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Metabolism and Degradation of Porphyrin Biosynthesis Inhibitor Herbicides

  • Chapter
Peroxidizing Herbicides

Abstract

The metabolism and degradation of herbicides are key factors determining their weed control activity, crop selectivity, environmental fate and safety to non-target organisms. Numerous compounds which inhibit protoporphyrinogen oxidase (i.e. peroxidizing herbicides) have been commercialized or are under development. These compounds span a wide range of use patterns, environmental fate profiles and toxicological properties which result at least in part from their different susceptibilities to plant, animal and microbial metabolism and/or abiotic degradation. In this chapter, we describe the metabolism and degradation of 19 commercialized or candidate peroxidizing herbicides in a number of plant, animal, microbial, soil, water and light systems. These herbicides fall into two subclasses: (1) p-nitro diphenyl ethers, and (2) heterocyclic-substituted benzenes. Data from published reports have been augmented by unpublished results from regulatory studies, when available. As for many large herbicide classes (and the peroxidizing herbicides are one of the largest), susceptibility to metabolism and abiotic degradation is quite dependent on chemical structure, and generalizations about such properties are difficult. For example, some peroxidizing herbicides are relatively recalcitrant to metabolism in plants and rely on soil sorption/placement for crop selectivity. Others are readily metabolized in certain plants and postemergence crop selectivity often results from metabolic inactivation. Similarly, there is wide variability among these herbicides in susceptibility to soil microbial degradation. However, one generalization is that peroxidizing herbicides are subject to the same metabolic transformations as are other agrichemicals including aryl and aliphatic hydroxylation, hydrolysis, deesterification, nitro reduction, O-dealkylation, and conjugation with glutathione as well as multiple secondary conjugation reactions.

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Authors and Affiliations

  1. DuPont Agricultural Products, DuPont Kabushiki Kaisha, Tokyo, Japan

    Hiroyasu Aizawa

  2. DuPont Agricultural Products, Stine-Haskell Research Center, Newark, Delaware, USA

    Hugh M. Brown

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  1. Hiroyasu Aizawa
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  1. Department of Plant Physiology and Biochemistry, University of Konstanz, D-78457, Konstanz, Germany

    Peter Böger

  2. Department of Physiology and Biochemistry, Tamagawa University, Machida-shi, Tokyo, 194-8610, Japan

    Ko Wakabayashi

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Aizawa, H., Brown, H.M. (1999). Metabolism and Degradation of Porphyrin Biosynthesis Inhibitor Herbicides. In: Böger, P., Wakabayashi, K. (eds) Peroxidizing Herbicides. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-58633-0_14

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  • DOI: https://doi.org/10.1007/978-3-642-58633-0_14

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