Anilinopyrimidine Fungicides Research Articles

In vitro and In vivo Activity of Cyprodinil and Pyrimethanil on Botrytis cinerea Isolates Resistant to other Botryticides and Selection for Resistance to Pyrimethanil in a Greenhouse Population in Greece

No cross-resistance was observed between pyrimethanil or cyprodinil and the fungicides benomyl, iprodione or carbendazim + diethofencarb. In vitro, both anilinopyrimidine fungicides were effective against strains of Botrytis cinerea resistant to benzimidazoles and/or dicarboximides and against a wild type strain insensitive to diethofencarb (EC50 values ranged between 0.03–0.19 and 0.006–0.054 μg ml−1 for pyrimethanil and cyprodinil, respectively). Preventive applications of anilinopyrimidines completely protected young cucumber plants and fruits that were inoculated with all strains of B. cinerea. The effectiveness of pyrimethanil against grey mould was studied in greenhouse grown tomatoes in relation to (a) the type of infection and the progress of the disease on different plant parts and (b) the response of the naturally occurring B. cinerea population to the selection pressure caused by eight successive applications of this fungicide. Pyrimethanil effectively controlled grey mould on leaves, fruits and stems but did not significantly reduce the number of dead plants and fruits with 'ghost spot' symptoms. The selection pressure caused by the consecutive applications of pyrimethanil resulted in reduction of its effectiveness on leaves that became apparent after the sixth application. This was correlated with a shift of the B. cinerea population (not previously exposed to anilinopyrimidines) towards reduced sensitivity, probably due to the development of a low level of resistance (RL = 7.7). Pyrimethanil delayed the onset of the disease but it did not reduce the infection rate.

Occurrence of resistant strains of Botrytis cinerea to anilinopyrimidine fungicides in table grapes in Chile

Effort to control gray mold caused by Botrytis cinerea failed in a table grapevine ( Vitis vinifera) vineyard near Santiago, Chile where cyprodinil (Vangard 50 WP), a new fungicide of the anilinopyrimidine group, had been applied alone up to four times per year during two growing seasons. A relatively high frequency (38.5%) of resistant isolates of B. cinerea (EC 50 for mycelial growth inhibition varied from 2.9 to 4.84 μg ml −1) may explain the partial loss of field control efficacy obtained. Resistance was correlated with a complete loss of in vivo sensitivity to cyprodinil. Resistant isolates of B. cinerea showed cross resistance to the anilinopyrimidines fungicides mepanipyrim and pyrimethanil. Cyprodinil partially impaired conidia germination and differentially affected conidial germination of resistant and sensitive isolates. Significant differences ( p<0.05) in growth rate, sclerotia production and osmotic sensitivity were found among isolates of B. cinerea, but no correlation could be drawn between these biological differences and resistance or sensitivity. This indicates a disruptive selection characteristic of monogenic resistance. Thus, strategies were implemented to avoid the further development and spread of resistance in B. cinerea to the anilinopyrimidine fungicides. To our knowledge this constitutes the first mention of resistance in B. cinerea populations to anilinopyrimidine fungicides in South America.

Resistance risk assessment of cereal eyespot, Tapesia yallundae and Tapesia acuformis, to the anilinopyrimidine fungicide, cyprodinil.

Eyespot pathogens, Tapesia yallundae and Tapesia acuformis, were isolated from two trial sites in the UK over several years. Both sites were treated with 2 applications per year of cyprodinil (a new anilinopyrimidine fungicide), prochloraz and a mixture of cyprodinil with prochloraz. One trial site was exposed to cyprodinil for 3 years, and the second for a total of 11 years, including 5 years before the trial was initiated. Control of eyespot and sensitivity to cyprodinil were monitored. During the first 3 years of the trial, disease control with all fungicide treatments ranged from 43% to 82%. At the site, where the trial was extended for a further 3 years, control then began to decline but no practical resistance was detected. The decline in control by both fungicides suggests that factors other than reduced sensitivity might be involved. Field isolates of both T. yallundae and T. acuformis with reduced sensitivity to cyprodinil were found predominantly in plots treated with cyprodinil. A reduction in sensitivity to cyprodinil was identified in the population from cyprodinil-treated plots in two years out of six, and in the population from mixture plots in the final year. No obvious trends could be identified and in-vivo studies showed control of most isolates with reduced sensitivity could be regained by increasing the dose to one tenth of the recommended field rate. Analysis of progeny from sexual crosses involving a sensitive isolate and a field isolate with an ED50 value higher than the baseline sensitivity range indicated that a single gene controlled the reduction in sensitivity to cyprodinil in one T. yallundae isolate. There is clearly a resistance risk in eyespot to cyprodinil. The reduction in sensitivity is monogenic in inheritance and at a significant level in some isolates, but any shift in sensitivity in field populations has so far been gradual.

