Cycloalkylphenyl substituted cyclic ketoenols
View Patent ↗The invention relates to novel cycloalkylphenyl-substituted cyclic ketoenols of the formula (I) in which J, X, Y, m and CKE are as defined above, to processes and intermediates for their preparation and to their use as pesticides and/or herbicides. Moreover, the invention relates to selective herbicidal compositions comprising, firstly, the cycloalkylphenyl-substituted cyclic ketoenols and, secondly, a crop plant compatibility-improving compound. The invention furthermore relates to increasing the activity of crop protection compositions comprising compounds of the formula (I) by adding ammonium or phosphonium salts and, if appropriate, penetrants.
1. A compound of formula (XXVII)
in which
J represents cyclopropyl,
X represents hydrogen, alkyl, halogen, haloalkyl, alkoxy or haloalkoxy,
Y represents hydrogen, alkyl, haloalkyl, halogen, alkoxy or haloalkoxy,
m represents a number 1, 2 or 3,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen, and
Z represents a leaving group introduced by carboxylic acid-activating reagents, carbodiimides, phosphorylating agents, or halogenating agents.
2. A compound of formula (XXVII) according to claim 1 , in which
Z represents a leaving group introduced by carbonyldiimidazole, dicyclohexylcarbodiimide, POCL 3 , BOP-Cl, thionyl chloride, oxalyl chloride, phosgene, or chloroformic esters.
3. A compound of formula (XXVII) according to claim 1 in which
J represents cyclopropyl,
X represents hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 4 -haloalkoxy,
Y represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, halogen, C 1 -C 6 -alkoxy or C 1 -C 4 -haloalkoxy, and
m represents a number 1, 2 or 3,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen.
4. A compound of formula (XXVII) according to claim 1 in which
J represents cyclopropyl,
X represents hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy or trifluoromethoxy,
Y represents hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy or trifluoromethoxy, and
m represents a number 1 or 2
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen.
5. A compound of formula (XXVII) according to claim 1 in which
J represents cyclopropyl,
X represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, methoxy or ethoxy,
Y represents hydrogen, chlorine, bromine, methyl, ethyl, propyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy,
m represents the number 1 or 2,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen,
where the radicals J, X and Y are arranged in the following phenyl substitution patterns
where only in the phenyl substitution patterns (B), (K) and (L), X may also represent hydrogen.
6. A compound of formula (XXVII) according to claim 1 in which
J represents cyclopropyl,
X represents chlorine, methyl or ethyl,
Y represents chlorine, methyl, ethyl or hydrogen,
m represents the number 1 or 2,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen,
where the radicals J, X and Y are arranged in the following phenyl substitution patterns
7. A compound of formula (XXX)
in which
J represents cyclopropyl,
X represents hydrogen, alkyl, halogen, haloalkyl, alkoxy or haloalkoxy,
Y represents hydrogen, alkyl, haloalkyl, halogen, alkoxy or haloalkoxy,
m represents a number 1, 2 or 3,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen, and
with the proviso that the compound is not
8. A compound of formula (XXX) according to claim 7 in which
J represents cyclopropyl,
X represents hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 4 -haloalkoxy,
Y represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, halogen, C 1 -C 6 -alkoxy or C 1 -C 4 -haloalkoxy, and
m represents a number 1, 2 or 3,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen.
9. A compound of formula (XXX) according to claim 7 in which
J represents cyclopropyl,
X represents hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy or trifluoromethoxy,
Y represents hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy or trifluoromethoxy, and
m represents a number 1 or 2
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen.
10. A compound of formula (XXX) according to claim 7 in which
J represents cyclopropyl,
X represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, methoxy or ethoxy,
Y represents hydrogen, chlorine, bromine, methyl, ethyl, propyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy,
m represents the number 1 or 2,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen,
where the radicals J, X and Y are arranged in the following phenyl substitution patterns
where only in the phenyl substitution patterns (B), (K) and (L), X may also represent hydrogen.
11. A compound of formula (XXX) according to claim 7 in which
J represents cyclopropyl,
X represents chlorine, methyl or ethyl,
Y represents chlorine, methyl, ethyl or hydrogen,
m represents the number 1 or 2,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen,
where the radicals J, X and Y are arranged in the following phenyl substitution patterns
12. A compound of formula (XXXIV)
in which
J represents cyclopropyl,
X represents hydrogen, alkyl, halogen, haloalkyl, alkoxy or haloalkoxy,
Y represents hydrogen, alkyl, haloalkyl, halogen, alkoxy or haloalkoxy,
m represents a number 1, 2 or 3,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen, and
R 8 represents alkyl.
13. A compound of formula (XXXIV) according to claim 12 , in which
R 8 represents C 1 -C 6 alkyl.
14. A compound of formula (XXXIV) according to claim 12 , in which
R 8 represents C 1 -C 8 alkyl.
15. A compound of formula (XXXIV) according to claim 12 in which
J represents cyclopropyl,
X represents hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 4 -haloalkoxy,
Y represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, halogen, C 1 -C 6 -alkoxy or C 1 -C 4 -haloalkoxy, and
m represents a number 1, 2 or 3,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen.
16. A compound of formula (XXXIV) according to claim 12 in which
J represents cyclopropyl,
X represents hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy or trifluoromethoxy,
Y represents hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy or trifluoromethoxy, and
m represents a number 1 or 2
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen.
17. A compound of formula (XXXIV) according to claim 12 in which
J represents cyclopropyl,
X represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, methoxy or ethoxy,
Y represents hydrogen, chlorine, bromine, methyl, ethyl, propyl, trifluoromethyl, methoxy, ethoxy or trifluoromethoxy,
m represents the number 1 or 2,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen,
where the radicals J, X and Y are arranged in the following phenyl substitution patterns
where only in the phenyl substitution patterns (B), (K) and (L), X may also represent hydrogen.
18. A compound of formula (XXXIV) according to claim 12 in which
J represents cyclopropyl,
X represents chlorine, methyl or ethyl,
Y represents chlorine, methyl, ethyl or hydrogen,
m represents the number 1 or 2,
with the proviso that at least one of the radicals J, X or Y is located in the 2-position of the phenyl radical and is not hydrogen,
where the radicals J, X and Y are arranged in the following phenyl substitution patterns