105268-95-9
carbendazim
CAS: 10605-21-7;102040-01-7;105268-95-9;110342-67-1;212384-28-6;276680-08-1;39413-19-9;59758-95-1;63090-4
Molecular Formula: C9H9N3O2
105268-95-9 - Names and Identifiers
105268-95-9 - Physico-chemical Properties
| Molecular Formula | C9H9N3O2 |
| Molar Mass | 191.19 |
| Density | 1.4500 |
| Melting Point | >300 °C (lit.) |
| Boling Point | 326.92°C (rough estimate) |
| Flash Point | 11°C |
| Solubility | Insoluble in water and general organic solvents, the solubility (mass ratio) at 20°C is: acetone 0 · 04%, ethanol 0 · 03%, chloroform 0 · 01%, benzene, ether and water are all less than 0 · 001%. Soluble in organic acids such as sulfuric acid, hydrochloric acid and acetic acid, and form corresponding salts. It is more stable to heat and acid |
| Vapor Presure | 1.5 x 10-4 Pa (25 °C) |
| Appearance | The pure product is white crystal, and the industrial product is light yellowish brown powder. |
| Merck | 13,1799 |
| BRN | 649044 |
| pKa | 4.48(at 25℃) |
| Storage Condition | -20°C |
| Refractive Index | 1.6500 (estimate) |
| MDL | MFCD00055390 |
| Physical and Chemical Properties | White crystalline powder. Sublimation began at 216-217 ℃. Melting point 307~312 °c (decomposition). Density 1.45±0.05g/cm3(20 degrees C), vapor pressure 1.3.33 Pa(20 degrees C). Solubility (24 ℃): Water 29(pH 4), 8(pH 7), 7(pH 8)mg/L, hexane 0.5mg/L, benzene 36mg/L, ethanol, acetone 300mg/L, dichloromethane 68mg/L, ethyl acetate 135mg/L. Stable to heat. |
| Use | Can control peanut leaf spot, black spot, Triticum aestivum scab, Sclerotinia sclerotiorum, rice sheath blight, citrus canker and so on. |
105268-95-9 - Risk and Safety
| Risk Codes | R46 - May cause heritable genetic damage R60 - May impair fertility R61 - May cause harm to the unborn child R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S36/37 - Wear suitable protective clothing and gloves. S16 - Keep away from sources of ignition. |
| UN IDs | UN 3077 9/PG 3 |
| WGK Germany | 3 |
| RTECS | DD6500000 |
| HS Code | 29339900 |
| Toxicity | LD50 oral in rabbit: 8160mg/kg |
105268-95-9 - Upstream Downstream Industry
| Downstream Products | Benomyl |
105268-95-9 - Reference
| Reference Show more | 1. Xiao Suping, Zhong Rongrong, Gao Hui, et al. Rapid Determination of Eight Pesticide Residues in Different Dendrobium by Ultra Performance Liquid Chromatography-Tandem Mass Spectrometry [J]. Modern Chinese Medicine, 2020, v.22(04):135-140 153. 2. Liu, Shaoying, et al. "Comparison of extraction solvents and sorbents in the quick, easy, cheap, effective, rugged, and safe method for the determination of pesticide multiresidue in ruits by ultra high performance liquid chromatography with tandem mass s 3. [IF = 3.969] Xu Shiqiang et al." Molecular characterization of carbendazim resistance of Fusarium species complex that problems sugarcane pokkah boeng disease."Bmc Genomics. 2019 Dec;20(1):1-14 |
105268-95-9 - Nature
Open Data Verified Data
The Pure product is white crystal, and the industrial product is yellowish brown powder. mp302 ~ 307 C (decomposition);pK. 4.48. Solubility in solvent at 20 ° C. (mg/L): n-hexane 0.5, benzene 36, ethanol 300, chloroform 100, acetone 300. Relatively stable to heat, unstable to acid-base.
