Carbosulfan Chemical Properties

Melting point:

<25 °C

Boiling point:

approximate 126℃

Density 

1.0560

vapor pressure 

3.1 x 10^-5 Pa (20 °C)

refractive index 

1.6360 (estimate)

Flash point:

96 °C

storage temp. 

0-6°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

3.15±0.70(Predicted)

form 

Liquid

Water Solubility 

0.3 mg l^-1 (25 °C)

color 

Light brown to brown

Merck 

13,1836

LogP

6.050 (est)

CAS DataBase Reference

55285-14-8(CAS DataBase Reference)

NIST Chemistry Reference

Carbamic acid, [(dibutylamino)thio]methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester(55285-14-8)

EPA Substance Registry System

Carbosulfan (55285-14-8)

Safety Information

Hazard Codes 

T;N,N,T,T+

Risk Statements 

23/25-43-50/53-26-25

Safety Statements 

24-37-38-45-60-61-63-36/37-28

RIDADR 

UN 2810

WGK Germany 

3

RTECS 

EZ3815000

HazardClass 

6.1(b)

PackingGroup 

III

Toxicity

LD50 in male, female rats (mg/kg): 250, 185 orally; in male, female rabbits (mg/kg): >2000, >2000 dermally; in pheasant, mallard, quail (ppm): 26.2, 8.1, 81.6 orally. LC50 (96 hr) in bluegill, trout (ppb): 14.9, 42.4 (Maitlen).

Carbosulfan Usage And Synthesis

Chemical properties

Brown sticky liquid. B.p. is124 ~ 128 ℃ (114 ℃). The flash point is 115~1,117℃, and the vapor pressure is 0.041 x 10-3Pa. The relative density is 1.056 (20℃). It can dissolve with acetone, ethanol and xylene, and the solubility in water is 0.3mg/L. The distribution coefficient is 157 (pH value is 7.05).
It has a fast decomposition in water, easily decomposed into carbofuran with pH<7. In the sun, when the 5 g/mL of Carbosulfan is in buffer solution with pH equaling to 7, the half-life period is 1.4d and 4 ~ 8d in distilled water.

Application

• This product is a derivative of carbofuran, which has the same insecticidal activity as carbofuran .But its toxicity is much lower than carbofuran, a stomach insecticide .It can be metabolized into carbofuran in the organism and then play its effect to kill the insect. It has excellent control effect on the potato green peach aphid, black beetle, high dyed blind fly, cutworm and other insects. In addition, it can also better control cotton spider mite, billbug, tribolium confusum and spodoptera moth etc..
• Carbamate insecticides, acaridants and nematides with high absorbability and broad-spectrum properties. It is a low toxic variety of Carbosulfan for the control of citrus, fruit trees, cotton and rice crops of aphids, mites, wireworm, beet and potato beetles, a hidden food tea leafhopper, Grapholitha molesta, codling moth and other pests. The administration concentration is 5mg/L and the effective component is 6.8 ~ 15g /100m2.
• Low toxic insecticides with internal absorbability and broad-spectrum
• For the control of rust ticks, aphids, thrips, leafhoppers and other more than 10 kinds of pests on the fruit trees, cotton, vegetables, grain and other crops.

Preparation Method

Preparation method 1:
Preparation of two n-butanamine sulphide Add two n-butyl amine and petroleum ether (60~90℃ ), mixing and cooling to 0℃ . Then slowly drip disulfur dichloride and maintain the temperature at 0~10 ℃. Afterwards, the reaction will be maintained at a constant temperature. The proportioning of the di-n-butylamine, disulfur dichloride and sulfuric chloride is 1:0.6:0.55(mol). The yield is 88%.
The synthesis of carbosulfan Two n-butanamine sulphur chloride reacts with carbosulfan with the ratio of 1:1. The reaction process is added with a proper amount of alkaline solution, and the reaction temperature is 10~20 ℃. The reaction time period is 2h. Add water and mix it for 10 minutes after the reaction. Filter it and the unreacted is carbosulfan which can be reused. The filtrate is stratified and the oil layer is decompressed and dissolving, and the yield is 90%.

Preparation method 2:
The synthesis of the intermediates hydroxyl compounds can be take the carbosulfan as reference. There are also literature reporting that starting from cyclohexanone and isobutyrate, five steps will be able to get it synthesized through condensation, chlorination, aromatization, hydrolysis and closed loop reaction. It is characterized by the synthesis of non aromatic compounds and is a highly selective synthesis route.

Category

Pesticides

Toxicity classification

Highly toxic

Acute toxicity

Oral administration-rats  LD50: 51 mg / kg;
Oral administration - mouse LD50: 74 mg / kg

Flammability

Combustible

Hazard Characteristics

Combustion can produce toxic nitrogen oxides and oxygen sulfide.

Storage and transportation

The storeroom is ventilated and dry at low temperature.
Separate transportation from food raw materials.

Extinguisher

Dry powder, foam, sand.

