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Pinoxaden

PubChem CID
210326
Structure
Pinoxaden_small.png
Pinoxaden_3D_Structure.png
Pinoxaden__Crystal_Structure.png
Molecular Formula
Synonyms
  • Pinoxaden
  • 243973-20-8
  • Pinoxaden [ISO]
  • UNII-U55GLF9LV9
  • U55GLF9LV9
Molecular Weight
400.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-09
  • Modify:
    2025-01-18
Description
Pinoxaden is a pyrazolooxadiazepine that is 7-oxo-1,2,4,5-tetrahydro-7H-pyrazolo[1,2-d][1,4,5]oxadiazepin which is substituted at positions 8 and 9 by 2,6-diethyl-4-methylphenyl and pivaloyloxy groups, respectively. A pro-herbicide (by hydrolysis of the pivalate ester to give the corresponding enol), it is used for control of grass weeds in cereal crops. It has a role as a xenobiotic, an environmental contaminant, an agrochemical, an EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor and a proherbicide. It is a pivalate ester and a pyrazolooxadiazepine. It is functionally related to a pinoxaden acid.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Pinoxaden.png

1.2 3D Conformer

1.3 Crystal Structures

CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[8-(2,6-diethyl-4-methylphenyl)-7-oxo-1,2,4,5-tetrahydropyrazolo[1,2-d][1,4,5]oxadiazepin-9-yl] 2,2-dimethylpropanoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C23H32N2O4/c1-7-16-13-15(3)14-17(8-2)18(16)19-20(26)24-9-11-28-12-10-25(24)21(19)29-22(27)23(4,5)6/h13-14H,7-12H2,1-6H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

MGOHCFMYLBAPRN-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCC1=CC(=CC(=C1C2=C(N3CCOCCN3C2=O)OC(=O)C(C)(C)C)CC)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C23H32N2O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 Metabolomics Workbench ID

2.3.8 Nikkaji Number

2.3.9 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

pinoxaden

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
400.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
4.6
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
400.23620751 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
400.23620751 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
59.1 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
29
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
652
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Color / Form

Fine white powder
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)

3.2.2 Odor

Odorless
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)

3.2.3 Melting Point

120.5-121.6 °C
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)

3.2.4 Solubility

Solubilities (g/L): acetone 250; dichloromethane >500; ethyl acetate 130; hexane 1.0; methanol 260; octanol 140; toluene 130
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)
In water, 220 mg/L at 25 °C
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)

3.2.5 Density

1.16 at 21 °C
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)

3.2.6 Vapor Pressure

2.0X10-4 mPa at 20 °C; 4.6X10-4 mPa at 25 °C /SRC: 3.5X10-9 mm Hg at 25 °C/
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)

3.2.7 LogP

log Kow = 3.2
MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)

3.2.8 pH

pH 4.71 at 25 °C
US EPA; Pesticide Fact Sheet. Pinoxaden. July 2005. US EPA, Off Prevt Pest Tox Sub (7501C). Available from, as of Feb 24, 2011: https://www.epa.gov/opprd001/factsheets/pinoxaden.pdf

3.2.9 Other Experimental Properties

White solid; odorless; MP: 120.5-121.6 °C; density: 1.16X10+3 kg/cu m at 24 °C; solubility in water: 200 mg/L at 20 °C; VP: 4.6X10-7 Pa /SRC: 3.45X10-9 mm Hg/ at 25 °C; log Kow = 3.2 at 25 °C; pH 4.9 at 25 °C /Technical/
US EPA; Pesticide Fact Sheet. Pinoxaden. July 2005. US EPA, Off Prevt Pest Tox Sub (7501C). Available from, as of Feb 24, 2011: https://www.epa.gov/opprd001/factsheets/pinoxaden.pdf

3.3 Chemical Classes

3.3.1 Pesticides

Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Approved
Environmental transformation -> Pesticides (parent, predecessor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759
Herbicides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688
Pesticide (Pinoxaden) -> USDA PDB

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 LC-MS

1 of 17
View All
Authors
Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag
Instrument
LTQ Orbitrap XL Thermo Scientific
Instrument Type
LC-ESI-ITFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
35 % (nominal)
Fragmentation Mode
CID
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
13.7 min
Precursor m/z
401.2435
Precursor Adduct
[M+H]+
Top 5 Peaks
317.1864 999
Thumbnail
Thumbnail
License
CC BY
2 of 17
View All
Authors
Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag
Instrument
LTQ Orbitrap XL Thermo Scientific
Instrument Type
LC-ESI-ITFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
15 % (nominal)
Fragmentation Mode
HCD
Column Name
XBridge C18 3.5um, 2.1x50mm, Waters
Retention Time
13.7 min
Precursor m/z
401.2435
Precursor Adduct
[M+H]+
Top 5 Peaks

