4693-00-9

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Dichloroisatoic Anhydride is used as a reagent in the synthesis of various pharmaceutical compounds. Its role in organic synthesis allows for the creation of new drug molecules, contributing to the development of novel treatments and therapies.
Used in Scientific Research:
In the field of scientific research, 3,5-Dichloroisatoic Anhydride is employed as a reagent for conducting experiments and studying chemical reactions. Its involvement in organic synthesis helps researchers understand the behavior of different compounds and develop new methodologies for chemical processes.

InChI:InChI=1/C8H3Cl2NO3/c9-3-1-4-6(5(10)2-3)11-8(13)14-7(4)12/h1-2H,(H,11,13)

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 2789-92-6 3,5-dichloroantranilic acid 
• 124-38-9 carbon dioxide 
• 201230-82-2 carbon monoxide 
• 697-90-5 2,4-dichloro-6-iodoaniline 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 36765-01-2 2-amino-3,5-dichlorobenzamide 
• 91-56-5 indole-2,3-dione 
• 75-44-5 phosgene 
• 6371-38-6 5,7,5',7'-tetrachloro-1H,1'H-[2,2']biindolylidene-3,3'-dione 
• 6374-92-1 5,7-dichloroisatin 

Downstream Products

• 109047-41-8 1-(2-amino-3,5-dichloro-benzoyl)-aziridine 
• 56821-48-8 2-Amino-3,5-dichloro-N-morpholin-4-yl-benzamide 
• 81438-27-9 o-Ethoxycarbonylamino-3,5-dichlor-hippursaeuremethylester 
• 1422677-85-7 2-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[(diethyl-λ⁴-sulfanylidene)carbamoyl]phenyl]-5-(trifluoromethyl)-2H-pyrazole-3-carboxamide 
• 1422677-86-8 2-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[(bis-2-propyl-λ⁴-sulfanylidene)carbamoyl]phenyl]-5-(trifluoromethyl)-2H-pyrazole-3-carboxamide 
• 1422677-58-4 2-amino-N-(bis-(2-propyl)-λ⁴-sulfanylidene)-3,5-dichlorobenzamide 
• 1422677-59-5 2-amino-3,5-dichloro-N-(diethyl-λ⁴-sulfanylidene)benzamide 

Relevant academic research and scientific papers

Synthesis, insecticidal activities, and SAR studies of novel piperazine-containing heterocyclic mono-/di-/tri-amide derivatives

Diamide compounds such as chlorantraniliprole, a famous anthranilic diamide insecticide targeting the insect ryanodine receptor (RyR), have received continuous attention in pesticide research during the past 15 years owing to their excellent insecticidal potentials. With the aim of discovering new heterocyclic pesticides used for crop protection, based on the structural information of compound M from the reported pharmacophore-based virtual screening for RyR insecticides and diamide compound, a series of new heterocyclic mono-, di-, and tri-amide derivatives containing piperazine moiety have been synthesized in this paper. The new compounds were identified and confirmed by melting point, 1H NMR, 13C NMR and HRMS. Compound M was firstly validated for insecticidal activities, and the new synthesized compounds were all made comprehensive insecticidal evaluations against diamondback moth and oriental armyworm. The bioassay results showed that some of the compounds exhibit favorable insecticidal potentials, particularly some novel piperazine-containing heterocyclic mono-/di-/tri-amide derivatives such as 8g, 14a, 15a, 15g, 15i, 15j, 15k, 15l, and 15m could be used as new insecticidal leading structures for further study (e.g., towards diamondback moth, 15i-15m LC50: 0.0022?0.0081 mg/L). The structure-activity relationships of the compounds discussed in detail provide useful guidance for further design and development of new insecticides.

Synthesis and structure-insecticidal activity relationship of novel phenylpyrazole carboxylic acid derivatives containing fluorine moiety

