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Usage

Uses

Used in Agriculture:
Spirodiclofen is used as an acaricide for controlling red mites in various crops. It is effective against Panonychus spp., Phyllocoptruta spp., Brevipalpus spp., and Aculus and Tetranychus species, helping to protect the crops from these pests and ensuring a healthy yield.
Used in Cannabis Testing:
Spirodiclofen is used in cannabis testing kits as a component of pesticide mixes (P698240). This application helps to ensure the quality and safety of cannabis products by testing for the presence of harmful pesticides, including Spirodiclofen, which can be toxic to humans if ingested in large quantities.

Mode of action

Spirodiclofen is a progenitor of tetronic acid derivates (inhibitors of acetyl CoA carboxylase), characterized by an original (unique) mechanism of action which combines long-lasting protection with anthocorid safety for effective integrated pest management.It interferes/inhibits the lipid biosynthesis of Mites, Mealybugs and Pear-psylla.

InChI:InChI=1/C21H24Cl2O4/c1-4-20(2,3)19(25)26-17-16(14-9-8-13(22)12-15(14)23)18(24)27-21(17)10-6-5-7-11-21/h8-9,12H,4-7,10-11H2,1-3H3

Upstream product

• 5856-77-9 2,2-dimethylbutanoyl chloride 
• 148476-22-6 3-(2,4-dichlorophenyl)-4-hydroxy-1-oxaspiro[4.5]dec-3-en-2-one 
• 1123-28-0 1-hydroxy-cyclohexanecarboxylic acid 
• 931-97-5 1-hydroxy-1-cyclohexanecarbonitrile 
• 19719-28-9 2,4-dichlorophenylacetic acid 
• 6306-60-1 2,4-Dichlorophenylacetonitrile 
• 108-94-1 cyclohexanone 
• 94-99-5 2,4-Dichlorobenzyl chloride 
• 1127-01-1 ethyl 1-hydroxycyclohexanecarboxylate 
• 361366-16-7 1-[2-(2,4-Dichloro-phenyl)-acetoxy]-cyclohexanecarboxylic acid ethyl ester 
• 53056-20-5 2,4-dichlorophenylacetyl chloride 

Relevant academic research and scientific papers

Preparation method of spirodiclofen diester derivative

The invention provides a preparation method of a spirodiclofen diester derivative. The preparation method comprises the following steps: reacting 3-(2, 4-dichlorophenyl)-2-oxo-1-oxaspiro[4, 5]-dec-3-ene-4-ol and acyl chloride serving as raw materials in a hydrophilic aprotic organic solvent with inorganic base as an acid-binding agent, wherein the water content of the reaction system is 5-35% of the total mass of the system; and adding water to crystallize after the reaction is finished, and filtering to obtain a solid-phase product, namely the spirodiclofen diester derivative. The reaction temperature is selected, and the water content in the reaction system is limited, so that the reaction can be smoothly carried out. The technological process is simplified, the method is environment-friendly, and the yield is proved to reach 97% or above and is obviously superior to that of an existing technology.

Production process of high-purity and high-yield spirodiclofen

The invention relates to the technical field of synthesis of compounds and specifically relates to a production process of high-purity and high-yield spirodiclofen. The production process comprises the following steps: performing an addition reaction on cyclohexanone which is taken as a starting material, so as to obtain 1-cyano-cyclohexanol; hydrolyzing and esterifying the 1-cyano-cyclohexanol, so as to obtain 1-hydroxylethyl formate; performing a condensation ring-closing reaction on the 1-hydroxylethyl formate, so as to obtain an intermediate caproate; and performing a reaction on the caproate and 2, 2-dimethylbutyryl chloride, so as to obtain the spirodiclofen. According to the production process, the problem in the prior art that the prepared spirodiclofen is low in purity and yield is solved; the spirodiclofen prepared by adopting the production process is high in purity and yield; and in addition, the raw material for preparing the spirodiclofen is easily obtained, and the operation is convenient.

Preparation method of spirodiclofen and intermediate of spirodiclofen

The invention discloses a preparation method of spirodiclofen and an intermediate of spirodiclofen. The intermediate of spirodiclofen is 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4,5]dec-3-ene-4-ol. Thepreparation method comprises the following steps: ethyl or methyl hydroxycyclohexanoate and 2,4-dichlorophenylacetic acid are esterified under the action of a dehydrating agent and then subjected tocyclization reaction, and 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4,5]dec-3-ene-4-ol is generated. Compared with a traditional process, the synthesis process has the advantages of relatively short synthesis route, simple treatment process, greatly shortened production cycle, obviously increased total yield, reduced production cost and relatively reduced waste water and waste material emissions, and is environmentally friendly accordingly.

NOVEL FORM OF SPIRODICLOFEN, A PROCESS FOR ITS PREPARATION AND USE THE SAME

A new crystalline form of spirodiclofen of formula (I), the crystal preparation process, the analyses of the crystal through various analytical methods and using the crystal to prepare stable agrochemical formulation. The invention also describes the use of various solvents towards the crystalline form preparation conditions.

Spirodiclofen synthetic method

The invention discloses a synthesis method of spirodiclofen. The synthesis method comprises the following steps: enabling 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4,5]-deca-3-ene4-ol and 2-2-dimethylbutyl chloride serving as raw materials to have a reaction in the presence of triethylamine serving as a catalyst in a non-proton type organic solvent; after the reaction is over, regulating the pH value of the reaction liquid to 10-11 with alkali liquid, standing for layering to obtain an aqueous phase and an organic phase, and separating out the aqueous phase as the alkali liquid in next batch of synthesis; washing the organic phase with water, drying with anhydrous sodium sulfate, heating and performing atmospheric distillation to remove a mixed solvent containing triethylamine and the non-proton type organic solvent, so as to obtain a solid product, wherein the removed mixed solvent is used as the catalyst and non-proton type organic solvent in next batch of synthesis; and recrystallizing the obtained solid product to obtain the product spirodiclofen. Triethylamine and dichloromethane are recovered together and directly utilized in next batch of synthesis, so that the production cost is lowered, and the emission of high-concentration brine waste water can be reduced.

Spirodiclofen and spiromesifen - Novel acaricidal and insecticidal tetronic acid derivatives with a new mode of action

The broad spectrum acaricides spirodiclofen (BAJ2740, trade name: Envidor) and spiromesifen (BSN2060, trade name: Oberon) with an additional excellent activity against whiteflies, both belong to the new chemical class of tetronic acid derivatives discovered at Bayer CropScience during the 1990s. The discovery process starting from herbicidal PPO (protoporphyrinogen oxidase) chemistry, the synthetic routes leading to the products, and some insight into process development of central intermediates is given. Spirodiclofen and spiromesifen have a new mode of action (interference with lipid biosynthesis), show no cross-resistance to any resistant mite or whitefly field population and are therefore valuable tools for resistance management.