1563-66-2 Usage
Description
Carbofuran, also known as Furadan, is a broad-spectrum N-methyl carbamate insecticide and nematicide. It is an odorless, white crystalline solid that is toxic by inhalation, skin contact, and/or ingestion. Carbofuran is used as a pesticide, primarily for controlling a variety of insect pests on field, fruit, and vegetable crops.
Uses
Used in Agricultural Industry:
Carbofuran is used as an insecticide, acaricide, and nematicide for controlling soil-dwelling and foliar-feeding insects, mites, and nematodes on field, fruit, and vegetable crops. It is effective against pests such as aphids, thrips, and nematodes that attack a wide range of crops, including sunflower, potatoes, peanuts, soybeans, sugar cane, cotton, rice, and various other crops.
Used in Chemical Industry:
Carbofuran is used as a broad-spectrum, systemic insecticide, nematicide, and acaricide. It is applied in soil to control soil insects and nematodes or on foliage to control insects and mites. The chemical is a restricted use pesticide, with nearly 1 million pounds of active ingredient almost exclusively used on corn, alfalfa, and potatoes.
Used in Environmental Protection:
The U.S. Environmental Protection Agency (EPA) prohibited the use of carbofuran granules in 1994 due to their association with bird kills. This action aimed to protect the environment and reduce the negative impact of carbofuran on avian populations.
Chemical Properties:
Carbofuran is a white crystal-like solid that is slightly soluble in water and stable under neutral and acidic conditions. However, it decomposes under alkaline conditions. On heating, it breaks down and can release toxic fumes and irritating or poisonous gases. It is sparingly soluble in water but very soluble in acetone, acetonitrile, benzene, and cyclohexone. The liquid formulations of carbofuran are classified as restricted use pesticides (RUP) due to their acute oral and inhalation toxicity to humans. Granular formulations are also classified as RUP.
Environmental Fate
Carbofuran is highly mobile in soils and can leach into groundwater and enters surface water as runoff. The chemical breaks down though hydrolysis, photodegradation, and moderate bacterial degradation at rates that depend on environmental conditions. Hydrolysis is faster in water with a pH 7, with a half-life ranging from a few hours to 28 days. Carbofuran is stable to hydrolysis in acidic water. Photodegradation is fast in a thin water layer, with a halflife of 6 days. In the top few millimeters of a sandy loam soil, carbofuran degrades in 78 days. Bioconcentration is not expected to occur (U.S. EPA, 2006a).
Environmental Fate
Carbofuran is soluble in water and is moderately persistent in soil. Its half-life is 30–120 days. It enters surface water as a result of runoff from treated fields and enters groundwater by leaching of treated crops. If released to soil, degradation occurs by chemical hydrolysis and biodegradation. The persistence of carbofuran in the soil increases as the clay and organic matter content of the soil increase, and as the pH and moisture content of soil decrease. Chemical hydrolysis occurs more rapidly in alkaline soil as compared to neutral or acidic soils. Carbofuran is likely to leach to groundwater in soils with low organic content. Volatilization from soil is not expected to be significant, although some evaporation from plants may occur. If released to water, carbofuran degrades by hydrolysis under alkaline conditions and by biodegradation. Aquatic volatilization, adsorption, and bioconcentration are not expected to be important.
References
[1] S. Bretaud, J. -P. Toutant and P. Sagilo, Effects of Carbofuran, Diuron, and Nicosulfuron on Acetylcholinesterase Activity in Goldfish (Carassius auratus), Ecotoxicology and Environmental Safety, 2000, vol. 47, 117-124
[2] Dennis M. Trotter, Robert A. Kent and Michael P. Wong, Aquatic fate and effect of Carbofuran, Critical Reviews in Environmental Control, 1991, vol. 21, 137-176
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
Carbofuran is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates. Carbofuran is unstable in an alkaline media. .
Health Hazard
The acute oral LD50 of carbofuran to male and female rats is about 8 mg/kg, while the acute dermal LD50 for rats is more than 3000 mg/kg. Carbofuran is mildly irritating to the eyes and skin of rabbits. The acute inhalation toxicity (LC50, 4 h) is 0.075 mg/L for rats. As with other carbamate compounds, carbofuran’s cholinesterase-inhibiting effect is short term and reversible. The symptoms of carbofuran poisoning include, but are not limited to, nausea, vomiting, abdominal cramps, sweating, diarrhea, excessive salivation, weakness, imbalance, blurring of vision, breathing diffi culty, increased blood pressure, and incontinence. Death may result at high doses from respiratory system failure associated with carbofuran exposure. Complete recovery from an acute poisoning by carbofuran, with no long-term health effects, is possible if exposure ceases and the victim has time to regain his or her normal level of cholinesterase and to recover from symptoms. Reports have indicated that risks from exposure to carbofuran are especially high among occupational workers and general public suffering with asthma, diabetes, cardiovascular disease, gastrointestinal or urogenital tracts disturbances. The available studies indicate carbofuran is unlikely to cause reproductive effects in humans at expected exposure levels. Studies indicate carbofuran is not teratogenic. No signifi cant teratogenic effects have been found in the offspring of rats given carbofuran (3 mg/kg/day) on days 5 to 19 of gestation.
