Substituted enaminocarbonyl compounds
View Patent ↗The present invention 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 method for the manufacture of a compound of the formula (I)
in which
A represents pyrid-3-yl which is optionally substituted in the 6-position by fluorine, chlorine, bromine or trifluoromethyl, or represents 1,3-thiazol-5-yl which is optionally substituted in the 2-position by chlorine;
B represents oxygen, sulphur or methylene;
R 1 represents halo-C 1 -C 3 -alkyl or halo-C 2 -C 3 -alkenyl;
R 2 represents hydrogen or halogen; and
R 3 represents hydrogen or methyl;
which method comprises reacting a compound of the formula (II)
in which
B represents oxygen, sulphur or methylene;
R 2 represents hydrogen or halogen; and
R 3 represents hydrogen or methyl;
with a compound of the formula (III)
HN(R 1 )—CH 2 -A (III)
in which
A represents pyrid-3-yl which is optionally substituted in the 6-position by fluorine, chlorine, bromine or trifluoromethyl, or represents 1,3-thiazol-5-yl which is optionally substituted in the 2-position by chlorine; and
R 1 represents halo-C 1 -C 3 -alkyl or halo-C 2 -C 3 -alkenyl;
in the presence of an acidic auxiliary selected from p-toluenesulfonic acid or acetic acid, optionally in the presence of a suitable diluent.
2. The method according to claim 1 in which
A represents 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-trifluoromethylpyrid-3-yl, or 2-chloro-1,3-thiazol-5-yl;
B represents oxygen or methylene;
R 1 represents fluorine-substituted C 1 -C 3 -alkyl or C 2 -C 3 -alkenyl;
R 2 represents hydrogen or halogen; and
R 3 represents hydrogen or methyl.
3. The method according to claim 1 , wherein the suitable diluent is present and is selected from benzene, toluene, chlorobenzene, bromobenzene, nitrobenzene or xylene.
4. The method according to claim 2 , wherein the suitable diluent is present and is selected from benzene, toluene, chlorobenzene, bromobenzene, nitrobenzene or xylene.
5. A method according to claim 1 , wherein the reaction is carried out at temperatures between 60° C. and 140° C.
6. A method according to claim 1 , wherein the compound of the formula (II) is tetronic acid and the compound of the formula (III) is N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethane-1-amine.