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Isoxaben

Isoxaben structure

Isoxaben 

structure
  • CAS No:

    82558-50-7

  • Formula:

    C18H24N2O4

  • Chemical Name:

    Isoxaben

  • Synonyms:

    Benzamide,N-[3-(1-ethyl-1-methylpropyl)-5-isoxazolyl]-2,6-dimethoxy-;N-[3-(1-Ethyl-1-methylpropyl)-5-isoxazolyl]-2,6-dimethoxybenzamide;Isoxaben;EL 107;NA 8318;Benzamizole;Flexidor;Gallery;X-Pand;Cent 7

  • Categories:

    Agrochemicals  >  Herbicides

Description

ChEBI: A benzamide obtained by formal condensation of the carboxy group of 2,6-dimethoxybenzoic acid and the amino group of 3-(3-methylpentan-3-yl)-1,2-oxazol-5-amine.


Isoxaben is a benzamide obtained by formal condensation of the carboxy group of 2,6-dimethoxybenzoic acid and the amino group of 3-(3-methylpentan-3-yl)-1,2-oxazol-5-amine. It has a role as a herbicide and a cellulose synthesis inhibitor. It is a member of isoxazoles and a member of benzamides.

Isoxaben Basic Attributes

332.39

332.39

407-190-8

101V41EEA4

DTXSID8024159

White crystalline solid|Light tan granule

Characteristics

73.6

3.94 at 25 deg C

1.138g/cm3

177.5 °C

427.8ºC at 760 mmHg

212.6ºC

1.544

In water, 1.42 mg/L at pH 7 and 20 deg C

0-6°C

4.13X10-9 mm Hg at 25 deg C

Mild aromatic odor

Henry's Law constant = 1.27X10-9 atm-cu m/mol at 25 °C (calc)

184.93 Ų [M+H]+ [CCS Type: TW]|188.99 Ų [M-H]-

Hydroxy radical reaction rate constant = 2.0X10-10 cu cm/molec-sec at 25 °C (est)

Safety Information

NONH for all modes of transport

3

53-40

61-36

CV4370300

Xn

Stable to hydrolysis at pH 5-9. Susceptible to photodegradation in aqueous solution.

P273, P501

H413

Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.|Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.|SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

H413: May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]|P273, and P501|H413 (100%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]|Aggregated GHS information provided by 194 companies from 1 notifications to the ECHA C&L Inventory.| |Warning|H400 (98.21%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|Aggregated GHS information provided by 56 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P264, P280, P281, P302+P352, P305+P351+P338, P308+P313, P321, P332+P313, P337+P313, P362, P405, and P501

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.|After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.

/For applying the product/ wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.|Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Isoxaben has been found in the runoff water from containerized plant production facilities 4 days after application. The other pesticides in this study, trifluralin, chlorpyrifos and thiophanate methyl, were primarily only detected on the day of application(1).

Toxicity

LD50 Rat oral >10 000 mg/kg|LD50 Mouse oral >10,000 mg/kg|LD50 Dog oral >5000 mg/kg|LD50 Rabbit dermal >2000 mg/kg|For more Non-Human Toxicity Values (Complete) data for ISOXABEN (7 total), please visit the HSDB record page.

