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Home > Encyclopedia > Thiobencarb

Thiobencarb

Thiobencarb structure

Thiobencarb 

structure
  • CAS No:

    28249-77-6

  • Formula:

    C12H16ClNOS

  • Chemical Name:

    Thiobencarb

  • Synonyms:

    Carbamothioic acid,N,N-diethyl-,S-[(4-chlorophenyl)methyl] ester;Carbamic acid,diethylthio-,S-(p-chlorobenzyl) ester;Carbamothioic acid,diethyl-,S-[(4-chlorophenyl)methyl] ester;α-Toluenethiol,p-chloro-,diethylcarbamate;Saturn (pesticide);IMC 3950;S-(p-Chlorobenzyl) N,N-diethylthiocarbamate;S-(4-Chlorobenzyl) N,N-diethylthiocarbamate;Saturn;Benthiocarb;S-p-Chlorobenzyl diethylthiocarbamate;S-(p-Chlorobenzyl) N,N-diethylthiolocarbamate;p-Chlorobenzyl N,N-diethylthiolcarbamate;p-Chlorobenzyl diethylthiolcarbamate;B 3015;S-(4-Chlorobenzyl) diethylthiolcarbamate;Thiobencarb;S-4-Chlorobenzyl N,N-diethylthiolcarbamate;S-(4-Chlorobenzyl) diethylthiocarbamate;Bolero;Bolero 8EC;Sadan;B 3015 (pesticide);Bencarb;11099-66-4

  • Categories:

    Agrochemicals  >  Herbicides

Description

Amber-colored, slightly water-soluble, liquid.


Thiobencarb is a pale yellow to brownish yellow liquid. Non corrosive. Used as an herbicide.


Thiobencarb is a pale yellow to brownish yellow liquid. Non corrosive. Used as an herbicide.|Thiobencarb is a member of monochlorobenzenes and a monothiocarbamic ester.

Thiobencarb Basic Attributes

257.78

257.78

248-924-5

90LN6Y7I7H

3082|2757

DTXSID6024337

Clear, colorless liquid|Pale yellow liquid

2930200011

Characteristics

45.6

3.40

Pale yellow Liquid

1.145-1.180 g/cm3 @ Temp: 20 °C

3.3 °C

126-129 °C @ Press: 8 x 10-3 Torr

165.8±28.4 °C

1.563

In acetone, methanol, n-hexane, toluene, dichloromethane and ethyl acetate >500 g/L

APPROX 4°C

1.8X10-5 mm Hg at 23 deg C

Oral-Rat  LD50: 920 mg/kg; Oral-Mouse LD50: 560 mg/kg

Combustion produces toxic nitrogen oxides, chlorides and sulfur oxides

Slight aromatic odor

Henry's Law constant = 2.7X10-7 atm-cu m/mol at 25 °C (est)

155.71 Ų [M+H]+

Stable in water, hydrolysis half-life >1 yr (25 °C, pH 4,7 and 9). Aqueous photolysis half-life - 3.6 days in natural water, 3.7 days in distilled water (both at 25 °C)|Hydroxyl radical reaction rate constant = 2.5X10-11 cu cm/molecule-sec at 25 °C (est)

Thio and dithiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids.

Thiocarbamate Esters and Salts/Dithiocarbamate Esters and Salts

THIOBENCARB is a thiocarbamate. Flammable gases are generated by the combination of thiocarbamates and dithiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates and dithiocarbamates are incompatible with acids, peroxides, and acid halides.

Relatively noncorrosive

Safety Information

UN 3082

3

22-50/53

60-61

EZ7260000

Xi,N,Xn

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

Stable under acid and moderately alkaline conditions.

P273-P501

H302-H410

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|Nonrefillable container. Do not reuse or refill this container. Offer for recycling if available. Clean container promptly after emptying. Triple rinse as follows: Empty the remaining contents into application equipment or a mix tank. Fill the container 1/4 full with water. Replace and tighten closures. Tip container on its side and roll it back and forth, ensuring at least one complete revolution, for 30 seconds. Stand the container on its end and tip it back and forth several times. Empty the rinsate into application equipment or a mix tank or store rinsate for later use or disposal. Repeat this procedure two more times. /Bolero 8 EC Herbicide/|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

USEPA/Office of Prevention, Pesticides and Toxic Substances, Reregistration Eligibility Decision Document - Thiobencarb EPA 738-R-97-013 (December 1997). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of October 11, 2012: http://iaspub.epa.gov/apex/pesticides/f?p=CHEMICALSEARCH:1]

