Name | CHLORDIMEFORM |
Synonyms | Ciba 8514 ciba-8514 Ciba-C8514 CHLORDIMEFORM Chlorfenamidine Chlorophenamidin Chlorphenamidine chlorodimeform(newzealand) |
CAS | 6164-98-3 |
EINECS | 228-200-5 |
Molecular Formula | C10H13ClN2 |
Molar Mass | 196.68 |
Density | 1.05 |
Melting Point | 35° |
Boling Point | 293℃ |
Flash Point | 131℃ |
Water Solubility | 0.27g/L(20 ºC) |
Appearance | neat |
Merck | 13,2100 |
BRN | 9256367 |
pKa | 7.89±0.50(Predicted) |
Storage Condition | 2-8°C |
Refractive Index | nD25 1.5885 |
Physical and Chemical Properties | Colorless crystals. Melting point 32 ℃, boiling point 163-165 ℃(1.86kPa), relative density 1.105(25/4 ℃), refractive index 1.5885(25 ℃). The vapor pressure at 20 ℃ is 0.047Pa. The solubility in water at 20 ℃ is 250ppm, and it is easily soluble in organic solvents. The commodity is its aqueous hydrochloride solution. Pure chlordimeform hydrochloride [19750-959-9], white crystal, melting point 225-227 ℃ (decomposition), relative density 1.110. Easily soluble in water, hardly soluble in organic solvents, stable in acidic solution, easy to precipitate crystals in neutral solution, and decompose in alkali. |
Risk Codes | R21/22 - Harmful in contact with skin and if swallowed. R40 - Limited evidence of a carcinogenic effect R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
Safety Description | S22 - Do not breathe dust. S36/37 - Wear suitable protective clothing and gloves. 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. |
UN IDs | 2761 |
WGK Germany | 1 |
RTECS | LQ4375000 |
HS Code | 29252100 |
Hazard Class | 6.1(b) |
Packing Group | III |
Toxicity | LD50 i.p. in rats: 238 mg/kg (Robinson, Smith) |
(IARC) carcinogen classification | 3 (Vol. 30, Sup 7) 1987 |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
overview | chlordimeform (Chlordimeform), an efficient, broad-spectrum, low-toxic organic nitrogen insecticide and acaricide. In 1966, the Federal German Schering Company (Schering AG) and Swiss Ciba AG developed. The pure product is colorless crystal, slightly soluble in water, and more soluble in benzene, chloroform and other solvents. Hydrolyzed in neutral and acidic solutions. Because it can generate salts in acidic media and is relatively stable, it is often made into the form of hydrochloride nowadays. The pure product is white crystal, which is more water-soluble and easy to decompose when encountering alkali. The dosage form is aqua. It has contact killing, stomach poison, anti-feeding and repellent effects, and has a certain egg killing effect. It can be used to control various pests and mites on rice, cotton and other crops. Due to the chronic toxicity of higher animals, it can only be used to control cotton red spider and rice stem borer. |
pharmacokinetics | chlordimeform can be absorbed through the digestive tract, respiratory tract and skin, and its distribution in the body is liver, kidney, lung, spleen, brain, Heart, pancreas, fat. Animal experiments have proved that chlordimeform and its metabolites (mainly p-chloro-toluidine) can be quickly excreted in urine. At 24 hours after administration, the urine output was 85% in rats, 70-80% in dogs and 65% in dairy sheep. Chlordimeform can also be excreted from the bile duct and milk. Because chlordimeform is rapidly metabolized and excreted in the body, there is no obvious accumulation in the tissue. However, in plants, chloro-o-toluidine, the main metabolite of chlordimeform, remains for a long time. Chlordimeform does not cause the inhibition of cholinesterase, nor does it cause cholinergic nerve excitement at the toxic dose, and does not produce the stimulation symptoms of cholinergic receptors in the skeletal muscle. It is generally believed that chlordimeform has a unique effect on the sympathetic nerve but has no effect on the parasympathetic nerve. |
toxicity | is a medium toxic category. Acute oral LD50 is 340~490 mg/kg in rats and 270~400 mg/kg in mice. The percutaneous LD50 of rats is 2600 mg/kg. Toxic effects appear rapidly. Acute poisoning symptoms are mainly nerve excitement, restlessness, convulsions, shortness of breath, and finally death due to respiratory failure. The lethal process is rapid, and the survivors recover quickly. In subacute tests, it can cause growth delay. In the chronic test, rats and dogs were fed for 2 years. When the dose was more than 500 ppm, there were obvious liver cell nodular hyperplasia, bile duct hyperplasia and mild hypertrophy of adrenal cortex cells. |
