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Home > Encyclopedia > S-Propyl dipropylthiocarbamate

S-Propyl dipropylthiocarbamate

S-Propyl dipropylthiocarbamate structure

S-Propyl dipropylthiocarbamate 

structure
  • CAS No:

    1929-77-7

  • Formula:

    C10H21NOS

  • Chemical Name:

    S-Propyl dipropylthiocarbamate

  • Synonyms:

    Carbamothioic acid,N,N-dipropyl-,S-propyl ester;Carbamic acid,dipropylthio-,S-propyl ester;Carbamothioic acid,dipropyl-,S-propyl ester;R-1607;Dipropylthiocarbamic acid S-propyl ester;PPTC;S-Propyl dipropylthiocarbamate;Propyl dipropylthiolcarbamate;Vernam;Vernolate;Vanalate;S-n-Propyl N,N-dipropylthiocarbamate;Perbulate

  • Categories:

    Agrochemicals  >  Herbicides

Description

S-propyl dipropylcarbamothioate is a tertiary amine.

S-Propyl dipropylthiocarbamate Basic Attributes

203.34

203.34

217-681-7

E78ZFF4KQ0

DTXSID7024376

Clear liquid

29302000

Characteristics

45.6

3.84 at 20 deg C

Amber Liquid

0.954 g/cm3 @ Temp: 20 °C

<25 °C

149-150 °C @ Press: 30 Torr

252 DEG F 0C /TECHNICAL/

1.4736 (589.3 nm 30℃)

In water, 90 mg/L at 25 deg C

0-6°C

1.04X10-2 mm Hg at 25 deg C

Oral-Rat LD50: 1200 mg/kg; Oral-Mouse LD50: 1220 mg/kg

Combustion produces toxic nitrogen oxide and sulfur oxide gas

Slight aromatic odor|Sweet and mildly garlic odor

Henry's Law constant = 3.09X10-5 atm-cu m/mol at 25 °C (est)

Clear yellow liquid /technical/|Hydroxyl radical reaction rate constant = 3.00X10-11 cu cm/molecule-sec at 25 °C (est)|Decomposed by sunlight. Stable in neutral media, and relatively stable in acidic and alkaline media. Stable up to 200 °C.

Non-corrosive

Safety Information

UN30829/PG3

2

22-51/53-36

61-36-26

FA4725000

Xn,N

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

Stable in neutral media, and relatively stable in acidic and alkaline media .

P273

H302-H411

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.|Infrared spectra indicated that vernolate disintegrated between 0 and 200 °C. Results indicate incineration is superior to chemical methods for destruction of waste pesticide chemicals. /SRP: Although burning of chemical wastes is frequently recommended, the SRP is of opinion that incineration technology has not uniformly been sufficiently perfected to assure that hazardous products are not released into the environment during the incineration process. Incineration can be an appropriate method of waste disposal if it can be demonstrated that the specific method and conditions in use result in no further release of potentially dangerous emissions./

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Facts - Vernolate. March 1999.[Available from, as of June 1, 2005: http://www.epa.gov/pesticides/reregistration/status.htm]|California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summaries. Available from: http://www.cdpr.ca.gov/docs/toxsums/toxsumlist.htm on Vernolate as of June 3, 2005.

|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 197 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P264, P270, P273, P281, P301+P312, P308+P313, P314, P330, P391, P405, and P501

Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing. /Carbamate pesticide, liquid, not otherwise specified (compounds and preparations) (agricultural insecticides, nec, liquid)/|Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Carbamate pesticide, liquid, nos (compounds and preparations) (agricultural insecticides, nec, liquid); carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/

FIRE POINT: 124 °C.

If material /is/ on fire or involved in /a/ fire do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec/|Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide. /Carbamate pesticide, liquid nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. /Carbamate pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/

A system for removing pesticides from the wash water produced by pesticide applicators as they clean their equipment has been developed. The first step is the flocculation/coagulation and sedimentation of the pesticide-contaminated wash water. The supernatant from the first step is then passed through activated carbon columns. /Pesticides/

Keep away from eyes and do not inhale; prevent drifting during use.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.

