Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by 1H NMR spectroscopy, elemental analysis and single crystal ...Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by 1H NMR spectroscopy, elemental analysis and single crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities. The insecticidal activities of compounds 19a, 19b, 19d, 19g, 19k and 19m against oriental armyworm at 2.5 mg·kg-1 were 100%. The larvicidal activities of 19a, 19b, 19c, 19d, 19e, 19g and 19n against diamond-back moth were 100% at 0.1 mg·kg-1. Surprisingly, most of them still exhibited perfect insecticidal activity against diamond-back moth when the concentration was reduced to 0.05 mg·kg-1, which was higher than the commercialized Chlorantraniliprole.展开更多
In search of environmentally benign insecticides with high activity, low toxicity and low residue, a series of novel anthranilic diamide derivatives containing N-pyridylpyrazole was designed and synthesized. All the c...In search of environmentally benign insecticides with high activity, low toxicity and low residue, a series of novel anthranilic diamide derivatives containing N-pyridylpyrazole was designed and synthesized. All the compounds were characterized by H NMR spectroscopy and elemental analysis. The single crystal structure of com pound 8j was determined by X-ray diffraction. The insecticidal activities of the new compounds were evaluated. The results show that some compounds exhibited moderate insecticidal activities against Lepidoptera pests. Among this series of compounds, compounds 80 and 8p showed 100% larvicidal activity against Mythimna separate Walker, Plutella xylostella Linnaeus and Laphygma exigua Hubner at a test concentration of 200 mg/kg, which is equal to the commercial chlorantraniliprole.展开更多
Two series of novel anthranilic diamides containing oxime ester and diacylhydrazine moieties were designed and synthesized.Their structures were characterized by melting points,1H NMR,13C NMR and high resolution mass ...Two series of novel anthranilic diamides containing oxime ester and diacylhydrazine moieties were designed and synthesized.Their structures were characterized by melting points,1H NMR,13C NMR and high resolution mass spectrometry（HRMS）.The single crystal structure of compound 7e was determined by X-ray diffraction and their evaluated insecticidal activity against oriental armyworm（Mythimna separata） indicates that some of the compounds exhibited moderate insecticidal activities.Among the 20 compounds,6a and 6b show 100％ larvicidal activity against Mythimna separate Walker at the test concentration of 100 mg/L.展开更多
To study the pesticide effect, action mode, structure-activity relationships (SARs) of anthranilic diamide insecticide and screen highly active pesticides, novel anthranilic diamide derivatives were synthesized.Bioass...To study the pesticide effect, action mode, structure-activity relationships (SARs) of anthranilic diamide insecticide and screen highly active pesticides, novel anthranilic diamide derivatives were synthesized.Bioassays indicated that all of the title compounds displayed 100% mortality against diamondback moth and oriental armyworm at 100 mg/L, among which 12 v and 12 w showed 100% insecticidal acitvity at 5 mg/L. Surprisingly compound 12 w exhibited better insecticidal acitvity than commercialized chlorantraniliprole against Pyrausta nubilalis (0.1 mg/L) and Cnaphalocrocis Medinalis (2 mg/L). 3 D-QSAR and SARs statistical analysis revealed that title compounds with R^2 fixed as methoxy had the highest probability possessing high activity. The calcium fluorescence measurements on neurons revealed that E series compounds containing pyrazinyl may have a molecular target different from caffeine on ryanodine receptors rather than the voltage-gated calcium channel present on cytomembran.展开更多
A series of novel anthranilic diamides analogues containing benzo[b]thiophenyl ring was designed and synthesized. Their structures were characterized by melting points, 1H nuclear magnetic resonance（IH NMR） and high...A series of novel anthranilic diamides analogues containing benzo[b]thiophenyl ring was designed and synthesized. Their structures were characterized by melting points, 1H nuclear magnetic resonance（IH NMR） and high-resolution mass spectrometry（HRMS）. The bioassay tests indicate that their insecticidal activities were weak to moderate. Antibacterial tests indicate that some of the compounds showed favourable activity in vitro against Physa- lospora piricola, Alternaria solani, Cercospora arachidicola, Gibberella sanbinetti and Phytophthora infestans at a dosage of 50 mg/L.展开更多
