Forchlorfenuron

HCID 93379

Basic information

CAS
68157-60-8
Standard SMILES
O=C(Nc1ccccc1)Nc1ccnc(Cl)c1
InChIKey
GPXLRLUVLMHHIK-UHFFFAOYSA-N
Molecular formula
C12H10ClN3O
Average molar mass
247.68 g/mol
Monoisotopic mass
247.05123962

Overview

Forchlorfenuron is a member of the class of phenylureas that is urea substituted by a phenyl group and a 2-chloropyridin-4-yl group at positions 1 and 3 respectively. It is a plant growth regulator widely used in agriculture for improving fruit quality and fruit size. It has a role as a plant growth regulator. It is a member of phenylureas and a monochloropyridine.

Names & identifiers

Preferred name
Forchlorfenuron
IUPAC
1-(2-chloro-4-pyridinyl)-3-phenylurea
English name
Forchlorfenuron
Molecular formula
C12H10ClN3O
Molecular weight
247.68

Names & synonyms

Forchlorfenuron68157-60-8CPPU1-(2-Chloro-4-pyridyl)-3-phenylureaN-(2-Chloro-4-pyridyl)-N'-phenylureaSitofexKT-30Urea, N-(2-chloro-4-pyridinyl)-N'-phenyl-DTXSID1034634K62IP7463JN-(2-Chloro-4-pyridinyl)-N'-phenylureaDTXCID9014634
Show more names
4-CPPUForchlorofenuronPlant Growth Regulator Forchlorfenuron CPPU4pu30v3183fulmetskw20010
CHEBI:81861N-Phenyl-N'-(2-chloro-4-pyridyl)ureaRefChem:141177N-(2-chloropyridin-4-yl)-N'-phenylcarbamimidic acid614-346-01-(2-chloropyridin-4-yl)-3-phenylureaMFCD000598983-(2-chloropyridin-4-yl)-1-phenylurea

Database identifiers

CAS
68157-60-8
PubChem CID
93379
DTXSID
DTXSID1034634
ChEMBL
CHEMBL1229826
ChEBI
CHEBI:81861
UNII
K62IP7463J
EC Number
614-346-0
Nikkaji
J236.162K

Properties

Computed structural properties

XLogP
2.4
Topological polar surface area
54 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
17

Experimental & physicochemical properties

Pesticides · 3 items

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Approved

Pesticide (Forchlorfenuron) -> USDA PDB

LogP · 2 items

log Kow = 3.2 at 20 °C

3.2

Density1.3839 at 25 °C
Color/FormWhite to off-white crystalline powder
Solubility · 2 items

In methanol 119 g/L, ethanol 149 g/L, acetone 127 g/L, chlorofrom 2.7 g/LApplied at 1-1000 ppm, depending on crop.

In water = 39 mg/L (pH 6.4, 21 °C)

Flash PointFLASH POINT, °F: >200 Pensky Martin Closed Cup /Kim Blue Plant Growth Regulator/

Physicochemical properties

Melting point
170 · 170-172°C
Boiling point
308.4 · 308.4±27.0 °C(Predicted)
Density
1.415 · 1.415±0.06 g/cm3(Predicted)
storage temp.
2 · Inert atmosphere,2-8°C
solubility
Soluble in DMSO or Ethanol
pka
12.55 · 12.55±0.70(Predicted)

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H351: Suspected of causing cancer [Warning Carcinogenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Warning

H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 4 items

Commission Regulation No 844/2012

Forchlorfenuron is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

06/10/EC, Reg. (EU) 2017/1511, Reg. (EU) No 533/2013, Reg. (EU) No 540/2011, Reg.(EU) No 2018/679

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

Special ReportsUSEPA Office of Prevention, Pesticides and Toxic Substances, Pesticide Fact Sheet for Forchlorfenuron (September 2004).[Available from, as of November 21, 2011: http://www.epa.gov/opprd001/factsheets/]
FIFRA Requirements · 2 items

Tolerances are established for residues of the plant growth regulator forchlorfenuron; N-(2-chloro-4-pyridinyl)-N'-phenylurea in or on the following commodities: [Table#7911]

Time-limited tolerances are established for residues of the plant growth regulator forchlorfenuron; N-(2-chloro-4-pyridinyl)-N'-phenylurea in or on the food commodities: [Table#7912]

Hazard Classes and Categories · 4 items

Carc. 2 (100%)

Carcinogenicity - category 2

Serious eye damage/eye irritation - Category 2B

Carc. 2

Hazardous Reactivities and IncompatibilitiesKeep away from strong oxidizers such as hydrogen peroxide, bromine, and chromic acid. /Kim Blue Plant Growth Regulator/

