Probenazole

Structural formula
General
Surname	Probenazole
other names	3- (2-propenyloxy) -1,2-benzisothiazole-1,1-dioxide; 3-allyloxy-1,2-benzisothiazole-1,1-dioxide; Oryzemate;
Molecular formula	C 10 H 9 NO 3 S
Brief description	colorless solid
External identifiers / databases
EC number	608-113-2
ECHA InfoCard	100.120.783
PubChem	91587
Wikidata	Q11336142
properties
Molar mass	223.25 g mol −1
Physical state	firmly
Melting point	138-139 ° C
solubility	poorly soluble in water (0.15 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	2030 mg kg −1 ( LD 50 , rat , oral ) ; 2750–3000 mg kg −1 ( LD 50 , mouse , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Probenazole is a chemical compound from the group of benzoisothiazoles and a derivative of saccharine .

Extraction and presentation

Probenazole can be obtained by reacting 3-chloro-1,2-benzisothiazole-1,1-dioxide with allyl alcohol .

properties

Probeazole is a colorless solid that is sparingly soluble in water. It is not poisonous to fish. The degradation in the soil takes place very quickly. The half-life is less than a day.

use

Probenazole was introduced in 1975 by Meiji Seika Kaisha and Hokko Chemical Industry (Japan) as a systemic fungicide . It was the first fungicide to be effective by activating the plant's own resistance mechanisms. The acquired resistance is mediated by the accumulation of salicylic acid .

Probenazole has an excellent effect against the rice blast fungus and rice leaf blight . Today it is widely used in conjunction with insecticides.

Admission

In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet probenazol from Sigma-Aldrich , accessed on May 22, 2017 ( PDF ).
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 426 ( limited preview in Google Book search).
↑ Entry on probenazole. In: Römpp Online . Georg Thieme Verlag, accessed on January 2, 2015.
↑ ^a ^b Hiroki Ota: Historical Development of Pesticides in Japan, pp. 81-83
↑ Keiko Yoshioka, Hideo Nakashita, Daniel F. Klessig, Isamu Yamaguchi: Probenazole induces systemic acquired resistance in Arabidopsis with a novel type of action . In: The Plant Journal . tape 25 , no. 2 , January 2001, p. 149–157 , doi : 10.1111 / j.1365-313x.2001.00952.x ( PDF ).
↑ Hideo Nakashita, Keiko Yoshioka, Michiko Yasuda, Takako Nitta, Yuko Arai, Shigeo Yoshida, Isamu Yamaguchi: Probenazole induces systemic acquired resistance in tobacco through salicylic acid accumulation . In: Physiological and Molecular Plant Pathology . tape 61 , no. 4 , October 2002, p. 197-203 , doi : 10.1006 / pmpp.2002.0426 ( PDF ).
↑ Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 913 ( limited preview in Google Book search).
^ Directorate-General for Health and Food Safety of the European Commission: Entry on probenazole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 14, 2016.

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet probenazol from Sigma-Aldrich , accessed on May 22, 2017 ( PDF ).

[unger-2] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 426 ( limited preview in Google Book search).

[RömppOnline-3] Entry on probenazole. In: Römpp Online . Georg Thieme Verlag, accessed on January 2, 2015.

[ohta-4] Hiroki Ota: Historical Development of Pesticides in Japan, pp. 81-83

[sar-5] Keiko Yoshioka, Hideo Nakashita, Daniel F. Klessig, Isamu Yamaguchi: Probenazole induces systemic acquired resistance in Arabidopsis with a novel type of action . In: The Plant Journal . tape 25 , no. 2 , January 2001, p. 149–157 , doi : 10.1111 / j.1365-313x.2001.00952.x ( PDF ).

[saa-6] Hideo Nakashita, Keiko Yoshioka, Michiko Yasuda, Takako Nitta, Yuko Arai, Shigeo Yoshida, Isamu Yamaguchi: Probenazole induces systemic acquired resistance in tobacco through salicylic acid accumulation . In: Physiological and Molecular Plant Pathology . tape 61 , no. 4 , October 2002, p. 197-203 , doi : 10.1006 / pmpp.2002.0426 ( PDF ).

[moderncropprotection-7] Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 913 ( limited preview in Google Book search).

[PSM-8] Directorate-General for Health and Food Safety of the European Commission: Entry on probenazole in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 14, 2016.