Octamethyl pyrophosphoramide

Rider JA, Moeller HC, Puletti EJ, et al. 1969. Toxicity of parathion, systox, octamethyl pyrophosphoramide, and methyl parathion in man. Toxicol Appl Pharmacol 14 603-611. 

Toxic compounds that can be absorbed to a marked degree by a living plant through either its roots or its leaves have been called by British investigators systemic insecticides. Schrader (38) first found this peculiar property in certain acetals of 2-fluoroethanol and bis-(2-fluoroethoxy) methane, as well as in certain compounds of his organic phosphorus series, notably bis(dimethylamido)fluophosphate and octamethyl pyrophosphoramide. 

Octamethyl pyrophosphoramide is a colorless oil, completely soluble in water, benzene, acetone, and many other common organic solvents except the paraffinic hydrocarbons. Its hydrolysis rate has not been measured, but it appears stable in the absence of alkali. In England, this systemic insecticide has been used to control aphids on hops. There it has been calculated that only a negligible quantity of the poison ultimately may find its way into the beer made from the hops. Despite calculations of this sort, the use of octamethyl pyrophosphoramide on food or fodder crops in this country is definitely not to be recommended. However, it may prove useful if properly applied to control certain insects, especially those attacking ornamental plants, such as rosebushes, and possibly on the cotton aphid and grape phylloxera. The compound has only recently been made available experimentally. 

Analogs of octamethyl pyrophosphoramide which act as systemic insecticides are the isomeric symmetrical (I) and unsymmetrical (II) diethyl bis(dimethylamido)pyrophosphates ... 

According to VNIIGINTOKS, potent toxic agents (PTA), where the fated dose (FD, J is less than 50 mg/ kg, are not introduced into agriculture, are not produced in the USSR, and are not imported from abroad [12]. In actual fact, Risk Class I OPPs with an FD for laboratory animals of less than 50 mg/kg were not only actively used, but were also produced in the USSR for many years (including such OPPs as parathion, demeton, octamethyl pyrophosphoramide, methyl ethyl... 

In the mid-1950s, octamethyl pyrophosphoramide was tested on wheat in the Stavropol Krai, and in the Kiev Oblast on gardens [A2]. Octamethyl pyrophosphoramide concentrations were 1.0-3.0 mg/m3 when fruit trees were manually sprayed, and 0.5 mg/m3 in the signaler s work zone when sprayed from the air [58]. The MPC, established considerably later, was much lower 0.02 mg/ m3. When spraying cotton from the air in Tajikistan, the concentrations were 0.8-1.5 mg/m3 in the air of the field airport, and 3.0 mg/m3 in the signaler s work zone. Workers were observed to have decreased cholinesterase activity. 

One of the most important systemic insecticides is octamethyl-pyrophosphoramide (O.M.P.A. or schradan or pestox III) (I). 

Cross-tolerance between disulfoton and another organophosphate, chlorpyrifos, was observed in mice (Costa and Murphy 1983b). Because of this cross-tolerance, a benefit is derived as a result of this interaction. In the same study, propoxur-tolerant mice were tolerant to disulfoton but not vice versa. Propoxur (a carbamate) is metabolized by carboxylesterases, and these enzymes are inhibited in disulfoton-tolerant animals disulfoton-tolerant animals are more susceptible to propoxur and/or carbamate insecticides than are nonpretreated animals. In another study, disulfoton-tolerant rats were tolerant to the cholinergic effects of octamethyl pyrophosphoramide (OMPA) but not parathion (McPhillips 1969a, 1969b). The authors were unable to explain why the insecticides OMPA and parathion caused different effects. 

McPhillips JJ, Coon JM. 1966. Adaptation to octamethyl pyrophosphoramide in rats. Toxicol Appl Pharmacol 8 66-76. 

In 1952, Rider, Ellinwood, and Coon (7) demonstrated that rats can become tolerant to octamethyl pyrophosphoramide (OMPA). Since then it has been shown that rats can acquire tolerance to a variety of organophosphorus cholinesterase inhibitors. Typical of such reports is that of Bombinski and DuBois (2), who administered 0,0-diethyl S-2-ethyl-2-mercaptoethyl phosphorodithioate (Di-Syston) to rats each day for periods as long as 60 days. Signs of poisoning appeared after 2 days, but began to subside after 7-10 days, even though the activity of brain cholinesterase remained at or about 20% of its normal value from the 5th day onward. 

SYNS MANGANESE(2+), TRIS(OCTAMETHYLDI-PHOSPHORAMIDE-Op,Op )-, (OC-6-11)-, DIPERCHLORATE PERCHLORIC ACID, MANGANESE(2+) SALT, compounded with 3 mols. of OCTAMETHYL-PYROPHOSPHORAMIDE... 

Ethylbenzyl chloride Ethylene dibromide V,V -Dinitroethylenediamine Hexaethyl tetraphosphate M ethylbenzyl alcohol m-Benzenedisulfonic acid Methylbenzyl chloride V-Bromosuccinimide Octamethyl pyrophosphoramide p-Aminosalicylic acid Pentaerythritol tetranitrate Tris-(/3-chloroethyl) amine Tetraethylammonium bromide Tetraethyl pyrophosphate 2,2,6,6-Tetramethylolcyclohexanol... 

Schradan. Schradan. octamethyl pyrophosphoramide. OMPA. frr.r bisdimethylaminophusphonous anhydride (Pestox III), is a viscous liquid that is miscible with water and soluble in most otganic solvents. It is not hydmiy/ed by alkalies or water but is hydrolyzed by acids. Schradan is used as a sy.stemic insecticide for plants, being absorbed by... 

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