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Bensulide

Bensulide structure

Bensulide 

structure
  • CAS No:

    741-58-2

  • Formula:

    C14H24NO4PS3

  • Chemical Name:

    Bensulide

  • Synonyms:

    Phosphorodithioic acid,O,O-bis(1-methylethyl) S-[2-[(phenylsulfonyl)amino]ethyl] ester;Phosphorodithioic acid,O,O-diisopropyl ester,S-ester with N-(2-mercaptoethyl)benzenesulfonamide;R 4461;Bensulide;Betasan;N-[2-(O,O-Diisopropyldithiophosphoryl)ethyl]benzenesulfonamide;Disan (pesticide);Prefar;S-β-(Benzenesulfonamido)ethyl O,O-diisopropyl dithiophosphate;Disan;O,O-Diisopropyl 2-(benzenesulfonamido)ethyl dithiophosphate;SAP (herbicide);SAP;O,O-Diisopropyl S-(2-benzenesulfonylaminoethyl) phosphorodithioate;39291-71-9

  • Categories:

    Agrochemicals  >  Herbicides

Description

Colorless liquid; slight odor.Insoluble in water; soluble in kerosene and xylene. Bensulide is and amber, viscous liquid, or forms colorless or white crystalline solid below 34.4 C. Combustible. Commercial product is available as an emulsifiable concentrate.


COLOURLESS-TO-WHITE CRYSTALS.


Bensulide is a member of benzenes.

Bensulide Basic Attributes

397.51

397.51

212-010-4

9882BW2Q2S

0383

2783

DTXSID9032329

Colorless solid|Colorless liquid or white crystalline solid|Amber solid or super cooled liquid /technical formulation/

29350090

Characteristics

130

4.22

White Solid

1.23 g/cm3 @ Temp: 20 °C

34.4 °C

487.2ºC at 760 mmHg

315 deg F, 157 deg C (Open cup)

1.557

Solubility in water, g/100ml at 20°C: 0.0025

2-8°C

Vapour pressure, Pa at 20°C:

Oral-rat LD50: 271 mg/kg; Oral-Mouse LD50: 1540 mg/kg

Decompose toxic phosphorus oxide, sulfur oxide, nitrogen oxide gas by heating

Characteristic camphor-like odor

Henry's Law constant = 1.7X10-8 atm-cu m/mol at 25 °C (est)

195.17 Ų [M+Cl]-

Hydroxyl radical reaction rate constant = 1.7X10-10 cu cm/mole-sec at 25 °C (est)

Corrosive to copper, but not to mild iron, steel, tin, or brass.

Safety Information

UN28116.1/PG3

3

22-50/53

24-36-60-61

TE0250000

Xn,N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Bensulide is stable at 80 deg C for 50 hr, but decomposes at 200 deg C in 18 to 40 hr.

P273-P301 + P312 + P330-P391-P501

H302-H410

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

USEPA/Office of Prevention, Pesticides and Toxic Substances; Interim Reregistration Eligibility Decision Document - Bensulide EPA 738-R-00-002 (June 2000). EPA issues an IRED for a pesticide that is undergoing reregistration, requires a reregistration eligibility decision, and also needs a cumulative assessment under FQPA. The IRED, issued after EPA completes the individual pesticide's aggregate risk assessment, may include taking risk reduction measures -- for example, reducing risks to workers or eliminating uses that the registrant no longer wishes to maintain -- to gain the benefits of these changes before the final RED can be issued following the Agency's consideration of cumulative risks.[Available from, as of January 31, 2017: http://www.epa.gov/pesticides/reregistration/status.htm]|California Environmental Protection Agency/Department of Pesticide Regulation; Summary of Toxicology Data, Bensulide, Chemical Code No.70 (August 10, 1998, Revised March 26, 2001). Provides a summary of available toxicological information for pesticides currently or previously registered for use in California.[Available from, as of January 31, 2017: http://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm]|USEPA; Bensulide: Health Effects Division's Chapter for the Reregistration and Eligibility Decision Document. Washington, DC: USEPA, Off Pest Prog. March 3, 1998. This paper includes the Hazard Assessment, the Product and Residue Chemistry Assessments, the Occupational and Residential Exposure Assessment, the Incidence Reports Data, the Dietary Risk Analysis, and the Drinking Water Exposure Data for inclusion in the Bensulide Reregistration Eligibility Decision.[Available from, as of March 11, 2003: http://www.epa.gov/pesticides/op/bensulide/bensuhed.pdf]

Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 130 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Use water spray, powder, foam, carbon dioxide.

