Reduced sensitivity to fenarimol in Japanese field strains of Venturia nashicola

Monoconidial strains of Venturia nashicola Tanaka et Yamamoto were isolated from Japanese or Chinese white pear trees which had never been treated with sterol demethylation inhibitors (DMIs) and their baseline sensitivities to fenarimol were determined by mycelial growth tests on fungicide-amended culture media. Strains were also obtained from Japanese pear orchards, which had been intensively treated with DMIs for several years and monitored for the shifts of fenarimol sensitivity in comparison with the baseline sensitivity. Results suggested slight shifts to lower fenarimol sensitivity in strains isolated from DMI-treated Japanese pear orchards. However, in inoculation tests on pear seedlings, fenarimol still provided adequate control of V. nashicola strains with reduced sensitivity to fenarimol in vitro, suggesting that the performance of this fungicide will still be maintained in the field. © 1998 Society of Chemical Industry     

Photodegradation of diafenthiuron in water

Diafenthiuron, 1-tert-butyl-3-(2,6-di-isopropyl-4-phenoxyphenyl)thiourea, is an effective insecticide and acaricide. Sunlight degradation of diafenthiuron in various aqueous solutions and pure hexane yielded two major identified products: 1-tert-butyl-3-(2,6-di-isopropyl-4-phenoxyphenyl)-carbodiimide (CGA-140,408) and 1-tert-butyl-3-(2,6-di-isopropyl-4-phenoxy-phenyl)urea (CGA-177,960). CGA-140,408 was further photo-transformed into CGA-177,960 by sunlight. Direct photolysis appeared to be a major photolysis pathway of diafenthiuron in the environment. Photodegradation of CGA-140,408 and CGA-177,960 was enhanced in humic acid water, paddy water and aqueous acetone solutions, and followed first-order kinetics. Isopropanol (a radical quencher) and de-aeration strongly inhibited the photolysis of these chemicals, which suggested oxygen radical-mediated reactions.     

Photodegradation of the carbamate insecticide ethiofencarb

In order to study the photoreactivity and possible photodegradation pathways of ethiofencarb (2-ethylthiomethylphenyl methylcarbamate) on plant surfaces, model experiments in the presence of cyclohexane, cyclohexene methylcarbamate)onand iso-propanol were performed. Both artificial light (λ > 280 nm) and natural sunlight were used. Half-lives of the ethiofencarb photodegradation were in the order cyclohexane < isopropanol < cyclohexene and ranged from 75 min to more than 20 h. Depending on the solvent and the light source chosen, different photo-products were obtained. When ethiofencarb was irradiated in the presence of cyclohexane, photo-oxidation to the corresponding sulfoxide was the main degradation pathway, followed by a cyclization reaction. In the case of isopropanol as model solvent, numerous photoproducts were detected as a result of photo-oxidation, hydrolysis and the addition to ethiofencarb of the solvent molecule.     

农药在水介质中的光化学降解研究情况

农药在水环境中会受到理化因子作用发生降解。本文通过对国内外关于水介质中农药光降解机理和影响因素的研究成果加以总结和归纳,阐述水介质中农药光降解的动力学模型、光化学反应类型,以及在水环境中影响农药光降解的主要因素,概述水介质中农药的光降解特性。     

Changes during a three-year period in the sensitivity to ergosterol biosynthesis inhibitors of Sphaerotheca fuliginea in the Netherlands

