87820-88-0

Basic information

• Product Name: Tralkoxydim
• Synonyms: 2-[1-(Ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethylphenyl)cyclohex-2-enone;ACHIEVE;GRASP;TRALKOXIDYM;TRALKOXYDIM;TRALKOXYDIME;2-(1-(ethoxyimino)propyl)-3-hydroxy-5-(2,4,6-trimethylphenyl)-2-cyclohexen-1;2-(1-(ethoxyimino)propyl)-3-hydroxy-5-mesitylcyclohex-2-enone
• CAS NO: 87820-88-0
• Molecular Formula: C₂₀H₂₇NO₃
• Molecular Weight: 329.43
• EINECS: 252-615-0
• Product Categories: Cyclohexene oximePesticides&Metabolites;TP - TZ;Alpha sort;Herbicides;Pesticides&Metabolites;Q-ZAlphabetic
• Mol File: 87820-88-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 106°
• Boiling Point: 467.02°C (rough estimate)
• Flash Point: >100 °C
• Appearance: White Crystalline Powder
• Density: 1.1213 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• Storage Temp.: 0-6°C
• Solubility: soluble in dichloromethane,Toluene,Acetone
• PKA: 4.20±0.25(Predicted)
• Merck: 14,9564
• BRN: 8577523
• CAS DataBase Reference: Tralkoxydim(CAS DataBase Reference)
• NIST Chemistry Reference: Tralkoxydim(87820-88-0)
• EPA Substance Registry System: Tralkoxydim(87820-88-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• RTECS: GW7191600
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 87820-88-0(Hazardous Substances Data)

Usage

Physical and Chemical Properties

Appearance: White tasteless crystalline solid Melting Point: 106℃ Saturated Vapor Pressure: 4×10-7Pa (<0.013×10-3Pa 20℃) Solubility: 4×10-7Pa (<0.013×10-3Pa 20℃) in dichloromethane at 24℃, 213g/L in methylbenzene at 24℃, 110g/L in ethyl acetate at 24℃, 89g/L in acetone at 24℃, 25g/L in methanol at 24℃, 18g/L in hexane at 24℃. 6mg/L (pH=6.5) and 5mg/L (pH=5.0) in water at 20℃

InChI Code

1S/C20H27NO3/c1-6-16(21-24-7-2)20-17(22)10-15(11-18(20)23)19-13(4)8-12(3)9-14(19)5/h8-9,15,22H,6-7,10-11H2,1-5H3

Toxicity

P.O. acute toxicity： LD50=1324mg/kg for male rats, LD50=934mg/kg for female rats,? LD50=1321mg/kg for male mice, LD50=1100mg/kg for female mice, LD50>519mg/kg for rabbits. Non-effect dose for rats in three-month feed test is 12.5mg/kg. LD50=3020mg/kg for mallard, LD50=4430mg/kg for partridge. Acute percutaneous toxicity: LD50>2000mg/kg for male and female rats. Acute inhalation toxicity: LC50>3467mg/m3 for male and female rats. It has mild irritation on eyes and skin. No allergic effect on cavy. No teratogenesis effect has been observed yet. LC50>7.2mg/L (96h) for rainbow trout, LC50>8.2mg/L (96h) for Cyprinus carpio var.

Application

Tralkoxydim is a kind of highly selective herbicide with inward absorption and conduction ability. It’s used on a variety of graminaceous weeds in barley and wheat fields. It is rapidly absorbed and transferred throughout all parts of the weeds after foliar spray. The weeds will soon turn pale and wither. The general dosage is 150～350g effective constituent/hm2 . 200～350g effective constituent /hm2 of tralkoxydim applied from early growth period to elongation stage will be effective on the prevention and control of wild oat weeds.

Synthesis

The product of the reaction between 2,4,6-Trimethylbenzaldehyde and acetone react with diethyl malonate to generate an intermediate. The intermediate is transformed into 3-hydroxy-5-（2',4',6'-trimethylphenyl）-cyclohexyl-2-alkenyl-1-ketone after hydrolysis, cyclization and decarboxylation. Then it reacts with propionic anhydride in the presence of sodium methanol. The product reacts with ethoxyamine hydrochloride to generate methoxyphenone.

Agricultural Uses

Herbicide: Tralkoxydim is a post-emergent herbicide applied to actively growing weeds in wheat, barley, triticale and cereal rye to control wild oats, green foxtail, yellow foxtail, annual ryegrass and Persian darnel. Registered for use in EU countries. Registered for use in the U.S.

Trade name

ACHIEVE?; ACHIEVE?-40DG; ALPHA GRASP?; ICI-A 604?; PP 604?; SPLENDOR?

InChI:InChI=1/C20H27NO3/c1-6-16(21-24-7-2)20-17(22)10-15(11-18(20)23)19-13(4)8-12(3)9-14(19)5/h8-9,15,22H,6-7,10-11H2,1-5H3/b21-16+

Upstream product

• 53389-56-3 1-(2,4,6-trimethylphenyl)-1-buten-3-one 
• 487-68-3 mesytaldehyde 
• 87821-75-8 3-hydroxy-5-(2,4,6-trimethylphenyl)-2-propionyl-cyclohex-2-en-1-one 
• 624-86-2 O-ethyl hydroxylamine 

Downstream Products

• 138164-12-2 5-(3-butyryl-2,4,6-trimethylphenyl)-2-[1-(ethoxyimino)propyl]-3-hydroxycyclohex-2-ene-1-one 

Relevant articles and documents

Preparation method of tralkoxydim

The invention discloses a method for preparing tralkoxydim. The method comprises the following steps: preparing a first intermediate from 2,4,6-trimethylbenzaldehyde and acetone; preparing a second intermediate from the first intermediate, diethyl malonate and propionyl chloride; and preparing tralkoxydim by utilizing the second intermediate and ethoxyamine, wherein in the process of preparing the second intermediate, a condensation reaction and a rearrangement reaction are carried out at the same time, and after the first intermediate is prepared and before tralkoxydim is prepared, separation or purification treatment is not carried out. According to the invention, tralkoxydim is prepared by simultaneously carrying out condensation and rearrangement reactions and not carrying out a separation or purification process in the reaction process, so the steps of multiple times of separation, purification, transfer, feeding and the like in existing preparation methods are omitted, time and labor are saved, the consumption of reagents is reduced, a large amount of cost is saved, and the problems that a tralkoxydim preparation method is complex in step, product yield is low and layering emulsification is serious in an esterification reaction process in the prior art are solved.