# US 2010/0168178 A1 · Stable insecticide compositions and methods for producing same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2010/0168178 A1 - Document ID: US20100168178A1 - Status: Published application - Kind: A1 - Application number: 12/653,996 - Filed: 2009-12-22 - Published: 2010-07-01 - Earliest claimed: 2008-12-26 - Assignees: Dow AgroSciences LLC - Inventors: Kuide Qin; Raymond E. Boucher, JR. - Web page: https://patentgrep.com/patent/US20100168178A1 ## CPC - A01N 43/40: six-membered rings - A01N 43/22: rings with more than six members - A01N 47/40: the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides - C07D 213/34: to which a second hetero atom is attached - C07D 213/53: Nitrogen atoms - C07D 213/57: Nitriles - C07D 409/04: directly linked by a ring-member-to-ring-member bond - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) ## Abstract 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. ## Claims ### Claim 1 A method, comprising: providing a composition including a first ratio between stereoisomers of a compound having the following formula (I): wherein X represents NO2, CN or COOR4; L represents a single bond or R1, S and L taken together represents a 4-, 5- or 6-membered ring; R1 represents (C1-C4) alkyl; R2 and R3 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 R1, S and L taken together represents a 4-, 5- or 6-membered ring; Y represents (C1-C4) haloalkyl, F, Cl, Br, or I; and R4 represents (C1-C3) alkyl; and heating the composition in a manner effective to provide a second, distinct ratio between the stereoisomers. ### Claim 2 (depends on 1) The method of claim 1, wherein L represents a single bond and the compound includes the following structure: wherein X represents NO2, CN or COOR4; R1 represents (C1-C4) alkyl; R2 and R3 are distinct from each other and individually represent hydrogen, methyl, ethyl, fluoro, chloro or bromo; Y represents (C1-C4) haloalkyl, F, Cl, Br, or I; and R4 represents (C1-C3) alkyl. ### Claim 3 (depends on 1) The method of claim 1, wherein R1, S and L taken together form a 5-membered ring and n is 0 and the compound includes the following structure: wherein X represents NO2, CN or COOR4; Y represents (C1-C4) haloalkyl, F, Cl, Br, or I; and R4 represents (C1-C3) alkyl. ### Claim 4 (depends on 1) The method of claim 1, wherein X represents NO2 or CN, Y represents —CF3, and R2 and R3 independently represent hydrogen, methyl or ethyl. ### Claim 5 (depends on 1) The method of claim 1, wherein the composition further includes a spinosyn selected from the group consisting of spinetoram, spinosad and mixtures thereof. ### Claim 6 (depends on 1) 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. ### Claim 7 (depends on 1) 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. ### Claim 8 A method, comprising: providing a composition including a stereoisomeric mixture of a compound having the following structure: wherein X represents NO2, CN or COOR4; R1 represents (C1-C4) alkyl; R2 and R3 are distinct from each other and individually represent hydrogen, methyl, ethyl, fluoro, chloro or bromo; Y represents (C1-C4) haloalkyl, F, Cl, Br, or I; R4 represents (C1-C3) alkyl; and the mixture is defined by a first pair of diastereomers and a second pair of diastereomers; and heating the composition to convert at least a portion of the second pair of diastereomers to the first pair of diastereomers. ### Claim 9 (depends on 8) The method of claim 8, wherein the heating is performed at a minimum of about 50° C. from about four to about seventy two hours. ### Claim 10 (depends on 8) The method of claim 8, wherein the composition includes a spinosyn selected from the group consisting of spinetoram, spinosad and mixtures thereof. ### Claim 11 (depends on 8) The method of claim 8, wherein X represents NO2 or CN, Y represents —CF3 and R2 and R3 independently represent hydrogen, methyl or ethyl. ### Claim 12 A composition, comprising a stereoisomeric mixture of {1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}(methyl)oxido-λ4-sulfanylidenecyanamide defined by a first pair of diastereomers and a second pair of diastereomers, wherein the first and second pairs of diastereomers are present at a ratio of at least about 3:1. ### Claim 13 (depends on 12) The composition of claim 12, wherein the first and second pairs of diastereomers are present at a ratio from about 3:1 to about 100:1. ### Claim 14 (depends on 12) The composition of claim 12, wherein the first and second pairs of diastereomers are present at a ratio from about 3:1 to about 40:1. ### Claim 15 (depends on 12) The composition of claim 12, wherein the first pair of diastereomers is defined by {(R)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-(R)-(methyl)oxido-λ4-sulfanylidenecyanamide and {(S)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-(S)(methyl)oxido-λ4-sulfanylidenecyanamide and the second pair of diastereomers is defined by {(R)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-(S)-(methyl)oxido-λ4-sulfanylidenecyanamide and {(S)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-(R)-(methyl)oxido-λ4-sulfanylidenecyanamide. ### Claim 16 (depends on 12) The composition of claim 12, further comprising one or more other insecticides. ### Claim 17 (depends on 16) The composition of claim 16, wherein said insecticide is a spinosyn selected from the group consisting of spinetoram, spinosad and mixtures thereof. ### Claim 18 (depends on 17) The composition of claim 17, wherein the ratio, by weight, between {1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}(methyl)oxido-λ4-sulfanylidenecyanamide and the spinosyn is from about 3:1 to about 1:3. ### Claim 19 (depends on 18) The composition of claim 18, wherein the ratio, by weight, between {1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}(methyl)oxido-λ4-sulfanylidenecyanamide and the spinosyn is about 2:1. ### Claim 20 (depends on 12) A method of controlling insects which comprises applying to a locus where control is desired an insect-inactivating amount of a composition according to claim 12.