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Chemical Compound Review

AG-K-65821     (1- methylsulfanylethylideneamino) N...

Synonyms: KBioGR_001181, KBioSS_002453, SPBio_001744, AC1L1HFJ, CTK0I2154, ...
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Disease relevance of methomyl

  • After addition of BmT-toxin or methomyl, inhibition of whole cell respiration and swelling of spheroplasts were observed in Escherichia coli cultures producing the novel mitochondrial protein; these effects are similar to those observed with isolated cms-T mitochondria [1].
  • The oral toxic dose causing illness in 50% of those exposed to methomyl was estimated to be 0.15 mg/kg of body weight (estimated range, 0.09-0.31 mg/kg of body weight) [2].
  • Our data indicate that URF13 has two independent mechanisms for toxicity, one that is mediated by T toxin and methomyl and one that is independent of these toxins [3].
  • The URF13 protein, which is encoded by the maize mitochondrial T-urf13 gene, is thought to be responsible for pathotoxin and methomyl sensitivity and male sterility [4].
  • The mutagenic activity of five methyl carbamate insecticides-carbaryl, baygon, BUX-Ten, landrin and methomyl-and their nitroso derivatives were investigated using histidine auxotrophs-his TA98, his TA100, his TA1535, his TA1537 and his TA1538--of Salmonella typhimurium LT2 derived by Ames [5].

Psychiatry related information on methomyl

  • (iii) For substances with reaction times close to the duration of the dry period, the behavior is driven by the length of the time interval between two rain events, as for example, for methomyl [6].

High impact information on methomyl


Chemical compound and disease context of methomyl


Biological context of methomyl


Anatomical context of methomyl

  • URF13 is a membrane protein unique to mitochondria from maize having the Texas male-sterile cytoplasm (cms-T), which is capable of permeabilizing biological membranes in the presence of a family of pathotoxins (T-toxins) produced by certain fungi or the insecticide methomyl [16].
  • Substantial amounts of methomyl (2260-2680 ng/ml) were detected in cerebrospinal fluid and vitreous humor [17].

Associations of methomyl with other chemical compounds

  • The poisoning agents in all cases were positively identified as methomyl or aldicarb by gas chromatography-mass spectrometry [18].
  • Moreover, a different ratio of CREST-positive/CREST-negative micronuclei was observed with the two products, pure methomyl being relatively more active than Lannate 25 in the induction of CREST-positive micronuclei [19].
  • When malate is the substrate oxidized by isolated mitochondria, interaction between the targeted protein and methomyl results in significant inhibition of oxygen uptake [13].
  • Determination of residues of methomyl and oxamyl and their oximes in crops by gas-liquid chromatography of oxime trimethylsilyl ethers [20].
  • Dual counter-current chromatography (dual CCC) has been successfully applied to rapid sample preparation for the simultaneous determination of residual carbaryl, fenobucarb and methomyl in vegetable oil and citrus fruit [21].

Gene context of methomyl


Analytical, diagnostic and therapeutic context of methomyl

  • In addition, URF13 is toxic to insect cells grown in culture without T toxins or methomyl; even a T-toxin-insensitive mutant form of URF13 is lethal to cell cultures [3].
  • The ability of the carboxylate-specific reagent, N,N'-dicyclohexycarbodiimide, to cross-link URF13 was used in conjunction with site-directed mutagenesis to establish that the URF13 tetramer has a central core consisting of a four-alpha-helical bundle which undergoes a conformational change after interaction with T-toxin or methomyl [27].
  • Shift in FTIR spectrum patterns in methomyl-exposed rat spleen cells [28].
  • Eleven patients who suffered methomyl poisoning were admitted to the intensive care unit [29].
  • The distribution of methomyl in different organs of mice was detected by HPLC [24].


