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. 2021 Feb 20;46(1):120-123.
doi: 10.1584/jpestics.D20-076.

Isoxaben analogs inhibit chitin synthesis in the cultured integument of the rice stem borer Chilo suppressalis

Kotaro Mori  1 , Hideya Tokuoka  1 , Hisashi Miyagawa  1 , Yoshiaki Nakagawa  1
Affiliations

Isoxaben analogs inhibit chitin synthesis in the cultured integument of the rice stem borer Chilo suppressalis

Kotaro Mori et al. J Pestic Sci. .

Abstract

Benzoylphenylureas (BPUs) were discovered as novel type insecticides about a half century ago; many analogs have been launched as insecticides and acaricides. BPUs are known to inhibit chitin synthesis in insects and other arthropods, but they have no effect against microorganisms such as fungi. We designed new chitin synthesis inhibitors based on the hypothesis that biomolecules that play important roles in cellulose and chitin biosynthesis are similar. In the full automatic modeling system (FAMS), the cellulose synthase was selected as a template three-dimensional structure. Thus, we focused on the structure of cellulose synthase inhibitor, isoxaben, to develop new chemistry. The 1,1-diethylethyl [-C(CH3)(CH2CH3)2] group of isoxaben was changed to a 4-substituted phenyl group bearing Cl, Et, or Ph. These compounds significantly inhibited chitin synthesis in the cultured integument of the rice stem borer Chilo suppressalis. The activity of the 4-ethylphenyl analog was enhanced 30-fold by adding piperonyl butoxide to the culture medium.

Keywords: Chilo suppressalis; benzoylphenylurea; cellulose synthase; chitin synthase; chitin synthesis inhibitors; isoxazole.

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Figures

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Fig. 1. Chemical structures of launched insecticides and acaricides
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Fig. 2. Structures of isoxaben, LY131215 and newly synthesized IOXs
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Scheme 1.
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Fig. 3. Concentration-response curve for the inhibition of [14C]NAG incorporation to the cultured integument of compound 1
See this image and copyright information in PMC

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