Pyroxasulfone | CAS# 447399-55-5 | Inhibitor

MedKoo Cat#: 574854 | Name: Pyroxasulfone

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pyroxasulfone is a pre-emergence herbicide that is used to control grass weed species in major field crops.

Chemical Structure

Pyroxasulfone

CAS#447399-55-5

Theoretical Analysis

MedKoo Cat#: 574854

Name: Pyroxasulfone

CAS#: 447399-55-5

Chemical Formula: C12H14F5N3O4S

Exact Mass: 391.0625

Molecular Weight: 391.31

Elemental Analysis: C, 36.83; H, 3.61; F, 24.28; N, 10.74; O, 16.35; S, 8.19

Price and Availability

Size	Price	Availability
1g	USD 350.00	2 Weeks
5g	USD 750.00	2 Weeks
25g	USD 1,250.00	2 Weeks

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Synonym

KIH 485; Sakura; Sakura 850 WG; Sakura 85WG; Pyroxasulfone

IUPAC/Chemical Name

3-[[[5-(Difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl]sulfonyl]-4,5-dihydro-5,5-dimethyl-isoxazole

InChi Key

CASLETQIYIQFTQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C12H14F5N3O4S/c1-11(2)4-7(19-24-11)25(21,22)5-6-8(12(15,16)17)18-20(3)9(6)23-10(13)14/h10H,4-5H2,1-3H3

SMILES Code

CC1(C)CC(S(=O)(CC2=C(OC(F)F)N(C)N=C2C(F)(F)F)=O)=NO1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

In vitro activity:

In this study, pyroxasulfone exhibited potent herbicidal efficacy, providing up to 98% control of Echinochloa crus-galli for up to 63 days. It had a use rate lower than chloroacetamide herbicides. The low water solubility and the low vapor pressure of pyroxasulfone resulted in limited horizontal diffusion on the soil surface and low risk of volatilization, respectively. The herbicidal efficacy of pyroxasulfone was affected by clod size and improved with smooth soil surface preparation. Reference: J Pestic Sci. 2016 Feb 20;41(1):1-5. https://pubmed.ncbi.nlm.nih.gov/30364756/

In vivo activity:

This phenomenon occurred at high doses, suggesting a limited carcinogenic risk to humans unless exposed to levels causing urinary tract crystal formation. Pyroxasulfone had a low incidence of urinary bladder tumors at high concentrations in mice with no increased tumor incidence. These findings suggest that pyroxasulfone-associated bladder tumors in male rats result from urinary crystal formation, urothelial cytotoxicity, and subsequent regenerative proliferation. Reference: Toxicol Mech Methods. 2020 Nov;30(9):656-671. https://pubmed.ncbi.nlm.nih.gov/32746684/

Preparing Stock Solutions

The following data is based on the product molecular weight 391.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Yamaji Y, Honda H, Hanai R, Inoue J. Soil and environmental factors affecting the efficacy of pyroxasulfone for weed control. J Pestic Sci. 2016 Feb 20;41(1):1-5. doi: 10.1584/jpestics.D15-047. PMID: 30364756; PMCID: PMC6200051. 2. Wang Y, Men J, Zheng T, Ma Y, Li W, Cernava T, Bai L, Jin D. Impact of pyroxasulfone on sugarcane rhizosphere microbiome and functioning during field degradation. J Hazard Mater. 2023 Aug 5;455:131608. doi: 10.1016/j.jhazmat.2023.131608. Epub 2023 May 9. PMID: 37178534. 3. Kyoya T, Arnold LL, Pennington KL, Kakiuchi-Kiyota S, Terada M, Abe K, Cohen SM. Urinary crystal formation and urothelial effects of pyroxasulfone administered to male rats. Toxicol Mech Methods. 2020 Nov;30(9):656-671. doi: 10.1080/15376516.2020.1805666. Epub 2020 Sep 4. PMID: 32746684.