No skin irritation ... but irritating to eyes.

SOIL: At recommended rates of application, vernolate does not persist in soil and it should not leave residues that could injure subsequently planted sensitive crops(1).

Toxicity

moderately toxic

LD50 Rat oral 1780 mg/kg|LD50 Rabbit percutaneous >5000 mg/kg

Vernolate's former production may have resulted in its release to the environment through various waste streams; its former use in the US as a herbicide(1) resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 83 to 391(3-5) indicate that vernolate is expected to have high to moderate mobility in soil(SRC). Vernolate is absorbed onto dry soil(2). Volatilization of vernolate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.1X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 1.04X10-2 mm Hg(6), and water solubility, 90 mg/L(6). A considerable portion of vernolate applications to soil in the field may be lost by volatilization into the atmosphere during their incorporation into moist soils containing little clay and/or organic matter(3). Vernolate is very volatile from moist soils(3). Half-lives in soil ranging from 1.5 to 3 weeks(2,7) suggest that biodegradation may be an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), Koc values of 83-391(2-4) indicate that vernolate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(5) based upon an estimated Henry's Law constant of 3.1X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 1.04X10-2 mm Hg(6), and water solubility, 90 mg/L(6). Using this Henry's Law constant and an estimation method(5), volatilization half-lives for a model river and model lake are 45 hrs and 8 days, respectively(SRC). According to a classification scheme(7), an estimated BCF of 180(SRC), from its log Kow of 3.84(6) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Half-lives ranging from 1.5 to 3 weeks in soil environments(9,10) suggest that biodegradation may be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), vernolate, which has a vapor pressure of 1.04X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase vernolate 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 13 hours(SRC), calculated from its rate constant of 3.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vernolate was resistant to photolysis during a 30 day exposure on thin film soil(4). Vernolate is stable to photolysis in water and on soil(5).

The rate constant for the vapor-phase reaction of vernolate with photochemically-produced hydroxyl radicals has been estimated as 3.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 13 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Vernolate is stable to hydrolysis in the environment(2). Vernolate was resistant to photolysis during a 30 day exposure on thin film soil(3). Vernolate is stable to photolysis in water and on soil(2).

An estimated BCF of 180 was calculated for vernolate(SRC), using a log Kow of 3.84(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).

213.80 L/kg|Vernolate is adsorbed onto dry soil(1). An average Koc of 260 has been measured(1). The Koc values in 6 Hungarian soils (sandy loam, loam, and clay) ranged from 83 to 391(2). Measured Koc values of 259(3) and 214(4) have also been reported. According to a classification scheme(5), these Koc values suggest that vernolate is expected to have moderate to high mobility in soil. The leaching of vernolate incorporated in the upper 2 inch layer of soil was determined in 5 soils of widely different soil types having organic carbon contents ranging from 0.46 to 20.1% after two applications of 4 inches of water(6). Vernolate leached as far as the 6-9 inch layer in sandy loam (0.46% OC) and loamy sand (2.7% OC) soils, as far as the 3-6 inch layer in loam (3.2% OC) and clay (6.7% OC), and as far as the 0-3 inch layer in a peat soil (20.1% OC)(6). Leaching decreased with the clay content, as well as the organic carbon content of the soil(6).

The Henry's Law constant for vernolate is estimated as 3.1X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 1.04X10-2 mm Hg(1), and water solubility, 90 mg/L(1). This Henry's Law constant indicates that vernolate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 45 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 18 days(SRC). Vernolate's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Vernolate is very volatile from moist soils(3). A considerable portion of vernolate applications to soil in the field may be lost by volatilization into the atmosphere during their incorporation into moist soils containing little clay and/or organic matter(3). Volatility decreased as the organic and inorganic colloid content of the soils increased(3). The volatilization rate of 45.5 ppm vernolate from six Hungarian soils (sandy loam, loam, and clay) ranged from 0.17 to 1.20 ug/cm-hr(3). The volatilization rate was inversely proportional to the soil adsorption constant(3). Sixty four percent of vernolate applied to quartz sand was lost by volatilization in one day(3). Vernolate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