Isolates ofSphaerotheca fuliginea colleeted in 1981–1984 in cucumber giasshouses in the Netherlands were tested for their sensitivity to the ergosterol biosynthesis inhibitors (EBIs) fenarimol and imazalil.The data collected in the 1981 survey indicated that sensitivity to EBIs was lower than that of reference isolates. In the 1982 and 1983 surveys, sensitivity to EBIs continued to decrease. In 1984, data were collected until July; no significant difference in sensitivity with the 1983 level was apparent.Isolates collected in the district of Limburg, where EBIs were applied less frequently than in the district of Pijnacker, showed a significantly higher sensitivity to EBIs than isolates collected in Pijnacker.Besides differences in sensitivity to EBIs between years, differences within years were noticed. In 1983, the sensitivity to fenarimol and imazalil was significantly higher in the beginning of the growing season, before any fungicides were applied, than later in the growing season.Generally, changes in sensitivity to EBIs did not result in full failure of control. In most cases, a change to shorter spray intervals has been sufficient to compensate for the decrease in sensitivity and to achieve proper control by fenarimol and imazalil. The results once more emphasize the necessity of designing strategies to prevent resistance to EBIs.Samenvatting Uit komkommerkassen in Nederland werden gedurende de periode 1981–1984 isolaten vanSphaerotheca fuliginea verzameld. De gevoeligheid van deze isolaten voor fenarimol en imazalil, twee ergosterolbiosyntheseremmers (EBR's), werd getest. De gegevens verzameld in 1981 wijzen erop dat de gevoeligheid voor EBR's lager was dan die van referentie-isolaten. In 1982 en 1983 daalde de gevoeligheid voor EBR's nog verder. In 1984 werden gegevens verzameld tot en met juli. Er werd geen significant verschil in gevoeligheid waargenomen met het niveau van 1983.Isolaten verzameld in Limburg, waar EBR's minder vaak toegepast worden dan in Pijnacker, hadden een significant hogere gevoeligheid voor EBR's dan isolaten uit Pijnacker.Naast verschillen in gevoeligheid voor EBR's tussen jaren, werden ook verschillen binnen de jaren waargenomen. In het begin van het groeiseizoen in 1983, voordat fungiciden waren gebruikt, was de gevoeligheid voor fenarimol en imazalil hoger dan later in het groeiseizoen. In het algemeen hadden de veranderingen in gevoeligheid voor EBR's geen volledig falen van de bestrijding tot gevolg. In de meeste gevallen was een verkorting van de intervallen tussen de toepassingen van fenarimol en imazalil voldoende om te compenseren voor de verminderde gevoeligheid en om een goede bestrijding te verkrijgen. De resultaten benadrukken nogmaals de noodzaak om strategieën te ontwerpen die resistentie tegen EBR's voorkomen.     

不同光波长对水中乙草胺光分解的影响

以高压汞灯和太阳光为光源,以不同波长滤光片处理得相应波长区域,研究了乙草胺在水中的光解动态。结果表明:在胡敏酸存在下,乙草胺的光解动态符合一级动力学规律,其光解速度随着照射光波长的延长而减慢,光解半衰期延长,与未用滤光片处理的对照相比,差异极显著,表明乙草胺在水中的光解速度与照射光波长关系极大。     

Suppression of powdery mildew (Sphaerotheca fuliginea) in cucumber by the detergent Zohar LQ-215

The effect of the detergent Zohar LQ-215 alone or combined with the fungicide fenarimol (Rubigan) on cucumber powdery mildew (caused bySphaerotheca fuliginea) was examined under controlled environmental conditions and in the field. In laboratory tests conducted on leaf disks, the efficacy of fenarimol was 30 times greater than that of Zohar LQ-215 as indicated by the ED₅₀ values of the compounds (0.012% and 0.356%, respectively). Zohar LQ-215 did not reduce spore germination or germ-tube elongation, but inhibited the later stages of the disease cycle (i.e., mycelial growth and sporulation). Although the detergent was degraded relatively quickly, its effect on the polycyclic development of the disease lasted for up to 24 days after spraying. Low disease severity (2.4% compared with 27% in the control) was maintained following three applications of the detergent at 5 days intervals. In a greenhouse trial, a mixture of Zohar LQ-215 and fenarimol at half rate did not improve disease suppression beyond the effect of fenarimol applied alone at half rate. However, the effects of the two compounds were additive when applied in the field as a mixture.     

Characterisation of energy-dependent efflux of imazalil and fenarimol in isolates of Penicillium italicum with a low,medium and high degree of resistance to DMI-fungicides

Differential accumulation of [¹⁴C]imazalil and [¹⁴C]fenarimol by germlings of wild-type and DMI-resistant isolates ofPenicillium italicum was studied at various pH values. At pH 7 and 8 the low-resistant isolate E_300–3 accumulated 22% and 35%, respectively, less imazalil than the wild-type isolate W₅. Imazalil accumulation at pH 5 and 6 was similar. Isolate E_300–3 also accumulated less fenarimol as compared with the wild-type isolate. This difference was much more obvious than for imazalil and was observed at all pH values tested. Differences in accumulation of both imazalil and fenarimol between low (E_300–3), medium (H₁₇) and high resistant (I₃₃) isolates were not observed. These results suggest that decreased accumulation of DMIs is responsible for a low level of resistance only and that additional mechanisms of resistance might operate in isolates with a medium and high degree of resistance. With all isolates fenarimol accumulation was energy-dependent. This was not obvious for imazalil.The wild-type and DMI-resistant isolates had a similar plasma membrane potential as determined with the probe [¹⁴C]tetraphenylphosphonium bromide ([¹⁴C]TPP⁺). Various test compounds, among which ATPase inhibitors, ionophoric antibiotics and calmodulin antagonists, affected the accumulation of [¹⁴C]TPP⁺, [¹⁴C]imazalil and [¹⁴C]fenarimol. No obvious correlation between the effects of the test compounds on accumulation levels of the fungicides and [¹⁴C]TPP⁺ could be observed. These results indicate that the plasma membrane potential does not mediate the efflux of DMI fungicides byP. italicum.     

