(4-haloalkyl-3-thiobenzoyl)cyclohexanediones and use thereof as herbicides
View Patent ↗A description is given of (4-haloalkyl-3-thiobenzoyl)cyclohexanediones of the formula (I) and of their use as herbicides. In this formula (I), X, Y, R 1 , R 2 , R 3 , and R 4 are radicals such as hydrogen and organic radicals such as alkyl. A and Z are oxygen or alkylene.
1. A (4-haloalkyl-3-thiobenzoyl)cyclohexanedione of formula (I) and/or salt thereof
in which
X is (C 1 -C 4 )-alkyl,
Y is (C 1 -C 4 )-haloalkyl,
A and Z independently of one another are oxygen, —S(O) m —, —N(R 5 )—, carbonyl or (C 1 -C 4 )-alkylene which is interrupted by q units from the group consisting of oxygen, —S(O) m —, —N(R 5 )— and carbonyl, and which is substituted by s radicals R 6 ,
R 1 is (C 1 -C 4 )-alkyl,
R 2 is hydroxyl, SR′, NR 8 R 9 ,
R 3 and R 4 are independently of one another hydrogen or (C 1 -C 4 )-alkyl,
R 5 is hydrogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylcarbonyl, (C 1 -C 4 )-alkoxycarbonyl, phenylcarbonyl or phenoxycarbonyl, the phenyl ring in the two last-mentioned radicals being substituted by p halogen atoms and by p radicals from the group consisting of nitro, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, and (C 1 -C 4 )-haloalkoxy,
R 6 is halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy or (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl,
R 7 is (C 1 -C 4 )-alkyl or is phenyl which is substituted by p halogen atoms or by p radicals from the group consisting of nitro, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, and (C 1 -C 4 )-haloalkoxy,
R 8 is hydrogen, (C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkoxy,
R 9 is hydrogen or (C 1 -C 4 )-alkyl,
or
R 8 and R 9 , with the nitrogen atom to which they are attached, form a 5- or 6-membered saturated, partially saturated or fully unsaturated ring which contains m further heteroatoms from the group consisting of oxygen, sulfur, and nitrogen, and which is substituted by s halogen atoms and by p radicals from the group consisting of cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, and (C 1 -C 4 )-haloalkoxy,
m and n independently of one another are 0, 1 or 2,
p is 0, 1, 2, 3, 4 or 5,
q is 0 or 1, and
s is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
with the proviso that Y excludes trifluoromethyl.
2. A (4-haloalkyl-3-thiobenzoyl)cyclohexanedione and/or salt as claimed in claim 1 , in which
X is (C 1 -C 4 )-alkyl,
Y is (C 1 -C 4 )-haloalkyl,
A and Z are independently of one another oxygen or (C 1 -C 4 )-alkylene,
R 1 is (C 1 -C 4 )-alkyl,
R 2 is hydroxyl, and
R 3 and R 4 are independently of one another hydrogen or (C 1 -C 4 )-alkyl,
with the proviso that Y excludes trifluoromethyl.
3. A (4-haloalkyl-3-thiobenzoyl)cyclohexanedione and/or salt as claimed in claim 1 , in which
X is (C 1 -C 4 )-alkyl,
Y is trichloromethyl, difluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, pentafluoroethyl or heptafluoroisopropyl,
A and Z are each (C 1 -C 4 )-alkylene,
R 1 is (C 1 -C 4 )-alkyl,
R 2 is hydroxyl, and
R 3 and R 4 are independently of one another hydrogen or (C 1 -C 4 )-alkyl.
4. A (4-haloalkyl-3-thiobenzoyl)cyclohexanedione and/or salt as claimed in claim 1 , in which
X is methyl,
Y is chlorodifluoromethyl, difluoromethyl or pentafluoroethyl,
A and Z are independently of one another each CH 2 or CH 2 CH 2 ,
R 1 is methyl,
R 2 is hydroxyl,
R 3 and R 4 are each hydrogen, and
n is 1 or 2.
5. A (4-haloalkyl-3-thiobenzoyl)cyclohexanedione and/or salt as claimed in claim 1 , in which
X is methyl,
Y is pentafluoroethyl,
A and Z are independently of one another each CH 2 or CH 2 CH 2 ,
R 1 is methyl,
R 2 is hydroxyl,
R 3 and R 4 are each hydrogen, and
n is 1 or 2.
6. A herbicidal composition which comprises a herbicidally effective amount of at least one compound as claimed in claim 1 .
7. The herbicidal composition as claimed in claim 6 in a mixture with at least one formulation auxiliary.
8. The herbicidal composition as claimed in claim 6 , comprising at least one further pesticidally active compound from the group of insecticides, acaricides, herbicides, fungicides, safeners, and growth regulators.
9. The herbicidal composition as claimed in claim 6 , comprising a safener.
10. The herbicidal composition as claimed in claim 6 , comprising a further herbicide.
11. A method for controlling unwanted plants, which comprises applying an effective amount of at least one compound as claimed in claim 1 to plants and/or to a location of unwanted plant growth.
12. A herbicidal composition as claimed in claim 6 suitable for controlling unwanted plants.
13. The composition as claimed in claim 12 , wherein the compound is capable of being used for controlling unwanted plants in crops of useful plants.
14. The composition as claimed in claim 13 , wherein the useful plants are transgenic useful plants.
15. The method according to claim 11 , wherein the compound is applied pre-sowing.
16. The method according to claim 11 , wherein the compound is applied pre-emergence.
17. The method according to claim 11 , wherein the compound is applied post-emergence.
18. The method according to claim 11 , wherein the compound is applied at a rate of 0.001 to 1.0 kg/ha.