US2006030485A1PendingUtilityA1
Herbicide/safener combinations
Est. expiryNov 21, 2018(expired)· nominal 20-yr term from priority
A01N 43/56A01N 43/80A01N 35/06A01N 25/32A01N 37/42
59
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Claims
Abstract
There are described herbicidal compositions which comprise at least one herbicidally active compound of the formula (I) and at least one crop-plant-protecting compound as safener. In this formula (I), V is an optionally substituted radical selected from the group consisting of isoxazol-4-yl, pyrazol-4-yl, cyclohexane-1,3-dion-2-yl and 3-oxopropionitril-2-yl and R 9 is nitro, amino, halogen or a carbon-containing radical. The group of the safeners contains, for example, 2,4-D, cyometrinil, dicamba, dymron, fenclorim, flurazole, fluxofenim, lactidichlor, MCPA, mecoprop, MG-191, oxabetrinil, methyl diphenylmethoxyacetate, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1,8-naphthalaic anhydride, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-naphthoylsulfamoyl)phenyl]-3,3-dimethylurea, (4-chlorophenoxy)acetic acid, 4-(2,4-dichlorophenoxy)butyric acid, 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, in each case their acids and esters, N-acylsulfonamides, N-acylsulfamoyl-benzamides, in each case, if appropriate, also in salt form and in each case optionally substituted 1-phenylpyrazoline, 1-phenylpyrazole, 1-phenyl-triazole, 5-phenylisoxazoline and 5-phenylmethylisoxazoline-3-carboxylic esters and 2-(8-quinolinyloxy)acetic acid derivatives.
Claims
exact text as granted — not AI-modified1 - 12 . (canceled)
13 . A herbicidally active composition comprising a mixture of
A a herbicidally active amount of one or more compounds of the formula (I) in which V is a radical selected from the group consisting of (V1) to (V4), where the symbols and indices have the following meanings: 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 is hydrogen, (C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 1 -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 )-halocycloalkyl, (C 1 -C 4 )-alkylthio(C 3 -C 8 )-cycloalkyl, (C 1 -C 8 )-haloalkyl or (C 2 -C 8 )-haloalkenyl; R 2 is hydrogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkyl, halogen, (C 1 -C 4 )-haloalkoxy, cyano, nitro; R 3 is 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, (C 1 -C 4 )-alkyl-substituted or unsubstituted arylsulfonyl, (C 1 -C 4 )-alkyl-substituted or unsubstituted arylcarbonyl-(C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkyl-substituted or unsubstituted aryl-(C 1 -C 4 )-alkyl; R 4 is hydrogen, (C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (CIC 4 )-haloalkyl, phenyl or benzyl; R 5 is (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, tetra hydropyran-3-yl, tetra hydrothiopyran-3-yl, 1-methylthiocyclopropyl, 2-ethylthiopropyl or two radicals R 5 together are (C 2 -C 4 )-alkylene; R 6 is hydroxyl, (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 )-alkylsulfinyl or (C 1 -C 4 )-alkylsulfonyl; R 7 is (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 )-halocycloalkyl; R 8 is cyano, (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; I is an integer from 0 to 6, where if I≧2 the radicals R 5 can be identical or different from each other, and R 9 are identical or different nitro, amino, (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 )-alkylaminosulfonyl, (C 1 -C 4 )-dialkylaminosulfonyl, (C 1 -C 4 )-alkylcarbamoyl, (C 1 -C 4 )-dialkylcarbamoyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, phenoxy, cyano, aryl, alkylamino or dialkylamino; q is 0, 1, 2, 3 or 4; and B an antidote-effective amount of one or more safeners selected from the group consisting of a) compounds of the formulae (II) to (IV), where the symbols and indices have the following meanings: n′ is a natural number from 0 to 5; 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 by [(C 1 -C 3 )-alkoxy]carbonyl; W is an unsubstituted or substituted divalent radical selected from the group consisting of (W1) to (W4), m′ is 0 or 1; R 17 , R 19 are identical or different halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, nitro or (C 1 -C 4 )-haloalkyl; R 18 , R 20 are identical or different OR 24 , SR 24 or NR 24 R 25 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 hetero atoms, which is linked to the carbonyl group in (II) or (III) via the N atom and is unsubstituted or substituted by radicals selected from the group consisting of (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy or optionally substituted phenyl;
R 24 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical;
R 25 is hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy or substituted or unsubstituted phenyl;
R 26 is 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 21 , R 29 are identical or different hydrogen, (C 1 -C 8 )-alkyl, (C 1 -C 8 )-haloalkyl, (C 3 -C 12 )-cycloalkyl or substituted or unsubstituted phenyl;
R 21 is (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 identical or different 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;
b) one or more compounds from the group consisting of:
1,8-naphthalic anhydride, methyl diphenylmethoxyacetate, cyanomethoxyimino(phenyl)acetonitrile (cyometrinil), 1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile (oxabetrinil), 4′-chloro-2,2,2-trifluoroacetophenone O-1,3-dioxolan-2-ylmethyloxime(fluxofenim), 4,6-dichloro-2-phenylpyrimidine (fenclorim), 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(dymrone), 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-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 (lactidichlor) and their salts and esters;
c) N-acylsulfonamides of the formula (V) and their salts
in which
