Clipper

Base Information

• Chemical Name: Clipper
• CAS No.: 76738-62-0
• Molecular Formula: C15H20ClN3O
• Molecular Weight: 293.79
• Hs Code.: 29339900
• European Community (EC) Number: 616-379-6,927-876-5
• Wikipedia: Paclobutrazol
• Mol file: 76738-62-0.mol

Synonyms:1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol;paclobutrazol;paclobutrazol, (R*,S*)-(+-)-isomer;paclobutrazol, (R*,S*)-isomer;paclobutrazol, (R-(R*,R*))-isomer;paclobutrazol, (R-(R*,S*))-isomer;paclobutrazol, (S-(R*,R*))-isomer;paclobutrazol, (S-(R*,S*))-isomer

Chemical Property of Clipper

Chemical Property:

• Appearance/Colour: off-white to beige solid
• Vapor Pressure: 2.72E-09mmHg at 25°C
• Melting Point: 165-166 °C
• Boiling Point: 460.9 °C at 760 mmHg
• PKA: 13.92±0.20(Predicted)
• Flash Point: 232.6 °C
• PSA: 50.94000
• Density: 1.19 g/cm3
• LogP: 3.12230
• Storage Temp.: 0-6°C
• Sensitive.: Hygroscopic
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 293.1294900
• Heavy Atom Count: 20
• Complexity: 300

Purity/Quality:

99% ^*data from raw suppliers

Paclobutrazol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,F
• Statements: 22-21/22-11
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)C(C(CC1=CC=C(C=C1)Cl)N2C=NC=N2)O
• Isomeric SMILES: CC(C)(C)C([C@H](CC1=CC=C(C=C1)Cl)N2C=NC=N2)O
• Recent EU Clinical Trials: Effect of Beclometasone dipropionate (BDP) on faecal Calprotectin levels in patients with clinically inactive Ulcerative Colitis at risk of relapse. BeCalCU study
• Uses: 1. Paclobutrazol belongs to azole plant growth regulators, being the biosynthetic inhibitors of the endogenous gibberellin. It has effects of hindering plant growth and shortening the pitch. For example, being used in rice can improve the activity of indole acetic acid oxidase, reduce the level of endogenous IAA in rice seedlings, significantly control the growth rate of the top of the rice seedlings, promote leaf, make the leaves dark green, the root system developed, reduce the lodging and increase the production amount. The general control rate is up to 30%; leaf promotion rate is 50% to 100%, and the production increase rate is 35%. Being used in peach, pear, citrus, apples and other fruit trees can be used to shorten the tree. Geranium, poinsettia and some ornamental shrubs, when treated with paclobutrazol, have their plant type be adjusted, giving higher ornamental value. Cultivation of greenhouse vegetables such as tomatoes and rape gives a strong seedling effect. 2. Cultivation of late rice can strengthen the seedling, during the one-leaf/one-heart stage, dry out the seedling water in the field and apply 100~300mg/L of PPA solution for uniform spraying in 15kg/100m2. Control the excessive growth of the machine transplanting rice seedlings. Apply 150 kg of 100 mg/L paclobutrazol solution for soaking 100kg of rice seeds for 36h. Apply germination and sowing with a 35d seedling age and controlling the seedling height not higher than 25cm. When used for the branch control and fruit protection of the fruit tree, it should be usually performed in late autumn or spring with each fruit tree subjecting to injection of 500 mL of 300mg/L paclobutrazol drug solution, or subjecting to uniform irrigation along the 5~10cm place of the soil surface around the 1/2 crown radius. Apply 15% wettability powder 98g/100m2 or so. Apply the 100 m2 paclobutrazol with an active ingredient of 1.2~1.8 g/100m2, being able to shorten the base intersection of the winter wheat and strengthen the stem. 3. Paclobutrazol also has effect against the rice blast, cotton red rot, cereal smut, wheat and the rust of other crops as well as powdery mildew, etc. It can also used for fruit preservatives. In addition, within a certain amount, it also has inhibitory effect against some single, dicotyledonous weeds. 4. Paclobutrazol is a novel plant growth regulator, being able to inhibit the formation of gibberellin derivatives, reducing the plant cell division and elongation. It can be easily absorbed by roots, stems and leaves and conducted through the xylem of the plant with bactericidal effect. It has extensive activity on the Gramineae plants, being able to make the plant stems become short stalks, reduce the lodging and increase the yield. 5. It is a novel, high efficiency, low toxicity plant growth regulator with broad-spectrum bactericidal effect. 6. Fixed consumption amount of raw materials: Pinacolone: 930kg/t, 1,2,4-triazole 540kg/t, chlorobenzyl chloride 960kg/t. Paclobutrazol is a triazole fungicide used as an plant growth retardant in inhibiting gibberellin biosynthesis. Plant growth regulator.
• Production method: Preparation method one 1,2,4-triazole and 1-chloro-3,3-dimethyl-2-butanone were used as starting materials to synthesize α-1,2,4-triazole-3,3-dimethyl-2-butanone, followed with condensation reaction with chlorobenzyl chloride, generating the α-p-chlorobenzyl-1,2,4-triazole-3,3-dimethyl-2-butanone, and then followed by being reduced by sodium borohydride to get the paclobutrazol. This method is easy to obtain raw materials with less steps less. The main drawback is that during the reduction reaction using sodium borohydride (potassium), resulting in high cost. According to the literature, the Sodium Disulfite (Na2S2O4) is used as reductant for reaction at alkaline media (NaHCO3) and the selected solvent or solvent system (water-methanol, 6: 1, volume ratio), generating paclobutrazol. An example of the operation is as follows: 0.03 mol of NaHCO3 is mixed with 60 mL of water and heated with stirring to dissolving. Then, the chlorothiazone was completely dissolved in 10 mL methanol and then added into the aqueous solution of NaHCO3 in one time. The resulting turbid reaction mixture was heated and stirred, and the safety powder (0.03 mol) was added in 6 h in 6 h after refluxing. Perform reflux for 2h. After the end of the reaction, apply cooling, suction filtration, washing with water and drying to get paclobutrazol with the melting point of 146~154 ℃. The crude product was recrystallized from acetonitrile as a white solid with a m.p. of 162-163 ° C, product purity of 98.23%, and the yield of 98.81% base on calculation on clozapine. Preparation method two Take p-chlorobenzaldehyde and 3,3-dimethyl-2-butanone as the raw material to generate the corresponding ketene, with hydrogenation, bromination and reaction with 1, 2, 4-triazole, and finally reduced with boron hydride sodium to generate paclobutrazol. This method is easy to obtain raw materials, but the process is longer. Preparation method three 1-(p-chlorophenyl)-2-(1,2,4-triazol-1-yl) propionyl chloride is reacted with tert-butyl magnesium bromide, followed by reduction with sodium borohydride to generate paclobutrazol. Though the production steps of this method are few, but the raw material is rare, and easy to subject to hydrolysis, need to be carried out under anhydrous conditions.
• Description: Paclobutrazol (PBZ) is a triazole-containing plant growth retardant that is known to inhibit the biosynthesis of gibberellins. It also has antifungal activities. PBZ, which is transported acropetally in plants, can also suppress the synthesis of abscisic acid and induce chilling tolerance in plants. PBZ is typically used to support research on the role of gibberellins in plant biology.