Last Update：2024-01-02 23:10:35
105268-95-9 - Preparation Method
Open Data Verified Data
methyl chloroformate is synthesized from phosgene and methanol by batch and continuous processes, and then methyl cyanocarbamate is obtained by cyanoammoniation with methyl chloroformate after hydrolysis of ammonia to form cyanamide. Finally, the reaction of O-phenylenediamine with methyl cyanocarbamate yields carbendazim.
Last Update：2022-01-01 10:12:21
105268-95-9 - Introduction
Insoluble in water and general organic solvents, the solubility (mass ratio) at 20 ℃ is: acetone 0.04%, ethanol 0.03%, chloroform 0.01%, benzene, ether and water are all less than 0.001%. Soluble in organic acids such as sulfuric acid, hydrochloric acid and acetic acid, and form corresponding salts. It is stable to heat and unstable to acid and alkali.
Last Update：2022-10-16 17:11:48
105268-95-9 - Use
Open Data Verified Data
carbendazim is a benzimidazole fungicide. High efficiency, low toxicity, broad bactericidal spectrum, long duration, for many ascomycetes, semilynoides and a variety of Basidiomycetes effective, invalid for algae. Carbendazim can be absorbed by plants and transferred to other parts through conduction, which interferes with the mitosis of pathogenic cells and inhibits their growth. For the prevention and control of Triticum aestivum scab, cereal smut, cotton seedling disease, Sclerotinia sclerotiorum, rice sheath blight, rice blast, beet brown spot disease. For the prevention and control of grain, cotton, oil, fruit, vegetables, flowers, a variety of fungal diseases, can also be used for fruit preservation. Generally processed into powders, wettable powders and suspensions are used.
Last Update：2022-01-01 10:12:21
105268-95-9 - Safety
Open Data Verified Data
rats, mice by mouth> 5000~15000mg/kg, rat percutaneous LD50>2000mg/kg, rat intraperitoneal injection LD50> 15000mg/kg. The original drug on dogs and rats for three months of feeding, no effect of doses were 500 mg/kg and 400 mg/kg, no carcinogenic, teratogenic and mutagenic effects. Low toxicity to fish and bees, carp LC50 40mg/L(48h).
Last Update：2022-01-01 10:12:22
105268-95-9 - Reference Information
| LogP | 1.4-1.5 at 25℃ and pH5-9 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| systemic broad-spectrum fungicide | carbendazim, also known as cotton weiling, kabundan, mildew spot, benzimidazole 44, is a kind of high-efficiency and low-toxicity systemic broad-spectrum fungicide, belonging to benzimidazole compounds, stable chemical properties, systemic treatment and protection. Low toxicity to humans and animals, rats oral acute LD50>2000 mg/kg, toxicity to fish is also low. It has a preventive effect on many diseases of Ascomycetes, Basidiomycetes and Seminergic. Seed treatment, foliar spraying and soil treatment can prevent and control a variety of diseases of rice, cotton, vegetables, fruit trees and wheat, such as wheat smut, head blight, apple ring rot, fruit tree scab, sweet potato black spot, Wheat smut, anthracnose, grape brown spot, anthracnose, gray mold, rape sclerotinia, cotton seedling diseases, vegetable gray mold, vegetable powdery mildew, blight, sclerotinia, gray mold, etc. When preventing and controlling wheat head blight, stripe rust and powdery mildew, it can be mixed with triadiumine for better effect. However, it is ineffective or only weakly virulent for diseases caused by oomycetes in fungi, ascomycetes and cyclospora such as Alternaria and plant pathogenic bacteria. It has little ability to inhibit the germination of fungal spores, mainly to prevent the growth of hyphae. The effect on thallus cells is similar to colchicine, which can combine with the tubulin subunits in the nucleus to form a complex, thereby hindering the normal formation of spindle filaments and inhibiting cell mitosis. It is safe for plants at the dosage, and the safe interval before harvest is 25 days (14 days for strawberries). Allowable residue (mg/kg) grain 0.5, cucumber 0.5, grape 3.0, banana (meat) 0.2, citrus (peeled) 1.0. |
