Carbamates benomyl

Examples of synthetically produced and biologically active benzimidazoles are the fungicides methyl l-butylcarbamoyl-2-benzimidazole carbamate (benomyl) 5 and 2-(4 -thiazolyl)benzimidazole (thiabendazole) 6. The latter is used extensively as a preservative for fruit (E 233) and as an anthelmintic in veterinary medicine ... 

Barnes, T. B., Verlangieri, A. J., and Wilson, M. C. (1983). Reproductive toxicity of methyl-1-(butylcarbamoyl)-2-benrimidazole carbamate (benomyl) in male Wiscar rats. Toxicology 28,103-115. 

B1 1 -Tubuline assembly in mitosis Methyl- benzimidazole carbamates Benomyl, carbendazim, thiophanat- methyl Broad spectrum fungicides high resistance risk... 

Carbamate hydrolysis is frequendy observed as the initial reaction for pesticides having carbamate bonds, such as aldicarb, carbofuran, carbaryl, and benomyl (eq. 12) (19). Numerous genera of carbamate-hydroly2ing bacteria have been identified, including Pseudomonas, Jhihrobacter, Bacillus, Nocardia, Achromobacter, Flavobacterium, Streptomyces, Alcaligenes, A spirillum, Micrococcus, and Bhodococcus. 

Benomyl is used for its protective and eradicant activity against several pathogens of cereals, vines, fruit, rice and vegetables, and is used in postharvest treatments. Like thiophanate-methyl, it undergoes conversion in plants, soils and animals into the methylbenzimidazol-2-yl carbamate, carbendazim, which has a similar spectrum of activity. 

Additional methods considered for 304(h) rule making and the parameters measured are the following (the numbers in parentheses indicate the number of compounds included in the method) 622, organophosphorus pesticides (19) 623, 4,4 -methylene bis(2-chloroaniline) 626, acrolein and acrylonitrile (2) 627, dinitroaniline pesticides (5) 628, carbofuran 629, cyanazine 630, dithiocarbamates (15) 631, carbendazim and benomyl 632, carbamate and urea pesticides (7) and 633, organonitrogen pesticides (7). Most of these are... 

Most of the older methods of fluorimetric analysis of pesticides involved hydrolysis to form fluorescent anions. Co-ral (coumaphos) [147] was hydrolyzed in alkali to the hydroxybenzopyran, which was subsequently determined by means of its fluorescence. Guthion (azinphosmethyl) was hydrolyzed to anthranilic acid for fluorimetric analysis [148,149]. A method was developed [150] for Maretin (N-hydroxynaphthalimide diethyl phosphate) in fat and meat which involved hydrolysis in 0.5 M methanolic sodium hydroxide followed by determination of the fluorescence of the liberated naphthalimide moiety. Carbaryl (1-naphthyl N-methylcarbamate) and its metabolites have been determined by a number of workers using base hydrolysis and the fluorescence of the resulting naphtholate anion [151-153]. Nanogram quantities of the naphtholate anion could be detected. Zectran (4-dimethylamino-3,5-xylyl N-methylcarbamate) has been determined by the fluorescence of its hydrolysis product [154]. The fluorescence behaviour of other carbamate insecticides in neutral and basic media has been reported [155]. Gibberellin spray used on cherries has been determined fluorimetrically after treatment with strong acid [156]. Benomyl (methyl N-[l-(butylcarbamoyl)-2-benzimidazolyl]carbamate) has been analyzed by fluorimetry after hydrolysis to 2-aminobenzimidazole [157]. 

Carbamates (carbaryl, benomyl, carbofuran, aldicarb, methomyl). Symptoms of exposure were nausea, dizziness, b listers, dermatitis, malaise, sweating, tearing, breathing difficulty, and chest tightness. Usually, incidents have occurred within 1 to 2 days after application except for aldicarb (up to 4 days after application). 

Benomyl methyl 1-(butylcarbamoyl)-2-benzimidazole-carbamate Benlate Tersan 1991... 

Figure 5.10 Fungicides. Benlate contains the carbamate fungicide benomyl. Kocide 101 contains copper hydroxide, which is an inorganic copper containing fungicide.

Benomyl is a synthetic, organic fungistat having little or no acute toxic effect in mammals. No systemic poisonings have been reported in humans. Although the molecule contains a carbamate grouping, benomyl is not a cholinesterase inhibitor. It is poorly absorbed across skin that which is absorbed is promptly metabolized and excreted. 

Pesticide residues Acetochlor Alachlor Atrazine Carbendazin/Benomyl Cyclodienes, 2,4-D DDE Diuron Glyphosate Metolachlor Organophosphate/Carbamate Pyrethroids Spynosyn Surfactants Alkyl ethoxylate (AE) Alkylphenol ethoxylate (APE) Linear alkylbenzene sulfonate (LAS) Estrogens 17-B-Estradiol (E2) ... 

A few pro benzimidazoles such as benomyl (12), thiophanate (25), febantel (26) and netobimin (27) have also been developed, which exhibit anthelmintic activity by virtue of their ability to release the corresponding benzimidazoles as active metabolites in the biophase. Of these, benomyl undergoes hydrolysis to form carbendazim (10), while thiophanate, febantel and netobimin (25-27) cyclise in the hcsFs body to afford benzimidazole-2-carbamates (28) [11,15]. 

Benomyl is practically insoluble in water. It hydrolyses rapidly in aqueous media into methyl-N-benzimidazol-2-yl-carbamate (MBC) (Clemons and Sisler, 1969 Sims ei ai, 1969 Fuchs et ai, 1972, 1974). In the alkalyne hydrolysis of benomyl,... 

The main metabolite of benomyl is methyl N-(5-hydroxybenzimidazol-2-yl)-carbamate (43) (Watkins, 1976), which nas been detected in the urine conjugated with glucuronic acid or sulfate. Two-year chronic feeding tests similarly proved that there is no accumulation in warm-blooded animals. Residues in milk and eggs can be detected only at a feeding level of 25-50 mg/kg of benomyl (Gardiner et al.,... 

H-Benzimidazole-2-carbamic acid, 1-(butylcarbamomyl)-, methyl ester Benomyl 0-NH-C4H9 928a, 1219b, 1219c, 3585b, 3633, 3661a ... 

Benzimidazole-2-carbamic acid, 1-(butylcarbamomyl)-, methyl ester Benomyl ... 

Newsome, W, H, and Shields, J. B. (1981). A radioimmunoassay for benomyl and methyl 2-benzimidazole carbamate on food crops. J. Agric. Food Chem. 27, 220-222. 

W.H. Newsome, J.B. Shields, A Radioimmunoassay for Benomyl and Methyl 2-Benzimidazol Carbamate in Food Crops , /. Agric. Food Chem., 29, 220-222 (1981). 

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