Chemical Properties
Isothiobacillin pure product is white powder. Melting point 193.7~195.1℃, vapor pressure 2.36×10-4mPa(25℃, calculated) Kow lgP=2.96(25℃), relative density 1.11. Solubility in water 0.5mg/L(20℃); solubility in other organic solvents(20℃, g/L): n-hexane 0.0594, toluene 6.87, methylene chloride 16.6, acetone 4.96, methanol 0.775, ethyl acetate 3.62. pKa -8.92(20℃-1℃). 4.96, methanol 0.775, ethyl acetate 3.62. pKa -8.92 (20 ℃ s 1 ℃)
Uses
Isotianil is a plant defense inducer that has no direct antimicrobial effect but instead activates typical plant defense responses. Isotianil can be used as a plant protection agent for controlling rice blast[1].
Definition
ChEBI: A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 3,4-dichloro-1,2-thiazole-5-carboxylic acid with o-cyanoaniline. It is a fungicide used for the control of rice blast.
Production Methods
Isotianil is commercially synthesised through the condensation of 3,4-dichloro-1,2-thiazole-5-carboxylic acid with o-cyanoaniline, forming a carboxamide linkage that defines its structure. This process involves standard organic synthesis techniques such as chlorination, amide formation, and purification steps like recrystallisation or chromatography to achieve high purity suitable for agricultural use.
Mechanism of action
Systemic Activated Resistance (SAR). Induces host plant defence.
References
[1] Ogawa M, Kadowaki A, Yamada T, et al. Applied development of a novel fungicide isotianil (STOUT)[J]. Sumitomo Kagaku, 2011, 1: 1-15.
[2] Katharina Portz, et al. Wheat blast caused by?Magnaporthe oryzae?pathovar?Triticum?is efficiently controlled by the plant defence inducer isotianil.?Journal of Plant Diseases and Protection?volume?128,?pages249-259 (2021).
