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Indole-3-Butyric Acid

HCID 8617
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Basic information

CAS
133-32-4
Standard SMILES
O=C(O)CCCc1c[nH]c2ccccc12
InChIKey
JTEDVYBZBROSJT-UHFFFAOYSA-N
Molecular formula
C12H13NO2
Average molar mass
203.24 g/mol
Monoisotopic mass
203.09462866

Overview

Indole-3-butyric acid is a indol-3-yl carboxylic acid that is butanoic acid carrying a 1H-indol-3-yl substituent at position 1. It has a role as an auxin, a plant hormone and a plant metabolite. It is functionally related to a butyric acid. It is a conjugate acid of an indole-3-butyrate.

Names & identifiers

Preferred name
Indole-3-Butyric Acid
IUPAC
4-(1H-indol-3-yl)butanoic acid
English name
Indole-3-butyric acid
Molecular formula
C12H13NO2
Molecular weight
203.24

Names & synonyms

Indole-3-butyric acid3-Indolebutyric acid133-32-44-(1H-Indol-3-yl)butanoic acidIndolebutyric acidHormodinSeradix1H-INDOLE-3-BUTANOIC ACID4-(3-Indolyl)butyric acidJiffy grow4-indol-3-ylbutyric acidIndole-3-butanoic acid
Show more names
IBAhormexrootingpowder3-Indolybutyric acidIndole-3-butyric acid IBA4-indole-3-ylbutyric acid
Indolbutyric acidSeradix 2Seradix 3Seradix B 2Seradix B 3Rhizopon AAIndole butyric acid3-Indolyl-gamma-butyric acid

Database identifiers

CAS
133-32-4
PubChem CID
8617
DTXSID
DTXSID8032623
ChEMBL
CHEMBL582878
ChEBI
CHEBI:33070
UNII
061SKE27JP
EC Number
205-101-5
Nikkaji
J2.525I

Properties

Computed structural properties

XLogP
2.3
Topological polar surface area
53.1 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
4
Heavy atoms
15
Formal charge
0
Complexity
230

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Pesticides · 4 items

Plant Growth Regulators

Active substance -> EU Pesticides database: Approved

Pesticides -> Plant Growth Regulators

Herbicides

LogP · 3 items

log Kow = 2.30

2.30

2.3

OdorEssentially odorless
Color/Form · 2 items

White to slightly yellow crystals

White to tan powder or crystalline solid

Solubility · 3 items

In benzene: >1000 g/L; in acetone, ethanol, diethyl ether: 30-100 g/L; in chloroform: 0.01-1 g/L

In water, 250 mg/L @ 20 °C

0.25 mg/mL at 20 °C

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point · 2 items

124.5 °C

124.5 °C

Vapor Pressure

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H301 (98%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 98 reports by companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

Hazard information

Regulatory Information · 3 items

Commission Regulation (EC) No 2229/2004

2008/941/EC, 2011/28/EU, Reg. (EU) 2023/918, Reg. (EU) 2025/2316, Reg.(EU) No 2018/1266, Reg.(EU) No 540/2011

Indolylbutyric acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 1H-Indole-3-butanoic acid: Environment tier I assessment
Fire PotentialNon-flammable
Hazards SummaryAll generic toxicology data requirements waived because of low toxicity; Causes substantial but temporary eye injury. [Reference #1] An irritant; [MSDSonline] See Indoleacetic acid.
Special Reports · 1 item

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Indole-3-Butyric Acid, August 1992. The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of February 10, 2004: http://www.epa.gov/pesticides/reregistration/status.htm]

Chemistry & industry

Pharmacology

Tissue LocationsNeuron
Cellular LocationsMembrane

Uses & manufacturing

Uses · 5 items

Used to stimulate root formation of plant clippings; [HSDB] Similar in structure to the naturally occurring plant-growth hormone indole-3-acetic acid; Used on fruit, vegetable, and field crops and on ornamental turf; Used to reduce transplant shock in ornamental nursery stock; [Reference #1]

Farming (Pesticides) [Category: Industry]

For indole-3-butyric acid (USEPA/OPP Pesticide Code: 046701) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Biochemical pesticide, plant growth regulator.

To stimulate root formation of plant clippings.