  1. A 13-kilodalton maize mitochondrial protein in E. coli confers sensitivity to Bipolaris maydis toxin. Dewey, R.E., Siedow, J.N., Timothy, D.H., Levings, C.S. Science (1988) [Pubmed]
  2. An outbreak of food-borne illness associated with methomyl-contaminated salt. Buchholz, U., Mermin, J., Rios, R., Casagrande, T.L., Galey, F., Lee, M., Quattrone, A., Farrar, J., Nagelkerke, N., Werner, S.B. JAMA (2002) [Pubmed]
  3. Baculovirus expression of the maize mitochondrial protein URF13 confers insecticidal activity in cell cultures and larvae. Korth, K.L., Levings, C.S. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  4. Targeting the maize T-urf13 product into tobacco mitochondria confers methomyl sensitivity to mitochondrial respiration. Chaumont, F., Bernier, B., Buxant, R., Williams, M.E., Levings, C.S., Boutry, M. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  5. Mutagenicity screening of five methyl carbamate insecticides and their nitroso derivatives using mutants of Salmonella typhimurium LT2. Blecvins, R.D., Lee, M., Regan, J.D. Mutat. Res. (1977) [Pubmed]
  6. Modeling the influence of intermittent rain events on long-term fate and transport of organic air pollutants. Jolliet, O., Hauschild, M. Environ. Sci. Technol. (2005) [Pubmed]
  7. Fungal toxins bind to the URF13 protein in maize mitochondria and Escherichia coli. Braun, C.J., Siedow, J.N., Levings, C.S. Plant Cell (1990) [Pubmed]
  8. N,N'-dicyclohexylcarbodiimide cross-linking suggests a central core of helices II in oligomers of URF13, the pore-forming T-toxin receptor of cms-T maize mitochondria. Rhoads, D.M., Kaspi, C.I., Levings, C.S., Siedow, J.N. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  9. Genetic toxicity of methyl methanethiosulfonate on Salmonella typhimurium, Saccharomyces cerevisiae and Nicotiana tabacum. Dorange, J.L., Aranda, G., Cornu, A., Dulieu, H. Mutat. Res. (1983) [Pubmed]
  10. Review of clinical and toxicological features of acute pesticide poisonings in Crete (Greece) during the period 1991-2001. Bertsias, G.K., Katonis, P., Tzanakakis, G., Tsatsakis, A.M. Med. Sci. Monit. (2004) [Pubmed]
  11. Acute pancreatitis subsequent to voluntary methomyl and dichlorvos intoxication. Brahmi, N., Blel, Y., Kouraichi, N., Abidi, N., Thabet, H., Amamou, M. Pancreas (2005) [Pubmed]
  12. Genotoxic effects of the carbamate insecticide, methyomyl. II. In vivo studies with pure compound and the technical formulation, "Lannate 25". Bolognesi, C., Peluso, M., Degan, P., Rabboni, R., Munnia, A., Abbondandolo, A. Environ. Mol. Mutagen. (1994) [Pubmed]
  13. Mitochondrial dysfunction in yeast expressing the cytoplasmic male sterility T-urf13 gene from maize: analysis at the population and individual cell level. Glab, N., Petit, P.X., Slonimski, P.P. Mol. Gen. Genet. (1993) [Pubmed]
  14. Exposure and risk estimation for pesticides in high-volume spraying. de Vreede, J.A., Brouwer, D.H., Stevenson, H., van Hemmen, J.J. The Annals of occupational hygiene. (1998) [Pubmed]
  15. Crystal and molecular structure of carbamate insecticides. 3. Methomyl. Takusagawa, F., Jacobson, R.A. J. Agric. Food Chem. (1977) [Pubmed]
  16. Cross-linking of the cms-T maize mitochondrial pore-forming protein URF13 by N,N'-dicyclohexylcarbodiimide and its effect on URF13 sensitivity to fungal toxins. Kaspi, C.I., Siedow, J.N. J. Biol. Chem. (1993) [Pubmed]
  17. A fatal poisoning caused by methomyl and nicotine. Moriya, F., Hashimoto, Y. Forensic Sci. Int. (2005) [Pubmed]
  18. Carbamate poisoning and oxime treatment in children: a clinical and laboratory study. Lifshitz, M., Rotenberg, M., Sofer, S., Tamiri, T., Shahak, E., Almog, S. Pediatrics (1994) [Pubmed]
  19. Genotoxic effects of the carbamate insecticide methomyl. I. In vitro studies with pure compound and the technical formulation "Lannate 25". Bonatti, S., Bolognesi, C., Degan, P., Abbondandolo, A. Environ. Mol. Mutagen. (1994) [Pubmed]
  20. Determination of residues of methomyl and oxamyl and their oximes in crops by gas-liquid chromatography of oxime trimethylsilyl ethers. Chapman, R.A., Harris, C.R. J. Chromatogr. (1979) [Pubmed]
  21. Application of dual counter-current chromatography for rapid sample preparation of N-methylcarbamate pesticides in vegetable oil and citrus fruit. Ito, Y., Goto, T., Yamada, S., Matsumoto, H., Oka, H., Takahashi, N., Nakazawa, H., Nagase, H., Ito, Y. Journal of chromatography. A. (2006) [Pubmed]
  22. Effects of methomyl and ethanol on behavior in the Sprague-Dawley rat. Bracy, O.L., Doyle, R.S., Kennedy, M., McNally, S.M., Weed, J.D., Thorne, B.M. Pharmacol. Biochem. Behav. (1979) [Pubmed]
  23. Safety/risk assessment of pesticides: principles, procedures and examples. Lu, F.C., Dourson, M.L. Toxicol. Lett. (1992) [Pubmed]
  24. Role of selenium on antioxidant capacity in methomyl-treated mice. El-Khawaga, O.A. Journal of physiology and biochemistry. (2005) [Pubmed]
  25. Evaluation of chronic exposure of the male rat reproductive system to the insecticide methomyl. Mahgoub, A.A., El-Medany, A.H. Pharmacol. Res. (2001) [Pubmed]
  26. Effects of field application of the anti-cholinesterase insecticide methomyl on brain acetylcholinesterase activities in wild Mus musculus. Montz, W.E., Scanlon, P.F., Kirkpatrick, R.L. Bulletin of environmental contamination and toxicology. (1983) [Pubmed]
  27. URF13, a ligand-gated, pore-forming receptor for T-toxin in the inner membrane of cms-T mitochondria. Rhoads, D.M., Levings, C.S., Siedow, J.N. J. Bioenerg. Biomembr. (1995) [Pubmed]
  28. Shift in FTIR spectrum patterns in methomyl-exposed rat spleen cells. Suramana, T., Sindhuphak, R., Dusitsin, N., Posayanonda, T., Sinhaseni, P. Sci. Total Environ. (2001) [Pubmed]
  29. Management of methomyl poisoning. Martinez-Chuecos, J., Molinero-Somolinos, F., Solé-Violàn, J., Rubio-Sanz, R. Human & experimental toxicology. (1990) [Pubmed]
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