Mori Kotaro, Tokuoka Hideya, Miyagawa Hisashi, Nakagawa Yoshiaki
Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan.
J Pestic Sci. 2021 Feb 20;46(1):120-123. doi: 10.1584/jpestics.D20-076.
Benzoylphenylureas (BPUs) were discovered as novel type insecticides about a half century ago; many analogs have been launched as insecticides and acaricides. BPUs are known to inhibit chitin synthesis in insects and other arthropods, but they have no effect against microorganisms such as fungi. We designed new chitin synthesis inhibitors based on the hypothesis that biomolecules that play important roles in cellulose and chitin biosynthesis are similar. In the full automatic modeling system (FAMS), the cellulose synthase was selected as a template three-dimensional structure. Thus, we focused on the structure of cellulose synthase inhibitor, isoxaben, to develop new chemistry. The 1,1-diethylethyl [-C(CH)(CHCH)] group of isoxaben was changed to a 4-substituted phenyl group bearing Cl, Et, or Ph. These compounds significantly inhibited chitin synthesis in the cultured integument of the rice stem borer . The activity of the 4-ethylphenyl analog was enhanced 30-fold by adding piperonyl butoxide to the culture medium.
苯甲酰基苯基脲（BPUs）大约在半个世纪前被发现是新型杀虫剂；许多类似物已作为杀虫剂和杀螨剂推出。已知BPUs能抑制昆虫和其他节肢动物的几丁质合成，但对真菌等微生物没有作用。我们基于纤维素和几丁质生物合成中起重要作用的生物分子相似这一假设设计了新的几丁质合成抑制剂。在全自动建模系统（FAMS）中，选择纤维素合酶作为模板三维结构。因此，我们专注于纤维素合酶抑制剂异恶草酮的结构，以开发新的化学物质。异恶草酮的1,1 - 二乙乙基[-C(CH)(CHCH)]基团被改为带有Cl、Et或Ph的4 - 取代苯基。这些化合物显著抑制了稻螟培养体壁中的几丁质合成。通过向培养基中添加胡椒基丁醚，4 - 乙基苯基类似物的活性提高了30倍。