Influence of formulants and salt formation on volatilisation and activity of pyrimethanil

Pyrimethanil is an anilinopyrimidine fungicide which is highly effective against grey mould (Botrytis cinerea) in many crops. Some of its effectiveness can be attributed to localised vapour-phase activity in parts of the canopy not reached by foliar spray. Control of pyrimethanil volatilisation was investigated using matrix-forming materials or by formation of salts using organic acids. Whilst matrix formation had little effect, organic salts of pyrimethanil showed much reduced volatility. Some of the salts showed different bio-logical potential against cereal pathogens that were not well controlled by parent pyrimethanil. In addition, salt formation offered the possibility of significant changes to the physical form of pyrimethanil, opening up new formulation and co-formulation opportunities. © 1998 Society of Chemical Industry

Assessment of Sensitivities to Anilinopyrimidine‐ and Strobilurin‐fungicides in Populations of the Apple Scab Fungus Venturia inaequalis

AbstractThe sensitivity of Venturia inaequalis populations to the anilinopyrimidine fungicides pyrimethanil and cyprodinil was analysed by microscopic in vivo analysis of conidiophore formation. The sensitivity to the strobilurin kresoxim‐methyl was analysed using an in vitro germination assay and by determination of the diseased leaf area and conidia produced in vivo. Baseline sensitivities were determined with V. inaequalis populations from control orchards that had never been treated with fungicides. Comparison of the baseline sensitivities with sensitivities of populations obtained from orchards that had received 43 anilinopyrimidine treatments over 4 years, or from an orchard with 54 kresoxim‐methyl treatments over 6 years indicated that no resistance to these fungicides has developed at the sites sampled.

Genetic Basis and Monitoring of Resistance of Botryotinia fuckeliana to Anilinopyrimidines.

The anilinopyrimidines constitute a new class of mainly protective, broad-spectrum fungicides with a high activity against Botryotinia fuckeliana, the causal agent of gray mold on a wide range of host plants. The present study was initiated to investigate the genetic basis of resistance to anilinopyrimidines in B. fuckeliana and to assess the frequency of resistant isolates in vineyards in Switzerland exposed to experimental applications of anilinopyrimidines. In mating experiments, two sensitive reference isolates were crossed with three anilinopyrimidine-resistant field isolates. The analysis of 72 sexual progeny from six apothecia demonstrated that resistance to the anilinopyrimidine fungicide cyprodinil segregated in a 1:1 ratio and is therefore monogenic. The same segregation ratio was found for resistance to the dicarboximide fungicide vinclozolin. Resistance to cyprodinil segregated independently from resistance to vinclozolin. From 1993 to 1995, isolates of B. fuckeliana were collected in Switzerland from five vineyards that differed in their anilinopyrimidine spray history. Of a total of 303 isolates tested in vitro, three anilinopyrimidine-resistant isolates were detected in two vineyards where the cumulative number of treatments was between two and nine. The results of the study are discussed with respect to the implementation of an antiresistance strategy in Switzerland.

Inhibition of Methionine Biosynthesis inBotrytis cinereaby the Anilinopyrimidine Fungicide Pyrimethanil

When mycelium of Botrytis cinerea was treated with low concentrations of the anilinopyrimidine fungicide pyrimethanil the total amount of free amino acids increased. Qualitative variations were also induced: alanine, glutamine, lysine, glycine, histidine, asparagine, arginine, threonine and moreover, α-aminobutyrate and β-alanine were accumulated; cyst(e)ine, valine, leucine and citrulline were reduced. When mycelium of B. cinerea was incubated with Na2[35S]O4, pyrimethanil at 1·5 μM induced a decrease of [35S]methionine and simultaneously an increase of [35S]cystathionine. These data indicate that the anilinopyrimidine fungicide pyrimethanil inhibits the biosynthesis of methionine and suggest that the primary target could be the cystathionine β-lyase. © 1997 SCI.

A Reliable Method for Testing the Sensitivity ofBotryotinia fuckelianato AnilinopyrimidinesIn Vitro

Cyprodinil is a representative of the new class of broad-spectrum anilinopyrimidine fungicides. The effect of cyprodinil on mycelial growth of Botryotinia fuckeliana on solid agar medium depends on the composition of the medium and on the age of the mycelium to be used for the bioassay. An in-vitro method was developed to study the sensitivity distribution to cyprodinil in two wild-type populations of B. fuckeliana from fruits of strawberry with grey mould. To validate the applicability of the method, sensitivities to cyprodinil, mepanipyrim and pyrimethanil were monitored in populations of B. fuckeliana from grapes with grey mould from different vineyards, including one trial vineyard where reduced performance of cyprodinil had been encountered. The monitoring procedure was based on the inhibition of the mycelial growth on a synthetic medium containing L-asparagine (asp-agar) amended with the active ingredients. The mycelium was grown on asp-agar discs, starting from a spore suspension, for 17 h prior to the beginning of the test. This procedure proved to be efficient. The two wild-type populations from different sampling sites showed similar distributions of the sensitivity to cyprodinil. Some isolates from the trial site with reduced performance of anilinopyrimidines showed reduced sensitivities to cyprodinil, mepanipyrim and pyrimethanil, demonstrating cross-resistance between these anilinopyrimidines.

FRAC METHODS FOR MONITORING THE SENSITIVITY OF BOTRYTIS CINEREA TO ANILINO PYRIMIDINE FUNGICIDES

Methods are presented for monitoring the sensitivity to anilinopyrimidine fungicides of Botrytis cinerea. The methods are intended for practical usc in thc implementation of antiresistance strategies. Methods for other groups of fungicides have already been published in Bulletin OEPP/EPPO Bulletin21, 291‐354 and 22, 297‐322.