Activity and Resistance-Related Point Mutations in Target Protein PcORP1 of Fluoxapiprolin in <i>Phytophthora capsici</i>

Miao, Jianqiang; Li, Chengcheng; Liu, Xiaofei; Zhang, Xitao; Li, Guixiang; Wang, Xu; Zhang, Can; Liu, Xili

doi:10.1021/acs.jafc.0c05119

Cited by 19 publications

(30 citation statements)

References 27 publications

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“…According to our previous research, multiple mutations (G700V, ΔN765, N765S+I807F, N767I, and N767T+S840C) of ORP1 can be obtained in fluoxapiprolin-resistant P. capsici mutants. 16 Four types of mutations (S768I+N837I, S768I +L860I, S768I, and I877F) were found in PiORP1 from seven fluoxapiprolin-resistant mutants in the current study. Mutants containing S768I+N837I showed high resistance to fluoxapiprolin (RF > 1000), mutants containing S768I+L860I and I877F displayed high resistance (100 < RF < 1000), and mutants containing S768I displayed low resistance (RFs < 50).…”

Section: ■ Discussionsupporting

confidence: 44%

“…Thus, its resistance management strategies in control of P. infestans should also be established in advance, according to the recommendation of FRAC to OSBPIs. 16 Specific recommendations are as follows: apply OSBPIs at effective rates and intervals according to manufacturers' recommendations; apply OSBPIs preventatively and in mixtures with antioomycete inhibitors from different cross-resistance groups, such as CAAs; apply OSBPI products no more than two times per season in the potato continuous cropping area (https://www.frac.info/); use multiple control measures simultaneously, such as resistant varieties, agricultural control, and biological control. According to our previous research, multiple mutations (G700V, ΔN765, N765S+I807F, N767I, and N767T+S840C) of ORP1 can be obtained in fluoxapiprolin-resistant P. capsici mutants.…”

Section: ■ Discussionmentioning

confidence: 99%

“…13−15 Fluoxapiprolin is another OSBPI fungicide synthesized by Bayer Crop Science in 2012. 16 Its chemical structure is very similar to that of oxathiapiprolin. However, fluoxapiprolin is a racemate, and its R-enantiomer and S-enantiomer showed almost the same level of inhibitory activity to plant pathogenic oomycetes (http://www.agroinfo.com.cn/other_detail_6006.…”

Section: ■ Introductionmentioning

confidence: 89%

“…The half maximal effective concentration (EC 50 ) value of fluoxapiprolin against P. capsici is also about 10 −4 μg/mL, and it had been confirmed that the resistance mechanism of P. capsici to fluoxapiprolin overlaps with that of oxathiapiprolin. 16 However, the resistance risk and resistance mechanism of fluoxapiprolin in P. infestans have not been reported. Therefore, the objectives of this study were to (i) investigate the sensitivity of P. infestans to fluoxapiprolin; (ii) assess the resistance risk of fluoxapiprolin; and (iii) explore the fluoxapiprolin-resistant mechanism in P. infestans.…”

Section: ■ Introductionmentioning

confidence: 99%

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Resistance Risk and Novel Resistance-Related Point Mutations in Target Protein PiORP1 of Fluoxapiprolin in Phytophthora infestans

Liu

et al. 2022

J. Agric. Food Chem.

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Fluoxapiprolin is a new oxysterol binding protein inhibitor (OSBPI), which showed excellent inhibitory activity to plant pathogenic oomycetes. Its resistance risk and mechanism in Phytophthora infestans are unclear. In the current study, the sensitivities of 103 P. infestans isolates to fluoxapiprolin were investigated, and a unimodal distribution with a mean EC 50 value of 0.00035 μg/mL was observed. Four types of resistant mutants, with a resistance factor from 14 to more than 1000, and point mutations S768I+N837I, S768I+L860I, S768I, and I877F in PiORP1, were acquired using fungicide adaption. The fitness of the mutants was similar to or lower than that of the corresponding parental isolate. Positive cross-resistance was detected between fluoxapiprolin and oxathiapiprolin. The point mutations were verified in P. sojae homologue positions using the CRISPR/Cas9 genome editing system. Transformants containing S768I+N837I or S768I+L860I, showed high fluoxapiprolin resistance (RF > 1000). In conclusion, the risk of P. infestans resistance to fluoxapiprolin is moderate, and novel point mutation types S768I+N837I or S768I+L860I could cause high fluoxapiprolin resistance in P. infestans.

