂ NH ₂ or a radical of the formula Z ^C -R ^C ;

R ^a means a hydrocarbon radical or a heterocyclyl radical, each of the two named radicals being unsubstituted or substituted by one or more, same or different radicals from the group: halogen, cyano, nitro, amino, hydroxy, mono and di - [( A C ₁ -C ₄ ) -alkyl] -amino group, or an alkyl radical in which several, preferably 2 or 3, non-adjacent CH ₂ groups are replaced by oxygen atoms;

R ^b , R ^{c are the} same or different and mean a hydrocarbon radical or heterocyclyl radical, each of the two named radicals being unsubstituted or substituted by one or more, same or different radicals from the group: halogen, cyano, nitro, amino, hydroxy, phosphoryl , halogen- (C ₁ -C ₄ ) -alkoxy mono- and di- ((C ₁ -C ₄ ) -alkyl] amino group, or an alkyl radical in which several, preferably 2 or 3, non-adjacent CH ₂ groups are replaced to oxygen atoms;

Z ^a means 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 , moreover, the bond shown on the right of the corresponding divalent group is a bond with the radical R ^a , while the radicals R * in the last five named radicals mean independently H, (C ₁ -C ₄ ) -alkyl or halogen- (C ₁ -C ₄ ) -alkyl;

Z ^b , Z ^c independently from each other mean a single bond or a divalent group of the formula O, S, CO, CS, CO-0, CO-S, O-CO, S-CO, SO, SO ₂ , NR *, SO ₂ -NR *, NR * -SO ₂ , CO-NR * or NR * -CO, and in the case of asymmetric divalent groups, the atom to the right is bound to the radical R ^b , respectively, R ^c , with the radicals R * in the last five the radicals referred to are independently H, (C ₁ -C ₄ ) -alkyl or halogen- (C ₁ -C ₄ ) -alkyl;

n = 0-4,

t = 0-5,

d) amides of acylsulfamoylbenzoic acid of general formula (VI), if necessary, and their salts

in which X is CH or N;

R ³⁵ means hydrogen, heterocyclyl or a hydrocarbon radical, and the last two radicals, if necessary, are substituted by one or more, same or different radicals from the series halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH ₂ , SO ₂ NH ₂ and Z ^d —R ^d ;

R ³⁶ means hydrogen, hydroxy group, (C ₁ -C ₆ ) -alkyl, (C ₂ -C ₆ ) alkenyl, (C ₂ -C ₆ ) -alkynyl, (C ₁ -C ₆ ) -alkoxy, (C ₂ -C ₆ ) -alkenyloxy, the last five radicals being optionally substituted with one or more identical or different radicals from the series halogen, hydroxy-group, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy and (C ₁ -C ₄ ) -alkylthio,

or R ³⁵ and R ³⁶ form, together with the nitrogen atom to which they are attached, a 3-8 membered saturated or unsaturated ring;

R ³⁷ means the same or different halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH ₂ , SO ₂ NH ₂ or Z ^e -R ^e ;

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

R ³⁹ means the same or different halogen, cyano, nitro, amino, hydroxy, carboxy, phosphoryl, CHO, CONH ₂ , SO ₂ NH ₂ or Z ^f -R ^f ;

R ^d means a (C ₂ -C ₂₀ ) -alkyl radical, the hydrocarbon chain of which is interrupted once or repeatedly by oxygen atoms, a heterocyclyl or hydrocarbon radical, the last two radicals being optionally substituted by one or more, same or different radicals from the series halogen, cyano- , nitro-, amino-, hydroxy-, mono- and di - [(C ₁ -C ₄ ) -alkyl] amino;

R ^e , R ^{f are the} same or different and mean a (C ₂ -C ₂₀ ) -alkyl radical, the hydrocarbon chain of which is once or repeatedly interrupted by oxygen atoms, a heterocyclyl or hydrocarbon radical, the last two radicals being optionally substituted with one or more identical ones or various halo, cyano, nitro, amino, hydroxy, phosphoryl, (C ₁ -C ₄ ) -haloalkoxy, mono- and di - [(C ₁ -C ₄ ) -alkyl] -amino radicals;

Z ^d means a divalent group of the formula O, S, CO, CS, C (O) O, C (O) S, SO, SO ₂ , NR *, C (O) NR * or SO ₂ NR *;

Z ^e , Z ^{f are the} same or different and mean a single bond or a divalent group of the formula O, S, CO, CS, C (O) O, C (O) S, SO, SO ₂ , NR *, SO ₂ NR * or C (O) NR *;

R * is hydrogen, (C ₁ -C ₄ ) -alkyl or (C ₁ -C ₄ ) -haloalkyl;

s = 0-4,

o = 0-5 when X means CH, and o = 0-4 when X means N,

including stereoisomers and salts used in agriculture, excluding mixtures in which a) in the compound of formula (I) V = V1 or V4, and the antidote has the formula IV or is selected from the range: 1,8 naphthalic acid anhydride, methyl diphenylmethoxyacetate, 2-dichloromethyl-2-methyl-1,3-dioxolane, cyanomethoxyimino (phenyl) acetonitrile, 1,3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile, 4'-chloro-2,2,2-trifluoroacetophenone-O-1 , 3-dioxolan-2-ylmethyloxy, 4, 6-dichloro-2-phenylpyrimidine, benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate and (5-chloro-8-quinolinoxy) acetic acid - (1-met ilhexyl) ether, or b) in the compound of formula (I) V = V3 with R ⁶ = OH and the antidote has the formula (II), where W = W1, W2, W3 or W4, m '= 1, or formula (III) and T means (C ₁ - or C ₂ -) - alkanediyl chain which is unsubstituted or substituted by one or two (C ₁ -C ₄ ) -alkyl radicals, or formula (IV), or means a compound from the series anhydride 1,8- naphthalic acid, cyanomethoxyimino (phenyl) acetonitrile, oxabetrinyl, fluxophenim and furazole.

2. A herbicidal agent according to claim 1, wherein in the compound of formula (I) V is a radical from the group (V1) to (V4)

where 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 substituted with (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkyl-arylcarbonylmethyl, benzyl;

R ⁴ means (C ₁ -C ₄ ) -alkyl;

R ⁵ is (C ₁ -C ₄ ) -alkyl, - (C ₁ -C ₄ ) -alkoxy, or the two R ⁵ radicals together are C ₂ -alkenyl;

R ⁶ is hydroxy, (C ₁ -C ₄ ) alkoxy, phenylthio;

R ⁷ means (C ₃ -C ₇ ) -cycloalkyl;

R ⁸ means a cyano group;

1 = 0-3, and for 1≥2, the radicals R ⁵ may be the same or different from each other;

R ^{9 are the} same or different and mean (C ₁ -C ₄ ) -alkyl, halogen, nitro, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -haloalkoxy, (C ₁ -C ₄ ) -alkylsulfonyl , (C ₁ -C ₄ ) -alkylsulfonyloxy, (C ₁ -C ₄ ) -alkylsulfonylamino, (C ₁ -C ₄ ) -alkoxycarbonyl;

q is 0, 1, 2 or 3;