R 30 is hydrogen, a hydrocarbon radical, a hydrocarbon-oxy radical, a hydrocarbon-thio radical or a heterocyclyl radical, it being possible for each of the 4 last-mentioned radicals being unsubstituted or being substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, carboxamide, sulfonamide and radicals of the formula Z a —R a ;
R 31 is hydrogen or (C 1 -C 4 )-alkyl, or
R 30 and R 31 together with the group of the formula —CO—N— are the residue of a 3- to 8-membered saturated or unsaturated ring;
R 32 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, CONH 2 , SO 2 NH 2 or a radical of the formula Z b —R b ;
R 33 is hydrogen or (C 1 -C 4 )-alkyl;
R 34 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH 2 , SO 2 NH 2 or a radical of the formula Z c —R c ;
R a is a hydrocarbon radical or a heterocyclyl radical, each of the two last-mentioned radicals being unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, mono- and di-[(C 1 -C 4 )-alkyl]amino, or an alkyl radical in which a plurality of non-adjacent CH 2 groups are in each case replaced by one oxygen atom;
R b , R c are identical or different and are a hydrocarbon radical or a heterocyclyl radical, each of the two last-mentioned radicals being unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, phosphoryl, halo-(C 1 -C 4 )-alkoxy, mono- and di-[(C 1 -C 4 )alkyl]amino, or an alkyl radical in which a plurality of nonadjacent CH 2 groups are replaced in each case by one 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 , the bond given on the right-hand side of each of the divalent groups being the bond to the radical Ra, and the radicals R* in the 5 last-mentioned radicals independently of each other being in each case H, (C 1 -C 4 )-alkyl or halo(C 1 -C 4 )-alkyl;
Z b , Z c independently of one another are 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, where, in asymmetrical divalent groups, the atom on the right-hand side is linked to the radical Rb or Rc and where the radicals R* in the 5 last-mentioned radicals independently of one another are in each case H, (C 1 -C 4 )-alkyl or halo-(C 1 -C 4 )-alkyl;
n is an integer from 0 to 4, and
t is an integer from 0 to 5.
d) Acylsulfamoylbenzamides of the formula (VI), optionally also in salt form,
in which
X 3 is CH or N;
R 35 is hydrogen, heterocyclyl or a hydrocarbon radical, the two last-mentioned radicals optionally being substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH 2 , SO 2 NH 2 and Z d —R d ;
R 36 is hydrogen, hydroxyl, (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 five last-mentioned radicals optionally being substituted by one or more identical or different radicals selected from the group consisting of halogen, hydroxyl, (C 1 -C 4 )alkyl, (C 1 -C 4 )-alkoxy and (C 1 -C 4 )-alkylthio, or
R 35 and R 36 together with the nitrogen atom to which they are attached are a 3- to 8-membered saturated or unsaturated ring;
R 37 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, 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 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, phosphoryl, CHO, CONH 2 , SO 2 NH 2 or Z f —R f ;
R d is a (C 2 -C 20 )-alkyl radical whose carbon chain is interrupted once or more than once by oxygen atoms, or is heterocyclyl or a hydrocarbon radical, the two last-mentioned radicals optionally being substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, mono- and di-[(C 1 -C 4 )-alkyl]amino;
R e , R f are identical or different and are a (C 2 -C 20 )-alkyl radical whose carbon chain is interrupted once or more than once by oxygen atoms, or a heterocyclyl or a hydrocarbon radical, the two last-mentioned radicals optionally being substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, phosphoryl, (C 1 -C 4 )-haloalkoxy, mono- and di-[(C 1 -C 4 )-alkyl]amino;
Z d is a divalent unit selected from the group consisting of 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 identical or different and are a direct bond or a divalent unit selected from the group consisting of 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 is an integer from 0 to 4, and
o in the event that X is CH, is an integer from 0 to 5 and, in the event that X is N, is an integer from 0 to 4;
inclusive of the stereoisomers and the agriculturally customary salts, with the exclusion of mixtures in which
a) in the compound of the formula (I), V=V1 or V4 and the safener has the formula (IV) or is selected from the group consisting of 1,8-naphthalic 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 0-1,3-dioxolan-2-ylmethyloxime, 4,6-dichloro-2-phenylpyrimidine, benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate and 1-methylhexyl (5-chloro-8-quinolinoxy)acetate; or
b) in the compound of the formula (I), V=V3 where R 6 =OH, and the safener
has the formula (II) where W=W1, W2, W3 or W4 where m′=1 or
has the formula (III) and 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
has the formula (IV), or
is a compound from the group consisting of 1,8-naphthalic anhydride, cyanomethoxyimino(phenyl)acetonitrile, oxabetrinil, fluxofenim and flurazole.
14 . A herbicidally active composition as claimed in claim 13 where, in the compound of the formula (I),
V is a radical selected from the group consisting of (V1) to (V4) 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 is hydrogen; R 3 is hydrogen, (C 1 -C 4 alkyl, (C 1 -C 4 )-alkyl-substituted arylsulfonyl, (C 1 -C 4 alkyl-arylcarbonylmethyl, benzyl; R 4 is (C 1 -C 4 )-alkyl; R 5 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, or two radicals R 5 are C 2 -alkenyl; R 6 is hydroxyl, (C 1 -C 4 )-alkoxy, phenylthio; R 7 is (C 3 -C 7 )-cycloalkyl; R 8 is cyano; I is an integer from 0 to 3, where, if 1≧2, the radicals R 5 can be identical or different from each other, and R 9 are identical or different (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 )-alkoxycarbonyl; q is 0,1,2, 3 or 4.
