Clethodim Chemical Properties

Melting point:

<25 °C

Boiling point:

472.6±55.0 °C(Predicted)

Density 

1.18±0.1 g/cm3(Predicted)

storage temp. 

0-6°C

solubility 

Chloroform (Sparingly, Sonicated), Ethyl Acetate (Slightly), Methanol (Sparingly

pka

4.28±0.25(Predicted)

color 

Light Yellow to Dark Yellow

Stability:

Hygroscopic

CAS DataBase Reference

99129-21-2(CAS DataBase Reference)

EPA Substance Registry System

Clethodim (99129-21-2)

Safety Information

Safety Statements 

22-24/25

RIDADR 

UN3082 (environmentally haz- ardous substances, liquid, n. o. s.)

WGK Germany 

3

HS Code 

29309090

Hazardous Substances Data

99129-21-2(Hazardous Substances Data)

Toxicity

LD50 in male, female rats (mg/kg): 1630, 1360 orally; LC50 in trout: 56 mg/l; 8 day feeding in quail: > 6000 ppm (Kincade)

Clethodim Usage And Synthesis

Physical and chemical properties

The original medicine is amber transparent liquid with relative density 1.14 (20 ℃) and vapor pressure <1 × 10-2mPa (20 ℃). It is soluble in most organic solvents, stable under ultraviolet light, but unstable at extreme pH.

Toxicity

The acute oral toxicity of original medicine LD50 in rats was 1360 mg / kg (female) , 1630 mg / kg (male). The acute dermal toxicity LD(50) in rabbits was more than 5g/kg. The acute inhalation LC50 in rats (4 hours) is more than 4.6mg/L . No effect dose during Feeding test: rat 16mg / kg • d, mice 30mg / kg • d. ADI by humans is 0.01 mg / kg. The acute oral toxicity LD50 in quails is more than 2g / kg. The acute inhalation LC50 (8 days) in wild ducks and quails is more than 6g / kg. The LC50 in daphnias is > 120mg / L. The LD50 in insects is 454 mg / kg. The LC50 in blue gill fish (96 hours)is > 120mg / L, The LC50 in rainbow trout is 5056mg / L. The LD50 in bees is > 100μg per bee.

Mode of action

It is a selective, systemic post-emergence herbicide which can be rapidly absorbed by plant leaves and conducted to roots and growing points to inhibit the biosynthesis of plant branched-chain fatty acids. The target weeds then grow slowly and lose competitiveness with seedling tissue early yellowing and followed by the remaining leaves wilting. Finally they will die.

Target plants

Suitable for broad-leaf plants. All tested plants of non-grass family were highly resistant to RE-45601 throughout the entire growth and development period, even applied with 2 kg ai / hm2 (8-20 times higher than herbicides) plus vegetable oil 2.341 / hm2, the situation still remains the same.
Soybeans and cotton can be sowed immediately after application of RE-45601. Other crops can be sowed 4 months after application of RE-45601 at a dose of 1.12 kg ai / hm2 or less.

Application

Applicable to annual and perennial grass weeds and many Field maize cereals withbroad-leaf. (1) annual species (84-140 g ai / hm2): Kusamiligus ostreatus, wild oats, wool millet, brachiopod, mangrove, black brome, ryegrass, gall grass, French foxtail, hemostatic horse, Golden Foxtail, Crabgrass, Setaria viridis, Echinochloa crus-galli, Dichromatic Sorghum, Barnyardgrass, Wheat, Lemna, Corn; Barley , (2) Arabian sorghum of perennial species (84-140 g ai / hm2); (3) Perennial species (140 ~ 280g ai / hm2) bermudagrass, creeping wild wheat.
It’s not or slightly active against broad-leaf weeds or Carex. The crops of grass family such as barley, corn, oats, rice, sorghum and wheat are all susceptible to RE-45601. Therefore the autogenesis plants in the filed where crops of non-grass family can be controlled with RE-45601.

How to use

RE-45601 gets the best control effect during the period when grass weeds grow vigorously. Drought, low temperature (below 15 ° C) and other unfavorable factors sometimes reduce the activity of RE-45601. For annual weeds of grass family, it should be applied during the 3 to 5 leaf stage. For perennial weeds of grass family, herbicide should be applied after weeds tillering; increase of the dose or number of applications is needed for non- appropriate period for spraying. If an even distribution of droplets can be applied, low spray volume (ie 50L / hm2)is more effective than the high spray volume (180 ~ 280L / hm2). The biological activity can be improved by adding vegetable oil 2.34L / hm2. The active ingredient in RE-45601 is absorbed by plants within 1 hour, so the rainfall after application will not reduce the effect.

Preparation Methods

5-alkylcyclohexanedione-3-carboxylate is produced by the condensation and cyclization of the corresponding ketene and diethyl malonatein the presence of sodium hydroxide, then compound(Ⅰ) is obtained by hydrolysis and decarboxylation, followed by its reaction with propionyl chloride to form 3-propionyloxy-5-alkylcyclohexenone which is soluble in methylene chloride . then has isomerization reaction in the presence of aluminum trichloride and finally reacts with H2NOCH2CH = CHCl to produce,clethodim. The response equation is as follows:

Chemical Properties

Clear Yellow Oil

Uses

Systemic graminicide. Post-emergent herbicide.

Definition

ChEBI: Clethodim is an oxime O-ether resulting from the formal conversion ot the acyclic keto group of 5-[2-(ethylsulfanyl)propyl]-3-hydroxy-2-propionylcyclohex-2-en-1-one to the corresponding oxime with subsequent O-alkylation of the oxime by an (E)-3-chloroallyl group. It is used as a selective postemergence herbicide for the control of annual and perennial grasses in numerous crops, including alfalfa, celery, clover, conifers, cotton, cranberries, garlic, onions, ornamentals, peanuts, soybeans, strawberries, sugarbeet, sunflowers, and vegetables; the (-)-enantiomer has been reported to be more active than the (+)-enantiomer. It has a role as a herbicide and an EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor. It is an organic sulfide, a cyclic ketone, an organochlorine compound, an oxime O-ether, a beta-diketone and an enol.

Agricultural Uses

Herbicide: Not approved for use in EU countries. A selective post-emergence herbicide used to control annual and perennial grasses to a range of crops including cotton, flax, peanuts, soybeans, sugarbeets, potatoes, alfalfa, sunflowers and most vegetables.

Trade name

CLETODIME®; PRISM®; RE 45601; SELECT®

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