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|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]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 257 companies from 3 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, P309+P311, P314, P330, P391, P405, and P501|P201, P202, P260, P264, P270, P281, P301+P312, P308+P313, P309+P311, P330, P405, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: SMALL FIRE: Dry chemical, CO2, water spray or regular foam. LARGE FIRE: Water spray, fog or regular foam. Do not scatter spilled material with high-pressure water streams. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal. FIRE INVOLVING TANKS: Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

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)|Applicators and flaggers must wear: long sleeved shirt and long pants, shoes plus socks. /Bolero 8 EC Herbicide/|Mixers and Loaders must wear: long sleeved shirt and long pants, chemical-resistant gloves, such as barrier laminate, butyl rubber greater than or equal to 14 mils, nitrile rubber greater than or equal to 14 mils or Viton greater than or equal to 14 mils, chemical-resistant apron and shoes plus socks. /Bolero 8 EC Herbicide/|For other handling activities and in case of a spill or other emergency exposure, handlers must wear: coveralls over long sleeved shirt and long pants, chemical-resistant gloves such as barrier laminate, butyl rubber greater than or equal to 14 mils, nitrile rubber greater than or equal to 14 mils or Viton greater than or equal to 14 mils, chemical-resistant footwear and chemical-resistant apron when cleaning equipment. /Bolero 8 EC Herbicide/|All workers must wear: waterproof boots plus socks when entering flooded fields following treatment. /Bolero 8 EC Herbicide/|For more Personal Protective Equipment (PPE) (Complete) data for THIOBENCARB (6 total), please visit the HSDB record page.

Do not contaminate /downstream/ water when disposing of equipment washwaters. /Bolero 8 EC Herbicide/

Keep out of reach of children and animals. Do not get in eyes, on skin, or on clothing. Avoid contact of spray to eyes and skin.|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.|Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR part 170. /Bolero 8 EC Herbicide/|For terrestrial uses, do not apply directly to water, to areas where surface water is present or to intertidal areas below the mean high water mark. /Bolero 8 EC Herbicide/|For more Preventive Measures (Complete) data for THIOBENCARB (9 total), please visit the HSDB record page.

Causes eye and skin irritation

Thiobencarb has been observed to undergo surface runoff, with subsequent transport to rivers and lakes, after being applied as a herbicide(1,2); in one study, about 2% of the total thiobencarb application was removed from a field through surface runoff(2).

SEDIMENT: Thiobencarb concentrations of 2-13 ug/kg were detected sediments collected from the Shin River in Japan in 1999(1). Thiobencarb concentrations of <1 to 10 ug/kg dry wt were detected in sediments collected from Lake Biwa Japan in 2007(2).

SOURCE DOMINATED: Ambient air monitoring (conducted in May and June 1986) of thiobencarb at four sites in CA in the vicinity of current agricultural usage detected overall ave concns of 12.9-39 ng/cu m(1); the highest daily ave was 67.8 ng/cu m(1); levels of <2.0 ng/cu m (detection limit) were monitored at a background site (not near the usage areas)(1); several days after thiobencarb usage had ceased, air concns were below the detection limit at the use areas(1).|RURAL/REMOTE: The maximum concentration and percent detections of thiobencarb in air over the Mississippi River from New Orleans, LA to St. Paul, MN during June 1994 was 7.1 ng/cu m and 40%, respectively(1). Thiobencarb concentrations of approximately 1 to 25 ng/cu m were monitored in the air over Rolling Fork, MS during late April and may 1995(2).

Toxicity

moderately toxic

LD50 Rat oral 1300 mg/kg|LD50 Rat percutaneous 2900 mg/kg|LD50 Rat oral 1903 mg/kg|LC50 Rat inhalation > 42.8 mg/L (1 hour)|For more Non-Human Toxicity Values (Complete) data for THIOBENCARB (6 total), please visit the HSDB record page.

