1586758-91-9Relevant academic research and scientific papers
Synthesis and Acaricidal- and Insecticidal-Activity Evaluation of Novel Oxazolines Containing Sulfiliminyl Moieties and Their Derivatives
Yu, Xiuling,Zhang, Yu,Liu, Yuxiu,Li, Yongqiang,Wang, Qingmin
, p. 4224 - 4231 (2019)
Sulfimides and sulfoximines are highly relevant for medicinal chemistry and crop protection, as the resulting products can reveal interesting bioactivities. Herein, we report the design and synthesis of a series of novel 2,4-diphenyl-1,3-oxazolines containing sulfiliminyl and sulfoximinyl moieties. The acaricidal and insecticidal activities of the new compounds were evaluated and indicated that these compounds exhibited excellent acaricidal activities against spider mite larvae and eggs. The LC50 values of 6a-7, 6b-3, 6b-4, 6c-2, and 6c-4 against spider mite larvae were about 4 to 6 times lower than that of the commercial insecticide etoxazole (0.0221 mg L-1), and the LC50 value of 6a-4 against spider mite eggs was 0.0006 mg L-1, which was 10 times lower than that of etoxazole (0.0063 mg L-1). At the same time, most of the compounds showed insecticidal activity though their structure-activity relationships that were different. Oxazolines containing an N-cyano sulfiliminyl moiety at the para position of the 4-phenyl group exhibited better insecticidal activities against cotton bollworm and corn borer than etoxazole, whereas the compounds containing groups derived from sulfiliminyl and sulfoximinyl had weak insecticidal activities. This research again proved that the substituent type at the para site of the 4-phenyl moiety has a decisive role on the biological activity and insecticidal spectrum.
Design, Synthesis, Acaricidal/Insecticidal Activity, and Structure-Activity Relationship Studies of Novel Oxazolines Containing Sulfone/Sulfoxide Groups Based on the Sulfonylurea Receptor Protein-Binding Site
Yu, Xiuling,Liu, Yuxiu,Li, Yongqiang,Wang, Qingmin
, p. 3034 - 3040 (2016/05/19)
Enormous compounds containing sulfone/sulfoxide groups have been used in a variety of fields, especially in drug and pesticide design. To search for novel environmentally benign and ecologically safe pesticides with unique modes of action, a series of 2,4-diphenyl-1,3-oxazolines containing sulfone/sulfoxide groups as chitin synthesis inhibitors (CSIs) were designed and synthesized on the basis of the sulfonylurea receptor protein-binding site for CSIs. Their structures were characterized by 1H and 13C nuclear magnetic resonance and high-resolution mass spectrometry. The acaricidal and insecticidal activities of the new compounds were evaluated. It was found that most of the target compounds displayed wonderful acaricidal activities against spider mite (Tetranychus cinnabarinus) larvae and eggs. Especially compounds I-4, II-3, and II-4 displayed higher activities than commercial etoxazole at a concentration of 2.5 mg L-1. Some target compounds exhibited insecticidal activities against lepidopteran pests. The present work demonstrated that these compounds containing sulfone/sulfoxide groups could be considered as potential candidates for the development of novel acaricides in the future.
Design, Synthesis, and Acaricidal/Insecticidal Activities of Oxazoline Derivatives Containing a Sulfur Ether Moiety
Yu, Xiuling,Liu, Yuxiu,Li, Yongqiang,Wang, Qingmin
, p. 9690 - 9695 (2015/11/24)
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.
Design, synthesis, acaricidal activity, and mechanism of oxazoline derivatives containing an oxime ether moiety
Li, Yongqiang,Li, Chaojie,Zheng, Yanlong,Wei, Xingcun,Ma, Qiaoqiao,Wei, Peng,Liu, Yuxiu,Qin, Yaoguo,Yang, Na,Sun, Yufeng,Ling, Yun,Yang, Xinling,Wang, Qingmin
, p. 3064 - 3072 (2014/05/06)
Two series of novel 2,4-diphenyl-1,3-oxazolines containing an oxime ether moiety were designed and synthesized via the key intermediate N-(2-chloro-1-(p-tolyl)ethyl)-2,6-difluorobenzamide. The bioassay results showed that the target compounds with an oxime ether substituent at the para position of 4-phenyl exhibited excellent acaricidal activity against Tetranychus cinnabarinus in the laboratory. Moreover, all of the target compounds had much higher activities than etoxazole, as the ovicidal and larvicidal activities of the target compounds I-a-I-l and II-a-II-n against T. cinnabarinus were all over 90% at 0.001 mg L-1, but etoxazole gave only 30% and 40% respectively at the same concentration. The activity order of compounds with regard to acaricidal activity in vivo was almost consistent with their affinity activity with sulfonylurea receptor (SUR) of Blattella germanica in vitro, hence, it was supposed that the acaricidal mechanism of action of the target compounds was that they can bind with the site of SUR and therefore inhibit chitin synthesis. Moreover, the eminent effect of the compound II-l, [2-(trifluoromethyl)benzaldehyde O-(4-(2-(2,6-difluorophenyl)-4,5-dihydrooxazol- 4-yl)benzyl) oxime], against Panonychus citri and T. cinnabarinus in the field indicated that II-l exhibited a promising application prospect as a new candicate for controlling spider mites in the field.
Design, synthesis, acaricidal activity, and mechanism of oxazoline derivatives containing an oxime ether moiety
Li, Yongqiang,Li, Chaojie,Zheng, Yanlong,Wei, Xingcun,Ma, Qiaoqiao,Wei, Peng,Liu, Yuxiu,Qin, Yaoguo,Yang, Na,Sun, Yufeng,Ling, Yun,Yang, Xinling,Wang, Qingmin
, p. 3064 - 3072 (2015/04/22)
Two series of novel 2,4-diphenyl-1,3-oxazolines containing an oxime ether moiety were designed and synthesized via the key intermediate N-(2-chloro-1-(p-tolyl)ethyl)-2,6-difluorobenzamide. The bioassay results showed that the target compounds with an oxime ether substituent at the para position of 4-phenyl exhibited excellent acaricidal activity against Tetranychus cinnabarinus in the laboratory. Moreover, all of the target compounds had much higher activities than etoxazole, as the ovicidal and larvicidal activities of the target compounds I-a-I-l and II-a-II-n against T. cinnabarinus were all over 90% at 0.001 mg L-1, but etoxazole gave only 30% and 40% respectively at the same concentration. The activity order of compounds with regard to acaricidal activity in vivo was almost consistent with their affinity activity with sulfonylurea receptor (SUR) of Blattella germanica in vitro, hence, it was supposed that the acaricidal mechanism of action of the target compounds was that they can bind with the site of SUR and therefore inhibit chitin synthesis. Moreover, the eminent effect of the compound II-l, [2-(trifluoromethyl)benzaldehyde O-(4-(2-(2,6-difluorophenyl)-4,5-dihydrooxazol-4-yl)benzyl) oxime], against Panonychus citri and T. cinnabarinus in the field indicated that II-l exhibited a promising application prospect as a new candicate for controlling spider mites in the field.
