三嗪酮杀虫活性分子的合成及生物活性
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摘要
为发展更加高效的三嗪酮杀虫活性分子,本文设计合成了16种氨基部分被取代的三嗪酮衍生物,并测试了其杀虫、抑菌活性。杀虫活性测试表明:在浓度为600mg·kg~(-1)时,化合物N-(苯基氧羰基)-N-(6-甲基-3-氧代-2,3-二氢-1,2,4-三嗪-4(5H)-基)氨基甲酸苯酯(3e,100%、100%、100%)的杀棉铃虫、玉米螟、粘虫活性高于吡蚜酮(20%,35%,50%)。在浓度为0.5mg·kg~(-1)时,化合物3e(60%)的杀蚊幼虫活性高于吡蚜酮(0)。抑菌活性测试表明:三嗪酮酰胺衍生物对玉米小斑病菌和西瓜炭疽病菌表现出较高的抑菌活性;而三嗪酮亚胺衍生物对小麦纹枯病菌表现出较高的抑菌活性。
In order to develop high efficient triazone insecticidal active molecules,16 amino-substituted triazone derivatives were synthesized and their insecticidal and antifungal activities were tested.The results of insecticidal activities showed that compound phenyl N-phenyloxycarbonyl-N-(6-methyl-3-oxo-2,3-dihydro-1,2,4-triaziN-4(5H)-yl)carbamate(3 e,100%,100%,100%)showed higher insecticidal activities against cotton bollworm,corn borer,oriental armyworm than pymetrozine(20%,35%,50%)at 600 mg·kg~(-1).Compound 3 e(60%)showed higher larvicidal activity against mosquito than pymetrozine(0)at 0.5 mg·kg~(-1).The results of antifungal activities showed that triazone amide derivatives exhibited good antifungal activities against bipolaris maydis and watermelon anthracnose,while triazone imine derivatives exhibited good antifungal activities against rhizoctonia cerealis.
In order to develop high efficient triazone insecticidal active molecules,16 amino-substituted triazone derivatives were synthesized and their insecticidal and antifungal activities were tested.The results of insecticidal activities showed that compound phenyl N-phenyloxycarbonyl-N-(6-methyl-3-oxo-2,3-dihydro-1,2,4-triaziN-4(5H)-yl)carbamate(3 e,100%,100%,100%)showed higher insecticidal activities against cotton bollworm,corn borer,oriental armyworm than pymetrozine(20%,35%,50%)at 600 mg·kg~(-1).Compound 3 e(60%)showed higher larvicidal activity against mosquito than pymetrozine(0)at 0.5 mg·kg~(-1).The results of antifungal activities showed that triazone amide derivatives exhibited good antifungal activities against bipolaris maydis and watermelon anthracnose,while triazone imine derivatives exhibited good antifungal activities against rhizoctonia cerealis.
引文
[1]Adams C D,Cummins E W,Gleich S I.Process for preparing herbicidal triazine[P].US:4178448,1979-12-11.
[2]Ochomogo O R.Selective herbicide[P].US:4101308,1978-07-18.
[3]Wang B Z,Ke S Y,Kishore B B,et al.A facile synthesis of pyrimidone derivatives and single-crystal characterization of pymetrozine[J].Syn Commun,2012,42(16):2 327-2 336.
[4]Yang Y,Liu Y X,Song,H J,et al.Additive effects on the improvement of insecticidal activity:Design,synthesis,and insecticidal activity of novel pymetrozine derivatives[J].Bioorg Med Chem,2016,24(3):391-402.
[5]Yang Y,Huang Y Q,Song H J,et al.Skeletal modifications of β-carboline alkaloids and their antiviral activity study[J].Mol Divers,2016,20(4):829-835.
[6]Yang Y,Liu Y X,Song H J,et al.Design,synthesis,insecticidal activity,and structure-activity relationship(SAR):studies of novel triazone derivatives containing urea bridge group based on the transient receptor potential(TRP)channels[J].Mol Divers,2016,20(4):919-936.
[7]Zhou Q F,Du F Y,Shi Y J,et al.An efficient protocol for the production of pymetrozine via a new synthetic strategy[J].J Chem Res,2018,42:434-438.
[8]Nesterov A,Spalthoff C,Kandasamy R,et al.TRP channels in insect stretch receptors as insecticide targets[J].Neuron,2015,86(3):665-671.
[9]Kandasamy R,London D,Stam L,et al.Afidopyropen:new and potent modulator of insect transient receptor potential[J].Insect Biochem Mol,2017,84:32-39.
[10]Mao F,Guo L,Jin M,et al.Molecular cloning and characterization of TRPVs in two rice pests:nilaparvata lugens(St■l)and nephotettix cincticeps(Uhler)[J].Pest Manag Sci,2018,75(5):1 361-1 369.
[11]Wang L X,Niu C D,Salgadob V L,et al.Pymetrozine activates TRPV channels of brown planthopper nilaparvata lugens[J].Pestic Biochem Phys,2019,153:77-86.
[2]Ochomogo O R.Selective herbicide[P].US:4101308,1978-07-18.
[3]Wang B Z,Ke S Y,Kishore B B,et al.A facile synthesis of pyrimidone derivatives and single-crystal characterization of pymetrozine[J].Syn Commun,2012,42(16):2 327-2 336.
[4]Yang Y,Liu Y X,Song,H J,et al.Additive effects on the improvement of insecticidal activity:Design,synthesis,and insecticidal activity of novel pymetrozine derivatives[J].Bioorg Med Chem,2016,24(3):391-402.
[5]Yang Y,Huang Y Q,Song H J,et al.Skeletal modifications of β-carboline alkaloids and their antiviral activity study[J].Mol Divers,2016,20(4):829-835.
[6]Yang Y,Liu Y X,Song H J,et al.Design,synthesis,insecticidal activity,and structure-activity relationship(SAR):studies of novel triazone derivatives containing urea bridge group based on the transient receptor potential(TRP)channels[J].Mol Divers,2016,20(4):919-936.
[7]Zhou Q F,Du F Y,Shi Y J,et al.An efficient protocol for the production of pymetrozine via a new synthetic strategy[J].J Chem Res,2018,42:434-438.
[8]Nesterov A,Spalthoff C,Kandasamy R,et al.TRP channels in insect stretch receptors as insecticide targets[J].Neuron,2015,86(3):665-671.
[9]Kandasamy R,London D,Stam L,et al.Afidopyropen:new and potent modulator of insect transient receptor potential[J].Insect Biochem Mol,2017,84:32-39.
[10]Mao F,Guo L,Jin M,et al.Molecular cloning and characterization of TRPVs in two rice pests:nilaparvata lugens(St■l)and nephotettix cincticeps(Uhler)[J].Pest Manag Sci,2018,75(5):1 361-1 369.
[11]Wang L X,Niu C D,Salgadob V L,et al.Pymetrozine activates TRPV channels of brown planthopper nilaparvata lugens[J].Pestic Biochem Phys,2019,153:77-86.