Comparative metabolism of famoxadone in fish,plants and animals

The fate and comparative metabolism of famoxadone in fish, plants and animals were evaluated. Famoxadone residues were retained by the fish after exposure (BCF 2800), mainly in the viscera; however, rapid and complete elimination/depuration of the absorbed residues occurred within seven days after the exposed fish were placed in untreated water. Minimal absorption, translocation, and metabolism of famoxadone were observed in grape and potato plants after foliar treatment. Metabolism of famoxadone in the wheat plants, rats, goats, and poultry was extensive. Transfer of ¹⁴C-residues to the wheat grain, milk, eggs, organs and tissues was minimal. Common metabolic reactions of famoxadone in plants and animals include aryl hydroxylation, cleavage of the anilino-oxazolidinedione and phenoxy-phenyl ether linkages, opening of the oxazolidinedione ring and conjugation.     

Effect of dose rate and mixtures of fungicides on selection for QoI resistance in populations of Plasmopara viticola

Resistance to QoI fungicides (strobilurins, famoxadone and fenamidone) in populations of Plasmopara viticola (Berk & Curt) Berlese & de Toni developed soon after their introduction in France and Italy. Current resistance management strategies include limitation of the number of applications, use of mixtures and alternation of fungicides with different modes of action. The selection pressure resulting from QoI fungicides applied alone or in mixtures with non-QoI fungicides was investigated in whole plant experiments under controlled conditions. QoI-resistant populations of P. viticola gradually reverted to full sensitivity following consecutive transfers to untreated plants, suggesting that resistant phenotypes were less competitive than sensitive ones. When cycled on QoI-treated plants, reduction in sensitivity was greater for the QoI fungicide which had greater intrinsic activity on P. viticola. Sensitivity decreased at each subsequent cycle, resulting in almost full resistance after four generations. Mixture experiments indicated that selection pressure was affected most by the dose of the QoI fungicide and the nature of the partner fungicide. Folpet delayed selection pressure most effectively when it was associated with famoxadone or azoxystrobin. Mancozeb was least effective at reducing the rate of selection compared with the QoI alone, and fosetyl-aluminium was intermediate. Higher rates of selection were recorded when the dose of the QoI fungicide, solo or in a mixture, was increased from 1 to 4 microg ml(-1). Increasing the dose of the non-QoI partner fungicide in the mixture from 10 to 30 microg ml(-1) resulted in reduced selection pressure. These results suggest that the choice of the fungicide partner and its dosage in the mixture can significantly affect the success of QoI resistance management strategies under practical conditions.     

易保在苹果和土壤中的残留动态研究

在北京市海淀区进行了易保68.75%水分散粒剂在苹果上的残留动态和最终残留试验,用HPLC测定了其有效成分恶唑菌酮的残留量。恶唑菌酮的最低检出量为2.0×10-10g,在苹果中的最低检出浓度为0.004 mg.kg-1,在土壤中的最低检出浓度为0.002 mg.kg-1。在苹果中的平均回收率为91.5%~92.3%,变异系数为0.13%~3.18%,在土壤中的平均回收率为89.7%~100.6%,变异系数为2.10%~10.10%,符合农药残留分析的要求。结果表明,恶唑菌酮在苹果上的半衰期为11.6 d,在土壤中的半衰期为6.8 d。按推荐剂量和推荐剂量的两倍施用的情况下,恶唑菌酮在苹果中的残留量为0.048~0.406 mg.kg-1,土壤中的残留量为0.057~0.539 mg.kg-1,均低于最大残留限量。     

吡唑醚菌酯·噁唑菌酮30%水分散粒剂高效液相色谱分析

建立了在同一色谱条件下测定混剂中吡唑醚菌酯和噁唑菌酮含量的方法。采用ODS C18、5μm为填料的不锈钢柱和二极管阵列检测器分离,以甲醇+水(体积比为80∶20)为流动相,在254nm波长下,经保留时间定性确证,峰面积外标法进行定量分析。结果表明:吡唑醚菌酯与噁唑菌酮的线性相关系数分别为0.999 5和0.999 6;变异系数分别为0.68%和0.45%;平均加标回收率分别为100.28%和100.32%。     

Mode of action of famoxadone

Famoxadone is a preventative and curative fungicide recently developed for plant disease control. The molecule and its oxazolidinone analogs (OADs) are potent inhibitors of mitochondrial electron transport, specifically inhibiting the function of the enzyme ubiquinol:cytochrome c oxidoreductase (cytochrome bc₁). Visible absorbance spectral studies on the purified enzyme suggested that famoxadone bound close to the low potential heme of cytochrome b. This binding mode was confirmed in competitive binding experiments by studying the displacement of a radiolabelled OAD from submitochondria. EPR studies on the binding of famoxadone to submitochondria and purified bc₁ suggested its binding mode was more like that of myxothiazol than that of stigmatellin (ligands known to bind near the low potential heme). Zoospores of Phytophthora infestans, when given low concentrations of famoxadone and other OADs, were observed to cease oxygen consumption and motility within seconds and later the cells disintegrated, releasing the cellular contents. Famoxadone was a potent inhibitor of the growth of Saccharomyces cerevisiae when grown on non-fermentable carbon sources and it was an approximately 50-fold less potent inhibitor of growth when the yeast was grown on a fermentable carbon source, glucose. Such physiological observations are consistent with the loss of mitochondrial function imposed by famoxadone and OADs. Single amino acid changes in the apocytochrome b of baker's yeast cytochrome b located near the low potential heme altered the inhibition constants for the inhibitors famoxadone, myxothiazol, azoxystrobin and kresoxim-methyl differentially, thus strongly suggesting different binding interactions of the protein with the inhibitors. © 1999 Society of Chemical Industry     