Fire Hazard
May release nitrogen oxides. Containers may explode in heat of fire. Avoid alkalies. Stable under neutral or acid conditions.
Trade name
A13-27164?; AU'ULTRAMICIN?; BAY 704143?; BAY 78537?; BRIFUR?; CARBODAN?;
CARBOSIP 5G?; CRISFURAN?; CURETERR?; CHINUFUR?; D 1221?; DIAFURAN?; FMC 10242?; FURACARB?; FURADAN?; FURAN?; FURODAN?; KENFURAN?; KENOFURAN?; NEX?; NIA10242; NIAGARA 10242; NIAGARA NIA-10242; PILLARFURAN?; RAMPART?; YALTOX?
Contact allergens
It is a pesticide with insecticide properties, of the carbamate
group. It was implicated as a sensitizer in two farmers
Safety Profile
to decomposition it emits toxic fumes of
Potential Exposure
A potential danger to those involved
in the manufacture, formulation, and application of this
insecticide, acaricide, and nematocide.
Metabolic pathway
The fate of carbofuran has been investigated in soils, plants, mammals,
birds, fish and insects. Metabolic pathways include hydrolysis, oxidation
(ring and N-methyl hydroxylation) and conjugation. The metabolism of
carbofuran has been extensively reviewed by Schlagbauer and Schlagbauer
(1972) and Kuhr and Dorough (1976). Metabolism in economic
animals was reviewed by Akhtar (1985). Consequently the many primary
publications are not usually cited.
Metabolism
Carbofuran (1) is degraded by hydrolysis and oxidation
in soil before ultimate mineralization . The
rate of hydrolysis in soils is slightly higher under flooded
than under nonflooded conditions. Products depend on
the soil type and the prevalence of aerobic or anaerobic
conditions, and it was also reported that carbofuran
did not degrade under anaerobic conditions. The products,
3-hydroxycarbofuran (2) and 3-ketocarbofuran (3), have
been isolated from soil extracts after incubation with carbofuran.
The phenol (7) was identified as a major product
in several studies. The products are further degraded and
bound to soil organic matter. Enhanced degradation may
follow repeated applications of carbofuran to soils, and
bacterial cultures capable of rapidly degrading carbofuran
have been obtained from treated soils.
storage
Carbofuran should be stored in a cool, dry, well-ventilated place, in their original containers only. It should not be kept stored or used near heat, open flame, or hot surfaces
Shipping
UN2757 Carbamate pesticides, solid, toxic,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN
2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1;
Labels: 6.1-Poisonous materials, Technical Name RequiredUN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1;
Labels: 6.1-Poisonous materials, Technical Name Required
Toxicity evaluation
Carbofuran undergoes hydrolytic and oxidative processes
in mammals. In rats, about 72% of the administered
dose was eliminated in the urine within 24 hours
as conjugated metabolites, mainly as conjugates of the 3-
ketocarbofuran phenol (5). The products of metabolism in
plants are 3-hydroxycarbofuran (4) and 3-ketocarbofuran
phenol (5).
Degradation
Carbofuran (1) is very stable in weakly acidic media and has a DT50 of
<1 year at pH 4 (22°C). It is stable in neutral media but unstable in
basic conditions (PM). Carbofuran was hydrolysed to the phenol (5) with
a half-life of 67 minutes at 37.5 °C at pH 9.5. 3-Ketocarbofuran (3)
and N-hydroxymethylcarbofuran (4) (Scheme 2) were hydrolysed faster
than carbofuran in alkaline solution (Metcalf et al., 1968). Unlabelled
carbofuran was dissolved in water and irradiated by sunlight in India
for 30 days. Samples were extracted and analysed by GC and TLC.
Products were 3-ketocarbofuran (3) and the 4-hydroxycarbofuran phenol
(8). (Raha and Das, 1990). Solid carbofuran was applied to glass plates
and irradiated with fluorescent light or sunlight. 3-Hydroxycarbofuran
(2) was detected after 2 days; 3-ketocarbofuran (3) was not detected
(Metcalf et al., 1968). These pathways are illustrated in Scheme 1.
Incompatibilities
Alkaline substances, acid, strong oxidizers, such as perchlorates, peroxides, chlorates, nitrates,
permanganates.
Waste Disposal
Alkaline hydrolysis is the
recommended mode of disposal. In accordance with
40CFR165, follow recommendations for the disposal of
pesticides and pesticide containers. 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.
