190588-40-0

Usage

Common uses

Plant growth regulator, inhibits weed growth, promotes growth of desirable crops

Mechanism of action

Disrupts hormone balance in plants, leading to stunted growth and reduced weed competition

Herbicide derivative

2,4,6-trichlorophenoxyacetic acid (2,4,6-T)

Potential concerns

Toxicity, environmental impact, limited and regulated use in some regions

Upstream product

• 643-14-1 3,4,6-trichloro-2-methyl-phenol 
• 105-39-5 chloroacetic acid ethyl ester 
• 88-06-2 2,4,6-Trichlorophenol 
• 575-89-3 2-(2,4,6-trichlorophenoxy)acetic acid 

Downstream Products

• 523999-39-5 2-(2',4',6'-trichlorophenoxymethyl)-5-mercapto-1,3,4-oxadiazole 
• 402939-37-1 2-benzyl-5-(2,4,6-trichloro-phenoxymethyl)-[1,3,4]oxadiazole 
• 402939-32-6 2-(2-nitro-phenyl)-5-(2,4,6-trichloro-phenoxymethyl)-[1,3,4]oxadiazole 
• 402939-34-8 2-[5-(2,4,6-trichloro-phenoxymethyl)-[1,3,4]oxadiazol-2-yl]-phenylamine 
• 402939-36-0 2-((E)-Styryl)-5-(2,4,6-trichloro-phenoxymethyl)-[1,3,4]oxadiazole 
• 402939-29-1 2-phenyl-5-(2,4,6-trichloro-phenoxymethyl)-[1,3,4]oxadiazole 
• 402939-30-4 2-[5-(2,4,6-trichloro-phenoxymethyl)-[1,3,4]oxadiazol-2-yl]-phenol 
• 1026147-44-3 C₁₆H₉Cl₅N₂O₃ 
• 1026147-43-2 C₁₅H₇Cl₅N₂O₂ 
• 1026147-47-6 C₂₁H₂₁Cl₃N₂O₂ 
• 1026147-49-8 C₂₂H₁₇Cl₃N₂O₃ 
• 1026147-51-2 C₂₂H₁₄Cl₅N₃O₂ 
• 1026147-48-7 C₂₃H₁₆Cl₃FN₂O₂ 
• 1026147-45-4 C₁₅H₁₀Cl₃N₃O₂ 

Relevant academic research and scientific papers

Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment

Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.

Synthesis and larvicidal activity of 1,3,4-oxadiazole derivatives containing a 3-chloropyridin-2-yl-1H-pyrazole scaffold

Abstract: A new series of 1,3,4-oxadiazole derivatives with a 3-chloropyridin-2-yl-1H-pyrazole moiety was designed, synthesized, and characterized. The results of bioassay against Helicoverpa armigera and Plutella xylostella indicated that some of the synthesized compounds showed remarkable larvicidal activity. In particular, the LC50 values of the most active compounds against P. xylostella were 46.5, 23.9, and 13.9?mg/dm3, and against Helicoverpa armigera were 88.3 and 69.5?mg/dm3, the latter being slightly better than commercial chlorpyrifos (LC50 103.77?mg/dm3). Preliminary SAR was also discussed. Graphical abstract: [Figure not available: see fulltext.].

Synthesis, Nematicidal Activity, and 3D-QSAR of Novel 1,3,4-Oxadiazole/ Thiadiazole Thioether Derivatives

Forty one novel 1,3,4-oxadiazole/thiadiazole thioether derivatives containing phenoxy moiety were designed and synthesized. Bioassay demonstrated that some of them showed remarkable activities against Tylenchulus semipenetrans in vitro and in vivo. Compounds 20, 21, 35 and 39 showed excellent lethal activities after treatment for 48?h in vitro, with LC50 values of 13.4?±?1.8, 11.7?±?2.5, 13.7?±?2.4 and 13.3?±?1.1?mg·L–1, respectively, which were obviously superior to fosthiazate (49.1?±?2.8?mg·L–1) and avermectin (26.6?±?2.3?mg·L–1). Compound 21 can effectively control the citrus nematode disease caused by T. semipenetrans at 200?mg·L–1 in vivo with (68?±?3)% inhibitory effect, which was even better than that of avermectin ((63?±?2)%). The CoMFA and CoMSIA models of three-dimensional quantitative structure-activity relationships (3D-QSARs) were established. The compound 33 was designed based on the 3D-QSAR models with more vigorous nematicidal activities in vitro (LC50?=?9.8?±?1.4?mg·L–1) and in vivo ((70?±?5)%). These results demonstrated that compound 33 can be considered as a potential nematicide.

