Antifungal modes of action of metalaxyl, cyprofuram, benalaxyl and oxadixyl in phenylamide-sensitive and phenylamide-resistant strains of Phytophthora megasperma f. sp. medicaginis and Phytophthora infestans

Davidse, L.C.; Gerritsma, O.C.M.; Ideler, Joy; Pie, K.; Velthuis, Grardy C.M.

doi:10.1016/0261-2194(88)90001-4

Cited by 35 publications

(23 citation statements)

References 14 publications

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“…Metalaxyl is a systemic fungicide belonging to the group of phenylamide fungicides, with excellent efficacy against a wide range of oomycetes. Phenylamides are inhibitors of ribosomal RNA polymerase in the target oomycete (Davidse et al ., 1988) and resistance is determined monogenically (Shattock, 2002). Thus, the efficacy of phenylamides is vulnerable.…”

Section: Introductionmentioning

confidence: 99%

Phenotypic and genetic variation in Finnish potato‐late blight populations, 1997–2000

Lehtinen

Hannukkala

Rantanen³

et al. 2006

Plant Pathology

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This study was conducted on potato late blight samples collected for monitoring early attacks in Finland from 1997 to 2000. Most of the 1726 Phytophthora infestans isolates were collected soon after the onset of the epidemics. Most of the isolates were tested for mating type as well as metalaxyl and propamocarb hydrochloride (HCl) sensitivity, while virulence on potato R-gene differentials and mitochondrial DNA (mtDNA) haplotype were determined for a subset of the isolates. In half of the fields from which more than one isolate was tested, both mating types were detected, indicating strong potential for sexual reproduction. The mating types coexisted more often in organic fields or gardens than in conventional fields. The proportion of A1 mating type decreased from approximately 80% (1997 and 1998) to 22% by the year 2000. Simultaneously, the proportion of isolates resistant to metalaxyl decreased from approximately 40% to 16%. Resistance to metalaxyl was confined to the IIa mtDNA haplotype and clearly associated with the A1 mating type, as resistance was 10 times more common among A1 isolates than among A2 isolates. Resistance to metalaxyl therefore probably derives from common descent from an isolate with the IIa haplotype. Most of the regional variation in metalaxyl sensitivity was also linked to mating type, as both metalaxyl resistance and the A1 mating type were most common in the north and south-west of Finland. In contrast to metalaxyl, only three propamocarb-HCl-insensitive isolates were found, but propamocarb-HCl sensitivity decreased significantly during the study.

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Section: Introductionmentioning

confidence: 99%

Phenotypic and genetic variation in Finnish potato‐late blight populations, 1997–2000

Lehtinen

Hannukkala

Rantanen³

et al. 2006

Plant Pathology

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“…and other Oomycetes. [1,2] The two fungicides can be absorbed by the roots, stalks and leaves, and move to all parts of the plant to protect against downy mildews, late blight, damping off, and root, stem and fruit rots. [3,4] Although the fungicidal activity of benalaxyl and furalaxyl are mainly attributed to their Renantiomer, [5,6] both of them are presently marketed in racemic formulations.…”

Section: Introductionmentioning

confidence: 99%

Environmental behavior of benalaxyl and furalaxyl enantiomers in agricultural soils

Fang

Gao

Guo

et al. 2014

Journal of Environmental Science and Health, Part B

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The enantioselective environmental behavior of the chiral fungicides benalaxy and furalaxyl in agricultural soils in China was studied. Although sorption onto soils was non-enantioselective, the leaching of benalaxy and furalaxyl was enantioselective in soil columns. The concentrations of the S-enantiomers of both fungicides in the leachates were higher than the R-enantiomers. This can be attributed to enantioselective degradation of the two fungicides in the soil column. Enantioselective degradation of the two fungicides was verified by soil dissipation experiments, and the R-enantiomers degraded faster than the S-enantiomers in partial soils. The half-life was 27.7-57.8 days for S-benalaxyl, 20.4-53.3 days for R-benalaxyl, 19.3-49.5 days for S-furalaxyl and 11.4-34.7 days for R-furalaxyl. The degradation process of the two fungicide enantiomers followed the first-order kinetics (R 2 > 0.96). Compared to furalaxyl, benalaxyl degraded more slowly and degradation was less enantioselective. These results are attributed to the influence of soil physicochemical properties, soil microorganisms, and environmental factors.

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“…Furalaxyl, (R, S) ‐methyl‐N‐(2, 6‐dimethylphenyl)‐N‐(2‐furanylcarbonyl)‐DL‐alaninate (Figure ), has an asymmetrically substituted C atom and consists of a pair of enantiomers. It was first introduced in 1977 as acylanilide fungicides and is still widely used in the control of plant diseases caused by infection with Phytophthora sp ., Albugo candida , Pythium sp ., Peronospora parasitica , and Fusarium solani . It is mostly used against downy mildews, late blight, damping off, and root, stem and fruit rots in many agricultural crops, and primarily interferes with the ribosomal nucleic acid synthesis in oomycetes Although the fungicidal activity of furalaxyl is mainly attributed to its (R) ‐enantiomer, it is presently marketed in racemic formulations .…”

Section: Introductionmentioning

confidence: 99%

Enantioselective toxic effects and digestion of furalaxyl enantiomers in Scenedesmus obliquus

Cheng

et al. 2018

Chirality

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Research on the enantioselective environmental behavior of chiral pesticides has been a hot spot of environmental chemistry recently. In this study, the acute toxicity and digestion of furalaxyl enantiomers were determined on the aquatic algae Scendesmus obliquus. After exposure for 96 hours, the EC50 values for (S)‐furalaxyl and (R)‐furalaxyl were 13.59 and 15.26 mg/L, respectively. In addition, enantioselectivity was observed from the determined chlorophyll contents and antioxidant enzyme (CAT and SOD) activities of algae cells after exposure to furalaxyl enantiomers for 96 hours. The digestion rate of (S)‐furalaxyl and (R)‐furalaxyl were almost the same in S. obliquus. On the basis of these data, the inactive enantiomers (S)‐ furalaxyl is more toxic than the active one on the non‐target species S. obliquus, indicating that such enantiomeric differences should be taken into consideration in the study of pesticide risk assessment.

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Antifungal modes of action of metalaxyl, cyprofuram, benalaxyl and oxadixyl in phenylamide-sensitive and phenylamide-resistant strains of Phytophthora megasperma f. sp. medicaginis and Phytophthora infestans

Cited by 35 publications

References 14 publications

Phenotypic and genetic variation in Finnish potato‐late blight populations, 1997–2000

Phenotypic and genetic variation in Finnish potato‐late blight populations, 1997–2000

Environmental behavior of benalaxyl and furalaxyl enantiomers in agricultural soils

Enantioselective toxic effects and digestion of furalaxyl enantiomers in Scenedesmus obliquus

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