Substituted enaminocarbonyl compounds used as insecticides
View Patent ↗The present application relates to novel substituted enaminocarbonyl compounds, to processes for their preparation and to their use for controlling animal pests, especially arthropods, in particular insects.
1. A compound of formula (I)
in which
A represents one of the radicals pyrimidinyl, pyrazolyl, thiophenyl, oxazolyl, isoxazolyl, 1,2,4-oxadiazolyl, isothiazolyl, 1,2,4-triazolyl or 1,2,5-thiadiazolyl which are optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and/or chlorine), C 1 -C 3 -alkylthio (which is optionally substituted by fluorine and/or chlorine), or C 1 -C 3 -alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine), or
A represents a radical
in which
X represents halogen, alkyl or haloalkyl,
Y represents halogen, alkyl, haloalkyl, haloalkoxy, azido or cyano,
B represents oxygen, sulphur or methylene,
R 1 represents haloalkyl, haloalkenyl, halocycloalkyl or halocycloalkylalkyl,
R 2 represents hydrogen or halogen and
R 3 represents hydrogen or alkyl.
2. A compound of formula (I)
in which
A represents a pyrimidin-5-yl radical which is substituted in the 2-position by halogen or halo-C 1 -C 4 -alkyl, or
A represents a radical
in which
X represents halogen, C 1 -C 1 -alkyl or halo-C 1 -C 4 -alkyl,
Y represents halogen, C 1 -C 4 -alkyl, halo-C 1 -C 4 -alkyl, halo-C 1 -C 4 -alkoxy, azido or cyano,
B represents oxygen, sulphur or methylene,
R 1 represents halo-C 1 -C 3 -alkyl, halo-C 2 -C 3 -alkenyl, halocyclopropyl,
R 2 represents hydrogen or halogen and
R 3 represents hydrogen or alkyl.
3. A composition, comprising at least one compound of formula (I) according to claim 1 with an extender and/or surfactant.
4. A method for controlling a pest, comprising allowing a compound of formula (I) according to claim 1 to act on the pest and/or a habitat thereof.
5. A composition according to claim 3 for controlling pests.
6. A composition comprising at least one compound of formula (I) according to claim 2 , with an extender and/or a surfactant.
7. A method for controlling a pest comprising allowing a compound of formula (I) according to claim 2 to act on the pest and/or a habitat thereof.
8. A method for controlling a pest comprising allowing a composition according to claim 3 to act on the pest and/or a habitat thereof.
9. A composition according to claim 6 for controlling pests.
10. A compound according to claim 1 , wherein A represents a radical
in which
X represents halogen, alkyl or haloalkyl, and
Y represents halogen, alkyl, haloalkyl, haloalkoxy, azido or cyano.
11. A compound according to claim 1 , wherein A represents one of the radicals pyrimidinyl, pyrazolyl, thiophenyl, oxazolyl, isoxazolyl, 1,2,4-oxadiazolyl, isothiazolyl, 1,2,4-triazolyl or 1,2,5-thiadiazolyl which are optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and/or chlorine), C 1 -C 3 -alkylthio (which is optionally substituted by fluorine and/or chlorine), or C 1 -C 3 -alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine).
12. A method for the manufacture of a compound of formula (I)
in which
A represents a radical
in which
X represents halogen, alkyl or haloalkyl,
Y represents halogen, alkyl, haloalkyl, haloalkoxy, azido or cyano,
B represents oxygen, sulphur or methylene,
R 1 represents haloalkyl, haloalkenyl, halocycloalkyl or halocycloalkylalkyl,
R 2 represents hydrogen or halogen and
R 3 represents hydrogen or alkyl,
which method comprises
reacting a compound of formula (II)
in which B, R 2 , and R 3 are defined as above with a compound of formula (III)
HN(R 1 )-CH 2 -A (III)
in which A and R 1 are as defined above,
in the presence of an acidic auxiliary selected from p-toluenesulphonic acid or acetic acid and, optionally in the presence of a diluent.
13. A method according to claim 12 , wherein the diluent is present and selected from the group consisting of benzene, toluene, chlorobenzene, bromobenzene, nitrobenzene, and xylene.
14. A method according to claim 13 , wherein the reaction is carried out at temperatures between 20° C. and 140° C.
15. A method according to claim 12 , wherein the compound of formula (II) is tetronic acid and the compound of formula (III) is N-[(6-chloro-5-fluoropyridin-3-yl) methyl]-2,2-difluoroethane-1-amine.
16. A compound of formula (III)
HN(R 1 )-CH 2 -A (III)
in which
A represents a radical
in which
X represents halogen, alkyl or haloalkyl,
Y represents halogen, alkyl, haloalkyl, haloalkoxy, azido or cyano, and
R 1 represents haloalkyl, haloalkenyl, halocycloalkyl or halocycloalkylalkyl.
17. The compound according to claim 16 , wherein the compound of formula (III) is N-[(6-chloro-5-fluoropyridin-3-yl)methyl]-2,2-difuoroethane-1-amine.