GROUNDWATER: Vernolate was not detected in 7 wells tested in 4 counties in California in 1994-1995(1). In the EPA's Pesticides in Ground Water Database compilation of monitoring studies, vernolate was not detected in 7 well samples collected in California from 1984-1989 and was also not detected in 76 well samples collected in California from 1984-1991(2).|DRINKING WATER: In the EPA's National Survey of Pesticides in Drinking Water Wells completed from 1985-1990, vernolate was not detected as an analyte in water samples tested from 783 rural domestic wells and 566 community water system wells, nationwide(1).

Occupational exposure and general population exposure should be low or non-existent since vernolate is no longer produced or used in the US (March, 1999). In the past, vernolate was applied directly to the soil as an herbicide and exposure to this compound was primarily by dermal contact and in the field where it was applied. (SRC)

Drug Information

/After preemergence treatment and upward translocation of (14)C throughout the entire plant/ higher concentration of (14)C vernolate was found in root and stem than in foliage.|Both peanut (Arachis hyogaea L) and soybean (Glycine may (L) merr) readily absorbed vernolate.|... /In soybean seedlings/ (14)C vernolate reached max in 48 hr. During this stage, no absorbed herbicide was degraded until seedlings were 6-7 days old.|No ... percutaneous absorption ... .|Absorbed by the roots, with translocation to the stems and leaves.

...No degradation of vernolate was observed in germinating soybean seedlings during the first 5 days.|Both peanut (Arachis hyogaea L) and soybean (Glycine max (L) merr) readily absorbed vernolate. Chemical was degraded to carbon dioxide. 2 major and 2 minor metabolites were indicated... .|Vernolate gives sulfoxide degradation product in living mice. /from table/|Thiocarbamates are detected in the liver of mice 20 min after ip treatment with EPTC, molinate, pebulate, and vernolate at 1 m mole/kg but not after administration of benthiocarb, butylate, or cycloate.|One of the two major metabolic pathways for thiocarbamates in mammals is sulfoxidation, followed by conjugation with glutathione (GSH) by GSH S -transferase. The GSH conjugate is then cleaved to the cysteine derivative, which is subsequently acetylated and excreted as S -carbamoyl-mercapturic acid. ...Sulfoxidation of thiocarbamates such as EPTC, molinate, pebulate, and vernolate undoubtedly represents a detoxification mechanism in mammals, the sulfoxides generally being less toxic than the parent compounds. The lower toxicity of the sulfoxides is probably attributable to the high rate of cleavage and elimination as glutathione conjugates

/It was/... reported that five thiocarbamate herbicides (EPTC, molinate, butylate, vernolate and ethiolate) inhibited rat liver low Km aldehyde dehydrogenase (ALDH2), probably via their sulfoxides. The authors speculated on the basis of the ALDH2 inhibition, that workers exposed to ethanol after the use of the above pesticides may exhibit a reaction like that experienced by individuals treated with disulfiram, which is used in alcohol aversion therapy.|...The formation of S-methyl esters of thiocarbamates /was studied/ as a bioactivation mechanism in mice for thiocarbamates. After ip injection of EPTC, molinate, butylate, vernolate, pebulate, diallate, triallate, liver extracts contained the S-methyl derivatives of the respective parents. Additionally, when the dosing was conducted with the glutathione (GSH) conjugate of molinate, the liver extract contained methyl molinate ester. Thus, methylation appears to be a way to reactivate molecules such as the GSH-conjugates of thiocarbamates. The methylated thiocarbamate can be released again into circulation as a molecule that can undergo additional reactions such as sulfoxidation.|Preexposure to vernolate resulted in reduced (14)CO2 production /in germinating seeds/. ...Suggests that inhibition of enzyme synthesis may be primary site of action of thiocarbamate... in germinating seeds.

