Herbicidal 4-hydroxyphenylpyruvate dioxygenase inhibitors—A review of the triketone chemistry story from a Syngenta perspective

Beaudegnies, Renaud; Edmunds, Andrew; Fraser, Torquil; Hall, Roger G.; Hawkes, Timothy R.; Mitchell, Glynn; Schaetzer, Jürgen; Wendeborn, Sebastian; Wibley, J.E.A.

doi:10.1016/j.bmc.2009.03.015

Cited by 204 publications

(199 citation statements)

References 40 publications

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“…Mesotrione (2-[4-(methylsulfonyl)-2-nitrobenzoyl]-1,3-cyclohexanedione) belongs to the triketone class of 4-hydroxyphenylpyruvate dioxygenase (HPPD)-inhibiting herbicides (Beaudegnies et al, 2009). Molecular information regarding plant HPPD gene sequences and expression patterns is limited (for review, see Pallett, 2000;Kim and Petersen, 2002;Riechers and Stanford, 2002;Matringe et al, 2005), and only a single expressed HPPD gene was detected in waterhemp (Riggins et al, 2010).…”

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“…Following mesotrione treatment, carotenoid biosynthesis is inhibited in sensitive plants, resulting in bleaching and necrosis. In particular, new leaves and meristems are primarily affected due to the need for protective carotenoids and tocopherols in photosynthetic tissues (Triantaphylidès and Havaux, 2009) and the systemic nature of mesotrione, which is translocated in the phloem Beaudegnies et al, 2009).…”

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Distinct Detoxification Mechanisms Confer Resistance to Mesotrione and Atrazine in a Population of Waterhemp

et al. 2013

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Previous research reported the first case of resistance to mesotrione and other 4-hydroxyphenylpyruvate dioxygenase (HPPD) herbicides in a waterhemp (Amaranthus tuberculatus) population designated MCR (for McLean County mesotrione-and atrazineresistant). Herein, experiments were conducted to determine if target site or nontarget site mechanisms confer mesotrione resistance in MCR. Additionally, the basis for atrazine resistance was investigated in MCR and an atrazine-resistant but mesotrione-sensitive population (ACR for Adams County mesotrione-sensitive but atrazine-resistant). A standard sensitive population (WCS for Wayne County herbicide-sensitive) was also used for comparison. Mesotrione resistance was not due to an alteration in HPPD sequence, HPPD expression, or reduced herbicide absorption. Metabolism studies using whole plants and excised leaves revealed that the time for 50% of absorbed mesotrione to degrade in MCR was significantly shorter than in ACR and WCS, which correlated with previous phenotypic responses to mesotrione and the quantity of the metabolite 4-hydroxy-mesotrione in excised leaves. The cytochrome P450 monooxygenase inhibitors malathion and tetcyclacis significantly reduced mesotrione metabolism in MCR and corn (Zea mays) excised leaves but not in ACR. Furthermore, malathion increased mesotrione activity in MCR seedlings in greenhouse studies. These results indicate that enhanced oxidative metabolism contributes significantly to mesotrione resistance in MCR. Sequence analysis of atrazine-resistant (MCR and ACR) and atrazine-sensitive (WCS) waterhemp populations detected no differences in the psbA gene. The times for 50% of absorbed atrazine to degrade in corn, MCR, and ACR leaves were shorter than in WCS, and a polar metabolite of atrazine was detected in corn, MCR, and ACR that cochromatographed with a synthetic atrazineglutathione conjugate. Thus, elevated rates of metabolism via distinct detoxification mechanisms contribute to mesotrione and atrazine resistance within the MCR population.

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Distinct Detoxification Mechanisms Confer Resistance to Mesotrione and Atrazine in a Population of Waterhemp

et al. 2013

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“…Dayan et al, 2007). Triketone 제초제는 p-hydroxphenylpyruvate dioxygenase (HPPD) 효소를 저해하는 것으로 나 타났다 (Beaudegnies et al, 2009). …”

Section: 지속적 잡초관리는 유기농업과 관행농업을 위하여 주요 한 도전이 되고 있다 미래의 잡초관리는 종합적 잡초관리unclassified

Status and Perspective of Bioherbicde Development for Organic Weed Management

Pyon¹,

Lee²,

Park³

2017

Weed & Turfgrass Science

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ABSTRACT. Weed management under organic farming systems is very problematic since organic agriculture does not allow synthetic herbicides. Bioherbicide is needed to develop for weed management in organic agriculture systems. This review covers current status and perspectives of bioherbicide development for effective nonchemical weed management in organic farming systems. Bioherbicides are products of natural origin derived from living organisms, and more specifically bacteria, fungus and plants including natural metabolites for weed control. Bioherbicides derived from microorganisms or natural molecules are currently available on the pesticide markets. Devine, Lockdown (Collego), BioMal, Camperico, Organo-Sol and Opportune were derived from bacteria, Woad Warrior, Smolder, Mygogen, Chontrol Paste, Starritor and Phoma derived from fungus, and Katoun (pelargonic acid) and Beloukha were derived from plants. Corn gluten meal products and plant essential oils products are also available for nonselective weed control in organic agriculture. Organic weed management methods may be more feasible in small scale farming and high-value crops, and bioherbicides may be applied with other weed control practices in organic farming systems.

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“…HPPD-inhibiting herbicides show many advantages, such as low application rate, low toxicity, broad-spectrum weed control (including herbicide-resistant weed biotypes), excellent crop selectivity and benign environmental effects [13,14]. Several of them are currently used as selective broad leaf herbicides including triketones, pyrazoles, isoxazoles, diketone nitriles and benzophenones over the last two decades.…”

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confidence: 99%

3D Pharmacophore-based Virtual Screening, Docking Approaches toward the Discovery of Novel HPPD Inhibitors

Fu¹,

Sun²,

Yi³

et al. 2017

Preprint

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p-Hydroxyphenylpyruvate dioxygenase (HPPD) is not only the useful molecular target in treating life-threatening tyrosinemia type I, but also an important target for chemical herbicides. A combined in silico structure-based pharmacophore and molecular docking based virtual screening were performed to identify novel potential HPPD inhibitors. The complex based pharmacophore model (CBP) with 0.721 of ROC used for screening compound showed remarkable ability to retrieve known active ligands from decoy molecule. The ChemDiv database was screened using CBP-Hypo2 as a 3D query, and the best-fit hits subjected to molecular docking with two methods of LibDock and CDOCKER in Accelrys Discovery Studio 2.5(DS 2.5) to discern interactions with key residues at the active site of HPPD. 4 Compounds with top rank in HipHop model and well-known binding model were finally chosen as identification of lead compounds with potentially inhibitory effects on active site of target. The results provided powerful insight to the development of novel HPPD inhibitors herbicides using computational techniques.

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Herbicidal 4-hydroxyphenylpyruvate dioxygenase inhibitors—A review of the triketone chemistry story from a Syngenta perspective

Cited by 204 publications

References 40 publications

Distinct Detoxification Mechanisms Confer Resistance to Mesotrione and Atrazine in a Population of Waterhemp

Distinct Detoxification Mechanisms Confer Resistance to Mesotrione and Atrazine in a Population of Waterhemp

Status and Perspective of Bioherbicde Development for Organic Weed Management

3D Pharmacophore-based Virtual Screening, Docking Approaches toward the Discovery of Novel HPPD Inhibitors

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