{(2E)-3-[(6-chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene}cyanamide
Thiacloprid
CAS: 111988-49-9;111388-49-9
Molecular Formula: C10H9ClN4S
{(2E)-3-[(6-chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene}cyanamide - Names and Identifiers
{(2E)-3-[(6-chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene}cyanamide - Physico-chemical Properties
| Molecular Formula | C10H9ClN4S |
| Molar Mass | 252.72 |
| Density | 1.42±0.1 g/cm3(Predicted) |
| Melting Point | 128-129° |
| Boling Point | 423.1±55.0 °C(Predicted) |
| Flash Point | 209.665°C |
| Vapor Presure | 0-0Pa at 20-25℃ |
| Appearance | Pale yellow crystalline powder |
| pKa | 0.01±0.10(Predicted) |
| Storage Condition | -20°C |
| Refractive Index | 1.691 |
| MDL | MFCD02101042 |
| Physical and Chemical Properties | Yellowish powder, melting point 128~129 ℃, vapor pressure 3 × 10-10Pa (20 ℃), solubility in water at 20 ℃ is 185mg/L. The half-life in soil was 1-3 weeks. |
| Use | Broad-spectrum, systemic insecticides. Mainly used for rice, fruits, vegetables, cotton control most pests. |
{(2E)-3-[(6-chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene}cyanamide - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R20/22 - Harmful by inhalation and if swallowed. R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | 60 - This material and its container must be disposed of as hazardous waste. |
| UN IDs | 2588 |
| WGK Germany | 2 |
| RTECS | GS6093749 |
| HS Code | 29349990 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 in male, female rats (mg/kg): 836, 444 orally; >2000, >2000 dermally; LC50 (4 hr) in male, female rats (mg/m3): >2535, 1223; LC50 (96 hr) in rainbow trout (mg/l): 30.5 (Elbert) |
{(2E)-3-[(6-chloropyridin-3-yl)methyl]-1,3-thiazolidin-2-ylidene}cyanamide - Reference Information
| LogP | 1.3-1.4 at 24℃ and pH4-9 |
| surface tension | 72mN/m at 150mg/L and 20 ℃ |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| safety | 1, safe for humans and animals: thiacloprid has high insecticidal activity against Monochamus pine, but its toxicity is extremely low, and it is very high for humans and animals. The safety, and the medicine has no odor or irritation, and is safe for pesticide operators and residents in the pesticide application area. 2. Environmental safety: due to the low steam pressure of its active ingredients, it will not pollute the air. Due to the short half-life, thiacloprid residues will quickly decompose after entering the soil and water, which has little impact on the environment. 3. Safety of aquatic organisms: The toxicity to fish and other aquatic organisms is also very low, and usually there is basically no impact on aquatic organisms. 4. Safety for beneficial insects: Thiacloprid has very little effect on beneficial insects, especially for bees, and can also be used during flowering of trees and crops. 5. Microcapsule sustained-release technology greatly prolongs the duration of the drug. When used under rainy conditions, it can be controlled for about 40 days; when used under less rainy conditions, it can be effective for up to 90 days. This greatly reduces the number of applications and the amount of drugs used, so that pests at different insect stages can be controlled, and the cost of control is greatly reduced. |
| mechanism of action | thiacloprid was developed by Bayer Agrochemical Company of Germany and Bayer Agrochemical Company of Japan in the 1990 s. It has special effects on pricking and chewing mouthparts pests. Mechanism of action: Different from other traditional insecticides, it mainly acts on the posterior membrane of insect nerves. By binding to nicotinic acetylcholine receptors, it interferes with the normal conduction of the insect nervous system, causes the blockage of nerve channels, and causes a large amount of acetylcholine Accumulation, which makes insects abnormally excited , spasm and paralysis all over the body and death. It has strong contact killing, gastric toxicity and systemic effects. We know that organophosphorus and carbamate act on the acetylcholinesterase of insects, and pyrethroids act on nerve axons and affect The sodium ion channel in insect nerve cells, due to the different site and mechanism of action, thiacloprid has no interactive resistance with conventional insecticides, so it can be used for resistance control, it is widely used in the control of agricultural and forestry pests that have developed resistance to organophosphorus, carbamic acid esters and pyrethroids. It is one of the highly effective agents for the prevention and control of pricking and chewing mouthparts pests. |
| application | thiacloprid has excellent control effect on important pests on pear fruits, cotton, vegetables and potatoes. in addition to being effective on aphids and whiteflies, it is also effective on various beetles (such as potato beetles, apple flower weevil, rice weevil) and lepidopteran pests such as leaf miner and apple moth on apple trees, and it is applicable to all corresponding crops. For longicorn beetles, poplar beetles and many other longicettes that are difficult to control by general pesticides, it has a rapid killing effect, can effectively cut off the main transmission vector of pine wood nematode, and inhibit the occurrence of pine wood nematode disease. After 2 hours of application, a large number of cattle began to die, and the control effect after 24 hours can reach more than 90%. While preventing and controlling longicorn beetles, it can also play a role in controlling pine caterpillars, poplar boat moths, pine mealybugs, white moths and various inchworms that cross the insect stage. Japan was once the most harmful country for pine wood nematode disease. In recent years, Japan has promoted the use of thiacloprid to prevent and control longicorn pine. The control effect is very ideal, so that pine wood nematode disease has been effectively controlled in Japan, and the pine tree wilt loss rate has dropped to one in ten thousand. |
| features | as a new type of biopesticide, thiacloprid has the characteristics of high efficiency, low toxicity, safety and environmental protection, and little impact on the environment, trees and fruits. |
| toxicity | acute oral LD50 in male rats is 836 mg/kg, 444 mg/kg in female rats; Acute inhalation of LD502535mg/ m3 in male rats and 1223mg/ m3 in female rats; No irritation to rabbit eyes and skin, no sensitization to guinea pig skin. No carcinogenic and mutagenic effects on rat tests. Acute oral LD502716mg of quail/kg, rainbow trout LC5030.5 mg/L (96h), and EC50 of Daphnia were 5.3 μg/fish and 24.2 μg/fish respectively. |
| use | broad-spectrum, systemic neonicotinoid insecticides have good killing effect on pricking mouth device pests. Acting on nicotinic acid acetylcholine receptor, it has no cross resistance with organophosphorus, carbamate, pyrethroid conventional insecticides, and can be used for resistance management. The chemicals have excellent control effects on important pests on cotton, vegetables, potatoes and pear fruits. In addition to being effective for aphids and whiteflies, it is also effective for various beetles (such as potato beetles, apple weevil, rice weevil) and lepidopteran pests (such as apple tree leaf miner and apple moth), and it is also effective for corresponding crops. According to different crops, pests and usage methods, the recommended dosage is 48~180g active ingredient/hm2 for foliar spraying, and 20~60g active ingredient/hm2. |
| production method | 2.0g N-(2-chloro-5-pyridylmethyl) cysteamine and 1.3g cyanodithiamine dimethyl carbonate were added to 50mL of ethanol, and the mixture was refluxed under stirring for 8h under the protection of nitrogen. After the reaction is over, about 2/3 ethanol is removed by vacuum distillation, standing at room temperature, the product is crystallized and precipitated, filtered, washed with ether and then dried to obtain 2.4g of the target product, m.p.128~129 ℃. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:05:09
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