Buprofezin

Structural formula
	( Z ) isomer
General
Surname	Buprofezin
other names	( Z ) -2- tert -Butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazinan-4-one; ( Z ) -2 - [(1,1-Dimethylethyl) imino] tetrahydro-3- (1-methylethyl) -5-phenyl-4 H -1,3,5-thiadiazine-4-on;
Molecular formula	C 16 H 23 N 3 OS
Brief description	colorless solid
External identifiers / databases
EC number	614-948-3
ECHA InfoCard	100.125.182
PubChem	50367
Wikidata	Q2912604
properties
Molar mass	305.44 g mol −1
Physical state	firmly
density	1.1836 g cm −3
Melting point	104.6-105.6 ° C
solubility	practically insoluble in water; soluble in toluene, dichloromethane, acetone and ethyl acetate;
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	2198 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , mouse / rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Buprofezin is a chemical compound from the group of thiadiazinans . The name "Buprofezin" was originally used for a mixture of ( E ) and ( Z ) isomers , but in 2008 the sponsor discovered that the substance only contains the ( Z ) isomer and requested that the definition be changed.

Extraction and presentation

Buprofezin can be prepared by cyclocondensation of N -phenyl- N ' - tert -butylthioharnstoff with N -Methylenchlorid- N -carbonyl chloride-2-propylamine are obtained.

properties

Buprofezin is a colorless and odorless solid. It is stable to hydrolysis (at a pH value between 5 and 7) and photolysis.

use

Buprofezin is used as an insecticide and acaricide for many plants (such as tomatoes and citrus fruits). The effect is based on the inhibition of the chitin synthesis. Buprofezin is used, for example, against mealybugs, cicadas and whitefly . The compound was developed in 1981 by Nihon Nohyaku and approved for the first time in 1984. It was approved in Germany between 1996 and 2009.

In Germany and Austria none are permitted , in Switzerland pesticides (e.g. Applaud ) with this active substance are permitted.

safety instructions

Buprofezin is very toxic to aquatic organisms, but not very dangerous to mammals.

Individual evidence

↑ ^a ^b ^c Entry on buprofezin in the Hazardous Substances Data Bank , accessed November 2, 2015.

↑ ^a ^b ^c ^d ^e Buprofezin data sheet at Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).

↑ ^a ^b ^c ^d ^e FAO: Buprofezin .

↑ alan wood: buprofezin

^ Food and Agriculture Organization of the United Nations: Pesticide Residues in Food, 1991 Evaluations, 1991. Residues . Food & Agriculture Org., 1992, ISBN 978-92-5103196-4 , pp. 175 ( limited preview in Google Book search).

↑ Entry on buprofezin in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on November 12, 2015.

^ Peter Brandt: Reports on Plant Protection Products 2009 Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer-Verlag, 2010, ISBN 978-3-0348-0029-7 , pp. 10 ( limited preview in Google Book search).

↑ General Directorate Health and Food Safety of the European Commission: Entry on buprofezin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland and Germany ; accessed on February 14, 2016.

↑ Conclusion on the peer review of the pesticide risk assessment of the active substance buprofezin . In: EFSA Journal . tape 8 , no. 6 , June 2010, doi : 10.2903 / j.efsa.2010.1624 .

[HSDB-1] Entry on buprofezin in the Hazardous Substances Data Bank , accessed November 2, 2015.