Hostname: page-component-8448b6f56d-cfpbc Total loading time: 0 Render date: 2024-04-24T11:38:14.766Z Has data issue: false hasContentIssue false
  • English
  • Français

Effects of CGA-92194 on the Chemical Reactivity of Metolachlor with Glutathione and Metabolism of Metolachlor in Grain Sorghum (Sorghum bicolor)

Published online by Cambridge University Press:  12 June 2017

Paul Zama  and
Kriton K. Hatzios
Paul Zama
Affiliation:
Dep. Plant Pathol., Physiol. and Weed Sci., Virginia Polytechnic Inst. and State Univ., Blacksburg, VA 24061
Kriton K. Hatzios
Affiliation:
Dep. Plant Pathol., Physiol. and Weed Sci., Virginia Polytechnic Inst. and State Univ., Blacksburg, VA 24061
Get access Rights & Permissions [Opens in a new window]

Abstract

In laboratory experiments, the safener CGA-92194 {α-[(1,3-dioxolan-2-yl-methoxy)imino] benzeneacetonitrile} increased the in vitro chemical reactivity of the herbicide metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide] for glutathione (GSH) when tested at 1, 50, and 100 μM. Pretreatment of sorghum [Sorghum bicolor (L.) Moench. cv. ‘G623’] seeds with the safener CGA-92194 (1.25 g ai/kg of seeds) enhanced significantly the amount of 14C-metolachlor absorbed by the roots and translocated to the shoots and leaves of grain sorghum seedlings grown hydroponically in a nutrient solution. Thin-layer chromatographic analysis of methanol-soluble extracts from roots or shoots and leaves of sorghum seedlings treated with 14C-metolachlor revealed the detection of 8 to 10 metabolites of this herbicide. One of the major metabolites detected was tentatively identified as the conjugate of metolachlor with GSH. A safener-induced stimulation of metolachlor metabolism via conjugation to GSH was observed in sorghum seedlings grown from seeds pretreated with CGA-92194. Addition of tridiphane [2-(3,5-dichlorophenyl)-2-(2,2,2-trichloroethyl)oxirane], a potent inhibitor of plant GSH-S-transferase enzymes, to the nutrient solution of hydroponically grown sorghum seedlings reduced the formation of GS-metolachlor in both control and safener-treated seedlings and minimized the stimulatory effect of the safener CGA-92194 on the conjugation of metolachlor to GSH. It is suggested that the safener CGA-92194 may protect grain sorghum against injury from the herbicide metolachlor by stimulating the spontaneous and enzymatic conjugation of this herbicide with GSH.

Keywords

Tridiphaneabsorptiontranslocationherbicide safener
Type
Physiology, Chemistry, and Biochemistry
Information
Weed Science , Volume 34 , Issue 6 , November 1986 , pp. 834 - 841
Copyright
Copyright © 1986 by the Weed Science Society of America 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Literature Cited