A series of novel phenylpyrazole carboxylic acid derivatives containing fluorine moiety, i.e., diamides 11, simple aryl-bearing amides 12 and acylthioureas 14 were successfully synthesized based on the key fluoro-containing phenylpyrazole acid intermediate. The new compounds were identified and confirmed by melting point, 1H NMR, 13C NMR and elemental analysis or HRMS. The bioassay results indicated that some of the compounds possessed excellent insecticidal activities towards oriental armyworm, diamondback moth and corn borer at low concentrations. For examples, compounds 11a, 11e?g and 14b exhibited remarkable larvicidal activities with LC50 values of 0.13 ? 0.39 mg/L and 0.0002 ? 0.0014 mg/L against oriental armyworm and diamondback moth, respectively, were comparable with those of the control chlorantraniliprole. Particularly, 11e were found superior to chlorantraniliprole in oriental armyworm tests (LC50: 0.23 mg/L vs. 0.26 mg/L); 11a, 11e, 11f and 14c in diamondback moth tests with LC50 values of 0.0002 mg/L, 0.0002 mg/L, 0.0008 mg/L and 0.0005 mg/L, respectively, were more effective than that of chlorantraniliprole. In addition, 12a also showed a promising insecticidal potential and development/optimization advantage. Compounds 11a, 11e–g, 12a, 14b and 14c could be considered as possible new leading structures for further study. The SAR investigation indicated that the compounds with fluorine motif (e.g., -F, -CF2H, -CF3) held apparently favorable insecticidal potentials, which provided useful guidance for further design/development of new phenylpyrazole-containing agrochemicals.

Synthesis, bioactivity, action mode and 3D-QSAR of novel anthranilic diamide derivatives

To study the pesticide effect, action mode, structure-activity relationships (SARs) of anthranilic diamide insecticide and screen highly active pesticides, novel anthranilic diamide derivatives were synthesized. Bioassays indicated that all of the title compounds displayed 100% mortality against diamondback moth and oriental armyworm at 100 mg/L, among which 12v and 12w showed 100% insecticidal acitvity at 5 mg/L. Surprisingly compound 12w exhibited better insecticidal acitvity than commercialized chlorantraniliprole against Pyrausta nubilalis (0.1 mg/L) and Cnaphalocrocis Medinalis (2 mg/L). 3D-QSAR and SARs statistical analysis revealed that title compounds with R2 fixed as methoxy had the highest probability possessing high activity. The calcium fluorescence measurements on neurons revealed that E series compounds containing pyrazinyl may have a molecular target different from caffeine on ryanodine receptors rather than the voltage-gated calcium channel present on cytomembran.

Acyl thiourea and acyl urea derivatives containing trifluoromethylpyridine and application thereof

The invention discloses acyl thiourea and acyl urea derivatives containing trifluoromethylpyridine and an application thereof. A structure of the derivatives is shown in a general formula I. In the formula, definitions of R1, R2, R3, X and other groups are as shown in the description. The compound represented by the general formula I has excellent insecticidal activity, and can be used to preventand treat pests such as cotton bollworm, diamondback moth and brown planthopper, and can also be used to prevent and treat plant virus diseases such as TMV and CMV.

Palladium-Catalyzed Cyclization Reaction of o-Iodoanilines, CO2, and CO: Access to Isatoic Anhydrides

Isatoic anhydrides, a class of valuable synthetic intermediates and RNA structure probing reagents, are usually prepared with highly toxic phosgene or stoichiometric oxidants. Herein we report a highly selective palladium-catalyzed cyclization reaction for the efficient synthesis of isatoic anhydrides from readily available o-iodoanilines, CO2, and CO. The reaction proceeds under mild conditions and is redox-neutral. Both CO2 and CO are indispensable C1 building blocks for this catalytic reaction.

PROCESS FOR PREPARING N-SUBSTITUTED 1H-PYRAZOLE-5-CARBONYLCHLORIDE COMPOUNDS

The present invention relates to a process for preparing an N-substi- tuted 1 H-pyrazole-5-carbonylchloride compound of the formula (I) comprising the steps of i) deprotonating a compound of the formula (II) with a base selected from lithium-organic base having a carbon or nitrogen bound lithium or with a magnesium-organic base having a carbon bound magnesium; and ii) subjecting the product obtained in step (i) to a chlorocarbonylation by reacting it with a reagent selected from the group consisting of phosgene or a phosgene equivalent, to obtain a compound of formula (I).

PROCESS FOR PREPARING N-SUBSTITUTED 1H-PYRAZOLE-5-CARBOXYLATE COMPOUNDS AND DERIVATIVES THEREOF

The present invention relates to a process for preparing an N-substituted 1 H-pyrazole- 5- carboxylate compound of the formula (l-A) comprising the steps of i) deprotonating a compound of the formula (II) in which the variables R1, R2 and r are each as defined in the description and the claims, with a magnesium-organic base having a carbon bound magnesium; and ii) subjecting the product obtained in step (i) to a carbonylation by reacting it with a reagent selected from the group consisting carbon dioxide or a carbon dioxide equivalent, to obtain a compound of formula (l-A); and it relates to further conversions to yield a N-substituted 1H-pyrazole-5-carbonyl chloride compound of the formula (I).