Microbial hydroxylation of imidacloprid for the synthesis of highly insecticidal olefin imidacloprid
Microbial hydroxylation of imidacloprid for the synthesis of highly insecticidal olefin imidacloprid
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DOI：
10.1007/s00253-005-0223-3
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发表时间：
2006-08-01
影响因子：
5
通讯作者：
Ni, Jue-ping
中科院分区：
文献类型：
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作者：
Dai, Yi-jun;Yuan, Sheng;Ni, Jue-ping
对吡虫啉（IMI）有氧转化的微生物进行了分离和筛选，并研究了IMI的微生物区域和立体选择性羟基化作用。一些细菌和真菌将 IMI 转化为 5-羟基 IMI。嗜麦芽寡养单胞菌CGMCC 1.1788静息细胞以最高的转化率将IMI转化为R-5-羟基IMI。该酶催化咪唑烷环中 IMI C12 位的立体选择性羟基化。在酸性条件下，5-羟基IMI以高摩尔转化率转化为烯烃IMI。烯烃IMI对蚕豆蚜成虫和若虫的杀虫功效分别比IMI高约19和2.2倍，对褐飞虱成虫的活性比IMI高约1.4倍。一些碳水化合物和有机酸显着促进嗜麦芽糖链球菌CGMCC 1.1788静息细胞对IMI的转化率。与不含蔗糖的反应介质相比，含有5%蔗糖的反应介质的生物转化率提高了8.3倍。
Microorganisms that bring about the aerobic transformation of imidacloprid (IMI) were isolated and screened, and the microbial regio- and stereoselective hydroxylation of IMI was studied. Some bacteria and fungi transformed IMI to 5-hydroxyl IMI. Bacterium Stenotrophomonas maltophilia CGMCC 1.1788 resting cells transformed IMI into R-5-hydroxyl IMI at the highest conversion rate. The enzyme catalyzed the stereoselective hydroxylation at position C12 of IMI in the imidazolidine ring. Under acidic conditions, 5-hydroxyl IMI was converted into olefin IMI in high molar conversion yield. The olefin IMI exhibited about 19 and 2.2 times more insecticidal efficacy than IMI against horsebean aphid imago and nymph, respectively, and about 1.4 times more active than IMI against brown planthopper imago. The transformation rate of IMI by resting cells of S. maltophilia CGMCC 1.1788 was promoted significantly by some carbohydrates and organic acids. The reaction medium with 5% sucrose resulted in 8.3 times greater biotransformation yield as compared with that without sucrose.