15 . A herbicidally active composition as claimed in claim 13 , which comprises safeners of the formula (II) and/or (III) where the symbols and indices have the following meanings:
R 18 , R 20 are OR 24 ; R 24 is hydrogen, (C 1 -C 18 )alkyl, (C 3 -C 12 )-cycloalkyl, (C 2 -C 8 )-alkenyl and (C 2 -C 18 )alkynyl, it being possible for the carbon-containing groups to be sutstituted by one or more radicals R 50 ; R 50 is identical or different halogen, hydroxyl, (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, carboxyl, (C 1 -C 8 )-alkoxycarbonyl, (C 2 -C 8 )-alkenyloxycarbonyl, (C 1 -C 8 )-alkylthiocarbonyl, (C 2 -C 8 )-alkynylcarbonyl, (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 2-6 )alkynylaminocarbonyl, (C 1 -C 8 ) alkoxycarbonylamino, (C 1 -C 8 )alkylaminocarbonylamino, (C 1 -C 6 )-alkylcarbonyloxy which is unsubstituted or substituted by R 51 , or is (C 2 -C 6 )-alkenylcarbonyloxy, (C 2 -C 6 )-alkynylcarbonyloxy, (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 9 last-mentioned radicals being unsubstituted in the phenyl ring or mono- or polysubstituted by radicals R 52 , SiR′ 3 , O—SiR′ 3 , R′ 3 Si—(C 1 -C 8 )alkoxy, CO—O—NR 12 , ON═CR′ 2 , N═CR′ 2 , ONR′ 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 is identical or different halogen, nitro, (C 1 -C 4 alkoxy and phenyl which is unsubsituted or substituted by one or more radicals R 52 ; R 52 is identical or different halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )haloalkoxy or nitro; R′ is identical or different hydrogen, (C 1 -C 4 )-alkyl, phenyl which is unsubstituted or substituted by one or more radicals R 52 , or two radicals R′ together form a (C 2 -C 6 )alkanediyl chain; R″ is identical or different (C 1 -C 4 )-alkyl or two radicals R″ together form a (C 2 -C 6 )-alkanediyl chain; R′″ is hydrogen or (C 1 -C 4 )-alkyl; w is 0, 1, 2,3,4, 5 or 6.
16 . A herbicidally active composition as claimed in claim 13 which comprises safeners of the formula (V) or their salts, where
R 30 is hydrogen, (C 1 -C 6 )alkyl, (C 3 -C 6 )-cycloalkyl, furanyl or thienyl, each of the 4 last-mentioned radicals being unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C 1 -C 4 )-alkoxy, halo-(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 is hydrogen; R 32 is halogen, halo-(C 1 -C 4 )-alkyl, halo-(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; R 33 is hydrogen; R 34 is halogen, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 alkyl, halo-(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; n is 0, 1 or 2 and t is 1 or 2.
17 . A herbicidally active composition as claimed in claim 13 which comprises safeners of the formula (VI) in which
X 3 is CH R 35 is hydrogen, (C 1 -C 6 )alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 5 -C 6 )-cycloalkenyl, phenyl or 3- to 6-memered heterocyclyl having up to three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, the six last-mentioned radicals optionally being substituted by one or more identical or different substituents selected from the group consisting of 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 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 alkinyl, the three last-mentioned radicals optionally being substituted by one or more identical or different substituents selected from the group consisting of halogen, hydroxyl, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy and (C 1 -C 4 )-alkylthio; R 37 is identical or different halogen, (C 1 -C 4 )-haloalkyl, (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 is hydrogen; R 39 is identical or different halogen, nitro, (C 1 -C 4 )-alkyl; (C 1-4 )-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 is 0, 1 or 2 and o is 1 or 2.
18 . A herbicidally active composition as claimed in claim 13 , in which the weight ratio of herbicide:safener is 1:100 to 100:1.
19 . A herbicidally active composition as claimed in claim 13 which additionally comprises a further herbicide.
20 . A herbicidally active composition as claimed in claim 19 , wherein the further herbicide is sulfonylurea.
21 . A method of controlling harmful plants in crops of useful plants, which comprises applying a herbicidally active amount of a herbicidally active composition as claimed in claim 13 to the harmful plants, the crop plants, the seeds of the plants or the area on which the plants grow.
22 . The method as claimed in claim 21 , wherein the plants belong to the group consisting of maize, wheat, rye, barley, oats, rice, sorghum, cotton and soya.
23 . The method as claimed in claim 21 , wherein the plants are genetically altered plants.
24 . The herbicidally active composition as claimed in claim 13 where, in the compound of formula (I), V is V1.
25 . The herbicidally active composition as claimed in claim 13 where, in the compound of formula (I), V is V 1 , R 1 is H, R 1 is cyclopropyl, and (R 9 ) q is 2-SO 2 Me-4-CF 3 .
26 . The herbicidally active composition as claimed in claim 13 , wherein the safener is of formula (II) and W is W4.
27 . The herbicidally active composition as claimed in claim 13 , wherein the safener is ethyl 5,5,-diphenyl-2-isoxazoline-3-carboxylate.
28 . The herbicidally active composition as claimed in claim 13 , where, in the compound of formula (I), V is V1, and wherein the safener is of formula (II) and W is W4.
29 . The herbicidally active composition as claimed in claim 13 , where, in the compound of formula (I), V is V 1 , R 1 is H, R 1 is cyclopropyl, and (R 9 ) q is 2-SO 2 Me-4-CF 3 , and wherein the safener is of formula (II) and W is W4.
30 . The herbicidally active composition as claimed in claim 13 , where, in the compound of formula (I), V is V1, and wherein the safener is ethyl 5,5,-diphenyl-2-isoxazoline-3-carboxylate.
