Synthesis and insecticidal activities of novel N-sulfenyl-N'-tert-butyl-N,N'-diacylhydrazines. 1. N-alkoxysulfenate derivatives.
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.
Zhao
Qiqi
Q
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
Shang
Jian
J
Liu
Yuxiu
Y
Wang
Kaiyun
K
Bi
Fuchun
F
Huang
Runqiu
R
Wang
Qingmin
Q
D000818:Animals; D006834:Hydrazines / Q000138:chemical synthesis* / Q000737:chemistry; D007306:Insecticides / Q000138:chemical synthesis*; D007814:Larva; D007915:Lepidoptera; D013416:Sulfamerazine
D006834:Hydrazines; D007306:Insecticides; C012049:sulfaperine; C082026:tebufenozide; D013416:Sulfamerazine