3. A herbicidal agent according to claims 1 and 2, containing antidotes of formulas (II) and / or (III), in which R ¹⁸ , R ²⁰ mean OR ²⁴ ; R ²⁴ means hydrogen, (C ₁ -C ₁₈ ) -alkyl, (C ₃ -C ₁₂ ) -cycloalkyl, (C ₂ -C ₈ ) -alkenyl and (C ₂ -C ₁₈ ) -alkynyl, with groups containing carbon may be substituted by one or more substituents R ⁵⁰ , R ⁵⁰ mean the same or different halogen, hydroxy group, (C ₁ -C ₈ ) alkoxy, (C ₁ -C ₈ ) alkylthio, (C ₂ -C ₈ ) alkenylthio , (C ₂ -C ₈ ) alkynylthio, (C ₂ -C ₈ ) alkenyloxy, (C ₂ -C ₈ ) alkynyloxy, (C ₃ -C ₇ ) cycloalkyl, (C ₃ -C ₇ ) cycloalkoxy , cyano, mono and di - ((C ₁ -C ₄ ) -alkyl) amino, carboxy, (C ₁ -C ₈ ) -alkoxycarbonyl, (C ₂ -C ₈ ) alkenyloxycarbonyl, (C ₁ - C ₈ ) -alkylthiocarbonyl, (C ₂ -C ₈ ) -alkini Loxycarbonyl, (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 ) -alkyl, 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, aminocarbonyl, (C ₁ -C ₈ ) -alkylaminocarbonyl, di- (C ₁ -C ₆ ) -alkylaminocarbonyl, (C ₂ -C ₆ ) -alkenylaminocarbonyl, (C ₂ -C ₆ ) -alkynylaminocarbonyl, (C ₁ -C ₈ ) -alkoxycarbonylamino, (C ₁ -C ₈ ) -alkylaminocarbonylamino, (C ₁ -C ₆ ) -alkylcarbonyloxy, which is unsubstituted or substituted by R ^51, (C ₂ -C ₆₎ -alkenilk rboniloksi, (C ₂ -C ₆₎ -alkinilkarboniloksi, (C ₁ -C ₈₎ -alkylsulfonyl, phenyl, phenyl- (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, phenyl- (C ₁ -C ₆ ) -alkylcarbonylamino, the last 9 radicals being unsubstituted or substituted on the phenyl ring one or more substituents R ⁵² ; SiR ' ₃ , OSiR' ₃ , R ' ₃ Si- (C ₁ -C ₈ ) -alkoxy, CO-O-NR' ₂ , ON = CR ' ₂ , N = CR' ₂ , O-NR ' ₂ , NR ' ₂ , CH (OR') ₂ , O- (CH ₂ ) _w -CH (OR ') ₂ , CR "' (OR ') ₂ , O (CH ₂ ) _w CR"' (OR ") ₂ , or R "O-CHR"'CHCOR"- (C ₁ -C ₆ ) alkoxy; R ^{51 are the} same or different and mean halogen, nitro group, (C ₁ -C ₄ ) -alkoxy and phenyl unsubstituted or substituted by one or more R ⁵² radicals; R ^{52 are the} same or different and mean halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -haloalkoxy or nitro group ; R 'are the same or different and mean hydrogen, (C ₁ -C ₄ ) -alkyl, phenyl unsubstituted or substituted by one or more R ⁵² radicals, or two R' radicals together form a (C ₂ -C ₆ ) alkanediyl chain;

R "are the same or different and mean 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;

w = 0, 1, 2, 3, 4, 5, or 6.

4. A herbicidal agent according to claims 1 and 2, containing antidotes of formula (V) or a salt thereof, in which R ³⁰ means hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₃ -C ₆ ) -cycloalkyl, furanyl or thienyl, each of the last four radicals being unsubstituted or substituted by one or more radicals from the group: halogen, (C ₁ -C ₄ ) alkoxy, halogen- (C ₁ -C ₆ ) alkoxy and (C ₁ -C ₄ ) -alkylthio and, in the case of cyclic radicals, also (C ₁ -C ₄ ) -alkyl and (C ₁ -C ₄ ) -haloalkyl; R ³¹ means hydrogen, R ³² means halogen, halogen- (C ₁ -C ₄ ) -alkyl, halogen- (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkoxycarbonyl or (C ₁ -C ₄ ) -alkylcarbonyl, preferably halogen, (C ₁ -C ₄ ) -haloalkyl, for example trifluoromethyl, (C ₁ -C ₄ ) alkoxy, halogen (C ₁ -C ₄ ) alkoxy, (C ₁ -C ₄ ) alkoxycarbonyl or (C ₁ -C ₄ ) alkylsulfonyl; R ³³ means hydrogen; R ³⁴ means halogen, (C ₁ -C ₄ ) -alkyl, halogen- (C ₁ -C ₄ ) -alkyl, halogen- (C ₁ -C ₄ ) -alkoxy, (C ₃ -C ₆ ) -cycloalkyl, phenyl , (C ₁ -C ₄ ) -alkoxy, cyano, (C ₁ -C ₄ ) -alkylthio, (C ₁ -C ₄ ) -alkylsulfinyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkoxycarbonyl or (C ₁ -C ₄ ) -alkylcarbonyl, preferably halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, e.g. trifluoromethyl, halogen- (C ₁ -C ₄ ) alkoxy,