Fitness of isolates of Sphaerotheca fuliginea resistant or sensitive to fungicides which inhibit ergosterol biosynthesis

Isolates ofSphaerotheca fuliginea resistant to fungicides which inhibit ergosterol biosynthesis (EBIs: bitertanol, fenarimol, imazalil) had been collected from glasshouses in the Netherlands. Fitness of these isolates was compared to that of isolates with a wild-type sensitivity to EBIs. Fitness parameters studied were germination of conidia, growth of germ tubes and mycelium, penetration, sporulation and competitive ability.In an experiment in which 10 EBI-resistant isolates were compared to 7 wild-type isolates, one or more values of fitness parameters for EBI-resistant isolates were slightly lower than those for the wild-type isolates. However, within the group of resistant isolates no relation existed between the degree of resistance to EBIs and the degree of fitness. In an experiment with fewer isolates but with more replicates, differences in fitness between EBI-resistant and wild-type isolates were not detected over a three-month period.In competition experiments in which no crowding was present, resistant isolates competed well with the wild-type isolate.It is concluded that the hypothesis that resistance to EBIs is unlikely to develop under practical conditions because of decreased fitness of EBI-resistant strains, does not seem to hold forS. fuliginea.Samenvatting Uit kassen in Nederland waren isolaten vanSphaerotheca fuliginea verzameld, die resistent waren tegen fungiciden die de ergosterol-biosynthese remmen (EBR's: bitertanol, fenarimol, imazalil). De fitness van deze isolaten werd vergeleken met die van isolaten met een wild-type gevoeligheid voor EBR's. De volgende fitness-parameters werden bestudeerd: sporekieming, groei van kiembuizen en mycelium, penetratie, sporulatie en competitievermogen.In een proef, waarin 10 EBR-resistente isolaten werden vergeleken met 7 wild-type isolaten, waren één of meer fitness-parameters iets lager dan die van de wild-type isolaten. Binnen de groep van de resistente isolaten bestond geen relatie tussen de mate van resistentie tegen EBR's en de waarden van de fitness-parameters. In een proef met iets minder isolaten maar met meer herhalingen in de tijd, werden geen verschillen in fitness waargenomen tussen de EBR-resistente en wild-type isolaten. In competitieproeven waarin een epidemie zich kon ontwikkelen, concurreerden de resistente isolaten goed met het wild-type isolaat.Er wordt geconcludeerd dat de hypothese dat resistentie tegen EBR's in de praktijk waarschijnlijk niet zou optreden vanwege een verminderde fitness van de EBR-resistente isolaten, niet van toepassing is opS. fuliginea.     

Mechanism of resistance to fenarimol in Aspergillus nidulans

Mycelial uptake of [¹⁴C]fenarimol (10 μg/ml) by 20 fenarimol-resistant mutants of Aspergillus nidulans was compared with uptake by wild-type strain 003. Uptake of the fungicide during the initial 10 min of incubation was significantly lower in all mutant strains than in the wild-type strain indicating that resistance is related with reduced uptake. Upon prolonged incubation a gradual decrease of accumulated radioactivity in the wild-type strain was observed. A few mutants displayed resistance to unrelated chemicals such as p-fluorophenylalanine or d-serine; this phenomenon appeared not to be due to a decreased uptake of the corresponding natural amino acids. Incorporation of [³H]adenine and [¹⁴C]leucine by mycelium of mutant M193 was hardly inhibited after 5 hr of incubation with the fungicide, whereas a distinct effect was found with the wild-type strain. At this time also fungitoxicity to the wild-type strain became apparent. Probably, this effect is indirectly caused by inhibition of ergosterol biosynthesis. Mycelium of mutant M193 incorporated [¹⁴C]acetate slightly less effectively than the wild-type strain. After 2 hr of incubation with this radiochemical leakage of [¹⁴C]acetate metabolites from mycelium of the mutant strain was observed. This indicates that resistance might be correlated with increased excretion of fungal metabolites, which in turn may be related with reduced fitness of fenarimol-resistant mutants.     

