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Home > Encyclopedia > Fenoxaprop-ethyl

Fenoxaprop-ethyl

Fenoxaprop-ethyl structure

Fenoxaprop-ethyl 

structure
  • CAS No:

    66441-23-4

  • Formula:

    C18H16ClNO5

  • Chemical Name:

    Fenoxaprop-ethyl

  • Synonyms:

    Propanoic acid,2-[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]-,ethyl ester;Propanoic acid,2-[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]-,ethyl ester,(±)-;HOE-A 25-01;HOE 33171;Fenoxaprop-ethyl;Furore;Whip;Fenoxaprop ethyl ester;Acclaim;Ethyl 2-[4-(6-chlorobenzoxazolyl-2-oxy)phenoxy]propionate;(±)-Fenoxaprop-ethyl;Acclaim (herbicide);116573-18-3;82110-72-3;87714-45-2

  • Categories:

    Agrochemicals  >  Herbicides

Description

Colorless or white solid. Liquid form is darkbrown with an aromatic hydrocarbon odor.


Coarse light beige to brown powder. Selective herbicide.


Coarse light beige to brown powder. Selective herbicide.|Fenoxaprop ethyl is an aromatic ether.|Fenoxaprop-ethyl (organic nitrate combined with L-arginine), is an oral proprietary nitrate therapeutic shown to induce coronary vasodilation while overcoming the significant problem of drug tolerance. Fenoxaprop-ethyl has been investigated to treat chronic angina, the chest pain that occurs from inadequate blood flow to the coronary arteries around the heart.

Fenoxaprop-ethyl Basic Attributes

361.78

361.78

266-362-9

3077

DTXSID2032392

Colorless solid

2934999023

Characteristics

70.79000

4.60390

1.31g/cm3

84-85 °C

200 °C @ Press: 0.750 Torr

242.6ºC

1.587

Solubility @ 20 deg c: >0.5% in hexane; >1% in cyclohexane, ethanol, 1-octanol; >20%in ethyl acetate; >30% in toluene; >50% in acetone; solubility in water @ 25 deg C: 0.9 mg/l

-20°C

0.19 X 10-5 Pa @ 20 deg C

LD50 in male, female rats (mg/kg): 2357, 2500 orally; 739, 864 i.p. (Bieringer)

No rapid reaction with air. No rapid reaction with water.

Amines, Phosphines, and Pyridines

Safety Information

UN30779/PG3

2

43-50/53-22

24-37-60-61

UA2454000

Xi,N,Xn

P273-P280-P501

H317-H410

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)

|Warning|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, and P501|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|Wear goggles or face shield and impermeable rubber gloves while mixing. Long sleeved shirt and long pants while mixing and during application.

Dry chemical or carbon dioxide for small fires. Foam or water for large fires.

Avoid inhalation of vapor or spray mist. Remove contaminated clothing and wash before reuse. Wash thoroughly with soap and water after handling. Handle only in ventilated area.

Toxicity

LD50 Mouse male oral 4670 mg/kg|LD50 Mouse female oral 5490 mg/kg|LD50 Rat male oral 2357 mg/kg|LD50 Rat female oral 2500 mg/kg

The persistence of (14)C fenoxaprop acid, the major degradation product of the herbicide (14)C fenoxaprop-ethyl, was studied at different controlled temperature and moisture conditions in 3 Sakatchewan soils. At 85% of field capacity, degradation approximated to first order kinetics at soil temperatures of 10, 20, and 30 °C, with halflife values ranging from 42 to 5 days. In clay at 20 °C, there was no effect of moisture, between 50 and 100% field capacity, on the rate of (14)C fenoxaprop acid breakdown. There was no loss of radioactivity after 65 days in air dry soils. In all soils incubated at 85% field capacity and 20 °C with (14)C fenoxaprop-ethyl, uniformly labeled in the chlorophenyl ring, there was evolution of (14)CO2 indicating ring fission. Over a 56 day incubation period, 10-15% of the applied radioactivity was released from the treated soils as (14)CO2. Extraction with ammoniated acetonitrile recovered 14-19% of the original radioactivity; between 3 and 5% of the initial (14)C was incorporated into soil microbial biomass, 17-25% into the fulvic acid, 7-12% into the humic acid, and 30-34% into the humin soil fractions.|The environmental persistence and fate of fenoxaprop-ethyl, a herbicide proposed for selective control of grasses in California rice, have been investigated under laboratory and field conditions. In the field, it dissipated rapidly from both water and soil, with half lives in water <4 hr and soil residues belo detectability within 6 days. The photolysis half life in sterile, distilled water was 269 hr; in field water a combination of microbial and photochemical reactions resulted in a half life of 29 hr. Products included the corresponding acid, 6-chlorobenzoxazolinone, ethyl 2-(4-hydroxyphenoxy)propanoate, and 2-(4-hydroxyphenoxy)propanoic acid. Hydrolysis was slower at pH 6.1 and 7.4 but resulted in a half life of only 8.3 hr at pH 9.1. Fenoxaprop-ethyl is essentially nonvolatile (Henry's Law constant = 3X10-7) and was bound moderately to soil (Kcc = 6800). These properties represent a near optimum for pesticide persistence.