Safety & protection

Fire Fighting ProceduresEXTINGUISHING MEDIA: Dry chemical or waterspray or waterfog or CO2 or Foam or Sand/Earth /Kim Blue Plant Growth Regulator/
Storage Conditions · 2 items

Store between 40 °F and 120 °F. /Kim Blue Plant Growth Regulator/

Do not contaminate water, food, or feed by storage or disposal. Keep pesticide in original container. /Kim Blue Plant Growth Regulator/

Cleanup Methods · 2 items

Absorb with an inert material such as sand, soil or vermiculite, and sweep up and dispose in accordance with federal, state and local regulations. /Kim Blue Plant Growth Regulator/

Do not contaminate water when cleaning equipment or disposing of equipment washwater or rinsate. /Kim Blue Plant Growth Regulator/

Disposal Methods · 3 items

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

PESTICIDE DISPOSAL: Wastes resulting from the use of this product may be disposed of on site or at an approved waste disposal facility. /Kim Blue Plant Growth Regulator/

CONTAINER DISPOSAL: Nonrefillable container. Do not reuse or refill this container. Offer for recycling, if available. Triple rinse container (or equivalent) promptly after emptying. Triple rinse as follows: Empty the remaining contents into application equipment or a mix tank and drain for 10 seconds after the flow begins to drip. Fill the container 1/4 full with water and recap. Shake for 10 seconds. Pour rinsate into application equipment or a mix tank or store rinsate for later use or disposal. Drain for 10 seconds after the flow begins to drip. Repeat this procedure two more times. /Kim Blue Plant Growth Regulator/

Preventive Measures · 5 items

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR 170. /Kim Blue Plant Growth Regulator/

Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 12 hours. /Kim Blue Plant Growth Regulator/

Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 12 hours. PPE required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil or water, is: long-sleeved shirt and long pants; chemical-resistant gloves such as barrier laminate, viton, butyl rubber, nitrile rubber, neoprene rubber, or polyvinyl chloride (PVC); shoes plus socks; protective eyewear such as goggles, safety shield, or safety glasses. /Kim Blue Plant Growth Regulator/

Users should: Wash hands thoroughly with soap and water before eating, drinking, chewing gum, using tobacco, or using the toilet. Remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. Remove PPE immediately after handling this product. Wash the outside of gloves before removing. As soon as possible, wash thoroughly and change into clean clothing. /Kim Blue Plant Growth Regulator/

For more Preventive Measures (Complete) data for Forchlorfenuron (6 total), please visit the HSDB record page.

Allowable Tolerances · 2 items

Tolerances are established for residues of the plant growth regulator forchlorfenuron; N-(2-chloro-4-pyridinyl)-N'-phenylurea in or on the following commodities: [Table#7909]

Time-limited tolerances are established for residues of the plant growth regulator forchlorfenuron; N-(2-chloro-4-pyridinyl)-N'-phenylurea in or on the food commodities: [Table#7910]

Toxicology

Ecotoxicity Values · 5 items

LD50; Species: Colinus virginianus (Bobwhite quail) oral > or =2250 ppm

LC50; Species: Colinus virginianus (Bobwhite quail) subacute dietary >5620 ppm

LC50; Species: Anas platyrhynchos (Mallard duck) subacute dietary >5620 ppm

LC50; Species: Oncorhynchus mykiss (Rainbow trout); Concentration: >9.2 ppm (acute) /Conditions of bioassay not specified in source examined/

For more Ecotoxicity Values (Complete) data for Forchlorfenuron (6 total), please visit the HSDB record page.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 852-3320 measured in four soils(2), indicates that forchlorfenuron is expected to have moderate to low to slight mobility in soil(SRC). Volatilization of forchlorfenuron from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 2.86X10-12 atm-cu m/mole(2). Forchlorfenuron is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.45X10-10 mm Hg at 25 °C(2). Soil degradation studies using natural and sterilized soils found that forchlorfunuron degradation rates were faster in the natural soils suggesting that microbial degradation might be the major pathway of residue dissipation in soil(3). Dissipation rates in soil are reported to be slow with extractable residue half-lives of 578 days in one study(4). Another laboratory study observed dissipation half-lives of 15.1 to 121.3 days depending on soil type and moisture content(5).

