148476-22-6

Basic information

• Product Name: 3-(2,4-Dichlorophenyl)-4-hydroxy-1-oxaspiro(4,5)dec-3-en-2-one
• Synonyms: 1-Oxaspiro(4,5)dec-3-en-2-one, 3-(2,4-dichlorophenyl)-4-hydroxy-;3-(2,4-Dichlorophenyl)-4-hydroxy-1-oxaspiro(4,5)dec-3-en-2-one
• CAS NO: 148476-22-6
• Molecular Formula: C₁₅H₁₄Cl₂O₃
• Molecular Weight: 313.17586
• Mol File: 148476-22-6.mol

Chemical Properties

• Melting Point: approximate 255℃ (dec.)
• Boiling Point: 506.4°C at 760 mmHg
• Flash Point: 260°C
• Appearance: /
• Density: 1.44g/cm³
• Vapor Pressure: 4.47E-11mmHg at 25°C
• Refractive Index: 1.628
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 3-(2,4-Dichlorophenyl)-4-hydroxy-1-oxaspiro(4,5)dec-3-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2,4-Dichlorophenyl)-4-hydroxy-1-oxaspiro(4,5)dec-3-en-2-one(148476-22-6)
• EPA Substance Registry System: 3-(2,4-Dichlorophenyl)-4-hydroxy-1-oxaspiro(4,5)dec-3-en-2-one(148476-22-6)

Safety Data

• Hazardous Substances Data: 148476-22-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(2,4-Dichlorophenyl)-4-hydroxy-1-oxaspiro(4,5)dec-3-en-2-one is used as an active pharmaceutical ingredient (API) for its potential therapeutic effects. The compound's unique structure allows it to interact with specific biological targets, making it a promising candidate for the development of new drugs to treat various diseases.
Used in Agrochemical Industry:
In the agrochemical industry, 3-(2,4-Dichlorophenyl)-4-hydroxy-1-oxaspiro(4,5)dec-3-en-2-one is used as a key intermediate in the synthesis of acaricides, specifically for the production of O-Des-(2,2-methylbutyryl) Spirodiclofen. This metabolite of Spirodiclofen (S682990) is effective in controlling red mites, which are harmful to both animals and plants.
Used in Chemical Research:
3-(2,4-Dichlorophenyl)-4-hydroxy-1-oxaspiro(4,5)dec-3-en-2-one is also utilized in chemical research as a starting material or intermediate for the synthesis of other complex organic compounds. Its unique structure and reactivity make it a valuable tool for exploring new chemical reactions and developing novel molecules with potential applications in various fields.

InChI:InChI=1/C15H14Cl2O3/c16-9-4-5-10(11(17)8-9)12-13(18)15(20-14(12)19)6-2-1-3-7-15/h4-5,8,18H,1-3,6-7H2

Upstream product

• 108-94-1 cyclohexanone 
• 19719-28-9 2,4-dichlorophenylacetic acid 
• 1127-01-1 ethyl 1-hydroxycyclohexanecarboxylate 
• 53056-20-5 2,4-dichlorophenylacetyl chloride 
• 55954-23-9 methyl 2-(2,4-dichlorophenyl)acetate 
• 6149-50-4 methyl 1-hydroxycyclohexanecarboxylate 
• 94-99-5 2,4-Dichlorobenzyl chloride 
• 6306-60-1 2,4-Dichlorophenylacetonitrile 
• 931-97-5 1-hydroxy-1-cyclohexanecarbonitrile 
• 1123-28-0 1-hydroxy-cyclohexanecarboxylic acid 
• 361366-16-7 1-[2-(2,4-Dichloro-phenyl)-acetoxy]-cyclohexanecarboxylic acid ethyl ester 

Downstream Products

• 148477-71-8 spirodiclofen 
• 1256911-62-2 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl ethyl carbonate 
• 1256911-67-7 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl 4-fluorobenzoate 
• 1256911-66-6 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl 3,4,5-trimethoxybenzoate 
• 1256911-61-1 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl methanesulfonate 
• 1256911-65-5 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl 2-o-tolylacetate 
• 1256911-63-3 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl 2-phenylacetate 
• 1256911-64-4 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl 2-(2,4-dichlorophenyl)acetate 

Relevant articles and documents

Synthesis and Acaricidal Activity of Aryl-Spirobutyrolactone Derivatives against Spider Mites under Greenhouse and Field Conditions

Abstract: Propesticides play an important role in modern agrochemicals research and development. In the controlling of harmful insects and mites in agriculture, propesticide strategy offers a unique and modern approach to acaricide development. In this study, a series of aryl-spirobutyrolactone pharmacophore based alkylated compounds were synthesized and characterized by 1H NMR and ESI-MS. All of this compounds exhibited excellent acaricidal activities against Tetranychus cinnabarinus at 2.5 mg/L in greenhouse test, and some of them showed better activity than spirodiclofen against eggs of T. cinnabarinus at 0.625 mg/L. In the field trials, compounds (Vc), (Ve) and (Vf) were evaluated against Panonychus ulmi and Panonychus citri at three different concentrations. The results showed that compounds (Ve) and (Vf) have the potential to develop into new proacaricide with further test and toxicity evaluation.

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.

Method for synthesizing key intermediate of pesticide spirodiclofen

The invention discloses a method for synthesizing a key intermediate of pesticide spirodiclofen and relates to the technical field of organic synthesis. It is founded, by the dxperiments, that the fineness of an acid binding agent has very great influences on reaction and the reaction speed and the reaction yield are obviously improved along continuous reduction of the fineness. According to the method disclosed by the invention, alkali, which has the fineness lower than 80 meshes after being crushed, is used as the acid binding agent in synthesis reaction and is used for replacing flake-shaped or grain-shaped alkali. The method provided by the invention has the main advantage that the yield of a product is improved.

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.

A group of pyrazole acid oxo spiro-heterocycle ester derivatives and preparing method and application thereof

The invention relates to a group of pyrazole acid oxo spiro-heterocycle ester derivatives which has the following structures(the specific structures are in the specification). In the pyrazole acid oxo spiro-heterocycle ester derivatives, R, Y and Xm perssad are chosen from specific definitions in the specification. The invention discloses the structures and control efficiencies of on agricultural pests of the compounds, and discloses applications of the compounds as insecticides.

Novel ether-functional spiro-tetronic acid derivatives: Molecule design, convenient synthesis and biological evaluation

A novel series of ether functionalization of spiro-tetronic acid derivatives have been designed and conveniently synthesized via three steps, including esterification, one-pot heterocyclization, and etherification reactions. The target molecules have been identified on the basis of analytical spectra data. All newly synthesized compounds have been screened for their potential insecticidal activity against Heliothis armigera and Plutella xylostella compared with spirodiclofen by standard method. Springer Science+Business Media B.V. 2012.

Spirodiclofen analogues as potential lipid biosynthesis inhibitors: A convenient synthesis, biological evaluation, and structure-activity relationship

Twenty spirodiclofen analogues have been designed and conveniently synthesized via three steps including esterification, one-pot heterocyclization, and acylation reactions. The target molecules have been identified on the basis of analytical spectra (1H NMR, 13C NMR and ESI-MS) data. All newly synthesized compounds have been screened for their potential insecticidal and herbicidal activity by standard method. The preliminary assays indicated that some of analogues displayed moderate to good insecticidal activity against Plutella xylostella compared with spirodiclofen, and some compounds showed obvious activity against Brassica chinensis. Structure-activity relationship (SAR) is also discussed based on the experimental data.

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.