401.2432 999

317.1858 46

Thumbnail
Thumbnail
License
CC BY

6 Chemical Vendors

7 Agrochemical Information

7.1 Agrochemical Category

Herbicide
Pesticide active substances
Herbicides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

7.2 Agrochemical Transformations

Pinoxaden has known environmental transformation products that include NOA 407854 (M2) and NOA 447204 (M3).
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759

7.3 EU Pesticides Data

Active Substance
pinoxaden
Status
Approved [Reg. (EC) No 1107/2009]
Date
Approval: 01/07/2016 Expiration: 30/06/2026
Legislation
2005/459/EC, 2012/191/EU, Reg. (EU) 2016/370, Reg. (EU) No 289/2014, Reg. (EU) No 540/2011
ADI
0.1 mg/kg bw/day [Reg. (EU) 2016/370]
ARfD
0.1 mg/kg bw [Reg. (EU) 2016/370]
AOEL
0.1 mg/kg bw/day [Reg. (EU) 2016/370]

7.4 USDA Pesticide Data Program

8 Pharmacology and Biochemistry

8.1 Absorption, Distribution and Excretion

In a ... rabbit metabolism study, a single oral dose of (Phenyl-1-(14)C) NOA 407855 (/pinoxaden/ Batch/lot # ILA-8.1B-5 and ILA-8.1C-1B; radiochemical purity $98.9%) was administered in aqueous 0.5% carboxymethylcellulose and 0.1% Tween 80 to female Chbb-HM rabbits (3/dose) via gavage at nominal dose levels of 0.5 and 300 mg/kg. Urine, feces, and blood samples were collected up to 168 hours after dosing. Metabolites in urine and feces were quantified and identified by HPLC, TLC, and LC/MS. Animals were sacrificed after 168 hours, and tissues were collected to determine of residual radioactivity. Absorption and elimination of (14)C NOA 407855 were rapid and essentially complete regardless of dose level. Maximum concentrations (Cmax) in blood were attained within 0.5 hours at the low dose and within approximately 2 hours at the high dose. Half lives for radioactivity in the blood were 3 and 12 hours for the low and high dose groups, and radioactivity in blood was non-detectable by 48 and 96 hours for the low and high dose groups. The total recovery of the radioactive dose averaged 94.7-100.1% at 168 hours post-dose. The route of excretion was essentially independent of dose, although excretion was slightly retarded at the high dose compared to the low dose. Approximately 90% of the dose was excreted in the urine within 24 (low dose) or 48 (high dose) hours. An additional 4-7% dose was excreted in the feces within 48 hours. For both dose groups, concentrations of radioactivity remaining in the tissues were negligible by 168 hours post-dose and accounted for less than or equal to 0.1% of the dose. Quantifiable residues were detect in gall bladder and gastrointestinal (GI) tract for both the low dose group (0.0020-0.0025 ppm Eq) and high dose group (1.66-1.69 ppm Eq), and in the kidneys, liver, plasma, and blood (0.017-0.158 ppm) of the high dose group. However, radioactivity in the remaining tissues was below the limit of quantitation (LOQ). Essentially all of the metabolites excreted in the urine and feces were identified (92.8-97.7% dose), and the metabolite profile was the same regardless of dose level. For both dose groups, Metabolite M2 (NOA 407854) was identified as the major component in both urine (88.6-91.0% dose) and feces (3.6-6.2% dose). Minor amounts of Metabolites M4 (0.4-0.6% dose), K4 (0.2% dose), M12 (0.2% dose) and K3 (0.1% dose) were also identified in urine and/or feces. Unidentified metabolites accounted for less than or equal to 0.6% dose. In rabbits, the metabolism of NOA 407885 proceeds predominantly by hydrolysis of the ester linkage to form Metabolite M2 (NOA 407854), which is the major metabolite in urine and feces (92-97% dose). Minor secondary reactions include either: hydroxylation at the 4-methyl group of the phenyl moiety to yield M4 (excreted in urine and feces); or glucuronidation of M2 to form metabolite M12. The metabolic pathway in the rabbit is essentially identical to the rat.
USEPA; Pinoxaden: Human Health Risk Assessment.p.76-7 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf
Dermal absorption is estimated to be 40% based on the results of the in vivo/in vitro dermal penetration study in rats using the EC 100 formulation. (The emulsifiable concentrate (EC) formulation will be used in the field and is believed to be much more absorbable than technical pinoxaden without the emulsifiers.) In this study with the EC formulation, 36% of the dose applied to the skin of rats in an in vivo study was absorbed over the following day (24 hours post-exposure). Absorption of the EC formulation from excised rat skin in an in vitro study was 65.5% of the applied dose after 24 hours post-exposure. For excised human skin, absorption of radioactivity was minimal regardless of the dosing vehicle and dose level in an in vitro study. Absorption accounted 0.36-1.84% of the applied dose after a 24-hour exposure at doses from 5-400 :g/cm2. Thus, in the in vitro studies, absorption was considerably higher in rat skin than in human skin. Additionally, absorption of the test substance in the in vivo rat study was comparable to the absorption in the in vitro study with rat skin. Therefore, the data suggest that in vivo absorption in humans would be considerably lower than in the rat.