AQUATIC FATE: Based on a classification scheme(1), a Koc range of 852-3320 measured in four soils(2), indicates that forchorfenuron is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 2.86X10-12 atm-cu m/mole(2). According to a classification scheme(4), a BCF of 7.2 measured in bluegill fish(5), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Forchlorfenuron is stable to hydrolysis (30-day incubation period) at pH5, pH7 and pH9 at 25 °C(5). Forchlorfenuron did not undergo direct photolysis in aqueous solution in laboratory tests, but did photolyze in sensitized solutions (half-life of 5 days)(5). An anaerobic study in a flooded water-sediment system found a fenchlorfenuron half-life of 226 days(5). The laboratory dissipation half-lives in irrigation water collected from fields where forchlorfenuron was applied ranged from 43.3 to 64.5 days(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), forchlorfenuron, which has a vapor pressure of 3.45X10-10 mm Hg at 25 °C(2) is expected to exist solely in the particulate phase. Particulate-phase forchlorfenuron may be removed from the air by wet or dry deposition(SRC).

Soil Adsorption/Mobility · 1 item

A Koc range of 852-3320 (mean of 1763) was reported for four soils(1). According to a classification scheme(2), this Koc range suggests that forchlorfenuron is expected to have low to slight mobility in soil. Forchlorfenuron was considered to be moderately mobile to essentially immobile in soils with Freundlich Kads values of 2-20(3). Adsorption-desorption studies using three Indian soils classified forchlorfenuron as a chemical in the low to medium leaching category(4).

Artificial Pollution SourcesForchlorfenuron's production may result in its release to the environment through various waste streams; its use as a plant growth regulator(1) will result in its direct release to the environment(SRC).
Environmental Biodegradation · 3 items

AEROBIC: Soil degradation studies using natural and sterilized soils (clay, sandy-loam and silty-loam grapevine soils in India) found that forchlorfunuron degradation rates were faster in the natural soils suggesting that microbial degradation might be the major pathway of residue dissipation(1).

AEROBIC: Forchlorfenuron, at a nominal application rate of 10 ug/g, was essentially stable in sandy loam soil incubated in darkness at 25 °C for up to 12 months. The calculated half-lives for extractable residues were 578 days and 1659 days for the sum of extractable and bound, respectively. The parent compound appeared to be relatively stable at 2 to 9 months post treatment. No degradates other than CO2 were detected. Evolved CO2 was a 0.81-0.95% of the applied at 2-9 months and was 0.061% of the applied at 12 months post treatment; organic volatiles were negligible. In sediment/water systems, forchlorfenuron, at a nominal concentration of 10 ug/g, sorbed onto soil and did not degrade significantly based on the sum of extractable, bound, and water residues(1).

ANAEROBIC: A half-life of 226 days for fenchlorfenuron incubated in anaerobic (nitrogen) flooded sandy loam soil was based on extractable residues. The parent compound appeared to be relatively stable in the water and soil phases from 60 to 90 days post treatment (anaerobic incubation days 30-60). Degradates were not detected in the soil or water phases(1).

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Regulatory information

FIFRA Requirements · 2 items

Tolerances are established for residues of the plant growth regulator forchlorfenuron; N-(2-chloro-4-pyridinyl)-N'-phenylurea in or on the following commodities: [Table#7911]

Time-limited tolerances are established for residues of the plant growth regulator forchlorfenuron; N-(2-chloro-4-pyridinyl)-N'-phenylurea in or on the food commodities: [Table#7912]

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
YS7182500
ridadr
UN3077 9/PG 3
hs_code
29333990
Toxicity
LD50 oral in mouse: > 500mg/kg

Chemistry & industry

Pharmacology

Mechanism of Action · 2 items

Septins are filamentous GTPases that associate with cell membranes and the cytoskeleton and play essential roles in cell division and cellular morphogenesis. Septins are implicated in many human diseases including cancer and neuropathies. Small molecules that reversibly perturb septin organization and function would be valuable tools for dissecting septin functions and could be used for therapeutic treatment of septin-related diseases. Forchlorfenuron is a plant cytokinin previously shown to disrupt septin localization in budding yeast. However, it is unknown whether forchlorfenuron directly targets septins and whether it affects septin organization and functions in mammalian cells. Here, we show that forchlorfenuron alters septin assembly in vitro without affecting either actin or tubulin polymerization. In live mammalian cells, forchlorfenuron dampens septin dynamics and induces the assembly of abnormally large septin structures. Forchlorfenuron has a low level of cytotoxicity, and these effects are reversed upon forchlorfenuron washout. Significantly, forchlorfenuron treatment induces mitotic and cell migration defects that phenocopy the effects of septin depletion by small interfering RNA.

It promotes cell division, differentiation and development; induces budding of callus, and controls apical dominance; breaks dormancy of lateral buds and promotes germination; delays ageing process and maintains chlorophyll in excised leaves; regulates the transport of nutrients; promotes fruit formation, etc.

