55285-14-8 Usage
Description
Carbosulfan, also known as 2,3-dihydro-2,2-dimethylbenzofuran-7-yl(dibutylaminothio)methylcarbamate (IUPAC), is an orange to brown, clear viscous liquid with a boiling point of 124-128°C. It is miscible with organic solvents and has a low solubility of 0.3 ppm in water at 25°C. Structurally, it is closely related to carbofuran and functions as a cholinesterase inhibitor with systemic activity.
Uses
Used in Agriculture:
Carbosulfan is used as an insecticide for controlling a wide range of soil-dwelling and foliar pests. It is effective against pests in various crops such as cotton, sugar beet, potato, rice, fruit, maize, vegetables, sugar cane, and coffee.
Used in Insect Control:
Carbosulfan is used as a cholinesterase inhibitor with systemic activity for controlling pests like potato green peach aphid, black beetle, high dyed blind fly, cutworm, cotton spider mite, billbug, tribolium confusum, and spodoptera moth.
Used in Citrus and Fruit Trees:
Carbosulfan is used as a low toxic insecticide with internal absorbability and broad-spectrum properties for controlling pests such as aphids, mites, wireworm, beet, and potato beetles, as well as hidden food tea leafhopper, Grapholitha molesta, and codling moth in citrus, fruit trees, cotton, and rice crops.
Used in Vegetable and Grain Crops:
Carbosulfan is used as a low toxic insecticide with high absorbability and broad-spectrum properties for controlling rust ticks, aphids, thrips, leafhoppers, and more than 10 other kinds of pests on fruit trees, cotton, vegetables, and grain 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.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 55285-14-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,5,2,8 and 5 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 55285-14:
(7*5)+(6*5)+(5*2)+(4*8)+(3*5)+(2*1)+(1*4)=128
128 % 10 = 8
So 55285-14-8 is a valid CAS Registry Number.
InChI:InChI=1/C20H32N2O3S/c1-5-7-12-22(13-8-6-2)26-15-21-19(23)24-17-11-9-10-16-14-20(3,4)25-18(16)17/h9-11H,5-8,12-15H2,1-4H3,(H,21,23)
55285-14-8Relevant articles and documents
Preparation method of carbosulfan
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Paragraph 0040; 0043-0044; 0045; 0048-0049; 0050; 0053-0054, (2020/04/17)
The invention provides a preparation method of carbosulfan. The method comprises the following steps: (1) dissolving carbosulfan in an organic solvent, adding an acid-binding agent I triethylamine, performing stirring and mixing until uniformity, adding sulfur dichloride in a dropwise manner, and carrying out a thermal insulation reaction after the drop-by-drop addition is finished in order to prepare a sulfide solution; (2) adding di-n-butylamine, 4-dimethylaminopyridine and an acid-binding agent II triethylamine into the obtained sulfide solution, and, carrying out the thermal insulation reaction after the drop-by-drop addition is finished in order to obtain a carbosulfan reaction; and (3) washing the carbosulfan reaction solution until the reaction solution is neutral, separating out the obtained organic phase, and carrying out reduced pressure solvent removal to obtain the carbosulfan with the content of 96% or above, the yield of 98% or above and the harmful impurity carbofuran content of 0.1% or below. The method has the advantages of simplicity in operation, easily available raw materials and low cost, the prepared carbosulfan has the advantages of low content of main harmful impurities, high yield and high purity.
SYSTEM FOR PROTECTING GOODS DURING TRANSPORT
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, (2013/02/28)
A system for protecting stored goods in a container (10), comprises a cage-like structure (20) formed by at least one pesticide treated net (22), capable of enclosing the stored goods, wherein the cage like structure (20), further comprises means for suspending the pesticide treated nets (14, 28, 30, 32, 34), and means for opening and closing the cage-like structure (26) on at least one section (24) of the at least one net (22). The system is particularly useful for the transport of tobacco, coffee, dried fruits, cocoa, nuts, tea, cereals, vegetables, spices and animals.
Synthesis of N,N-dialkylaminosulfenylcarbamate insecticides via carbamoyl fluorides
Hatch III
, p. 3953 - 3957 (2007/10/09)
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