Fire point: 171 °C

Avoid contact with eyes and skin and inhalation of spray mists. Guard against drift.|SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

/GUIDE 131 FLAMMABLE LIQUIDS - TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|/GUIDE 131 FLAMMABLE LIQUIDS - TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|/GUIDE 131 FLAMMABLE LIQUIDS - TOXIC/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind, uphill and/or upstream. Ventilate closed spaces before entering. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|/GUIDE 131 FLAMMABLE LIQUIDS - TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|For more DOT Emergency Guidelines (Complete) data for Bensulide (16 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials. Organophosphorus pesticide, solid, toxic; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, toxic, flammable; and Organophosphorus pesticide, liquid, toxic are included on the dangerous goods list. /Organophosphorus pesticide, solid, toxic; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, toxic, flammable; and Organophosphorus pesticide, liquid, toxic/|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article. /Organophosphorus pesticide, solid, toxic; Organophosphorus pesticide, liquid, flammable, toxic, flashpoint less than 23 °C; Organophosphorus pesticide, liquid, toxic, flammable, flashpoint not less than 23 °C; and Organophosphorus pesticide, liquid, toxic are included on the dangerous goods list. /Organophosphorus pesticide, liquid, flammable, toxic, flashpoint less than 23 °C; Organophosphorus pesticide, liquid, toxic, flammable, flashpoint not less than 23 °C; and Organophosphorus pesticide, liquid, toxic/

Mild skin and eye irritant (rabbits)

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT wash away into sewer. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.

The substance may cause effects on the nervous system. This may result in convulsions and respiratory failure. Cholinesterase inhibition. Exposure could cause death. The effects may be delayed. Medical observation is indicated.

Cholinesterase inhibition. Cumulative effects are possible. See Acute Hazards/Symptoms.

NO open flames.

PREVENT DISPERSION OF DUST! AVOID EXPOSURE OF ADOLESCENTS AND CHILDREN!

Use local exhaust or breathing protection.

Protective gloves.

Wear safety spectacles.

URBAN/SUBURBAN: An application rate for bensulide of 6730 g/ha to bentgrass greens and fairways was reported for April 15 and June 15, year not provided. Using this data annual volatilization of bensulide from three golf courses located in Boston, Philadelphia, and Rochester as a percent of annual application was simulated as 0.55%, 0.69% and 0.55%, respectively. Maximum and average concentrations of bensulide were simulated at the three golf courses located in Boston, Philadelphia, and Rochester were reported as 2.9X10-2 and 6.8X10-4 ug/m cu, 4.5X10-2 and 1.1X10-3 ug/m cu, and 3.9X10-2 and 8.8X10-4 ug/m cu, respectively(1).

Bensulide was not detected in Pacific salmonid habitats monitored as part of California's surface water monitoring results from 1991 through 2010(1).

Toxicity

highly toxic

IDENTIFICATION AND USE: Bensulide is a viscous amber liquid above 34.4 °C, and a solid below that temperature. It is used for pre-emergence control of annual grasses and broad-leaved weeds in established turf, dichondra, brassicas, cucurbits, watermelons, cotton, lettuce, tomatoes, carrots, capsicums, rice, and herbage seed crops. HUMAN STUDIES: No data. ANIMAL STUDIES: Bensulide is a cholinesterase inhibitor and mild irritant in rabbit eyes. Rats tolerated 1 hr exposures to 8 mg/L air. In 90 day feeding trials, no-effect level for rats was 25 mg/kg/day, for dogs 2.5 mg/kg/day, and for mice 30 mg/kg/day. In a chronic toxicity study in dogs, bensulide (92.4% a.i.) was administered to 4 dogs/sex/dose by feeding at dose levels of 0, 0.5, 4, or 30 mg/kg/day for 52 weeks. No neoplastic tissue was observed in dogs in the treatment and control groups. Chronic toxicity in rats receiving 60 mg/kg/day was characterized in both sexes by reduced cholinesterase levels in plasma, erythrocytes, and brain, and, in the males, by increased absolute liver weights and mild histopathological changes of the liver (hepatocyte vacuolation and eosinophilic foci). In the 15 mg/kg/day animals, reduced plasma and erythrocyte cholinesterase activities were also observed. In developmental toxicity studies bensulide exerted no effects on maternal gross pathology, fertility, or cesarian parameters and the lack of any developmental effects. Bensulide was not mutagenic when evaluated for its ability to induce point mutations in the T4 bacteriophage/Escherichia coli B system. ECOTOXICITY STUDIES: Bensulide was toxic to fish and inhibited germination in grasses.

