Hostname: page-component-78c5997874-v9fdk Total loading time: 0 Render date: 2024-11-17T17:17:56.942Z Has data issue: false hasContentIssue false

Degradation of Anilide Herbicides by Propham-Adapted Microorganisms

Published online by Cambridge University Press:  12 June 2017

George W. Mcclure*
Affiliation:
Bóyce Thompson Inst. for Plant Res., Yonkers, NY 1070L

Abstract

A mixture of microorganisms cultured under nonsterile conditions on propham (isopropyl carbanilate) herbicide as the sole carbon source was tested for its ability to degrade a number of chlorinated and nonchlorinated anilide compounds. In separate tests under pure-culture conditions, species of the microbial mixture reacted individually in a manner similar to the nonsterile whole. The microorganisms grew and respired rapidly on nonchlorinated anilides, but ring chlorination depressed respiration and inhibited growth. Studies on the dimethylphenylureas indicated that the two methyl groups were primarily responsible for the biological stability of these compounds. All other anilides were degraded by hydrolysis of the side chain followed by metabolic degradation of the ring. Appearance of aniline in the medium depended on the relative rates of production by side chain hydrolysis and disappearance by ring degradation. Acylanilides were hydrolyzed more rapidly than carbanilates and chlorinated rings were degraded much more slowly than unchlorinated rings. Chlorination affected rates of ring degradation and microbial respiration in the following order (most rapid to least rapid): 0 > 2,4 > 2,4,5 > 3 > 4 ≥ 3,4. It is proposed that this unexpected degradative sequence might be explained in terms of the degree of microbial toxicity in the system generated by the formation of chloroazobenzenes from chloroaniline intermediates.

Type
Research Article
Copyright
Copyright © 1974 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. Alexander, M. 1965. Persistence and biological reactions of pesticides in soils. Proc. Soil Sci. Soc. Amer. 29:17.Google Scholar
2. Alexander, M. and Lustigman, B.K. 1966. Effect of chemical structure on microbial degradation of substituted benzenes. J. Agr. Food Chem. 14:410413.Google Scholar
3. Bartha, R. 1968. Biochemical transformations of anilide herbicides in soil. Agr. Food Chem. 16:602604.Google Scholar
4. Bartha, R., Lanzilotta, R.P., and Pramer, D. 1967. Stability and effects of some pesticides in soil. Appl. Microbiol. 15:6775.Google Scholar
5. Bartha, R., Linke, H.A.B., and Pramer, D. 1968. Pesticide transformations: production of chloroazobenzenes from chloroanilines. Science 161:582583.Google Scholar
6. Bartha, R. and Pramer, D. 1967. Pesticide transformation to aniline and azo compounds in soil. Science 156:16171618.Google Scholar
7. Baskakov, Y.A. and Mel'nikov, N.N. 1954. Synthesis and physiological activity on plants of isopropyl esters of some arylcarbamic acids. Zk. Obshch. Khim. 24:376379. C.A. 48:8465a.Google Scholar
8. Dalton, R.L., Evans, A.W., and Rhodes, R.C. 1965. Disappearance of diuron in cotton field soils. Proc. S. Weed Conf. 18:72.Google Scholar
9. Geissbuhler, H., Haselbach, C., Aebi, H., and Ebner, L. 1963. The fate of N'-(4-chlorophenoxy)-phenyl-NH-dimethylurea (C-1983) in soils and plants. III. Breakdown in soils and plants. Weed Res. 3:277297.Google Scholar
10. Hansch, C. 1969. A quantitative approach to biochemical structure-activity relationships. Accounts Chem. Res. 2:232239.Google Scholar
11. Kaufman, D.D. 1967. Degradation of carbamate herbicides in soil. J. Agr. Food Chem. 15:582591.Google Scholar
12. Kearney, P.C. 1965. Purification and properties of an enzyme responsible for hydrolyzing phenylcarbamates. J. Agr. Food Chem. 13:561564.Google Scholar
13. Kearney, P.C. and Kaufman, D.D. 1965. Enzyme from soil bacterium hydrolyzes phenylcarbamate herbicides. Science 147:740.Google Scholar
14. McClure, G.W. 1972. Accelerated degradation of phenylcarbamates in soil by a mixed suspension of IPC-adapted microorganisms. J. Environ. Qual. 1:177–176.Google Scholar
15. Pease, H.L. 1962. Separation and colorimetric determination of monuron and diuron residues. J. Agr. Food Chem. 10:279281.Google Scholar
16. Weisburger, J.H. and Weisburger, E.K. 1966. Chemicals as causes of cancer. Chem. Eng. News 44(6):124142.Google Scholar
17. Whiteside, J.S. and Alexander, M. 1960. Measurement of microbiological effects of herbicides. Weeds 8:204213.Google Scholar