81008-52-8

Usage

InChI:InChI=1/C9H16OS/c1-4-11-9(3)7-5-6-8(2)10/h5-6,9H,4,7H2,1-3H3

Upstream product

• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 27205-24-9 β-(ethylthio)butyraldehyde 
• 623-58-5 sodium aceto-acetate 
• 67-64-1 acetone 
• 3916-64-1 hepta-3,5-dien-2-one 
• 75-08-1 ethanethiol 

Downstream Products

• 111031-74-4 (±)-2-[propionyl]-3-[hydroxy]-5-[2-(ethylthio)propyl]cyclohex-2-enone 
• 364339-22-0 C₁₃H₂₀O₄S 
• 87476-15-1 5-[2-(ethylthio)-propyl]-1,3-cyclohexanedione 
• 1067594-01-7 2-(2,6-diethyl-4-methylphenyl)-5-[2-(ethylthio)propyl]cyclohexane-1,3-dione 
• 1067600-27-4 2-(2,6-diethyl-4-methylphenyl)-5-[2-(ethylsulfinyl)propyl]-cyclohexane-1,3-dione 
• 1067606-17-0 2-(2,6-diethyl-4-methylphenyl)-5-[2-(ethylsulfonyl)propyl]cyclohexane-1,3-dione 
• 99129-21-2 clethodim 

Relevant academic research and scientific papers

Synthesis method of 6-ethylthio-3-hepten-2-one

The invention discloses a synthesis method of 6-ethylthio-3-hepten-2-one, which comprises the following steps: taking acetone and 3-ethylthiobutyraldehyde as raw materials, and carrying out one-step reaction in the presence of a catalyst to obtain the 6-ethylthio-3-hepten-2-one, wherein the catalyst is a nitrogen-containing alkali catalyst. The target product can be obtained through one-pot one-step reaction, operation is simple, the catalyst can be recycled, other byproducts cannot be generated, and the method is environmentally friendly, low in cost and high in economic value and is an ideal route.

Cyclohexyl clethodim synthesis process

The invention relates to a cyclohexyl clethodim synthesis process, which comprises: (1) preparing 3-ethylthiobutyraldehyde by using ethanethiol and crotonaldehyde as raw materials; 2) carrying out a reaction on the 3-ethylthiobutyraldehyde and sodium acetoacetate by using secondary amine as a catalyst to prepare 6-ethylthio-3-heptene-2-one; 3) carrying out addition cyclization on the 6-ethylthio-3-heptene-2-one and diethyl malonate, and carrying out hydrolysis decarboxylation to obtain 5-(2-ethylthiopropyl)cyclohexane-1,3-dione; 4) carrying out O-acylation on the 5-(2-ethylthiopropyl)cyclohexane-1,3-dione through propionyl chloride, and carrying out rearrangement to obtain acylated 5-(2-ethylthiopropyl)-2-propionyl-3-hydroxy-2-cyclohexene-1-one; and 5) carrying out a reaction on the 5-(2-ethylthiopropyl)-2-propionyl-3-hydroxy-2-cyclohexene-1-one and 3-chloro-2-propenyl amine hydrochloride to prepare clethodim. According to the invention, the clethodim crude oil with a content of largerthan 97% is obtained by using ethanethiol and crotonaldehyde as the raw materials through the five-step reaction, wherein the total yield is larger than 62%, and the two-step yield of the intermediate 3-chloro-2-propenyl hydroxylamine is larger than 92%; and the method can be used for industrial production and has a good market prospect.

