Nature
Carbofuran, molecular formula C12H15NO3, white crystalline Carbofuran, molecular formula C12H15NO3, white crystalline . 33 DEG C has a vapor pressure of 2.66 -
6kPa in acetone solubility of 15%, 14% in acetonitrile, benzene, and 4%, 9% in cyclohexanone, dimethyl sulfoxide (DMSO) in 25%, 27% in dimethylformamide, methylpyrrolidone 30% 6kPa in acetone solubility of 15%, 14% in acetonitrile, benzene, and 4%, 9% in cyclohexanone, dimethyl sulfoxide (DMSO) in 25%, 27% in dimethylformamide, methylpyrrolidone 30% . 1 is non - corrosive heat; light; acid was stable, but unstable in an alkaline medium, tasteless, odorless 1 is non - corrosive heat; light; acid was stable, but unstable in an alkaline medium, tasteless, odorless .
in neutral, alkaline conditions are relatively stable, readily hydrolyzable in alkaline medium failure in neutral, alkaline conditions are relatively stable, readily hydrolyzable in alkaline medium failure . pH 5. 2 when a half - life of 1600d (25. degree. C.);pH 7 when a half - life of 28 - 28d); the pH value of 9 with a half - life (7h 26. degree. C.) 
Toxicological Data
no teratogenicity, carcinogenicity and mutagenicity, to second - generation reproduction test and toxicity test in nerve abnormalities in the no teratogenicity, carcinogenicity and mutagenicity, to second - generation reproduction test and toxicity test in nerve abnormalities in the .
Mode Synthesis
1. Starting from o - nitrophenol: chlorination reaction: isopropenyl chloride under pressure, to obtain methyl chloro propylene chloride reaction product is treat through press filtering, distillation, etc., aftertreatment, the product purity can reach 96%
etherification reaction: o - nitrophenol and methyl allyl chloride in the presence of sodium carbonate to produce 2 - methallyl - 2 - nitro phenol ether etherification reaction: o - nitrophenol and methyl allyl chloride in the presence of sodium carbonate to produce 2 - methallyl - 2 - nitro phenol ether . Clay Thompson reaction: 2 - methallyl - 2 - nitro phenol ether is heated, by Clare Macpherson transposition reaction generates a 2 - (2 - methallyl) - 6 - nitrophenol Clay Thompson reaction: 2 - methallyl - 2 - nitro phenol ether is heated, by Clare Macpherson transposition reaction generates a 2 - (2 - methallyl) - 6 - nitrophenol .
cyclization reaction: in the presence of anhydrous magnesium chloride, Clay Thompson rearrangement product ring synthesis 2 - 2,3 - dihydro - 2,2 - dimethyl - 7 - nitro - 7 - nitro - benzofuran ( cyclization reaction: in the presence of anhydrous magnesium chloride, Clay Thompson rearrangement product ring synthesis 2 - 2,3 - dihydro - 2,2 - dimethyl - 7 - nitro - 7 - nitro - benzofuran (.): hydrogenation of 7 - nitro in the presence of a palladium / carbon catalyst, the pressure - reduced to produce 2, 3 - dihydro - 2,2 - dimethyl - 7 - amino - benzofuran (commonly known as 7 - amino -) ): hydrogenation of 7 - nitro in the presence of a palladium / carbon catalyst, the pressure - reduced to produce 2, 3 - dihydro - 2,2 - dimethyl - 7 - amino - benzofuran (commonly known as 7 - amino -) .
diazotization reaction: 2 - amino - 6 - 7 with an aqueous solution of sodium nitrite in concentrated sulfuric acid and the diazotizing reaction, 2 -, 3 - dihydro - 2,2 - dimethyl - 7 - benzofuran - 7 - diazonium sulfate (diazonium sulfate) diazotization reaction: 2 - amino - 6 - 7 with an aqueous solution of sodium nitrite in concentrated sulfuric acid and the diazotizing reaction, 2 -, 3 - dihydro - 2,2 - dimethyl - 7 - benzofuran - 7 - diazonium sulfate (diazonium sulfate) . hydrolysis: 7 - diazonium sulfate CuSO4 under the catalysis of the hydrolysis into the 2 -, 3 - dihydro - 2,2 - dimethyl - 7 - hydroxybenzofuran (known as the 7 - hydroxyl compound to carbofuran) hydrolysis: 7 - diazonium sulfate CuSO4 under the catalysis of the hydrolysis into the 2 -, 3 - dihydro - 2,2 - dimethyl - 7 - hydroxybenzofuran (known as the 7 - hydroxyl compound to carbofuran) .
