METHYL BENZIMIDAZOLYL CARBAMATE

The whole is slowly heated to 85°C and stirred at this temperature for 45 minutes. The reaction mixture is cooled and the precipitated product is filtered off. It is washed successively with water and ethanol, dried and crystallized from a mixture of acetic acid and methanol, yielding methyl N-[5(6)-benzoyl-2-benzimidazolyl] carbamate MP 288.5°C. 

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]. 

Chemical Name Methyl-N-[5(6)-p-fluorobenzoyl-2-benzimidazolyl]carbamate Common Name -Structural Formula ... 

A mixture of 89 parts of S-methylisothiourea sulfate, 6.05 parts of methyl chloroformate in 7 parts of water is cooled, and at a temperature of 5°C to 10°C, sodium hydroxide solution 25% is added until pH equals 8. Then there are added successively 6.4 parts of acetic acid, 2.6 parts of sodium acetate and 8.9 parts of 3,4-diamino-4 -fluorobenzophenone hydrochloride and the whole is stirred while heating at 85°C for 45 minutes (during this reaction time, water and 2-propanol is added). The precipitated product is filtered off, washed with methanol and recrystallized from a mixture of 200 parts of acetic acid and 80 parts of methanol, yielding methyl N-[5(6)-p-fluorobenzoyl-2-benzimidazolyl] carbamate MP > 260°C. 

N-2-(BENZIMIDAZOLYL) CARBAMATE IH-BENZIMIDAZOL-2-YLCARBAMIC ACID METHYL ESTER... 

CHEMICAL PROPERTIES stable under ordinary conditions of use and storage hazardous polymerization has not been reported dissociates in some solvents to form carben-dazim and butyl isocyanate decomposes in aqueous solution to methyl n-(benzimidazolyl) carbamate and the ethyl analog decomposes without melting above 300 C (572°F) decomposed by strong acids and strong alkalies FP (NA) LFL/UFL (NA) AT (NA) HC (NA). 

N-2-(Benzimidazolyl) carbamate. See Carbendazim 2-Benzimidazolylcarbamic acid. See Benzimidazole carbamate 1H-Benzimidazol-2-ylcarbamic acid methyl ester. See Carbendazim 4-(2-BenzimidazolyO thiazol. See Thiabendazole Benzin Benzine. See Naphtha Benzine (light petroleum distillate). See VM P naphtha Benzinoform. See Carbon tetrachloride Benzisothiazolinone. See 1,2-Benzisothiazolin-3-one... 

Synonyms BCM 2-Benzimidazolecarbamic acid, methyl ester IH-Ben-zimidazole-2-yl methyl carbamate N-2-(Benzimidazolyl) carbamate 1 H-Benzimidazol-2-ylcarbamic acid methyl ester BMC Carbendazol MBC 2-(Methoxycarbonylamino) benzimidazol 2-(Methoxycarbonyl-amino) benzimidazole Methyl 2-benzimidazolecarbamate Methyl ben-zimidazole-2-yl carbamate Methyl benzimidazol-2-yl carbamate 2-(Methyloxycarbonylamino) benzimidazole Empirical C,H,NA... 

The first synthesis of SFs-substituted benzimidazoles was described in an Asahi Glass patent (04JPP059452). Protected N-acetyl-4-SF5-aniline (58) was converted into the protected nitroaniHne 59, which was then quantitatively deprotected to nitroaniline 60, reduction of which provided 1,2-diamino-4-SF5-benzene 61 in 100% yield. Condensation of diamine 61 with formamide or A/,N-(bis)methoxycarbonyl-S-methylisothiourea (62) resulted in the formation of the corresponding S-SFs-benzimidazole 63 or S-SFs-substituted methyl (2-benzimidazolyl)carbamate 64 (Scheme 15). 

---