Skin contamination should be removed promptly by washing with soap and water. Contamination of the eyes should be treated immediately by prolonged flushing of the eyes with copious amounts of clean water. If dermal or ocular irritation persists, medical attention should be obtained without delay. /Other herbicides/|Ingestions of these herbicides are likely to be followed by vomiting and diarrhea due to the irritant properties of most of the toxicants. ... Activated charcoal is probably effective in limiting irritant effects and reducing absorption of most or all of these herbicides. Aluminium hydroxide antacids may be useful in neutralizing the irritant actions of more acidic agents. Sorbitol should be given to induce catharsis if bowel sounds are present and if spontaneous diarrhea has not already commenced. Dehydration and electrolyte disturbances may be severe enough to require oral or intravenous fluids. There are no specific antidotes for poisoning by these herbicides. In the case of suicidal ingestions, particularly, the possibility must always be kept in mind that multiple toxic substances may have been swallowed. /Other herbicides/|If serious dehydration and electrolyte depletion have occurred as a result of vomiting and diarrhea, monitor blood electrolytes and fluid balance and administer intravenous infusions of glucose, normal saline Ringer's solution, or Ringer's lactate to restore extracellular fluid volume and electrolytes. Follow this with oral nutrients as soon as fluids can be retained. Fluids serve to support excretion of the toxicants. Supportive measures are ordinarily sufficient for successful management of excessive exposures to these herbicides. /Other herbicides/

S,N,N'-tripropylthiocarbamate

S-Propyl dipropylthiocarbamate Use and Manufacturing

Methods of Manufacturing

The preparation method 1 is prepared by reacting N, N-dipropylcarbamoyl chloride with sodium propyl mercaptan. The preparation method 2 is prepared by the action of dipropylamine and COS to prepare N, N-dipropylaminothiocarbamic acid, and then reacts with dipropyl sulfate to synthesize dimethoate.

Uses

Herbicide.

Emulsifiable liquid; 10% granules|Granules: 5-10% active. Emulsifiable concentrate: 6 lb/gal active.|'Vernam E', emulsifiable concentrate (720 or 840 ai/l); 'Vernam G', granules (50 or 100 g/kg); Mixtures include: 'Surpass E'...emulsifiable concentrate (800 g vernolate/l + dichlormid); 'Vernam' atrazine 10-5G, granules (100 g vernolate + 50 g atrazine/kg)|Mixed formulations: (vernolate +) EPTC|Technical material is 95% pure.

Control of germinating broad-leaved and grass weeds in peanuts, soya beans, maize, tobacco and sweet potatoes, at 1.5-3.0 kg/ha. Soil incorporation is necessary, either pre-planting or pre-emergence.|Most thiocarbamate herbicides are available ... as emulsifiable concentrates... . Diluted in water and applied in vol of 20-100 gal/acre, or as 10-20% granules. For optimum weed control ... vernolate must be mechanically incorporated into soil ... 2-3 inches immediately after application.|Carbamates ... are used as preplanting sprays for weed control in canning peas and sugar beets. /Carbamates/|If vernolate is applied to extremely dry soils during very dry climatic conditions, incorporation may be accomplished by overhead irrigation following application. Rates: 2-4 lb/acre. The emulsifiable liquid concentrate is diluted with water prior to application.|Incompatibilities: A preliminary test is necessary for mixing with wettable powders.

Product analysis is by GLC ... . Residues in crops and soils are determined by GLC or by colorimetry after conversion to a derivative.|GC with ECD for determination of carbamate residues in soil.|GC determination of carbamate herbicides on food and crops with the thermionic, ECD and FPD.|Study of micro quantities of vernolate in soil by extraction and GLC.|For more Analytic Laboratory Methods (Complete) data for VERNOLATE (10 total), please visit the HSDB record page.

Agrochemicals -> Herbicides|HERBICIDES

Computed Properties

Molecular Weight:203.35
XLogP3:3.8
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:7
Exact Mass:203.13438547
Monoisotopic Mass:203.13438547
Topological Polar Surface Area:45.6
Heavy Atom Count:13
Complexity:133
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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