含硝基缩氨基胍活性结构的甲氧基丙烯酸酯类化合物的合成、生物活性与构效关系研究
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摘要
甲氧基丙烯酸酯类杀菌剂具备低毒、高效、广谱、内吸性等多种优点,但由于其作用位点单一,短时间内被大量使用,抗性问题日益突出。因此,设计合成多作用位点、结构新颖的甲氧基丙烯酸酯类杀菌剂成为当前的研究重点。
本实验室前期通过撷取新烟碱类和缩氨基脲类杀虫剂的活性结构片段,发现了一个全新的高活性硝基缩氨基胍结构单元。将其与甲氧基丙烯酸酯类农药的主要中间体(E)-2-(2-溴甲基)苯基-2-甲氧亚胺基乙酸甲酯和(E)-2-(2-溴甲基)苯基-3-甲氧基丙烯酸甲酯进行拼接,共合成含甲氧基丙烯酸甲酯和硝基缩氨基胍结构单元的目标化合物70个(如下图所示),分离出3类主要副产物,并对其形成机理进行了探讨；初步摸索了目标化合物在醋酸条件下的进一步关环反应,得到硝基亚氨基1,2,4-三唑啉类产物1个。所有化合物均经核磁共振氢谱、红外光谱、高分辨质谱等予以表征。
分别以桃蚜、桃粉大尾蚜、大豆蚜为测试对象。采用浸渍法对桃蚜的杀虫活性测定结果显示,多数化合物的LC5o值小于30μg/mL,其中化合物ZNQ-1420、ZNQ-1426和ZNQ-1448的LC5o值分别是0.53、0.32和0.19μg/mL。采用喷雾法对桃粉大尾蚜的杀虫活性测定结果显示,多数化合物LC5o值小于50μg/mL,其中ZNQ-1404、ZNQ-1407和ZNQ-1443的LC5o值分别为3.00、1.40和2.02μg/mL。采用药膜法对部分化合物在200μg/mL下对大豆蚜进行初筛,发现化合物ZNQ-1455、ZNQ-1456、ZNQ-1462、ZNQ-1463、ZNQ-1464、ZNQ-1466等多个化合物致死率在70%以上,其中ZNQ-1463的致死率达到92%。
分别以棉花立枯、番茄晚疫、辣椒疫霉、苹果轮纹、西瓜炭疽、瓜果腐霉和黄瓜灰霉七种病原菌为测试对象,药剂浓度为50μg/mL下初筛数据显示,整体上对黄瓜灰霉病的防效最好,对苹果轮纹病防效较好,对番茄晚疫、棉花立枯和瓜果腐霉病防效一般,对辣椒疫霉和西瓜炭疽病防效较差。其中ZNQ-1459对黄瓜灰霉病菌的抑制率达到77.4%,ZNQ-1401和ZNQ-1405对苹果轮纹病菌的抑制率分别为74.3%和70.7%,ZNQ-1411和ZNQ-1426对番茄晚疫病菌的抑制率均为60.1%,ZNQ-1454对棉花立枯病菌的抑制率为41.7%,均优于或接近对照药剂嘧菌酯的抑菌效果。此外,发现副产物ZNQ-1432-B1对以上七种病原菌的抑制率均高于或接近嘧菌酯。不仅如此,该化合物在200μg/mL下对大豆蚜的致死率达到62%,有明显的杀虫活性。
部分化合物活体和离体孢子萌发抑制测定结果表明,化合物ZNQ-1422、ZNQ-1427、ZNQ-1428和ZNQ-1443在100μg/mL下对黄瓜炭疽病原菌的抑制率达到100%；同时,在6.25μg/mL下,化合物ZNQ-1427对稻瘟病原菌和蔬菜灰霉原菌具有100%的抑制孢子萌发效果,上述化合物均具有进一步研究的价值。
利用Gaussian09对目标化合物的8种可能构型和构象进行了结构优化,并确立了最稳定构型和构象,进一步通过分子叠合、CoMFA和CoMSIA模型建立等完成了对化合物的构效关系研究,包括对桃蚜和桃粉大尾蚜杀虫活性的CoMSIA研究以及对苹果轮纹病菌的杀菌活性CoMFA研究。通过研究化合物在立体场、静电场、疏水场、供体和受体场下对活性的影响程度,进一步解释了构效关系,并为设计更高活性化合物奠定了一定的基础。
Strobilurin fungicides possess several advantages such as low toxicity, high efficiency,broad-spectr-um, systemic, but its single-action site and prominent resistance problems after frequently used in field-s limit its widespread application. Thus, it is essential to explore novel strobilurin fungicides with multi-sites of action and new structure.
