The Chemical Structure and Herbicidal Activity of Alloxydim-sodium and Related Compounds

Iwataki, Isao; Hirono, Y.

doi:10.1016/b978-0-08-022349-0.50033-3

Cited by 13 publications

(8 citation statements)

References 1 publication

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“…Although there are several works that study alloxydim photodegradation in different conditions [10,11,21], its mechanism of photolysis is not well-known. involving these species are one of the most common routes of pesticide transformation.…”

Section: Structure Elucidation Of Phototransformation Products Degramentioning

confidence: 97%

Photochemical behavior of alloxydim herbicide in environmental waters. Structural elucidation and toxicity of degradation products

Sandín‐España

Sevilla-Morán

Calvo

et al. 2013

Microchemical Journal

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Section: Structure Elucidation Of Phototransformation Products Degramentioning

confidence: 97%

Photochemical behavior of alloxydim herbicide in environmental waters. Structural elucidation and toxicity of degradation products

Sandín‐España

Sevilla-Morán

Calvo

et al. 2013

Microchemical Journal

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“…1). These compounds exhibit a remarkably similar spectrum of phytotoxicity on both annual and perennial grasses without affecting broadleaf plants (6,13,14). Studies on the uptake, translocation, and metabolic fate of these herbicides in tolerant and susceptible plants have shown that the selectivity for monocotyledonous species is probably not due to differential metabolism of the compounds to nonherbicidal forms, or to differential uptake or transport (4,24,25).…”

mentioning

confidence: 99%

Cyclohexanedione Herbicides Are Selective and Potent Inhibitors of Acetyl-CoA Carboxylase from Grasses

Rendina

Felts²

1988

Plant Physiol.

116

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ci Over the past 10 years a series of substituted 1,3-cyclohexanediones (alloxydim, sethoxydim, and clethodim) has been introduced as postemergence grass herbicides for use in broadleaf crops (Fig. 1). These compounds exhibit a remarkably similar spectrum of phytotoxicity on both annual and perennial grasses without affecting broadleaf plants (6,13,14). Studies on the uptake, translocation, and metabolic fate of these herbicides in tolerant and susceptible plants have shown that the selectivity for monocotyledonous species is probably not due to differential metabolism of the compounds to nonherbicidal forms, or to differential uptake or transport (4,24,25). These results suggest that the tolerance of broadleaf crops and weeds is based on the insensitivity of the target site to these compounds.Recent studies on the mode of action of sethoxydim (2, 3, 10) have shown that de novo fatty acid biosynthesis is inhibited by this herbicide in susceptible plants. In order to elucidate the mode of action of clethodim (16), we began to examine the individual enzymes involved in the biosynthetic pathway. Both flavonoid and fatty acid biosynthetic pathways in plants share the first two steps which are catalyzed by acetyl-CoA synthetase and acetyl-CoA carboxylase. In addition, fatty acid synthesis in plants involves six separate enzymes which use ACP1-bound intermediates. In this report, we describe the potent inhibition in grasses of the second enzyme common to these pathways, acetylCoA carboxylase (EC 6.4.1.2), by alloxydim, sethoxydim, and clethodim, and the much weaker inhibition of this enzyme in tolerant broadleaf species.

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“…In this sense, a first approximation to the most significant in silico results of individual alloxydim and several photoproducts (i.e., imine tautomers 1 and 2) are presented in Table 2 . Moreover, the amine byproduct from alloxydim (see structure within Table 2 ) was subjected to QSAR analysis for comparison ( Table 2 ), taking into account that several previous works have shown its possible formation in other environmental conditions [ 37 ].…”

Section: Resultsmentioning

confidence: 99%

Assessing the Effects of Alloxydim Phototransformation Products by QSAR Models and a Phytotoxicity Study

Villaverde¹,

Santín-Montanyá²,

Sevilla-Morán³

et al. 2018

Molecules

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Once applied, an herbicide first makes contact with leaves and soil. It is known that photolysis can be one of the most important processes of dissipation of herbicides in the field. However, degradation does not guarantee detoxification and can give rise to byproducts that could be more toxic and/or persistent than the active substance. In this work, the photodegradation of alloxydim herbicide in soil and leaf cuticle surrogates was studied and a detailed study on the phytotoxicity of the main byproduct on sugar beet, tomato, and rotational crops was performed. Quantitative structure–activity relationship (QSAR) models were used to obtain a first approximation of the possible ecotoxicological and environmental implications of the alloxydim and its degradation product. The results show that alloxydim is rapidly degraded on carnauba and sandy loam soil surfaces, two difficult matrices to analyze and not previously studied with alloxydim. Two transformation products that formed in both matrices were identified: alloxydim Z-isomer and imine derivative (mixture of two tautomers). The phytotoxicity of alloxydim and the major byproduct shows that tomato possesses high sensitivity to the imine byproduct, while wheat crops are inhibited by the parent compound. This paper demonstrates the need to further investigate the behavior of herbicide degradation products on target and nontarget species to determine the adequate use of herbicidal products to maximize productivity in the context of sustainable agriculture.

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The Chemical Structure and Herbicidal Activity of Alloxydim-sodium and Related Compounds

Cited by 13 publications

References 1 publication

Photochemical behavior of alloxydim herbicide in environmental waters. Structural elucidation and toxicity of degradation products

Photochemical behavior of alloxydim herbicide in environmental waters. Structural elucidation and toxicity of degradation products

Cyclohexanedione Herbicides Are Selective and Potent Inhibitors of Acetyl-CoA Carboxylase from Grasses

Assessing the Effects of Alloxydim Phototransformation Products by QSAR Models and a Phytotoxicity Study

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