Herbicides comprising benzoylcyclohexanediones and safeners
View Patent ↗Herbicidal compositions are described that comprise active substances from the group of the benzoylcyclohexanediones and also safeners. These herbicidal composition are especially suitable for use against weed plants in crop plant cultures.
1. A herbicidal composition comprising
A) a herbicidally effective amount of one or more compounds of the formula (I)
in which the symbols and indices have the following definitions:
R 1 is nitro, amino, halogen, cyano, (C 1 –C 4 )-alkyl, (C2–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 )-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, (C 1 –C 4 )-alkoxy, (C 1 –C 4 )-alkoxy-(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, (C 1 –C 4 )-alkylamino or (C 1 –C 4 )-dialkylamino;
R 2 is (C 1 –C 4 )-haloalkoxy-(C 1 –C 4 )-alkyl, (C 1 –C 4 )-alkoxy-(C 1 –C 4 )-alkoxy-(C 1 –C 4 )-alkoxy-(C 1 –C 4 )-alkyl, (C 3 –C 6 )-cycloalkoxy-(C 1 –C 4 )-alkyl, (C 3 –C 6 )-cycloalkyl-(C 1 –C 4 )-alkoxy, tetrahydrofuran-2-yl-methoxy-(C 1 –C 4 )-alkyl, tetrahydrofuran-3-yl-methoxy-(C 1 –C 4 )-alkyl or a heterocyclic radical from the group consisting of isoxazol-3-yl and 4,5-dihydroisoxazol-3-yl which is substituted by a radical from the group consisting of cyanomethyl, ethoxymethyl and methoxymethyl;
R 3 is OR 5 , cyano, halogen, cyanato, thiocyanato, (C 1 –C 4 )-alkylthio, (C 1 –C 4 )-alkylsulfinyl, (C 1 –C 4 )-alkylsulfonyl, (C 2 –C 4 )-alkenylthio, (C 2 –C 4 )-alkenylsulfinyl, (C 2 –C 4 )-alkenylsulfonyl, (C 2 –C 4 )-alkynylthio, (C 2 –C 4 )-alkynylsulfinyl, (C 2 –C 4 )-alkynylsulfonyl, (C 1 –C 4 )-haloalkylthio, (C 2 –C 4 )-haloalkenylthio, (C 2 –C 4 )-haloalkynylthio, (C 1 –C 4 )-haloalkylsulfinyl, (C 2 –C 4 )-haloalkenylsulfinyl, (C 2 –C 4 )-haloalkynylsulfinyl, (C 1 –C 4 )-haloalkylsulfonyl, (C 2 –C 4 )-haloalkenylsulfonyl or (C 2 –C 4 )-haloalkynylsulfonyl;
R 4 is (C 1 –C 4 )-alkyl;
R 5 is hydrogen, (C 1 –C 4 )-alkyl, (C 1 –C 4 )-haloalkyl or (C 1 –C 4 )-alkoxy-(C 1 –C 4 )-alkyl;
a is 0, 1, 2 or 3;
b is 0, 1 or 2; and
B) an antidote-active amount of one or more 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 a -R a ;
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 halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH 2 , SO 2 NH 2 or 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 is halogen, cyano, nitro, amino, hydroxyl, carboxyl, phosphoryl, CHO, CONH 2 , SO 2 NH 2 or Z c -R c ;
R a 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 b , R c 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 a is a divalent unit 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 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 d , SO 2 NR d or C(O)NR d ;
R d is hydrogen, (C 1 –C 4 )-alkyl or (C 1 –C 4 )-haloalkyl;
r is an integer from 0 to 4, and
q in the event that X 3 is CH, is an integer from 0 to 5 and, in the event that X 3 is N, is an integer from 0 to 4;
inclusive of the stereoisomers and the agriculturally customary salts.
2. The herbicidal composition as claimed in claim 1 , comprising compounds of the formula (I) wherein the symbols and indices have the following definitions:
R 1 is nitro, cyano, chlorine, fluorine, methyl, trifluoromethyl, methylsulfonyl or ethylsulfonyl;
R 2 is pentafluoroethoxymethyl, 2,2-difluoroethoxymethyl, 2,2,2-trifluoroethoxyinethyl, 2,2,3,3-tetrafluoropropoxymethyl, cyclopentyloxymethyl, cyclohexyloxymethyl, cyclopropyloxy, tetrahydrofuran-2-ylmethoxymethyl, methoxyethoxyethoxymethyl, or 4,5-dihydroisoxazol-3-yl which is substituted by a radical from the group consisting of cyanomethyl, ethoxymethyl and methoxymethyl;
R 3 is OR 5 ;
R 5 is hydrogen;
a is2;
b is 0, and the two radicals R 1 are in positions 2 and 4 of the phenyl ring.