Thirteen novel phenyl substituted isoxazolecarboxamides were synthesized, and their structures were characterized by IH NMR, elementary analysis and high-resolution mass spectrometry（HRMS） techniques. Their evaluate...Thirteen novel phenyl substituted isoxazolecarboxamides were synthesized, and their structures were characterized by IH NMR, elementary analysis and high-resolution mass spectrometry（HRMS） techniques. Their evaluated insecticidal activities against oriental armyworm（Mythimna separata） indicate that the phenyl substituted isoxazolecarboxamides exhibited moderate insecticidal activities, among which compounds 9c and 9k showed com- paratively higher activities.展开更多
To further explore the structure-activity relationship（SAR） of amide bridge moeity of anthranilic diamides derivatives, a series of N-pyridylpyrazole derivatives was designed, synthesized and their biological activi...To further explore the structure-activity relationship（SAR） of amide bridge moeity of anthranilic diamides derivatives, a series of N-pyridylpyrazole derivatives was designed, synthesized and their biological activities were evaluated. The chemical structures of novel target compounds were confirmed by 1H nuclear magnetic resonance （N-MR）, 13C NMR and elemental analyses（EA）. Bioassay results of insecticidal activity demonstrated that the target compound 6h displayed 70% lethality rate against oriental armyworms at 200 mg/L. Moreover, most compounds displayed moderate to excellent antifungicidal activities against Fusarium oxysporumf sp. cucumerinum, Cercospora arachidicola Hori, Botryosphaeria dothidea, Alternaria solani, Gibberella zeae and Phytophthora capsici at 50 mg/L In particular, compound 6e showed 61.5% and 92.3% inhibition rate against Cercospora arachidicola Hori and Botryosphaeria dothidea, which was superior to the commercial positive control Chlorothalonil. These results will provide a potential clue for exploring novel high-effective agrochemicals.展开更多
Twelve novel analogues of chlorantraniliprole containing nitro group were synthesized,and their structures were characterized by 1H NMR and high-resolution mass spectrometry（HRMS）.Their evaluated insecticidal activi...Twelve novel analogues of chlorantraniliprole containing nitro group were synthesized,and their structures were characterized by 1H NMR and high-resolution mass spectrometry（HRMS）.Their evaluated insecticidal activities against oriental armyworm（Mythimna separata） indicate that the nitro-containing analogues showed favorable insecticidal activities,while the activity of compounds 5g at 0.25mg/L was 40%,but still lower than chlorantraniliprole.展开更多
Anthranilic diamides are one of the most important classes of modern agrochemical insecticides. To discover new structures with higher activity, lower toxicity and lower residue, a series of novel anthranilic diamides...Anthranilic diamides are one of the most important classes of modern agrochemical insecticides. To discover new structures with higher activity, lower toxicity and lower residue, a series of novel anthranilic diamides containing dihydroisoxazoline and isoxazole was designed and synthesized. Their structures were characterized by means of melting points, proton nuclear magnetic resonance（IH NMR）, 13C NMR and high resolution mass spectrometry（HRMS）. According to the bioassay data, it was found that some of the title compounds exhibit moderate insecticidal activity and good antifungal activity. In particularly, compound 15b with a concentration of 50 mg/L shows a lethality rate of 60.0% against Mythimna separata Walker and a lethality rate of 50.0% against Culex pipiens pallens with a concentration of 1 mg/L. Moreover, compound 15b showed good antifungal activities（58.8%, 77.1%, 70.7%, 55.3%, 60.7%, 65.4%） when against all the tested fungi（Cercospora araehidicola tIori, Physalospora piricola, Rhizoctonia cerealis, Bipolaris maydis, Watermelon anthracnose, Fusarium moniliforme）. The effects of compounds 14h, 14j and 15b on the concentration of intracellular calcium ion（[Ca2＋]i） in the central neurons of Mythimna separate Walker were well investigated via calcium imaging technique. The results demonstrate that the novel compounds can elevate the calcium concentration in the neurons, denoting that some new structures are potential modulators of the insect ryanodine receptor（RyR）.展开更多
文摘Two series of novel anthranilic diamide insecticide containing trifluoroethyl ether were designed and synthesized, and their structures were characterized by 1H NMR spectroscopy, elemental analysis and single crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities. The insecticidal activities of compounds 19a, 19b, 19d, 19g, 19k and 19m against oriental armyworm at 2.5 mg·kg-1 were 100%. The larvicidal activities of 19a, 19b, 19c, 19d, 19e, 19g and 19n against diamond-back moth were 100% at 0.1 mg·kg-1. Surprisingly, most of them still exhibited perfect insecticidal activity against diamond-back moth when the concentration was reduced to 0.05 mg·kg-1, which was higher than the commercialized Chlorantraniliprole.
