The present application relates to novel substituted N′-cyano-N-halogenalkylimidamide derivatives, to processes for their preparation and to their use for controlling animal pests, especially arthropods, in particular insects.
1. A compound of the formula (I)
in which
A represents 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-methylpyrid-3-yl, 6-trifluoromethyl-pyrid-3-yl, 2-methylpyrimidin-5-yl, 2-chloropyrimid-5-yl, 1H-pyrazol-4-yl which is optionally substituted in the 1-position by methyl or ethyl and in the 3-position by chlorine, 1H-pyrazol-5-yl, 3-methylpyrazol-5-yl, 2-bromo-1,3-thiazol-5-yl, 2-chloro-1,3-thiazol-5-yl, isoxazol-5-yl which is optionally substituted in the 3-position by methyl, ethyl, chlorine, or bromine, 3-methyl-1,2,4-oxadiazol-5-yl, 1-methyl-1,2,4-triazol-3-yl, or 1,2,5-thiadiazol-3-yl,
or
A represents 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-bromo-6-chloropyrid-3-yl, 5-fluoro-6-bromopyrid-3-yl, 5-chloro-6-bromopyrid-3-yl, 5,6-dibromopyrid-3-yl, 5-methyl-6-chloropyrid-3-yl or 5-methyl-6-bromopyrid-3-yl,
or
A represents a radical
in which
n represents 2 or 3, and
Z represents fluorine or chlorine,
R 1 represents 2,2-difluoroethyl,
R 2 represents methyl or ethyl, and
B represents a radical selected from the group consisting of (B-1) to (B-9)
2. The compound according to claim 1 in which
A represents a radical selected from the group consisting of 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 2-methylpyrimidin-5-yl, 2-chloropyrimid-5-yl, 3-methylisoxazol-5-yl, 3-bromoisoxazol-5-yl, 5-fluoro-6-chloropyrid-3-yl, 5,6-dichloropyrid-3-yl, 5-fluoro-6-bromopyrid-3-yl, and 2-chloro-1,3-thiazol-5-yl,
R 1 represents 2,2-difluoroethyl,
R 2 represents methyl, and
B represents methylene (—CH 2 —).
3. A process for preparing
a compound of the formula (I) according to claim 1 , comprising
a) reacting in a first reaction step, a compound of the formula (II)
in which
R 2 is defined in claim 1 and LG represents a suitable leaving group,
with a compound of the formula (III)
R 1 —NH 2 (III)
in which
R 1 is as defined in claim 1 ,
optionally in the presence of a suitable diluent and optionally in the presence of a basic auxiliary, to give a compound of the formula (IV)
in which
R 1 and R 2 are as defined in claim 1 ,
and then reacting in a second reaction step, a compound of formula (IV) with a compound of the formula (V)
A-B-E (V)
in which
A and B are as defined in claim 1 , and
E represents a suitable leaving group LG,
optionally in the presence of a suitable diluent and optionally in the presence of a basic auxiliary, or
b) reacting a compound of the formula (II)
in which
R 2 is as defined in claim 1 and LG is as defined above,
with a compound of the formula (VI)
A-B—N(R 1 )H (VI)
in which
A, B and R 1 are as defined in claim 1 ,
optionally in the presence of a suitable diluent and optionally in the presence of a basic auxiliary, or
c) reacting in a first reaction step an orthoester of the formula (VII)
in which
R 2 is as defined in claim 1 , and
R′ represents methyl or ethyl,
in situ with cyanamide, optionally in the presence of one or more diluents, to give a compound of the formula (II)
in which
R 2 is as defined in claim 1 and LG is as defined above,
and then, reacting in a second reaction step, a compound of the formula (II) with a compound of the formula (VIII)
A-B—NH 2 (VIII)
in which
A and B are as defined in claim 1 ,
optionally in the presence of a suitable diluent and optionally in the presence of a basic auxiliary, to give a compound of the formula (IX)
in which
A, B, R 2 are as defined above,
and then, reacting in a third reaction step, a compound of the formula (IX) with a compound of the formula (X)
R 1 -E (X)
in which
R 1 is as defined in claim 1 and E is as defined above,
optionally in the presence of a suitable diluent and optionally in the presence of a basic auxiliary.
4. A composition, comprising at least one compound of the formula (I) according to claim 1 and one or more extenders, surfactants, or combinations thereof.
5. A method for controlling pests, comprising contacting a compound of the formula (I) according to claim 1 with pests or their habitat.
6. A method for controlling pests, comprising contacting a composition according to claim 4 with pests or their habit.
7. A compound of formula (IV-1):
8. The compound according to claim 1 , having the formula: