Synthesis and insecticidal activities of novel N-sulfenyl-N'-tert-butyl-N,N'-diacylhydrazines. 2. N-substituted phenoxysulfenate derivatives.
A series of novel N-substituted phenoxysulfenyl- N'- tert-butyl- N, N'-diacylhydrazines were designed and synthesized as insect growth regulators via the key intermediates N-chlorosulfenyl- N'- tert-butyl- N, N'-diacylhydrazines. Compared to the parent compounds, these N-substituted phenoxysulfenyl 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-(4-chlorophenoxy)sulfenyl -N'- tert-butyl- N-4-ethylbenzoyl- N'-3,5-dimethylbenzoylhydrazide ( IIIi) as a field testing candidate has higher stomach toxicities against oriental armyworm and tobacco cutworm than the corresponding parent compound RH-5992. Furthermore, the compound IIIi exhibits higher contact activities against Asian corn borer, tobacco cutworm, and cotton bollworm than RH-5992.
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
Huang
Zhiqiang
Z
Wang
Kaiyun
K
Bi
Fuchun
F
Huang
Runqiu
R
Wang
Qingmin
Q
D000818:Animals; D001681:Biological Assay; D006834:Hydrazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D057927:Hydrophobic and Hydrophilic Interactions; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects*; D013270:Stomach / Q000187:drug effects; D013329:Structure-Activity Relationship
D006834:Hydrazines; D007306:Insecticides; C042228:N,N'-diacetylhydrazine