Synthesis and activities of tolprocarb derivatives against &lt;i&gt;Pyricularia oryzae&lt;/i&gt;: relationships among the activities for polyketide synthase, melanin biosynthesis, and rice blast

Banba, Shinichi; Hamada, Takahiro; Araki, Natsuko; Ebihara, Koichi

doi:10.1584/jpestics.d16-100

Cited by 12 publications

(8 citation statements)

References 23 publications

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“…Thus, the resistance risks of these chemical classes are assumed to be low, making them good candidates for resistance management strategies. Recently, some new fungicides, such as tolprocarb 13) and tebufloquin, were registered to control blast. These chemicals could also be candidates for resistance management strategies.…”

Section: Table 5 Panicle Blast Incidence In Each Plot In Saga In 200mentioning

confidence: 99%

Management of melanin biosynthesis dehydratase inhibitor (MBI-D)-resistance in <i>Pyricularia oryzae</i> using a non-MBI-D fungicidal application program for nursery boxes and a diclocymet and ferimzone mixture for field foliar applications

Kimura

Fukuchi

2018

Journal of Pesticide Science

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We compared the risk of reselecting melanin biosynthesis dehydratase inhibitor (MBI-D)-resistant Pyricularia oryzae isolates between two treatment programs, a nursery box application of diclocymet and a rotational program in which nursery boxes received a non-MBI-D fungicide application and then later, in the field, a foliar application of a diclocymet and ferimzone mixture. Both were effective against panicle blast. However, the latter prevented the reselection of MBI-D-resistant isolates more effectively than the former.

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Section: Table 5 Panicle Blast Incidence In Each Plot In Saga In 200mentioning

confidence: 99%

Management of melanin biosynthesis dehydratase inhibitor (MBI-D)-resistance in <i>Pyricularia oryzae</i> using a non-MBI-D fungicidal application program for nursery boxes and a diclocymet and ferimzone mixture for field foliar applications

Kimura

Fukuchi

2018

Journal of Pesticide Science

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“…Melanin biosynthetic enzymes are targets of agrochemical development, and three types of commercial melanin biosynthesis inhibitors (MBIs) have been developed ( Figure 2 ). These inhibitors are classified into three groups: MBI-R (tricyclazole, pyroquilon, and phthalide), MBI-D (carpropamid, diclocymet, and fenoxanil), and MBI-P (tolprocarb) [ 20 , 21 , 22 ]. The targets of MBI-R, MBI-D, and MBI-P are 1,3,8-trihydroxynaphthalene reductase (3HNR/BUF1), scytalone dehydratase (SDH1/RSY1), and polyketide synthase (ALB1), respectively.…”

Section: Melaninmentioning

confidence: 99%

Secondary Metabolites of the Rice Blast Fungus Pyricularia oryzae: Biosynthesis and Biological Function

Motoyama

2020

IJMS

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Plant pathogenic fungi produce a wide variety of secondary metabolites with unique and complex structures. However, most fungal secondary metabolism genes are poorly expressed under laboratory conditions. Moreover, the relationship between pathogenicity and secondary metabolites remains unclear. To activate silent gene clusters in fungi, successful approaches such as epigenetic control, promoter exchange, and heterologous expression have been reported. Pyricularia oryzae, a well-characterized plant pathogenic fungus, is the causal pathogen of rice blast disease. P. oryzae is also rich in secondary metabolism genes. However, biosynthetic genes for only four groups of secondary metabolites have been well characterized in this fungus. Biosynthetic genes for two of the four groups of secondary metabolites have been identified by activating secondary metabolism. This review focuses on the biosynthesis and roles of the four groups of secondary metabolites produced by P. oryzae. These secondary metabolites include melanin, a polyketide compound required for rice infection; pyriculols, phytotoxic polyketide compounds; nectriapyrones, antibacterial polyketide compounds produced mainly by symbiotic fungi including endophytes and plant pathogens; and tenuazonic acid, a well-known mycotoxin produced by various plant pathogenic fungi and biosynthesized by a unique NRPS-PKS enzyme.

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“…Finally, after considering various factors, such as long residual activity in the field trial, tolprocarb was selected as the developed compound. 9,10)…”

Section: Discovery Of Lead Compoundmentioning

confidence: 99%

“…1) is a fungicide developed by Mitsui Chemicals Agro, Inc., Tokyo, Japan, to control rice blast (causal agent; Magnaporthe grisea) in paddy fields. 1) Rice blast is an extremely harmful disease that affects the rice production; controlling this fungus poses is major challenge because fungicide-resistant strains can develop. Although there are many modes of action to control the disease, some fungicides become insensitive to disease.…”

Section: Introductionmentioning

confidence: 99%

Development of a novel fungicide, tolprocarb

et al. 2019

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Tolprocarb developed by Mitsui Chemicals Agro, Inc. (Tokyo, Japan) was discovered as a new oomycete fungicide. However, its antifungal spectrum and action mechanisms against fungi are completely different from those of the original compound, iprovalicarb. Tolprocarb has a potent and highly controlled effect on a rice blast fungus Magnaporthe grisea, and its mode of action was revealed to be the inhibition of polyketide synthase in the melanin biosynthesis pathway. In addition, tolprocarb induced systemic acquired resistance in Arabidopsis thaliana and rice (Oryza sativa L.). Owing to these double modes of action, tolprocarb can effectively control not only rice blast but also bacterial diseases, and has a low risk of developing fungicide-resistant isolates. Tolprocarb also provides long-term residual activity. A meta-analysis was performed in order to demonstrate tolprocarb's superior control against panicle blast in paddy fields. In addition, tolprocarb did not show cross-resistance against the fungi that are resistant to dehydratase inhibitor in melanin biosynthesis (Melanin Biosynthesis Inhibitor-Dehydratase; MBI-D) or respiratory complex III: cytochrome bc 1 at Quinone outside site inhibitor (Quinone outside Inhibitor; QoI). Owing to its stable effects, tolprocarb appears to be a suitable choice for practical use against fungi in the rice production field.

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Synthesis and activities of tolprocarb derivatives against <i>Pyricularia oryzae</i>: relationships among the activities for polyketide synthase, melanin biosynthesis, and rice blast

Cited by 12 publications

References 23 publications

Management of melanin biosynthesis dehydratase inhibitor (MBI-D)-resistance in <i>Pyricularia oryzae</i> using a non-MBI-D fungicidal application program for nursery boxes and a diclocymet and ferimzone mixture for field foliar applications

Management of melanin biosynthesis dehydratase inhibitor (MBI-D)-resistance in <i>Pyricularia oryzae</i> using a non-MBI-D fungicidal application program for nursery boxes and a diclocymet and ferimzone mixture for field foliar applications

Secondary Metabolites of the Rice Blast Fungus Pyricularia oryzae: Biosynthesis and Biological Function

Development of a novel fungicide, tolprocarb

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