Photodegradation of herbicide triasulfuron

Triasulfuron was degraded in aqueous solution by ultraviolet irradiation to yield 2-chloroethoxybenzene and (4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea. The reaction followed first-order kinetics. In sunlight, the reaction was slower and afforded these two photoproducts together with 2-amino-4-methoxy-6-methyltriazine and 2-(2-chloroethoxy)benzenesulfonamide. The latter compounds arise from hydrolytic cleavage of the sulfonylurea bridge of triasulfuron because of the acidity of the reaction medium due to the loss of sulfur dioxide. A mechanism which accounts for the formation of the photoproducts is proposed. © 1999 Society of Chemical Industry     

Baseline sensitivity and cross-resistance to demethylation-inhibiting fungicides in Ontario isolates of Sclerotinia homoeocarpa

Four hundred and thirty-five isolates of Sclerotinia homoeocarpa from eight populations in southern Ontario were tested for sensitivity to the demethylation-inhibiting (DMI) fungicides, propiconazole, myclobutanil, fenarimol and tebuconazole. The isolates were collected in summer 1994 just prior to legal DMI fungicide use on turfgrass in Ontario. There were wide variations in sensitivities, and seven of the eight populations were very sensitive to the fungicides. Based on mean EC₅₀ and the distribution of DMI sensitivity, one population near the U.S. border was suspected of having been previously exposed to DMI fungicide. Pairwise comparisons of EC₅₀ values for the different fungicides showed low to moderate correlations between fungicides. EC₅₀ values of myclobutanil and propiconazole had the best correlation, followed by the pair of tebuconazole and fenarimol. Other pairwise comparisons were not statistically significant except for a barely significant relationship between EC₅₀ values of myclobutanil and tebuconazole. For field populations of plant pathogens, cross-resistance to different DMI fungicides may not be as strong as conventionally thought. The data collected here will allow comparison to subsequent years to look for detectable shifts in S. homoeocarpa sensitivity to DMI fungicides as they become more frequently used in Ontario.     

Effects of phthalimide fungicides on the accumulation of fenarimol by Aspergillus nidulans

Phthalimide fungicides (captafol, captan and folpet) enhanced the accumulation of fenarimol by the mycelium of a wild-type strain and a fenarimol-resistant strain of Aspergillus nidulans. The accumulation is ascribed to inhibition of active efflux of fenarimol from the mycelium. It is assumed that the synergistic action observed between the phthalimide fungicides and fenarimol with respect to fungitoxicity, was caused by the increased accumulation of fenarimol.     

Stepwise development of laboratory resistance to DMI-fungicides in Penicillium italicum

Isolates ofPenicillium italicum with differential levels of resistance to imazalil were obtained via step-wise mass selection of conidia of the fenarimol-resistant isolate E300-3 on imazalilamended PDA. Three out of five selection steps were successful. The resistance level to imazalil of isolates acquired after the two last selection steps was on average 122 and 197. The differential level of resistance was also apparent in decay control on oranges by imazalil inoculated with the various isolates. The isolates showed a similar cross-resistance pattern to other fungicides which inhibit C-14 demethylation of sterols (DMIs), although the level of resistance to these fungicides was significantly higher. All isolates displayed negatively-correlated cross-resistance to tridemorph and dodine. Most isolates had a normal virulence on oranges. In competition experiments with mixed-inocula of the wild-type and a resistant isolate, the proportion of the wild-type increased in successive generations on untreated oranges and the proportion of the resistant isolate increased on imazalil-treated oranges. The lower competitive ability of the resistant isolate on untreated oranges may be due to a decrease in spore production as compared with the wild-type.Since isolate E300-3 was obtained in two selection steps on fenarimol-amended PDA, the isolates obtained in the last selection steps on imazalil-amended PDA may have at least five different genes for resistance to DMIs. This is consistent with resistance to DMIs being under polygenic control, with the genes involved having an additive interaction, although this is not the only possible explanation of the results.     

