Benzpyrimoxan

Description

Benzpyrimoxan is a rice insecticide mainly used for the control of sap sucking insects especially those resistant to other chemicals. It has a low aqueous solubility and is not volatile. It has a low toxicity to birds and honeybees but is more toxic to fish. The mammalian oral toxicity is low but little else is known about its potential impact on human health.

Uses

Benzpyrimoxan (NNI-1501) is an insecticide that shows remarkable activity against nymphs of rice planthoppers[1].

Production Methods

Benzpyrimoxan is manufactured through a compact, heterocycle-building sequence typical of early pyrimidinone-based insecticides. Commercial producers began by assembling the substituted pyrimidinone core through condensation of an appropriate beta-dicarbonyl compound with a guanidine-type reagent, generating the bicyclic heterocycle that defines the molecule’s biological activity. In parallel, the required benzyl or phenoxyalkyl fragment is prepared using standard aromatic substitution chemistry. These two advanced intermediates were then joined through a controlled alkylation step that installed the benzyl substituent onto the heterocycle under conditions mild enough to avoid ring degradation.

Definition

ChEBI: Benzpyrimoxan is a member of the class of pyrimidines that is pyrimidine substituted by [4-(trifluoromethyl)phenyl]methoxy and 1,3-dioxan-2-yl groups at positions 4 and 5, respectively. It is an insecticide discovered and developed by Nihon Nohyaku, inhibits molting of nymphs of plant and leaf hoppers and reduces the pest population in paddy fields. It has a role as an insecticide, an insect growth regulator and an agrochemical. It is a member of (trifluoromethyl)benzenes, a member of pyrimidines, an aromatic ether and a member of dioxanes.

Mechanism of action

Insect growth regulator

References

[1] Eikoh Satoh, et al. Benzpyrimoxan: Design, synthesis, and biological activity of a novel insecticide. J Pestic Sci. 2021 Feb 20;46(1):109-114. DOI:10.1584/jpestics.D20-069

Pesticide Type

Insecticide