Terbufos

Structural formula
General
Surname	Terbufos
other names	S - ( tert -Butylthiomethyl) - O , O -diethyldithiophosphate; S - [(1,1-dimethylethyl) thiomethyl] - O , O -diethyldithiophosphate; Counter;
Molecular formula	C 9 H 21 O 2 PS 3
Brief description	colorless to yellowish liquid
External identifiers / databases
EC number	235-963-8
ECHA InfoCard	100.032.679
PubChem	25670
Wikidata	Q2404344
properties
Molar mass	288.44 g mol −1
Physical state	liquid
density	1.105 g cm −3
Melting point	−29.2 ° C
boiling point	69 ° C (0.01 hPa)
Vapor pressure	0.0346 Pa (25 ° C)
solubility	practically insoluble in water (4.5 mg l −1 at 20 ° C); soluble in most organic solvents;
Refractive index	1.52 (23 ° C)
safety instructions
H and P phrases	H: 300-310-410
	P: 264-273-301 + 310-302 + 350-310
Toxicological data	1.6 mg kg −1 ( LD 50 , rat , oral ) ; 1.1 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Terbufos is a chemical compound from the group of thiophosphoric acid esters .

Extraction and presentation

Terbufos can be obtained by reacting O , O -diethyldithiophosphoric acid with formaldehyde and tert - butanethiol .

properties

Terbufos is a yellowish liquid that is practically insoluble in water. If heated for a long time, it decomposes from 120 ° C. When exposed to strong bases (pH> 9) and acids (pH <2) hydrolysis occurs . Two important metabolites of terbufos (terbufos sulfoxide and terbufos sulfone) are poorly soluble in water.

use

Terbufos is used as a pesticide . It is used in the cultivation of sugar beet and fodder beet for seed row treatment with soil cover to control wireworms and moss button beetles as well as beet flies and the black bean louse . The effect is based on the inhibition of acetylcholinesterase .

It was first approved in the United States in 1974 as an insecticide and nematicide to control a wide variety of insects in corn, sugar beet, and sorghum. Between 1987 and 1996, they used an average of about 7.5 million pounds (about 3,400 tons) of the active ingredient per year. In November 2006, BASF sold its global business with the insecticide terbufos to the American AMVAC (American Vanguard Corporation).

Admission

Terbufos is not on the list of active ingredients for pesticides permitted in the European Union . In the EU states including Germany and Austria as well as in Switzerland no pesticides with this active substance are permitted.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on Terbufos in the Hazardous Substances Data Bank , accessed on August 19, 2012.
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on Terbufos in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ ^a ^b Terry R. Roberts, David H. Hutson, Philip W. Lee, Peter H. Nicholls: Metabolic Pathways of Agrochemicals: Part 2: Insecticides and Fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 496 ( limited preview in Google Book search).
↑ Entry on S-tert-butylthiomethyl O, O-diethylphosphorodithioate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 368 ( limited preview in Google Book search).
↑ FAO: TERBUFOS (PDF; 796 kB).
↑ Rudolf Heitefuss: Plant protection: Basics of the practical Phytomedicin . Georg Thieme Verlag, 2000, ISBN 3-13-513303-6 , p. 397 ( limited preview in Google Book search).
↑ EPA: Reregistration Eligibility Decision for Terbufos (PDF; 1.3 MB), July 2006.
↑ Press release BASF: BASF AG | BASF is selling the global business with the insecticide terbufos to AmVac
↑ Regulation (EC) No. 2076/2002 (PDF) of the Commission of November 20, 2002.
↑ General Directorate Health and Food Safety of the European Commission: Entry on Terbufos in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.

[HSDB-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on Terbufos in the Hazardous Substances Data Bank , accessed on August 19, 2012.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on Terbufos in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[Terry_R._Roberts,_David_H._Hutson,_Philip_W_Lee,_Peter_H._Nicholls-3] Terry R. Roberts, David H. Hutson, Philip W. Lee, Peter H. Nicholls: Metabolic Pathways of Agrochemicals: Part 2: Insecticides and Fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 496 ( limited preview in Google Book search).

[CLP_100.032.679-4] Entry on S-tert-butylthiomethyl O, O-diethylphosphorodithioate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[Thomas_A._Unger-5] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 368 ( limited preview in Google Book search).

[FAO-6] FAO: TERBUFOS (PDF; 796 kB).

[Rudolf_Heitefuss-7] Rudolf Heitefuss: Plant protection: Basics of the practical Phytomedicin . Georg Thieme Verlag, 2000, ISBN 3-13-513303-6 , p. 397 ( limited preview in Google Book search).

[EPA_rr-8] EPA: Reregistration Eligibility Decision for Terbufos (PDF; 1.3 MB), July 2006.

[Pressemeldung-9] Press release BASF: BASF AG | BASF is selling the global business with the insecticide terbufos to AmVac

[10] Regulation (EC) No. 2076/2002 (PDF) of the Commission of November 20, 2002.

[PSM-11] General Directorate Health and Food Safety of the European Commission: Entry on Terbufos in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.