4 -Chloroformanilide

Biological. In an anaerobic medium, the bacteria of the Paracoccus sp. converted 4-chloroaniline to l,3-bis(/t-chlorophenyl)triazene and 4-chloroacetanilide with product yields of 80 and 5%, respectively (Minard et al., 1977). In a field experiment, [ C]4-chloroaniline was applied to a soil at a depth of 10 cm. After 20 wk, 32.4% of the applied amount was recovered in soil. Metabolites identified include 4-chloroformanilide, 4-chloroacetanilide, 4-chloronitrobenzene, 4-chloronitrosobenzene, 4,4 -dichloroazoxybenzene, and 4,4 -dichloroazobenzene (Freitag et al, 1984). 

Chloroformanilide, see 4-Chloroaniline, Monuron p -Chloro-o-formotoluidide, see Chlordimeform 4-Chloro-2-formylphenol, see MCPA Chlorohydrin, see 2-Chloroethyl vinyl ether Chlorohydroquinone, see Chlorobenzene, 2-... 

Diflubenzuron can be either hydrolyzed at the urea bridge or oxidized by ring hydrox-ylation followed by conjugation. Hydrolytic cleavage seems to be a major route for diflubenzuron metabolism in many insect species. Two-spotted spider mites showed <10% absorption in 96 h of topically applied diflubenzuron. Of the amount absorbed, about 27% was metabolized in 96 h to 4-chlorophenyl urea, 2,6-difluorobenzoic acid, 4-chloroformanilide, 2,6-difluorobenzamide, and other metabolites. Effects of diflubenzuron were synergized by profenofos in cotton leafworm fourth instar larvae, and they were antagonized by 20-hydroxyecdysone in beetle (Tenebrio molitor) pupae. More information is needed on interaction effects of diflubenzuron with other chemicals. 

N-Ethyl-p-chloroformanilide, 1207 Ethyl chloroformate (Cathyl cUoride Ethyl chlorocarbonate), 86,239,364-367,370 Ethyl o-chlorophenylacetate, 1160 Ethyl oi-chloropropionate, 1160 Ethyl 2 hloropurme-6-carboxylate, 285 Ethyl cinnamate, 1066,1243 dibromide, 1078 Ethyl crotonate, 137, 787-788 Ethyl cyanate, 177... 

B. N-Ethyl-p-chloroaniline. In a 500-ml. round-bottomed flask are placed 70 g. (0.38 mole) of N-ethyl-/>-chloroformanilide and 170 ml. of 10% hydrochloric acid. The mixture is heated under reflux for 1 hour, cooled, then neutralized, and finally made basic with 15% potassium hydroxide solution. The lower layer of N-ethyl- -chloroaniline is separated, and the aqueous layer is saturated with potassium carbonate and extracted with two 200-ml. portions of ether. The ether extracts are combined with the bulk of the product, washed with two 100-ml. portions of water, and then dried over calciiun chloride. After the ether has been removed by distillation, the residue is distilled at reduced pressure from a 125-ml. Claisen flask. N-Ethyl- -chloroaniline is collected at 108-110°/5 mm. or 149-150°/40 mm., 1.5650-1.5661, weight 52-55 g. (87-92%) (Note 5). 

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