Synthesis of Glucose–Fipronil Conjugate and Its Phloem Mobility

• Published in: Journal of agricultural and food chemistry Vol. 59; no. 23; pp. 12534 - 12542
• Main Authors: Yang, Wen, Wu, Han-Xiang, Xu, Han-Hong, Hu, An-Long, Lu, Meng-Ling
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 14.12.2011; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; Animals; Biological and medical sciences; castor beans; Chemistry; Chemistry, Applied; Crop and Animal Protection Chemistry; fipronil; Food industries; Food Science & Technology; Fundamental and applied biological sciences. Psychology; glucose; Glucose - chemistry; Glucosides - chemical synthesis; Glucosides - chemistry; insecticidal properties; insecticides; Insecticides - chemical synthesis; Insecticides - metabolism; Larva; Life Sciences & Biomedicine; mature plants; Molecular Structure; Moths; Phloem - metabolism; Physical Sciences; Pyrazoles - chemical synthesis; Pyrazoles - chemistry; Ricinus communis; Science & Technology; sieve tubes; Triazoles - chemical synthesis; Triazoles - chemistry; fipronil; click chemistry; glucose; phloem mobility; TRANSLOCATION; 2-NBDG; PLANT-CELLS; ACIDIC DERIVATIVES; RICINUS-COMMUNIS L; CARBOHYDRATE-CHEMISTRY; HEXOSE TRANSPORTER; XYLEM; FUNGICIDE FENPICLONIL; CARRIER-MEDIATED UPTAKE; Chemistry; Phloem; Synthesis; Mobility; Carbohydrate; Glucose
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf2031154

Phloem-mobile insecticides are preferred to achieve economically useful activity. However, only a few phloem-mobile synthetic insecticides are available. One approach to converting nonmobile insecticides into phloem-mobile types is introducing sugar to the parent compound. To test whether the addition of a glucose group to a non-phloem-mobile insecticide enables conversion into phloem-mobile, N-[3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazol-5-yl]-1-(β-d-glucopyranosyl)-1H-1,2,3-triazole-4-methanamine (GTF) was prepared through click chemistry. A phloem-mobility test in Ricinus communis L. seedlings confirmed that GTF was mobile in the sieve tubes. Although GTF exhibited lower insecticidal activity against the third-instar larvae of Pzlutella xylostella than fipronil did, it can be reconverted into fipronil in adult plants of castor bean, thereby offsetting the decrease of insecticidal activity. Therefore, the presence of a glucose core confers phloem mobility to fipronil.