On the basis of the preliminary work, we found hydrocarbylidene hydrazinecarboximidamide was a highly active unit extracted from neonicotinoids and hydrocarbylidene hydrazinecarboxamides belong to two different typical insecticides,. We combined it with key intermediates (E)-2-(2-bromomethyl) phenyl-2-methoxyimino acetate and (E)-2-(2-bromomethyl) phenyl-3-methoxypropenoate of stro-bilurin fungicides, and synthesized seventy novel strobilurins containing hydrocarbylidene hydrazinec-arboximidamide (see figure below), isolated three kinds of byproducts at the same time and discussed its formation mechanism. We initially explored the cyclization reaction conditions of target compound under acetic acid and obtained one3-nitroimine-1,2,4-triazoline derivatives. All compounds were char-acterized by1H NMR, IR and HRMS.
The activities of the target compounds against Myzus persicae Sulzer, Hyalopterus amygdali Blanchard and Aphis glycines Matsmura were screened by the method of immersion, spraying and dry film. As shown by the insecticidal activity data against Myzus persicae Sulzer, the LC50value of most compounds were less than30ug/mL, especially compound ZNQ-1420,ZNQ-1426and ZNQ-1448,the LC50value were0.53,0.32and0.19μg/mL, respectively; the activity against Hyalopterus amygdali Blanchard showed that the LC50value of most compounds were less than50ug/mL; in particular ZNQ-1404, ZNQ-1407and ZNQ-1443with a LC50value3.00,1.40and2.02μg/mL, respectively; the initial insecticidal activity against Aphis glycines Matsmura indicated that the lethal rate of ZNQ-1455, ZNQ-1456, ZNQ-1462, ZNQ-1463, ZNQ-1464and ZNQ-1466were exceeded70%at the concentration of200ug/mL, compound ZNQ-1463even reached92%.
Preliminary bioassay of part compouds was completed against Rhizoctonia solani, Phytophthora infestans, phytophthora capsici, Physalospora piricoia, Colletotrichum lagenarium, Pythium aphanide-rmatum and Botrytis cinerea. Overall these compounds displayed good fungicidal activity against Bot-rytis cinerea, better than Physalospora piricola, Rhizoctonia solani and Pythium aphanidermatum, but bad effective to phytophthora capsici and Colletotrichum lagenarium. Among them, compound ZNQ-14 59has good fungicidal activity against Botrytis cinerea with an inhibition rate of77.4%. The inhibition rate of ZNQ-1401and ZNQ-1405against Physalospora piricola were74.3%and70.7%, respectively, The inhibition rate of ZNQ-1411and ZNQ-1426was60.1%against Phytophthora infestan-s.ZNQ-1454have good fungicidal activity against Rhizoctonia solani with an inhibition rate of41.7%. They all showed better or comprable activity than Azoxystrobin. It is also worth to mention that the activity of the by-product ZNQ-1432-B1was higher than or close to azoxystrobin against seven fungi. Moreover, it also exhibited good insecticidal activity. At the concentration of200ug/mL, its lethal rate reached62%against Aphis glycines Matsmura.
The results of some target compounds against pathogens in vivo and spore germination in vitro indicated that compounds ZNQ-1422, ZNQ-1427, ZNQ-1428and ZNQ-1443completely inhibit colletotrichum lagenarium at the concentration of100ug/mL, and the inhibition rate of ZNQ-1427reached100%against Pyricularia oryzae and Botrytis cinerea on in vitro spore germination at the concentration of6.25ug/mL, so further researchs on these compounds are necessary.
Eight possible configurations and conformations of target compounds were optimized by using the Gaussian09and confirmed the most stable conformation. The structure-activity relationship was studied by further molecular alignment and establishing CoMFA and CoMSIA model, including3D-QSAR studies on the insecticidal activity against Myzus persicae Sulzer and Hyalopterus amygdali Blanchard and the fungicidal activities against Physalospora piricola. The effect of steric field, electrostatic field, hydrophobic field, donor field and acceptor field on the activity of these compounds explained the structure-activity relationships and laid a foundation for the design of more active compounds.