Methods of Manufacturing... Heating indole, gamma-butyrolactone, and sodium hydroxide , followed by acidification of the product
Formulations/Preparations · 5 items

Trade names: Hormodin, Seradix

Technical grade: 97.0%. Dust: 0.01%-4.5%; soluble concentrate/liquid: 0.0004%-1.03%; wettable powder/dust: 0.1%-0.8%.

Mixtures: Boll-Set (+gibberellic acid), Cytoplex HMS (+gibberellic acid+kinetin), Early Harvest (+cytokinins+gibberellic acid), Maxon II (+gibberellic acid), PGR-IV (+gibberellic acid), Super Lagniappe (+cytokinins+gibberellic acid).

Trade names: Synergol, Chryzoplus, Chryzopon, Chryzosan, Chryzotek, Chryzotop, Rhizopon AA.

Discontinued names: Rootone.

Household ProductsInformation on 5 consumer products that contain 3-Indolebutyric acid in the following categories is provided:
Use ClassificationHerbicides

Related reactions

33 records
New reaction record
HRID 883 reaction equation
HRID 883As reactantuspto-grants-1998_03
HRID 53563 reaction equation
HRID 53563As reactantuspto-grants-1997_04
HRID 96237 reaction equation
HRID 96237As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 121031 reaction equation
HRID 121031As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 121690 reaction equation
HRID 121690As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 128816 reaction equation
HRID 128816As reactantuspto-grants-1995_11
HRID 128817 reaction equation
HRID 128817As reactantuspto-grants-1995_11
HRID 140031 reaction equation
HRID 140031As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Page 1 of 5

Compound notes

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· 3 items

0.00000117 [mmHg]

Vapor pressure: <0.01 mPa (<8X10-8 mm Hg) @ 25 °C

1.8X10-6 mm Hg @ 25 °C /Estimated/

Henry's Law ConstantHenry's Law constant: 1.3X10-11 atm cu m/mol@ 25 °C /Estimated/
Physical Description · 2 items

White or slightly yellow solid; [Merck Index] Off-white powder; [MSDSonline]

Solid

Stability/Shelf LifeVery stable in neutral, acidic and alkaline media.

Physicochemical properties

Melting point
124 · 124-125.5 °C(lit.)
Boiling point
341.55 °C · 341.55°C (rough estimate)
Density
1.1255 · 1.1255 (rough estimate)
bulk density
360 kg/m3 · 360kg/m3
refractive index
1.544 · 1.5440 (estimate)
storage temp.
2 · 2-8°C
solubility
25 mg/mL; · DMF: 25 mg/mL; DMSO: 25 mg/mL; Ethanol: 25 mg/mL; PBS (pH 7.2): 0.1 mg/mL
form
Liquid
pka
4.83 · 4.83±0.10(Predicted)
color
Clear colorless to pale yellow
Water Solubility
Soluble in water(0.25g/L).
Sensitive
Air Sensitive
Merck
14 · 14,4965
BRN
171120 · 171120
Stability
Stable. Incompatible with strong oxidizing agents. Light sensitive.
InChI
1S/C12H13NO2/c14-12(15)7-3-4-9-8-13-11-6-2-1-5-10(9)11/h1-2,5-6,8,13H,3-4,7H2,(H,14,15)
InChIKey
JTEDVYBZBROSJT-UHFFFAOYSA-N
SMILES
OC(=O)CCCc1c[nH]c2ccccc12
LogP
2.3 · 2.300
CAS DataBase Reference
133 · 133-32-4(CAS DataBase Reference)
FDA UNII
61 SKE27JP · 061SKE27JP
EPA Substance Registry System
-3 · Indole-3-butyric acid (133-32-4)
Pesticides Freedom of Information Act (FOIA)
-3 · Indole-3-butyric acid
UNSPSC Code
12352106 · 12352106
NACRES
77 · NA.77
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
301 · H301
Precautionary statements
264 · P264-P270-P301+P310-P405-P501
PPE
2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes
T,Xi
Risk Statements
25 · 25-36/37/38
Safety Statements
26 · 26-36-45-38-36/37/39-28A
RIDADR
2811 · UN 2811 6.1/PG 3
WGK Germany
3 · 3
RTECS
5250000 · NL5250000
F
8 · 8-10-23
Hazard Note
Irritant
TSCA
TSCA listed
HazardClass
6.1 · 6.1
PackingGroup
III
HS Code
29339990 · 29339990
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
3 Oral · Acute Tox. 3 Oral
Hazardous Substances Data
133 · 133-32-4(Hazardous Substances Data)
Toxicity
50 i.p · LD50 i.p. in mice: 100 mg/kg (Anderson)
Limited Quantities
5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
FIFRA Requirements · 3 items

An exemption from the requirement of a tolerance is established for residues of auxins (specifically: indole-3-acetic acid and indole-3-butyric acid) in or on all food commodities when used as plant regulators on plants, seeds, or cuttings and on all food commodities after harvest in accordance with good agricultural practices.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Indole-3-butyric acid is on List B. Case No: 2330; Pesticide type: fungicide, herbicide; Case Status: RED Approved 09/1992; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): indole-3-butyric acid; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI..

