22631-59-0

Usage

Uses

Used in Agricultural Industry:
3,5-DCMB is used as a herbicide for weed control in various agricultural crops and turf. It functions by inhibiting the enzyme p-hydroxyphenylpyruvate dioxygenase (HPPD), which plays a crucial role in the synthesis of carotenoid pigments in plants. The disruption of this enzyme activity results in a deficiency of carotenoids, leading to chlorosis and ultimately, the death of the plant. This makes 3,5-DCMB an effective tool for managing unwanted plant growth in farming and landscaping.
Additionally, 3,5-DCMB is used as a plant growth regulator, potentially influencing the growth patterns and characteristics of certain plants. This dual functionality underscores its value in agricultural practices where both weed eradication and crop management are essential.

InChI:InChI=1/C8H8Cl2N2O2/c1-14-7-5(9)2-4(3-6(7)10)8(13)12-11/h2-3H,11H2,1H3,(H,12,13)

Upstream product

• 15945-28-5 ethyl 3,5-dichloro-4-methoxybenzoate 
• 17302-82-8 ethyl 3,5-dichloro-4-hydroxybenzoate 

Downstream Products

• 1422570-68-0 3-(5-(3,5-dichloro-4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)benzene-1-sulfonyl fluoride 
• 1422570-74-8 4-chloro-3-(5-(3,5-dichloro-4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)benzene-1-sulfonyl fluoride 
• 1422570-77-1 3-(5-(3,5-dichloro-4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-4-iodobenzene-1-sulfonyl fluoride 
• 1422570-80-6 4-bromo-3-(5-(3,5-dichloro-4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)benzene-1-sulfonyl fluoride 
• 1439388-14-3 C₁₆H₁₁Cl₂FN₂O₄S 
• 1422569-98-9 3-(5-(3,5-dichloro-4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)benzene-1-sulfonyl fluoride 
• 1422570-26-0 4-chloro-3-(5-(3,5-dichloro-4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)benzene-1-sulfonyl fluoride 
• 1422570-28-2 4-bromo-3-(5-(3,5-dichloro-4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)benzene-1-sulfonyl fluoride 
• 1422570-31-7 3-(5-(3,5-dichloro-4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)-4-iodobenzene-1-sulfonyl fluoride 
• 1422570-34-0 3-(5-(3,5-dichloro-4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)-4-methylbenzene-1-sulfonyl fluoride 

Relevant academic research and scientific papers

Aromatic sulfonyl fluorides covalently kinetically stabilize transthyretin to prevent amyloidogenesis while affording a fluorescent conjugate

Molecules that bind selectively to a given protein and then undergo a rapid chemoselective reaction to form a covalent conjugate have utility in drug development. Herein a library of 1,3,4-oxadiazoles substituted at the 2 position with an aryl sulfonyl fluoride and at the 5 position with a substituted aryl known to have high affinity for the inner thyroxine binding subsite of transthyretin (TTR) was conceived of by structure-based design principles and was chemically synthesized. When bound in the thyroxine binding site, most of the aryl sulfonyl fluorides react rapidly and chemoselectively with the pK a-perturbed K15 residue, kinetically stabilizing TTR and thus preventing amyloid fibril formation, known to cause polyneuropathy. Conjugation t50s range from 1 to 4 min, ～1400 times faster than the hydrolysis reaction outside the thyroxine binding site. X-ray crystallography confirms the anticipated binding orientation and sheds light on the sulfonyl fluoride activation leading to the sulfonamide linkage to TTR. A few of the aryl sulfonyl fluorides efficiently form conjugates with TTR in plasma. Eleven of the TTR covalent kinetic stabilizers synthesized exhibit fluorescence upon conjugation and therefore could have imaging applications as a consequence of the environment sensitive fluorescence of the chromophore.