(C ₁ -C ₄ ) alkoxy or (C ₁ -C ₄ ) alkylthio; n = 0, 1 or 2, t = 1 or 2.

5. A herbicidal agent according to claim 1 or 2, containing antidotes of the formula (VI), in which X ³ means CH; R ³⁵ means hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₃ -C ₆ ) -cycloalkyl, (C ₂ -C ₆ ) -alkenyl, (C ₅ -C ₆ ) -cycloalkenyl, phenyl or 3-6 a-membered heterocyclyl containing up to three heteroatoms from the series nitrogen, oxygen and sulfur, the last six radicals being optionally substituted with one or more, same or different substituents from the series halogen, (C ₁ -C ₆ ) alkoxy, (C ₁ -C ₆ ) -haloalkoxy, (C ₁ -C ₂ ) -alkylsulfinyl, (C ₁ -C ₂ ) -alkylsulfonyl, (C ₃ -C ₆ ) -cycloalkyl, (C ₁ -C ₄ ) -alkoxycarbonyl, (C ₁ -C ₄ ) -alkylcarbonyl, and phenyl, and in the case of cyclic radicals, also (C ₁ -C ₄ ) -alkyl and (C ₁ -C ₄ ) haloalkyl; R ³⁶ means hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₂ -C ₆ ) -alkenyl, (C ₂ -C ₆ ) -alkynyl, the last three radicals being optionally substituted with one or more identical or various substituents from the range of halogen, hydroxy, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy and (C ₁ -C ₄ ) -alkylthio; R ³⁷ means the same or different halogen, (C ₁ -C ₄ ) -halogenated, (C ₁ -C ₄ ) -haloalkoxy, nitro, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkoxycarbonyl or (C ₁ -C ₄ ) -alkylcarbonyl; R ³⁸ means hydrogen; R ³⁹ means the same or different halogen, nitro group, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -haloalkoxy, (C ₃ -C ₆ ) -cycloalkyl, phenyl, (C ₁ -C ₄ ) alkoxy, cyano, (C ₁ -C ₄ ) alkylthio, (C ₁ -C ₄ ) alkylsulfinyl, (C ₁ -C ₄ ) alkylsulfonyl, (C ₁ -C ₄ ) -alkoxycarbonyl or (C ₁ -C ₄ ) -alkylcarbonyl;

s = 0, 1 or 2,

o = 1 or 2.

6. A herbicidal agent according to one or more of claims 1 to 5, in which the weight ratio of herbicide: antidote is from 1: 100 to 100: 1.

7. A herbicidal agent according to one or more of claims 1 to 6, which contains an additional herbicide.

8. The herbicidal agent of claim 7, wherein the additional herbicide is sulfonylurea.

9. A method of controlling weeds in useful plant cultures, characterized in that the herbicidally active amount of the herbicidally active substance, according to one or more of claims 1 to 8, is applied to weeds, cultivated plants, plant seeds or to the soil surface where the plants grow.

10. The method according to claim 9, characterized in that they mean plants from the group of corn, wheat, rye, barley, rice, oats, sorghum, cotton and soy.

11. The method according to claim 9 or 10, characterized in that the plants are altered by gene technology.

12. The use of a herbicidally acting agent, according to one or more of claims 1 to 8, for weed control in crops of useful plants.