The Agency ... finds that products containing only IBA as an active ingredient are eligible for reregistration once the product specific data, confirmatory ecotoxicity data, and amended labeling are received and accepted by the Agency. Products that contain additional active ingredients will be reregistered once the Agency completes eligibility decisions on the other active ingredients and once product specific and amended labeling are received and accepted.

Hazard Classes and Categories · 2 items

Acute Tox. 3 (98%)

Acute toxicity (Oral) - Category 3

Safety & protection

Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Allowable Tolerances · 1 item

An exemption from the requirement of a tolerance is established for residues of auxins (specifically: indole-3-acetic acid and indole-3-butyric acid) in or on all food commodities when used as plant regulators on plants, seeds, or cuttings and on all food commodities after harvest in accordance with good agricultural practices.

Toxicology

Ecotoxicity Values · 5 items

LC50 Oncorhynchus mykiss (Rainbow trout,donaldson trout) >90.5 ppm/96 hr; static /formulated product/

EC50 Daphnia magna (Water flea; intoxication, immobilization) 57 ppm/48 hr (95% confidence interval: 46-74 ppm); static /formulated product/

LC50 Colinus virginianus (Northern bobwhite, 14 day old) diet >5,000 ppm (in the diet)/8 days

LC50 Colinus virginianus (Northern bobwhite, 20 wk old) oral >2,150 mg/kg/14 days

EC50 Lactuca sativa (Lettuce; inhibition of germination) 0.06 mol/cu m/72 hr

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 550(SRC), determined from a structure estimation method(2), indicates that indolebutyric acid is expected to have moderate to low mobility in soil(SRC). The estimated pKa of indolebutyric acid is 4.7 for the ionization of the carboxylic acid group(3), indicating that this compound will primarily exist in the dissociated form in the environment; anions generally do not adsorb to organic carbon and clay as strongly as their neutral counterparts(4). Volatilization of indolebutyric acid from moist soil surfaces is not expected to be an important fate process, since indolebutyric acid is expected to exist primarily in its dissociated form in the environment(SRC). Volatilization of the undissociated form of indolebutyric acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(7). Indolebutyric acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-6 mm Hg(SRC), determined from a fragment constant method(5). Indolebutyric acid was reported to degrade rapidly in soil(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 550(SRC), determined from a structure estimation method(2), indicates that indolebutyric acid is not expected to adsorb to suspended solids and sediment(SRC). This compound is expected to exist in the dissociated form in the environment, based on an estimated pKa of 4.7 for the ionization of the carboxylic acid group(3), and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). Volatilization from water surfaces is not expected for the undissociated form of indolebutyric acid(9) based upon an estimated Henry's Law constant of 1.3X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(10). Indolebutyric acid is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(4). Indolebutyric acid was reported to be very stable in neutral, acidic, or alkaline media(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow of 2.30(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data for indolebutyric acid in water were not found; however, indolebutyric acid was reported to degrade rapidly in soil(11).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), indolebutyric acid, which has an estimated vapor pressure of 1.8X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase indolebutyric acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 hours(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase indolebutyric acid may be removed from the air by wet and dry deposition(SRC). Indolebutyric acid may be susceptible to direct photolysis by sunlight(SRC), since it has an absorbance at 290 nm(4).

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for indolebutyric acid can be estimated to be 550(SRC). According to a classification scheme(2), this estimated Koc value suggests that indolebutyric acid is expected to have low mobility in soil. The estimated pKa of indolebutyric acid is 4.7 for the carboxylic acid group(3), indicating that this compound will primarily exist in the dissociated form in the environment; anions generally do not adsorb to organic carbon and clay as strongly as their neutral counterparts(4).