USEPA; Pinoxaden: Human Health Risk Assessment.p.39 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf
In a ... mouse metabolism study, (pyrazol-3,5-(14)C) NOA 407855 (/pinoxaden/ greater than or equal to 97.6% radiochemical purity; Lots ILA-76.3B ILA-76.3C) was administered to 4 groups of male and female C57BL/10Jf/CD-1 mice as follows: (I) Group G1 was given either a single-dose or repeated daily dose of 1.4 mg/kg body-weight by gavage; (ii) Group G2 was administered either a single-dose or repeated daily dose of 140 mg/kg body-weight by gavage; (iii) Group G3 was fed at 10 ppm in the diet; and (iv) Group G4 was fed a 1000 ppm diet. The maximum duration of dosing in each group was for 18 days. Terminal blood samples were collected to determine a time course of the concentration of radioactivity in whole blood, and urine and feces were collected over 24 hours after varying time periods of dosing. The stated objectives of this study were to: (I) investigate the duration of dosing required to reach steady-state kinetics; (ii) compare systemic exposure following gavage or dietary dosing and determine any marked sex difference; (iii) compare blood and excreta metabolite profiles after single and multiple dosing to male and female mice; and (iv) resolve which metabolite should be analyzed during dietary studies. Radioactivity levels in whole blood sampled at various post-dose intervals indicated that the gavage dose was rapidly absorbed (Tmax = 0.5 hours) and eliminated regardless of the dose level or the duration of dosing. Absorption was slower for the dietary dosing groups (Tmax = 8-12 hours), but elimination from the blood was rapid once mice were withdrawn from the treated diet. Concentrations in blood at Tmax following 1, 7, 14, and 18 days of dietary dosing indicated that a steady state in blood levels was achieved within 18 days. Although urinary excretion was typically higher than fecal excretion, there was no clear pattern in the distribution of excreted radioactivity between urine and feces based on sex, dosing group, or duration of dosing. Radioactivity in urine (including cage wash) varied from 26-83% of the excreted radioactivity and in feces from 17-74%. Following oral administration of NOA 407855 to mice either by gavage or in the diet, the metabolite profiles in blood, urine and feces were qualitatively and quantitatively independent of sex, dose level, dosing method (gavage vs. dietary), dosing duration (single vs. multiple doses) and time of collection, although some quantitative variations were observed in feces. Parent compound was not detected in blood, urine or feces. Metabolite M2 (NOA 407854) was the major component identified in all three matrices, accounting for approximately 67-93% of the extractable blood radioactivity, 69-89% of the total radioactivity in urine, and 35-75% of the radioactivity extractable from feces. Substantial amounts of Metabolite M4 were also detected in blood (2-11% extractable blood radioactivity), urine (5-14% of total radioactivity), and feces (12-41% of the extractable radioactivity). The remaining components detected in each matrix were minor (<8% of the sample radioactivity) and included five components in blood extracts, eight components in urine, and 8-11 components in fecal extracts. The presence of Metabolites M2 and M4 in urine and feces were confirmed by LC/MS and LC/NMR analyses of fractions isolated from composited samples. These analyses also identified minor amounts (<3% sample radioactivity) of Metabolites M13, M21, M50, and M51 in urine and Metabolites M13, M19, M20, M22, M49, and M50 in fecal extracts. Based on the metabolites identified in blood, urine and feces and their relative abundance, the metabolism of NOA 407855 in mice primarily involves hydrolysis of the ester moiety to form Metabolite M2, which is the primary component excreted in urine and feces. To a minor extent, Metabolite M2 may also undergo a number of secondary reactions to produce variety of minor metabolites. These secondary reactions include: hydroxylation, oxidation, hydrolysis, dealkylation, ring formation, and cleavage of the ether bond in the oxadiazepine moiety.
USEPA; Pinoxaden: Human Health Risk Assessment.p.77-8 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf
In an in vivo dermal penetration study, (pyrazole-3, 5-(14)C) NOA407855 (/pinoxaden/ >95% radiochemical purity, lot/batch #EZ005006) was suspended in an emulsifiable concentrate (EC) formulation and applied neat or as aqueous dilutions to approximate exposure to the undiluted commercial formulation and to the dilute aqueous spray used in the field. The formulated test substance was administered to the shaved intact skin (10 sq cm) of 4 male Alpk:APfSD (Wistar-derived) rats/time point/dose at dose levels of 5 and 25 ug/sq cm for the aqueous dilutions (1/200 and 1/40) and 400 ug/cm2 for the neat EC formulation for a 4- or 10-hour exposure period. At the end of the exposure period, the skin of each rat was washed, and 4 rats/time point/dose were sacrificed for examination of dermal-absorption. A further 4 rats/dose were exposed for 10 hours and then retained for 24 hours after the skin was washed to determine further post-exposure absorption. In addition, in vitro studies were conducted using excised rat skin and human skin mounted in a static diffusion cell apparatus to compare dermal-absorption. The dosing regimen used in the in vitro studies was the same as in the in vivo study, except that an additional dose level of 1000 ug/sq cm was employed for human skin using the neat EC formulation. Absorption from excised skin samples was examined after 10- and 24-hour exposure durations, except at the 1000 ug/sq cm dose level which used only a 10-hour exposure. For the in vivo rat study, total recovery of the applied dose ranged from 84-96% for all dose groups. For the neat EC formulation (400 ug/sq cm), 17% of the dose was absorbed after 4 hours and 30% dose after 10 hours, increasing to 36% dose over the following day (24 hours post-exposure). Regardless of exposure duration, 7% dose remained available in or on the skin for potential absorption, with 1.3-1.4% of the dose in the stratum corneum. At 24 hours post-exposure, the potentially absorbable dose declined to 5.3% dose, with 1.4% of the dose in the stratum corneum. Most of the absorbed radioactivity was excreted in the urine (including cage wash), accounting for approximately 30% of the applied dose (83% of the absorbed dose), and 3.3% dose was eliminated in the feces (9% of the absorbed dose). Excretion was virtually complete within 24 hours, with only 1.5% of the dose being recovered in the GI tract and carcass. For the 1/40 aqueous spray dilution (25 ug/sq cm), absorption was markedly lower than for the EC formulation, with only 0.7 and 1.6% of the dose being absorbed by 4 and 10 hours, respectively. After a 10-hour exposure and washing, there was an increase in absorption up to 3.8% dose by 24 hours post-dose. Potentially absorbable radioactivity in or on the skin following washing accounted for 2.6-3.1% of the dose at all sampling intervals and was primarily associated with the stratum corneum (2.0-2.3% dose). As with the high-dose group, most of the absorbed radioactivity was excreted within 24 hours in the urine (66% of absorbed dose) and feces (11% of absorbed dose). For the in vitro studies using excised rat and human skin, total recovery of the applied dose ranged from 94-104% for all dose groups at both exposure intervals. As in the in vivo study, absorption from excised rat skin was higher for the neat EC formulation (400 ug/sq cm) than for either of the 1/200 or 1/40 aqueous dilutions (5 and 25 ug/sq cm, respectively). Following a 10-hour exposure, 40.3% of the applied dose from the EC formulation was absorbed compared to 34.1 and 25.0% of the applied dose from aqueous dilutions (5 and 25 ug/sq cm). After 24 hours of exposure, absorption rose to 65.5% dose for the EC formulation and 49.0 and 44.7% dose for the aqueous dilutions. Regardless of exposure duration, potentially absorbable radioactivity remaining on the skin accounted for 8.8-11.8% dose for the neat EC formulation, 12.1-12.9% dose for the 1/40 aqueous dilution, and 18.5-20.6% dose for the 1/200 aqueous dilution. For excised human skin, absorption of radioactivity was minimal regardless of the dosing vehicle and dose level. Absorption accounted for 0.34-1.55% of the applied dose after a 10-hour exposure at doses from 5-1000 ug/sq cm and 0.36-1.84% of the applied dose after a 24-hour exposure at doses from 5-400 ug/sq cm. Potentially absorbable radioactivity remaining in or on the skin (stratum corneum and epidermis) accounted for 2.42-3.61% dose in the greater than or equal to 25 ug/sq cm dose groups and 8.49-8.80% dose in the 5 ug/sq cm dose group. Thus, in the in vitro studies, absorption was considerably higher in rat skin than in human skin. Additionally, absorption of the test substance in the in vivo rat study was comparable to the absorption in the in vitro study with rat skin. Therefore, the data may suggest that in vivo absorption in humans would be considerably lower than in the rat.
USEPA; Pinoxaden: Human Health Risk Assessment.p.80-1 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf

