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Initial Metabolism of Acetochlor in Tolerant and Susceptible Seedlings

Published online by Cambridge University Press:  12 June 2017

E. Jay Breaux
E. Jay Breaux*
Affiliation:
Monsanto Agricultural Products Co., St. Louis, MO 63167
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Abstract

The initial metabolism of acetochlor [2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide] in tolerant and susceptible plants was examined to determine if metabolism is a factor in the selective phytotoxicity of this herbicide. Six crop and ten weed species were used. In every case acetochlor was converted initially to thioether conjugates. In thirteen of the species, initial conjugation was with glutathione (GSH). The homoglutathione (hGSH) conjugate was formed in three legumes. Tolerant plant seedlings metabolized acetochlor more readily than susceptible plant seedlings. Based on these results, acetochlor detoxification is a primary factor in the selective phytotoxicity of this herbicide.

Keywords

Chloroacetanilide selectivityherbicide detoxificationherbicide metabolismZea maysGlycine maxIpomoea purpureaConvolvulus arvensisPhaseolus aureusXanthium pensylvanicumAbutilon theophrastiCassia obtusifoliaSesbania exaltataBrassica kaberMedicago sativaCyperus esculentusSorghum bicolorTriticum aestivumEchinochloa crus-galliIPOPUCONARXANPEABUTHCASOBSEBEXBRAKACYPESSORVUECHCG
Type
Physiology, Chemistry, and Biochemistry
Information
Weed Science , Volume 35 , Issue 4 , July 1987 , pp. 463 - 468
Copyright
Copyright © 1987 by the Weed Science Society of America 

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References

Literature Cited

1. Armstrong, T. F., Meggitt, W. F., and Penner, D. 1973. Absorption, translocation, and metabolism of alachlor by yellow nutsedge. Weed Sci. 21:357–360.CrossRefGoogle Scholar
2. Breaux, E. J. 1986. Identification of the initial metabolites of acetochlor in corn and soybean seedlings. J. Agric. Food Chem. 34:884–888.CrossRefGoogle Scholar
3. Breaux, E. J., Patanella, J. E., and Sanders, E. F. 1987. Chloroacetanilide herbicide selectivity: The analysis of glutathione and homoglutathione in tolerant, susceptible and safened seedlings. J. Agric. Food Chem. In press.CrossRefGoogle Scholar
4. Chandler, J. M., Basler, E., and Santelmann, P. W. 1974. Uptake and translocation of alachlor in soybean and wheat. Weed Sci. 22:253–258.CrossRefGoogle Scholar
5. Diesperger, H. and Sandermann, H. 1979. Soluble and microsomal glutathione-S-transferase activities in pea seedlings (Pisum sativum L.). Planta 146:643–648.CrossRefGoogle ScholarPubMed
6. Dixon, G. A. and Stoller, E. W. 1982. Differential toxicity, absorption, translocation, and metabolism of metolachlor in corn (Zea mays) and yellow nutsedge (Cyperus esculentus). Weed Sci. 30:225–230.CrossRefGoogle Scholar
7. Environmental Protection Agency. 1980. 2-Chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide: Metolachlor registration standard. Google Scholar
8. Ezra, G., Stephenson, G. R., and Lamoureux, G. L. 1986. Metabolism of 14C metazachlor and action of the safener 145-138 in corn. Abstr. Weed Sci. Soc. Am. 26:92.Google Scholar
9. Fuerst, E. P. and Gronwald, J. W. 1986. Induction of rapid metabolism of metolachlor in sorghum (Sorghum bicolor) shoots by CGA-92194 and other antidotes. Weed Sci. 34:354–361.CrossRefGoogle Scholar
10. Harvey, R. G. 1974. Susceptibility of seven annual grasses to herbicides. Weed Res. 14:51–55.CrossRefGoogle Scholar
11. Hatzios, K. K. 1983. Effects of CGA-43089 on responses of sorghum (Sorghum bicolor) to metolachlor combined with ozone or antioxidants. Weed Sci. 31:280–284.CrossRefGoogle Scholar
12. Jablonkai, I. and Dutka, F. 1985. Effect of absorption and translocation on acetochlor susceptibility in plants. J. Radioanal. Nucl. Chem. Letters. 94:45–52.CrossRefGoogle Scholar
13. Jaworski, E. G. 1969. Analysis of the mode of action of herbicidal chloroacetamides. J. Agric. Food Chem. 17:165–170.CrossRefGoogle Scholar
14. Lamoureux, G. L. and Davidson, K. L. 1975. Mercapturic acid formation in the metabolism of propachlor, CDAA, and flurodifen in the rat. Pest. Physiol. Biochem. 5:497–506.CrossRefGoogle Scholar
15. Lamoureux, G. L., Stafford, L. E., and Tanaka, F. S. 1971. Metabolism of 2-chloro-N-isopropylacetanilide (propachlor) in the leaves of corn, sorghum, sugarcane and barley. J. Agric. Food Chem. 19:346–350.CrossRefGoogle ScholarPubMed
16. Lay, M. M. and Casida, J. E. 1976. Dichloroacetamide antidotes enhance thiocarbamate sulfoxide detoxification by elevating corn root glutathione content and glutathione-S-transferase activity. Pest. Physiol. Biochem. 6:442–456.Google Scholar
17. Narasaiah, D. B. and Harvey, R. G. 1977. Alachlor placement in the soil as related to the phytotoxicity to maize (Zea mays L.) seedlings. Weed Res. 17:163–168.CrossRefGoogle Scholar
18. Shimabukuro, R. H., Lamoureux, G. L., and Frear, D. S. 1978. Glutathione conjugation: a mechanism for herbicide detoxification and selectivity in plants. Pages 133–149 in Pallos, F. M. and Casida, J. E., eds. “Chemistry and Action of Herbicide Antidotes”. Academic Press, New York.Google Scholar