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. 1976 Apr;14:93–102. doi: 10.1289/ehp.761493

Chemistry and toxicology of quinoxaline, organotin, organofluorine, and formamidine acaricides.

C O Knowles
PMCID: PMC1475104  PMID: 789072

Abstract

Quinoxaline, organotin, organofluorine, and formamidine compounds are among the newer pesticide chemicals used for acarine control. Included in these four classes are some of the most selective synthetic organic toxicants currently in the acaricide/insecticide arsenal. Oxythioquinox, Plictran (tricyclohexylhydroxytin), Nissol [2-fluoro-N-methyl-N-(1-naphthyl)acetamide], and chlordimeform are examples of quinoxaline, organotin, organofluorine, and formamidine acaricides, respectively. The chemistry and toxicology of these and related compounds are discussed.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Ahmad S., Knowles C. O. Biochemical mode of action of tricyclohexylhydroxytin. Comp Gen Pharmacol. 1972 Jun;3(10):125–133. doi: 10.1016/0010-4035(72)90017-1. [DOI] [PubMed] [Google Scholar]
  2. Ahmad S., Knowles C. O. Metabolism of N'-(4-chloro-o-tolyl)-N,N-dimethylformamidine (chlorphenamidine) and 4'-chloro-o-formotoluidide by rat hepatic microsomal and soluble enzymes. Comp Gen Pharmacol. 1971 Jun;2(6):189–197. doi: 10.1016/0010-4035(71)90010-3. [DOI] [PubMed] [Google Scholar]
  3. Aziz S. A., Knowles C. O. Inhibition of monoamine oxidase by the pesticide chlordimeform and related compounds. Nature. 1973 Apr 6;242(5397):417–418. doi: 10.1038/242417a0. [DOI] [PubMed] [Google Scholar]
  4. Beeman R. W., Matsumura F. Chlordimeform: a pesticide acting upon amine regulatory mechanisms. Nature. 1973 Mar 23;242(5395):273–274. doi: 10.1038/242273a0. [DOI] [PubMed] [Google Scholar]
  5. Benezet H. J., Knowles C. O. N'-(4-Chloro-o-tolyl)-N-methylformamidine (demethylchlordimeform) metabolism in the rat. J Agric Food Chem. 1976 Jan-Feb;24(1):152–154. doi: 10.1021/jf60203a011. [DOI] [PubMed] [Google Scholar]
  6. Carlson G. P., DuBois K. P. Studies on the toxicity and biochemical mechanism of action of 6-methyl-2,3-quinoxalinedithiol cyclic carbonate (morestan). J Pharmacol Exp Ther. 1970 May;173(1):60–70. [PubMed] [Google Scholar]
  7. Desaiah D., Cutkomp L. K., Koch R. B. Inhibition of spider mite ATPases by plictran and three organochlorine acaricides. Life Sci. 1973 Dec 16;13(12):1693–1703. doi: 10.1016/0024-3205(73)90116-1. [DOI] [PubMed] [Google Scholar]
  8. Ercegovich C. D., Witkonton S., Asquith D. Disappearance of N'-(4-chloro-o-tolyl)-N,N-dimethylformamidine from six major fruit crops. J Agric Food Chem. 1972 May-Jun;20(3):565–568. doi: 10.1021/jf60181a005. [DOI] [PubMed] [Google Scholar]
  9. Hashimoto Y., Noguchi T., Mori T., Kitagawa H. Some pharmacologic properties of a new fluorine pesticide, n-methyl-n-(1-naphthyl)monofluoroacetamide. Toxicol Appl Pharmacol. 1968 Sep;13(2):174–188. doi: 10.1016/0041-008x(68)90091-4. [DOI] [PubMed] [Google Scholar]
  10. Ilivicky J., Casida J. E. Uncoupling action of 2,4-dinitrophenols, 2-trifluoromethylbenzimidazoles and certain other pesticide chemicals upon mitochondria from different sources and its relation to toxicity. Biochem Pharmacol. 1969 Jun;18(6):1389–1401. doi: 10.1016/0006-2952(69)90252-4. [DOI] [PubMed] [Google Scholar]
