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Novel amino acid ester–chlorantraniliprole conjugates: design, synthesis, phloem accumulation and bioactivity
Author(s) -
Yao Guangkai,
Wen Yingjie,
Zhao Chen,
Xu Hanhong
Publication year - 2017
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.4592
Subject(s) - phloem , beet armyworm , xylem , spodoptera , in vivo , biochemistry , exigua , conjugate , amino acid , chemistry , hydrolysis , pesticide , ricinus , biology , botany , microbiology and biotechnology , agronomy , mathematical analysis , mathematics , gene , recombinant dna
Abstract BACKGROUND Conjugating amino acid and glucose fragments with existing pesticide structures has been shown to be an effective way to introduce phloem mobility into non‐phloem mobile species. However, the resulting derivatives always suffer from lower bioactivity compared with their parent compound. To solve this problem, we designed and synthesised a series of ester‐capped amino‐acid‐conjugated chlorantraniliproles. RESULTS The systemic test showed that all conjugates exhibited excellent phloem mobility and xylem mobility in a Ricinus communis model. In particular, compounds 7b, 8b and 8c were able to accumulate in phloem tissues in the form of their hydrolysis products, and the concentrations in phloem sap can reach 3 times the concentration in the incubation medium. Although their insecticidal activity ( LC 50 ) against the beet armyworm ( Spodoptera exigua ) in vitro was weaker than that of chlorantraniliprole, compounds 7b, 8b and 8c showed similar insecticidal activity in vivo against beet armyworm compared with the parent compound. CONCLUSIONS This work provides a potential strategy to obtain pesticide derivatives that possess both improved uptake and improved mobility in crops while retaining the in vivo insecticidal effect of the parent compound. © 2017 Society of Chemical Industry