31 . The herbicidally active composition as claimed in claim 13 , where, in the compound of formula (I), V is V 1 , R 1 is H, R 1 is cyclopropyl, and (R 9 ) q is 2-SO 2 Me-4-CF 3 , and wherein the safener is ethyl 5,5,-diphenyl-2-isoxazoline-3-carboxylate.
32 . A herbicidally active composition comprising a mixture of
A a herbicidally active amount of one or more compounds of the formula (I) in which V is a radical selected from the group consisting of (V1) to (V4), where the symbols and indices have the following meanings: 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 is hydrogen, (C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 1 -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 )-halocycloalkyl, (C 1 -C 4 )-alkylthio(C 3 -C 8 )-cycloalkyl, (C 1 -C 8 )-haloalkyl or (C 2 -C 8 )-haloalkenyl; R 2 is hydrogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkyl, halogen, (C 1 -C 4 )-haloalkoxy, cyano, nitro; R 3 is 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, (C 1 -C 4 )-alkyl-substituted or unsubstituted arylsulfonyl, (C 1 -C 4 )-alkyl-substituted or unsubstituted arylcarbonyl-(C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkyl-substituted or unsubstituted aryl-(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 is (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, tetra hydropyran-3-yl, tetra hydrothiopyran-3-yl, 1-methylthiocyclopropyl, 2-ethylthiopropyl or two radicals R 5 together are (C 2 -C 4 )-alkylene; R 6 is hydroxyl, (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 )-alkylsulfinyl or (C 1 -C 4 )-alkylsulfonyl; R 7 is (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 )-halocycloalkyl; R 8 is cyano, (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; I is an integer from 0 to 6, where if I≧2 the radicals R 5 can be identical or different from each other, and R 9 are identical or different nitro, amino, (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 )-alkylaminosulfonyl, (C 1 -C 4 )-dialkylaminosulfonyl, (C 1 -C 4 )-alkylcarbamoyl, (C 1 -C 4 )-dialkylcarbamoyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, phenoxy, cyano, aryl, alkylamino or dialkylamino; q is 0, 1, 2, 3 or 4; and B an antidote-effective amount of one or more safeners selected from the group consisting of a) compounds of the formulae (II) to (IV), where the symbols and indices have the following meanings: n′ is a natural number from 0 to 5; 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 by [(C 1 -C 3 )-alkoxy]carbonyl; W is an unsubstituted or substituted divalent heterocyclic radical selected from the group of the partially unsaturated or aromatic five-membered heterocyclic rings which have 1 to 3 hetero ring atoms of the N or O type, where the ring contains at least one N atom and not more than one O atom; b) one or more compounds from the group consisting of: 1,8-naphthalic anhydride, methyl diphenylmethoxyacetate, cyanomethoxyimino(phenyl)acetonitrile (cyometrinil), 1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile (oxabetrinil), 4′-chloro-2,2,2-trifluoroacetophenone 0-1,3-dioxolan-2-ylmethyloxime(fluxofenim), 4,6-dichloro-2-phenylpyrimidine (fenclorim), 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(dymrone), 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-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 (lactidichlor) and their salts and esters; c) N-acylsulfonamides of the formula (V) and their salts in which R 30 is hydrogen, a hydrocarbon radical, a hydrocarbon-oxy radical, a hydrocarbon-thio radical or a heterocyclyl radical, it being possible for each of the 4 last-mentioned radicals being unsubstituted or being substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, carboxamide, sulfonamide and radicals of the formula Z a —R a ; R 31 is hydrogen or (C 1 -C 4 )-alkyl, or R 30 and R 31 together with the group of the formula —CO—N— are the residue of a 3- to 8-membered saturated or unsaturated ring; R 32 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, CONH 2 , SO 2 NH 2 or a radical of the formula Z b —R b ; R 33 is hydrogen or (C 1 -C 4 )-alkyl; R 34 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH 2 , SO 2 NH 2 or a radical of the formula Z c —R c ; R a is a hydrocarbon radical or a heterocyclyl radical, each of the two last-mentioned radicals being unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, mono- and di-[(C 1 -C 4 )-alkyl]amino, or an alkyl radical in which a plurality of non-adjacent CH 2 groups are in each case replaced by one oxygen atom; R b , R c are identical or different and are a hydrocarbon radical or a heterocyclyl radical, each of the two last-mentioned radicals being unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, phosphoryl, halo-(C 1 -C 4 )-alkoxy, mono- and di-[(C 1 -C 4 )alkyl]amino, or an alkyl radical in which a plurality of nonadjacent CH 2 groups are replaced in each case by one 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 , the bond given on the right-hand side of each of the divalent groups being the bond to the radical R a , and the radicals R* in the 5 last-mentioned radicals independently of each other being in each case H, (C 1 -C 4 )-alkyl or halo(C 1 -C 4 )-alkyl; Z b , Z c independently of one another are 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, where, in asymmetrical divalent groups, the atom on the right-hand side is linked to the radical R b or R c and where the radicals R* in the 5 last-mentioned radicals independently of one another are in each case H, (C 1 -C 4 )-alkyl or halo-(C 1 -C 4 )-alkyl; n is an integer from 0 to 4, and t is an integer from 0 to 5. d) Acylsulfamoylbenzamides of the formula (VI), optionally also in salt form, in which X 3 is CH or N; R 35 is hydrogen, heterocyclyl or a hydrocarbon radical, the twvo last-mentioned radicals optionally being substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH 2 , SO 2 NH 2 and Z d —R s ; R 36 is hydrogen, hydroxyl, (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 five last-mentioned radicals optionally being substituted by one or more identical or different radicals selected from the group