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'Metolachlor' in keywords
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1991 (2)
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1982 (1)
1Author    Hans Moser, Grety Rihs, Hanspeter Sauter, Entwicklung Forschung, PflanzenschutzRequires cookie*
 Title    Der Einfluß yon Atropisomerie und chiralem Zentrum auf die biologische Aktivität des Metolachlor The Influence of Atropisomerism and Chiral Centre on the Biological Activity of Metolachlor  
 Abstract    The four stereoisomers of the grass herbicide Metolachlor, the isomerism of which is based on a combination of a chiral centre and a chiral axis, were prepared, and their absolute configurations determined by X-ray analysis. The synthesis was achieved by using optically active starting materials and new optically active carbamates as intermediates. The herbicidal activity is mainly influenced by the chiral centre, the S-isomers being the most active ones. 
  Reference    Z. Naturforsch. 37b, 451—462 (1982); eingegangen am 20. August 1981 
  Published    1982 
  Keywords    Chloro-acetanilide, Metolachlor, Atropisomerism, Chiral Centre, Biological Activity 
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 TEI-XML for    default:Reihe_B/37/ZNB-1982-37b-0451.pdf 
 Identifier    ZNB-1982-37b-0451 
 Volume    37 
2Author    DonaldE M Oreland, FrederickT. CorbinRequires cookie*
 Title    Influence of Safeners on the in vivo and in vitro Metabolism of Bentazon and Metolachlor by Grain Sorghum Shoots: a Preliminary Report  
 Abstract    Metabolism of bentazon and m etolachlor by excised shoots and a microsomal fraction iso­ lated from the shoots, of 3-day-old, dark-grown, grain sorghum (Sorghum bicolor cv. Funk G 522 DR) seedlings was studied. The effects of seed treatments, on the subsequent m etabo­ lism of the herbicides, with the safeners naphthalic anhydride, oxabetrinil, and CGA 133205 were compared against surface-sterilization and Captan-treatm ents. Bentazon was aryl hydroxylated in both in vivo and in vitro studies with the hydroxylated derivative undergoing glycosylation only under in vivo conditions. Both shoots and microsomes isolated from shoots of safener-treated seed showed enhanced metabolism of bentazon relative to the controls. In­ hibition by tetcyclacis, a potent inhibitor of plant cytochrome P-450 monooxygenases, in both the in vivo and in vitro studies, and a requirement for N A DPH in the in vitro studies suggested that the formation of hydroxybentazon was mediated by a cytochrome P-450 monooxygenase. Metolachlor was metabolized to polar material and O-desmethylmetolachlor under in vivo conditions. Only the demethylated product was formed in vitro. Shoots isolated from safener-treated seed showed enhanced form ation o f polar com pounds which were assumed to have arisen from conjugation with glutathione. Tetcyclacis did not affect the formation of the polar components. However, the form ation of O-desmethylmetolachlor was depressed in the shoots excised from safener-treated seed under both in vivo and in vitro conditions. Tetcyclacis com ­ pletely prevented form ation of the demethylated metabolite. Hence, formation of this m eta­ bolite is considered to be P-450 mediated. The differential response obtained with the safeners, i.e., stimulation of aryl hydroxylation o f bentazon and depression of metolachlor demethyla-tion, suggests that the reactions are probably catalyzed by different cytochrome P-450 m ono­ oxygenases. 
  Reference    Z. Naturforsch. 46c, 906—914 (1991); received M arch 26 1991 
  Published    1991 
  Keywords    Microsomes, Metolachlor, Bentazon, Cytochrome P-450, Mixed Function Oxidase 
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 TEI-XML for    default:Reihe_C/46/ZNC-1991-46c-0906.pdf 
 Identifier    ZNC-1991-46c-0906 
 Volume    46 
3Author    DonaldE. Moreland, FrederickT. Corbin, WilliamP. Novitzky, CarolE. Parker, KennethB. TomerRequires cookie*
 Title    Metabolism of Metolachlor by a Microsomal Fraction Isolated from Grain Sorghum ( Sorghum bicolor) Shoots  
 Abstract    A microsomal fraction isolated from the shoots of 3-to 4-day-old, dark-grown, grain sor­ ghum (Sorghum bicolor cv. Funk G 522 D R) seedlings was characterized. The preparations had a cytochrome P-450 content that varied from approximately 90 to 150 pmol P-450/mg protein with cytochrome P-420 varying from 0 to 3% of the P-450 content. Type I difference spectra were formed with cinnamic acid and metolachlor, and a type II spectrum was formed with tetcyclacis. In short-term assays with [14C]metolachlor as substrate, the preparations produced a single time-dependent product that separated on silica gel TLC plates developed in benzene/ acetone (2:1, v/v). R F values for metolachlor and the metabolite were approximately 0.70 and 0.48, respectively. The microsomal reaction required N A D PH and oxygen, and was inhibited by carbon monoxide, with the inhibition being partially reversed by actinic light. Compounds known to inhibit the activity of cytochrome P-450 monooxygenases (piperonyl butoxide, tet­ cyclacis, and tridiphane) also prevented formation of the metabolite. Identity of the metabolite was confirmed by TLC and positive ion thermospray LC/MS to be 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-hydroxy-l-methylethyl)acetamide. Hence, the reaction catalyzed by the sorghum microsomes involved O-demethylation of the methoxypropyl side chain of meto­ lachlor. 
  Reference    Z. Naturforsch. 45c, 558—564 (1990); received November 9 1989 
  Published    1990 
  Keywords    Microsomes, Metolachlor, Cytochrome P-450, Mixed Function Oxidase, Herbicide Metabolism 
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 TEI-XML for    default:Reihe_C/45/ZNC-1990-45c-0558.pdf 
 Identifier    ZNC-1990-45c-0558 
 Volume    45 
4Author    C.K C Ottingham, K. K. HatziosRequires cookie*
 Title    Influence of the Safener Benoxacor on the Metabolism of Metolachlor in Corn  
 Abstract    The herbicide safener benoxacor (CGA -154281) is effective in protecting corn from meto­ lachlor injury. Glutathione-S-transferase (GST) activity of corn seedlings was stimulated by low concentrations of benoxacor as was the formation of a polar metabolite identified as the glutathione (GSH) conjugate of metolachlor. A similar degree of enhancement of metolachlor metabolism was observed in both a metolachlor-tolerant ('Cargill 7567') and a metolachlor-susceptible ('Northrup-King 9283') corn line. The total GSH content o f shoots o f the meto-lachlor-susceptible corn hybrid was not affected by benoxacor treatment, but an increase was noted for shoots of the tolerant corn hybrid. The two corn hybrids with differential tolerance to metolachlor also differ in their dose response to benoxacor with higher safener concentra­ tions failing to induce or inhibit GST activity of the tolerant 'Cargill 7567' corn line. Stimula­ tion of GST activity and a corresponding enhanced rate of metolachlor metabolism can ac­ count for the safening effect of benoxacor. These mechanism of action of dichloroacetamide safeners. 
  Reference    Z. Naturforsch. 46c, 846—849 (1991); received March 26 1991 
  Published    1991 
  Keywords    Metolachlor, Glutathione-S-transferase, Glutathione, Benoxacor, Corn, Zeam ays L 
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 TEI-XML for    default:Reihe_C/46/ZNC-1991-46c-0846.pdf 
 Identifier    ZNC-1991-46c-0846 
 Volume    46