Characterization of very long chain fatty acid synthesis inhibition by ipfencarbazone

Kasahara, Tatsuya; Matsumoto, Hiroshi; Hasegawa, Hisakazu; Koyama, Kohei; Takeuchi, Takashi

doi:10.1584/jpestics.d18-057

Cited by 5 publications

(6 citation statements)

References 14 publications

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“…For example, the target and mechanism of action of ipfencarbazone herbicide were predicted as very long chain fatty acid (VLCFA) synthesis inhibition (K 3 group) and mitosis inhibition (15 group), respectively, on the basis of the proposed method (Forouzesh et al, 2015). Ipfencarbazone inhibited the incorporation of [2- 14 C] malonyl-CoA into stearoyl-CoA (C18:0) and arachidoyl-CoA (C20:0) in rice and late watergrass microsomes at a low concentration (IC 50 less than 1 µM), similar to cafenstrole, a known VLCFA synthesis inhibitor (Kasahara et al, 2019). Therefore, the target of ipfencarbazone was considered to be VLCFA synthesis inhibition (Kasahara et al, 2019).…”

Section: Resultsmentioning

confidence: 99%

“…Ipfencarbazone inhibited the incorporation of [2- 14 C] malonyl-CoA into stearoyl-CoA (C18:0) and arachidoyl-CoA (C20:0) in rice and late watergrass microsomes at a low concentration (IC 50 less than 1 µM), similar to cafenstrole, a known VLCFA synthesis inhibitor (Kasahara et al, 2019). Therefore, the target of ipfencarbazone was considered to be VLCFA synthesis inhibition (Kasahara et al, 2019).…”

Section: Resultsmentioning

confidence: 99%

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Reliable Target Prediction of Bioactive Molecules Based on Chemical Similarity Without Employing Statistical Methods

et al. 2019

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The prediction of biological targets of bioactive molecules from machine-readable materials can be routinely performed by computational target prediction tools (CTPTs). However, the prediction of biological targets of bioactive molecules from non-digital materials (e.g., printed or handwritten documents) has not been possible due to the complex nature of bioactive molecules and impossibility of employing computations. Improving the target prediction accuracy is the most important challenge for computational target prediction. A minimum structure is identified for each group of neighbor molecules in the proposed method. Each group of neighbor molecules represents a distinct structural class of molecules with the same function in relation to the target. The minimum structure is employed as a query to search for molecules that perfectly satisfy the minimum structure of what is guessed crucial for the targeted activity. The proposed method is based on chemical similarity, but only molecules that perfectly satisfy the minimum structure are considered. Structurally related bioactive molecules found with the same minimum structure were considered as neighbor molecules of the query molecule. The known target of the neighbor molecule is used as a reference for predicting the target of the neighbor molecule with an unknown target. A lot of information is needed to identify the minimum structure, because it is necessary to know which part(s) of the bioactive molecule determines the precise target or targets responsible for the observed phenotype. Therefore, the predicted target based on the minimum structure without employing the statistical significance is considered as a reliable prediction. Since only molecules that perfectly (and not partly) satisfy the minimum structure are considered, the minimum structure can be used without similarity calculations in non-digital materials and with similarity calculations (perfect similarity) in machine-readable materials. Nine tools (PASS online, PPB, SEA, TargetHunter, PharmMapper, ChemProt, HitPick, SuperPred, and SPiDER), which can be used for computational target prediction, are compared with the proposed method for 550 target predictions. The proposed method, SEA, PPB, and PASS online, showed the best quality and quantity for the accurate predictions.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Reliable Target Prediction of Bioactive Molecules Based on Chemical Similarity Without Employing Statistical Methods

et al. 2019

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“…from pre-emergence to the three-leaf stage while being safe for transplanted rice at a dosage of 250 g a.i./ha. 102,103) It has excellent effect persistence and has a residual effect for about 70 days against barnyard grass.…”

