AMINOCARB

Chemical properties

Tan; crystalline; slightly water-soluble; melting point 93–94C.

The Uses of AMINOCARB

Aminocarb is a carbamate insecticide.

The Uses of AMINOCARB

Insecticide.

The Uses of AMINOCARB

Nonsystemic, broad-spectrum insecticide used to control the spruce budworm in forests; molluscicide

Definition

ChEBI: A carbamate ester that is phenyl methylcarbamate substituted by a dimethylamino group at position 4 and a methyl group at position 3.

Hazard

Highly poisonous.

Environmental Fate

Plant/Surface Water. Several transformation products reported by Day (1991) include 4-amino-m-tolyl-N-methylcarbamate (AA), 4-amino-3-methylphenol (AC), 4-formamidom-tolyl-N-methylcarbamate (FA), N-(4-hydroxy-2-methylphenyl)-N-methylformamide (FC), 4-methylformamido-m-tolyl-N-methylcarbamate (MFA), 4-methylamino-m-tolyl-Nmethylcarbamate (MAA), 3-methyl-4-(methylamino)phenyl-N-methylcarbamate (MAC), phenol, methylamine and carbon dioxide. MAA was not detected in natural water but was detected in fish tissues following exposure to aminocarb-treated water in the laboratory. The metabolites FA, AC and MAC were detected in Canadian forests treated with aminocarb but the metabolites AA, MAA and FC were not detected (Day, 1991)
On and/or in bean plants, aminocarb degrades with the carbamate moiety remaining intact. Methylcarbamate derivatives identified include the 4-methylamino, 4-amino, 4- methylformamido and 4-formamido analogs (Abdel-Wahab et al., 1966)
Photolytic. When aminocarb in ethanol was irradiated by UV light, extensive degradation was observed. No degradation products were identified; however, two unidentified cholinesterase inhibitors were reported (Crosby et al., 1965).
Chemical/Physical. Aminocarb is hydrolyzed in purified water to 4-(dimethylamino)- 3-methylphenol which is then converted to 2-methyl-1,4-benzoquinone. This compound was then oxidized to form the following compounds: 6-(dimethylamino)-2-methyl-1,4- benzoquinone, 6-(methylamino)-2-methyl-1,4-benzoquinone, 5-(dimethylamino)-2- methyl-1,4-benzoquinone and 5-(methylamino)-2-methyl-1,4-benzoquinone (Leger and Mallet, 1988). When aminocarb was irradiated by a high pressure xenon-mercury lamp (λ = 253.7 nm) in aerated and degassed ethyl alcohol and cyclohexene solutions, 4- dimethylamino-3-methyl phenol formed as the major product. A duplicate run using an excitation wavelength of >300 nm yielded that same phenol as the major product. Sinceaminocarb absorbs radiation in the solar region (at λ >300 nm), this compound would be expected to undergo photochemical degradation in the environment (Addison et al., 1974)
Emits toxic fumes of nitrogen oxides when heated to decomposition (Sax and Lewis, 1987)

Metabolic pathway

Aminocarb in purified water is hydrolyzed to 4- (dimethylamino)-3-methylphenol which is in turn converted to 2-methyl-1,4-benzoquinone either by direct means or via 2-methyl-1,4-dihydroquinone. The benzoquinone reacts readily with methylamine and diethylamine present in solution to give four red chemicals. In addition, mono- and diepoxides of 2-methyl-1,4-benzoquinone are formed.