Method to control insects resistant to common insecticides
a technology of insecticides and insect repellents, applied in the field of methods to control insects resistant to common insecticides, can solve the problem of difficult prediction of cross resistance, and achieve the effect of lack of cross resistan
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example i
[(6-Trifluoromethylpyridin-3-yl)methyl](methyl)-oxido-λ4-sulfanylidenecyanamide (1)
[0050]
[0051][(6-Trifluoromethylpyridin-3-yl)methyl](methyl)-oxido-λ4-sulfanylidene-cyanamide (1) was prepared from 3-chloromethyl-6-(trifluoromethyl)pyridine according to the following three step sequence:
[0052]To a solution of 3-chloromethyl-6-(trifluoromethyl)pyridine (5.1 g, 26 mmol) in dimethyl sulfoxide (DMSO; 20 mL) was added in one portion sodium thiomethoxide (1.8 g, 26 mmol). A violent exothermic reaction was observed which resulted in the reaction turning dark. The reaction was stirred for 1 hr, then additional sodium thiomethoxide (0.91 g, 13 mmol) was added slowly. The reaction was stirred overnight, after which it was poured into H2O and several drops of conc. HCl were added. The mixture was extracted with Et2O (3×50 mL) and the organic layers combined, washed with brine, dried over MgSO4 and concentrated. The crude product was purified by chromatography (Prep 500, 10% acetone / hexanes) t...
example ii
[1-(6-Trifluoromethylpyridin-3-yl)ethyl](methyl)-oxido-λ4-sulfanylidenecyanamide (2)
[0055]
[0056][1-(6-Trifluoromethylpyridin-3-yl)ethyl](methyl)-oxido-λ4-sulfanylidene-cyanamide (2) was prepared from [(6-trifluoromethylpyridin-3-yl)methyl]-(methyl)-oxido-λ4-sulfanylidenecyanamide (1) using the method outlined in Scheme C:
[0057]To a solution of sulfoximine (1) (50 mg, 0.19 mmol) and hexamethyl-phosphoramide (HMPA; 17 μL, 0.10 mmol) in tetrahydrofuran (THF; 2 mL) at −78° C. was added potassium hexamethyldisilazane (KHMDS; 0.5 M in toluene, 420 μL, 0.21 mmol) dropwise. The solution was stirred at −78° C. for an additional 20 min, after which iodomethane (13 μL, 0.21 mmol) was added. The reaction was allowed to warm to room temperature over the course of 1 hr, after which it was quenched with saturated aqueous (aq.) NH4Cl and extracted with dichloro-methane. The organic layer was dried over Na2SO4, concentrated, and the crude product purified by chromatography (chromatotron, 70% aceton...
example iii
2-(6-Trifluoromethylpyridin-3-yl)-1-oxido-tetrahydro-1H-1λ4-thien-1-ylidenecyanamide (3)
[0058]
[0059]2-(6-Trifluoromethylpyridin-3-yl)-1-oxido-tetrahydro-1H-1λ4-thien-1-ylidene-cyanamide (3) was prepared from 3-chloromethyl-6-(trifluoromethyl)-pyridine according to the 5 step sequence outline below:
[0060]To a suspension of thiourea (1.2 g, 16 mmol) in EtOH (25 mL) was added a solution of 3-chloromethyl-6-(trifluoromethyl)pyridine in EtOH (10 mL). The suspension was stirred at room temperature for 2 days, during which a white precipitated formed. The precipitate was filtered to give the desired amidine hydrochloride as a white solid (2.4 g, 58%). Mp=186-188° C. No further attempt was made to purify the product. 1H NMR (300 MHz, CDCl3): δ 8.9 (bs, 4H), 8.4 (s, 1H), 7.6 (d, 1H), 7.3 (d, 1H), 4.2 (s, 2H); LC-MS (ELSD): mass calcd for C8H8F3N3S [M+H]+ 236.05. Found 236.01.
[0061]To a solution of amidine hydrochloride (A) (1.8 g, 6.8 mmol) in H2O (12 mL) at 10° C. was added 10 N NaOH (0.68 ...
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