噁唑菌酮在柑橘上的残留动态研究

采用乙腈提取、硅胶柱净化、HPLC的检测方法，研究了噁唑菌酮在柑橘中的残留动态。结果表明，方法的回收率为79．28％～101．47％，变异系数为3．27％～6．69％。噁唑菌酮在橘皮中的降解回归方程为Ct=0．5401e^-0.0751t，r=-0．9672。嗯唑菌酮在橘皮中半衰期为9．2d。初步提出了该药在柑橘上的安全使用标准。     

恶唑菌酮在苹果和土壤中的残留分析方法

研究并建立了恶唑菌酮(famoxadone)在苹果和土壤中的残留分析方法.样品以甲醇提取,固相萃取(SPE)净化,高效液相色谱(HPLC)测定.恶唑菌酮的最小检测量为4.0×10-9 g,苹果中的最低检出浓度为0.008 mg·kg-1,土壤为0.02 mg·kg-1.在0.05～5.0 mg·kg-1的添加浓度下,土壤中恶唑菌酮的平均添加回收率为81.45%～91.61%,变异系数为2.93%～6.52%;苹果中的平均添加回收率为84.06%～97.93%,变异系数为4.61%～6.67%.该方法的准确性、精确性以及灵敏度均达到农药残留分析的要求.     

Fate of famoxadone in the environment

The fate of famoxadone [Famoxate®, 3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione] in the aquatic and soil environment was examined. It was found to be relatively stable at pH 5, but hydrolysed rapidly in pH 7 and 9 buffer solutions. Primary hydrolytic degradation reactions included the opening of the oxazolidinedione ring and the cleavage of the oxazolidinedione-aminophenyl linkage. The compound degraded rapidly in soil by both hydrolytic and microbial action. In addition to the generation of [¹⁴C] carbon dioxide and unextractable bound residues, hydroxylation and hydrolysis reactions occurred to yield multiple degradation products. Nitration of famoxadone at the 2- or 4-phenylamino position was observed as a novel non-biological degradation reaction of famoxadone in soil. Degradation in aqueous solution (pH 5) and on soil surfaces was accelerated under simulated sunlight irradiation. Famoxadone exhibited negligible soil mobility potential, and its primary degradation products were also shown to dissipate rapidly in the environment.     

Behaviour of famoxadone deposits on grape leaves

Famoxadone is a new fungicide developed for the control of crop diseases, including grape downy mildew (Plasmopara viticola). The majority (>90%) of the spray deposit from a famoxadone 500 g kg⁻¹ water‐dispersible granule formation on a grape leaf were found on the leaf surface or associated with epicuticular waxes. A significant fraction of this deposit could not be removed by a water wash, suggesting strong binding to the waxes. Nearly 100% of the spray deposit was still recovered after 12 days of exposure to a dry environment, confirming the good residual properties of the substance. Thirty per cent of the applied active ingredient was lost after exposure to a wet environment, probably via hydrolysis or wash‐off. Studies with radiolabelled famoxadone formulated as a suspension concentrate indicated that redistribution occurred both in dry conditions, via diffusion in the cuticular waxes, and in wet conditions via dissolution in water followed by re‐deposition. No systemic movement of famoxadone was observed within the treated plant. Grape plants treated with famoxadone alone or in mixture with cymoxanil and subjected to up to 50 mm of artificial rain remained well protected against downy mildew infections. Good rain‐fastness was observed even 2 h after fungicide application. Despite low water solubility, famoxadone spray residues on grape leaves were reactivated in surface water sufficiently quickly to prevent infection by P viticola. © 2000 Society of Chemical Industry     

恶唑菌酮在土壤中的移动性研究

采用土壤薄层层析法研究了杀菌剂恶唑菌酮在土壤中的移动性以及表面活性剂对其移动性的影响。结果表明,在不同性质的土壤中恶唑菌酮的相对移动值Rf在0.089￣0.141之间。恶唑菌酮土壤中移动性的差异主要与土壤有机质和粘粒含量有关,它们之间呈显著的负相关性。通过供试的3种表面活性剂发现,表面活性剂影响恶唑菌酮的移动性主要取决于表面活性剂的临界胶束浓度,在低于表面活性剂临界胶束浓度中恶唑菌酮的移动性受到抑制,而在高于临界胶束浓度下恶唑菌酮的移动性明显增大。恶唑菌酮在表面活性剂中移动性的变化是恶唑菌酮和土壤表面吸附位、表面活性剂分子、胶束之间相互作用的结果。