Artificial Pollution Sources · 1 item

Indolebutyric acid's production may result in its release to the environment through various waste streams; its use as a rooting hormone for plant cuttings and plant growth regulator(1,2) will result in its direct release to the environment(SRC).

Environmental BiodegradationIndolebutyric acid was reported to degrade rapidly in soil(1).
Environmental Bioconcentration · 1 item

An estimated BCF of 3 was calculated for indolebutyric acid(SRC), using a log Kow of 2.30(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 item

This compound is expected to exist in the dissociated form in the environment, based on an estimated pKa of 4.7(1), and therefore volatilization from water surfaces or moist soil surfaces is not expected to be an important fate process(SRC). Indolebutyric acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-6 mm Hg(SRC), determined from a fragment constant method(2).

Non-Human Toxicity Excerpts · 3 items

/LABORATORY ANIMALS: Acute Exposure/ ...These products have low acute toxicity as suggested from data of at least one formulated product (Toxicity Categories III and IV), no dermal irritation , and moderate eye irritation, perhaps from another active or an inert ingredient in the product formulation. /Formulated Indole-3-butyric acid/

/GENOTOXICITY/ ...Indole-3-butyric acid (IBA), was tested for genetic activity in Aspergillus nidulans in a plate test. IBA was found to greatly increase somatic segregation in the fungus. ... It was found that increasing concentrations of IBA increased mitotic segregation of the fungus with most of the segregants being produced by mitotic crossing-over, together with non-disjunctional segregants at a lower level. The metabolic activation technique was also used and it was shown that when S9 mixture was added to IBA a further 3- to 5-fold increase in the number of segregants was obtained.

/GENOTOXICITY/ The plant growth-regulating hormones indole-3-acetic acid (IAA) and indole-3-butyric acid (IBA), both strong recombinogens in Aspergillus nidulans, were tested in Salmonella typhimurium strains for his revertants at a range of concentrations from 1 to 2000 micrograms/plate with and without metabolic activation and were found negative.

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of indolebutyric acid with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Indolebutyric acid is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). Indolebutyric acid was reported to be very stable in neutral, acidic, or alkaline media(3). Indolebutyric acid may be susceptible to direct photolysis by sunlight(SRC), since it has an absorbance at 290 nm(4).

Probable Routes of Human Exposure · 1 item

NIOSH (NOES Survey 1981-1983) has statistically estimated that 864 workers are potentially exposed to indolebutyric acid in the US(1). Occupational exposure to indolebutyric acid may occur through inhalation and dermal contact with this compound at workplaces where indolebutyric acid is produced or used(SRC). The general population may be exposed to indolebutyric acid via dermal contact with consumer products containing indolebutyric acid(SRC).

Environmental Fate/Exposure Summary · 1 item

Indolebutyric acid's production may result in its release to the environment through various waste streams; its use as a rooting hormone for plant cuttings and plant growth regulator will result in its direct release to the environment. If released to air, an estimated vapor pressure of 1.8X10-6 mm Hg at 25 °C indicates indolebutyric acid will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase indolebutyric acid will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 2 hours. Particulate-phase indolebutyric acid will be removed from the atmosphere by wet and dry deposition. Indolebutyric acid may be susceptible to direct photolysis by sunlight, since it has an absorbance at 290 nm. If released to soil, indolebutyric acid is expected to have moderate to low mobility based upon an estimated Koc of 550. The estimated pKa of indolebutyric acid is 4.7 for the ionization of the carboxylic acid group, indicating that this compound will primarily exist in the dissociated form in the environment and anions generally do not adsorb to organic carbon and clay as strongly as their neutral counterparts. Volatilization from moist soil surfaces is not expected to be an important fate process for indolebutyric acid, since it is expected to exist primarily in its dissociated form in the environment. Volatilization from moist soil surfaces is not expected for the undissociated form of indolebutyric acid based on an estimated Henry's Law constant of 1.3X10-11 atm cu m/mol. Volatilization from dry soil is not expected based upon indolebutyric acid's estimated vapor pressure. Indolebutyric acid was reported to degrade rapidly in soil. If released into water, indolebutyric acid is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. This compound is expected to exist in the dissociated form in the environment and therefore volatilization from water surfaces is not expected to be an important fate process. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Indolebutyric acid was reported to be very stable in neutral, acidic, or alkaline media. Occupational exposure to indolebutyric acid may occur through inhalation and dermal contact with this compound at workplaces where indolebutyric acid is produced or used. The general population may be exposed to indolebutyric acid via dermal contact with consumer products containing indolebutyric acid. (SRC)