consisting of halogen, hydroxyl, (C 1 -C 4 )alkyl, (C 1 -C 4 )-alkoxy and (C 1 -C 4 )-alkylthio, or R 35 and R 36 together with the nitrogen atom to which they are attached are a 3- to 8-membered saturated or unsaturated ring; R 37 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, 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 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, phosphoryl, CHO, CONH 2 , SO 2 NH 2 or Z f —R f ; R d is a (C 2 -C 20 )-alkyl radical whose carbon chain is interrupted once or more than once by oxygen atoms, or is heterocyclyl or a hydrocarbon radical, the two last-mentioned radicals optionally being substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, mono- and di-[(C 1 -C 4 )-alkyl]amino; R e , R f are identical or different and are a (C 2 -C 20 )-alkyl radical whose carbon chain is interrupted once or more than once by oxygen atoms, or a heterocyclyl or a hydrocarbon radical, the two last-mentioned radicals optionally being substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, phosphoryl, (C 1 -C 4 )-haloalkoxy, mono- and di-[(C 1 -C 4 )-alkyl]amino; Z d is a divalent unit selected from the group consisting of 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 identical or different and are a direct bond or a divalent unit selected from the group consisting of 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 is an integer from 0 to 4, and o in the event that X is CH, is an integer from 0 to 5 and, in the event that X is N is an integer from 0 to 4; inclusive of the stereoisomers and the agriculturally customary salts, with the exclusion of mixtures in which a) in the compound of the formula (I), V=V1 or V4 and the safener has the formula (IV) or is selected from the group consisting of 1,8-naphthalic 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 0-1,3-dioxolan-2-ylmethyloxime, 4,6-dichloro-2-phenylpyrimidine, benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate and 1-methylhexyl (5-chloro-8-quinolinoxy)acetate; or c) in the compound of the formula (I), V=V3 where R 6 ═OH, and the safener
has the formula (II) where W=W1, W2, W3 or W4 where m′=1 or
has the formula (III) and 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
has the formula (IV), or
is a compound from the group consisting of 1,8-naphthalic anhydride, cyanomethoxyimino(phenyl)acetonitrile, oxabetrinil, fluxofenim and flurazole.
33 . A herbicidally active composition comprising a mixture of
A a herbicidally active amount of one or more compounds of the formula (I) in which V is a radical selected from the group consisting of (V1) and (V4), where the symbols and indices have the following meanings: 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 is hydrogen, (C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 1 -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 )-halocycloalkyl, (C 1 -C 4 )-alkylthio(C 3 -C 8 )-cycloalkyl, (C 1 -C 8 )-haloalkyl or (C 2 -C 8 )-haloalkenyl; R 7 is (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 )-halocycloalkyl; R 8 is cyano, (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; R 9 are identical or different nitro, amino, (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 )-alkylaminosulfonyl, (C 1 -C 4 )-dialkylaminosulfonyl, (C 1 -C 4 )-alkylcarbamoyl, (C 1 -C 4 )-dialkylcarbamoyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, phenoxy, cyano, aryl, alkylamino or dialkylamino; q is 0, 1, 2, 3 or 4; and B an antidote-effective amount of one or more safeners selected from the group consisting of a) compounds of the formulae (II) to (IV), where the symbols and indices have the following meanings: n′ is a natural number from 0 to 5; 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 by [(C 1 -C 3 )-alkoxy]carbonyl; W is an unsubstituted or substituted divalent radical selected from the group consisting of (W1) to (W4), m′ is 0 or 1; R 17 , R 19 are identical or different halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, nitro or (C 1 -C 4 )-haloalkyl; R 18 , R 20 are identical or different OR 24 , SR 24 or NR 24 R 25 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 hetero atoms, which is linked to the carbonyl group in (II) or (III) via the N atom and is unsubstituted or substituted by radicals selected from the group consisting of (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy or optionally substituted phenyl; R 24 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical; R 25 is hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy or substituted or unsubstituted phenyl; R 26 is 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 identical or different hydrogen, (C 1 -C 8 )-alkyl, (C 1 -C 8 )-haloalkyl, (C 3 -C 12 )-cycloalkyl or substituted or unsubstituted phenyl; R 21 is (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 identical or different 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; b) one or more compounds from the group consisting of: 1,8-naphthalic anhydride, methyl diphenylmethoxyacetate, cyanomethoxyimino(phenyl)acetonitrile (cyometrinil), 1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile (oxabetrinil), 4′-chloro-2,2,2-trifluoroacetophenone 0-1,3-dioxolan-2-ylmethyloxime(fluxofenim), 4,6-dichloro-2-phenylpyrimidine (fenclorim), 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(dymrone), 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-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 (lactidichlor) and their salts and esters; c) N-acylsulfonamides of the formula (V) and their salts in which R 30 is hydrogen, a hydrocarbon radical, a hydrocarbon-oxy radical, a hydrocarbon-thio radical or a heterocyclyl radical, it being possible for each of the 4 last-mentioned radicals being unsubstituted or being substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, carboxamide, sulfonamide and radicals of the formula Z a —R a ; R 31 is hydrogen or (C 1 -C 4 )-alkyl, or R 30 and R 31 together with the group of the formula —CO—N— are the residue of a 3- to 8-membered saturated or unsaturated ring; R 32 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, CONH 2 , SO 2 