2,2-Dichlorovinyl dimethyl phosphate

In the body, metrifonate converts to the active metaboUte dichlorvos, (2,2-dichlorovinyl dimethyl phosphate), which is responsible for the inhibition of the enzyme acetylcholinesterase in the susceptible worm. This effect alone is unlikely to explain the antischistosomal properties of metrifonate (19). Clinically, metrifonate is effective only against infection caused by S. haematobium. Metrifonate is administered in three doses at 2-wk intervals (17). The dmg is well tolerated. Side effects such as mild vertigo, nausea, and cramps are dose-related. This product is not available in the United States. The only manufacturer of metrifonate is Bayer A.G. of Leverkusen, Germany. 

Among organophosphates dichlorvos (2,2-dichlorovinyl dimethyl phosphate) and pirimiphos methyl (0-[2-(diethylamino)-6-methyl-4-pyr-imidinyl]0,0-dimethylphosphorothioate) are important contaminants for the durum wheat industry. Dichlorvos is one of the most widely used pesticides worldwide in the storage of many products, such as com, rice, and durum wheat, finding widespread use in most European countries... 

DDVP 2,859 s, 1645s, 1,462 m, 761s, 661m, 341m 2.2-Dichlorovinyl dimethyl phosphate... 

Vapona [Shell], TM for an insecticide that contains more than 93% 2,2-dichlorovinyl dimethyl phosphate and less than 7% active, related compounds. 

DDVP Mutagenicity 2,2-dichlorovinyl dimethyl phosphate) Neurotoxicity... 

Pesticides as a class contain 2 widely quoted examples of ambiguity between mutagenic activity and carcinogenicity. Dichlorvos (2,2-dichlorovinyl dimethyl phosphate), an organophosphate insecticide, and ziram (bis(dimethyldithio-carbamate)zinc), a dithiocarbamate fungicide, are confirmed bacterial mutagens [13]. 

Metrifonate (trichloifon bearcil) is an organophosphorus compound used as an insecticide and then as an anthelmintic, especially for S. haematobium. Metrifonate is a prodrug that is converted nonen-zymatically to dichlorvos (2,2-dichlorovinyl dimethyl phosphate, DDVP), a potent cholinesterase... 

SYNONYMS DDVP, 2,2 -dichlorovinyl dimethyl phosphate, bibesol, tetravos, 2,2 -dichloroethanol dimethyl phosphate. 

Synonyms/Trade Names DDVP 2,2-Dichlorovinyl dimethyl phosphate ... 

Dichlorovinyl dimethyl phosphate 2,2-Dichlorovinyl dimethyl phosphoric acid ester Dichlorovos. See Dichlorvos... 

As the intention was to synthesize new inhibitors of acetylcholinesterase, the anticholinesterase activity of the above-described phosphonates and phosphonothioates was studied. In 1978, Zakharova et al. examined the activity of dichlorovinyl-substituted carbaboranyl phosphonates 27-30 toward acetylcholinesterase and butyrylcholinesterase. As these compounds are analogs of 2,2-dichlorovinyl dimethyl phosphate (dichlorvos or DDVP) (26), their activity was compared with the activity of this known insecticide. As shown in Table 2.1, compounds 27-30 exhibit remarkably lower activity toward both enzymes than the phosphate DDVP. The replacement of an alkoxyl group with the bulky carborane moiety increases the steric demand of the compound and therefore hinders binding on the surface of the enzyme and the following phosphorylation of the hydroxyl group of serine. Additionally, the type of inhibition changed in snch a way that the compounds exhibit reversible instead of irreversible binding. The substituents at the second carbon atom of the carborane core have only minor influence on the inhibitor activity. 

A subsequent pilot experiment revealed that Tradescantia inflorescences were sensitive to a commercial insecticide whose active ingredient consisted largely of 2, 2-dichlorovinyl dimethyl phosphate. This agent, however, produced mostly bud blasting with little or no mutational response. 

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