Metabolism / Metabolites
Liquid chromatography-mass spectrometry (LC-MS) identified the metabolite of fromethacin as (N-(4-(4-(trifluoromethyl)phenoxy)-2-carboxamide phenyl)acetamide), indicating that its metabolic pathway involves the breakdown of nitro groups and the acetylation of the resulting amino groups.

Interactions
In 1994 and 1995, we conducted field trials in central and southern Illinois comparing several post-emergence weed control programs for soybean (Glycine max (L.) Merr.). The herbicide programs evaluated included imidacloprid, used alone or in combination with flufenoxuron (an acetolactate synthase (ALS) inhibitor), and two non-acetolactate synthase inhibitor herbicide programs: a combination of bentazon, flufenoxuron, and clethodim, and a combination of flufenoxuron, fluazinam, and phenoxypropionic acid. These treatments were administered both early post-emergence (EPOST, soybean V-1 stage - first trifoliate leaf) and post-emergence (POST, soybean V-2 stage - second trifoliate leaf). Non-acetolactate synthase inhibitor herbicide programs were generally more effective in post-emergence weed control, while imidacloprid tended to be more effective in early post-emergence weed control. In three of the four trials, post-emergence application of non-acetolactate synthase inhibitor (NSASI) herbicides was comparable to that of imazalil ethanoate (MFSI). In Brownstown in 1994, when weed growth stages were longer and environmental conditions were more extreme than in other trials, NSASI herbicides showed poor control of broadleaf weeds. In some cases, the addition of lactoferrin to imazalil ethanoate improved control of broadleaf weeds but reduced control of Setaria faberil L. The combination of imazalil ethanoate and lactoferrin often caused the greatest phytotoxicity to soybeans. This study evaluated the control efficacy of herbicide regimens containing pendimethalin and combinations of Fomesafen, fluroxypyr, and norfluronne against broadleaf weeds and Cyperus rotundus, applied alone or in combination with post-emergence MSMA or fluroxypyr + MSMA. Soil-applied herbicide combinations containing thiram showed better control of Cyperus rotundus than combinations of norfluron and fluroxypyr, but not better control of Ipomoea quamoclit, Ipomoea pubescens, Ipomoea natans, Ipomoea pubescens, or Viburnum spp.. Fluroxypyr plus methyl methacrylate (MSMA) showed better control of Ipomoea quamoclit and Viburnum spp. than MSMA. In one of the two years of fluroxypyr application, higher cotton yields were observed, which was associated with better control of Cyperus rotundus. A soybean field herbicide screening trial conducted in Lusaka Province, Zambia, aimed to evaluate the weed control effects of novel herbicides and their combinations under two cropping regimes. Weed control treatments included two control treatments (no weeding and clean weeding with a hoe), two standard treatments (methoxyfenozide + metolachlor and flufenoxuron + flupyrazole), and seven experimental herbicide/herbicide combinations (oxadiazon, oxadiazon + metolachlor, imazalil ethionyl, flufenoxuron + flupyrazole, bentazon + flupyrazole, bentazon + quizalofop-p-ethyl, and bentazon + flufenoxuron). Under conventional tillage and no-till conditions, the potential yield loss due to uncontrolled weeds was 66% and 40%, respectively. All herbicide treatments performed well under conventional tillage conditions, but under no-till conditions, none of the treatments effectively controlled weeds, especially Euphorbia and late-season weeds. The standard herbicide treatments performed well under both tillage methods. Field trials were conducted to determine the control efficacy of herbicides, alone and in combination with chlorpyrifos, imidacloprid, chlorsulfuron, and flusulfuron against rhizomatous sedge and barnyardgrass. Control rates of sedge and barnyardgrass were between 83% and 99% when applied alone. Among the sedges evaluated, clethodim showed the strongest antagonism against sedges. Clethodim, when mixed with imidacloprid, reduced sedge control by up to 64%, and when mixed with chlorsulfuron, reduced barnyardgrass control by up to 52%. Quizalofop-P-terfuran was least affected by broadleaf herbicides, while flusulfuron showed the least antagonism when mixed with sedges. For more complete data on interactions of flusulfuron (7 herbicides in total), please visit the HSDB record page.