  11. Johannsen F. R., Knowles C. O. Citrate accumulation in twospotted spider mites, house flies, and mice following treatment with the acaricide 2-fluoro-N-methyl-N-(1-naphthyl) acetamide. J Econ Entomol. 1972 Dec;65(6):1754–1756. doi: 10.1093/jee/65.6.1754. [DOI] [PubMed] [Google Scholar]
  12. Johannsen F. R., Knowles C. O. Metabolism of fluenethyl acaricide in the mouse, house fly, and twospotted spider mite. J Econ Entomol. 1974 Feb;67(1):5–12. doi: 10.1093/jee/67.1.5. [DOI] [PubMed] [Google Scholar]
  13. Johannsen F. R., Knowles C. O. Toxicity and action of fluenethyl acaricide and related compounds in the mouse, housefly and twospotted spider mite. Comp Gen Pharmacol. 1974 Mar;5(1):101–110. doi: 10.1016/s0306-3623(74)80014-5. [DOI] [PubMed] [Google Scholar]
  14. Knowles C. O., Gupta A. K. N'-(4-chloro-0-tolyl)-N,N-dimethylformamidine-14C (Galecron) and 4-chloro-0-toluidine-14C metabolism in the white rat. J Econ Entomol. 1970 Jun;63(3):856–859. doi: 10.1093/jee/63.3.856. [DOI] [PubMed] [Google Scholar]
  15. Knowles C. O. Metabolism of two acaricidal chemicals, N'-(4-chloro-o-tolyl)-N,N-dimethylformamidine (chlorphenamidine) and m-([(dimethylamino)methylene]amino)phenyl methylcarbamate hydrochloride (formetanate). J Agric Food Chem. 1970 Nov-Dec;18(6):1038–1047. doi: 10.1021/jf60172a044. [DOI] [PubMed] [Google Scholar]
  16. Knowles C. O., Roulston W. J. Toxicity to Boophilus microplus of formamidine acaricides and related compounds, and modification of toxicity by certain insecticide synergists. J Econ Entomol. 1973 Dec;66(6):1245–1251. doi: 10.1093/jee/66.6.1245. [DOI] [PubMed] [Google Scholar]
  17. Knowles C. O., Shrivastava S. P. Chlordimeform and related compounds: toxicological studies with house flies. J Econ Entomol. 1973 Feb;66(1):75–79. doi: 10.1093/jee/66.1.75. [DOI] [PubMed] [Google Scholar]
  18. Kossmann K., Geissbühler H., Boyd V. F. Specific determination of chlorphenamidine (N'-(4-chloro-o-tolyl)-N,N-dimethylformamidine) in plants and soil material by colorimetry and thin-layer and electron capture gas chromatography. J Agric Food Chem. 1971 Mar-Apr;19(2):360–364. doi: 10.1021/jf60174a029. [DOI] [PubMed] [Google Scholar]
  19. Lin T. H., North H. H., Menzer R. E. The metabolic fate of chlordimeform [N-(4-chloro-o-toly)-N', N'-dimethylformamidine] in human embryonic lung cell cultures. J Agric Food Chem. 1975 Mar-Apr;23(2):257–258. doi: 10.1021/jf60198a041. [DOI] [PubMed] [Google Scholar]
  20. Murakami M., Fukami J. Effects of chlorphenamidine and its metabolites on HeLa cells. Bull Environ Contam Toxicol. 1974 Feb;11(2):184–188. doi: 10.1007/BF01684602. [DOI] [PubMed] [Google Scholar]
  21. Noguchi T., Hashimoto Y., Miyata H. Studies of the biochemical lesions caused by a new fluorine pesticide, n-methyl-n-(1-naphthyl)monofluoroacetamide. Toxicol Appl Pharmacol. 1968 Sep;13(2):189–198. doi: 10.1016/0041-008x(68)90092-6. [DOI] [PubMed] [Google Scholar]
  22. Noguchi T., Hashimoto Y., Mori T., Kano S. [Studies on selective toxicity. IX. Relationship between chemical structure and selective antimicrobial activity of haloacetamide derivatives]. Yakugaku Zasshi. 1968 Dec;88(12):1620–1637. doi: 10.1248/yakushi1947.88.12_1620. [DOI] [PubMed] [Google Scholar]
  23. Witkonton S., Ercegovich C. D. Degradation of N'-(4-chloro-o-tolyl)-N,N-dimethylformamidine in six different fruit. J Agric Food Chem. 1972 May-Jun;20(3):569–573. doi: 10.1021/jf60181a006. [DOI] [PubMed] [Google Scholar]

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