Tiadinil

Structural formula
General
Surname	Tiadinil
other names	5- (3-chloro-4-methylanilinocarbonyl) -4-methyl-1,2,3-thiadiazole; N - (3-chloro-4-methylphenyl) -4-methyl-1,2,3-thiadiazole-5-carboxamide;
Molecular formula	C 11 H 10 ClN 3 OS
Brief description	light yellow solid
External identifiers / databases
EC number	606-997-4
ECHA InfoCard	100.118.348
PubChem	2804318
ChemSpider	2082871
Wikidata	Q19310041
properties
Molar mass	267.73 g mol −1
Physical state	firmly
Melting point	112.2 ° C
solubility	sparingly soluble in water (13.2 mg l −1 at 20 ° C); soluble in methanol (124 g l −1 ), acetone (434 g l −1 ), toluene (11.8 g l −1 );
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 332
	P: no P-phrases
Toxicological data	6147 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 mg kg −1 ( LD 50 , rat , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tiadinil is a chemical compound from the group of thiadiazolecarboxamides .

Extraction and presentation

Tiadinil can be obtained through a multi-step reaction starting from a beta-ketoester. This is converted with an N -acetylated hydrazine to a hydrazone, which is cyclized with thionyl chloride and then hydrolyzed. After further conversion to the acid chloride , tiadinil is formed by reaction with 3-chloro-4-methylaniline .

properties

Tiadinil is a light yellow solid that is sparingly soluble in water.

use

Tiadinil is used as a fungicide (e.g. against Magnaporthe grisea in rice). The compound was introduced by Nihon Nohyaku in 1995 and approved in Japan in 2003. It is mostly used in conjunction with insecticides .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j data sheet Tiadinil at Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).
^ ^A ^b Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 918 ( limited preview in Google Book search).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j data sheet Tiadinil at Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).

[Ulrich_Schirmer,_Peter_Jeschke,_Matthias_Witschel-2] A ^b Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 918 ( limited preview in Google Book search).