Diamide compounds such as chlorantraniliprole,a famous anthranilic diamide insecticide targeting the insect ryanodine receptor(Ry R),have received continuous attention in pesticide research during the past 15 years ow...Diamide compounds such as chlorantraniliprole,a famous anthranilic diamide insecticide targeting the insect ryanodine receptor(Ry R),have received continuous attention in pesticide research during the past 15 years owing to their excellent insecticidal potentials.With the aim of discovering new heterocyclic pesticides used for crop protection,based on the structural information of compound M from the reported pharmacophore-based virtual screening for Ry R insecticides and diamide compound,a series of new heterocyclic mono-,di-,and tri-amide derivatives containing piperazine moiety have been synthesized in this paper.The new compounds were identified and confirmed by melting point,^(1)H NMR,^(13)C NMR and HRMS.Compound M was firstly validated for insecticidal activities,and the new synthesized compounds were all made comprehensive insecticidal evaluations against diamondback moth and oriental armyworm.The bioassay results showed that some of the compounds exhibit favorable insecticidal potentials,particularly some novel piperazine-containing heterocyclic mono-/di-/tri-amide derivatives such as 8 g,14 a,15 a,15 g,15 i,15 j,15 k,15 l,and 15 m could be used as new insecticidal leading structures for further study(e.g.,towards diamondback moth,15i-15 m LC_(50):0.0022-0.0081 mg/L).The structure-activity relationships of the compounds discussed in detail provide useful guidance for further design and development of new insecticides.展开更多
Fifteen novel N-sulfonyl aromatic amide derivatives were designed and synthesized, and the structures were characterized by 1H-and 13C-NMR, EA and HRMS. The crystal structures of compounds I-8 and I-9 were obtained fr...Fifteen novel N-sulfonyl aromatic amide derivatives were designed and synthesized, and the structures were characterized by 1H-and 13C-NMR, EA and HRMS. The crystal structures of compounds I-8 and I-9 were obtained from X-ray diffraction: I-8 is of triclinic system, Mr = 372.35, space group P2_(1/n) with a = 7.9151(10), b = 8.5637(11), c = 12.2022(15) A, β = 86.865(2)o, V = 807.09(18) A^(3), Z = 2, F(000) = 384, D_(c) = 1.532 g/cm^(3), the final R = 0.0408 and wR = 0.1068 for 2836 unique reflections with 2435 observed ones(I > 2σ(I)). I-9 belongs to triclinic system, M_r = 407.39, space group P2_1/n, with a = 8.4911(8), b = 8.6053(9), c = 14.5808(15) A, β = 77.1190(10)o, V = 995.44(17)A^(3), Z = 2, F(000) = 416, D_(c) = 1.359 g/cm^(3), the final R = 0.0567 and wR = 0.1779 for 3475 unique reflections with 2392 observed ones(I > 2σ(I)). The preliminary bioassay results indicated that the target compounds showed weak nematicidal activity, while compound I-5 displayed good fungicidal activity against Colletotrichum capsici with the inhibition rate of 61.7%.展开更多
基金financially supported by the National Key Research and Development Program of China(No.2017YFD0200505)the National Natural Science Foundation of China(No.21772103)。
文摘Diamide compounds such as chlorantraniliprole,a famous anthranilic diamide insecticide targeting the insect ryanodine receptor(Ry R),have received continuous attention in pesticide research during the past 15 years owing to their excellent insecticidal potentials.With the aim of discovering new heterocyclic pesticides used for crop protection,based on the structural information of compound M from the reported pharmacophore-based virtual screening for Ry R insecticides and diamide compound,a series of new heterocyclic mono-,di-,and tri-amide derivatives containing piperazine moiety have been synthesized in this paper.The new compounds were identified and confirmed by melting point,^(1)H NMR,^(13)C NMR and HRMS.Compound M was firstly validated for insecticidal activities,and the new synthesized compounds were all made comprehensive insecticidal evaluations against diamondback moth and oriental armyworm.The bioassay results showed that some of the compounds exhibit favorable insecticidal potentials,particularly some novel piperazine-containing heterocyclic mono-/di-/tri-amide derivatives such as 8 g,14 a,15 a,15 g,15 i,15 j,15 k,15 l,and 15 m could be used as new insecticidal leading structures for further study(e.g.,towards diamondback moth,15i-15 m LC_(50):0.0022-0.0081 mg/L).The structure-activity relationships of the compounds discussed in detail provide useful guidance for further design and development of new insecticides.
基金supported by the National Natural Science Foundation of China(32001929)the Natural Science Foundation of Shandong Province(ZR2017BC053)the Innovation and Entrepreneurship Training Program for College Students of Liaocheng University(CXCY2020Y116)。
文摘Fifteen novel N-sulfonyl aromatic amide derivatives were designed and synthesized, and the structures were characterized by 1H-and 13C-NMR, EA and HRMS. The crystal structures of compounds I-8 and I-9 were obtained from X-ray diffraction: I-8 is of triclinic system, Mr = 372.35, space group P2_(1/n) with a = 7.9151(10), b = 8.5637(11), c = 12.2022(15) A, β = 86.865(2)o, V = 807.09(18) A^(3), Z = 2, F(000) = 384, D_(c) = 1.532 g/cm^(3), the final R = 0.0408 and wR = 0.1068 for 2836 unique reflections with 2435 observed ones(I > 2σ(I)). I-9 belongs to triclinic system, M_r = 407.39, space group P2_1/n, with a = 8.4911(8), b = 8.6053(9), c = 14.5808(15) A, β = 77.1190(10)o, V = 995.44(17)A^(3), Z = 2, F(000) = 416, D_(c) = 1.359 g/cm^(3), the final R = 0.0567 and wR = 0.1779 for 3475 unique reflections with 2392 observed ones(I > 2σ(I)). The preliminary bioassay results indicated that the target compounds showed weak nematicidal activity, while compound I-5 displayed good fungicidal activity against Colletotrichum capsici with the inhibition rate of 61.7%.
