synergistic insecticidal mixture
A synergistic and composition technology, which can be used in pesticides, active ingredients of heterocyclic compounds, biocides, etc., and can solve problems such as the formation of resistance to pesticides
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Embodiment I
[0065] Example I. [(6-Trifluoromethylpyridin-3-yl)methyl](methyl)-oxidation-λ 4 - Sulfuriminonitrile (1)
[0066]
[0067] [(6-Trifluoromethylpyridin-3-yl)methyl](methyl)-oxidation-λ 4 -Sulphoiminonitrile (1) is prepared from 3-chloromethyl-6-(trifluoromethyl)pyridine according to the following three-step sequence:
[0068]
[0069] To a solution of 3-chloromethyl-6-(trifluoromethyl)pyridine (5.1 g, 26 mmol) in dimethylsulfoxide (DMSO; 20 mL) was added sodium methylthiolate (1.8 g, 26 mmol) in one portion . A vigorous exothermic reaction was observed which resulted in a dark color of the reaction mixture. The reaction mixture was stirred for 1 hour, then additional sodium methylthiolate (0.91 g, 13 mmol) was added slowly. The reaction mixture was stirred overnight, after which it was poured into H 2 O, and then add a few drops of concentrated HCl. Mixture with Et 2 O (ether) (3 × 50mL) extraction, combined organic layer, washed with brine, washed over MgSO 4 D...
Embodiment II
[0074] Example II. [1-(6-trifluoromethylpyridin-3-yl)ethyl](methyl)-oxidation-λ 4 - Sulfuriminonitrile (2)
[0075]
[0076] [1-(6-trifluoromethylpyridin-3-yl)ethyl](methyl)-oxidation-λ 4-Sulphoiminonitrile (2) was obtained from [(6-trifluoromethylpyridin-3-yl)methyl]-(methyl)-oxidized-λ using the method outlined in Scheme C 4 - Sulfuriminonitrile (1) to prepare:
[0077] To a solution of sulfoxime (1) (50 mg, 0.19 mmol) and hexamethyl-phosphoramide (HMPA; 17 μL, 0.10 mmol) in tetrahydrofuran (THF; 2 mL) was added dropwise hexamethyl-phosphoramide at -78°C Potassium disilazide (KHMDS; 0.5 M in toluene, 420 μL, 0.21 mmol). The solution was stirred at -78°C for an additional 20 minutes before adding iodomethane (13 μL, 0.21 mmol). The reaction mixture was allowed to warm to room temperature over 1 h, after which it was washed with saturated NH 4 Quenched with aqueous Cl, then extracted with dichloromethane. The organic layer was washed with Na 2 SO 4 Drying, conce...
Embodiment III
[0078] Example III. 2-(6-Trifluoromethylpyridin-3-yl)-1-oxo-tetrahydro-1H-1λ 4 - Thiophene-1-ylidene amino Nitrile (3)
[0079]
[0080] 2-(6-Trifluoromethylpyridin-3-yl)-1-oxo-tetrahydro-1H-1λ 4 -thiophen-1-ylidene-cyanamide (3) was prepared from 3-chloromethyl-6-(trifluoromethyl)-pyridine according to the 5-step sequence outlined below:
[0081]
[0082] 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 time a white precipitate formed. The precipitate was filtered to afford the desired amidine hydrochloride as a white solid (2.4 g, 58%). Mp = 186-188°C. No further attempts were made to purify the product. 1 HNMR (300MHz, CDCl 3 ): δ 8.9 (bs, 4H), 8.4 (s, 1H), 7.6 (d, 1H), 7.3 (d, 1H), 4.2 (s, 2H). LC-MS (ELSD): C 8 h 8 f 3 N 3 S[M+H] + Mass calculated 236.05, observed 236.01.
[0083] ...
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