取代双吡唑类化合物的合成及杀虫活性

以3-氯苯肼盐酸盐( 1 )和1,1,3,3-四甲氧基丙烷( 2 )为起始原料,经环化、Vilsmeier反应得1-(3-氯苯基)-1H-吡唑-4-甲醛( 4);(4 )与3-三氟甲基苯乙酮( 5 )经Claisen-Schmidt缩合反应得取代芳基烯酮类化合物( 6 ),再与水合肼发生环化反应得3-(3-三氟甲基苯基)-5-(3-氯苯基-1H-吡唑)-4,5-二氢吡唑( 7),其与取代异氰酸酯 作用,制得15个未见文献报道的结构新颖的取代双吡唑类化合物。利用核磁共振氢谱(1H NMR)和质谱(MS)对其结构进行了表征。初步生物活性测定结果表明,在 500 mg/L 质量浓度下,部分化合物对小菜蛾Plutella xylostella的致死率达100%,而对苜蓿蚜Aphis medicaginis、稻褐飞虱Nilaparvata lugens、朱砂叶螨Tetranychus cinnabarinus均无杀虫活性。

Synthesis and insecticidal activity of a series of novel substituted bipyrazole compounds

1-(3-chlorophenyl)-1H-pyrazole-4-carbaldehyde( 4 ) was synthesized with cyclization and Vilsmeier reaction using 1-(3-chlorophenyl)hydrazine hydrochloride( 1 ) and 1,1,3,3-tetrame-thoxypropane ( 2 ) as raw materials.Claisen-Schmidt reaction of ( 4 ) with 1-(3-(trifluoromethyl) phenyl) ethanone( 5 ) afforded substituted arylketenes( 6 ).Then 3-(3-trifluoromethylphenyl)-5-(3-chlorophenyl-1H-pyrazol)-4,5-dihydropyrazole( 7 ) was obtained by cyclization of 6 with hydrazine hydrate from which 15 novel title compounds ( ZJ1-15 ) were synthesized with isocyanates ( 8 ).The structures of the compounds were confirmed by MS and ¹H NMR.The preliminary biological activity showed that the mortality ratio of some compounds against Plutella xylstella were 100% at concentration of 500 mg/L.All the compounds possessed no insecticidal activities against Aphimedicaginis,Nilaparvata lugens or Tetranychus cinnabarinus.