Isoxaben's production may result in its release to the environment through various waste streams; it's use as a herbicide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3,300(SRC), determined from a log Kow of 3.94(2) and a regression-derived equation(3), indicates that isoxaben is expected to have slight mobility in soil(SRC). Volatilization of isoxaben from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 1.27X10-9 atm-cu m/mole(2). Isoxaben is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Reported half-lives of isoxaben in soil range from 2.07 to 6.6 months with the largest half-lives noted in soils treated with various fertilizers such as green manure, cow manure and pig slurry: 4.03, 4.75 and 6.6 months, respectively(4). The main biodegradation metabolite of isoxaben was demethoxyisoxaben(5). When applied to soil at rates of 0.56, 0.84, and 1.12 kg/hectare, 50% of isoxaben remained after 3 months, 6 months, and 3 months, respectively(6).|TERRESTRIAL FATE: Isoxaben's half-life in soils that were previously treated with the insecticide were about half of the that of soil not previously treated with the insecticide. Of 5 soils from pear tree orchards in Europe used in a field study, only 2 had previously been treated with isoxaben. Isoxaben half-life in the 3 soil samples that had been treated with other pesticides ranged from 2.7-6.1 months(1). Isoxaben has been found in the runoff water from containerized plant production facilities 4 days after application. The other pesticides in this study, trifluralin, chlorpyrifos and thiophanate methyl were primarily only detected on the day of application(2).|TERRESTRIAL FATE: In winter wheat fields treated with isoxaben from 1990-1991 and 1991-1992 the main metabolite detected was demethoxyisoxaben and appeared in the soil within 34-41 days after treament. It was found in the soil after 282 days(1). The second main isoxaben metabolite found in the soil was 5-aminoisoxazole which appeared within 83 days of treatment. The products did not accumulate in the soil. Isoxaben in concentrations ranging from 9-16% of the concentration found on day 3 was still found in the soil after 282 days after treatment(1).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3,300(SRC), determined from a log Kow of 3.94(2) and a regression-derived equation(3), indicates that isoxaben is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 1.27X10-9 atm-cu m/mole(2). According to a classification scheme(4), an estimated BCF of 215(SRC), from its log Kow(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Biodegradation data on isoxaben in water were not located; however based on data from soil studies(6-8), isoxaben may biodegrade slowly in aquatic environments(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isoxaben, which has a vapor pressure of 4.13X10-9 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase isoxaben may be removed from the air by wet and dry deposition(SRC). Aqueous solution of isoxaben have be shown to be susceptible to photodegradation(2).

Isoxaben is not expected to undergo hydrolysis in the environment due to the lack of functional groups that would hydrolyze under environmental conditions(1). Aqueous solutions of isoxaben have be shown to be susceptible to photogradation(2).

An estimated BCF of 215 was calculated for isoxaben(SRC), using a log Kow of 3.94(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).

251.19 L/kg|The Koc of isoxaben is estimated as 3,300(SRC), using a log Kow of 3.94(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that isoxaben is expected to have slight mobility in soil.

The Henry's Law constant for isoxaben is 1.27X10-9 atm-cu m/mole(1). This Henry's Law constant indicates that isoxaben is expected to be essentially nonvolatile from moist soil and water surfaces(SRC). Isoxaben is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Occupational exposure to isoxaben may occur through dermal contact with this compound at workplaces where isoxaben is produced or used. The most likely route of exposure to the general public is through dermal contact with soil treated with this compound, a herbicide. (SRC)

Drug Information

In rats, following oral administration, 90% is excreted in the feces within 48 hours; about 10% of the absorbed isoxaben undergoes conversion into about 15-20 metabolites, which are excreted in the urine. There is no accumulation of either parent or metabolites in cell tissue.

The product typically contains about 2% of an isomer N-(3-(1,1-dimethylbutyl)-5-isoxazolyl)-2,6-dimethoxybenzamide.

Carcinogens

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

EL 107

Isoxaben Use and Manufacturing

Methods of Manufacturing

Preparation: K.W. Burow, GB 2084140; ... idem, US 4636243 (1982, 1987 both to Lilly)

Uses

Isoxaben is used primarily for preemergence control of annual broadleaf weeds. Isoxaben is usually applied to soil either with light incorporation or before application of water (at least 0.5 in) within 3 weeks. As is the case with DCB, it is most effective on weed seedlings before emergence.

Dry flowable, suspension concentrate.|Discontinued products: Snapshot|Trade Names: Flexidor, El 107.

For winter barley, wheat, rye and oats, non-phytotoxic at the recommended application rates. Some rotational crops may be injured if planted immediately following the treated crop.

Product and residue analysis by hplc with ultraviolet detection.

Agrochemicals -> Herbicides|Health Hazards -> Carcinogens|Herbicides

Computed Properties

Molecular Weight:332.4
XLogP3:3.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:332.17360725
Monoisotopic Mass:332.17360725
Topological Polar Surface Area:73.6
Heavy Atom Count:24
Complexity:402
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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