Method for synthesizing cyclohexenone herbicide key intermediate

The invention provides a method for synthesizing a cyclohexenone herbicide key intermediate which is 6-ethylsuleenyl-3-heptylene-2-ketone. The method for preparing 6-ethylsuleenyl-3-heptylene-2-ketone comprises the following steps: (1) carrying out aldol condensation via crotonaldehyde and acetone under catalysis of alkali to synthesize a compound which is 3,5-heptadiene-2-ketone of formula (I), wherein the reaction route is expressed as a formula which is as shown in the description; and (2) carrying out nucleophilic addition via 3,5-heptadiene-2-ketone and ethanethiol to prepare the cyclohexenone herbicide key intermediate which is 6-ethylsuleenyl-3-heptylene-2-ketone, wherein the reaction route is expressed as a formula which is as shown in the description. The 6-ethylsuleenyl-3-heptylene-2-ketone prepared by the method is high in yield and high in purity; the method is simple in process, cheap and easily available in raw materials, low in production cost and low in environment pollution, and is suitable for large-scale production.

A method for synthesizing alkene grass alkone (by machine translation)

The invention provides a method for synthesizing alkene grass alkone, comprises a 3, 5 - heptadiene - 2 - one (type II) with the odorant to the nucleophilic addition reaction on the alkene grass alkone intermediate 6 - ethylthio - 3 - hepten - 2 - one (formula III); type III with malonic acid dimethyl ester, propionyl chloride reaction intermediates prepared by IV (±) - 3 - [c acyloxy] - 5 - [2 - (ethylthio) propyl] - 6 - [a oxygen formacyl] cyclohex - 2 - enone (formula V); type V through the rearrangement, hydrolysis, decarboxylation reaction (±) - 2 - [propionyl] - 3 - [hydroxy] - 5 - [2 - (ethylthio) propyl] cyclohex - 2 - enone (formula VIII); type VIII chloro- alkene third oxygen amine reaction with the alkene grass alkone (type I), this invention adopts the intermediate 3, 5 - heptadiene - 2 - one (formula II) preparing alkene grass alkone method is proposed for the first time, is prepared by this method (type I) alkene grass alkone overall high yield, the product quality is good, and the method has low production cost, environmental pollution is small, is suitable for mass production. (by machine translation)

NOVEL HERBICIDES

Cyclohexanedione compounds, and derivatives thereof, which are substituted in 5-position, are suitable for use as herbicides.

Use of resistant ACCase mutants to screen for novel inhibitors against resistant and susceptible forms of ACCase from grass weeds

The aryloxyphenoxypropionic acid (AOPP) and cyclohexanedione (CHD) herbicides inhibit the first committed enzyme in fatty acid biosynthesis, acetyl CoA carboxylase (ACCase). The frequent use of AOPP and CHD herbicides has resulted in the development of resistance to these herbicides in many grass weed species. New herbicides that inhibit both the susceptible and resistant forms of ACCase in grass weeds would have obvious commercial appeal. In the present study, an attempt was made to identify molecules that target both the herbicide-sensitive and -resistant forms of ACCase. Seven experimental compounds, either CHD-like or AOPP-CHD hybrids, were synthesized and assayed against previously characterized susceptible and resistant forms of ACCase. All seven compounds inhibited ACCase from sensitive biotypes of Setaria viridis and Eleusine indica (I50 values from 6.4 to > 100 μM) but were not particularly potent compared to some commercialized herbicides (I50 values of 0.08-5.6 μM). In almost all cases, the I50 values for each compound assayed against the resistant ACCases were higher than those against the corresponding sensitive ACCase, indicating reduced binding to the resistant ACCases. One compound, a CHD analogue, was almost equally effective against the resistant and susceptible ACCases, although it was not a very potent ACCase inhibitor per se I50 of 51 and 76 μM against susceptible ACCase from S. viridis and E. indica, respectively). The AOPP-CHD hybrid molecules also inhibited some of the resistant ACCases, with I50 values ranging from 6.4 to 50 μM. These compounds may be good leads for developing ACCase inhibitors that target a wider range of ACCase isoforms, including those found in AOPP- and CHD-resistant weed biotypes.

Herbicidal substituted 2-(1-(oxyamino)-alkylidene)-cyclohexane-1,3-diones

Substituted 2-[1-(oxyamino)alkylidene]-cyclohexane-1,3-diones have herbicidal activity against grassy weeds.