title: Synthesis and insecticidal activities of novel N-sulfenyl-N'-tert-butyl-N,N'-diacylhydrazines. 1. N-alkoxysulfenate derivatives.
abstract: A series of novel N-alkoxysulfenyl-N'-tert-butyl-N, N'-diacylhydrazines were designed and synthesized as insect growth regulators by the key intermediates N-chlorosulfenyl-N'-tert-butyl-N, N'-diacylhydrazines, which were prepared for the first time. Compared to N'-tert-butyl-N, N'-diacylhydrazines, these N-alkoxysulfenyl derivatives displayed better solubility and improved hydrophobicities. The insecticidal activities of the new compounds were evaluated. The results of bioassays showed that the title compounds possessed a combination of strong stomach as well as contact poison property higher than the corresponding parent compounds. In particular, N-methoxysufenyl-N'-tert-butyl-N-4-ethylbenzoyl-N'-3,5-dimethylbenzoylhydrazide (IIIf) as a field testing candidate has higher stomach toxicities against oriental armyworm and beet armyworm than the corresponding parent compound RH-5992. Furthermore, the compound IIIf exhibits higher contact activities against oriental armyworm, Asian corn borer, tobacco cutworm, and cotton bollworm than RH-5992. The sulfenyl substituent was essential for high larvacidal activity.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
authors.forename: Qiqi
authors.initials: Q
authors.lastname: Zhao
authors.forename: Jian
authors.initials: J
authors.lastname: Shang
authors.forename: Yuxiu
authors.initials: Y
authors.lastname: Liu
authors.forename: Kaiyun
authors.initials: K
authors.lastname: Wang
authors.forename: Fuchun
authors.initials: F
authors.lastname: Bi
authors.forename: Runqiu
authors.initials: R
authors.lastname: Huang
authors.forename: Qingmin
authors.initials: Q
authors.lastname: Wang
mesh_terms: D000818:Animals; D006834:Hydrazines / Q000138:chemical synthesis* / Q000737:chemistry; D007306:Insecticides / Q000138:chemical synthesis*; D007814:Larva; D007915:Lepidoptera; D013416:Sulfamerazine
chemical_list: D006834:Hydrazines; D007306:Insecticides; C012049:sulfaperine; C082026:tebufenozide; D013416:Sulfamerazine