Precautions
During use/handling of carbofuran, workers should wear coveralls or a long-sleeved
uniform, head covering, and chemical protective gloves made of materials such as rubber, neoprene, or nitrile. Occupational workers should know that areas treated with carbofuran are hazardous. The runoff of carbofuran material and the fi re control releases
irritating or poisonous gases. It is advisable that workers should enter storehouses or
carbofuran-treated close spaces with caution
Check Digit Verification of cas no
The CAS Registry Mumber 1563-66-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,6 and 3 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1563-66:
(6*1)+(5*5)+(4*6)+(3*3)+(2*6)+(1*6)=82
82 % 10 = 2
So 1563-66-2 is a valid CAS Registry Number.
InChI:InChI=1/C12H15NO3/c1-12(2)7-8-5-4-6-9(10(8)16-12)15-11(14)13-3/h4-6H,7H2,1-3H3,(H,13,14)
1563-66-2Relevant articles and documents
Metabolism of carbosulfan II. Human interindividual variability in its in vitro hepatic biotransformation and the identification of the cytochrome P450 isoforms involved
Abass, Khaled,Reponen, Petri,Mattila, Sampo,Pelkonen, Olavi
experimental part, p. 163 - 173 (2011/10/19)
This study aims to characterize interindividual variability and individual CYP enzymes involved in the in vitro metabolism of the carbamate insecticide carbosulfan. Microsomes from ten human livers (HLM) were used to characterize the interindividual variability in carbosulfan activation. Altogether eight phase I metabolites were analyzed by LC-MS. The primary metabolic pathways were detoxification by the initial oxidation of sulfur to carbosulfan sulfinamide ('sulfur oxidation pathway') and activation via cleavage of the nitrogen sulfur bond (N-S) to give carbofuran and dibutylamine ('carbofuran pathway'). Differences between maximum and minimum carbosulfan activation values with HLM indicated nearly 5.9-, 7.0, and 6.6-fold variability in the km, Vmax and CLint values, respectively. CYP3A5 and CYP2B6 had the greatest efficiency to form carbosulfan sulfinamide, while CYP3A4 and CYP3A5 were the most efficient in the generation of the carbofuran metabolic pathway. Based on average abundances of CYP enzymes in human liver, CYP3A4 contributed to 98% of carbosulfan activation, while CYP3A4 and CYP2B6 contributed 57 and 37% to detoxification, respectively. Significant correlations between carbosulfan activation and CYP marker activities were seen with CYP3A4 (omeprazole sulfoxidation), CYP2C19 (omeprazole 5-hydroxylation) and CYP3A4 (midazolam 1′-hydroxylation), displaying r2=0.96, 0.87 and 0.82, respectively. Activation and detoxification pathways were inhibited by ketoconazole, a specific CYP3A4 inhibitor, by 90-97% and 47-94%, respectively. Carbosulfan inhibited relatively potently CYP3A4 and moderately CYP1A1/2 and CYP2C19 in pooled HLM. These results suggest that the carbosulfan activation pathway is more important than the detoxification pathway, and that carbosulfan activation is predominantly catalyzed in humans by CYP3A4.
PESTICIDAL COMPOSITIONS
-
, (2008/06/13)
Composition for controlling insects and representatives of the order Acarina, which comprises a combination of variable amounts of one or more compounds of the formula in which A is an unsubstituted or, depending on the possibility of substitution on the ring system, mono- to tetrasubstituted, aromatic or non-aromatic monocyclic or bicyclic heterocyclic radical, in which the substituents of A can be chosen from the group consisting of C1-C3alkyl, C1-C3alkoxy, halogen, halo-C1-C3alkyl, cyclopropyl, halocyclopropyl, C2-C3alkenyl, C2-C3alkynyl, halo-C2-C3alkenyl, halo-C2-C3alkynyl, halo-C1-C3alkoxy, C1-C3alkylthio, Halo-C1-C3alkylthio, allyloxy, propargyloxy, allylthio, propargylthio, haloallyloxy, haloallylthio, cyano and nitro; R is hydrogen, C1-C6alkyl, phenyl-C1-C4alkyl, C3-C6cycloalkyl, C2-C6alkenyl or C2-C6alkynyl; and X is N—NO2 or N—CN, in the free form or in salt form, if appropriate tautomers, in the free form or salt form, and one or more of the compounds (I) to (CLXXXIV) mentioned according to the invention and at least one auxiliary. A method of controlling pests, a process for the preparation of the composition, its use and plant propagation material treated with it, and the use of the compound of the formula (A) for the preparation of the composition, are described.
Macrocyclic plant acaricides
-
, (2008/06/13)
Compounds of the formula I STR1 in which either R is methyl and there is a double bond in the 9,10-position, or in which R is hydrogen and there is a single bond in the 9,10-position, are highly active against Acarina which damage plants.