/AQUATIC SPECIES/ Thiobencarb (S-(4-chlorobenzyl)-N,N-diethyl thiol carbamate) has been one of the herbicides previously associated with fish kills in agricultural drains near the Sacramento/San Joaquin rivers and their Delta. To define targets of thiobencarb embryotoxicity and to determine the degree of protection afforded by the chorion, medaka (Oryzias latipes) embryos were exposed under static nonrenewal conditions. Responses to exposures initiated at blastula or at initiation of heart beat (stages 10 and 23, respectively) were assessed. In addition, enzymatically dechorionated embryos (stage 13, gastrula) were exposed and compared to responses in embryos with intact chorions. Embryos were observed daily for development and for gross abnormalities including: bradycardia, pericardial edema, hemostasis, poor yolk resorption, cephalic and spinal deformities, and abnormal hatching. A subset was also evaluated for histologic alterations. Based on gross abnormalities, the concentration of thiobencarb affecting 50% (EC50) of embryos exposed at blastula was 3.6 mg/L, while the putative no observable effect concentration (NOEC) was 1.0 mg/L. For embryos exposed at onset of heart beat (stage 23), these values were 4.1 and 2.5 mg/L, respectively. Dechorionated embryos tended to be more sensitive than their chorionated cohorts (LC50=2.5 vs. 1.0 mg/L). Liver histologic alterations were seen in chorionated embryos at EC50 levels and higher. Stage-specific toxicity was evident; nevertheless, the EC50 and NOEC values for embryos treated at stage 10 and stage 23 were similar.|/AQUATIC SPECIES/ Chronic toxicity studies were conducted with an algae (Nannochloris oculata) and the cladoceran (Daphnia magna) to determine their relative sensitivities to the thiocarbamate herbicide thiobencarb (S-4-chlorobenzyl diethylthiocarbamate). Most of the algal populations were initially affected by exposure to the herbicide. Thiobencarb concentrations higher than 0.5 mg/L significantly reduced algal densities after 24-hr exposure. The 24-hr static EC50 in D. magna was 3.01 mg/L. The sublethal effects of 0.3, 0.37, 0.5, 0.75, and 1.5 mg/L of thiobencarb concentrations on the survival, reproduction, and growth of D. magna were monitored for 21 days. The parameters used to determined the effect of the herbicide on D. magna were mean total young per female; mean brood size; days to first brood; intrinsic rate of natural increase (r); growth; and survival. Reproduction was significantly reduced at thiobencarb concentrations of 0.30 mg/L and higher while survival was affected after exposure to 0.75 and 1.5 mg/L of the pesticide. The r value decreased with increasing concentrations of thiobencarb. Growth, as measured by body length, was depressed significantly after exposure to all herbicide concentrations tested.|/AQUATIC SPECIES/ The midge Chironomus tepperi was used in laboratory experiments to assess the relative toxicity of formulated molinate, clomazone, and thiobencarb, three herbicides used in Australian rice crops. Static bioassays were initiated with first-instar larvae at herbicide concentrations between 0.0625 and 2 times the anticipated field concentrations (AFCs) expected from the registered application rates. Adult emergence success, development time, and wing length were used as indices of the effect of each herbicide. ... Thiobencarb reduced emergence success of adult C. tepperi at 0.0625 times the AFC (0.1875 mg/L) as well as decreasing male adult size and increasing development time for males and females at 0.125 times the AFC (p<0.05). Nontarget effects of the herbicides on aquatic invertebrate communities were assessed in shallow experimental ponds using commercial application rates. One week after treatment, only thiobencarb had a significant effect, suppressing populations of chironomids, calanoids, and cyclopoids (p<0.05). Four weeks later, all populations had recovered, equaling or exceeding control densities.

