Characteristics and Ring-Opening Isomerization Polymerization of 2-(1,3,3-Trimethyl-6-azabicyclo[3,2,1]-oct-6-yl)-4,5-dihydro-1,3-oxazoline (TAO)

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, 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.

Section: ■ Introductionmentioning

confidence: 99%

Design, Synthesis, Acaricidal Activity, and Mechanism of Oxazoline Derivatives Containing an Oxime Ether Moiety

Zheng

et al. 2014

“…Gernerally, all compounds exhibited better ovicidal activity than larvicidal activity. Compounds 2,3,6,7,10,11,16,17, and 19−23 gave 100% mortality against eggs at 1 mg L −1 , so these compounds were further assayed at lower concentrations and LC 50 values were calculated (Table 2). LC 50 values of the target compounds 2 and 3, substituted at the para position of 4-phenyl moiety with a (benzothiazole)thiomethyl group and (benzooxazole)thiomethyl group, respectively, were 0.0003 mg L −1 and 0.0037 mg L −1 , both lower than that of other heterocyclic aryl sulfide compounds and etoxazole (0.0089 mg L −1 ).…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…Most of the designed compounds showed excellent acaricidal activity, and the results also showed that the positions and types of substituents on the 4-phenyl moiety of 1,3-oxazolines had a great influence on the acaricidal and insecticidal activities. 10,11 In 2014, we further reported a series of 1,3-oxazolines with an oxime ether substituent at the para position of the 4-phenyl moiety. The bioassay results indicated that all of the target compounds exhibited considerable acaricidal activity against T. cinnabarinus.…”

Section: ■ Introductionmentioning

confidence: 96%

“…Recently, our research group reported the synthesis and acaricidal/insecticidal activities of oxazoline compounds in which a substituted phenoxy or a different alkoxy group was fixed at the para position of the 4-phenyl moiety (part C), optionally with Cl, methyl, or ethoxy at the ortho position and/or meta position. Most of the designed compounds showed excellent acaricidal activity, and the results also showed that the positions and types of substituents on the 4-phenyl moiety of 1,3-oxazolines had a great influence on the acaricidal and insecticidal activities. , In 2014, we further reported a series of 1,3-oxazolines with an oxime ether substituent at the para position of the 4-phenyl moiety. The bioassay results indicated that all of the target compounds exhibited considerable acaricidal activity against T. cinnabarinus .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Design, Synthesis, and Acaricidal/Insecticidal Activities of Oxazoline Derivatives Containing a Sulfur Ether Moiety

Liu

et al. 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.

“… In 2004, Matsumura and co-workers by isotope-labeling experiments found that the benzoylurea insecticide diflubenzuron and antidiabetic glibenclamide both targeted the SUR protein in Drosophila melanogaster and Blattella germanica; such binding made chitin not be biosynthesized normally. , In 2012, Van Leeuwen et al also used the technology of calcofluor white (CFW) staining to demonstrate that etoxazole indeed inhibited chitin biosynthesis in Tetranychus urticae . According to the similarity in the action mechanism of the 2,4-diphenyl-1,3-oxazolines and benzoylureas, both belonging to chitin synthesis inhibitors (CSIs), , our research group preliminarily determined the binding affinity of etoxazole and oxazoline derivatives to SUR in vitro by the fluorescence polarization method and found that the trend of their binding affinity was almost consistent with their acaricidal activities against Tetranychus cinnabarinus in vivo . Therefore, it was verified that oxazoline derivatives, including etoxazole, could bind with SUR, resulting in the inhibition of chitin biosynthesis in the mite body .…”

Section: Introductionmentioning

confidence: 99%

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

Liu

et al. 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 (1)H and (13)C 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.