3. The herbicidal composition as claimed in claim 1 , wherein the ratio of herbicide to safener is from 1:10 to 10:1.
4. The herbicidal composition as claimed in claim 1 , comprising a further herbicide.
5. The herbicidal composition according to claim 1 , wherein
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-membered heterocyclyl having up to three heteroatoms 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 )-alkynylsulfinyl, (C 1 –C 2 )- alkylsulfonyl, (C 3 –C 6 )-cycloalkyl, (C 1 –C 4 )-alkoxycarbonyl, (C 1 –C 6 )-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 )-alkynyl, 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 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 halogen, nitro, (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 ( 1 –C 4 )-alkylcarbonyl;
r is 0,1 or 2and
q is 1 or 2.
6. The herbicidal composition as claimed in claim 1 , comprising compounds of the formula (I) wherein the symbols and indices have the following definitions:
R 1 is nitro, cyano, chlorine, fluorine, methyl, trifluoromethyl, methylsulfonyl or ethylsulfonyl;
R 2 is pentafluoroethoxymethyl, 2,2-difluoroethoxymethyl, 2,2,2-trifluoroethoxymethyl, 2,2,3,3-tetrafluoropropoxymethyl, cyclopentyloxymethyl, cyclohexyloxymethyl, cyclopropyloxy, tetrahydrofuran-2-ylmethoxymethyl, methoxyethoxyethoxymethyl, or 4,5-dihydroisoxazol-3-yl which is substituted by a radical from the group consisting of cyanomethyl, ethoxymethyl and methoxymethyl;
R 3 is OR 5 ;
R 5 is hydrogen;
a is2;
b is 0, and the two radicals R 1 are in positions 2 and 4 of the phenyl ring;
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, or phenyl, the last five 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 6 )-alkylcarbonyl and phenyl;
R 36 is hydrogen, (C 1 –C 6 )-alkyl, (C 2 –C 6 )-alkenyl, (C 2 –C 6 )-alkynyl, 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 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 halogen, nitro, (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;
r is 0,1 or 2 and
q is 1 or 2.
7. The herbicidal composition as claimed in claim 1 , comprising compounds of the formula (I) wherein the symbols and indices have the following definitions:
R 1 is nitro, cyano, chlorine, fluorine, methyl, trifluoromethyl, methylsulfonyl or ethylsulfonyl;
R 2 is pentafluoroethoxymethyl, 2,2-difluoroethoxymethyl, 2,2,2-trifluoroethoxymethyl, 2,2,3,3-tetrafluoropropoxymethyl, cyclopentyloxymethyl, cyclohexyloxymethyl, cyclopropyloxy, tetrahydrofuran-2-ylmethoxymethyl, methoxyethoxyethoxymethyl, or 4,5-dihydroisoxazol-3-yl which is substituted by a radical from the group consisting of cyanomethyl, ethoxymethyl and methoxymethyl;
R 3 is OR 5 ;
R 5 is hydrogen;
a is2;
b is 0, and the two radicals R 1 are in positions 2 and 4 of the phenyl ring;
X 3 is CH;
R 35 is hydrogen, (C 1 –C 6 )-alkyl, (C 3 –C 6 )-cycloalkyl or phenyl, the last three 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 1 –C 4 )-alkoxycarbonyl, (C 1 –C 6 )-alkylcarbonyl and phenyl;
R 36 is hydrogen or (C 1 –C 6 )-alkyl which is optionally 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 halogen, (C 1 –C 4 )-haloalkyl, (C 1 –C 4 )-haloalkoxy, nitro, (C 1 –C 1 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 halogen, nitro, (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;
r is 0, 1 or 2and
q is 1 or 2.
8. The herbicidal composition of claim 1 , wherein the herbicidally effective amount of one or more compounds of the formula (I) is selected from the group consisting of:
9. The herbicidal composition of claim 8 , wherein the herbicidally effective amount of one or more compounds of the formula (I) is:
and the antidote-active amount of one or more acylsulfamoylbenzamides of the formula (VI, optionally also in salt form, is:
10. A method of controlling weed plants in crops which comprises applying a herbicidally active amount of a herbicidal composition as claimed in claim 1 to the weed plants, plants, seeds of plants, or the area on which the plants are growing.
11. The method as claimed in claim 10 , wherein the plants are from the group consisting of sugar cane, corn, wheat, rye, barley, oats, rice, sorghum, cotton, and soya.
12. The method as claimed in claim 10 , wherein the plants have been genetically modified.