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

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 309-5000(2-4), indicate that thiobencarb is expected to have low to slight mobility in soil(SRC). Soils studies have demonstrated that volatilization from soil surfaces is not an important fate process(5). Minor loss of thiobencarb occurs from photodegradation on soil surfaces(6) with one reported photolysis half-life of 168 days(5). Biodegradation is the major environmental fate process in soil(3,5,6). Biodegradation has also been shown to occur more rapidly in soils that have been acclimated to thiobencarb(7). The half-life of thiobencarb in soil has been reported to be 2 to 3 weeks in aerobic conditions and 6 to 8 months in anaerobic conditions(6). Soil half-lives of 21-58 days are also reported based on field studies(3,5) and a half-life of 3.5 days in an acclimated rice field(8).|AQUATIC FATE: Based on a classification scheme(1), a measured Koc values ranging from 309-5000(2-4), indicates that thiobencarb is expected to adsorb to suspended solids and sediment(SRC). One study in a flooded soil showed that more thiobencarb partitioned to the soil than remained in the water(5). Volatilization from water surfaces is not expected(6) based upon an estimated Henry's Law constant of 2.7X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 2.2X10-5 mm Hg(7), and water solubility, 28 mg/L(7). According to a classification scheme(8), measured BCFs ranging from 66 to 523(9-11), suggests the potential for bioconcentration in aquatic organisms is moderate-to-high(SRC). Biodegradation is a major environmental fate process for thiobencarb in aquatic ecosystems(12). Degradation studies have shown that thiobencarb can degrade much more rapidly in non-sterile water/sediment systems than in sterile systems(12,13). Biodegradation has been shown to occur more rapidly in systems that have been acclimated to thiobencarb(14). Degradation in natural water may occur abiotically through photooxidation(14). Photochemically generated hydroxyl radicals can react readily with thiobencarb in natural waters, although the presence of a photo-sensitizing agent (e.g., humic acids) is required(15). Laboratory persistence studies have measured half-lives ranging from 6 to 42 days in water or water-sediment systems(12,13). Thiobencarb is stable to aqueous hydrolysis in the environment(16).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thiobencarb, which has a vapor pressure of 2.2X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase thiobencarb 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 15 hrs(SRC), calculated from its rate constant of 2.5X10-11 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(3). Particulate-phase thiobencarb may be removed from the air by wet and dry deposition(SRC). Thiobencarb is susceptible to direct photolysis(4).

When an aqueous solution of 14(C)-benthiocarb was exposed to sunlight, volatization of benthiocarb occurred. The presence of soil in the solution retarded the volatilization. About 60% of the volatilized radioactivity was composed of benthiocarb. Some s4-chlorobenzaldehyde was also observed. Irradiation by sunlight and ultraviolet light produced benthiocarb sulfoxide ..., desethyl benthiocarb ..., 4-chlorobenzyl alcohol ..., 4-chlorobenzaldehyde, 4-chlorobenzoic acid ..., 4-hydroxybenzyl alcohol, 4-hydroxybenzaldehyde ..., 4-hydroxybenzoic acid ..., 2-hydroxy benthiocarb ..., 4-chlorobenzyl N-ethylamine ..., 4-chlorobenzyl diethylamine ..., bis(4-chlorobenzyl)sulfide ..., 4-hydroxybenzyl ester of N-ethyl thiolcarbamic acid, 4-hydroxybenzyl ester of N,N-diethyl thiolcarbamic acid ..., 4-chlorobenzyl N,N-diethylcarbamate ..., and methyl N,N-diethylcarbamate ... . About 20 other compounds were also detected by TLC but not identified.|The rate constant for the vapor-phase reaction of thiobencarb with photochemically-produced hydroxyl radicals has been estimated as 2.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 15 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Thiobencarb photodegraded with a calculated half-life of 190 days in a sterile pH 7 aqueous buffer solution at 25 °C(2). The photoproducts identified in the nonsensitized irradiated solutions were 4-chlorobenzoic acid, 4-chlorobenzaldehyde, 4-chlorobenzyl alcohol, and N,N-diethyl-4-(chlorobenzylthio)carbamate S-oxide (thiobencarb sulfoxide)(2). Based on 30-day studies, thiobencarb slowly photodegraded on sandy loam soil irradiated under natural sunlight at Richmond, CA with an extrapolated half-life of 168 days, and degraded in the dark controls with a calculated half-life of 280 days(2). In the study, no volatile or non-volatile degradates exceeded 1.3% of applied(2). Non-extractable residues did not exceed 8.7% in the irradiated samples and 5.7% in the dark control samples by 26 days(2). Thiobencarb is stable to degradation by hydrolysis(2). Thiobencarb did not degrade in sterile aqueous buffer solutions (pH 5, 7, and 9) that were incubated in darkness at 25 °C for 30 days(2).|Thiobencarb was shown to photolyze directly in sunlight or UV light exposure (365 nm) yielding 4-chlorobenzyl alcohol and 4-chlorobenzaldehyde as products(1). In aqueous photolysis studies, thiobencarb photolyzed slowly when exposed to sunlight (<10% during 10 hr of exposure) yielding thiobencarb S-oxide as an intermediate product(2); addition of small amounts of hydrogen peroxide or other photo-sensitizers (such as tryptophan and methylene blue) greatly increased the photodecomposition rate(2); in the presence of hydrogen peroxide, the photodecomposition half-life increased to 41 hr(2); the photo-oxidant responsible for the degradation was probably hydroxyl radicals(2); thiobencarb was not oxidized by molecular singlet oxygen(2). In aqueous solutions exposed to Oct sunlight (at Davis, CA) for 245 hr, only 3% of initial thiobencarb photodecomposed while 85% decomposed in 100 uM solutions of hydrogen peroxide(3); photodecomposition in sterilized settling pond water was about 30% in 200 hr which demonstrated that substances occurring in natural waters accelerated the photodegradation of thiobencarb(3); indirect photolysis via hydroxyl radicals was considered the most likely route of the photodegradations(3).