synthesis: A mixture of 7 - hydroxyl compounds and methyl isocyanate in a solvent, a small amount of triethylamine in the presence of carbofuran synthesis: A mixture of 7 - hydroxyl compounds and methyl isocyanate in a solvent, a small amount of triethylamine in the presence of carbofuran . 2. also can adopts methylaminoformyl chloride method, put the MCC at 55.d egree. C. was added dropwise to 7 - hydroxy compound in a yield of 97%
by catechol: this process route is catechol in anhydrous acetone in a solvent, in the presence of K2CO3, KI, and methyl allyl chloride by heating a 2 - propoxy - phenol, and then heating the indexing,Cyclization to give 7 - hydroxy compound in the presence of triethylamine and then by catechol: this process route is catechol in anhydrous acetone in a solvent, in the presence of K2CO3, KI, and methyl allyl chloride by heating a 2 - propoxy - phenol, and then heating the indexing,Cyclization to give 7 - hydroxy compound in the presence of triethylamine and then . isocyanate synthesis method using carbofuran isocyanate synthesis method using carbofuran .
functions as follows: 2 - allyl phenol oxidation preparation under nitrogen, 40 parts by mass) of potassium carbonate and potassium iodide (481 parts by mass) was added slowly to a stirred mixture of 322 (parts by mass) of catechol and 300 parts by mass) solution of anhydrous acetone ( functions as follows: 2 - allyl phenol oxidation preparation under nitrogen, 40 parts by mass) of potassium carbonate and potassium iodide (481 parts by mass) was added slowly to a stirred mixture of 322 (parts by mass) of catechol and 300 parts by mass) solution of anhydrous acetone (. in the resulting material was heated to reflux temperature, slowly added 262 parts by mass (meth) allyl chloride in the resulting material was heated to reflux temperature, slowly added 262 parts by mass (meth) allyl chloride .
reaction the mixture was refluxed for 30 hours, and cooled and allowed to stand 18 h, filtered and the filtrate is concentrated under reduced pressure,the residual oil was extracted with chloroform and washed with water, dried, concentrated, and the residual oil by vacuum distillation (213 parts by mass) of 2 - allyl phenol 7 reaction the mixture was refluxed for 30 hours, and cooled and allowed to stand 18 h, filtered and the filtrate is concentrated under reduced pressure,the residual oil was extracted with chloroform and washed with water, dried, concentrated, and the residual oil by vacuum distillation (213 parts by mass) of 2 - allyl phenol 7 . oxo - hydroxy compound in the preparation of the 131 parts by mass) (2 - methallyl - oxo transposition phenol cyclization at 200 c, the heat of the exothermic reaction occurs, to rapidly reach and maintain a temperature of 275.d egree. C. to obtain a thick syrup, reduced - pressure distillation to obtain colorless 2 -, 2 - dimethyl - 2,3 - dihydro - benzofuran - 7 - hydroxy compound (7 - hydroxy - carbofuran)
Synthesis:16. 6 parts by mass) (7 - hydroxyl compound in parts by mass (14) of the diethyl ether with 5. 8 parts by mass of isocyanate (formic acid) and 0.1 parts by mass of triethylamine, the mixture was stirred at room temperature, the precipitated product as a white crystalline solid was isolated by crystallization , 17.9 parts of carbofuran 
Preparation Method
ortho - nitrophenol with 3 - chloro - isobutene prepared by the reaction of the isobutene and 2 - nitrobenzene, and then at 175 to 190. degree. C. is subjected to a Claisen rearrangement, 150 to 190 degrees C. for the cyclisation reaction of the acidic catalyst is ferric chloride (III), 2 -, 3 - dihydro - 2,2 - dimethyl - 7 - nitro - benzofuran, followed by hydrogenation, and then at room temperature or low temperature, the sulfuric acid and sodium nitrite in the presence of a diazotizing reaction, heating is hydrolyzed to 3 - 7 - hydroxy benzofuran, again with methyl isocyanate by the reaction of carbofuran 75% powder. Said invented product is generally made, in the form of particle
2 2.
