148477-71-8

Basic information

• Product Name: Spirodiclofen
• Synonyms: SPIRODICLOFEN;3-(2,4-DICHLOROPHENYL)-2-OXO-1-OXASPIRO[4.5]DEC-3-EN-4-YL) 2,2-DIMETHYLBUTYRATE;Spirodiclofen, Pestanal;SPIRODICLOFEN 10 NG/UL PESTANAL;baj2740;spirodiclofen(bsi, pa iso);[3-(2,4-Dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl] 2,2-dimethylbutanoate;Spirodiclofen solution
• CAS NO: 148477-71-8
• Molecular Formula: C₂₁H₂₄Cl₂O₄
• Molecular Weight: 411.32
• EINECS: 203-625-9
• Product Categories: Pesticide intermediates;Agrochemical
• Mol File: 148477-71-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 101-108°
• Boiling Point: 561.1 °C at 760 mmHg
• Flash Point: 4 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 3.73E-12mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), DMSO, Methanol (Sparingly)
• CAS DataBase Reference: Spirodiclofen(CAS DataBase Reference)
• NIST Chemistry Reference: Spirodiclofen(148477-71-8)
• EPA Substance Registry System: Spirodiclofen(148477-71-8)

Safety Data

• Hazard Codes: Xi,Xn,F
• Statements: 43-67-65-63-48/20-38-11
• Safety Statements: 36/37-62
• RIDADR: UN1294 3/PG 2
• WGK Germany: 2
• Hazardous Substances Data: 148477-71-8(Hazardous Substances Data)

Usage

Description

Spirodiclofen is a new selective, non systemic acaricide belonging to the chemical group of the spirocyclic tetronic acid derivatives. It acts by interfering with mite development, thereby controlling such pests as Panonychus spp., Phyllocoptruta spp., Brevipalpus spp., and Aculus and Tetranychus species. Spirodiclofen is active by contact to mite eggs, all nymphal stages, and adult females (adult males are not effected). Spirodiclofen is structurally similar to spiromesifen, which is also a tetronic acid insecticide. Spirodiclofen is registered worldwide for use on a variety of crops including citrus, pome fruits, stone fruits, grapes and ornamentals.

Uses

Spirodiclofen is a tetronic acid acaricide fungicide used in controlling red mites. Spirodiclofen is used in cannabis testing kits as a component of pesticide mixes (P698240).

Definition

ChEBI: Spirodiclofen is an organochlorine acaricide, a dichlorobenzene, an oxaspiro compound and a gamma-lactone. It derives from a 1,3-dichlorobenzene.

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

• 94-99-5 2,4-Dichlorobenzyl chloride 
• 108-94-1 cyclohexanone 
• 1127-01-1 ethyl 1-hydroxycyclohexanecarboxylate 
• 6306-60-1 2,4-Dichlorophenylacetonitrile 
• 19719-28-9 2,4-dichlorophenylacetic acid 
• 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 
• 53056-20-5 2,4-dichlorophenylacetyl chloride 
• 361366-16-7 1-[2-(2,4-Dichloro-phenyl)-acetoxy]-cyclohexanecarboxylic acid ethyl ester 
• 931-97-5 1-hydroxy-1-cyclohexanecarbonitrile 

Relevant articles and documents

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.

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.

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.