2,4,6-phenyl-substituted cyclic ketoenols
View Patent ↗The invention relates to novel 2,4,6-phenyl-substituted cyclic ketoenols of the formula (I), in which CKE, W, X and Y are as defined above, to a plurality of processes and intermediates for their preparation and to their use as pesticides and/or herbicides, and also to selective herbicidal compositions comprising firstly the 2,4,6-phenyl-substituted cyclic ketoenols and secondly at least one compound which improves crop plant tolerance.
1. A compound of formula (I)
in which
W represents methoxy, ethoxy, n-propoxy, methoxyethoxy or cyclopropylmethoxy,
X represents chlorine,
Y represents methyl,
CKE represents the group
A represents methyl, ethyl, isopropyl, isobutyl or cyclopropyl,
B represents hydrogen, methyl or ethyl, or
A, B and the carbon atom to which they are attached represent saturated C 5 -C 6 -cycloalkyl in which optionally one ring atom is replaced by oxygen and which is optionally monosubstituted by methyl or methoxy,
D represents hydrogen, methyl or ethyl,
G represents hydrogen (a) or represents one of the groups
E represents an ammonium ion,
R 1 represents C 1 -C 6 -alkyl, C 1 -C 2 -alkoxy-C 1 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkyl which is monosubstituted by chlorine or represents phenyl which is optionally monosubstituted by chlorine,
R 2 represents C 1 -C 8 -alkyl, C 3 -C 6 -alkenyl or benzyl,
R 3 represents C 1 -C 6 -alkyl.
2. A process for preparing a compound of the formula (I) according to claim 1 , comprising
(A) obtaining a compound of the formula (I-1-a)
in which
A, B, D, W, X and Y are as defined in claim 1 , by the intramolecular condensation of a compound of the formula (II)
in which
A, B, D, W, X and Y are as defined in claim 1 ,
and
R 8 represents alkyl,
in the presence of a diluent and in the presence of a base,
(I) obtaining a compound of the formula (I-1-b)
in which A, B, D, R 1 , W, X and Y are as defined in claim 1 , by the reaction of a compound of the formula (I-1-a) in which A, B, D, W, X and Y are as defined in claim 1
(a) is reacted with an acid halide of the formula (XIII)
in which
R 1 is as defined in claim 1 and
Hal represents halogen,
or
(b) with a carboxylic anhydride of the formula (XIV)
R 1 —CO—O—CO—R 1 (XIV)
in which
R 1 is as defined in claim 1 ,
optionally in the presence of a diluent and optionally in the presence of an acid binder,
(J) obtaining a compound of the formula (I-1-c)
in which A, B, D, R 2 , W, X and Y are as defined in claim 1 , M represents oxygen, and L represents oxygen, by the reaction of a compound of the formula (I-1-a) in which A, B, D, W, X and Y are as defined in claim 1
with a chloroformic ester of the formula (XV)
R 2 -M-CO—Cl (XV)
in which
R 2 is as defined in claim 1 , and M is defined above, optionally in the presence of a diluent and optionally in the presence of an acid binder,
(L) obtaining a compound of the formula (I-1-d)
in which A, B, D, R 3 , W, X and Y are as defined in claim 1 , by the reaction of a compound of the formula (I-1-a) in which A, B, D, W, X and Y are as defined above,
with a sulphonyl chloride of formula (XVII)
R 3 —SO 2 —Cl (XVII)
in which
R 3 is as defined in claim 1 ,
optionally in the presence of a diluent and optionally in the presence of an acid binder,
(N) obtaining a compound of the formula (I-1-f)
in which A, B, D, E, W, X and Y are as defined in claim 1 , by the reaction of a compound of the formula (I-1-a) in which A, B, D, W, X and Y are as defined in claim 1
with an amine of the formula (XX),
in which
R 10 , R 11 , R12 independently of one another represent hydrogen or alkyl, optionally in the presence of a diluent,
(P) obtaining a compound of the formula (I-1-a) in which A, B, D, W, X and Y are as defined above, by the reaction of a compound of the formula (I-1-a′) in which A, B, D, X and Y are as defined above and W′ represents bromine
with an alcohol of the formula
W—OH
in which
W is as defined in claim 1 , optionally in the presence of a solvent, a Cu(I) salt and a strong base.
3. A pesticide or herbicide comprising at least one compound of the formula (I) according to claim 1 .
4. A method for controlling animal pests or unwanted vegetation comprising contacting a compound of the formula (I) according to claim 1 with the pests or their habitat.
5. A process for preparing pesticides or herbicides comprising mixing at least one compound of the formula (I) according to claim 1 with an extender or a surfactant or a combination thereof.