Antidote and Emergency Treatment · 2 items

/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

Regulatory information

FIFRA Requirements · 3 items

An exemption from the requirement of a tolerance is established for residues of auxins (specifically: indole-3-acetic acid and indole-3-butyric acid) in or on all food commodities when used as plant regulators on plants, seeds, or cuttings and on all food commodities after harvest in accordance with good agricultural practices.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Indole-3-butyric acid is on List B. Case No: 2330; Pesticide type: fungicide, herbicide; Case Status: RED Approved 09/1992; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): indole-3-butyric acid; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI..

The Agency ... finds that products containing only IBA as an active ingredient are eligible for reregistration once the product specific data, confirmatory ecotoxicity data, and amended labeling are received and accepted by the Agency. Products that contain additional active ingredients will be reregistered once the Agency completes eligibility decisions on the other active ingredients and once product specific and amended labeling are received and accepted.

Safety data

F
8-10-23
PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
rtecs
NL5250000
ridadr
UN 2811 6.1/PG 3
hs_code
29339990
Toxicity
LD50 i.p. in mice: 100 mg/kg (Anderson)
risk_code
25-36/37/38
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
T,Xi
hazard_note
Irritant
safety_code
26-36-45-38-36/37/39-28A
hazard_class
6.1
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group
III
Hazard statements
H301
Limited Quantities
5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications
Acute Tox. 3 Oral
Precautionary statements
P264-P270-P301+P310-P405-P501
Hazardous Substances Data
133-32-4(Hazardous Substances Data)
General Manufacturing Information
1H-Indole-3-butanoic acid: ACTIVE
Applications · 4 items

UsesIndole butyric acid (IBA) is a broad spectrum indole-class plant growth regulators and is a good rooting agent. It can promote the cuttings and rooting of herbaceous and woody ornamental plant. It can also be applied to the fruit setting of fruit as well as improving the fruit setting rate.

UsesUsed to stimulate root formation of plant clippings. Suitable for plant cell culture tested.

UsesIndole-3-butyric acid is auxin-family plant hormone (phytohormone). IBA is thought to be a precursor of indole-3-acetic acid (IAA) the most abundant and the basic auxin natively occurring and functioning in plants. IAA generates the majority of auxin effects in intact plants, and is the most potent native auxin.

General DescriptionIndole-3-butyric acid is a plant hormone in the auxin family and is widely used in agriculture since it induces rooting in various plants species such as mung bean (Vigna radiataL.) cuttings.

Preparation methods · 1 item

PreparationLaboratory put the mixture of indole, potassium hydroxide, and poly oxalic acid, dried tetrahydronaphthalene and γ-butyrolactone for heating under reflux to obtain the indole butyric acid. The reaction equation is as follows: Indole, potassium hydroxide, poly oxalic acid and dried tetrahydronaphthalene were added to the reaction vessel. The mixture was stirred for half an hour at room temperature; add γ-butyrolactone for heating reflux for 4 hours. The water remaining in the reaction system is removed by the water segregator. After cooling, the solid was totally dissolved by water with the separated organic layer being acidified with hydrochloric acid for precipitating a large number of off-white solid. Use suction filtration, wash with water, and dry to give the crude indole butyric acid with the yield of the crude product being 92.6%. After recrystallisation but aqueous ethanol, you can obtain white flaky crystals that is indole-3-butyric acid with the mp being 121.5~123 ℃. Reference: Daquan Wang (editor), “fine chemical production route” 2nd version, Beijing: Chemical Industry Press .1999 p. 260-261.

Upstream & downstream products

Upstream raw materials

BUTYRONITRILEGrignard reagentPotassium hydroxideTrapPolyethylene Glycol1,2,3,4-TetrahydronaphthaleneIndoleGamma Butyrolactone

Downstream products

1H-Indole-3-butanoic acid monosodium salt4-(1H-indol-3-yl)butanamidemethyl 4-(indol-3-yl)butyrate
Additional notes · 1 item

DefinitionChEBI: Indole-3-butyric acid is a indol-3-yl carboxylic acid that is butanoic acid carrying a 1H-indol-3-yl substituent at position 1. It has a role as a plant hormone, a plant metabolite and an auxin. It derives from a butyric acid. It is a conjugate acid of an indole-3-butyrate.