文摘In search of environmentally benign insecticides with high activity, low toxicity and low residue, a series of novel anthranilic diamide derivatives containing N-pyridylpyrazole was designed and synthesized. All the compounds were characterized by H NMR spectroscopy and elemental analysis. The single crystal structure of com pound 8j was determined by X-ray diffraction. The insecticidal activities of the new compounds were evaluated. The results show that some compounds exhibited moderate insecticidal activities against Lepidoptera pests. Among this series of compounds, compounds 80 and 8p showed 100% larvicidal activity against Mythimna separate Walker, Plutella xylostella Linnaeus and Laphygma exigua Hubner at a test concentration of 200 mg/kg, which is equal to the commercial chlorantraniliprole.
基金Supported by the National Natural Science Foundation of China（Nos.21272129,21372133）,the National Basic Research Program of China（No.2010CB126106） and the National Key Technologies R＆D Program of China（No.2011BAE06B05）.
文摘Two series of novel anthranilic diamides containing oxime ester and diacylhydrazine moieties were designed and synthesized.Their structures were characterized by melting points,1H NMR,13C NMR and high resolution mass spectrometry（HRMS）.The single crystal structure of compound 7e was determined by X-ray diffraction and their evaluated insecticidal activity against oriental armyworm（Mythimna separata） indicates that some of the compounds exhibited moderate insecticidal activities.Among the 20 compounds,6a and 6b show 100％ larvicidal activity against Mythimna separate Walker at the test concentration of 100 mg/L.
基金supported by the National Natural Science Foundation of China(Nos. 20772060 and 21172114)
文摘To study the pesticide effect, action mode, structure-activity relationships (SARs) of anthranilic diamide insecticide and screen highly active pesticides, novel anthranilic diamide derivatives were synthesized.Bioassays indicated that all of the title compounds displayed 100% mortality against diamondback moth and oriental armyworm at 100 mg/L, among which 12 v and 12 w showed 100% insecticidal acitvity at 5 mg/L. Surprisingly compound 12 w exhibited better insecticidal acitvity than commercialized chlorantraniliprole against Pyrausta nubilalis (0.1 mg/L) and Cnaphalocrocis Medinalis (2 mg/L). 3 D-QSAR and SARs statistical analysis revealed that title compounds with R^2 fixed as methoxy had the highest probability possessing high activity. The calcium fluorescence measurements on neurons revealed that E series compounds containing pyrazinyl may have a molecular target different from caffeine on ryanodine receptors rather than the voltage-gated calcium channel present on cytomembran.
基金Supported by the National Natural Science Foundation of China（No.20872069）, the National Basic Research Program of China（No.2010CB 126106）, the National Key Technologies R＆D Program of China（No.2011BAE06B05）, the Tianjin Natural Science Foundation, China（No. 11JCYBJC08600） and the Fund of State Key Laboratory of Elemento-Organic Chemistry, China.
文摘A series of novel anthranilic diamides analogues containing benzo[b]thiophenyl ring was designed and synthesized. Their structures were characterized by melting points, 1H nuclear magnetic resonance（IH NMR） and high-resolution mass spectrometry（HRMS）. The bioassay tests indicate that their insecticidal activities were weak to moderate. Antibacterial tests indicate that some of the compounds showed favourable activity in vitro against Physa- lospora piricola, Alternaria solani, Cercospora arachidicola, Gibberella sanbinetti and Phytophthora infestans at a dosage of 50 mg/L.