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Non-human toxicity values
Oral LD50 in rats (male): 1860 mg/kg / flumethrin sodium /
Oral LD50 in rats (female): 1500 mg/kg / flumethrin sodium /
Dermal LD50 in rabbits: >780 mg/kg / flumethrin sodium /
Inhalation LC50 in rats (male): 4.97 mg/L /4 hr
For more complete non-human toxicity data for flumethrin (7 types), please visit the HSDB record page.

:Biomolecules. 2019 Sep 20;9(10):514.

Fomesafen is a white crystalline solid used as a herbicide. Fomesafen is an N-sulfonylformamide with the structure N-(methylsulfonyl)benzamide, where a nitro group is substituted at the 2-position of the benzene ring and a 2-chloro-4-(trifluoromethyl)phenoxy group is substituted at the 5-position. It is a protoporphyrinogen oxidase inhibitor specifically developed for post-emergence control of broadleaf weeds in soybean fields (usually used as the corresponding sodium salt, Fomesafen sodium). It has a dual role as a herbicide, agrochemical, and EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor. It is an aromatic ether, N-sulfonylformamide, C-nitro compound, organofluorine compound, monochlorobenzene compound, and phenolic compound. It is the conjugate acid of Fomesafen (1-).

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Mechanism of Action
Using soybean (Glycine max cv. Mandarin) suspension culture cell extracts as the active enzyme source, the activity order of glutathione transferases (GSTs) catalyzing the conjugation of 1-chloro-2,4-dinitrophenyl (CDNB) and selective herbicides was determined to be: CDNB > Fomesafen > metolachlor = Fomesafen > chlorimuron-ethyl. Glutathione transferase activity exhibited substrate-specific thiol dependence. Therefore, when using soybean endogenous thiol homoglutathione (hGSH) as a co-substrate instead of glutathione (GSH), glutathione transferase activity towards Fomesafen and Fomesafen was higher. Compared to glutathione, the addition of homoglutathione either reduced the activity of glutathione transferases towards other substrates or had no effect on their activity. In the absence of enzymes, the binding rates of homoglutathione to isosulfuron, chlorimuron, and flusulfanilamide were negligible, indicating that rapid homoglutathione binding in soybean must be catalyzed by glutathione transferases. Subsequently, glutathione transferase activities were measured in 14-day-old soybean plants and various annual grass and broadleaf weeds. Plant glutathione transferase activities were correlated with observed susceptibility to post-emergence application of the four herbicides. When enzyme activity was expressed on a mg-1 protein basis, all grass weeds and Abutilon theophrasti showed significantly higher glutathione transferase activities to CDNB than soybean. Using flusulfanilamide as a substrate, the order of glutathione transferase activity was: soybean (Digitaria sanguinalis) > sorghum (Sorghum halepense) = foxtail (Setaria faberi), with no activity observed in any broadleaf weeds. This order is generally consistent with the observed selectivity of Fomesafen, except for amaranth (A. theophrasti), which exhibits partial tolerance to this herbicide. Using metolachlor as a substrate, the order of glutathione transferase activity was: soybean > metolachlor > amaranth (Amaranthus retroflexus) > morning glory (Ipomoea hederacea), with no activity observed in other species. Glutathione transferase activity against metolachlor was highly correlated with the herbicide's selectivity against broadleaf weeds, but not against grassy weeds. Ethylflufenican and chlorimuron-methyl showed selective activity against these weeds, but glutathione transferase activity against these herbicides was not detected in the whole-plant crude extract.

C15H10CLF3N2O6S

438.75

437.99

72178-02-0

Fomesafen-d3

51556

White crystalline solid
White crystalline solid

1.6±0.1 g/cm3

531.4±60.0 °C at 760 mmHg

220-221°C

275.2±32.9 °C

0.0±1.5 mmHg at 25°C

1.586

3.58

1

9

4

28

693

0

CS(=O)(NC(C1=C([N+]([O-])=O)C=CC(OC2=C(Cl)C=C(C(F)(F)F)C=C2)=C1)=O)=O

BGZZWXTVIYUUEY-UHFFFAOYSA-N

InChI=1S/C15H10ClF3N2O6S/c1-28(25,26)20-14(22)10-7-9(3-4-12(10)21(23)24)27-13-5-2-8(6-11(13)16)15(17,18)19/h2-7H,1H3,(H,20,22)

5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-methylsulfonyl-2-nitrobenzamide

PP-021 PP021 Fomesafen

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~100 mg/mL (~227.92 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (5.70 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (5.70 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (5.70 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)