本实验室前期通过撷取新烟碱类和缩氨基脲类杀虫剂的活性结构片段,发现了一个全新的高活性硝基缩氨基胍结构单元。将其与甲氧基丙烯酸酯类农药的主要中间体(E)-2-(2-溴甲基)苯基-2-甲氧亚胺基乙酸甲酯和(E)-2-(2-溴甲基)苯基-3-甲氧基丙烯酸甲酯进行拼接,共合成含甲氧基丙烯酸甲酯和硝基缩氨基胍结构单元的目标化合物70个(如下图所示),分离出3类主要副产物,并对其形成机理进行了探讨；初步摸索了目标化合物在醋酸条件下的进一步关环反应,得到硝基亚氨基1,2,4-三唑啉类产物1个。所有化合物均经核磁共振氢谱、红外光谱、高分辨质谱等予以表征。
分别以桃蚜、桃粉大尾蚜、大豆蚜为测试对象。采用浸渍法对桃蚜的杀虫活性测定结果显示,多数化合物的LC5o值小于30μg/mL,其中化合物ZNQ-1420、ZNQ-1426和ZNQ-1448的LC5o值分别是0.53、0.32和0.19μg/mL。采用喷雾法对桃粉大尾蚜的杀虫活性测定结果显示,多数化合物LC5o值小于50μg/mL,其中ZNQ-1404、ZNQ-1407和ZNQ-1443的LC5o值分别为3.00、1.40和2.02μg/mL。采用药膜法对部分化合物在200μg/mL下对大豆蚜进行初筛,发现化合物ZNQ-1455、ZNQ-1456、ZNQ-1462、ZNQ-1463、ZNQ-1464、ZNQ-1466等多个化合物致死率在70%以上,其中ZNQ-1463的致死率达到92%。
分别以棉花立枯、番茄晚疫、辣椒疫霉、苹果轮纹、西瓜炭疽、瓜果腐霉和黄瓜灰霉七种病原菌为测试对象,药剂浓度为50μg/mL下初筛数据显示,整体上对黄瓜灰霉病的防效最好,对苹果轮纹病防效较好,对番茄晚疫、棉花立枯和瓜果腐霉病防效一般,对辣椒疫霉和西瓜炭疽病防效较差。其中ZNQ-1459对黄瓜灰霉病菌的抑制率达到77.4%,ZNQ-1401和ZNQ-1405对苹果轮纹病菌的抑制率分别为74.3%和70.7%,ZNQ-1411和ZNQ-1426对番茄晚疫病菌的抑制率均为60.1%,ZNQ-1454对棉花立枯病菌的抑制率为41.7%,均优于或接近对照药剂嘧菌酯的抑菌效果。此外,发现副产物ZNQ-1432-B1对以上七种病原菌的抑制率均高于或接近嘧菌酯。不仅如此,该化合物在200μg/mL下对大豆蚜的致死率达到62%,有明显的杀虫活性。
部分化合物活体和离体孢子萌发抑制测定结果表明,化合物ZNQ-1422、ZNQ-1427、ZNQ-1428和ZNQ-1443在100μg/mL下对黄瓜炭疽病原菌的抑制率达到100%；同时,在6.25μg/mL下,化合物ZNQ-1427对稻瘟病原菌和蔬菜灰霉原菌具有100%的抑制孢子萌发效果,上述化合物均具有进一步研究的价值。
利用Gaussian09对目标化合物的8种可能构型和构象进行了结构优化,并确立了最稳定构型和构象,进一步通过分子叠合、CoMFA和CoMSIA模型建立等完成了对化合物的构效关系研究,包括对桃蚜和桃粉大尾蚜杀虫活性的CoMSIA研究以及对苹果轮纹病菌的杀菌活性CoMFA研究。通过研究化合物在立体场、静电场、疏水场、供体和受体场下对活性的影响程度,进一步解释了构效关系,并为设计更高活性化合物奠定了一定的基础。
Strobilurin fungicides possess several advantages such as low toxicity, high efficiency,broad-spectr-um, systemic, but its single-action site and prominent resistance problems after frequently used in field-s limit its widespread application. Thus, it is essential to explore novel strobilurin fungicides with multi-sites of action and new structure.
