Carboxylic Acid Amide (CAA) Fungicides

Gisi, U.; Lamberth, Clemens; Mehl, Andreas; Seitz, Tobias

doi:10.1002/9783527619580.ch18

Cited by 10 publications

(6 citation statements)

References 37 publications

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“…Thus, many conventional fungicides that are effective against true fungi are ineffective against oomycete diseases, such as sterol demethylation inhibitor fungicides, methyl benzimidazole carbamate fungicides and succinate dehydrogenase inhibitor fungicides (Gisi & Sierotzki, 2015). The carboxylic acid amide (CAA) fungicides, comprising the three subclasses of cinnamic acid amides (dimethomorph, flumorph and pyrimorph), valinamide carbamates (iprovalicarb and benthiavalicarb), and mandelic acid amides (mandipropamid), have shown specific activity against most oomycete pathogens, such as Phytophthora species, Plasmopara viticola, Bremia lactucae and Pseudoperonospora cubensis (Gisi et al, 2012). Despite differences in the chemical structures of the three subclasses, cross-resistance exists among all group members in the vast majority of the tested oomycete isolates (Gisi et al, 2007).…”

Section: Backg Rou N Dmentioning

confidence: 99%

Stepwise accumulation of mutations in CesA3 in Phytophthora sojae results in increasing resistance to CAA fungicides

Cai

Zhang

Wang

et al. 2020

Evolutionary Applications

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Section: Backg Rou N Dmentioning

confidence: 99%

Stepwise accumulation of mutations in CesA3 in Phytophthora sojae results in increasing resistance to CAA fungicides

Cai

Zhang

Wang

et al. 2020

Evolutionary Applications

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“…Although CAAs may interfere with cell membranes, it is doubtful whether the observed effects on phosphocholinetransferase, the last step in the Kennedy pathway of lecithin biosynthesis (Griffiths et al 2003) can be considered as primary effects caused by CAA fungicides. Similarly, the observed changes in cell wall architecture and deposition during germination of cystospores (Jende et al 2002) may be a secondary effect, because some of the key enzymes of cell wall biosynthesis such as glucanases and synthases of β-1,3 glucans and cellulose may not be inhibited directly (Mehl and Buchenauer 2002;Gisi et al 2007a). Most likely, the target site for CAA fungicides may be membrane-bound at the interface between plasmalemma and cell wall (Syngenta internal data).…”

Section: Caa Fungicidesmentioning

confidence: 94%

“…The biochemical mode of action of CAA fungicides (including dimethomorph, flumorph, iprovalicarb, benthiavalicarb, mandipropamid) is still speculative; potential targets are phospholipid biosynthesis (Griffiths et al 2003) and cell wall deposition (Jende et al 2002;Gisi et al 2007a). Although CAAs may interfere with cell membranes, it is doubtful whether the observed effects on phosphocholinetransferase, the last step in the Kennedy pathway of lecithin biosynthesis (Griffiths et al 2003) can be considered as primary effects caused by CAA fungicides.…”

Section: Caa Fungicidesmentioning

confidence: 97%

Fungicide modes of action and resistance in downy mildews

2008

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Among oomycetes, Plasmopara viticola on grape and Phytophthora infestans on potato are agronomically the most important pathogens requiring control measures to avoid crop losses. Several chemical classes of fungicides are available with different properties in systemicity, specificity, duration of activity and risk of resistance. The major site-specific fungicides are the Quinone outside inhibitors (QoIs; e.g. azoxystrobin), phenylamides (e.g. mefenoxam), carboxylic acid amides (CAAs; e.g. dimethomorph, mandipropamid) and cyano-acetamide oximes (cymoxanil). In addition, multi-site fungicides such as mancozeb, folpet, chlorothalonil and copper formulations are important for disease control especially in mixtures or in alternation with site-specific fungicides. QoIs inhibit mitochondrial respiration, phenylamides the polymerization of r-RNA, whereas the mode of action of the other two site-specific classes is unknown but not multi-site. The use of site-specific fungicides has in many cases selected for resistant pathogen populations. QoIs are known to follow maternal, largely monogenic inheritance of resistance; they bear a high resistance risk for many but not all oomycetes. For phenylamides, inheritance of resistance is based on nuclear, probably monogenic mechanisms involving one or two semidominant genes; resistance risk is high for all oomycetes. The molecular mechanism of resistance to QoIs is mostly based on the G143A mutation in the cytochrome b gene; for phenylamides it is largely unknown. Resistance risk for CAA fungicides is considered as low to moderate depending on the pathogen species. Resistance to CAAs is controlled by two nuclear, recessive genes; the molecular mechanism is unknown. For QoIs and CAAs, resistance in field populations of P. viticola may gradually decline when applications are stopped.

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“…However, ferulic acid derivatives have not been developed as commercial antiplant virus agents. 23 Furthermore, as a unique nitrogen-balanced symmetric structure, piperazine can effectively improve the pharmacokinetic properties of a drug, increase the basicity and water solubility of the molecule, and adjust the lipid-water partition coefficient and acid-base equilibrium constant. 24 Therefore, piperazine is often used as a link in drug structural modification.…”

Section: Introductionmentioning

confidence: 99%

Ferulic acid derivatives with piperazine moiety as potential antiviral agents

Yuan

Wang

Liú

et al. 2022

Pest Management Science

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Background Plant virus diseases are difficult to control and severely threaten the productivity of crops, which leads to huge financial losses. To discover the new antiviral drugs, 34 novel ferulic acid derivatives with piperazine moiety were synthesized, and the antiviral activities were systematically screened as well. Results Bioassay results indicated that most of the target compounds had outstanding antiviral activities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) in vivo. In particular, compound E2 exhibited remarkable curative activities to TMV and CMV with EC50 values of 189.0 and 401.7 μg/mL compared to those for ningnanmycin (387.0, 519.3 μg/mL) and ribavirin (542.1, 721.5 μg/mL). And then the mechanisms of compound E2 were studied by chlorophyll content, differentially expressed proteins and genes tests. Conclusion The excellent antiviral activity of compound E2 was closely associated with the increase in host photosynthesis, which was confirmed by chlorophyll content, differentially expressed proteins and genes assays. Compound E2 can be considered as a lead structure for the discovery of new antiviral agents. © 2022 Society of Chemical Industry.

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Carboxylic Acid Amide (CAA) Fungicides

Cited by 10 publications

References 37 publications

Stepwise accumulation of mutations in CesA3 in Phytophthora sojae results in increasing resistance to CAA fungicides

Stepwise accumulation of mutations in CesA3 in Phytophthora sojae results in increasing resistance to CAA fungicides

Fungicide modes of action and resistance in downy mildews

Ferulic acid derivatives with piperazine moiety as potential antiviral agents

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