噁草酮在液相中的光化学降解研究

以高压汞灯为光源 ,研究了草酮在环己烷、甲醇、乙腈、丙酮及水溶液中的光化学降解。结果表明 :在环己烷、甲醇、乙腈、水中 ,草酮光降解效应显著 ,其半衰期分别为 4 .4 5、15 .34、5 7.5 8、5 4.6 9min;草酮在丙酮溶剂中降解缓慢 ,半衰期为 2 93.83min;丙酮对草酮在水中的光解有显著的光敏作用 ,光敏效应与丙酮的量显著相关 ,光敏效率最高达 95 .84 %。     

灰葡萄孢抗二甲酰亚胺类杀菌剂研究进展

综述了灰葡萄孢对二甲酰亚胺类杀菌剂抗性的产生及现状,抗性菌株的生物学特性、生理生化特性以及抗药性机制,并就灰葡萄孢对二甲酰亚胺类杀菌剂抗性研究进行了展望。     

Photodegradation of bensulfuron-methyl on soil surface

Photolysis of bensulfuron-methyl on soil surface was studied under sunlight and UV light. Seven photoproducts were isolated and characterised by spectroscopic methods. The major processes in the photolysis of bensulfuron-methyl in soil are cleavage of the sulfonylurea bridge, scission of the SO2NH bond and contraction of the sulfuronylurea bridge. The rates of photodegradation of bensulfuron-methyl on different soils followed first-order rate kinetics with half lives of 21.9, 28.4, 36.9, 59.2 and 47.2 h (UV) and 23.1, 27.5, 29.1, 38.9 and 33.8 days (sunlight) for vertisol, alluvial, alfisol, red and laterite soils, respectively. The differences in rates of photodegradation were dependent upon the soil texture and organic matter content.     

乙草胺在水中的光化学降解

以高压汞灯、氙灯、自然光为光源 ,研究了乙草胺在不同类型水中的光解动态。结果表明 :乙草胺的光量子产率低 ;高压汞灯光照下 ,乙草胺在水中的光解速度为纯水 >河水 >塘水 >稻田水 ,其光解率与水介质的 pH呈正相关 ;不同光源照射下 ,乙草胺于纯水中的光解速率有显著的差异 ,表现为高压汞灯 >氙灯 >自然光 ,同时其光解产物也存在明显的不同。     

山东蓬莱葡萄灰霉菌对7种杀菌剂的抗药性检测

为了明确葡萄灰霉菌对啶酰菌胺、多菌灵、咯菌腈、异菌脲、腐霉利、嘧霉胺的抗药性和对抑霉唑的敏感性,本试验采用菌丝生长速率法和孢子萌发法检测了采自山东蓬莱地区的69株葡萄灰霉菌对上述前6种杀菌剂的抗药性、对抑霉唑的敏感性及抑霉唑与其他6种杀菌剂的交互抗性关系。结果表明,抑霉唑对这69株葡萄灰霉菌的EC₅₀分布在0.403～28.76μg/mL之间,平均值为(9.34±10.34)μg/mL;葡萄灰霉菌菌株中抗啶酰菌胺(BosR)、多菌灵(CarR)、咯菌腈(FluR)、异菌脲(IprR)、嘧霉胺(PyrR)、腐霉利(ProR)的比例分别为100%、100%、9.47%、97.18%、100%、89.20%,测试菌株的抗药性均为多抗类型,没有单抗菌株,其中对3种杀菌剂(啶酰菌胺、多菌灵、嘧霉胺)、对4种杀菌剂(啶酰菌胺、多菌灵、异菌脲、嘧霉胺)、对5种杀菌剂(啶酰菌胺、多菌灵、异菌脲、嘧霉胺、腐霉利或啶酰菌胺、多菌灵、咯菌腈、异菌脲、嘧霉胺)和对6种杀菌剂(啶酰菌胺、多菌灵、咯菌腈、异菌脲、嘧霉胺、腐霉利)的抗性频率分别为2.33%、9.30%、79.07%、2.33%、6.97%,表明啶酰菌胺、多菌灵、嘧霉胺对测试葡萄菌株完全丧失防效,建议在该葡萄产区停止使用这些药剂,测试菌株对腐霉利、异菌脲的抗性频率高,建议采取限制使用、禁止单独使用等措施,测试菌株对咯菌腈的抗性频率较低,可以继续使用但需按照科学使用规则进行。抑霉唑与其他6种杀菌剂间不存在交互抗性关系,说明其可以和其他药剂同时使用但建议减少使用。