9.55e+03 L/kg

Drug Information

Chronic angina and Coronary Artery Disease

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)

Dermal absorption of the (14)C ring-labelled herbicide fenoxaprop-ethyl was examined after topical applications of the herbicide in either acetone or in field formulation (Excel) to the shaved backs of rats (n= 6) according to standard in vivo procedure. The total percentage dermal absorption was determined from the mean percentage recoveries of (14)C in the urine after correction for incomplete urinary excretion using the recovery figures obtained from im dose studies (49:17.7% recovery). The mean percentage dermal absorption of fenoxaprop-ethyl applied in acetone at a dose of 1.8 ug/sq cm was 32:6.8% and was significantly greater than that obtained at the same dose of fenoxaprop-ethyl applied in the Excel formulation (18:4.5%). Increasing the applied dose of fenoxaprop-ethyl had no effect on dermal absorption within the dose range 1.8 to 100 ug/sq cm; when doses of 10 and 100 ug/sq cm were applied in Excel, 20:6.7% and 21:4.5% was absorbed, respectively. Mass balance studies with the total percentage recovery in urine (im corrected) added to recovery from foam patches covering the dose site, and from gauze swabs moistened with soapy water taken of dosed skin 24 hr after treatment, demonstrated only 56:3.7%, 54:3.8%, 56:5.4% and 53:3.9% total recovery for the acetone 1.8 ug/sq cm and Excel 1.8, 10 and 100 ug/sq cm treatments, respectively. Significantly less residual (14)C activity was detected in the skin swabs taken for the acetone (8:3.5%) than for the Excel treatments (21:6.0%, 27:4.0% and 25:5.8% for the 1.8, 10 and 100 ug/sq cm dose rates, respectively). Comparative studies conducted at a dose rate of 1.4 ug/sq cm with automated in vitro dermal absorption procedure demonstrated no significantly different total percentage dermal absorption in dermatomed skin taken from the same rats tested in vivo at a dose rate of 1.8 ug/sq cm. There was no significant difference between the total percentage dermal absorption obtained for automated in vitro dermal absorption analysis of fresh rat skin (27:9.3%; n= 20) compared with that for rat skin frozen for 7 days in liquid nitrogen (25:7.6%; n= 19).

Fenoxaprop-ethyl is a proprietary combination of nitrate and L-arginine that provides the beneficial cardiovascular effects of nitrates. Combining L-arginine with organic nitrates prevents the endothelial cell's depletion of L-arginine and the associated problem of nitrate tolerance. By eliminating nitrate tolerance, Fenoxaprop-ethyl allows patients to receive the continuous, 24-hour benefit of a potent nitrate product, thus sustaining the desired vasodilation effect.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. (ERG, 2016)

ethyl 2-(4-((6-chloro-2-benzoxazolyl)oxy)phenoxy)propanoate

Fenoxaprop-ethyl Use and Manufacturing

Methods of Manufacturing

Preparation method 1: Preparation of 2-(4-acetophenoxy) ethyl propionate In the dimethylformamide (DMF) solution of 4-hydroxyacetophenone potassium salt (25g), add 2-chloropropane after 30 minutes Ethyl acid (27.3g), under nitrogen, stirred at 85-90 for 3h, filtered to remove KCl, removed DMF under reduced pressure, dissolved in ethyl acetate, extracted with alkali and water, dried and concentrated to obtain 30g 2- (4-Acetylphenoxy) ethyl propionate. Preparation of 2-(4-acetoxyphenoxy) ethyl propionate At 58℃, 8×10-3Pa, 30min, add peracetic acid (16%, 15.61g, 33.0mmol) and acetic acid (50mL) dropwise In equilibrium, ethyl 2-(4-acetylphenoxy)propionate (5.01g, 21.0mmol) solvent. At 48~54℃t 7×103~8×103Pa, the reaction was refluxed for 8h, cooled, and the acetic acid was removed under reduced pressure to obtain 5.34g ethyl 2-(4-acetoxyphenoxy)propionate. Preparation of 2-(4-hydroxyphenoxy) ethyl propionate At 80℃, use ethanol (40 mL) and 2 drops of concentrated hydrochloric acid to reflux 2-(4-acetoxyphenoxy) ethyl propionate for 2 hours After hydrolysis, the reactant was concentrated under reduced pressure to obtain ethyl 2-(4-acetoxyphenoxy) propionate under reflux for 2 hours for hydrolysis. The reactant was concentrated under reduced pressure to obtain ethyl 2-(4-hydroxyphenoxy) propionate. Esters (3.8g). The synthesis of fenoxaprop-p-ethyl Add 2 g of potassium carbonate to a solution of ethyl 2-(4-hydroxyphenoxy) propionate (2.0 g, 9.8 mmol) in acetonitrile (25 mL), and reflux for 1 h. The reaction was cooled, 2,6-dichlorobenzoxazole (1.8g, 10.2mmol) was added, the reaction was refluxed for 4h, and concentrated to dryness. Acetonitrile (50 mL) was added to the reaction mixture. Reflux for 2h, hot filter, concentrate to 25mL, and cool to obtain oxfenprop-p-ethyl 2.9g.

Uses

Used to control annual, perennial monocotyledonous weeds in dicotyledonous crop fields such as soybean, cotton and sugar beet

Emulsifiable concentrate

Selective postemergent herbicide

Computed Properties

Molecular Weight:361.8
XLogP3:4.1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:7
Exact Mass:361.0717003
Monoisotopic Mass:361.0717003
Topological Polar Surface Area:70.8
Heavy Atom Count:25
Complexity:443
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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