Synthesis And Insecticidal Activity Of Oxime Ether Containing An Aryl Oxazole/thiazole Ring

Inspired by the design idea of“Intermediate Derivatization Methods”,chosen the intermediates of approved agricultural chemicals as the basic skeleton,the oxime ether structure was introduced to obtain a series of novel oxime ether compounds.?1?Starting with 1-?4-chlorophenyl?-2-cyclopropylacetone,1-?4-chlorophenyl?-2-cyclopropylacetone oxime ether?A1^A9 and A17?were obtained by deuteration and etherification.1-?4-chlorophenyl?-2-cyclopropylacetone hydrazinyl oxazole methyl ether?A10^A16?were prepared by aralic acid via amidation,cyclization and etherification.1-?4-chlorophenyl?-2-cyclopropylacetone hydrazinyl thiazole methyl ether?A18^A24?were conducted by arylformamide via thio reaction,cyclization,etherification.The yield of compound A was 45.5⁸0.4%.?2?Chosen furan phenol as material,7-methoxy-2,2-dimethyl-2,3-dihydro-5-benzo-furanyl ketoxime?B1^B14?were obtained by methyl etherification,acylation,deuteration,etherification.The yield was 46.3⁷9.1%.?3?The structure of the compound A and B were confirmed by structural characterization,and the compound A12 was confirmed by X-ray single crystal diffraction.The results showed that the compound A12 belongs to the monoclinic system.The space group is P2₁/c,and each unit cell of it contains four molecules.The entire molecule has an E-type configuration centered on C?11?=N?2?.The C?3?—C?4?—C?5?plane of the benzene ring and the N?1?—C?7?—O?1?plane of the oxazole ring are connected by C?7?—C?4?,and the dihedral angle is 9.687°.The dihedral angle of C?13?—C?12?—C?17?plane and the N?2?—O?2?—C?10?plane is 87.883°.?4?The screening results of insecticidal activity at the concentration of 500 mg/L showed that the mortalities of compound A6 and A11 against Mythimna sepatara were 100%.Twelve compounds showed up to 50%inhibition rate against Aphis aphids.Five compounds'mortalities against Aphis fabae were above 70%,among them,compound A6 with the inhibition rate of 99.03%as the best one.Three compounds had more than 50%inhibition rate against Tetranychus urticae,compound A5 havig a inhibition rate of 100%as the the optimal one.