LD50 Rat (male) oral 360 mg/kg|LD50 Rat (female) oral 270 mg/kg|LD50 Rat percutaneous >2000 mg/kg|LC50 Rat inhalation >8.0 mg/L (1 hr)|For more Non-Human Toxicity Values (Complete) data for Bensulide (9 total), please visit the HSDB record page.

/AQUATIC SPECIES/ A scan of the acute toxicities of eighteen common herbicides to one-year-old channel catfish (Ictalurus punctatus) was conducted. Herbicides causing less than 10% mortality in 48 hr at 10 ppm were: alanap, chloramben, 2,4-D acid, 2,4-D dimethyl amine salt, dalapon, diuron, DSMA, EPTC, fluometuron, metribuzin, monuron, MSMA, nitralin and 2,4,5,-T. The 96-hr LC50 values in pp6 for four nerbicides found toxic were: propanil, 3796; trifluralin, 417; bensulide, 379; and DNBP 118. The toxicity of Dyanap, a mixture of DNBP and alanap, was lower than that of DNBP; there was no apparent synergism between DNBP and alanap in the mixture.|/PLANTS/ Oat seedlings were grown by two different methods in various concentrations of bensulide. Root growth was inhibited, the roots were sometimes curved and root hairs were often present close to the root tip. Structural features of the treated roots included epidermal cells which were greatly elongated radially; short, pitied trachcary elements differentiated close to the root tip; and occasional lesions. One of the primary effects of bensulide appears to be inhibition of root growth, though it does not completely inhibit mitosis.|/PLANTS/ Inhibits germination in grasses.|/PLANTS/ It inhibits the growth of roots of weeds.|/PLANTS/... Pepper, watermelon, cotton, lettuce, tomato and carrot were tolerant to concn of <1,000 ppm bensulide in fine sandy loam soil. Cabbage and onion were tolerant to bensulide levels of 725 ppm or less.

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

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 1,000(2) indicates that bensulide is expected to have low mobility in soil(SRC). Volatilization of bensulide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.7X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 8.0X10-7 mm Hg(3), and water solubility, 25 mg/L(4). Bensulide is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Bensulide is considered persistent in soils due to its very slow degradation, achieving 75-100% reduction of applied amounts after 5 months(5); therefore, biodegradation is a slow environmental fate process in soil(SRC).|FIELD STUDY: In a field study of agricultural soils, the half-life values of bensulide were 44.3, 37.6, and 27.1 days in sewage sludge-yard waste, sewage sludge, and unamended soils, respectively. With the addition of sewage sludge-yard waste and sewage sludge to the native soil increases in water infiltration were observed, lowering run-off water volume and bensulide residues in run-off following natural rainfall events(1).|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 1000(2), indicates that bensulide may adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.7X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 8.0X10-7 mm Hg(4), and water solubility, 25 mg/L(5). According to a classification scheme(6), a BCF of 880(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Bensulide's persistence in soil(8) would suggest that biodegradation may be a slow aquatic environmental fate process(SRC). Bensulide has a reported hydrolysis half-life of 9.9 days(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bensulide, which has a vapor pressure of 8.0X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase bensulide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.3 hours(SRC), calculated from its rate constant of 1.7X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase bensulide may be removed from the air by wet and dry deposition(SRC). It is reported that bensulide decomposes slowly in light(5).

