新型含(卤代)烷氧基类双酰胺化合物的合成、杀虫活性及构效关系研究
Synthesis,Insecticidal Activities,and Structure-Activity Relationship Studies of Novel Diamide Compounds Containing(Halogenated)Alkoxy Group
刘吉永 1吴明慧 2相君成 3庞怀林 2李斌 1吕亮2
作者信息
- 1. 沈阳农业大学植物保护学院 沈阳 110866
- 2. 南通泰禾化工股份有限公司 江苏南通 226407
- 3. 上海晓明检测技术服务有限公司 上海 200335
- 折叠
摘要
为了发现结构新颖、活性优异、环境友好的新型杀虫剂,以环丙氟虫胺为先导化合物,在其苯胺部分引入(卤代)烷氧基单元,设计合成了一系列未见文献报道的新型含(卤代)烷氧基类双酰胺化合物,其结构经过1HNMR、13C NMR和HRMS确证.初步的生物活性测试结果表明,大部分化合物对小菜蛾表现出优异的杀虫活性,其中N-[2-溴-4-(全氟丙烷-2-基)-6-(二氟甲氧基)苯基]-3-[N-(环丙甲基)苯甲酰胺基]-4-氟苯甲酰胺(4a)、N-[2-溴-4-(全氟丙烷-2-基)-6-(三氟甲氧基)苯基]-3-[N-(环丙甲基)苯甲酰胺基]-4-氟苯甲酰胺(4b)、N-(2-溴-6-(二氟甲氧基)-4-(全氟丙烷-2-基)苯基)-3-(N-(环丙基甲基)苯甲酰胺基)-2-氟苯甲酰胺(4h)、N-[2-溴-6-(二氟甲氧基)-4-(全氟丙烷-2-基)苯基]-3-[4-氰基-N-(环丙基甲基)苯甲酰胺]-2-氟苯甲酰胺(4j)～N-(3-((2-溴-6-(二氟甲氧基)-4-(全氟丙烷-2-基)苯基)氨基甲酰基)-2-氟苯基)-N-(环丙基甲基)异烟酰胺(4o)、N-(3-((2-溴-6-(二氟甲氧基)-4-(全氟丙烷-2-基)苯基)氨基甲酰基)-2-氟苯基)-N-(环丙基甲基)-2,4-二氟苯甲酰胺(4q)和N-(3-((2-溴-6-(二氟甲氧基)-4-(全氟丙烷-2-基)苯基)氨基甲酰基)-2-氟苯基)-N-(环丙基甲基)-2-氟异烟酰胺(4t)在1 mg/L浓度下显示出100％的杀虫活性.同时,化合物4a不仅对小菜蛾和二化螟的杀虫活性接近于环丙氟虫胺,而且对苜蓿蚜和朱砂叶螨的杀虫活性也较高,表现出比环丙氟虫胺更广的杀虫谱,其田间试验正在进行中.
Abstract
In order to discover new pesticide with novel structure,good activity and environmental friendliness,a series of new diamide compounds containing(halogenated)alkoxy group were designed and synthesized through introducing(halogen-ated)alkoxy group based on the structure of cyproflanilide.Their structures were confirmed by 1H NMR,13C NMR and HRMS.The bioassay results showed that most of the compounds exhibit excellent insecticidal activity against Plutella xy-lostella.Such as N-(2-bromo-6-(difluoromethoxy)-4-(perfluoropropan-2-yl)phenyl)-3-(N-(cyclopropylmethyl)-4-fluorobenz-amido)-2-fluorobenzamide(4a),N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethoxy)phenyl)-3-(N-(cyclopropylmethyl)-4-fluorobenzamido)-2-fluorobenzamide(4b),N-(2-bromo-6-(difluoromethoxy)-4-(perfluoropropan-2-yl)phenyl)-3-(N-(cyclo-propylmethyl)benzamido)-2-fluorobenzamide(4h),N-(2-bromo-6-(difluoromethoxy)-4-(perfluoropropan-2-yl)phenyl)-3-(4-cyano-N-(cyclopropylmethyl)benzamido)-2-fluorobenzamide(4j)～N-(3-((2-bromo-6-(difluoromethoxy)-4-(perfluoropropan-2-yl)phenyl)carbamoyl)-2-fluorophenyl)-N-(cyclopropylmethyl)isonicotinamide(4o),N-(3-((2-bromo-6-(difluoromethoxy)-4-(perfluoropropan-2-yl)phenyl)carbamoyl)-2-fluorophenyl)-N-(cyclopropylmethyl)-2,4-difluorobenzamide(4q)and N-(3-((2-bromo-6-(difluoromethoxy)-4-(perfluoropropan-2-yl)phenyl)carbamoyl)-2-fluorophenyl)-N-(cyclopropylmethyl)-2-fluoroiso-nicotinamide(4t)showed 100％mortality at 1 mg/L.Moreover,compound 4a not only has good insecticidal activities against Plutella xylostella and Chilo suppressalis close to cyproflanilide,but also shows better activities against Aphis craccivora and Tetranychus cinnabarinus than cyproflanilide,exhibiting a broader insecticidal spectrum.The field trials of compound 4a are ongoing.
关键词
双酰胺化合物/合成/杀虫活性/构效关系Key words
diamide compounds/synthesis/insecticidal activity/structure-activity relationship引用本文复制引用
出版年
2024
NETL
NSTL
万方数据