Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl-N'-sulfenylureas.
A series of new N'-alkylaminothio, N'-arylaminothio (or dithio), and N',N'-thio (or dithio) derivatives of N-benzoyl-N'-phenylureas were designed and synthesized as insect-growth regulators with sulfur dichloride or disulfur dichloride as the original reactant. The new compounds were identified by (1)H nuclear magnetic resonancee (NMR) spectroscopy, elemental analysis [or high-resolution mass spectrometry (HRMS)], and single-crystal X-ray diffraction analysis. The X-ray results demonstrated that there exist N-S-N or N-S-S-N bonds in these new compounds. In comparison to the parent N-benzoyl-N'-phenylureas, these derivatives displayed better solubility. The insecticidal activities of the target compounds were evaluated. The results of bioassays showed that compounds 1-24 retained the larvicidal activities of the corresponding benzoylphenylureas (BPUs) and some compounds exhibited better larvicidal activities against oriental armyworm and mosquitoes than the parent BPUs. The larvicidal activities of the selected target compounds 1 and 24 against diamondback moth were better than that of the corresponding parent compounds E and triflumuron.
Sun
Ranfeng
R
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
Zhang
Yonglin
Y
Chen
Li
L
Li
Yongqiang
Y
Li
Qingshan
Q
Song
Haibin
H
Huang
Runqiu
R
Bi
Fuchun
F
Wang
Qingmin
Q