Description

Carbosulfan (8)，2,3-dihydro-2,2-dimethylbenzofuran- 7-yl(dibutylaminothio)methylcarbamate(IUPAC), is an orange to brown, clear viscous liquid (bp 124–128 ?C), miscible with organic solvents and solubility 0.3 ppm in water(25 ?C). It is closely related structurally to carbofuran,and like carbofuran, it is a cholinesterase inhibitor with systemic activity.

Chemical Properties

Orange-yellow thick liquid.

Uses

Carbosulfan is an insecticide with contact and stomach action. It is used to control a wide range of soil-dwelling and foliar pests in cotton, sugar beet, potato, rice, fruit, maize, vegetables, sugar cane and coffee.

Definition

ChEBI: Carbosulfan is a member of 1-benzofurans and a carbamate ester. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a carbamate insecticide, an acaricide, an agrochemical and a nematicide.

General Description

Viscous brown liquid.

Air & Water Reactions

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

Reactivity Profile

Carbosulfan 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.

Potential Exposure

Carbosulfan is a carbamate insecticide and a low toxic derivative from cabofuran. It is a broad spectrum insecticide, nematicide, miticide, effective against pests and mites. It is used to protect alfalfa, apple, citrus, corn, deciduous fruit, potato, rice, sorghum, soybean, sugar beets, sugarcane, and other vegetable, field, tree and orchard crops. It is used for seed treatments

Metabolic pathway

Carbosulfan is an N-sulfenyl-N-methylcarbamate which is effectively a pro-insecticide of carbofuran. The latter is formed in vivo by the biochemical or chemical thiolysis of carbosulfan. N-S Bond cleavage, oxidation, conjugation and hydrolysis are the main metabolic routes for carbosulfan in plants and animals. Carbosulfan is degraded via carbofuran in soil. In plants, carbosulfan is metabolised via carbofuran to 3-hydroxycarbofuran (PM).

Metabolism

Itsmetabolic patterns are similar to those of carbofuran. In rats, it rapidly undergoes hydrolytic and oxidative processes followed by conjugation. It is not persistent in soils, with DT₅₀ ca. 2–5 days, and it was rapidly degraded to carbofuran in a sandy loam soil (4). Carbofuran was subsequently hydrolyzed at the carbamate ester group to form the phenol carbofuran or oxidized at the 3- position. Biscarbofuran disulfide and minor products were also detected. Carbofuran was also formed in soils by nonbiological degradation processes.

Shipping

UN2992 Carbamate pesticides, liquid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials; UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Degradation

Carbosulfan is hydrolysed in aqueous media most rapidly under acidic conditions. Its DT₅₀ values (25 °C) at pH 4,6 and 7 were <1 hour, 22 hours and 7.6 days respectively (PM). In a variety of aqueous solvents there was facile cleavage of the N-S carbamate bond of carbosulfan to yield carbofuran (2) as the sole or major product (see Scheme 1) (Umetsu et al., 1980). A solution of [¹⁴C]carbosulfanin propylene glycol was treated with 0.001 or 0.01 N aqueous HCl at 40 °C. Solutions were analysed at intervals up to 24 hours. Carbosulfan was relatively stable with more than 40% being recovered after 24 hours in the solution of lower acidity. Carbofuran (2) was the principal transformation product in hydrochloric acid. Biscarbofuran disulfide (3) was present in only trace amounts and small amounts of polysulfides of carbosulfan (4,n = 2-6) were detected (Umetsu and Fukuto, 1982).
Carbosulfan was quite stable in neutral and alkaline media. [¹⁴C-carbonyl]- or [¹⁴C-dibutylamino]Carbosulfan dissolved in dichloromethane: acetic acid (9:l) converted to a range of products via N-S bond cleavage. The principal products were carbofuran (2), dibutylamine and a mixture of polysulfide derivatives: bis-carbofuran disulfide (3) and a mixture of bis-carbofuran polysulfides (5). Structures of products were confirmed by MS and NMR (Umetsu et al., 1981a,b).

Incompatibilities

Carbamates are incompatible with strong oxidizing acids, peroxides, and hydro-peroxides; strong reducing agents such as hydrides; strong acids and bases. Contact with nitrides or chemically active metals (aluminum, copper, magnesium, neptunium, sodium, tin, titanium,zinc, etc.) causes the release of potentially explosive hydrogen gas and a metal salt.

Waste Disposal

Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Incineration with effluent gas scrubbing is recommended. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Noncombustible containers should be crushed and buried under more than 40 cm of soil. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

Carbosulfan(55285-14-8)Related Product Information

• BENFURACARB
• tert-Butyldimethylsilyl chloride
• Urethane
• Methyl 4-tert-butylbenzoate
• N,N-Dimethyl-1,4-phenylenediamine
• POLYURETHANE
• 4-Aminobenzoic acid
• Dihydromyrcenol
• Anthranilic acid
• Carbofuran
• METOLCARB
• 2,3-Dihydro-2,2-dimethyl-7-benzofuranol
• Propoxur
• Carbosulfan
• (-)-MENTHYL CHLOROFORMATE
• Methyl carbamate
• o-hydroxyphenyl methylcarbamate
• 2,3-dihydro-2,2-dimethylbenzofuran