The rate constant for the vapor-phase reaction of bensulide with photochemically-produced hydroxyl radicals has been estimated as 1.7X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). As a class, hydrolysis of organophosphate esters can occur by direct nucleophillic attack at the phosphorous atom(3). Bensulide is considered relatively stable to acids and alkalis and has a reported hydrolysis half-life of 9.9 days(4,5). It is reported that bensulide decomposes slowly in light(5). The P=S moiety of bensulide has been reported to undergo photo-induced oxidation using UV irradiation(6).

Following an EPA guideline study, a whole body BCF of 880 was reported for bensulide in bluegill fish (Lepomic macrochirus) exposed for 28 days(1). According to a classification scheme(2), this BCF suggests bioconcentration in aquatic organisms is high(SRC)).

1.00e+03 L/kg|The Koc of bensulide is reported as 1,000(1). Laboratory studies using four soils resulted in Koc values ranging from 1,433 to 4,326(2). Main degradates of bensulide were found to be moderately to highly mobile in the same four soils(2). According to a classification scheme(3), this Koc data suggests that bensulide is expected to have low to no mobility in soil. Bensulide applied to soil was shown to have a pesticide leaching potential, which relates soil half-life, application rate, and Koc, of 54 at pH 7 and 39 at pH 5(4), suggesting moderate and low potential for contaminating groundwater, respectively(5).|Bensulide, applied as a 50% emulsifiable concentrate (1.5 g), did not leach to any great extent in lysimeter experiments set in an experimental field in Ibaraki prefecture in Japan, designed to simulate a putting green(1). However, when applied to Panoche loam for 5-6 yrs as soil-incorporated broadcast sprays directed at the base of cotton at last cultivation, bensulide residues were detected below the till zone; it was not detected one yr after final treatment(2).

The Henry's Law constant for bensulide is estimated as 1.7X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 8.0X10-7 mm Hg(1), and water solubility, 25 mg/L(2). This Henry's Law constant indicates that bensulide is expected to be essentially nonvolatile from water surfaces(3). Bensulide's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Bensulide is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

GROUNDWATER: Bensulide was not detected in 191 groundwater samples collected in the US between 1971-1991(1); the compound is not expected to migrate into groundwater based on it's high soil sorption affinity(2). Water quality data compiled from the Retrieval (STORET) Data Warehouse report 2014 and 2015 monitoring data from the Minnesota Department of Agriculture - Pesticide Monitoring program indicating that bensulide was not detected in ground water samples(3).|SURFACE WATER: Bensulide was applied as a 50% emulsifiable concentrate (1.5 g) to two golf course fairways in Ibaraki prefecture in Japan(1). Surface water concentrations were 2,624, 1,353, and 786 ppb 3, 10, and 38 days after application, respectively, for one fairway and 2,156 and 992 ppb 3 and 10 days after application, respectively, for a second fairway(1). Differences in concentrations between the 2 surface water samples were attributed to differences in distances between application and collection sites(1). Water quality data compiled from the Retrieval (STORET) Data Warehouse report 2014 and 2015 monitoring data from the Minnesota Department of Agriculture - Pesticide Monitoring program indicating that bensulide was not detected in surface water samples(2).

Bensulide was tested for but not detected, limit of quantitation = 0.1 ppm, in domestic and imported pears and tomatoes(1). A total of 129,524 lbs active ingredient bensulide/yr were applied to 29% of the watermelon crop in the US during 1987/89(2). Bensulide residues have not been detected in dietary field trials(3).|In FDA total diet studies analyzing foods for human consumption as part of the pesticide monitoring program during the fiscal year 2013, bensulide was not listed for inclusion in the study; during the fiscal years 2009 through 2012 bensulide was listed as a pesticide in the monitoring program although it was not detected in the foods studied(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 4003 workers (none of these are female) were potentially exposed to bensulide in the US(1). The NOES Survey does not include farm workers. Occupational exposure to bensulide may occur through inhalation and dermal contact with this compound at workplaces where bensulide is produced or used. The greatest potential for workers exposure to bensulfide is expected for individuals who are directly involved with mixing, loading, and application of bensulide. Use data indicate that the general population may be exposed to bensulide via inhalation and dermal contact with consumer products containing bensulide. Exposure is expected to be greatest for people who are frequently in areas where this herbicide is used (i.e. agricultural sites, golf courses and home lawns)(SRC).

