Corteva Agriscience™, Agricultural Division of DowDuPont, Indianapolis, IN, USA.
Pest Manag Sci. 2019 Nov;75(11):3015-3023. doi: 10.1002/ps.5416. Epub 2019 Apr 22.
A chemical scaffold-hopping approach from known 3-hydroxyl-3-methylglutaryl-CoA (HMG-CoA) reductase inhibitors identified (E/Z)-2-arylstilbenes as novel insecticidal hits against two lepidopteran species, Spodoptera exigua and Trichoplusia ni. A structure-activity relationship (SAR) study of the aryl substituents and the E/Z conformations was carried out in an effort to improve insecticidal potency.
A series of (E/Z)-2-arylstilbenes was prepared and separated to evaluate their insecticidal potency against lepidopterous species in diet-feeding assays. The results showed that the (Z)-2-arylstilbenes were more active than their corresponding (E)-isomers, and a stereoselective synthesis was utilized to expand the SAR of the (Z)-2-arylstilbenes. (Z)-4'-Fluoro-3'-methyl-2-(2,4-difluorostyryl)-4-fluoro-5-methoxy-1,1'-biphenyl was the most potent analog in this study with strong activity against S. exigua, T. ni, Helicoverpa zea, Plutella xylostella and Pseudoplusia includens.
The (Z)-2-arylstilbenes were found to have strong insecticidal potency against five lepidopteran species. Ultimately, synthetic efforts could not improve insecticidal potency to commercial levels, and a lack of UV stability led to efforts being discontinued. © 2019 Society of Chemical Industry.
从已知的 3-羟基-3-甲基戊二酰辅酶 A（HMG-CoA）还原酶抑制剂中采用化学结构跳跃法，发现（E/Z）-2-芳基二苯乙烯类化合物是两种鳞翅目昆虫，甜菜夜蛾和烟青虫的新型杀虫剂。对芳基取代基和 E/Z 构象进行了构效关系（SAR）研究，以努力提高杀虫效力。
制备并分离了一系列（E/Z）-2-芳基二苯乙烯类化合物，以评估其在饮食喂养试验中对鳞翅目物种的杀虫活性。结果表明，（Z）-2-芳基二苯乙烯类化合物比其相应的（E）-异构体更具活性，并且利用立体选择性合成来扩展（Z）-2-芳基二苯乙烯类化合物的 SAR。在这项研究中，（Z）-4'-氟-3'-甲基-2-（2,4-二氟苯乙烯基）-4-氟-5-甲氧基-1,1'-联苯是最有效的类似物，对甜菜夜蛾、烟青虫、棉铃虫、小菜蛾和粘虫具有强烈的活性。
（Z）-2-芳基二苯乙烯类化合物对五种鳞翅目昆虫具有强烈的杀虫活性。最终，合成工作无法提高杀虫效力达到商业水平，并且缺乏 UV 稳定性导致停止了努力。© 2019 化学工业协会。
