Resistance to succinate dehydrogenase inhibitors in field isolates of Podosphaera xanthii on cucumber: Monitoring, cross-resistance patterns and molecular characterization

Miyamoto, Takuya; Hayashi, Kengo; Okada, Ryo; Wari, David; Ogawara, Takashi

doi:10.1016/j.pestbp.2020.104646

Cited by 20 publications

(16 citation statements)

References 35 publications

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“…Another Japanese study also performed showed cross-resistance to boscalid and penthiopyrad but not to fluopyram [ 160 ]. Recently, 127 Japanese isolates were tested to check their sensitivity to the commercial fungicides isofematid, isopyrazam, penthiopyrad and pyraziflumid [ 161 ]. The results showed that 42.5% of the isolates had moderate levels of resistance to penthiopyrad (EC 50 = 335.1 – 787.6 mg/L), isopyrazam (EC 50 = 77.4–266.5 mg/L) and pyraziflumid (EC 50 = 9.2–31.2 mg/L); 44% of the isolates had high levels of resistance to penthiopyrad (EC 50 > 1000 mg/L), isopyrazam (EC 50 > 1070 mg/L) and pyraziflumid (EC 50 > 1000 mg/L); finally, only 1.5% showed high levels of resistance to isofatamid (EC 50 > 2400 mg/L) [ 161 ].…”

Section: Current Fungicide Resistance Status In Powdery Mildew Funmentioning

confidence: 99%

“…Recently, 127 Japanese isolates were tested to check their sensitivity to the commercial fungicides isofematid, isopyrazam, penthiopyrad and pyraziflumid [ 161 ]. The results showed that 42.5% of the isolates had moderate levels of resistance to penthiopyrad (EC 50 = 335.1 – 787.6 mg/L), isopyrazam (EC 50 = 77.4–266.5 mg/L) and pyraziflumid (EC 50 = 9.2–31.2 mg/L); 44% of the isolates had high levels of resistance to penthiopyrad (EC 50 > 1000 mg/L), isopyrazam (EC 50 > 1070 mg/L) and pyraziflumid (EC 50 > 1000 mg/L); finally, only 1.5% showed high levels of resistance to isofatamid (EC 50 > 2400 mg/L) [ 161 ]. With respect to the grape powdery mildew, boscalid provided good control of E. necator until 2014, when a report described boscalid-resistant isolates collected from French vineyards that were able to grow at 30 and 100 mg/L of the formulated product [ 162 ] ( Table 2 ).…”

Section: Current Fungicide Resistance Status In Powdery Mildew Funmentioning

confidence: 99%

“…Few studies have been performed to clarify the molecular mechanism of resistance to SDHIs in powdery mildews, and only two reports have analysed the different SDH subunits to determine amino acid changes in the grape powdery mildew ( Table 3 ). In P. xanthii , mutations in the SdhC and SdhD subunits were correlated with different levels of resistance to SDHIs [ 161 ]. Japanese isolates with moderate levels of resistance to penthiopyrad, isopyrazam and pyraziflumid presented the amino acid change S121P in the SdhD subunit; however, the amino acid changes G151R and G172D in the SdhC subunit and H137R in the SdhD subunit were correlated with high levels of resistance to the same fungicides.…”

Section: Current Fungicide Resistance Status In Powdery Mildew Funmentioning

confidence: 99%

“…Japanese isolates with moderate levels of resistance to penthiopyrad, isopyrazam and pyraziflumid presented the amino acid change S121P in the SdhD subunit; however, the amino acid changes G151R and G172D in the SdhC subunit and H137R in the SdhD subunit were correlated with high levels of resistance to the same fungicides. An additional mutation (A86V) in the subunit C was also correlated with high levels of resistance to isofetamid [ 161 ]. In E. necator , the amino acid changes H242R and H242Y in the SdhB subunit were correlated with resistance to boscalid [ 165 ] and with moderate levels of resistance to fluopyram and fluxapyroxad [ 162 ].…”

Section: Current Fungicide Resistance Status In Powdery Mildew Funmentioning

confidence: 99%

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Fungicide Resistance in Powdery Mildew Fungi

et al. 2020

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Powdery mildew fungi (Erysiphales) are among the most common and important plant fungal pathogens. These fungi are obligate biotrophic parasites that attack nearly 10,000 species of angiosperms, including major crops, such as cereals and grapes. Although cultural and biological practices may reduce the risk of infection by powdery mildew, they do not provide sufficient protection. Therefore, in practice, chemical control, including the use of fungicides from multiple chemical groups, is the most effective tool for managing powdery mildew. Unfortunately, the risk of resistance development is high because typical spray programs include multiple applications per season. In addition, some of the most economically destructive species of powdery mildew fungi are considered to be high-risk pathogens and are able to develop resistance to several chemical classes within a few years. This situation has decreased the efficacy of the major fungicide classes, such as sterol demethylation inhibitors, quinone outside inhibitors and succinate dehydrogenase inhibitors, that are employed against powdery mildews. In this review, we present cases of reduction in sensitivity, development of resistance and failure of control by fungicides that have been or are being used to manage powdery mildew. In addition, the molecular mechanisms underlying resistance to fungicides are also outlined. Finally, a number of recommendations are provided to decrease the probability of resistance development when fungicides are employed.