Drug Information

Selective herbicide, adsorbed on the root surfaces, and a small amount is absorbed by the roots. Translocation of bensulide to the leaves does not occur, but metabolites are translocated.|In a metabolism study, bensulide technical, labelled with C in the 14 phenyl ring (> 96.4% radiopurity; 925 MBq/mMole) was dissolved in corn oil (vehicle) and administered to Sprague-Dawley rats (5/sex/group; 7-8 weeks of age; 185-235 g body weight) following 3 treatment regimes. Animals in Group I received a single oral dose of radioactive bensulide at 1 mg/kg bw. Animals in Group II received 14 consecutive doses (1 mg/kg/day) of non-radioactive bensulide technical (99% a.i.) in corn oil, followed by a 1 mg/kg dose of radiolabelled bensulide technical in corn oil on day 15. Group III animals received a single oral dose of radiolabelled bensulide technical at 100 mg/kg bw. An additional group of animals (Group IV; 3/sex/group) were given a single oral dose of radiolabelled bensulide 18 technical at 1 mg/kg bw and were subseqently used for autoradiological radiolabelled carbon dioxide release determinations. ... In Group I, total urinary excretion of 7 days after admin of radioactive bensulide technical accounted for 70 and 75% of the administered dose in males and females, respectively. ... In Group III, total urinary excretion accounted for 75 and 87% of the administered dose in males and females, respectively. ... For Group II (prior 14-day admin of non-radioactive bensulide technical before radioactive bensulide admin, both at 1 mg/kg), total urinary excretion of radioactivity over 7 days past dosing with radioactive bensulide accounted for 79 and 88% of the administered dose in males and females, respectively. For Group IV, urinary excretion of 14-C radioactivity derived from bensulide technical over a 48-hr period accounted for 67% for one male and 86% in one male. For Group I, total fecal excretion of radioactivity derived from 14C-bensulide technical over 7 days post-dosing accounted for 22 and 20% of the administered dose in males and females, respectively. ... For Group III, total fecal elim over 7 days post-dosing of bensulide-derived radioactivity accounted for 22 and 11% of the administered dose for males and females, respectively. ... In Group II animals, total fecal excretion of radioactivity over 7 days post-dosing accounted for 14 and 8% of the administered dose for males and females, respectively. ... In Group IV, fecal excretion of radioactivity over 48 hrs post-dosing accounted for 12% of the administered dose in one male and 7% in one female. ... The radioactivity found in the carcasses and in other tissues accounted for 0.3% to 2.5% and <0.1% of the administered dose, respectively.

Unchanged ring-labelled (14)-C bensulide could be detected in roots of lettuce plants after root application ... . A large part of the radioactive material in the leaves was evolved as radioactive carbon dioxide and some was present as labelled amino acids.

Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organophosphates and related compounds/|/SRP:/ Basic Treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway if needed). Suction if necessary. Aggressive airway control may be needed. Watch for signs of respiratory insufficiency and assist ventilations if necessary. 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 0.9% saline (NS) 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. Administer activated charcoal ... . /Organophosphates and related compounds/|/SRP:/ Advanced Treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/ Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously and consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer atropine. Correct hypoxia before giving atropine ... . Administer pralidoxime chloride (2-PAM). UNDER DIRECT PHYSICIANS ORDER ... . Treat seizures with adequate atropinization and correction of hypoxia. In rare cases diazepam (Valium) or lorazepam (Ativan) may be necessary ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organophosphates and related compounds/|Exposure to active ingredient (ai) may cause cholinesterase inhibition. Atropine by injection is antidotal. 2-PAM is also antidotal when administered early and in conjunction with atropine. Never use morphine.|For more Antidote and Emergency Treatment (Complete) data for Bensulide (18 total), please visit the HSDB record page.

bensulide

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

Pupillary constriction. Excessive salivation. Lacrimation. Urination. Diarrhoea. Shortness of breath. Muscle cramps. Unconsciousness.


MAY BE ABSORBED! Itching. Rash. Redness. Pain. Further see Inhalation.


Redness. Pain. Further see Inhalation.