| mode of action | carbendazim belongs to benzimidazole and is a high-efficiency and low-toxicity systemic fungicide. due to its obvious top-to-top transport performance, it is also used for seed dressing and soil pouring besides leaf spraying. It has protective and therapeutic effects, and has a wide spectrum of disease prevention. It has a good effect on Botrytis, Fusarium, Cercospora, Penicillium, Ceratocystis, Sclerotinus, Sclerotinus, Sclerotinus, and Sclerotinus; but it is not effective against algines and bacteria; there are also obvious choices for the effect of Ascomycetes, that is, it is not sensitive to the genus Odonospora and Cycloospore. Its main mechanism of action is to interfere with the formation of spinning bodies during mitosis of bacteria, thus affecting the cell division process of bacteria. carbendazim is a broad-spectrum systemic fungicide. The agent is absorbed by seeds, roots, and leaves, and can be conducted in the crop body. It has protective and therapeutic effects and has a long residual effect. It has activity against many pathogenic bacteria in Ascomycetes, Basidiomycetes and Seminergic, but has no activity against Oomycetes, Alternaria, Helminthospora and bacteria. The agent has little inhibitory effect on the germination of pathogen spores, but has a strong inhibitory effect on the growth of mycelium. The antibacterial mechanism is to inhibit hyphal cell division, hinder the formation of spindle during mitosis, and interfere with the formation of nucleic acid. |
| quality standard | 40% carbendazim suspending agent consists of active ingredients, additives and water. The appearance is light brown viscous flowable suspension, the density is 1.1~1.3, the pH value is 5~8, the average particle size is 3~5 μm, the suspension rate is determined in standard hard water (342mg/L) ≥ 90%, stored at room temperature for two years, the content of effective components is basically unchanged. 25%. 50% carbendazim wettable powder consists of active ingredients, wetting agents and carriers. The appearance is light brown loose powder, pH value is 5~9, moisture content ≤ 3.5%, suspension rate ≥ 40%, and the content of effective components stored at normal temperature for two years is basically unchanged. |
| control object | carbendazim is effective against peanut-based rot, sugar beet brown spot, apple brown spot, pear scab, peach scab, grape white rot, anthracnose, etc. In addition, it can also be used for mildew prevention of industrial products such as textiles, paper, leather, rubber, etc. carbendazim cream has a significant effect on tinea manus and onychomycosis. |
| toxicity | acute oral LD50>5000~15000mg/kg in rats and mice, acute percutaneous LD50>2000mg/kg in rats and intraperitoneal LD50>15000mg/kg in rats. Rats can tolerate in the space containing 2.2mg/L active components. The original drug was fed to dogs and rats for 3 months with no effect doses of 500mg/kg and 400mg/kg respectively. No carcinogenic, teratogenic and mutagenic effects were found. Low toxicity to fish and bees. Carp LC50 was 40mg/L (48h). |
| precautions | (1) carbendazim can be mixed with general fungicides, but it should be mixed with pesticides and acaricides, and cannot be mixed with copper preparations. The diluted liquid medicine will be stratified after not standing for the time being, and it needs to be shaken well. (2) The dispensing and application personnel should pay attention to prevent contamination of hands, face and skin. If there is contamination, they should be cleaned in time. Do not smoke, drink water or eat during operation. After the work is completed, clean the hand face and exposed parts that may be contaminated in time. Carbendazim can cause poisoning through the esophagus, etc., and treatment can be taken or injected with atropine. (3) Attention should be paid to cleaning various tools after application. Packaging materials should be recycled in time and properly disposed. (4) The medicine should be sealed and stored in a cool and dry place. Special vehicles and warehouses shall be provided for transportation and storage. It shall not be transported and stored with food and daily necessities. (5) Use should abide by the usual pesticide use protection rules, do a good job of personal protection. (6) The agent is a single-action fungicide, and pathogenic fungi are easily resistant to it. Such as gray mold, bad seedling bacteria, black star disease bacteria, asparagus stem blight bacteria, cacospora and sclerotinia have all developed drug resistance in the field. In order to delay the development of drug resistance, it should be used alternately with other fungicides to avoid continuous single use. (7) The safe interval period is 30 days for rice and 20 days for wheat. |