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Section: ■ Discussionsupporting

confidence: 44%

Section: ■ Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 89%

Section: ■ Introductionmentioning

confidence: 99%

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Resistance Risk and Novel Resistance-Related Point Mutations in Target Protein PiORP1 of Fluoxapiprolin in Phytophthora infestans

Liu

et al. 2022

J. Agric. Food Chem.

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“…Recently introduced fungicides include oxathiapiprolin (2017), oxathiapiprolin+ famoxadone (2018), oxathiapiprolin+ amisulbrom (2018), benthiavalicarb (2018), oxathiapiprolin + benthiavalicarb (2019) and fluoxapiprolin (2020). Oxathiapiprolin and fluoxapiprolin are piperidinyl thiazole isoxazoline fungicides (FRAC code 49, previously U15) that target the oxysterol binding proteins in oomycete cells [2][3][4]. Oxathiapiprolin is extremely active against plant pathogenic oomycetes except Pythium (see literature cited by [5]).…”

Section: Introductionmentioning

confidence: 99%

Effective control of two genotypes of Phytophthora infestans in the field by three oxathiapiprolin fungicidal mixtures

2021

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In two field experiments, performed in 2020 and 2021, potato Nicola plants were sprayed once with three (Exp. 1) or two (Exp. 2) doses of Zorvec Vinabel (oxathiapiprolin+ zoxamide = ZZ), Zorvec Encantia (oxathiapiprolin+ famoxadone = ZF), Zorvec Endavia (oxathiapiprolin+ benthiavalicarb = ZE), Infinito (= INF) or Mefenoxam (= MFX) and thereafter inoculated with genotype 23A1 or 36A2 of Phytophthora infestans. Disease development was recorded at periodic intervals for a month. In both experiments, Zorvec mixtures were significantly more effective in suppressing the disease than INF or MFX. They delayed the onset of the disease and its progress, regardless the genotype used for inoculation. Among the three Zorvec mixtures, ZZ was least effective and ZE most effective. Sensitivity monitoring assays revealed zero mutants of P. infestans resistant to oxathiapiprolin. The data confirmed good efficacy of Zorvec mixtures, especially ZE, in field-grown potato crops as evident by the very effective control of late blight for one month.

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Synthesis, Anti‐Oomycete and Anti‐fungal Activities of Novel Cinchona Alkaloid Derivatives Containing Sulfonate Moiety

Che

Chen

Zhang

et al. 2023

Chemistry & Biodiversity

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Using cinchona alkaloid as the lead compound, twenty-four cinchona alkaloid sulfonate derivatives (1 a-l, 2 a-c, 3 a-c, 4 ac, and 5 a-c) were designed and prepared by modifying their C9 position, and structurally confirmed by 1 H-NMR, 13 C-NMR, HR-MS and melting points. Moreover, the stereochemical configurations of compounds 1 f and 1 l were unambiguously confirmed by single-crystal X-ray diffraction. Furthermore, we determined the anti-oomycete and anti-fungal activities of these target compounds against Phytophthora capsici and Fusarium graminearum in vitro. The results showed that two compounds 4 b and 4 c exhibited prominent anti-oomycete activity, and the median effective concentration (EC 50 ) values of 4 b and 4 c against P. capsici were 22.55 and 16.32 mg/L, respectively. This study suggested that when the C9 position of cinchona alkaloid sulfonate derivatives is in the S configuration and the 6'-position methoxy group is not present, the anti-oomycete activity is superior. In addition, five compounds 1 e, 1 f, 1 k, 3 c and 4 c displayed significant anti-fungal activity, with EC 50 values of 43.64, 45.07, 80.18, 48.58 and 41.88 mg/L against F. graminearum, respectively. This result indicates that only when a specific substituent is introduced into the structural framework of the target compound, the corresponding compound exhibits significant inhibitory activity against fungi.

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Activity and Resistance-Related Point Mutations in Target Protein PcORP1 of Fluoxapiprolin in Phytophthora capsici

Cited by 19 publications

References 27 publications

Resistance Risk and Novel Resistance-Related Point Mutations in Target Protein PiORP1 of Fluoxapiprolin in Phytophthora infestans

Resistance Risk and Novel Resistance-Related Point Mutations in Target Protein PiORP1 of Fluoxapiprolin in Phytophthora infestans

Effective control of two genotypes of Phytophthora infestans in the field by three oxathiapiprolin fungicidal mixtures

Synthesis, Anti‐Oomycete and Anti‐fungal Activities of Novel Cinchona Alkaloid Derivatives Containing Sulfonate Moiety

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