NH 2 or a radical of the formula Z b —R b ; R 33 is hydrogen or (C 1 -C 4 )-alkyl; R 34 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH 2 , SO 2 NH 2 or a radical of the formula Z c —R c ; R a is a hydrocarbon radical or a heterocyclyl radical, each of the two last-mentioned radicals being unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, mono- and di-[(C 1 -C 4 )-alkyl]amino, or an alkyl radical in which a plurality of non-adjacent CH 2 groups are in each case replaced by one oxygen atom; R b , R c are identical or different and are a hydrocarbon radical or a heterocyclyl radical, each of the two last-mentioned radicals being unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, phosphoryl, halo-(C 1 -C 4 )-alkoxy, mono- and di-[(C 1 -C 4 )alkyl]amino, or an alkyl radical in which a plurality of nonadjacent CH 2 groups are replaced in each case by one 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 , the bond given on the right-hand side of each of the divalent groups being the bond to the radical Ra, and the radicals R* in the 5 last-mentioned radicals independently of each other being in each case H, (C 1 -C 4 )-alkyl or halo(C 1 -C 4 )-alkyl; Z b , Z c independently of one another are 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, where, in asymmetrical divalent groups, the atom on the right-hand side is linked to the radical R b or R c and where the radicals R* in the 5 last-mentioned radicals independently of one another are in each case H, (C 1 -C 4 )-alkyl or halo-(C 1 -C 4 )-alkyl; n is an integer from 0 to 4, and t is an integer from 0 to 5. d) Acylsulfamoylbenzamides of the formula (VI), optionally also in salt form, in which X 3 is CH or N; R 35 is hydrogen, heterocyclyl or a hydrocarbon-radical, the two last-mentioned radicals optionally being substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH 2 , SO 2 NH 2 and Z d —R d ; R 36 is hydrogen, hydroxyl, (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 five last-mentioned radicals optionally being substituted by one or more identical or different radicals selected from the group consisting of halogen, hydroxyl, (C 1 -C 4 )alkyl, (C 1 -C 4 )-alkoxy and (C 1 -C 4 )-alkylthio, or R 35 and R 36 together with the nitrogen atom to which they are attached are a 3- to 8-membered saturated or unsaturated ring; R 37 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, 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 is identical or different halogen, cyano, nitro, amino, hydroxyl, carboxyl, phosphoryl, CHO, CONH 2 , SO 2 NH 2 or Z f —R f ; R d is a (C 2 -C 20 )-alkyl radical whose carbon chain is interrupted once or more than once by oxygen atoms, or is heterocyclyl or a hydrocarbon radical, the two last-mentioned radicals optionally being substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, mono- and di-[(C 1 -C 4 )-alkyl]amino; R e , R f are identical or different and are a (C 2 -C 20 )-alkyl radical whose carbon chain is interrupted once or more than once by oxygen atoms, or a heterocyclyl or a hydrocarbon radical, the two last-mentioned radicals optionally being substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, phosphoryl, (C 1 -C 4 )-haloalkoxy, mono- and di-[(C 1 -C 4 )-alkyl]amino; Z d is a divalent unit selected from the group consisting of 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 identical or different and are a direct bond or a divalent unit selected from the group consisting of 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 is an integer from 0 to 4, and o in the event that X is CH, is an integer from 0 to 5 and, in the event that X is N, is an integer from 0 to 4; inclusive of the stereoisomers and the agriculturally customary salts, with the exclusion of mixtures in which in the compound of the formula (I), V=V1 or V4 and the safener has the formula (IV) or is selected from the group consisting of 1,8-naphthalic 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 0-1,3-dioxolan-2-ylmethyloxime, 4,6-dichloro-2-phenylpyrimidine, benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate and 1-methylhexyl (5-chloro-8-quinolinoxy)acetate; or
34 . A composition as claimed in claim 33 , wherein
V is a radical selected from the group consisting of (V1) and (V4): 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 7 is (C 3 -C 7 )-cycloalkyl; R 8 is cyano; R 9 are identical or different (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; and q is 0, 1, 2, 3 or 4.
35 . The composition as claimed in claim 33 , comprising safeners of the formula (II), where the symbols and indices have the following meanings:
R 18 is OR 24 ; R 24 is hydrogen, (C 1 -C 18 )alkyl, (C 3 -C 12 )cycloalkyl, (C 2 -C 8 )-alkenyl and (C 2 -C 18 )alkynyl, it being possible for the carbon-containing groups to be substituted by one or more radicals R 50 ; R 50 is identical or different halogen, hydroxyl, (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, carboxyl, (C 1 -C 8 )-alkoxycarbonyl, (C 2 -C 8 )-alkenyloxycarbonyl, (C 1 -C 8 )-alkylthiocarbonyl, (C 2 -C 8 )-alkynylcarbonyl, (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 , or is (C 2 -C 6 )-alkenylcarbonyloxy, (C 2 -C 6 )-alkynylcarbonyloxy, (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 9 last-mentioned radicals being unsubstituted in the phenyl ring or mono- or polysubstituted by radicals R 52 , SiR′ 13 , O—SiR′ 3 , R′ 3 Si—(C 1 -C 8 )-alkoxy, CO—O—NR′ 2 , ON═CR′ 2 , N═CR′ 2 , ONR′ 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 is identical or different halogen, nitro, (C 1 -C 4 )-alkoxy and phenyl which is unsubsituted or substituted by one or more radicals R 52 ; R 52 is identical or different halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-haloalkoxy or nitro; R′ is identical or different hydrogen, (C 1 -C 4 )-alkyl, phenyl which is unsubstituted or substituted by one or more radicals R 52 , or two radicals R′ together form a (C 2 -C 6 )-alkanediyl chain; R″ is identical or different (C 1 -C 4 )-alkyl or two radicals R″ together form a (C 2 -C 6 )alkanediyl chain; R′″ is hydrogen or (C 1 -C 4 )-alkyl; w is 0, 1, 2,3,4, 5 or 6.
