Paclobutrazol
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| Category | Others |
| Catalog number | BBF-04091 |
| CAS | 76738-62-0 |
| Molecular Weight | 293.79 |
| Molecular Formula | C15H20ClN3O |
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Description
Paclobutrazol is a triazole antifungal drug that inhibits the growth of plants by preventing the biosynthesis of gibberellin (a plant hormone).
Specification
| Synonyms | (2R,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol |
| Shelf Life | Limited shelf life, expiry date on the label |
| Storage | Store at 2-8°C |
| IUPAC Name | (2R,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol |
| Canonical SMILES | CC(C)(C)C(C(CC1=CC=C(C=C1)Cl)N2C=NC=N2)O |
| InChI | InChI=1S/C15H20ClN3O/c1-15(2,3)14(20)13(19-10-17-9-18-19)8-11-4-6-12(16)7-5-11/h4-7,9-10,13-14,20H,8H2,1-3H3/t13-,14+/m1/s1 |
| InChI Key | RMOGWMIKYWRTKW-KGLIPLIRSA-N |
Properties
| Appearance | Off-white to beige Solid |
| Application | Pesticide |
| Boiling Point | 460.9°C at 760 mmHg |
| Melting Point | 165-166°C |
| Density | 1.19 g/cm3 |
| Solubility | Soluble in ethanol, DMF, DMSO |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
Reference Reading
1.Breadfruit (Artocarpus altilis) gibberellin 2-oxidase genes in stem elongation and abiotic stress response.
Zhou Y1, Underhill SJ2. Plant Physiol Biochem. 2016 Jan;98:81-8. doi: 10.1016/j.plaphy.2015.11.012. Epub 2015 Nov 23.
Breadfruit (Artocarpus altilis) is a traditional staple tree crop in the Oceania. Susceptibility to windstorm damage is a primary constraint on breadfruit cultivation. Significant tree loss due to intense tropical windstorm in the past decades has driven a widespread interest in developing breadfruit with dwarf stature. Gibberellin (GA) is one of the most important determinants of plant height. GA 2-oxidase is a key enzyme regulating the flux of GA through deactivating biologically active GAs in plants. As a first step toward understanding the molecular mechanism of growth regulation in the species, we isolated a cohort of four full-length GA2-oxidase cDNAs, AaGA2ox1- AaGA2ox4 from breadfruit. Sequence analysis indicated the deduced proteins encoded by these AaGA2oxs clustered together under the C19 GA2ox group. Transcripts of AaGA2ox1, AaGA2ox2 and AaGA2ox3 were detected in all plant organs, but exhibited highest level in source leaves and stems.
2.Xyloglucan Metabolism Differentially Impacts the Cell Wall Characteristics of the Endosperm and Embryo during Arabidopsis Seed Germination.
Sechet J1, Frey A1, Effroy-Cuzzi D1, Berger A1, Perreau F1, Cueff G1, Charif D1, Rajjou L1, Mouille G1, North HM1, Marion-Poll A2. Plant Physiol. 2016 Mar;170(3):1367-80. doi: 10.1104/pp.15.01312. Epub 2016 Jan 29.
Cell wall remodeling is an essential mechanism for the regulation of plant growth and architecture, and xyloglucans (XyGs), the major hemicellulose, are often considered as spacers of cellulose microfibrils during growth. In the seed, the activity of cell wall enzymes plays a critical role in germination by enabling embryo cell expansion leading to radicle protrusion, as well as endosperm weakening prior to its rupture. A screen for Arabidopsis (Arabidopsis thaliana) mutants affected in the hormonal control of germination identified a mutant, xyl1, able to germinate on paclobutrazol, an inhibitor of gibberellin biosynthesis. This mutant also exhibited reduced dormancy and increased resistance to high temperature. The XYL1 locus encodes an α-xylosidase required for XyG maturation through the trimming of Xyl. The xyl1 mutant phenotypes were associated with modifications to endosperm cell wall composition that likely impact on its resistance, as further demonstrated by the restoration of normal germination characteristics by endosperm-specific XYL1 expression.
3.OsWOX3A is involved in negative feedback regulation of the gibberellic acid biosynthetic pathway in rice (Oryza sativa).
Cho SH1, Kang K2, Lee SH2, Lee IJ3, Paek NC2. J Exp Bot. 2016 Apr;67(6):1677-87. doi: 10.1093/jxb/erv559. Epub 2016 Jan 14.
The plant-specific WUSCHEL-related homeobox (WOX) nuclear proteins have important roles in the transcriptional regulation of many developmental processes. Among the rice (Oryza sativa) WOX proteins, a loss of OsWOX3A function in narrow leaf2 (nal2) nal3 double mutants (termed nal2/3) causes pleiotropic effects, such as narrow and curly leaves, opened spikelets, narrow grains, more tillers, and fewer lateral roots, but almost normal plant height. To examine OsWOX3A function in more detail, transgenic rice overexpressing OsWOX3A (OsWOX3A-OX) were generated; unexpectedly, all of them consistently exhibited severe dwarfism with very short and wide leaves, a phenotype that resembles that of gibberellic acid (GA)-deficient or GA-insensitive mutants. Exogenous GA3 treatment fully rescued the developmental defects of OsWOX3A-OX plants, suggesting that constitutive overexpression of OsWOX3A downregulates GA biosynthesis. Quantitative analysis of GA intermediates revealed significantly reduced levels of GA20 and bioactive GA1 in OsWOX3A-OX, possibly due to downregulation of the expression of KAO, which encodes ent-kaurenoic acid oxidase, a GA biosynthetic enzyme.
4.The Mechanism of Ethylene Signaling Induced by Endophytic Fungus Gilmaniella sp. AL12 Mediating Sesquiterpenoids Biosynthesis in Atractylodes lancea.
Yuan J1, Sun K1, Deng-Wang MY1, Dai CC1. Front Plant Sci. 2016 Mar 23;7:361. doi: 10.3389/fpls.2016.00361. eCollection 2016.
Ethylene, the first known gaseous phytohormone, is involved in plant growth, development as well as responses to environmental signals. However, limited information is available on the role of ethylene in endophytic fungi induced secondary metabolites biosynthesis. Atractylodes lancea is a traditional Chinese herb, and its quality depends on the main active compounds sesquiterpenoids. This work showed that the endophytic fungus Gilmaniella sp. AL12 induced ethylene production in Atractylodes lancea. Pre-treatment of plantlets with ethylene inhibiter aminooxyacetic acid (AOA) suppressed endophytic fungi induced accumulation of ethylene and sesquiterpenoids. Plantlets were further treated with AOA, salicylic acid (SA) biosynthesis inhibitor paclobutrazol (PAC), jasmonic acid inhibitor ibuprofen (IBU), hydrogen peroxide (H2O2) scavenger catalase (CAT), nitric oxide (NO)-specific scavenger 2-(4-Carboxyphenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide potassium salt (cPTIO).
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C15H20ClN3O
Molecular Weight (Monoisotopic Mass): 293.1295 Da
Molecular Weight (Avergae Mass): 293.792 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C15H20ClN3O
Molecular Weight (Monoisotopic Mass): 293.1295 Da
Molecular Weight (Avergae Mass): 293.792 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