Main Uses
Carbofuran is an urethane - type broad - spectrum systemic insecticides, miticides and nematicides, liquid for preventing and treating soil in the ground and on the surface of the over 300 kinds of pests and nematode Carbofuran is an urethane - type broad - spectrum systemic insecticides, miticides and nematicides, liquid for preventing and treating soil in the ground and on the surface of the over 300 kinds of pests and nematode . and shortened the growing season of crops; promote crop growth and development so as to effectively improve crop yield and shortened the growing season of crops; promote crop growth and development so as to effectively improve crop yield .
carbofuran on insect aquatic toxicity, mainly systemic pesticidal action carbofuran on insect aquatic toxicity, mainly systemic pesticidal action . agent applied to the soil to the root portion of the crop, roots after absorbing moisture transported with the stalk, in order to achieve the purpose of the vermin; Carbofuran also has contact toxicity for agent applied to the soil to the root portion of the crop, roots after absorbing moisture transported with the stalk, in order to achieve the purpose of the vermin; Carbofuran also has contact toxicity for .
sum - mer cotton aphis, rice, corn, rice or corn, peanut and other crop pests most effective sum - mer cotton aphis, rice, corn, rice or corn, peanut and other crop pests most effective . 3 3.
Using The Method
(1) preventing and treating cotton seedling pest per mu with 3% Granule 1.5 ~ 2 kilograms, while the seed is scattered into the sulcus, or with 3% cottonseeds dry mixed granules, the dosage is administered 1, 2 and 3, a cottonseed 4 (2) preventing and controlling tobacco pests Tian: Control of Myzus persicae in tobacco, Meloidogyne spp., Agrotis ypsilon Rottemberg, Gryllotalpidae etc to tobacco seedling transplant, with 3% granules per hole and spread 1 1. 5 grams
(3) preventing and controlling rice pests: the prevention of rice moth, planthopper, thrips, leafhoppers, gall midge and other pests, mu with 3% Granule 1.5 ~ 2 kilograms, 15 kilograms of sand, Mix was removed from the water surface;Lu mu in rice field with 3% Granule 2 ~ 2. 5 kg, and the rice seeds are sown at the same time (4) controlling pest of soybean plants: aphids, flies and bean cyst nematode and the like, with 3% Granule 2. 2 ~ 4. 4 kilograms,
within the seed furrow (5) in peanut field pests: aphids, thrips, mole crickets and root knot nematode, etc within the seed furrow (5) in peanut field pests: aphids, thrips, mole crickets and root knot nematode, etc . mu with 3% Granule 4 - 5 kg, and of the growing season of crops within the seed furrow or interline - duster after ditching mu with 3% Granule 4 - 5 kg, and of the growing season of crops within the seed furrow or interline - duster after ditching .
soil cover (6): "first, carbofuran and high toxicity, and steric effect; this medication is not diluted with water and spraying the second soil cover (6): "first, carbofuran and high toxicity, and steric effect; this medication is not diluted with water and spraying the second ., rice paddies, not with propanil,swep and mix; propanil should be used when the use of carbofuran in 4 days before use or after use of carbofuran 1 month , rice paddies, not with propanil,swep and mix; propanil should be used when the use of carbofuran in 4 days before use or after use of carbofuran 1 month .
Safety
Emergency Treatment
Skin Contact: Remove contaminated clothes and wash with large quantity of flowing clean water Skin Contact: Remove contaminated clothes and wash with large quantity of flowing clean water . Eye contact: Uplift the eyelids, rinse them with flowing fresh water or physiological saline hospitalizing Eye contact: Uplift the eyelids, rinse them with flowing fresh water or physiological saline hospitalizing .
. Inhalation: remove to fresh air quikly Inhalation: remove to fresh air quikly .
. keep respiratory tract unobstructed.Such as difficulty breathing, give oxygen. "
As breathing stops, conduct artificial respiration immediately hospitalized As breathing stops, conduct artificial respiration immediately hospitalized . .
Ingestion: Drink as ample water, emetic and gastrolavage Ingestion: Drink as ample water, emetic and gastrolavage ., , .
. Purgation, hospitalized for respiratory protection: it is possible to contact the dust, must wear a dust mask (full mask) Purgation, hospitalized for respiratory protection: it is possible to contact the dust, must wear a dust mask (full mask) .
rescuing or evacuating during emergent situation, wear air respirators rescuing or evacuating during emergent situation, wear air respirators . Eye protection: eyes have been protected in the respiratory system protection Eye protection: eyes have been protected in the respiratory system protection .
body protection:companion GJBZ063 body protection:companion GJBZ063 . Hand protection: wear rubber gloves Hand protection: wear rubber gloves .
Other protections: No smoking, eating and drinking at the work site Other protections: No smoking, eating and drinking at the work site . work completed, shower and dress good hygiene work completed, shower and dress good hygiene .
. Emergency leakage treatment: isolate the contaminated area with access limitation, cut off fire Emergency leakage treatment: isolate the contaminated area with access limitation, cut off fire .
