Animal Metabolism of Insecticides, Bovine Metabolism of Organophosphorus Insecticides. Metabolic Fate of O,O-Dimethyl O-(2,4,5-trichlorophenyl) Phosphorothioate in Rats and a Cow

Plapp, Frederick W.; Casida, J. E.

doi:10.1021/jf60091a002

Cited by 69 publications

(10 citation statements)

References 9 publications

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“…2. The pathways are similar to those proposed for other organophosphorus esters such as bromophos (Stiasni et al 1967) and ronnel (Plapp and Casida 1958). The formation of O-methyl phenylphosphonothioic acid (no, 3) probably occurs by oxidative dearylation or by esterase catalyzed hydrolysis of leptophos, or a combination of reactions similar to those demonstrated with other phosphorothionate insecticides (Yang et al 1971;Matsumura and Hogendijk 1964;Nakatsugawa et al 1969).…”

Section: Discussionsupporting

confidence: 78%

The metabolism ofO-(4-bromo-2, 5-dichlorophenyl)O-methyl phenylphosphonothioate (leptophos) in white mice and on cotton plants

Holmstead

Fukuto

March

1973

Arch. Environ. Contam. Toxicol.

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The metabolism of 14C-labeled leptophos (O-methyl O-4-bromo-2, 5-dichtorophenyl phenylphosphonothioate), a new phosphonothioate insecticide chemical, was examined in the white mouse and the cotton plant. Leptophos, administered orally to the mouse, is rapidly metabolized and excreted as degradation products, principally in the urine. The major degradation products are 4-bromo-2, 5-dichlorophenol (in the form of conjugates), O-methyl phenylphosphonothioic acid, methyl phenylphosphonic acid, and phenylphosphonic acid. Small amounts of unchanged leptophos and leptophos oxon occur in the mouse feces. In general, the same alteration products are also obtained when leptophos is applied to the leaf surface of cotton plants. However, leptophos is quite stable on the cotton plant and the major portion of the radioactive material recovered from the plant is unchanged leptophos. The results indicate that leptophos is useful as a long-term residual insecticide without the problem of biomagnification in the food chain.

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Section: Discussionsupporting

confidence: 78%

The metabolism ofO-(4-bromo-2, 5-dichlorophenyl)O-methyl phenylphosphonothioate (leptophos) in white mice and on cotton plants

Holmstead

Fukuto

March

1973

Arch. Environ. Contam. Toxicol.

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“…between the bovine and the rat in growth response to ronnel is not understood 9 Plapp and Casida (1958) found a similar metabolic pathway for ronnel in cows and rats, but detoxification and excretion appeared to be much slower in the cow than in the rat. The possibility that this difference in metabolic rate could be responsible for the stimulatory effect of ronnel on growth in steers is speculation.…”

Section: Resultsmentioning

confidence: 93%

Effects of Ronnel on Growth, Endocrine Function and Blood Measurements in Steers and Rats

Rumsey¹,

Huang²,

Bitman³

1981

Journal of Animal Science

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Four feeding trials were conducted to determine (1) how the organophosphate ronnel affects thyroid and adrenal circulating hormone levels and blood profile measurements of beef steers and (2) whether the effects of ronnel observed in beef steers could be produced in growing rats. In trial 1, four groups of eight steers each were given either no ronnel or 4 mg ronnel/kg body weight daily in diets fed at either limited (1.8% of body weight) or ad libitum intake. After 7 weeks, intake levels, but not ronnel treatments, were reversed during a 1-week transition period, and feeding was continued for another 7 weeks. In trial 2, four groups of six steers each were given 0, 44, 88 or 176 ppm ronnel premixed in diets fed ad libitum for 18 weeks. Actual ronnel intakes averaged 0, 1.01, 2.12 and 4.73 mg/kg body weight daily in trial 2. In trials 3 and 4 , growth and intake were measured in 64 and 32 growing Sprague-Dawley rats, respectively, fed levels of ronnel ranging from 0 to 100 ppm in the diet. In trial 3, blood plasma was analyzed at various times for triiodothyronine (T3), thyroxine (T4), cholesterol and total lipid content. In trial 1, the concentration of Plasma T4 was 1.31 times higher in steers fed ronnel that in control steers. In trial 2, plasma T4 was 1.30 times higher in steers fed 176 ppm ronnel, the level that improved growth, than in steers fed the lower ronnel levels. Circulating levels of T3, cortisol and aldosterone were similar for both control and ronnel-fed steers. Serum cholesterol concentrations were consistently higher in ronnel-fed steers. The data indicated that the growth-promoting effect of ronnel in steers may be associated with a shift in thyroid function. Effects of ronnel in steers were not observed in rats, demonstrating a species difference between steers and rats.

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“…The insecticide was rapidly metabolized and excreted. Plapp and Casida (1958) incubated an organophosphate, Trolene, with bovine rumen fluid and showed hydrolysis at the phosphorus-oxygenmethyl group to yield phenyl phosphoric acids. Some dimethyl phosphothioic acid was found, indicating the possible occurrence of oxidative metabolism as well as hydrolysis.…”

mentioning

confidence: 99%

Rumen Bacterial and Protozoal Responses to Insecticide Substrates

Williams¹,

Robbins²,

Gutierrez³

et al. 1963

Applied Microbiology

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Insecticides containing organophosphate, chlorinated hydrocarbon, and carbamate were tested with bovine ruminal ingesta fractions. Rumen bacteria exposed to insecticide levels of 0 to 500 ppm in rumen fluid for 4 hr were inoculated into rumen fluid-starch feed extract medium. No apparent significanit bacterial couInt inhibitions were noted. Also, when insecticides were used as carbon sources at concentrations of 500 ppm in carbohydrate-limited media, no increases in bacterial counts were indicated. Warburg manometric data showed that paraffin oil-Triton X-155 preparations of dimethoate, Diazinon, lindane, Thiodan and Sevin stimulated gas production in holotrich protozoa. Entodiniumn simplex, an oligotrich, produced less gas with insecticide substrates per unit of dry weight thani did an Isotricha sp. Rumen bacteria and plant debris fractions from ruminal ingesta provided with insecticides did not give increased manometric responses over the endogenous control vessels. Washed suspensions of I. intestinalis produced volatile fatty acids in excess of the endogenous suspensions when provided insecticide substrates. Thiodan dissimilation by I. intestinalis was followed colorimetrically with 15 % loss in substrate in 1 hr of incubation at 39 C. Diazinon-C14 substrate uptake was demonstrated with suspensions of E. simplex and I. intestinalis. Rumen ciliates are suggested as a possible means for screening out useful insecticides susceptible to microbial dissimilation for use on forage and other cattle-feed crops.

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Animal Metabolism of Insecticides, Bovine Metabolism of Organophosphorus Insecticides. Metabolic Fate of O,O-Dimethyl O-(2,4,5-trichlorophenyl) Phosphorothioate in Rats and a Cow

Cited by 69 publications

References 9 publications

The metabolism ofO-(4-bromo-2, 5-dichlorophenyl)O-methyl phenylphosphonothioate (leptophos) in white mice and on cotton plants

The metabolism ofO-(4-bromo-2, 5-dichlorophenyl)O-methyl phenylphosphonothioate (leptophos) in white mice and on cotton plants

Effects of Ronnel on Growth, Endocrine Function and Blood Measurements in Steers and Rats

Rumen Bacterial and Protozoal Responses to Insecticide Substrates

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