Carboxylesterase activities toward pesticide esters in crops and weeds

Gershater, Markus; Sharples, Kate R.; Edwards, Robert

doi:10.1016/j.phytochem.2006.09.019

Cited by 41 publications

(24 citation statements)

References 22 publications

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“…This highly ionized group at physiological pH, especially in the pH range of 5.0-7.5, makes these compounds significantly less lipophilic, and with the exception of picloram (Tables S2 and S4), correlates with their weak stimulation of hypocotyl elongation. Using this set of rules, we anticipated that masked auxins with an ester linkage instead of an amide linkage, which have been reported to better penetrate the leaves then the free acid form, also will stimulate hypocotyl elongation (33,34). Indeed, similar to 533, methyl-2,4-D exhibited a stimulatory effect on hypocotyl growth compared with 2,4-D (Fig.…”

Section: Resultsmentioning

confidence: 99%

New auxin analogs with growth-promoting effects in intact plants reveal a chemical strategy to improve hormone delivery

Savaldi-Goldstein

Baiga²,

Pojer³

et al. 2008

Proc. Natl. Acad. Sci. U.S.A.

102

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Plant growth depends on the integration of environmental cues and phytohormone-signaling pathways. During seedling emergence, elongation of the embryonic stem (hypocotyl) serves as a readout for light and hormone-dependent responses. We screened 10,000 chemicals provided exogenously to light-grown seedlings and identified 100 compounds that promote hypocotyl elongation. Notably, one subset of these chemicals shares structural characteristics with the synthetic auxins, 2,4-dichlorophenoxyacetic acid (2,4-D), and 1-naphthaleneacetic acid (1-NAA); however, traditional auxins (e.g., indole-3-acetic acid [IAA], 2,4-D, 1-NAA) have no effect on hypocotyl elongation. We show that the new compounds act as ''proauxins'' akin to prodrugs. Our data suggest that these compounds diffuse efficiently to the hypocotyls, where they undergo cleavage at varying rates, releasing functional auxins. To investigate this principle, we applied a masking strategy and designed a pro-2,4-D. Unlike 2,4-D alone, this pro-2,4-D enhanced hypocotyl elongation. We further demonstrated the utility of the proauxins by characterizing auxin responses in light-grown hypocotyls of several auxin receptor mutants. These new compounds thus provide experimental access to a tissue previously inaccessible to exogenous application of auxins. Our studies exemplify the combined power of chemical genetics and biochemical analyses for discovering and refining prohormone analogs with selective activity in specific plant tissues. In addition to the utility of these compounds for addressing questions related to auxin and lightsignaling interactions, one can envision using these simple principles to study other plant hormone and small molecule responses in temporally and spatially controlled ways. chemical genetics ͉ light

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Section: Resultsmentioning

confidence: 99%

New auxin analogs with growth-promoting effects in intact plants reveal a chemical strategy to improve hormone delivery

Savaldi-Goldstein

Baiga²,

Pojer³

et al. 2008

Proc. Natl. Acad. Sci. U.S.A.

102

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“…Consistent with the observations that esterase activity leading to herbicide bioactivation is greater in weeds than in crops, the selectivity of cyhalofop butyl was attributed in part to a lack of esterase activity in rice, resulting in lower levels of cyhalofop acid relative to the rates of hydrolysis determined in susceptible weeds (Ruiz-Santaella et al 2006). Similarly, a further analysis of the esterase complement of maize, rice, sorghum, soybean, flax and lucerne, compared with a number of weed species again demonstrated differences in activity, which could contribute to herbicide selectivity mechanisms (Gershater et al 2006).…”

Section: Phase 1 Enzymes -Hydrolasesmentioning

confidence: 98%

New Perspectives on the Metabolism and Detoxification of Synthetic Compounds in Plants

Edwards

Dixon

Cummins

et al. 2010

Plant Ecophysiology

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In attempting to understand the mechanisms by which plants process synthetic compounds we have developed the concept of the 'Xenome', which we define as 'the biosystem responsible for the detection, transport and detoxification of xenobiotics.' In particular the last 10 years have given us unprecedented insights into the proteins responsible for the metabolism and transport of xenobiotics within plant cells and how these systems are regulated. In this review we identify recent advances in our understanding of the xenome and its role in the detoxification and processing of pollutants and pesticides. In particular, we focus on the role of the phase 1 (oxidoreductase/ hydrolytic), phase 2 (bioconjugation), phase 3 (transport) and phase 4 (metabolic recycling) stages of xenobiotic metabolism and the biosensing systems which control their expression. Ultimately, by understanding the capability of the plant xenome to detoxify xenobiotics, we may be able to predict the likely fate and environmental risk of new synthetic compounds entering the environment and food chain.

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“…Metabolism of 2,4-D may be another mechanism for 2,4-D resistance in certain populations, but these populations and resistance mechanism will be discussed in a later section. The bioactivation of ester formulations of 2,4-D by carboxylesterase enzymes is another step in metabolism of 2,4-D ester that has been recently reviewed (Gershater et al 2006, but only the metabolism of 2,4-D acid will be discussed in this section. Side-Chain Cleavage.…”

Section: Uptake and Translocationmentioning

confidence: 99%

2,4-D Past, Present, and Future: A Review

Peterson

McMaster

Riechers³

et al. 2016

Weed technol.

252

208

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Since its discovery and initial commercialization in the 1940s, 2,4-D has been an important tool for weed control in a wide variety of crop and noncrop uses. Work studying its chemistry, physiology, mode of action, toxicology, environmental behavior, and efficacy has not only helped elucidate the characteristics of 2,4-D but also provided basic methods that have been used to investigate the properties of hundreds of herbicides that followed it. Much of the information published by researchers over 60 yr ago is still pertinent to understanding the performance of 2,4-D today. Further, new studies continue to be published, especially regarding the mechanisms of 2,4-D action at the molecular level. New uses for 2,4-D, sometimes enabled by biotechnology, continue to be developed. This review strives to provide an overall understanding of 2,4-D activity in plants, plant sensitivity to 2,4-D, toxicological impacts, and current and future uses.

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Carboxylesterase activities toward pesticide esters in crops and weeds

Cited by 41 publications

References 22 publications

New auxin analogs with growth-promoting effects in intact plants reveal a chemical strategy to improve hormone delivery

New auxin analogs with growth-promoting effects in intact plants reveal a chemical strategy to improve hormone delivery

New Perspectives on the Metabolism and Detoxification of Synthetic Compounds in Plants

2,4-D Past, Present, and Future: A Review

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