Synthesis and Herbicidal Activity of Some Novel Pyrazole Derivatives

Some novel pyrazole derivatives were designed and synthesized through multi-step reactions from substituted phenol as starting material. Their structures were confirmed by 1H NMR, FTIR, MS and elemental analysis. All these compounds were evaluated their herbicidal activity. The preliminary bioassay results indicated that some of title compounds displayed moderate herbicidal activity at 200 μg/mL. Among them, compounds 4-chloro-N'-(2-(2,5-dimethyl-phenoxy) acetyl)-3-ethyl-1-methyl-1H-pyrazole-5-carbohydrazide, 4-chloro-N'-(2-(2,4-dichlorophenoxy)acetyl)- 3-ethyl-1-methyl-1H-pyrazole-5-carbohydrazide, 4-chloro-3-ethyl-1-methyl-N'-(2-(m-tolyloxy) acetyl)-1H-pyrazole-5-carbohydrazide and 4-chloro-3-ethyl-1-methyl-N'-(2-(3-nitrophenoxy)acetyl)- 1H-pyrazole-5-car-bohydrazide possessed 95%, 100%, 95% and 95% inhibition against Brassica campestris respectively. In the further bioassay, the compound 6l exhibited excellent herbicidal activity either monocotyledon or dicotyledon plant at 150 g/ha.

2,5-substituent-1,3,4-oxadiazole (thiadiazole) thioether derivatives as well as preparation method and application thereof

The invention discloses 2,5-substituent-1,3,4-oxadiazole (thiadiazole) thioether derivatives as well as a preparation method and an application thereof. The 2,5-substituent-1,3,4-oxadiazole (thiadiazole) thioether derivatives have the general formula (I) shown in the following specification, wherein R1 represents as 4-chlorphenyl, 4-fluorophenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-cyano-3,5-difluorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, 4-t-butylphenyl, 2-fluorophenyl and other substituents; R2 represents methyl, ethyl, 4-chlorobenzyl, 2,4-dichlorobenzyl, 4-trifluoromethoxy, benzyl, 4-fluorobenzyl, 4-chlorobenzyl and other substituents; X represents O or S. The compound can be used as a pesticide for killing crop nematode and inhibiting bacterial diseases of crops.

Design, synthesis, molecular docking and 3D-QSAR studies of potent inhibitors of enoyl-acyl carrier protein reductase as potential antimycobacterial agents

In order to develop a lead antimycobacterium tuberculosis compound, a series of 52, novel pyrrole hydrazine derivatives have been synthesized and screened which target the essential enoyl-ACP reductase. The binding mode of the compounds at the active site of enoyl-ACP reductase was explored using surflex-docking method. The binding model suggests one or two hydrogen bonding interactions between pyrrole hydrazones and InhA enzyme. Highly active compound 5r (MIC 0.2 μg/mL) showed hydrogen bonding interactions with Tyr158 and NAD+ in the same manner as those of ligands PT70 and triclosan. The CoMFA and CoMSIA models generated with database alignment were the best in terms of overall statistics. The predictive ability of the CoMFA and CoMSIA models was determined using a test set of 13 compounds, which gave predictive correlation coefficients (rpred2) of 0.896 and 0.930, respectively.

Synthesis, antibacterial and antifungal activities of 2,5-disubstituted-1, 3,4-oxadiazoles

A series of 2,5- distributed 1,3,4-oxadiazole derivatives were prepared and evaluated for their antibacterial and antifungal activities. 5-[(2, 4, 6-trichlorophenoxy) methyl]- 1,3,4-oxadiazol-2-thiol 5 was synthesized by the reaction of 2-(2,4,6,-trichlorophenoxy) acetic acid hydrazide 4 with CS 2 and KOH in ethanol. The compound 5 on reaction with ethyl chloroacetate gave ethyl-2-(5-(2,4,6-trichlorophenoxy)methyl)-1,3,4-oxadiazol- 2-ylthio) acetate 6 and this on further hydrolysis by sodium hydroxide, followed by acidification gave 2-(5-((2,4,6-trichlorophenoxy)methyl)-1l3,4-oxadiazol-2- ylthio) acetic acid. 7.The compound 5 on condensation with p-benzoquinone in dry acetone gave 2- (5-((2,4l6-trichlorophenoxy)methyl)-1,3l4-oxadiazol-2-ylthio) benzene-1,4-diol 8.1,3,4- Oxadiazole derivatives 9-15 were prepared by treating hydrazide 4 with aromatic acids, in presence of dehydrating agent. Structures of the newly synthesized compounds were confirmed on the basis of physico-chemical and spectral data. All the synthesized compounds were screened for their antibacterial and antifungal activities using broth micro dilution method. Compounds have shown moderate to good antibacterial and antifungal activities.

Synthesis and antimicrobial activity of 1,2,4-triazoles

3-(2′,4′,6′-Trichlorophenoxymethyl)-4-(4″ -methoxyphenyl)-5-aryl-1,2,4-triazoles (4a-j) and 3-(2′,4′,6′ -trichlorophenoxymethyl)-4-(N-benzylidenylamino)-5-mercapto-1,2,4-triazoles (7a-j) have been synthesized, and their antimicrobial activities studied.