169.82|Using a continuous-flow water system and a 14-day exposure period, a thiobencarb BCF of 170 was measured in a freshwater fish (topmouth gudgeon, Pseudorasbora parva)(1). Using a continuous-flow water system and a 14 day exposure period, a thiobencarb BCF of 66 was measured in a freshwater fish (willow shiner, Gnathopogon caerulescens)(2). Average BCFs of 209 and 523 were calculated for pale chub (Zacco platypus) and ayu sweetfish (Plecoglossus altivelis), respectively, collected from Japanese rivers by measuring the water concentration and the concentration in fish(3). Thiobencarb residues accumulated in juvenile bluegill sunfish (Lepomis macrochirus) exposed to 14C-thiobencarb at 0.05 mg/L, with maximum bioconcentration factors of 128, 639, and 411 for edible (muscle) tissue, nonedible tissue, and whole fish, respectively(4); by day 3 of the depuration period, 93-95% of the accumulated 14C residues were eliminated from the tissues(4). Pale chub, ayu sweetfish, and dark chub (Zacco temminckii) collected in rivers flowing into Lake Biwa, Japan between 1992-1994 had field BCFs of 68, 56, and 248, respectively(5). Willow shiner, topmouth guddeon, and killifish (Pryzias latipes) had laboratory BCFs of 65, 170 and 382, respectively(5). In a laboratory experiment, /bighead carp/ Aristichthys nobilis had BCFs of 714 and 1772 (calculated using homogenized tissue) for initial thiobencarb concentration of 88 and 9 umol/L, respectively(6). According to a classification scheme(7), these BCFs suggest the potential for bioconcentration in aquatic organisms is moderate to high(SRC).

1.86e+03 L/kg|Koc values of 309 and 1043 were measured for thiobencarb in two Japanese soils (respective organic carbon contents of 1.35 and 4.24%)(1). The US Dept of Agric's Pesticide Properties Database has selected a recommended thiobencarb Koc value of 900 based on multiple reported Koc values(2). An average Koc of 5000 was measured in four different soil types (organic carbon content of 0.2-6.8%)(3). Using three Florida soils, Koc values of 765, 539 and 1195 were measured in Pahokee muck (48.6% organic carbon), Everglades muck (34.1% organic carbon) and Immokalee sand (1.1% organic carbon) respectively(4). According to a suggested classification scheme(5), Koc values ranging from 309-5000 suggest that thiobencarb is expected to have moderate to slight mobility in soil. In laboratory and greenhouse mobility studies using these soils, more than 93% of all applied thiobencarb remained in the upper 1 cm after leaching during unsaturated flow(6). In lysimeter leaching studies using a mineral alluvial soil and a humic volcanic ash soil, thiobencarb did not leach below the 15 cm level(7); greater than 60% of applied thiobencarb remained in the upper 5 cm level(7). In greenhouse studies using flooded Australian rice growing soils, 65-70% of applied thiobencarb was recovered from the 0-1 cm layer of soil while less than 2% was recovered from each layer down to 10 cm(8). A field study in a paddy in India found that no leaching or percolation of thiobencarb occurred from the 6-12 inch soil layer(9).

The Henry's Law constant for thiobencarb is estimated as 2.7X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 2.2X10-5 mm Hg(1), and water solubility, 28 mg/L(1). This Henry's Law constant indicates that thiobencarb is expected to be essentially nonvolatile from water surfaces(2). Thiobencarb's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Thiobencarb is not expected to volatilize from dry soil surfaces based upon its vapor pressure(SRC). During a 14 day water-based degradation study, <0.1% of added thiobencarb volatilized(3). In laboratory studies simulating flooded rice paddy conditions during summer months (eg 27.5 °C), only minor amounts of thiobencarb volatilized(4). The results of these volatilization tests indicate that thiobencarb is expected to remain in the aqueous compartment(4). Soils studies have demonstrated that volatilization from soil surfaces is not an important fate process(5).

