Action mechanism of a novel herbicide, pyroxasulfone

Tanetani, Yoshitaka; Kaku, Koichiro; Kawai, Kiyoshi; Fujioka, Tomonori; Shimizu, Tsutomu

doi:10.1016/j.pestbp.2009.06.003

Cited by 122 publications

(135 citation statements)

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“…1) This herbicide potently inhibits shoot elongation of weeds; however, selectivity was observed in growth inhibition between weeds and crops. 12,13) We have already reported that pyroxasulfone is a potent inhibitor of the very long-chain fatty acid elongase (VLCFAE) of plants. 12) The difference in the sensitivity of plant VLCFAEs to pyroxasulfone was partly involved in the selectivity of this herbicide.…”

Section: Introductionmentioning

confidence: 99%

Role of metabolism in the selectivity of a herbicide, pyroxasulfone, between wheat and rigid ryegrass seedlings

et al. 2013

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Metabolism of pyroxasulfone in a tolerant crop, wheat and a susceptible plant, rigid ryegrass, was studied using 14 C-pyroxasulfone. The main metabolites were a cysteine conjugate of the isoxazoline ring (M-26), deaminated M-26 (M-29) and a glucose conjugate of M-29, suggesting that the main metabolic route in both plants was the cleavage of the methylenesulfonyl linkage caused by glutathione conjugation. The difference in the metabolic activity was assumed to be one of the factors in determining the selectivity of pyroxasulfone between wheat and rigid ryegrass.

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Section: Introductionmentioning

confidence: 99%

Role of metabolism in the selectivity of a herbicide, pyroxasulfone, between wheat and rigid ryegrass seedlings

et al. 2013

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“…19) Thiobencarb was dissolved in acetone and added to the medium. After 15 days of culture, the cultured cells, from which the liquid medium had been completely eliminated using a pipette, were transferred to a new container and weighed.…”

Section: Effect Of Thiobencarb On the Growth Of Barnyard Millet Cultumentioning

confidence: 99%

“…19) Thiobencarb was dissolved in acetone and added to the medium. The final concentration of acetone was 0.1%.…”

Section: Effect Of Thiobencarb On the Growth Of Plant Shootsmentioning

confidence: 99%

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Action mechanism of a herbicide, thiobencarb

et al. 2013

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The action mechanism of thiobencarb was studied by examining the inhibitory effects of this herbicide on the biosynthesis of very-long-chain fatty acids (VLCFAs). Thiobencarb treatment decreased VLCFAs, such as C20:0, C20:1, C22:0, C24:0, C24:1 and C26:0 fatty acids, and increased long-chain-fatty acids and medium-chain-fatty acids, such as C14:0, C15:0, C18:0 and C18:1 fatty acids, which are precursors of VLCFAs, in barnyard millet cultured cells. Thiobencarb sulfoxide and sulfone potently inhibited VLCFA elongase (VLCFAE) activity in the microsomal fraction of etiolated barnyard millet seedlings, although thiobencarb itself slightly inhibited it. These results suggested that thiobencarb is a VLCFAE-inhibiting herbicide whose active forms are its oxidized metabolites, such as sulfoxide and sulfone. Thiobencarb sulfoxide inhibited the VLCFAE activity of the microsomal fraction of etiolated barnyard millet seedlings in a time-independent manner. This time-independent inhibition proposed a reversible inhibition mechanism of the VLCFAE by thiobencarb sulfoxide, likely with isoxazoline-type herbicides, such as pyroxasulfone, which have been classified into group K3 of the Herbicide Resistance Action Committee (HRAC) in the U.S. It is assumed that the time-independent reversible inhibition of VLCFAE is applicable to other thiocarbamate herbicides presently classified into group N of the HRAC. © Pesticide Science Society of Japan Keywords: thiobencarb, thiobencarb sulfoxide, very-long-chain fatty acid (VLCFA), very-long-chain fatty acid elongase (VLCFAE), time-independent manner, N group. IntroductionThiobencarb, S-(4-chlorobenzyl)-N,N-diethylthiocarbamate, is a herbicide developed by Kumiai Chemical Industry for crops such as rice, wheat, corn and soybean (Fig. 1A).1) This herbicide at the application rate of 1.5-7.5 kg a.i./ha provides good efficacy on both grass and broad leaf weeds, especially needle spikerush and barnyard grass.2) Barnyard grass from pre-emergence up to the three-leaf stage is effectively controlled by this herbicide. This herbicide shows excellent selectivity for rice plants.Differences in the physiological activity between rice and barnyard grass for absorbing and metabolizing this herbicide have been reported. 3-5)Thiobencarb does not inhibit the germination of seeds but potently inhibits the shoot elongation of germinated seeds. This herbicide belongs to the thiocarbamate herbicides and is classified into group N of the Herbicide Resistance Action Committee (HRAC) in the U.S.6) According to the HRAC, the target site of the group N herbicides is described as the lipid synthesis except for acetyl-CoA carboxylase (ACCase), indicating that their mode of action has not been completely elucidated. 7,8) However, it has been reported that sulfoxide of pebulate, which is also a thiocarbamate herbicide, inhibits the incorporation of 14 Clabeled acetic acid into very-long-chain fatty acids (VLCFAs) in some plants. 9,10) Therefore, the thiocarbamate herbicides were presumed to inhibit the biosynthesis of...

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“…5) Pyroxasulfone's mode of action is the inhibition of the elongation steps of very-long chain fatty acid (VLCFA) synthesis. 6) Among preemergence herbicides pyroxasulfone has a unique chemistry that allows lower use rates (60 to 250 g a.i./ha) than other VLCFA synthesis-inhibiting herbicides, such as S-metolachlor and acetochlor. Pyroxasulfone also has a lower water solubility and lower vapor pressure as compared to the acetoanilide herbicides.…”

Section: Introductionmentioning

confidence: 99%

Weed control efficacy of a novel herbicide, pyroxasulfone

Yamaji

Honda²,

Kobayashi³

et al. 2014

J. Pestic. Sci.

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Pyroxasulfone is a new herbicide developed by Kumiai Chemical Industry Co., Ltd. It has been registered in several countries for use in corn, soybeans, cotton, and wheat. Growth inhibition tests, greenhouse tests, and a field trial were conducted to evaluate the herbicidal efficacy of pyroxasulfone. Pyroxasulfone exhibited an excellent herbicidal activity at lower application rates as compared to S-metolachlor and has shown sufficient residual activity. Pyroxasulfone is one effective tool for the weed management programs.

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Action mechanism of a novel herbicide, pyroxasulfone

Cited by 122 publications

References 11 publications

Role of metabolism in the selectivity of a herbicide, pyroxasulfone, between wheat and rigid ryegrass seedlings

Role of metabolism in the selectivity of a herbicide, pyroxasulfone, between wheat and rigid ryegrass seedlings

Action mechanism of a herbicide, thiobencarb

Weed control efficacy of a novel herbicide, pyroxasulfone

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