取代双吡唑类化合物的合成及杀虫活性

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

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。

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.