GROUNDWATER: The occurrence and maximum concentration of thiobencarb in shallow groundwater in the United States collected as part of the National Water-Quality Assessment (NAWQA) completed during 1993-95, was 0.1% of all 1034 sites and 0.002 ug/L, respectively(1).|DRINKING WATER: Thiobencarb was detected at the parts per trillion level in raw and finished drinking waters collected from a Japanese source which received influent waters from a rice paddy region(1). Thiobencarb was associated with a taste problem in the drinking water in the City of Sacramento where the bitter taste was believed to be caused by thiobencarb sulfoxide, which is a major oxidized product of thiobencarb generated during chlorination(2); the increase in consumer complaints always occurred when thiobencarb was detected at or above 1 ppb in the Sacramento River in May and June as a result of its discharges from thiobencarb-treated rice fields(2).|SURFACE WATER: Monitoring of seven Japanese rivers flowing into Lake Biwa in 1988 and 1989 detected thiobencarb levels as high as 2.4 ng/mL, although levels were generally below 0.2 ng/mL(1). Water samples collected from the middle of Lake Albufera in Valencia, Spain during May 29 and 30, 1985 contained thiobencarb levels of 0.5 and 2.6 ppb; maximum levels of 15 ppb were detected in water samples from the lake channel; monitoring was conducted during the agricultural use season(2). In the Sacramento River and Delta (California), which are areas heavily impacted by rice crops, the concentration of thiobencarb in drain and river water ranged from <1-170 and <0.1- 6 ppb, respectively, between 1981 and 1997(3).|SURFACE WATERS: Thiobencarb detections in surface waters were reported for filtered water samples only (detection limits varied from 0.002-0.008 mg/L)(1). Detection of thiobencarb were listed for 8 states: California, Georgia, Maryland, North Carolina, Oregon, Oklahoma, Texas, and Washington(1). Thirty-nine positive detections were reported for 3,130 samples (approximately 1%) with a maximum concentration of 0.24 mg/L (July 22, 1992 and Aug 26, 1992; Klamath Falls, OR) and a mean concn of 0.10 mg/L(1). Whole (i.e., unfiltered) water samples did not find detectable levels of thiobencarb(1). In Spain for the year 1995, the estimated concn of thiobencarb in 1.2% of surface waters (with detections) was 0.1 ug/L(2). The highest concentration of thiobencarb in Sacramento-San Joaquin Delta water was 1.7 ug/L between the years 1983 and 1987(3). Thiobencarb has been detected in 76% of 164 US stream water samples collected at a concentration range of 0.001 to 0.011 ug/L(4). Thiobencarb concentrations of <0.01 to 0.06 ug/L were detected water samples collected from Lake Biwa Japan in 2007(5).|RAIN: Thiobencarb was detected in rain water samples collected in both urban and agricultural areas of Mississippi in 1995 (concentrations not reported)(1). Thiobencarb was detected in rain water samples collected in eastern Japan between July 1999 and July 2000 at an average concentration 0.163 ug/L(2).

Occupational exposure to thiobencarb occur through inhalation and dermal contact at areas where thiobencarb is used as a herbicide(1). The general population may be exposed to thiobencarb through ingestion of foods containing thiobencarb residues(1). Monitoring data indicate that the general population may also be exposed to thiobencarb via inhalation of ambient air, ingestion of drinking water and dermal contact with this compound(SRC).

Drug Information

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.)

In a general metabolism study, the disposition and metabolism of (Phenyl-U-(14)C)-thiobencarb was investigated in male and female Sprague-Dawley rats at a single low oral dose (30 mg/kg), repeated low oral doses (30 mg/kg x 14 days), and a single high dose (300 mg/kg). Thiobencarb was rapidly absorbed after oral administration as judged by the rate of excretion. No significant sex-related or dose group differences in absorption were noted. Excretion was relatively rapid at all doses tested, with a majority of radioactivity eliminated in the urine and feces by 48 hours. The extent of excretion was completed by 72 hours at the 300 mg/kg dose, but the mechanism responsible for this delay was not identified. No significant sex- or dose-related differences in urinary or fecal excretion of thiobencarb derived radioactivity were noted. Repeated low oral dosing did not affect elimination of thiobencarb in either male or female rats. Fecal elimination of (Phenyl-U-(14)C)-thiobencarb derived radioactivity was a minor route of excretion, and for urine, no significant sex- or dose-related differences in amount of radioactivity excreted by this route were observed. Residual levels of thiobencarb derived radioactivity were also minor (less than 0.5% of an administered dose).|(14)C Benzyl methylene labeled benthiocarb was taken up through the roots and translocated into whole plants by rice, barnyard grass, wild amaranth, smartweed, and lambsquarters plants. It was translocated from a leaf into other leaves also. When applied to seeds, it was rapidly absorbed and accumulated mostly in the embryo.

