Pesticidal 3-(substituted phenyl)-5-(thienyl or furyl)-1,2,4-triazoles
A substituted, unsubstituted technology, applied in biocides, compounds of Group 4/14 elements of the periodic table, organic chemistry, etc.
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Embodiment 1
[0095] The following steps illustrate the preparation of amidrazones of formula (2a)
[0096]
[0097] a. 2,6-Difluorobenzylthioamide
[0098] To a 3-L three-necked round-bottom flask equipped with a mechanical stirrer, dry ice condenser, dropping funnel, and outlet leading to a bleach trap was charged pyridine (550 mL), 2,6-difluorophenyl Cyanogen (208 g, 1.50 mol), triethylamine (202 g, 279 mL, 2.0 mol), and sodium sulfide hydrate (521 g, 2.17 mol, crushed into pieces small enough to fit in a flask). The temperature of the stirred mixture was lowered to about 5°C, and concentrated hydrochloric acid (143 g, 288 mL, 3.99 mol) was added dropwise to the slurry. An exotherm occurred and the rate of addition of concentrated hydrochloric acid was controlled so that the temperature of the reaction mixture did not exceed 25°C during the total addition time of 75 minutes. The cooling bath was removed and the slurry was allowed to warm to room temperature and stir overnight. Th...
Embodiment 2
[0107] 3-(2,6-difluorophenyl)-5-(3-n-hexylthiophen-2-yl)-1-methyl [1,2,4]triazole (compound 35)
[0108] To a mixture of 3-n-hexyl-2-thiophenecarboxylic acid (0.5 g, 2.4 mmol) in 25 mL of anhydrous 1,2-dichloroethane was added 2.0 mL of thionyl chloride and a drop of dimethylformamide. The mixture was refluxed for four hours. After cooling, the reaction mixture was evaporated in vacuo and the residue was combined with 25 mL of anhydrous toluene and 1.24 g (3.0 mmol) of amidrazone (Example 1) of formula (2a). The mixture was refluxed overnight, cooled, and then partitioned between brine and ether. The organic phase was dried (MgSO 4 ), the solvent was evaporated and the residue was chromatographed on silica gel using ethyl acetate / hexane (5:95 to 20:80) as eluent. The product fractions were collected and evaporated to give 0.66 g (76% yield) of the title compound as an oil. 1 H NMR δ7.26-7.46 (m, 2H), 6.97-7.06 (m, 2H), 3.97 (s, 3H), 2.71 (m, 2H), 1.23 (m, 6H), 0.84 (m,...
Embodiment 3
[0110] 3-(2,6-difluorophenyl)-5-(4-p-chlorobenzenesulfonyl-3-methylthiophen-2-yl)-1-methyl [1,2,4]triazole (compound 12)
[0111] Under stirring, add amidrazone (embodiment 1) shown in 0.9g (2.2mmol) formula (2a) and 0.75g (2.2mmol) thiophene acid chloride--4-(p-chlorobenzenesulfonyl)-3-methylthiophene 1 equivalent (0.4 g, 2.2 mmol) of p-toluenesulfonic acid monohydrate was added to a solution of 2-carbonyl chloride in 100 mL of toluene. The mixture was refluxed overnight and water was removed using a Dean-Stark trap. The solution was cooled, and the solvent was removed in vacuo. The residue was dissolved in 100 mL of dichloromethane and washed with 2N NaOH followed by water. The organic phase was dried (MgSO 4 ), and the solvent was evaporated. The residue was recrystallized from ethyl acetate / hexanes to give 0.6 g of product as off-white crystals. The melting point is 183-185°C, and the yield is 59.4%. 1 H NMRδ8.4.
[0112] C 20 h 14 f 2 ClN 3 o 2 S 2 Calcul...
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