Section: Vlcfae Inhibitorsmentioning

confidence: 99%

Development of novel pesticides in the 21st century

2020

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General trends and strategies for novel pesticides are summarized. Global pesticide sales and pesticide discovery research are also briefly reviewed. At least 105 chemical pesticides have been launched during the past decade or are under development: 43 fungicides, 34 insecticides/acaricides, 6 nematicides, 21 herbicides, and 1 herbicide safener. Most of them are safe to humans and environmentally friendly. The most developed fungicides are SDHI (succinate dehydrogenase inhibitors), DMI (demethylation inhibitors), QoI (quinone outside inhibitors), and QiI (quinone inside inhibitors). Due to the development of resistance to fungicides with existing modes of action, many fungicides possessing various novel modes of action have been launched or are under development. The trend of insecticide development is changing from organophosphorus, carbamate, and synthetic pyrethroids to nicotinic and diamide insecticides. During the past decade, compounds possessing a variety of novel modes of action have also been launched or are under development. Flupyradifurone and flupyrimin, exhibiting extremely low honeybee toxicity, have been developed and subjected to practical use. Herbicides possessing varied modes of action, such as acetolactate synthase, p-hydroxyphenylpyruvate dioxygenase, protoporphyrinogen oxidase, and very-long-chain fatty acid elongase inhibition, have been developed, but no herbicides possessing a novel mode action have commercialized in nearly 30 years. It is of interest that cyclopyrimorate, which was recently launched, and tetflupyrolimet, which is under development, have novel modes action: homogentisate solanesyltransferase (HST) and dihydroorotate dehydrogenase (DHODH) inhibition, respectively. The development of useful acaricides and nematicides is also progressing. Some natural product origin pesticides are getting attention.

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“…As an early herbicide of chloroacetamide, acetochlor occupies a large market, and metolachlor is the same as acetochlor [15–19] . Subsequently, Syngenta developed the optically active isomer S‐metolachlor [20–24] . In 2016, worldwide sales of S‐metolachlor reached $590 million, making it the largest acetamide herbicide, surpassing acetochlor.…”

Section: Introductionmentioning

confidence: 99%

“…[15][16][17][18][19] Subsequently, Syngenta developed the optically active isomer S-metolachlor. [20][21][22][23][24] In 2016, worldwide sales of S-metolachlor reached $590 million, making it the largest acetamide herbicide, surpassing acetochlor. At present, with the exposure of acetochlor and isopromethachlor potential hazards to human and the forbiddance of acetochlor in European Union, the herbicides containing the structural type of 3-sulfonylisooxazole, such as pyroxasulfone and fenoxasulfone were commercialized by Japanese companies in 2011 and 2014, respectively.…”

Section: Introductionmentioning

confidence: 99%

Discovery of novel 3‐{[(5,5‐dimethyl‐4,5‐dihydroisoxazol‐3‐yl)sulfonyl]methyl}benzo[d]isoxazole analogs as promising very long chain fatty acids inhibitors

Lin

Li²,

Hu³

et al. 2020

Journal of Heterocyclic Chem

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Very long chain fatty acids (VLCFAs) are one of the most principal and promising targets for herbicides discovery. In order to explore and find novel VLCFAs inhibitors with higher herbicidal activity and improved crop safety, a variety of new 3‐{[(5,5‐dimethyl‐4,5‐dihydroisoxazol‐3‐yl)sulfonyl]methyl}benzo[d]isoxazole derivatives were reasonably designed and synthesized. The results of greenhouse experiments indicated that several compounds exhibited good herbicidal activity against Digitaria sanguinalis, Echinochloa crus‐galli, and Setaria faberii at rates of 150 g ai/ha. Compounds g4 and h1 displayed promising herbicidal activity against D sanguinalis and E crus‐galli at rates of 75 g ai/ha, which is better than commercial pyroxasulfone and S‐metolachlor. Moreover, compound h1 displayed higher activity against E crus‐galli, D sanguinalis, and S faberii than pyroxasulfone and S‐metolachlor even at a rate of 37.5 and 18.75 g ai/ha. Furthermore, both of the compounds g4 and h1 were much safer to these tested crops, especially to rice, wheat and rape, at the rate of 150 g ai/ha than pyroxasulfone. Therefore, h1 may act as a new lead structure for novel herbicides discovery.

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Characterization of very long chain fatty acid synthesis inhibition by ipfencarbazone

Cited by 5 publications

References 14 publications

Reliable Target Prediction of Bioactive Molecules Based on Chemical Similarity Without Employing Statistical Methods

Reliable Target Prediction of Bioactive Molecules Based on Chemical Similarity Without Employing Statistical Methods

Development of novel pesticides in the 21st century

Discovery of novel 3‐{[(5,5‐dimethyl‐4,5‐dihydroisoxazol‐3‐yl)sulfonyl]methyl}benzo[d]isoxazole analogs as promising very long chain fatty acids inhibitors

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