1. Breaux, E. J. and Patanella, J. E. 1985. Chloroacetanilide herbicide selectivity: The initial metabolism of acetochlor in tolerant and susceptible seedlings. Plant Physiol. Suppl. 77:55.Google Scholar
2. Brinker, R., Schafer, D., Drake, R., Boeken, G., and Frazier, H. 1982. The effectiveness of MON-4606 as a seed safener against alachlor and acetochlor in grain sorghum. Proc. Br. Crop Prot. Conf.–Weeds 2:469–474.Google Scholar
3. Cherry, J. H. 1973. Molecular Biology of Plants: A Text-Manual. Columbia Univ. Press. 204 pp.Google Scholar
4. Darmstadt, G. L., Balke, N. E., and Schrader, L. E. 1983. Use of corn root protoplasts in herbicide absorption studies. Pestic. Biochem. Physiol. 19:172–183.Google Scholar
5. Devlin, D. L., Moshier, L. J., Russ, O. G., and Stahlman, P. W. 1983. Antidotes reduce injury to grain sorghum (Sorghum bicolor) from acetanilide herbicides. Weed Sci. 31:790–795.Google Scholar
6. Dixon, G. A. and Stoller, 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. Ellis, F. J., Peek, J. E., Boehle, J. Jr., and Muller, G. 1980. Effectiveness of a new safener for protecting sorghum (Sorghum bicolor) from metolachlor injury. Weed Sci. 28:1–5.Google Scholar
8. Ezra, G., Dekker, J. M., and Stephenson, G. R. 1985. Tridiphane as a synergist for herbicides in corn (Zea mays) and proso millet (Panicum miliaceum). Weed Sci. 33:287–290.Google Scholar
9. Ezra, G., Rusness, D. G., Lamoureux, G. L., and Stephenson, G. R. 1985. The effect of CDAA (N,N-diallyl-2-chloroacetamide) pretreatments on subsequent CDAA injury to corn (Zea mays L.). Pestic. Biochem. Physiol. 23:108–115.Google Scholar
10. 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.Google Scholar
11. Hatzios, K. K. 1983. Herbicide antidotes: Development, chemistry and mode of action. Adv. Agron. 36:264–316.Google Scholar
12. Hatzios, K. K. and Penner, D. 1982. Metabolism of Herbicides in Higher Plants. Burgess Publishing Co., Minneapolis, MN. 142 pp.Google Scholar
13. Hoagland, D. R. and Arnon, D. I. 1950. The water-culture method for growing plants without soil. Circ. 347. California Agric. Exp. Stn. 32 pp.Google Scholar
14. Jachetta, J. J. and Radosevich, S. R. 1981. Enhanced degradation of atrazine by corn (Zea mays). Weed Sci. 29:37–44.Google Scholar
15. Jaworski, E. G. 1975. Chloroacetamides. Pages 349–376 in Kearney, P. C. and Kaufman, D. D., eds. Degradation of Herbicides. Marcel-Dekker, New York.Google Scholar
16. Krause, A., Hancock, W. S., Minard, R. D., Freyer, A. S., Honeycutt, R. C., LeBaron, H. M., Paulson, D. L., Liu, S. Y., and Bollag, J. M. 1985. Microbial transformation of the herbicide metolachlor by a soil actinomycete. J. Agric. Food Chem. 33:585–589.Google Scholar
17. Lamoureux, G. L. and Rusness, D. G. 1983. Glutathione-S-transferase inhibition as the basis of DOWCO 356 synergism of atrazine. Am. Chem. Soc., Div. of Pestic. Chem., Abstr. 115. Washington, DC.Google Scholar
18. Lamoureux, G. L. and Rusness, D. G. 1982. Malonylcysteine conjugates as end-products of glutathione conjugate metabolism in plants. Pages 295–300 in Miyamoto, J. and Kearney, P. C., eds. Pesticide Chemistry: Human Welfare and the Environment. Pergamon Press, New York.Google Scholar
19. Lamoureux, G. L. and Rusness, D. G. 1981. Catabolism of glutathione conjugates of pesticides in higher plants. Pages 133–164 in Rosen, J. D., Magee, P. S., and Casida, J. E., eds. Sulfur in Pesticide Action and Metabolism. ACS Symp. Ser. No. 158. Am. Chem. Soc., Washington, DC.Google Scholar
20. 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.Google Scholar
21. Leavitt, J.R.C. and Penner, D. 1979. In vitro conjugation of glutathione and other thiols with acetanilide herbicides and EPTC sulfoxide and the action of the herbicide antidote R-25788. J. Agric. Food Chem. 27:533–536.CrossRefGoogle Scholar
22. Leek, G. L. and Penner, D. 1982. Role of metabolism in CGA-43089 protection of sorghum from metolachlor injury. Abstr. Weed Sci. Soc. Am. 22:97.Google Scholar
23. Lindley, H. 1962. The reaction of thiol compounds and chloroacetamides. 2. The reaction between chloroacetamide and cysteine peptides. Biochem. J. 82:418–425.Google Scholar
24. Mozer, T. J., Tiemeier, D. C., and Jaworski, E. G. 1983. Purification and characterization of corn glutathione S-transferase. Biochemistry. 22:1068–1072.Google Scholar
25. Paradies, I., Ebert, E., and Elstner, E. F. 1981. Metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl) acetamide] and the metolachlor safener CGA-43089 (α-cyanomethoximino)-benzoacetonitrile) in sorghum seedlings: Correlations between morphological effects and ethylene formation. Pestic. Biochem. Physiol. 15:209–212.Google Scholar
26. Parker, C. 1983. Herbicide antidotes – a review. Pestic. Sci. 14:40–48.Google Scholar
27. Rufener, J., Nyffeler, A., and Peek, J. W. 1982. CGA-92194, a new safener to protect sorghum from injurious effects of metolachlor. Proc. Br. Crop Prot. Conf.–Weeds. 2:461–467.Google Scholar
28. Winkle, M. E., Leavitt, J. R., and Burnside, D. C. 1980. Acetanilide-antidote combinations for weed control in corn (Zea mays) and sorghum (Sorghum bicolor). Weed Sci. 28:699–704.CrossRefGoogle Scholar
29. Zama, P. and Hatzios, K. K. 1986. Influence of CGA-92194 on metolachlor uptake and metabolism by sorghum. Proc. South. Weed Sci. Soc. 39:416.Google Scholar
30. Zorner, S. P. 1985. In vivo kinetics of glutathione-S-transferase inhibition by tridiphane. Proc. South. Weed Sci. Soc. 38:484.Google Scholar
31. Zorner, P. 1983. The influence of preemergence triazine applications on foliar tridiphane treatments. Proc. North Cent. Weed Control Conf. 38:121.Google Scholar
32. Zorner, P., Stafford, S., and McCall, P. 1983. Physiological interactions between tridiphane and atrazine in panicoid grasses. Proc. North Cent. Weed Control Conf. 38:109.Google Scholar