36 . The composition as claimed in claim 33 , comprising safeners of the formula (II), where the symbols and indices have the following meanings:
R 18 is OR 24 ; and R 24 is hydrogen.
37 . The composition as claimed in claim 33 , comprising safeners of the formula (II), where the symbols and indices have the following meanings:
W is a group of the formula W4: m′ is 0 or 1; R 17 is halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, nitro or (C 1 -C 4 )-haloalkyl; R″ is OR 24 ; R 50 is identical or different halogen, hydroxyl, (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, carboxyl, (C 1 -C 8 )-alkoxycarbonyl, (C 2 -C 8 )-alkenyloxycarbonyl, (C 1 -C 8 )-alkylthiocarbonyl, (C 2 -C 8 )-alkynylcarbonyl, (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 , or is (C 2 -C 6 )-alkenylcarbonyloxy, (C 2 -C 6 )-alkynylcarbonyloxy, (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 9 last-mentioned radicals being unsubstituted in the phenyl ring or mono- or polysubstituted by radicals R 52 , SiR′ 3 , O—SiR′ 3 , R′ 3 Si—(C 1 -C 8 )-alkoxy, CO—O—NR 12 , ON═CR′ 2 , N═CR′ 2 , ONR′ 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 is identical or different halogen, nitro, (C 1 -C 4 )-alkoxy and phenyl which is unsubsituted or substituted by one or more radicals R 52 ; R 52 is identical or different halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-haloalkoxy or nitro; R′ is identical or different hydrogen, (C 1 -C 4 )-alkyl, phenyl which is unsubstituted or substituted by one or more radicals R 52 , or two radicals R′ together form a (C 2 -C 6 )-alkanediyl chain; R″ is identical or different (C 1 -C 4 )-alkyl or two radicals R″ together form a (C 2 -C 6 )-alkanediyl chain; R′″ is hydrogen or (C 1 -C 4 )-alkyl; and w is 0, 1, 2,3,4, 5 or 6.
38 . The composition as claimed in claim 37 , comprising safeners of the formula (II), where the symbol and indices have the following meanings:
R 18 is OR 24 ; and R 24 is hydrogen.
39 . The composition as claimed in claim 37 , wherein the safener of the formula (II) is ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylic acid.
40 . The composition as claimed in claim 37 , wherein the safener of the formula (II) is 5,5-diphenyl-2-isoxazoline-3-carboxylic acid.
41 . The composition as claimed in claim 37 , comprising a compound of the formula (I), in which V is a radical of the formula (V1), wherein the symbols and indices have the following meaning:
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 is hydrogen, (C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 1 -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 )-halocycloalkyl, (C 1 -C 4 )-alkylthio(C 3 -C 8 )-cycloalkyl, (C 1 -C 8 )-haloalkyl or (C 2 -C 8 )-haloalkenyl; R 9 are identical or different nitro, amino, (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 )-alkylaminosulfonyl, (C 1 -C 4 )-dialkylaminosulfonyl, (C 1 -C 4 )-alkylcarbamoyl, (C 1 -C 4 )-dialkylcarbamoyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, phenoxy, cyano, aryl, alkylamino or dialkylamino; and q is 0, 1, 2, 3 or 4.
42 . The composition as claimed in claim 39 , comprising a compound of the formula (I), in which V is a radical of the formula (V1), wherein the symbols and indices have the following meaning:
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 is hydrogen, (C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 1 -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 )-halocycloalkyl, (C 1 -C 4 )-alkylthio(C 3 -C 8 )-cycloalkyl, (C 1 -C 8 )-haloalkyl or (C 2 -C 8 )-haloalkenyl; R 9 are identical or different nitro, amino, (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 )-alkylaminosulfonyl, (C 1 -C 4 )-dialkylaminosulfonyl, (C 1 -C 4 )-alkylcarbamoyl, (C 1 -C 4 )-dialkylcarbamoyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, phenoxy, cyano, aryl, alkylamino or dialkylamino; and q is 0, 1, 2, 3 or 4.
43 . The composition as claimed in claim 37 , comprising a compound of the formula (I) which is 5-cyclopropyl-4-(2-methylsulphonyl-4-trifluoromethylbenzoyl)isoxazole.
44 . The composition as claimed in claim 38 , comprising a compound of the formula (I) which is 5-cyclopropyl-4-(2-methylsulphonyl-4-trifluoromethylbenzoyl)isoxazole.
45 . The composition as claimed in claim 39 , comprising a compound of the formula (I) which is 5-cyclopropyl-4-(2-methylsulphonyl-4-trifluoromethylbenzoyl)isoxazole.
46 . The composition as claimed in claim 40 , comprising a compound of the formula (I) which is 5-cyclopropyl-4-(2-methylsulphonyl-4-trifluoromethylbenzoyl)isoxazole.
47 . A herbicidally active composition comprising a mixture of a herbicidally active amount of the compound 5-cyclopropyl-4-(2-methylsulphonyl-4-trifluoromethylbenzoyl)isoxazole and an antidote-effective amount of one or more safeners selected from the group consisting of ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate and 5,5-dipenyl-2-isoxazoline-3-carboxylic acid.