In vitro protocol:

In vivo protocol:

1. Wang Y, Men J, Zheng T, Ma Y, Li W, Cernava T, Bai L, Jin D. Impact of pyroxasulfone on sugarcane rhizosphere microbiome and functioning during field degradation. J Hazard Mater. 2023 Aug 5;455:131608. doi: 10.1016/j.jhazmat.2023.131608. Epub 2023 May 9. PMID: 37178534. 2. Kyoya T, Arnold LL, Pennington KL, Kakiuchi-Kiyota S, Terada M, Abe K, Cohen SM. Urinary crystal formation and urothelial effects of pyroxasulfone administered to male rats. Toxicol Mech Methods. 2020 Nov;30(9):656-671. doi: 10.1080/15376516.2020.1805666. Epub 2020 Sep 4. PMID: 32746684.

1: Mita MR, Mendes KF. Pre-emergence herbicides mixture in soybeans: Amaranthus hybridus control and crop selectivity on cover crops soil. J Environ Sci Health B. 2024;59(8):497-506. doi: 10.1080/03601234.2024.2372920. Epub 2024 Jul 3. PMID: 38958072. 2: Araldi de Castro R, de Castro SGQ, Quassi de Castro SA, Piassa A, Soares GODN, Tropaldi L, Christofoletti PJ. Optimizing herbicide selection for pre- emergence control of itchgrass and cypressvine morningglory in sugarcane. J Environ Sci Health B. 2024;59(6):350-360. doi: 10.1080/03601234.2024.2352321. Epub 2024 May 13. PMID: 38736380. 3: Kaur A, Kaur P, Kaur H. Investigating the impact of soil properties, application rates and environmental conditions on pyroxasulfone dissipation and its ecotoxicological effects on soil health in aridisols of Punjab. Environ Monit Assess. 2024 Apr 16;196(5):455. doi: 10.1007/s10661-024-12605-2. PMID: 38625667. 4: Parven A, Md Meftaul I, Venkateswarlu K, Gopalan S, Megharaj M. Pre-emergence herbicides widely used in urban and farmland soils: fate, and potential human and environmental health risks. Environ Geochem Health. 2024 Mar 14;46(4):132. doi: 10.1007/s10653-024-01907-6. PMID: 38483701; PMCID: PMC10940459. 5: Costa LS, Schettino CF, Sicupira LC, de Pinho GP, Silvério FO. Determining pyroxasulfone herbicide in honey samples using liquid-liquid extraction with low temperature purification (LLE-LTP). Talanta. 2024 Jun 1;273:125870. doi: 10.1016/j.talanta.2024.125870. Epub 2024 Mar 2. PMID: 38460423. 6: Goggin DE, Cawthray GR, Busi R. Pyroxasulfone Metabolism in Resistant Lolium rigidum: Is It All Down to GST Activity? J Agric Food Chem. 2024 Feb 28;72(8):3937-3948. doi: 10.1021/acs.jafc.3c08141. Epub 2024 Feb 14. PMID: 38354096. 7: Kerr DR, Concepcion JCT, Strom SA, Riechers DE. Quantifying resistance to very-long-chain fatty acid-inhibiting herbicides in Amaranthus tuberculatus using a soilless assay. PLoS One. 2023 Dec 22;18(12):e0295927. doi: 10.1371/journal.pone.0295927. PMID: 38134124; PMCID: PMC10745185. 8: Wang Y, Men J, Zheng T, Ma Y, Li W, Cernava T, Bai L, Jin D. Impact of pyroxasulfone on sugarcane rhizosphere microbiome and functioning during field degradation. J Hazard Mater. 2023 Aug 5;455:131608. doi: 10.1016/j.jhazmat.2023.131608. Epub 2023 May 9. PMID: 37178534. 