The Chemical Transformation of Atrazine in Corn Seedlings

Raveton, Muriel; Ravanel, Patrick; Kaouadji, Mourad; Bastide, J.; Tissut, Michel

doi:10.1006/pest.1997.2303

Cited by 24 publications

(25 citation statements)

References 27 publications

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“…But in contrast to Raveton et al (1997a), we observed a 100% degradation of atrazine within 48 h already at a ratio of DIMBOA to atrazine of 100:1, while Raveton et al (1997a) observed full degradation only at DIMBOA to atrazine ratios of more than 1000:1. According to Raveton et al (1997a) concentrations of DIMBOA as high as 10 m M were required to obtain hydroxylation of atrazine, while we observed the hydroxylation of atrazine, DEA, and DIA already at concentrations that were about 200 times lower. The lower detection limit might be due to differences in the analytical methods.…”

Section: Discussioncontrasting

confidence: 96%

“…The observation that increasing DIMBOA concentrations enhanced the degradation of atrazine, DEA, and DIA has also been reported by Raveton et al (1997a), who studied the effect of different purified benzoxazinones on the degradation of atrazine, and by Ioannou et al (1980), who described a catalyzing effect of DIMBOA on diazinon degradation. But in contrast to Raveton et al (1997a), we observed a 100% degradation of atrazine within 48 h already at a ratio of DIMBOA to atrazine of 100:1, while Raveton et al (1997a) observed full degradation only at DIMBOA to atrazine ratios of more than 1000:1. According to Raveton et al (1997a) concentrations of DIMBOA as high as 10 m M were required to obtain hydroxylation of atrazine, while we observed the hydroxylation of atrazine, DEA, and DIA already at concentrations that were about 200 times lower.…”

Section: Discussionsupporting

confidence: 60%

“…After this time no more significant changes were observed in the pesticide concentration of the mixtures. Additionally, DIMBOA is known to decompose to MBOA in aqueous solution with a half‐life of about 5.5 h at pH 6.8 and about 50 h at pH 5.0 and 28°C (Grambow et al, 1986), and MBOA does not induce the hydroxylation of atrazine (Raveton et al, 1997a). All samples were analyzed using high performance liquid chromatography (HPLC)–UV, and HPLC–mass spectrometry (MS) measurements were performed to confirm the identity of the formed metabolites.…”

Section: Methodsmentioning

confidence: 99%

“…In grasses, benzoxazinones appear to play an important role in this metabolism. Several authors have postulated that the major benzoxazinone of corn, DIMBOA, is involved in the natural defense of plants against bacteria, fungi, and insects (Bohidar et al, 1986; Figueroa et al, 1999; Leszczynski et al, 1995; Niemeyer, 1988a; Wilkes et al, 1999), in iron transport (Pethõ, 1992a, 1992b; Tipton and Buell, 1970) and in the detoxification of s ‐triazine herbicides by hydroxylation within the plants (Hamilton and Moreland, 1962; Raveton et al, 1997a; Tipton et al, 1971). Benzoxazinones are also known to catalyze the hydrolysis of the organophosphate pesticide diazinon (Ioannou et al, 1980), and have been found in several grasses, for example, Sorghum spp.…”

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confidence: 99%

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Effect of Corn Root Exudates on the Degradation of Atrazine and Its Chlorinated Metabolites in Soils

et al. 2005

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DIMBOA (3,4-dihydro-2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one), a major benzoxazinone of Poaceae plants, was isolated and purified from corn seedlings. The effect of isolated and purified DIMBOA on the degradation of atrazine [2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine], and its toxic breakdown products, desethylatrazine [2-chloro-4-amino-6-(isopropylamino)-s-triazine; DEA] and desisopropylatrazine [2-chloro-4-(ethylamino)-6-amino-s-triazine; DIA], was studied in the absence of plants using batch experiments, while the effect of corn root exudates on these compounds was determined in hydroponic experiments. Degradation experiments were performed in the presence and absence of 50 microM, 1 mM, or 5 mM DIMBOA resulting in ratios of DIMBOA to pesticide of 1:1, 20:1, and 100:1. We observed a 100% degradation of atrazine to hydroxyatrazine within 48 h at a ratio of DIMBOA to atrazine of 100:1. DIMBOA had the largest effect on atrazine, while it was about three times less effective on DEA and DIA. Corn (Zea mays L. cv. LG 2185) was exposed to 10 mg L(-1) of either atrazine, DEA, or DIA for 11 d in a growth chamber experiment. Up to 4.3 micromol L(-1) d(-1) of hydroxyatrazine were formed in the nutrient solutions by plants exposed to atrazine, while the formation of hydroxylated metabolites from plants exposed to DEA and DIA was smaller and also delayed. The formation of hydroxylated metabolites increased in the solution with plant age in all atrazine, DEA, and DIA treatments. HMBOA (3,4-dihydro-2-hydroxy-7-methoxy-2H-1,4-benzoxazin-3-one), the lactam precursor of DIMBOA, and a tentatively identified derivative of MBOA (2,3-dihydro-6-methoxy-benzoxazol-2-one) were detected in the corn root exudates. Mass balance calculations revealed that up to 30% of the disappearance of atrazine and DEA, and up to 10% of DIA removal from the solution medium in our study could be explained by the formation of hydroxylated metabolites in the solution itself. Our results show that higher plants such as corn have the potential to promote the hydrolysis of triazine residues in soils by exudation of benzoxazinones.

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Section: Discussioncontrasting

confidence: 96%

Section: Discussionsupporting

confidence: 60%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

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Effect of Corn Root Exudates on the Degradation of Atrazine and Its Chlorinated Metabolites in Soils

et al. 2005

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“…Leaching of atrazine in most soils is limited. Einhellig (1989) and Raveton et al (1997) studied the transformation and detoxification of atrazine in seedlings. Phenolics are one of the many secondary metabolites implicated in allelopathy and accumulate in soils causing inhibition of both seed germination and overall growth of many plant species (Inderjit, 1998).…”

Section: Introductionmentioning

confidence: 99%

Effects of Atrazine and Phenolic Compounds on Germination and Seedling Growth of Some Crop Plants.

Burhan¹,

Shaukat²

2000

Pakistan J. of Biological Sciences

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The phytotoxicity of atrazine and three phenolic compounds (i.e., benzoic, p-coumaric and caffeic acids) was investigated. The germination of six test species was reduced by atrazine in the order: pearl-millet > wheat> turnip> carrot> corn> mustard. Whereas, the phenolic compounds affected the germination of pearl-millet in the order: caffeic acid> benzoic acid> p-coumaric acid. Atrazine in conjunction with the three phenolic compounds exhibited synergistic effect on the process of germination and seedling growth.

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Comparative Diffusion of Atrazine inside Aqueous or Organic Matrices and inside Plant Seedlings

Raveton

Schneider²,

Desprez-Durand

et al. 1999

Pesticide Biochemistry and Physiology

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The Chemical Transformation of Atrazine in Corn Seedlings

Cited by 24 publications

References 27 publications

Effect of Corn Root Exudates on the Degradation of Atrazine and Its Chlorinated Metabolites in Soils

Effect of Corn Root Exudates on the Degradation of Atrazine and Its Chlorinated Metabolites in Soils

Effects of Atrazine and Phenolic Compounds on Germination and Seedling Growth of Some Crop Plants.

Comparative Diffusion of Atrazine inside Aqueous or Organic Matrices and inside Plant Seedlings

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