基金Supported by the National Natural Science Foundation of China(No. 20872069)the National Basic Research Program of China(No.2010CB126106)the Fund of State Key Laboratory of Elemento-Organic Chemistry,China
文摘Thirteen novel phenyl substituted isoxazolecarboxamides were synthesized, and their structures were characterized by IH NMR, elementary analysis and high-resolution mass spectrometry（HRMS） techniques. Their evaluated insecticidal activities against oriental armyworm（Mythimna separata） indicate that the phenyl substituted isoxazolecarboxamides exhibited moderate insecticidal activities, among which compounds 9c and 9k showed com- paratively higher activities.
基金Supported by the National Natural Science Foundation of China（No.21502229）, the Natural Science Foundation of Shandong Province, China（No.ZR2017BC053） and the Doctoral Research Startup Foundation of Liaocheng University, China （No.318051625）.
文摘To further explore the structure-activity relationship（SAR） of amide bridge moeity of anthranilic diamides derivatives, a series of N-pyridylpyrazole derivatives was designed, synthesized and their biological activities were evaluated. The chemical structures of novel target compounds were confirmed by 1H nuclear magnetic resonance （N-MR）, 13C NMR and elemental analyses（EA）. Bioassay results of insecticidal activity demonstrated that the target compound 6h displayed 70% lethality rate against oriental armyworms at 200 mg/L. Moreover, most compounds displayed moderate to excellent antifungicidal activities against Fusarium oxysporumf sp. cucumerinum, Cercospora arachidicola Hori, Botryosphaeria dothidea, Alternaria solani, Gibberella zeae and Phytophthora capsici at 50 mg/L In particular, compound 6e showed 61.5% and 92.3% inhibition rate against Cercospora arachidicola Hori and Botryosphaeria dothidea, which was superior to the commercial positive control Chlorothalonil. These results will provide a potential clue for exploring novel high-effective agrochemicals.
基金Supported by the National Basic Research Program of China(No.2010CB126106)
文摘Twelve novel analogues of chlorantraniliprole containing nitro group were synthesized,and their structures were characterized by 1H NMR and high-resolution mass spectrometry（HRMS）.Their evaluated insecticidal activities against oriental armyworm（Mythimna separata） indicate that the nitro-containing analogues showed favorable insecticidal activities,while the activity of compounds 5g at 0.25mg/L was 40%,but still lower than chlorantraniliprole.
基金Supported by the National Basic Research Program of China（No.2010CB126106）, the National Natural Science Foundation of China（Nos.21272129, 31370039）, the National Key Technologies R＆D Program of China（No.2011BAE06B05） and the ＂111＂ Project of the Ministry of the Education of China（No.B06005）.
文摘Anthranilic diamides are one of the most important classes of modern agrochemical insecticides. To discover new structures with higher activity, lower toxicity and lower residue, a series of novel anthranilic diamides containing dihydroisoxazoline and isoxazole was designed and synthesized. Their structures were characterized by means of melting points, proton nuclear magnetic resonance（IH NMR）, 13C NMR and high resolution mass spectrometry（HRMS）. According to the bioassay data, it was found that some of the title compounds exhibit moderate insecticidal activity and good antifungal activity. In particularly, compound 15b with a concentration of 50 mg/L shows a lethality rate of 60.0% against Mythimna separata Walker and a lethality rate of 50.0% against Culex pipiens pallens with a concentration of 1 mg/L. Moreover, compound 15b showed good antifungal activities（58.8%, 77.1%, 70.7%, 55.3%, 60.7%, 65.4%） when against all the tested fungi（Cercospora araehidicola tIori, Physalospora piricola, Rhizoctonia cerealis, Bipolaris maydis, Watermelon anthracnose, Fusarium moniliforme）. The effects of compounds 14h, 14j and 15b on the concentration of intracellular calcium ion（[Ca2＋]i） in the central neurons of Mythimna separate Walker were well investigated via calcium imaging technique. The results demonstrate that the novel compounds can elevate the calcium concentration in the neurons, denoting that some new structures are potential modulators of the insect ryanodine receptor（RyR）.