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Section: Current Fungicide Resistance Status In Powdery Mildew Funmentioning

confidence: 99%

Section: Current Fungicide Resistance Status In Powdery Mildew Funmentioning

confidence: 99%

Section: Current Fungicide Resistance Status In Powdery Mildew Funmentioning

confidence: 99%

Section: Current Fungicide Resistance Status In Powdery Mildew Funmentioning

confidence: 99%

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Fungicide Resistance in Powdery Mildew Fungi

et al. 2020

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“…Launched in 2012, the novel SDHI fungicide fluopyram, with the distinct structure of an extension on a bridged chain, provides a different binding mode compared to previous SDHI products 11,23‐26 . No cross‐resistance has appeared between these fungicides and fluopyram, or for another SDHI fungicide, isofetamid, with novel a bridge 27,28 . Therefore, modification on the bridged chain may lead to a novel binding mode and further slow resistance development.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and antifungal/anti‐oomycete activity of pyrazolyl oxime ethers as novel potential succinate dehydrogenase inhibitors

Wang

Chen

et al. 2021

Pest Management Science

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BACKGROUND Succinate dehydrogenase inhibitors (SDHIs) play an increasingly important role in controlling plant diseases. However, the similar structures of SDHIs result in rapid development of cross‐resistance development and a clear bottleneck of poor activity against oomycetes, therefore the need to seek new SDHI fungicides with novel structures is urgent. RESULTS Innovative pyrazolyl oxime ethers were designed by replacing amide with oxime ether based on the succinate dehydrogenase (SDH) structure, and 19 pairs of Z‐ and E‐isomers were efficiently prepared for the discovery of SDHI compounds with a novel bridge. Their biological activities against four fungi and two oomycetes were evaluated, and substantial differences were observed between the Z‐ and E‐ isomers of the title compounds. Furthermore, most of these compounds exhibited remarkable activities against Rhizoctonia solani with EC50 values of less than 10 mg L−1 in vitro, and bioassay in vivo further confirmed that E‐I‐6 exhibited good protective efficacy (76.12%) at 200 mg L−1. In addition, Z‐I‐12 provided better activity against the oomycetes Pythium aphanidermatum and Phytophthora capsici (EC50 = 1.56 and 0.93 mg L−1) than those of boscalid. Moreover, E‐I‐12 exhibited excellent SDH inhibition (IC50 = 0.21 mg L−1) thanks to its good binding ability to the SDH by hydrogen‐bonding interactions, π‐cation interaction and hydrophobic interactions. CONCLUSION Novel pyrazolyl oxime ethers have the potential as SDHI compounds for future development, and the strategy of replacing an amide bond with oxime ether may offer an alternative option in SDHI fungicide discovery.

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Novel quinolin‐2(1H)‐one analogues as potential fungicides targeting succinate dehydrogenase: design, synthesis, inhibitory evaluation and molecular modeling

Wang

Xiao

et al. 2023

Pest Management Science

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BACKGROUNDSuccinate dehydrogenase is an important target of fungicides. Succinate dehydrogenase inhibitors (SDHIs) have widely been used to combat destructive plant pathogenic fungi because they possess efficient and broad‐spectrum antifungal activities and as well as unique mode of action. The research and development of novel SDHIs have been ongoing.RESULTSThirty‐six novel quinolin‐2(1H)‐one derivatives were designed, synthesized and characterized. The single crystal structure of compound 3c was determined through the X‐ray diffraction of single crystals. The bioassay results displayed that most compounds had good antifungal activities at 16 μg mL−1 against Rhizoctonia cerealis, Erysiphe graminis, Botrytis cinerea, Penicillium italicum and Phytophthora infestans. Compounds 6o, 6p and 6r had better antifungal activities than the commercialized fungicide pyraziflumid against Botrytis cinerea. Their half maximal effective concentration (EC50) values were 0.398, 0.513, 0.205 and 0.706 μg mL−1, respectively. Moreover, the inhibiting activities of the bioactive compounds were tested against succinate dehydrogenase. The results indicated that they possessed outstanding activities. Compounds 6o, 6p and 6r also exhibited better inhibiting activities than pyraziflumid against succinate dehydrogenase. Their half maximal inhibitory concentration (IC50) values were 0.450, 0.672, 0.232 and 0.858 μg mL−1, respectively. The results of molecular dynamic (MD) simulations indicated that compound 6r displayed stronger affinity to succinate dehydrogenase than pyraziflumid.CONCLUSIONThe results of the present study displayed that quinolin‐2(1H)‐one derivative could be one scaffold of potential SDHIs and will provide some valuable information for the research and development of new SDHIs. © 2022 Society of Chemical Industry.

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Resistance to succinate dehydrogenase inhibitors in field isolates of Podosphaera xanthii on cucumber: Monitoring, cross-resistance patterns and molecular characterization

Cited by 20 publications

References 35 publications

Fungicide Resistance in Powdery Mildew Fungi

Fungicide Resistance in Powdery Mildew Fungi

Design, synthesis and antifungal/anti‐oomycete activity of pyrazolyl oxime ethers as novel potential succinate dehydrogenase inhibitors

Novel quinolin‐2(1H)‐one analogues as potential fungicides targeting succinate dehydrogenase: design, synthesis, inhibitory evaluation and molecular modeling

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