Development of the novel pre-emergence herbicide pyroxasulfone

Nakatani, Masao; Yamaji, Yoshihiro; Honda, Hisashi; Uchida, Yoshiyuki

doi:10.1584/jpestics.j16-05

Cited by 32 publications

(24 citation statements)

References 9 publications

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“…The rate titration experiment included three VLCFA inhibitors (nonencapsulated acetochlor, S-metolachlor, and pyroxasulfone), each applied at 0.5X, 1X, 2X, and 4X doses based on the 1X manufacturer recommended rate (Table 2). Pyroxasulfone is a pyrazole and is applied at a much lower use rate; it was included in experiments due to having the same SOAs and target weed spectrum as chloroacetamide herbicides (Nakatani et al 2016;Tanetani et al 2009Tanetani et al , 2011. Treatments were applied on May 23, 2016, and June 14, 2017 with a pressurized CO 2 backpack sprayer calibrated to deliver 187 L ha −1 at 276 kPa with a 3-m boom consisting of six AI110025VS nozzles (TeeJet® Technologies, P.O.…”

Section: General Field Methodsmentioning

confidence: 99%

Characterization of multiple herbicide–resistant waterhemp (Amaranthus tuberculatus) populations from Illinois to VLCFA-inhibiting herbicides

et al. 2019

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Field experiments were conducted in 2016 and 2017 in Champaign County, IL, to study a waterhemp [Amaranthus tuberculatus (Moq.) J. D. Sauer] population (CHR) resistant to 2,4-D and 4-hydroxyphenylpyruvate dioxygenase (HPPD)-, photosystem II–, acetolactate synthase (ALS)-, and protoporphyrinogen oxidase–inhibiting herbicides. Two field experiments were designed to investigate the efficacy of very-long-chain fatty-acid (VLCFA)-inhibiting herbicides, including a comparison of active ingredients at labeled use rates and a rate titration experiment. Amaranthus tuberculatus density and control were evaluated at 28 and 42 d after treatment (DAT). Nonencapsulated acetochlor, alachlor, and pyroxasulfone provided the greatest PRE control of CHR (56% to 75%) at 28 DAT, while metolachlor, S-metolachlor, dimethenamid-P, and encapsulated acetochlor provided less than 27% control. In the rate titration study, nonencapsulated acetochlor controlled CHR more than equivalent field use rates of S-metolachlor. Subsequent dose–response experiments with acetochlor, S-metolachlor, dimethenamid-P, and pyroxasulfone in the greenhouse included three multiple herbicide–resistant (MHR) A. tuberculatus populations: CHR-M6 (progeny generated from CHR), MCR-NH40 (progeny generated from Mclean County, IL), and ACR (Adams County, IL), in comparison with a sensitive population (WUS). Both CHR-M6 and MCR-NH40 are MHR to atrazine and HPPD, and ALS inhibitors and demonstrated higher survival rates (LD50) to S-metolachlor, acetochlor, dimethenamid-P, or pyroxasulfone than ACR (atrazine resistant but HPPD-inhibitor sensitive) and WUS. Based on biomass reduction (GR50), resistant to sensitive (R:S) ratios between CHR-M6 and WUS were 7.5, 6.1, 5.5, and 2.9 for S-metolachlor, acetochlor, dimethenamid-P, and pyroxasulfone, respectively. Values were greater for MCR-NH40 than CHR-M6, and ACR was the most sensitive to all VLCFA inhibitors tested. Complete control of all populations was achieved at or below a field use rate of acetochlor. In summary, field studies demonstrated CHR is not controlled by several VLCFA-inhibiting herbicides. Greenhouse dose–response experiments corroborated field results and generated R:S ratios (LD50) ranging from 4.5 to 64 for CHR-M6 and MCR-NH40 among the four VLCFA-inhibiting herbicides evaluated.

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Section: General Field Methodsmentioning

confidence: 99%

Characterization of multiple herbicide–resistant waterhemp (Amaranthus tuberculatus) populations from Illinois to VLCFA-inhibiting herbicides

et al. 2019

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“…Pyrazole is an aromatic heterocyclic ring and could endow some agricultural chemicals good characteristics of specificity, high activity, low toxicity and environmental friendliness to meet the requirements of the modern agricultural herbicide design 21 . It appears in commercial agrochemicals such as pyroxasulfone, 22 chlorantraniliprole 23 and patented compounds 1‐acyl‐3‐phenyl‐pyrazol benzophenes 24 and 4‐(1H‐pyrazol‐1‐yl) pyrimidine derivatives 25 . Therefore, from the perspective of herbicide development, pyrazole as a specific functional group has been used widely in the structural design during discovery of novel herbicidal compounds.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and mode of action of novel 3‐chloro‐6‐pyrazolyl picolinate derivatives as herbicide candidates

Yang

Yin

et al. 2021

Pest Management Science

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BACKGROUND Picolinate/picolinic acid compounds are an important class of synthetic auxin herbicides. To explore the herbicidal activity of 6‐pyrazolyl picolinate compounds, a series of 3‐chloro‐6‐pyrazolyl‐picolinate derivatives was designed and synthesized. RESULTS Twenty‐five 3‐chloro‐6‐pyrazolyl‐picolinate derivatives synthesized were tested for herbicidal activity and the IC50 value of compound c5 to the growth of Arabidopsis thaliana root was 27 times lower than that of the commercial herbicide clopyralid. Compound c5 displayed better post‐emergence herbicidal activity and broader (Picloram, Clopyralid, Aminopyralid) herbicidal spectrum at a dosage of 400 g ha−1 in comparison with clopyralid; it also was safe to wheat and maize at this dosage. Arabidopsis thaliana phenotypes and expression of auxin‐response genes demonstrated that compound c5 might be a novel auxin‐type herbicide. Molecular docking analyses revealed that compound c5 had stronger binding ability to receptor AFB5 (auxin signaling F‐box protein 5) than clopyralid. CONCLUSION These 6‐pyrazolyl picolinate compounds could be used as potential lead structures for the discovery of a novel synthetic auxin herbicide. © 2021 Society of Chemical Industry

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“…It shows high efficacy against hardly controllable gramineous weeds such as Johnson grass and Urochloa platyphylla and is also highly effective against weeds that have acquired resistance to glyphosate, ALS inhibitors, ACCase inhibitors, and dinitroaniline herbicides. 87,101) Ipfencarbazone (Winner ® , Fighter ® ) is a triazolinone-based herbicide developed for paddy rice and exhibits high herbicid-al activity against Echinochloa spp. from pre-emergence to the three-leaf stage while being safe for transplanted rice at a dosage of 250 g a.i./ha.…”

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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Development of the novel pre-emergence herbicide pyroxasulfone

Cited by 32 publications

References 9 publications

Characterization of multiple herbicide–resistant waterhemp (Amaranthus tuberculatus) populations from Illinois to VLCFA-inhibiting herbicides

Characterization of multiple herbicide–resistant waterhemp (Amaranthus tuberculatus) populations from Illinois to VLCFA-inhibiting herbicides

Design, synthesis and mode of action of novel 3‐chloro‐6‐pyrazolyl picolinate derivatives as herbicide candidates

Development of novel pesticides in the 21st century

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