25755-85-5

Usage

Physical appearance

white to off-white crystalline powder

Common use

pesticide or herbicide

Mode of action

inhibits plant growth by disrupting protein synthesis

Regulatory status

heavily regulated due to toxicity and environmental impact

Upstream product

• 124-38-9 carbon dioxide 
• 1956-39-4 4-chloroacetophenone oxime 
• 2881-63-2 ethyl (4-chlorobenzoyl)acetate 
• 22027-53-8 methyl 3-(4-chlorophenyl)-3-oxopropanoate 
• 99-91-2 para-chloroacetophenone 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 69498-30-2 5-chloro-2-(4-chlorophenyl)-1H-benzo[d]imidazole 
• 139436-66-1 6-chloro-2-(4-chlorophenyl)quinoxaline 
• 2818-69-1 5-chloro-2-methyl-1H-benzimidazole 
• 142335-35-1 7-Chloro-4-(4-chloro-phenyl)-1,3-dihydro-benzo[b][1,4]diazepin-2-one 
• 51726-07-9 3-(4-chlorophenyl)-5-chloroisoxazole 
• 132427-15-7 5-Bromodifluoromethoxy-3-(4-chlorophenyl)isoxazole 
• 132427-14-6 3-(4-Chlorophenyl)-5-difluoromethoxyisoxazole 
• 1188228-71-8 C₁₀H₅Cl₂NO₂ 
• 1373407-46-5 C₁₀H₄Cl₃NO 
• 1373407-54-5 C₁₆H₁₂ClN₃O 
• 1373407-50-1 C₁₆H₉Cl₂N₃O 
• 1373407-58-9 C₂₄H₂₀Cl₂N₆O₂ 
• 1019-85-8 2-(4-chlorophenyl)benzimidazole 
• 17286-63-4 2-(4-chlorophenyl)quinoxaline 

Relevant academic research and scientific papers

Construction of isoxazolone-fused phenanthridinesviaRh-catalyzed cascade C-H activation/cyclization of 3-arylisoxazolones with cyclic 2-diazo-1,3-diketones

A Rh(iii)-catalyzed cascade C-H activation/intramolecular cyclization of 3-aryl-5-isoxazolones with cyclic 2-diazo-1,3-diketones was described, leading to the formation of isoxazolo[2,3-f]phenanthridine skeletons. The protocol features the simultaneous one-pot formation of two new C-C/C-N bonds and one heterocycle in moderate-to-good yields with good functional group compatibility. It is amenable to large-scale synthesis and further transformation.

Palladium catalyzed insertion reaction of isocyanides with 3-arylisoxazol-5(4 H)-ones: Synthesis of 4-aminomethylidene isoxazolone derivates

A palladium catalyzed insert reaction of isocyanides to 3-arylisoxazol-5(4H)-ones for the construction of 4-aminomethylidene isoxazolone derivates is reported. In this transformation, only the C-H bond of the methylene group was involved while the remaining ring structure was retained. In general, this work provided a new protocol for the synthesis of 4-aminomethylidene isoxazolones.

Atom-Economic Silver-Catalyzed Difunctionalization of the Isocyano Group with Cyclic Oximes: Towards Pyrimidinediones

An unprecedented silver-catalyzed difunctionalization of the isocyano group with cyclic oximes is described. This method allows efficient and atom-economic assembly of a vast array of structurally novel and interesting pyrimidinediones, and tolerates a range of functionalities. The resulting products can be easily converted into some useful compounds. Furthermore, the method can also be applied for the late-stage modification of a few biologically active molecules.

Stereoselective Michael Halogenation Initiated Ring Closure (MHIRC) Synthesis of Spirocyclopropanes from Benzylidenemalononitriles and 3-Arylisoxazol-5(4H)-ones

The new chemical cascade reaction was found: the direct formation of substituted 4-oxo-2,7-diaryl-5-oxa-6-azaspiro[2.4]hept-6-ene-1,1-dicarbonitriles from benzylidenemalononitriles and 3-aryl-2-isoxazol-5(4H)-ones. The action of bromine on the equimolar mixture of benzylidenemalononitrile and 3-aryl-2-isoxazol-5(4H)-one in the basic alcohol solution results in stereoselective formation of spirobicycle containing the 2-isoxazolin-5-one and the cyclopropane fragments in 53-92% yields. Thus, the new simple and efficient ‘one-pot’ approach to substituted (2R*,3R*)-4-oxo-2,7-diaryl-5-oxa-6-azaspiro[2.4]hept-6-ene-1,1-dicarbonitriles was found directly from simple and reasonable starting compounds as benzylidenemalonitriles and 3-aryl-2-isoxazol-5(4H)-ones.

Base initiated aromatization/CO bond formation: A new entry to O-pyrazole polyfluoroarylated ethers

A base initiated intermolecular SNAr reaction of pyrazolones with polyfluoroarenes was developed. The process involved the isomerization aromatization of pyrazolone followed by the CO bond formation via the selective CF bond cleavage. With this strategy, a wide range of O-pyrazole polyfluoroarylated ethers bearing diverse functional groups were synthesized in mild to good yields. Additionally, our method was also applied to the isoxazol substrates.

Synthesis of novel isoxazole fused heterocycles

Condensation of 3-aryl-4-formyl isoxazoles with 1,2-diamines led to the formation of 3-aryl-(6,7-benzo-1,5-heptadiazino)(3,2-d)-isoxazoles or isoxazolo-[5,4-b]-benzodiazepines and 3,10-diaryl-6,7,14,15-tetrhydro-13 H,16H-diisoxazole-(4,5-b;4,5-l)(1,4,8,11)-tetra-aza-cyclo-tetra-deca-4, 14-diones, the novel seven-and 14-membered heterocyclic systems. Similar compounds are of great importance in medicinal chemistry.

Discovery of a nonpeptidic small molecule antagonist of the human platelet thrombin receptor (PAR-1)

The synthesis and biological evaluation of a series of nonpeptidic small molecule antagonists of the human platelet thrombin receptor (PAR-1) are described. Optimization of the 5-amino-3-arylisoxazole lead resulted in an approximate 100-fold increase in potency. The most potent of these compounds (54) inhibits platelet activation with IC50s of 90 nM against the thrombin receptor agonist peptide (TRAP) and 510 nM against thrombin as the agonist. Further, antagonist 54 fully blocks platelet aggregation stimulated by 1 nM thrombin for 10 min.

High-temperature rearrangements of 2-acylisoxazol-5(2H)-ones and related oxazoles

2-Acyl-3-arylisoxazol-5(2H)-ones give 2-alkyl(aryl)-4-aryloxazoles in good yields at 540°C under flash vacuum pyrolysis conditions, but at higher temperatures the expected oxazoles are accompanied by increasing amounts of isomeric 2,5-disubstituted oxazoles, as well as anilides and decomposition products of the 2,4-disubstituted oxazole. The rearrangement mechanisms have been studied by the use of 13C labelled substrates and p-substituted 3-arylisoxazolones. The 2,5-disubstituted oxazoles are considered to arise from 1H-azirines, and the anilides from the nitrone ketene isomer of the acylisoxazolone.

Synthesis of 1H-1,5-benzodiazepin-2(3H)-ones from 5(4H)-isoxazolone, a heterocyclic bifunctional C-3 synthon

Unsubstituted and 7- or 8-substituted 4-aryl-1H-1,5-benzodiazepin-2(3H)-ones 3a-t have been synthesized by the condensation of 3-aryl-5(4H)-isoxazolones 1a-e and parent 4-substituted 1,2-benzenediamines 2a-d under acidic conditions.