Bensulide Use and Manufacturing

Methods of Manufacturing

... A mixture of 13.2 grams (0.06 mol) of N-(beta-chloroethyl)-benzene sulfonamide, 25.2 grams (0.1 mol) of potassium-diisopropyl dithiophosphate and 100 ml of methyl ethyl ketone yielded after 4 hour reflux period, 20.8 grams (88% theory) of viscous product.|Bensulide is produced by reaction of O,O-diisopropylphosphorodithioate with N-chloroethylbenzene sulfonamide.

Uses

Herbicide. Bensulide is an herbicide used for preemergent control of annual grasses and broadleaf weeds in agricultural crops (60–65% of all use). Current registered use sites are carrots, fruiting vegetables, leafy vegetables (mostly head lettuce), dry bulb vegetables (onions), cucurbits (mostly melons), and cole crops (cauliflower, cabbage, broccoli, broccolini, and broccoflower). Bensulide can also be used on field-grown herbaceous plants and field-grownbulbs. Products containing bensulide are intended for outdoor homeowner use on lawns and ornamentals, and application by professional lawn care operators to lawns, ornamentals, parks, and recreation areas.

A total of 129,524 lbs active ingredient bensulide/yr were applied to 29% of the watermelon crop in the US during 1987/89.

Betamec 4 Pre-Emergence Grass Killer (PBI/Gordon Corp): Active ingredient: Bensulide 46.0%.|Pre-San 7G (PBI/Gordon Corp): Active ingredient: Bensulide 7.0%.|Betasan 3.6 (PBI/Gordon Corp): Active ingredient: Bensulide 3.6%.|Anderson's Weedgrass Preventer (The Anderson's Inc): Active ingredient: Bensulide 8.5%.|For more Formulations/Preparations (Complete) data for Bensulide (14 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies Bensulide (technical grade) as Class II: moderately hazardous; Main Use: herbicide.|Crabgrass control was decreased with ground straw and mimosa soil additions. Acid soil and increased soil cation capacity also decreased effectiveness of Bensulide.|Betasan should be used prior to germination of weed seeds... Applied to established grass lawns prior to planting, at time of planting, or on established dichondra lawns. ...Must be watered into soil after application. ...Care should be exercised if reseeding with grass is planned following treatment. Prefar should be applied by preplant incorporation 1-2 in deep, or preemergence followed by sprinkler or furrow irrigation. Rates of application are from 10-20 lb/acre for Betasan and 2-6 lb/acre for Prefar. Water at rate of 15-30 gal/3,000-3,600 sq ft is usual carrier for emulsifiable liquid formulations of Betasan. Prefar is applied in 20-50 gal/acre of water.|A preliminary test is required if mixed with wettable powder suspensions.|Compatible with other pesticides.

Continuous flow microextraction (CFME) combined with high-performance liquid chromatography-ultraviolet (HPLC-UV) detection has been applied to the analysis of five widely used pesticides, simazine, fensulfothion, etridiazole, mepronil and bensulide, present at trace levels in water samples. CFME employs a single organic solvent drop positioned at the tip of a polyether ether ketone (PEEK) tubing, which is immersed in a continuous flowing aqueous sample solution in a 0.5-mL glass chamber. The PEEK tubing acts as the organic drop holder and fluid delivery duct. Analytes are partitioned between the organic drop and the bulk sample solution. Important extraction factors including type of solvent, its volume, sample solution flow rate, extraction time, its pH and addition of salt were investigated. All pesticides exhibit good linearity in the investigated concentration range of 25-250 ng/mL with coefficients of determination (R2) ranging from 0.9879 to 0.9999 under the optimized conditions. Detection limits lower than 4 ng/mL were obtained for all analytes. The method was evaluated by analyzing natural water sample collected from a reservoir in Singapore ...|Bensulide is separated from impurities by TLC. After separation, it is eluted from the plate, oxidized to phosphate, and determined by colorimetry. It can also be analyzed quantitatively by GC.|Product analysis is by HPLC. Residues in crops and soils are determined by GLC with flame ionization detector.

Agrochemicals -> Herbicides|HERBICIDES

Computed Properties

Molecular Weight:397.5
XLogP3:4.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:10
Exact Mass:397.06050877
Monoisotopic Mass:397.06050877
Topological Polar Surface Area:130
Heavy Atom Count:23
Complexity:471
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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