poisoning | human chlordimeform poisoning is mainly acute poisoning caused by accidental administration and productive poisoning accidents caused by carelessness in production and application. The symptoms of human poisoning are mainly drowsiness, fatigue and weakness, and its main metabolite, chloro-toluidine, can cause bladder irritation and hematuria. Long-term exposure to high concentrations of chlordimeform can damage the microcirculation of the skin. First aid is mainly symptomatic treatment, proper rehydration to facilitate the excretion of poison. When severe poisoning has cyanosis, a small dose of methylene blue can be injected intravenously. Pay close attention to the patient's renal function damage during treatment. Determination of chloro-toluidine in urine can be used as an indicator of the degree of absorption of the body. |
Carcinogenic | In the carcinogenic test, mice were fed for life, and it was found that chlordimeform and its metabolites, N-formyl 4-Chloro-toluidine and 4-Chloro-toluidine have carcinogenic effects, mainly causing malignant hemangioendothelioma of connective tissue. In the carcinogenic test of mouse skin applied for a long time, it was found that the skin of mice coated with chlordimeform was prolonged by croton oil, and the incidence of skin papilloma was significantly increased, and there was a significant dose-effect relationship in the test. There is a potential carcinogenic risk to the human body, and many countries have banned production and use. |
apply | to control cotton and rice pests. ① Control cotton spider mites, cotton bollworm, cotton red bollworm, etc. ② Control of rice stem borer, stem borer, and rice leaf roller. Only once during the entire rice growth period. The safety interval is 50 days. It is not allowed to be used on other crops such as grain, oil, vegetables, fruit trees, medicinal materials, tea, tobacco, sugar cane, sugar beet, etc. |
drug residue | the residue monitoring plan of the state administration of quality supervision and inspection stipulates that the maximum residue limit of chlordimeform in honey is 10 μg/kg. At present, there are many methods for detecting chlordimeform in food, including high performance liquid chromatography (HPLC), gas chromatography (GC), thin layer chromatography (TLC), gas chromatography/mass spectrometry (GC/MS), etc. |
References | [1] China Agricultural Encyclopedia Editor-in-Chief Committee Pesticide Volume Editorial Committee, China Agricultural Encyclopedia Editorial Department Editorial Department. Encyclopedia of Pesticides in China. Pesticide roll. Beijing. Agriculture Press. 1993. No. 335-336. [2] Edited by the Editorial Committee of China Medical Encyclopedia; Editor-in-Chief Gu Xueji. Chinese Medical Encyclopedia • Eight Toxicology. Shanghai. Shanghai Science and Technology Publishing House. 1982. Page 159. [3] He Ji, Lu Hengli, Cheng Yiren and other editors. Internal medicine diagnosis and treatment. Jinan: Shandong Science and Technology Press. 1996. Page 334. [4] Yi Xionghai, Han Li, Yang Huiqin, Fan Xiang, Zhu Jian, Guo Dehua. Determination of Chlordimeform and Its Metabolites Residues in Honey by Liquid Chromatography-Tandem Mass Spectrometry [J]. Chromatography, 2010,07:649-653. [5] Xie Jianjun, Chen Jie, He Manli, Yuan Zhenyu, sun Linghui. Determination of Chlordimeform and Its Metabolite Residues in Animal-derived Food by Gas Chromatography-Mass Spectrometry [J]. Journal of Analytical Testing, 2012,11:1358-1364. |
use | chlordimeform is the earliest developed formamidine insecticide and acaricide. It has good absorption effect and good insecticidal and acaricidal effects. It is mainly used to control rice stem borers, and can also be used to control cotton red spider, red bollworm, fruit tree red spider, scale insect, etc. Generally diluted to 300-500 times spray. About 50g of chlordimeform is used per mu of field. The toxicity of chlordimeform metabolites has been controversial, and their use should be strictly in accordance with the regulations of the agricultural sector. This product is highly toxic to silkworms and should be paid special attention when used in sericulture areas. It should not be mixed with alkaline pesticides. |
production method | chlordimeform has many synthetic routes:(1) phosgene method; Raw material consumption quota based on 100% chlordimeform: phosgene 790kg/t, dimethylformyl chloride 480kg/t, o-toluidine 640kg/t, chlorine 410kg/t. (2) phosphorus oxychloride method;(3) thionyl chloride method;(4) p-toluenesulfonyl chloride method, etc. |
category | pesticide |
toxicity classification | highly toxic |
acute toxicity | oral-rat LD50: 160 mg/kg; Oral-mouse LD50: 160 mg/kg |
stimulation data | eye-rabbit 100 mg severe |
flammability hazard characteristics | flammability; thermal decomposition of toxic chloride, nitrogen oxide gas |
storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from food raw materials storage and transportation |
fire extinguishing agent | sand, dry powder, foam |
occupational standard | TWA 0.5 mg/kg; STEL 1.5 mg/kg |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |