156778-34-6Relevant articles and documents
Design, Synthesis, Acaricidal Activities, and Structure-Activity Relationship Studies of Novel Oxazolines Containing Sulfonate Moieties
Chen, Shilin,Zhang, Yu,Liu, Yuxiu,Wang, Qingmin
, p. 13544 - 13549 (2019)
With the ultimate goal of addressing pest-related constraints on global agricultural production, we used combination principles to design and synthesize 2,4-diphenyl-1,3-oxazolines containing a sulfonate moiety at the para-position of the 4-phenyl group. The target compounds, which have strong affinity for lipids and can be expected to traverse cell membranes, were characterized by 1H and 13C NMR spectroscopy and high-resolution mass spectrometry. Their activities against the larvae and eggs of carmine spider mites (Tetranychus cinnabarinus) were determined by a leaf-dipping method and compared with the activity of the commercial acaricide etoxazole. Most of the test compounds displayed good ovicidal and larvicidal activities. In particular, a tert-butylphenyl-substituent compound possessed better larvicidal activity (LC50 = 0.022 ± 0.009 mg/L) and ovicidal activity (0.044 ± 0.020 mg/L) than etoxazole (0.091 ± 0.051 and 0.095 ± 0.059 mg/L, respectively). Given its outstanding bioactivities, this compound deserves further attention as a pesticide candidate.
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)
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/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)
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.
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 (2019/04/27)
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.
Etoxazole hapten, and synthesis method and application thereof
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Paragraph 0039; 0040; 0041, (2019/10/02)
The invention discloses an etoxazole hapten, and a synthesis method and an application thereof. The synthesis method comprises the following steps: synthesizing an intermediate 1 from 2,6-difluorobenzamide and 2-chloro-1,1-dimethoxyethane which are used a
Fluorobenzene oxazole compound and application thereof
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Paragraph 0023; 0024; 0025, (2016/10/10)
The invention discloses a fluorobenzene oxazole compound of which the structure is shown in a formula I and application thereof (Please see the formula in the description.). The compound has excellent inhibiting and killing effects on pest mites and mite
N-alkoxymethyl benzamide derivative and manufacturing method therefor, and manufacturing method for benzamide derivative using this N-alkoxymethyl benzamide derivate
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, (2008/06/13)
An N-alkoxymethyl benzamide derivative represented by Formula (I); (In the formula, reference X indicates a halogen atom, references Y1 and Y2 indicate hydrogen atoms or halogen atoms, and may be identical or different, and reference