Biological Half-Life · 1 item

At least 4 Sprague-Dawley rats/sex were dosed orally by gavage with 100 mg/kg of CPPU-UL-phenyl-(14)C (radiochemical purity: 99.16%; specific activity: 28.04 mCi/mmol) fortified with unlabeled Forchlorfenuron technical (purity: 98.2%). ... The excretory half-lives ranged from 13 to 16 hours for both sexes for both the urine and feces.

Metabolism/Metabolites · 1 item

At least 4 Sprague-Dawley rats/sex were dosed orally by gavage with 100 mg/kg of CPPU-UL-phenyl-(14)C (radiochemical purity: 99.16%; specific activity: 28.04 mCi/mmol) fortified with unlabeled Forchlorfenuron technical (purity: 98.2%). ... The primarily metabolite recovered in the urine was CPPU-sulfate with substitution on the phenyl ring. It represented 84 and 57% of the administered dose for the males and females, respectively. Other metabolites were products of phenyl ring hydroxylations as well. Hydroxyl-CPPU was the predominant metabolite recovered from the feces with 11 and 18% of the administered dose recovered from the males and females, respectively.

MeSH Pharmacological ClassificationAny of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.
Absorption, Distribution and Excretion · 2 items

In both the main study and the biliary excretion study, at least 4 Sprague-Dawley rats/sex were dosed orally by gavage with 100 mg/kg of CPPU-UL-phenyl-(14)C (radiochemical purity: 99.16%; specific activity: 28.04 mCi/mmol) fortified with unlabeled Forchlorfenuron technical (purity: 98.2%). In the main study, urine, feces and air samples were collected periodically for 7 days post-dose. In the biliary excretion study, bile samples were collected periodically via the bile duct cannula up to 72 hours post-dose. The primary route of excretion was in the urine ((M) urine: 79%, feces: 16%, (F) urine: 68%, feces: 28%). During the 1st 24 hours post-dose, 82% of the radiolabel was recovered from the males and 66% from the females. Less than 0.1% of the administered dose was recovered in the air. The excretory half-lives ranged from 13 to 16 hours for both sexes for both the urine and feces. Recovery in the tissues at 7 days post dose represented less than 1% of the administered dose. In the biliary excretion study, 23 and 20% of the administered radiolabel were recovered in the bile from the males and females, respectively. However, the absorption kinetics could not be readily assessed because no urine or feces samples were collected simultaneously from these study animals.

Absorbed by leaves, stem, cotyledon and germinated seeds.

Uses & manufacturing

Uses · 4 items

For forchlorfenuron (USEPA/OPP Pesticide Code: 288008) 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./

Forchlorfenuron is a plant growth regulator registered for use on grapes raisins, and kiwifruit.

Plant growth regulator. Used to increase the size of kiwi fruit and table grapes.

Forchlorfenuron is a diphenylurea-derivative cytokinin growth stimulating substance used as plant growth regulator (PGR) to enhance fruit set, size and increase yields. Forchlorfenuronis is commonly used in horticulture to stimulate the growth of kiwi fruit and grapes.

Consumption PatternsApplied at 1-1000 ppm, depending on crop.
Formulations/Preparations · 5 items

Soluble powder.

Gibberellic Acid (Kim-C1, LLC): Forchlorfenuron 98%.

KT-30 Technical (Kim-C1, LLC): Forchlorfenuron 98%.

ABG-3207 Plant Growth Regulator (Kim-C1, LLC): Forchlorfenuron 0.8%.

For more Formulations/Preparations (Complete) data for Forchlorfenuron (6 total), please visit the HSDB record page.

Applications · 2 items

DescriptionForchlorfenuron (68157-60-8) reversibly perturbs mammalian septin assembly, organization and function. Has no effect on actin or tubulin polymerization.1,2 FCF induces effects on mitosis and migration which phenocopy the effects induced by septin depletion using siRNA.1 A useful tool for exploring the physiological role of septin and its complexes.3,4

UsesForchlorfenuronis is a diphenylurea-derivative cytokinin. Forchlorfenuronis is used as a plant growth regulator (PGR). Forchlorfenuronis is commonly used in horticulture to stimulate the growth of kiw i fruit and grapes.

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Forchlorfenuron is a member of the class of phenylureas that is urea substituted by a phenyl group and a 2-chloropyridin-4-yl group at positions 1 and 3 respectively. It is a plant growth regulator widely used in agriculture for improving fruit quality and fruit size. It has a role as a plant growth regulator. It is a member of phenylureas and a monochloropyridine.

Related reactions

3 records

Compound notes

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