ALANYCARB

Uses

Alanycarb is a broad spectrum oxime carbamate insecticide with both contact and oral toxicity to a wide variety of insect pests, especially Lepidoptera, Coleoptera, Hemiptera and Thysanoptera, in/on grapes, pome fruits, tobacco and vegetables. Alanycarb can be applied as foliar, soil or seed treatments.

Uses

Alanycarb may be used as an analytical reference standard for the determination of the analyte in:

• Olive oil samples by fast liquid chromatography-electrospray time-of-flight mass spectrometry (LC-TOFMS).
• Vegetables and fruit juices by LC coupled to tandem mass spectrometry (MS/MS).

Uses

Alanycarb is a oxime carbamate inseciticide with acetylcholinesterase inhibitor activity.

Definition

ChEBI: Alanycarb is a carbamate ester and an ethyl ester. It has a role as a carbamate insecticide, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an agrochemical and a nematicide.

General Description

Alanycarb is classified under the oxime carbamate group of insecticides. Its mode of action involves the inhibition of cholinesterase enzyme.

Metabolic pathway

Alanycarb is a pro-insecticide which transforms either chemically or biologically into the active substance methomyl. Alanycarb metabolism in soil, plants and animals follows a common pathway that is consistent with methomyl. The primary metabolic pathway involves the initial cleavage of the N-S bond of alanycarb to yield methomyl and ethyl N-benzyl-β-alaninate. Methomyl is further metabolised to S-methyl-N-hydroxythioacetimidate and ultimately to acetonitrile, acetic acid and carbon dioxide (Scheme 1). See also the methomyl entry.

Degradation

Alanycarb (1) was stable to hydrolytic degradation in neutral and weakly basic solutions (pH 7 and 9) at 30 °C with DT₅₀ of 49 hours and 130 hours, respectively. It degraded rapidly (DT₅₀ 0.5 hours) in acidic solution (pH 5) at 20 °C (Yagi and Kawata, 1992). In acidic buffer solution (pH 4.0), the major hydrolytic degradation product was methomyl (2). The disulfide derivative (3) of alanycarb was observed as a minor product. In pH 7 and 9 solutions, hydrolysis of methomyl [S-methyl-N-hydroxythioacetimidate (4)] occurred and polar unknown products were found as major degradation products (Kawata, 1994).
Alanycarb degraded rapidly under xenon lamp irradiation (light intensity: 280-300 μEm^-2 s^-1) in distilled water with a DT₅₀ of 9.3 hours (Yagi and Kawata, 1993).