48 . The herbicidally active composition as claimed in claim 47 , wherein the safener is 5,5-diphenyl-2-isoxazoline-3-carboxylate.
49 . The herbidically active composition as claimed in claim 47 , wherein the weight ratio of herbicide to safener is 1:100 to 100:1.
50 . A method of controlling harmful plants in crops of useful plants, which comprises applying a herbicidally active amount of a herbicidally active composition as claimed in claim 33 to the harmful plants, the crop plants, the seeds of the plants or the area on which the plants grow.
51 . The method as claimed in claim 50 , wherein the plants are selected from the group consisting of maize, wheat, rye, barley, oats, rice, sorghum, cotton and soya.
52 . The method as claimed in claim 50 , wherein the plants are maize plants.
53 . The method as claimed in claim 50 , comprising safeners of the formula (II), where the symbols and indices have the following meanings:
W is a group of the formula W4: m′ is 0 or 1; R 17 is halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, nitro or (C 1 -C 4 )-haloalkyl; R 18 is OR 24 ; R 50 is identical or different halogen, hydroxyl, (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, carboxyl, (C 1 -C 8 )-alkoxycarbonyl, (C 2 -C 8 )-alkenyloxycarbonyl, (C 1 -C 8 )-alkylthiocarbonyl, (C 2-8 )-alkynylcarbonyl, (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 , or is (C 2 -C 6 )-alkenylcarbonyloxy, (C 2 -C 6 )-alkynylcarbonyloxy, (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 9 last-mentioned radicals being unsubstituted in the phenyl ring or mono- or polysubstituted by radicals R 52 , SiR′ 3 , O—SiR′ 3 , R′ 3 Si—(C 1 -C 8 )-alkoxy, CO—O—NR 12 , ON═CR′ 2 , N═CR′ 2 , ONR′ 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 is identical or different halogen, nitro, (C 1 -C 4 )-alkoxy and phenyl which is unsubsituted or substituted by one or more radicals R 52 ; R 52 is identical or different halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 )-haloalkoxy or nitro; R′ is identical or different hydrogen, (C 1 -C 4 )-alkyl, phenyl which is unsubstituted or substituted by one or more radicals R 52 , or two radicals R′ together form a (C 2 -C 6 )alkanediyl chain; R″ is identical or different (C 1 -C 4 )-alkyl or two radicals R″ together form a (C 2 -C 6 )-alkanediyl chain; R′″ is hydrogen or (C 1 -C 4 )-alkyl; and w is 0, 1, 2,3,4, 5 or 6.
54 . The method as claimed in claim 53 , wherein:
R 18 is OR 24 ; and R 24 is hydrogen.
55 . The method as claimed in claim 53 , comprising a safener which is ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid.
56 . The method as claimed in claim 55 , which comprises the herbicide 5-cyclopropyl-4-(2-methylsulphonyl-4-trifluoromethylbenzoyl)isoxazole.
57 . The method as claimed in claim 56 , comprising a safener which is ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate.
58 . The method as claimed in claim 56 , wherein the weight ratio of herbicide to safener is 1:100 to 100:1.
59 . The method as claimed in claim 56 , wherein the plants are selected from the group consisting of maize, wheat, rye, barley, oats, rice, sorghum, cotton and soya.
60 . The method as claimed in claim 56 , wherein the plants are maize plants.
61 . A selective herbicidal composition comprising, in addition to customary inert formulation assistants, a mixture of
a) a herbicidally effective amount of a compound of formula I wherein Q is the group R 1 is hydrogen, —COO—C 1 -C 4 -alkyl, —S—C 1 -C 4 -alkyl or —SO—C 1 -C 4 -alkyl; and b) to antagonise the herbicide, an antidotally effective amount of a safener comprising the ethyl esters of the compound of formula II
62 . A method of selectively controlling weeds and grasses in crops of cultivated plants, which comprises treating said cultivated plants, the seeds or seedlings or the crop area thereof, concurrently or separately, with a herbicidally effective amount of the compound of formula I according to claim 50 and, to antagonise the herbicide, an antidotally effective amount of the safener of formula II according to claim 61 .
63 . The method according to claim 62 , wherein the cultivated plants are maize.
64 . A selective herbicidal composition comprising, in addition to customary inert formulation assistants, a mixture of
a) a herbicidally effective amount of a compound of formula I wherein Q is the group b) to antagonise the herbicide, an antidotally effective amount of a safener comprising the ethyl esters of the compound of formula II
65 . A method of selectively controlling weeds and grasses in crops of cultivated plants, which comprises treating said cultivated plants, the seeds or seedlings or the crop area thereof, concurrently or separately, with a herbicidally effective amount of the compound of formula I according to claim 64 and, to antagonise the herbicide, an antidotally effective amount of the safener of formula II according to claim 64 .
66 . The method according to claim 65 , wherein the cultivated plants are maize.
67 . A selective herbicidal composition comprising, in addition to customary inert formulation assistants, a mixture of
a) a herbicidally effective amount of a compound of formula I 1. wherein Q is the group b) to antagonise the herbicide, an antidotally effective amount of a safener comprising the ethyl esters of the compound of formula II
68 . A method of selectively controlling weeds and grasses in crops of cultivated plants, which comprises treating said cultivated plants, the seeds or seedlings or the crop area thereof, concurrently or separately, with a herbicidally effective amount of the compound of formula I according to claim 67 and, to antagonise the herbicide, an antidotally effective amount of the safener of formula II according to claim 67 .
69 . The method according to claim 68 , wherein the cultivated plants are maize.Cited by (0)
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