Microbial hydroxylation of imidacloprid for the synthesis of highly insecticidal olefin imidacloprid

• Published in: Applied microbiology and biotechnology Vol. 71; no. 6; pp. 927 - 934
• Main Authors: Dai, Yi-jun, Yuan, Sheng, Ge, Feng, Chen, Ting, Xu, Shang-cheng, Ni, Jue-ping
• Format: Journal Article
• Language: English
• Published: Berlin Berlin/Heidelberg : Springer-Verlag 01.08.2006; Springer; Springer Nature B.V
• Subjects: Aerobic microorganisms; Aphididae; Aphidoidea; Bacteria; Bacteria - metabolism; Biological and medical sciences; Biotechnology; Biotransformation; Carbohydrates; chemistry; Fundamental and applied biological sciences. Psychology; fungi; Fungi - metabolism; Hydrogen-Ion Concentration; Hydroxylation; imagos; Imidacloprid; Imidazoles; Imidazoles - chemistry; Imidazoles - metabolism; Insecticides; Insecticides - chemistry; Insecticides - metabolism; metabolism; Microbiology; Microorganisms; Molecular Structure; Neonicotinoids; Nilaparvata lugens; Nitro Compounds; olefin; Organic acids; organic acids and salts; Oxidation-Reduction; Stenotrophomonas maltophilia; Stereoisomerism; Stereoselectivity; Sucrose; Temperature; Insecticide; Microorganism; Hydroxylation; Pesticides
• ISSN: 0175-7598; 1432-0614
• DOI: 10.1007/s00253-005-0223-3

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.