In a general metabolism study, the disposition and metabolism of (Phenyl-U-(14)C)-thiobencarb was investigated in male and female Sprague-Dawley rats at a single low oral dose (30 mg/kg), repeated low oral doses (30 mg/kg x 14 days), and a single high dose (300 mg/kg). ... Urinary and fecal metabolites of (Phenyl-U-(14)C)-Thiobencarb were isolated and identified by HPLC, TLC, and mass spectral analysis. The major metabolite detected was the glycine conjugate 4-chlorohippuric acid, comprising between 74-81% of an administered dose in urine. Other metabolites detected included 4-chlorobenzyl methyl sulfoxide and -sulfone, des-ethyl thiobencarb, and 4-chlorobenzoic acid, each representing less than 10% of an administered dose of thiobencarb. A single high or repeated low oral dose did not significantly affect the urinary or fecal metabolite profile for thiobencarb in male or female rats.|Roots of rice and barnyard millet were soaked in (14)C benthiocarb solution for 48 hr. Degradation was rapid and most of the radioactivity in the plants was extractable with aqueous acetone. The same metabolites were observed in root and foliage of both plants and little difference in the metabolic pattern of both plants was observed. The metabolites were identified as desethyl benthiocarb ... , S-4-chlorobenzyl thio- ... carbamate ... , 4-chlorobenzoic acid ... , 2-hydroxybenthiocarb ... , desethyl-2-hydroxybenthiocarb ... , 4-chloro-2- hydroxybenzyl alcohol ... , and 4-chlorosalicylic acid ... . Hydrolysis of unextractable radioactivity with b-glucosidase and hydrogen chloride yielded the aglycons.|(14)CO Thiocarbamates were administered to rats. Relatively large amounts (14)CO2, as compared to (14)C in the urine, were expired. Analyses of urine, feces and liver indicated that these compounds were metabolized via two pathways. One pathway produced larger amounts of (14)CO2 from thiocarbamates than from the sulfoxide derivatives and their GSH and cysteine conjugates. In the other pathway, metabolism of a thiolcarbamate proceeded via the sulfoxide and S-(N,N-dialkylcarbamoyl)glutathione. Degradation of the glutathione conjugate produced the corresponding cysteine conjugate, mercapturic acid and mercaptoacetic acid. The appropriate mercapturic acids were seen in urine when benthiocarb, cycloate, molinate and pebulate were administered to rats.|The fate of (14)C-labeled benthiocarb was studied with white mice in vivo and in vitro. After oral administration, benthiocarb was rapidly translocated into organs. There was rapid urinary excretion of labeled material; slight excretion in feces; and only a little expired. The major metabolites identified were: 4-chlorohippuric acid, 4-chlorobenzoic acid, glucuronide of 4-chlorobenzoic acid, and 4-chlorobenzyl alcohol. In liver homogenates, the microsomal fraction exhibited highest activity and NADP accelerated the degradation. In vitro metabolites were identified as: N-desethylbenthiocarb, bis(4-chlorobenzyl)mono- and di-sulfides, and 4-chlorobenzoic acid.|For more Metabolism/Metabolites (Complete) data for THIOBENCARB (6 total), please visit the HSDB record page.

4.57 Days

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)

Skin decontamination: Skin contamination should he treated promptly by washing with soap and water. Contamination of the eyes should be treated immediately by prolonged flushing of the eyes with large amounts of clean water. If dermal or ocular irritation persists, medical attention should be, obtained without delay.|Gastrointestinal decontamination: Ingestion of these herbicides are likely to be followed by vomiting and diarrhea due to their irritant properties. Management depends on: (1) the best estimate of the quantity ingested, (2) time elapsed since ingestion, and (3) the clinical status of the subject. Activated charcoal is probably effective in limiting irritant effects and reducing absorption of most or all of these herbicides. Aluminum 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 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. If large amounts of herbicide have been ingested and the patient is seen an hour of the ingestion, gastrointestinal decontamination should be considered. If the amount of ingested herbicides was small, if effective emesis has already occurred, or if treatment is delayed, administer activated charcoal and sorbitol by mouth.|Intravenous fluids: 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.|/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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Carbamates and related compounds/|For more Antidote and Emergency Treatment (Complete) data for THIOBENCARB (6 total), please visit the HSDB record page.

