Bifenazate

Structural formula
General
Surname	Bifenazate
other names	Isopropyl N - (4-methoxybiphenyl-3-yl) hydrazine-carboxylate Isopropyl 2- (4-methoxy-1,1'-biphenyl-3-yl) hydrazine carboxylate Floramite
Molecular formula	C 17 H 20 N 2 O 3
Brief description	white crystals, technical beige powder
External identifiers / databases
CAS number 149877-41-8 EC number 442-820-5 ECHA InfoCard 100.103.840 PubChem 176879 ChemSpider 154052 Wikidata Q13439316
properties
Molar mass	300.35 g mol −1
Physical state	firmly
density	1.31 g cm −3
Melting point	120-124 ° C
boiling point	decomposes before boiling at 240 ° C
Vapor pressure	1.33 10 −5 hPa (20 ° C)
solubility	practically insoluble in water (2.06 mg l −1 at 20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 373-317-410 P: 261-273-280-333 + 313
Toxicological data	> 5000 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bifenazate is a chemical compound from the group of carbazates and hydrazine carboxylic acid esters .

discovery

Bifenazate was discovered in 1990 by Uniroyal Chemical Co. Inc. (now Chemtura ) and jointly developed with Nissan Chemical . It was first marketed in 2000.

properties

Bifenazate is a white to beige, crystalline solid. While it is practically insoluble in water (2.06 mg l ⁻¹ at 20 ° C), it dissolves little in toluene (25.7 g l ⁻¹ ) and dissolves in methanol (44.7 g l ⁻¹ ) ⁻¹ ) and is easily soluble in acetone (210.7 g · l ⁻¹ ) and ethyl acetate (102.0 g · l ⁻¹ ). With half-lives of 4.8 days in the field trial, the compound is not persistent. It is also sensitive to hydrolysis and unstable to light .

Mode of action and use

Bifenazate is a non-systemic acaricide with long lasting effects. It is a fast-acting contact poison with a knock-down effect. With Bifenazat all mite stages as well as the larvae eggs can be combated. The mechanism of action is believed to be based on the inhibition of mitochondrial complex III .

Bifenazat can be used against various types of mites such as Tetranychus spp. (e.g. spider mites ) or Oligonychus spp. be used. It is used in the cultivation of fruit, vegetables, hops and wine as well as ornamental plants.

Admission

In Germany, Austria and Switzerland, as well as in other EU countries, plant protection products with this active ingredient are approved.

Individual evidence

1. ↑ ^{a b c d e} Entry on bifenazate. In: Römpp Online . Georg Thieme Verlag, accessed on April 22, 2014.
2. ↑ ^{a b c d e f g} Entry on Bifenazate in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on May 13, 2020.
3. ↑ Entry on bifenazate in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
4. ↑ Entry on bifenazate (ISO); isopropyl 2- (4-methoxybiphenyl-3-yl) hydrazinecarboxylate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on May 13, 2020. Manufacturers or distributors can expand the harmonized classification and labeling .
5. ↑ Bifenazate data sheet from Sigma-Aldrich , accessed on May 13, 2020 ( PDF ).
6. ↑ James A. Turner: The Pesticide Manual: A World Compendium . Seventeenth ed.British Crop Production Council, Alton, Hampshire, UK 2015, ISBN 978-1-901396-88-1 , pp. 104 f .
7. ↑ Ishaaya, I., Horowitz, A. Rami, 1942-: Biorational control of arthropod pests: application and resistance management . Springer, Dordrecht 2009, ISBN 978-90-481-2316-2 ( limited preview in Google book search).
8. ^ P. Van Nieuwenhuyse, P. Demaeght, W. Dermauw, M. Khalighi, CV Stevens: On the mode of action of bifenazate: New evidence for a mitochondrial target site . In: Pesticide Biochemistry and Physiology (=  Special Issue: Molecular Approaches to Pest Control, Toxicology and Resistance ). tape 104 , no. 2 , October 1, 2012, ISSN  0048-3575 , p. 88-95 , doi : 10.1016 / j.pestbp.2012.05.013 ( sciencedirect.com [accessed May 15, 2020]).
9. ^ Directorate-General for Health and Food Safety of the European Commission: Entry on Bifenazate in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 16, 2016.