Technology Process of Clipper

There total 8 articles about Clipper which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1-(4-chlorobenzyloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one → paclobutrazol (66345-53-7,66346-05-2,76738-62-0,76738-64-2,82336-55-8,98169-53-0,102735-64-8,115509-55-2,66346-04-1)

Guidance literature:

With sodium borohydrid; In ethanol;

Reference yield:

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → 1-(4'-chlorophenyl)-2-bromo-4,4-dimethylpentan-3-one (66346-02-9) + paclobutrazol (66345-53-7,66346-05-2,76738-62-0,76738-64-2,82336-55-8,98169-53-0,102735-64-8,115509-55-2,66346-04-1)

Guidance literature:

With bromine; In tetrachloromethane;

Reference yield:

1-bromo-butane (109-65-9) + n-butyl magnesium bromide (693-03-8) + α-(1,2,4-triazol-1-yl)-α-p-chlorobenzylchloride (66346-00-7) → paclobutrazol (66345-53-7,66346-05-2,76738-62-0,76738-64-2,82336-55-8,98169-53-0,102735-64-8,115509-55-2,66346-04-1)

Guidance literature:

With sulfuric acid; magnesium; In diethyl ether;

upstream raw materials:

1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-one

3,3-dimethyl-butan-2-one

1-Bromopinacolon

3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone

Refernces

• 1、 -. "Patch preparations for treating plants". . . Retrieved 2008/06/13.
• 2、 -. "Use of diphenyl ether derivatives for the desiccation and abscission of plant organs". . . Retrieved 2008/06/13.