On the basis of the preliminary work, we found hydrocarbylidene hydrazinecarboximidamide was a highly active unit extracted from neonicotinoids and hydrocarbylidene hydrazinecarboxamides belong to two different typical insecticides,. We combined it with key intermediates (E)-2-(2-bromomethyl) phenyl-2-methoxyimino acetate and (E)-2-(2-bromomethyl) phenyl-3-methoxypropenoate of stro-bilurin fungicides, and synthesized seventy novel strobilurins containing hydrocarbylidene hydrazinec-arboximidamide (see figure below), isolated three kinds of byproducts at the same time and discussed its formation mechanism. We initially explored the cyclization reaction conditions of target compound under acetic acid and obtained one3-nitroimine-1,2,4-triazoline derivatives. All compounds were char-acterized by1H NMR, IR and HRMS.
The activities of the target compounds against Myzus persicae Sulzer, Hyalopterus amygdali Blanchard and Aphis glycines Matsmura were screened by the method of immersion, spraying and dry film. As shown by the insecticidal activity data against Myzus persicae Sulzer, the LC50value of most compounds were less than30ug/mL, especially compound ZNQ-1420,ZNQ-1426and ZNQ-1448,the LC50value were0.53,0.32and0.19μg/mL, respectively; the activity against Hyalopterus amygdali Blanchard showed that the LC50value of most compounds were less than50ug/mL; in particular ZNQ-1404, ZNQ-1407and ZNQ-1443with a LC50value3.00,1.40and2.02μg/mL, respectively; the initial insecticidal activity against Aphis glycines Matsmura indicated that the lethal rate of ZNQ-1455, ZNQ-1456, ZNQ-1462, ZNQ-1463, ZNQ-1464and ZNQ-1466were exceeded70%at the concentration of200ug/mL, compound ZNQ-1463even reached92%.
Preliminary bioassay of part compouds was completed against Rhizoctonia solani, Phytophthora infestans, phytophthora capsici, Physalospora piricoia, Colletotrichum lagenarium, Pythium aphanide-rmatum and Botrytis cinerea. Overall these compounds displayed good fungicidal activity against Bot-rytis cinerea, better than Physalospora piricola, Rhizoctonia solani and Pythium aphanidermatum, but bad effective to phytophthora capsici and Colletotrichum lagenarium. Among them, compound ZNQ-14 59has good fungicidal activity against Botrytis cinerea with an inhibition rate of77.4%. The inhibition rate of ZNQ-1401and ZNQ-1405against Physalospora piricola were74.3%and70.7%, respectively, The inhibition rate of ZNQ-1411and ZNQ-1426was60.1%against Phytophthora infestan-s.ZNQ-1454have good fungicidal activity against Rhizoctonia solani with an inhibition rate of41.7%. They all showed better or comprable activity than Azoxystrobin. It is also worth to mention that the activity of the by-product ZNQ-1432-B1was higher than or close to azoxystrobin against seven fungi. Moreover, it also exhibited good insecticidal activity. At the concentration of200ug/mL, its lethal rate reached62%against Aphis glycines Matsmura.
The results of some target compounds against pathogens in vivo and spore germination in vitro indicated that compounds ZNQ-1422, ZNQ-1427, ZNQ-1428and ZNQ-1443completely inhibit colletotrichum lagenarium at the concentration of100ug/mL, and the inhibition rate of ZNQ-1427reached100%against Pyricularia oryzae and Botrytis cinerea on in vitro spore germination at the concentration of6.25ug/mL, so further researchs on these compounds are necessary.
Eight possible configurations and conformations of target compounds were optimized by using the Gaussian09and confirmed the most stable conformation. The structure-activity relationship was studied by further molecular alignment and establishing CoMFA and CoMSIA model, including3D-QSAR studies on the insecticidal activity against Myzus persicae Sulzer and Hyalopterus amygdali Blanchard and the fungicidal activities against Physalospora piricola. The effect of steric field, electrostatic field, hydrophobic field, donor field and acceptor field on the activity of these compounds explained the structure-activity relationships and laid a foundation for the design of more active compounds.
引文
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