Design, Synthesis, and Acaricidal/Insecticidal Activities of Oxazoline Derivatives Containing a Sulfur Ether Moiety.
On the basis of etoxazole, a series of novel 2-(2,6-difluorophenyl)-4-(4-substituted phenyl)-1,3-oxazolines containing a sulfur ether moiety were designed and synthesized via the key intermediate N-(1-(4-(bromomethyl)phenyl)-2-chloroethyl)-2,6-difluorobenzamide. The bioassay results showed that most of these designed target compounds exhibited excellent acaricidal activity against both the eggs and larvae of Tetranychus cinnabarinus, especially the eggs. Among compounds with high activity against the eggs of mites, the LC50 values of 2, 11, 17, and 19 were 0.0003, 0.0002, 0.0005, and 0.0008 mg L(-1), respectively, much lower than that of etoxazole (0.0089 mg L(-1)). Compound 2 was chosen to evaluate the acaricidal activity in the field, and the results displayed that at a concentration of 22 mg kg(-1), 2 had a much better control effect than etoxazole against both T. cinnabarinus and P. latus on eggplant. Some compounds also showed good insecticidal activities against oriental armyworm and mosquito. On the basis of our research, the newly found structure-activity relationship may guide the development of new acaricides/pesticides that are required in the agriculture market.
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, People's Republic of China.
Xiuling
X
Yu
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, People's Republic of China.
Yuxiu
Y
Liu
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, People's Republic of China.
Yongqiang
Y
Li
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, People's Republic of China.
Qingmin
Q
Wang
D056810:Acaricides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D001042:Aphids / Q000187:drug effects; D015195:Drug Design; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007814:Larva / Q000187:drug effects; D008925:Mites / Q000187:drug effects; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects; D013329:Structure-Activity Relationship; D013440:Sulfides / Q000737:chemistry* / Q000494:pharmacology*
D056810:Acaricides; D007306:Insecticides; D013440:Sulfides
2,4-diphenyl-1,3-oxazolines; acaricidal activity; insecticidal activity; structure−activity relationship; thioether