title: Biological and nonbiological modifications of carbamates.
abstract: Methylcarbamate insecticides undergo hydrolysis, oxidation, dealkylation, and conjugation in animals, plants, and insects to form similar or identical products. Carbaryl is hydroxylated in biological systems to form hydroxy, dihydro-dihydroxy, and N-hydroxymethyl carbaryl and is hydrolysed to form 1-naphthol. The products are conjugated, stored, or excreted. Carbofuran is hydroxylated at the 3 position and propoxur at the 5 position to form hydroxylated derivatives. N-hydroxymethyl derivatives of these two carbamates may also be formed. Hydrolysis appears to be the major metabolic pathway of carbofuran in the animal. Aldicarb is oxidized to its sulfoxide and then hydrolysed to the oxime sulfoxide in animals and plants. Plants hydrolyse the oxime sulfoxide to form the corresponding aldehyde, which is an intermediate in the formation of 2-methyl-2-(methyl-sulfinyl)propanol. Methomyl, which is structurally similar to aldicarb, is metabolized in plants to acetonitrile, carbon dioxide, and methylamine. Bux and Meobal undergo hydrolysis and hydroxylation to form N-hydroxy methylcarbamates, as well as hydroxybutylphenyl and hydroxymethylphenyl methylcarbamates. Zectran, which contains a dimethylamino group, is converted to the methylamino, amino, and methylformamido derivatives by insects and plants. In soil and water, methylcarbamate insecticides are hydrolysed to their respective phenols or oximes.
mesh_terms: D000433:1-Propanol / Q000378:metabolism; D000818:Animals; D001572:Benzofurans / Q000378:metabolism; D002219:Carbamates / Q000378:metabolism*; D012721:Carbaryl / Q000378:metabolism; D002247:Carbon Isotopes; D002417:Cattle; D055598:Chemical Phenomena; D002621:Chemistry; D004285:Dogs; D006868:Hydrolysis; D007097:Imines / Q000378:metabolism; D007313:Insecta / Q000378:metabolism; D007306:Insecticides / Q000378:metabolism*; D008744:Methylamines / Q000378:metabolism; D008862:Microsomes, Liver / Q000378:metabolism; D010084:Oxidation-Reduction; D010091:Oximes / Q000378:metabolism; D010944:Plants / Q000378:metabolism; D051381:Rats; D013440:Sulfides / Q000378:metabolism; D014992:Xylenes / Q000378:metabolism
chemical_list: D001572:Benzofurans; D002219:Carbamates; D002247:Carbon Isotopes; D007097:Imines; D007306:Insecticides; D008744:Methylamines; D010091:Oximes; D013440:Sulfides; D014992:Xylenes; D000433:1-Propanol; D012721:Carbaryl