Description
(S)-(+)-Methoprene is a widely-used insect growth regulator. It is remarkable for its lack of significant effects against a wide variety of mammals, although concerns remain for its effects on arthropod development. Methoprene acts as an activator of the juvenile hormone receptor, known as Methoprene-tolerant or Met (K
d = 12.3 nM). Met is a transcription factor that, upon activation with juvenile hormone or methoprene, regulates gene expression that inhibits metamorphosis.
Uses
Insecticide; insect growth regulator.
Production Methods
The production of S-methoprene involves a multi-step organic synthesis starting from optically active precursors. One established method begins with (+)-dihydromyrcene, which undergoes selective hydroalumination followed by oxidation to yield S-(–)-citronellol. This intermediate is further oxidised to S-(–)-citronellal, which reacts with allylmagnesium chloride to form a key alcohol. Subsequent steps include Smidt-Moiseev oxygenation, dehydration, and Grignard reactions to build the conjugated diene ester backbone. The final transformation involves Brown solvomercuration-reduction in methanol, yielding S-methoprene with high stereochemical purity and biological activity.
Definition
ChEBI: (S)-methoprene is a methoprene. It is an enantiomer of a (R)-methoprene.
Mechanism of action
A juvenile hormone mimic (terpene). Contact and stomach action, acts by mimicing the action of the juvenile hormone keeping the insect in an immature state
Side effects
S)-methoprene alone is well tolerated by dogs and cats, with a low toxicity and high safety margin. Side effects experienced by dogs and cats after treatment with products containing (S)-methoprene can generally be attributed to the other active or inert ingredients.
References
[1] SIDDALL J B. Insect growth regulators and insect control: a critical appraisal.[J]. Environmental Health Perspectives, 1976, 14: 119-126. DOI:
10.1289/ehp.7614119[2] WRIGHT J E. Environmental and toxicological aspects of insect growth regulators.[J]. Environmental Health Perspectives, 1976, 14: 127-132. DOI:
10.1289/ehp.7614127[3] JEAN-PHILIPPE CHARLES. Ligand-binding properties of a juvenile hormone receptor, Methoprene-tolerant.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2011: 21128-21133. DOI:
10.1073/pnas.1116123109[4] E. OSIR L R. Nuclear binding sites for juvenile hormone and its analogs in the epidermis of the tobacco hornworm.[J]. The Journal of Biological Chemistry, 1988, 23 1: 13812-13818. DOI:
10.1016/s0021-9258(18)68316-4[5] ZHEN ZOU. Juvenile hormone and its receptor, methoprene-tolerant, control the dynamics of mosquito gene expression.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2013: E2173-81. DOI:
10.1073/pnas.1305293110
Pesticide Type
Insecticide; Veterinary substance