. It's suggested that emergency treatment staff wear positive - pressure inhaler and gas - protection suit It's suggested that emergency treatment staff wear positive - pressure inhaler and gas - protection suit .
collect the dust with clean shovel and hold in dry, clean and covered vessels, transfer to the safer place collect the dust with clean shovel and hold in dry, clean and covered vessels, transfer to the safer place . if significant quantities of leakage, be collected for recycling or transported to a waste disposal plant for disposal if significant quantities of leakage, be collected for recycling or transported to a waste disposal plant for disposal .
hazardous combustion products: carbon monoxide, carbon dioxide, nitrogen oxide hazardous combustion products: carbon monoxide, carbon dioxide, nitrogen oxide . fire - extinguishing method: fire - fighting staff shall wear mask,In a safe distance, and put on a fire fire - extinguishing method: fire - fighting staff shall wear mask,In a safe distance, and put on a fire .
Extinguishing agents: fog water, foam, dry chemical, carbon dioxide, and sand Extinguishing agents: fog water, foam, dry chemical, carbon dioxide, and sand . 4 4.
The Impact On The Environment
a health hazards, Pathways: inhaled, ingested, percutaneous absorption a health hazards, Pathways: inhaled, ingested, percutaneous absorption . health hazard: mainly inhibits cholinesterase activity in vivo, of acetylcholine in the tissue and cause toxic accumulation in the health hazard: mainly inhibits cholinesterase activity in vivo, of acetylcholine in the tissue and cause toxic accumulation in the .
CIA and CIA and . similar organophosphorus pesticide poisoning. The poisoning manifestations are salivation, lacrimation, miosis, and spasm but
organophosphorus pesticides andorganophosphorus pesticides compared to inhibition of cholinesterase of action lasts for a shorter time organophosphorus pesticides andorganophosphorus pesticides compared to inhibition of cholinesterase of action lasts for a shorter time . after discontinuing contacting of choline ester recovered after discontinuing contacting of choline ester recovered .
2, toxicology and environmental behavioral toxicity: peroral is highly toxic; percutaneous moderate class 2, toxicology and environmental behavioral toxicity: peroral is highly toxic; percutaneous moderate class . .
use has given rise to highly toxic in acute toxicity: LD505. 3mg / kg (Rat per os);Rabbit 885mg / kg (percutaneous); 10 g / kg (percutaneous); LC5085ppm 2 hours (mammalian) animal inhalation; 8 ~ 14 mg / kg (in mice after a single dose); metabolism: primarily via the port and into the body via the skin, the in vivo distribution, metabolism and speed quickly, after absorption is mainly distributed in the blood, liver, kidney and fat tissue with part by the liver, hydrolysis, oxidation and conjugation with glucuronic acid; detoxification; part of the prototype or a metabolite of the style is not eliminated by the kidneys, the 24 h conversion was 70% ~ 90%, with the urine and feces from part by the liver, hydrolysis, oxidation and conjugation with glucuronic acid; detoxification; part of the prototype or a metabolite of the style is not eliminated by the kidneys, the 24 h conversion was 70% ~ 90%, with the urine and feces from .
poisoning mechanism:This body topography similar to acetylcholine, the drugs enter the body, with the active serine hydroxyl group form the amino formylation cholinesterase, cholinesterase activity is lost so that, as a result of the great accumulation of acetylcholine, which caused a series of clinical symptoms of poisoning mechanism:This body topography similar to acetylcholine, the drugs enter the body, with the active serine hydroxyl group form the amino formylation cholinesterase, cholinesterase activity is lost so that, as a result of the great accumulation of acetylcholine, which caused a series of clinical symptoms of . cholinesterase function has its own characteristics: there is no need for activation, can be directly combined with the cholinesterase, erythrocyte and nerve synapses and true affinity than plasma pseudocholinesterase is strong; it to the whole of the molecule with the binding of cholinesterase and the complexes are complexes of a loose, not a true chemical bonding,but as a complex process involving iodocyclocarbamylation of cholinesterase is reversible, and can be rapidly hydrolyzed, is restored to have the activity of cholinesterase, generally 24 h can be automatically restored, without the "aging" of the problem; Oxime usually cannot promote inhibition of the enzyme complex can be, but is prevented in the urethanization of cholinesterase complex can cholinesterase function has its own characteristics: there is no need for activation, can be directly combined with the cholinesterase, erythrocyte and nerve synapses and true affinity than plasma pseudocholinesterase is strong; it to the whole of the molecule with the binding of cholinesterase and the complexes are complexes of a loose, not a true chemical bonding,but as a complex process involving iodocyclocarbamylation of cholinesterase is reversible, and can be rapidly hydrolyzed, is restored to have the activity of cholinesterase, generally 24 h can be automatically restored, without the "aging" of the problem; Oxime usually cannot promote inhibition of the enzyme complex can be, but is prevented in the urethanization of cholinesterase complex can .
