Synthesis of glucose-fipronil conjugate and its phloem mobility.
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.
Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education, South China Agricultural University, Guangzhou, Guangdong 510642, China.
Wen
W
Yang
Han-Xiang
HX
Wu
Han-Hong
HH
Xu
An-Long
AL
Hu
Meng-Ling
ML
Lu
D000818:Animals; D002367:Ricinus communis; D005947:Glucose / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D007306:Insecticides / Q000138:chemical synthesis* / Q000378:metabolism*; D007814:Larva; D015394:Molecular Structure; D009036:Moths; D052585:Phloem / Q000378:metabolism*; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D005960:Glucosides; D007306:Insecticides; C570608:N-(3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazol-5-yl)-1-(beta-D-glucopyranosyl)-1H-1,2,3-triazole-4-methanamine; D011720:Pyrazoles; D014230:Triazoles; D005947:Glucose; C082360:fipronil