Stable insecticide compositions and methods for producing same
View Patent ↗Insect controlling compositions including an N-substituted (6-haloalkylpyridin-3-yl)alkyl sulfoximine compound exhibiting increased stability, along with methods for preparing same, are disclosed.
1. A method, comprising:
providing a composition including a first ratio between stereoisomers of a compound having the following formula (I):
wherein
X represents NO 2 , CN or COOR 4 ;
L represents a single bond or R 1 , S and L taken together represents a 4-, 5- or 6-membered ring;
R 1 represents (C 1 -C 4 ) alkyl;
R 2 and R 3 are distinct from each other and individually represent hydrogen, methyl, ethyl, fluoro, chloro or bromo;
n is 1 when L represents a single bond or is 0 when R 1 , S and L taken together represents a 4-, 5- or 6-membered ring;
Y represents (C 1 -C 4 ) haloalkyl, F, Cl, Br, or I; and
R 4 represents (C 1 -C 3 ) alkyl; and
heating the composition in a manner effective to provide a second, distinct ratio between the stereoisomers.
2. The method of claim 1 , wherein L represents a single bond and the compound includes the following structure:
wherein
X represents NO 2 , CN or COOR 4 ;
R 1 represents (C 1 -C 4 ) alkyl;
R 2 and R 3 are distinct from each other and individually represent hydrogen, methyl, ethyl, fluoro, chloro or bromo;
Y represents (C 1 -C 4 ) haloalkyl, F, Cl, Br, or I; and
R 4 represents (C 1 -C 3 ) alkyl.
3. The method of claim 1 , wherein R 1 , S and L taken together form a 5-membered ring and n is 0 and the compound includes the following structure:
wherein
X represents NO 2 , CN or COOR 4 ;
Y represents (C 1 -C 4 ) haloalkyl, F, Cl, Br, or I; and
R 4 represents (C 1 -C 3 ) alkyl.
4. The method of claim 1 , wherein X represents NO 2 or CN, Y represents —CF 3 , and R 2 and R 3 independently represent hydrogen, methyl or ethyl.
5. The method of claim 1 , wherein the composition further includes a spinosyn selected from the group consisting of spinetoram, spinosad and mixtures thereof.
6. The method of claim 1 , which further includes, subsequent to said heating, applying to a locus where control is desired an insect-inactivating amount of the composition.
7. The method of claim 1 , wherein the heating is performed at a minimum of about 50° C. from about four to about seventy two hours.
8. The method of claim 1 , wherein the composition includes a first pair of stereoisomers and a second pair of stereoisomers, and the first ratio is between the first and second pairs of stereoisomers and includes a value of about 1:2.
9. The method of claim 8 , wherein the second ratio is between the first and second pairs of stereoisomers and includes a value of at least 1:1.
10. The method of claim 9 , wherein the second ratio includes a value in the range of about 3:1 to about 100:1.
11. The method of claim 10 , wherein the second ratio includes a value in the range of about 3:1 to about 40:1.
12. The method of claim 9 , wherein the second ratio includes a value greater than 10:1.