therefore, this class of acute pesticide poisoning not use Oxime therefore, this class of acute pesticide poisoning not use Oxime . .
carbofuran is belong to highly toxic pesticide on the environmental organisms toxicity is also high, and in a variety of organisms in the environment, to birds, carbofuran, furadan foraging bird as long as a sufficient lethal carbofuran is belong to highly toxic pesticide on the environmental organisms toxicity is also high, and in a variety of organisms in the environment, to birds, carbofuran, furadan foraging bird as long as a sufficient lethal . furan by the poisoning of birds or other insects,are of birds, small mammals or reptiles after foraging, secondary poisoning can cause lethal furan by the poisoning of birds or other insects,are of birds, small mammals or reptiles after foraging, secondary poisoning can cause lethal .
in the United States found that more than 30 birds of prey (eagles, falcons, vultures) carbofuran. one carbofuran - secondary poisoning accident another environmental behavior characteristics is its residue in the soil of its long half - life (1 ~ 2 months), and movement in soil properties (water solubility and 700mg / L), in the precipitation, the groundwater level is shallow sandy areas and it is easy to be polluted, for the purpose of the United States on carbofuran use some local bans another environmental behavior characteristics is its residue in the soil of its long half - life (1 ~ 2 months), and movement in soil properties (water solubility and 700mg / L), in the precipitation, the groundwater level is shallow sandy areas and it is easy to be polluted, for the purpose of the United States on carbofuran use some local bans .
Medical Emergency
(1) which has been diagnosed as having excessive cholinergic nerve excitement of (1) which has been diagnosed as having excessive cholinergic nerve excitement of . (2) abrupt onset, productive poisoning generally contacting it for 2 ~ 4 h after the onset, is fast - a - half - hour while the oral poisoning was more rapid, more in 10 ~ 30 min (2) abrupt onset, productive poisoning generally contacting it for 2 ~ 4 h after the onset, is fast - a - half - hour while the oral poisoning was more rapid, more in 10 ~ 30 min .
symptoms (3) and rapid recovery, and the detachment after timely treatment, usually back to normal within a few hours ( symptoms (3) and rapid recovery, and the detachment after timely treatment, usually back to normal within a few hours (. 4) poisoning does not occur after delayed peripheral neuropathy ( 4) poisoning does not occur after delayed peripheral neuropathy (.
5) contaminated with topical ocular stinging, conjunctival congestion, 5) contaminated with topical ocular stinging, conjunctival congestion,. miosis, etc (6) of whole blood cholinesterase activity in urine ( miosis, etc (6) of whole blood cholinesterase activity in urine (.
7) 3 - hydroxy carbofuran determination can be used as contact indicators 7) 3 - hydroxy carbofuran determination can be used as contact indicators . principles (1) Leave the site quickly, thoroughly clean poison principles (1) Leave the site quickly, thoroughly clean poison .
polluters skin, Remove contaminated clothes, repeatedly washed with soap and polluters skin, Remove contaminated clothes, repeatedly washed with soap and . oral intoxication should quickly induce vomiting, lavage are repeatedly washed with water or gastric juice oral intoxication should quickly induce vomiting, lavage are repeatedly washed with water or gastric juice .
2% ~ 5% sodium bicarbonate solution (2) 2% ~ 5% sodium bicarbonate solution (2) . antidote atropine or scopolamine hydrobromide, usage and dosage in this section outline; Oxime antidote atropine or scopolamine hydrobromide, usage and dosage in this section outline; Oxime .
invalid in the case of a product with organophosphorus pesticide poisoning with mixed with atropine, according to the illness needs,In the poisoning after a period of time, at the discretion of the appropriate amount of Oxime invalid in the case of a product with organophosphorus pesticide poisoning with mixed with atropine, according to the illness needs,In the poisoning after a period of time, at the discretion of the appropriate amount of Oxime . (3) symptomatic and supportive therapy (3) symptomatic and supportive therapy .
preventive actions to strengthen education on safety production, attention is given to the production, handling and use of the process of standardizing operations, and strengthen personal protection shall be prohibited; cruel treatment causing injury even death of pesticide mixed with food or the like, to prevent accidental ingestion preventive actions to strengthen education on safety production, attention is given to the production, handling and use of the process of standardizing operations, and strengthen personal protection shall be prohibited; cruel treatment causing injury even death of pesticide mixed with food or the like, to prevent accidental ingestion .