9: Parcharidou E, Dücker R, Zöllner P, Ries S, Orru R, Beffa R. Recombinant glutathione transferases from flufenacet-resistant black-grass (Alopecurus myosuroides Huds.) form different flufenacet metabolites and differ in their interaction with pre- and post-emergence herbicides. Pest Manag Sci. 2023 Sep;79(9):3376-3386. doi: 10.1002/ps.7523. Epub 2023 May 19. PMID: 37132078. 10: Zhang JJ, Niu Y, Ma C, Zhao T, Wang H, Yan Z, Zhou L, Liu X, Piao F, Du N. Accumulation and metabolism of pyroxasulfone in tomato seedlings. Ecotoxicol Environ Saf. 2023 Apr 1;254:114765. doi: 10.1016/j.ecoenv.2023.114765. Epub 2023 Mar 10. PMID: 36907092. 11: Cai Z, Zhang W, Yan Z, Du X. Synthesis of Novel Pyrazole Derivatives Containing Phenylpyridine Moieties with Herbicidal Activity. Molecules. 2022 Sep 23;27(19):6274. doi: 10.3390/molecules27196274. PMID: 36234814; PMCID: PMC9571195. 12: Kibasa V, Mahajan G, Chauhan BS. Seed germination ecology of hood canarygrass (Phalaris paradoxa L.) and herbicide options for its control. Sci Rep. 2022 Sep 9;12(1):15241. doi: 10.1038/s41598-022-19418-8. PMID: 36085300; PMCID: PMC9463434. 13: Ekeleme F, Dixon A, Atser G, Hauser S, Chikoye D, Korie S, Olojede A, Agada M, Olorunmaiye PM. Increasing cassava root yield on farmers' fields in Nigeria through appropriate weed management. Crop Prot. 2021 Dec;150:105810. doi: 10.1016/j.cropro.2021.105810. PMID: 34866731; PMCID: PMC8505754. 14: Perez MB, Beckie HJ, Cawthray GR, Goggin DE, Busi R. Rapid On-Farm Testing of Resistance in Lolium rigidum to Key Pre- and Post-Emergence Herbicides. Plants (Basel). 2021 Sep 10;10(9):1879. doi: 10.3390/plants10091879. PMID: 34579410; PMCID: PMC8467281. 15: Mahajan G, Chauhan BS. Evaluation of Preemergent Herbicides for Chloris virgata Control in Mungbean. Plants (Basel). 2021 Aug 9;10(8):1632. doi: 10.3390/plants10081632. PMID: 34451677; PMCID: PMC8398657. 16: Busi R, Beckie HJ, Bates A, Boyes T, Davey C, Haskins B, Mock S, Newman P, Porri A, Onofri A. Herbicide resistance across the Australian continent. Pest Manag Sci. 2021 Nov;77(11):5139-5148. doi: 10.1002/ps.6554. Epub 2021 Jul 31. PMID: 34260812. 17: Goggin DE, Cawthray GR, Flematti GR, Bringans SD, Lim H, Beckie HJ, Busi R. Pyroxasulfone-Resistant Annual Ryegrass (Lolium rigidum) Has Enhanced Capacity for Glutathione Transferase-Mediated Pyroxasulfone Conjugation. J Agric Food Chem. 2021 Jun 16;69(23):6414-6422. doi: 10.1021/acs.jafc.0c07458. Epub 2021 Jun 3. PMID: 34081453. 18: Recsei C, Barda Y. Synthesis of bis(aryloxy)fluoromethanes using a heterodihalocarbene strategy. Beilstein J Org Chem. 2021 Apr 12;17:813-818. doi: 10.3762/bjoc.17.70. PMID: 33936312; PMCID: PMC8056069. 19: Kyoya T, Arnold LL, Pennington KL, Kakiuchi-Kiyota S, Terada M, Abe K, Cohen SM. Urinary crystal formation and urothelial effects of pyroxasulfone administered to male rats. Toxicol Mech Methods. 2020 Nov;30(9):656-671. doi: 10.1080/15376516.2020.1805666. Epub 2020 Sep 4. PMID: 32746684. 20: Khalil Y, Flower K, Siddique KH, Ward P. Pyroxasulfone efficacy for annual ryegrass control is affected by wheat residue height, amount and orientation. Pest Manag Sci. 2020 Mar;76(3):861-867. doi: 10.1002/ps.5590. Epub 2019 Sep 30. PMID: 31429186.