2-(3-alkylthiobenzoyl)cyclohexanediones and their use as herbicides
View Patent ↗2-(3-Alkylthiobenzoyl)cyclohexanediones of the formula (I) are described as herbicides. In this formula (I), X, Y, R 1 to R 8 represent radicals such as hydrogen, organic radicals such as alkyl and alkoxy.
1. A 2-(3-alkylthiobenzoyl)cyclohexanedione of formula (I) and/or a salt thereof
in which
R 1 is (C 1 -C 6 )-alkyl,
R 2 is hydroxyl, SR 13 , or NR 14 R 15 ,
R 3 and R 8 independently of one another are hydrogen or (C 1 -C 4 )-alkyl, or the radicals R 3 and R 8 together form the unit Z which represents an oxygen or sulfur atom or one to four methylene groups,
R 4 and R 7 independently of one another are hydrogen or (C 1 -C 4 )-alkyl,
R 5 and R 6 independently of one another are hydrogen or (C 1 -C 4 )-alkyl or together with the carbon atom to which they are attached form a carbonyl group,
X is OR 9 , OCOR 9 , or OSO 2 R 10 ,
R 9 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl or phenyl-(C 1 -C 6 )-alkyl, where the six last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen, OR 11 and S(O) m R 12 ,
R 10 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl or phenyl-(C 1 -C 6 )-alkyl, where the six last-mentioned radicals are substituted by s radicals selected from the group consisting of halogen, OR 11 and S(O) m R 12 ,
R 11 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
R 12 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
R 13 is (C 1 -C 4 )-alkyl, phenyl which is substituted by s radicals selected from the group consisting of nitro, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy or (C 1 -C 4 )-haloalkoxy or is partially or fully halogenated phenyl,
R 14 is hydrogen, (C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkoxy,
R 15 is hydrogen or (C 1 -C 4 )-alkyl,
or
R 14 and R 15 together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated, partially saturated or unsaturated ring,
which contains zero, one or two heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen,
which is substituted by s radicals from the group consisting of cyano, halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy and (C 1 -C 4 )-haloalkoxy,
Y is (C 1 -C 6 )-haloalkyl,
m is 0, 1 or 2,
n is 0, 1 or 2,
s is 0, 1, 2 or 3.
2. The 2-(3-alkylthiobenzoyl)cyclohexanedione and/or salt as claimed in claim 1 in which
R 1 is methyl, ethyl, n-propyl or isopropyl,
R 2 is hydroxyl,
R 3 and R 8 independently of one another are hydrogen or (C 1 -C 4 )-alkyl, or the radicals R 3 and R 8 together form a methylene or ethylene group,
R 4 and R 7 independently of one another are hydrogen, methyl or ethyl,
R 5 and R 6 independently of one another are hydrogen, methyl or ethyl,
X is OR 9 , OCOR 9 , or OSO 2 R 10 ,
R 9 is cyclopropylmethyl or (C 1 -C 6 )-alkyl substituted by s methoxy or ethoxy groups,
R 10 is (C 1 -C 6 )-alkyl substituted by s methoxy or ethoxy groups,
Y is (C 1 -C 3 )-haloalkyl,
n is 0, 1 or 2,
s is 0, 1, 2 or 3.
3. The 2-(3-alkylthiobenzoyl)cyclohexanedione and/or salt as claimed in claim 1 in which
R 1 is methyl, ethyl, n-propyl or isopropyl,
R 2 is hydroxyl,
R 3 and R 8 independently of one another are hydrogen, methyl or ethyl,
or the radicals R 3 and R 8 together form a methylene or ethylene group,
R 4 and R 7 independently of one another are hydrogen, methyl or ethyl,
R 5 and R 6 independently of one another are hydrogen, methyl or ethyl,
X is OR 9 ,
R 9 is cyclopropylmethyl or ethyl or methyl substituted by s methoxy or ethoxy groups,
Y is trichloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl or heptafluoroisopropyl,
n is 0, 1 or 2,
s is 0, 1, 2 or 3.
4. A herbicidal composition which comprises a herbicidally effective amount of at least one compound as claimed in claim 1 .
5. The herbicidal composition as claimed in claim 4 comprising a mixture with at least one formulation auxiliary.
6. 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 site of unwanted vegetation.
7. A herbicidal composition as claimed in claim 4 for controlling unwanted plants.
8. A composition as claimed in claim 7 wherein the compound of formula (I) and/or salt thereof is capable of controlling unwanted plants in crops of useful plants.
9. A composition as claimed in claim 8 wherein the useful plants are transgenic useful plants.