/GENOTOXICITY/ In a clastogenicity test using human lymphocytes, thiobencarb (96.0% a.i.) was tested at dose levels of 0, 5, 10, and 20 ug/mL without S9 activation and at dose levels of 0, 10, 20, and 40 ug/mL with S9 activation. No mutagenic activity was noted.

benthiocarb

Thiobencarb Use and Manufacturing

Methods of Manufacturing

Preparation of carbon oxysulfide by synthetic route from Anbara Chemical's Jinggang Factory, Japan. Put the coke into a carbon monoxide generator, oxidize it with oxygen to generate carbon monoxide, and send it to the gas collecting tank through water sealing and washing pressure, and then put it into the gas tank for standby after alkaline washing. Molten sulfur vapor is stored in heat preservation and is pumped to the carbon oxysulfide reactor by submerged pump. The carbon monoxide is preheated into the carbon oxysulfide reactor, and under the action of a catalyst, the reaction temperature is maintained by electric heating to prepare carbon oxysulfide. Preparation of Amine Salt Diethylamine is mixed with the solvent, and the reaction liquid is sent to the top jet absorber by the reaction tank circulation pump under stirring, and reacts with the gaseous carbon oxysulfide until the end, the gas is discharged through 4 sets in series The activated carbon adsorber is emptied after adsorption. Synthetic grass dan The amine salt reaction solution is reacted with p-chlorobenzyl chloride to produce grass dan. After washing and stratifying, most of the solvent is removed from the organic phase, and the He Cao Dan crude oil is obtained by the Qiao plate membrane type.

Uses

It is a broad-spectrum, systemic conductivity type, selective herbicide for paddy field. It can be absorbed by the roots and shoots of weeds, and has a strong inhibitory effect on the growth points of the weeds and the mitosis of the cells, causing the death of the weeds. It has special effects on annual grass weeds and sedge weeds, and can also control some broad-leaved weeds. Seedling field and direct seeding field can be treated before sowing or seedling stage. Before sowing, spray water with 50% emulsifiable concentrate 30~37.5mL/100m2, irrigate the shallow water layer, and drain and sow after 2~3d, when seedling stage treatment, when the rice seedling grows from one leaf and one heart to two leaves and one heart, use 5% emulsified oil 22.5 ~30mL/100m2 spray water, keep the shallow water layer for 3~4d.

Approximately 1.22 million pounds of thiobencarb are applied annually on 465,000 acres (460,000 of which is rice).

USEPA/OPP Pesticide Code 108401; Trade Names: Bencarb; Bolero; Saturn; B 3015; IMC 3950.|Emulsifiable concentrate, granule|Trade and Other Names: Bolero, Bencarb, Saturn, B 3015, IMC 3950.|Premix Partners: Bensulfuron-methyl; Propanil.|For more Formulations/Preparations (Complete) data for THIOBENCARB (12 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies Thiobencarb (technical grade) as Class II: moderately hazardous; Main Use: herbicide.|The technical grade is approximately 93% pure.

Method: NIOSH 5601, Issue 1; Procedure: high performance liquid chromatography with ultraviolet detection; Analyte: thiobencarb; Matrix: air; Detection Limit: 0.6 ug per sample.|Method: EPA-OGWDW/TSC 527; Procedure: gas chromatography-mass spectrometry; Analyte: thiobencarb; Matrix: drinking water; Detection Limit: 0.038 ug/L.|Method: USGS-NWQL O-1126-95; Procedure: gas chromatography-mass spectrometry with select-ion monitoring; Analyte: thiobencarb; Matrix: natural water; Detection Limit: 0.008 ug/L.|Product and residue analysis by gas liquid chromatography with flame ionization detector.

Agrochemicals -> Herbicides

Computed Properties

Molecular Weight:257.78
XLogP3:3.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:257.0641130
Monoisotopic Mass:257.0641130
Topological Polar Surface Area:45.6
Heavy Atom Count:16
Complexity:213
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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