In 2021, thiortraniliprole (tiorantraniliprole) is a bisamide insecticide independently developed by Qingdao University of Science and Technology in 2013, and in 2021, 95% of thiortraniliprole and 10% thiantraniliprole suspension were first registered in China. Bisamide insecticides are relatively environmentally friendly compounds, and thipropaniliprole is another domestic light after tetrachlorantraniliprole, cycloprofluluramid, cyhalotraniliprole and fluchlorantramide, which is an important supplement to this type of insecticide in the control of lepidopteran pests.
Product Introduction
英文名称:tiorantraniliprole
Chinese name: thiocarnamide
Chemical Name: 5-Bromo-2-(3-chloropyridin-2-yl)-N-[2,4-dichloro-6-(propyl-2-aminomethionyl)phenyl]pyrazole-3-carboxamide
分子式：C19H15BrCl3N5OS
Relative molecular mass: 544.924622
CAS accession number: 1442448-92-1
Structural formula:
Three-dimensional structural formula:
Physical and chemical properties: the mass fraction of thipropaniliprole is 95%, and the appearance is off-white powder; Range: 217.4~219.2°C; Solubility: Solubility in water, g/L: 1.10 x10-4 (pH 6.5); Solubility in organic solvents, g/L: 1,2-dichloroethane: 10~14, methanol: 20~25, acetone: 100~114, ethyl acetate: 40~50, solubility in n-n-heptane, g/L: 1.09 x10-3; Solubility in p-xylene, g/L: 1.89. 10% thipropaniliprole suspension, pH 5~8; The suspension rate ≥ 90%. The cold and hot storage of the product and the storage at room temperature for 2 years are stable.
Mechanism of action
Thiocarniliprole belongs to the fish nitine receptor inhibitor class of insecticides, which leads to the unrestricted release of calcium ions in the intracellular calcium pool by activating the fish nitin receptor in insect muscle cells, making the insect muscle relaxant paralysis, paralysis, stop feeding, and eventually death. It has gastric toxicity and root systemic activity, and from a structural point of view, the introduction of sulfur makes it have better systemic conductivity than chlorantraniliprole.
apply
Application: rice, corn, cabbage, cabbage, tomato, ginger, peach, pear, sugarcane, sunflower, cucumber, pepper, citrus, apple, tea tree, cowpea, peanut and other crops. Target pests: rice leaf roller, dimorphic borer, diamondback moth, cabbage worm, Spodoptera litura, Spodoptera exigua, armyworm, cotton bollworm, corn borer and American white moth, etc., at the same time, it also has a good control effect on homoptera pests and underground pests.
Common dosage form: 10% thiobraniliprole SC
Synthetic routes
Indigo anhydride initiates a reaction with methylamine to form 2-amino-N-methylbenzamide; 2-amino-N-methylbenzamide reacts with sulfonyl chloride to form 2-amino-3,5-dichloro-N-methylbenzamide; 2-amino-3,5-dichloro-N-methylbenzamide was added in batches in P2S5 to form 2-amino-3,5-dichloro-N-methylthiobenzamide, and then 2-amino-3,5-dichloro-N-methylthiobenzamide was amidated and condensed with K acid to obtain the target compound thioantraniliprole, and the synthesis route was as follows:
summary
Although food security, environmental safety and other issues continue to be mentioned, the degree of attention continues to increase, but the continent to eliminate highly toxic pesticides, harmful pesticides and backward production capacity speed due to the wide range of slow progress, the current economic situation, the development of new compounds is not in line with the fundamental interests of enterprises, and with the expiration of the big brother chlorantraniliprole patent, the rapid expansion of production capacity, the synthesis cost in the scale advantage continues to decrease, the end cost continues to explore, from the synthesis route, thiobraniliprole and chlorantraniliprole share part of the intermediate, In the future, the cost is expected to be further reduced, and the cost performance is also a powerful tool to replace highly toxic pesticides.
In addition to the existing chlorantraniliprole market, through the understanding of thiobraniliprole characteristics, thipropaniliprole in the compound and underground granule market and seed treatment agents should continue to explore, maybe there are better opportunities.