| use | carbendazim is a high-efficiency, low-toxicity, broad-spectrum, systemic fungicide, with a long duration, and is effective against many ascomycetes, Seminotic bacteria and various basidiomycetes, but ineffective against algae. Used to prevent and control wheat head blight, rice sheath blight, rice blast, sclerotinia sclerotiorum, many fruit trees and vegetable diseases, such as powdery mildew, anthracnose, scab, etc., with 50% wettable powder 750~1000 times liquid spray. Seedling treatment can prevent and control grain crop smut, melon, tomato wilt, etc. In addition, it can also be used for anti-mold in papermaking, textile, leather, rubber and other industries. Carbendazim is a benzimidazole fungicide. It was originally an intermediate of the fungicide benomyl. It was developed by DuPont in the United States in 1967. Later, scientific and technological workers in the United States and China independently discovered the bactericidal properties of carbendazim. In the mid-70s, China and Germany successively realized industrial production, and now they have become the largest variety of systemic fungicides in my country. It is used to prevent and control Sanmai scab, cereal smut, cotton seedling disease, rape sclerotinia, rice sheath blight, rice blast, sugar beet brown spot, etc. Carbendazim can be absorbed by plants and transferred to other parts through conduction, interfering with the mitosis of germ cells and inhibiting its growth. It has a wide bactericidal spectrum, and is usually processed into powders, wettable powders and suspending agents for seed treatment or foliar spraying to prevent and control various fungal diseases of grains, cotton, oil, fruits, vegetables, and flowers. It can also be used for fruit preservation. Carbendazim has also been reported as an industrial fungicide. |
| production method | there are many ways to synthesize carbendazim. in our country, calcium cyanamide is used, I .e. calcium cyanamide hydrogen is prepared from calcium cyanamide (lime nitrogen) and water, and calcium hydroxide and residue produced are filtered and separated (calcium hydroxide can also be used as deacidizing agent in the following process without filtering first, and then filtered after synthesizing methyl cyanamide formate, this is called the post-filtration method; the residue separated by this method contains toxic organic impurities), and then the cyanamide calcium hydrogen solution and methyl chloroformate are stored in sodium hydroxide to form a cyanamide methyl formate solution, and then Condensation with o-phenylenediamine to obtain carbendazim. preparation of methyl chloroformate phosgene and methanol synthesis of methyl chloroformate, there are batch method and continuous method. The tower continuous ester method has the advantages of good quality, high yield, low consumption quota and large production capacity. The temperature is 20~30 ℃, the ratio is 1:1.1, phosgene is excessive: the residence time of reactants in the tower is reflected in the feeding speed, and the feeding speed of methanol in the small test is in the range of 2.4~4mol/(h l), which has little effect on the reaction. The preparation of methyl cyanocarbamate is prepared by hydrolysis of lime nitrogen to generate cyanamide and then cyanamide with methyl chloroformate. The reaction temperature of cyanamide is 45 ℃, and the temperature is kept for 1h after dropping methyl chloroformate. The ratio of methyl chloroformate to lime nitrogen is 2.0:1.5. Synthesis of carbendazim o-phenylenediamine reacts with methyl cyanocarbamate to produce carbendazim. The presence of hydrochloric acid is very necessary for the reaction, and the reaction temperature is controlled at 90~95 ℃. |
| category | pesticide |
| toxicity classification | low toxicity |
| acute toxicity | oral-rat LD50: 6400 mg/kg; Oral-mouse LD50: 7700 mg/kg |
| flammability hazard characteristics | combustion produces toxic nitrogen oxide gas |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from food raw materials storage and transportation |
| fire extinguishing agent | dry powder, foam, sand |
| occupational standard | STEL 0.1 mg/m3 |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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CAS: 10605-21-7
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