8.2 Metabolism / Metabolites

From livestock metabolism studies, the residues with concentrations >10% total radioactive residue were chosen as residues of concern for livestock. Therefore, besides the parent compound, M2 and M4 (free and conjugated) for ruminants and M2, M4 (free and conjugated), and M6 for poultry were determined to be residues of concern. M4 is the major metabolite in the livestock. ((14)Cphenyl)-pinoxaden and ((14)C-phenyl)-M4 were the only compounds that were fed to ruminants in two separate studies.
USEPA; Pinoxaden: Human Health Risk Assessment.p.20 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf
The metabolism of pinoxaden in rats primarily involves the initial hydrolysis of the ester moiety to form metabolite M2 (NOA 407854), which is then extensively excreted in the urine and feces. To a minor extent, metabolite M2 is also further metabolized via hydroxylation, dealkylation, ring cleavage, ring formation, and conjugation into a wide variety of minor metabolites. The proposed pathway is also supported by the appended in vitro study, which indicates that pinoxaden is rapidly hydrolyzed to M2 in rat plasma (half life = approximately 0.1 min) at concentrations up to 100 uM (approximately 40 ppm).
USEPA; Pinoxaden: Human Health Risk Assessment.p.14 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf
In a ... rabbit metabolism study, a single oral dose of (Phenyl-1-(14)C) NOA 407855 (/pinoxaden/ Batch/lot # ILA-8.1B-5 and ILA-8.1C-1B; radiochemical purity $98.9%) was administered in aqueous 0.5% carboxymethylcellulose and 0.1% Tween 80 to female Chbb-HM rabbits (3/dose) via gavage at nominal dose levels of 0.5 and 300 mg/kg. Urine, feces, and blood samples were collected up to 168 hours after dosing. Metabolites in urine and feces were quantified and identified by HPLC, TLC, and LC/MS. ... Essentially all of the metabolites excreted in the urine and feces were identified (92.8-97.7% dose), and the metabolite profile was the same regardless of dose level. For both dose groups, Metabolite M2 (NOA 407854) was identified as the major component in both urine (88.6-91.0% dose) and feces (3.6-6.2% dose). Minor amounts of Metabolites M4 (0.4-0.6% dose), K4 (0.2% dose), M12 (0.2% dose) and K3 (0.1% dose) were also identified in urine and/or feces. Unidentified metabolites accounted for less than or equal to 0.6% dose. In rabbits, the metabolism of NOA 407885 proceeds predominantly by hydrolysis of the ester linkage to form Metabolite M2 (NOA 407854), which is the major metabolite in urine and feces (92-97% dose). Minor secondary reactions include either: hydroxylation at the 4-methyl group of the phenyl moiety to yield M4 (excreted in urine and feces); or glucuronidation of M2 to form metabolite M12. The metabolic pathway in the rabbit is essentially identical to the rat.
USEPA; Pinoxaden: Human Health Risk Assessment.p.76-7 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf
In a ... mouse metabolism study, (pyrazol-3,5-(14)C) NOA 407855 (/pinoxaden/ greater than or equal to 97.6% radiochemical purity; Lots ILA-76.3B ILA-76.3C) was administered to 4 groups of male and female C57BL/10Jf/CD-1 mice as follows: (I) Group G1 was given either a single-dose or repeated daily dose of 1.4 mg/kg body-weight by gavage; (ii) Group G2 was administered either a single-dose or repeated daily dose of 140 mg/kg body-weight by gavage; (iii) Group G3 was fed at 10 ppm in the diet; and (iv) Group G4 was fed a 1000 ppm diet. The maximum duration of dosing in each group was for 18 days. ... Following oral administration of NOA 407855 to mice either by gavage or in the diet, the metabolite profiles in blood, urine and feces were qualitatively and quantitatively independent of sex, dose level, dosing method (gavage vs. dietary), dosing duration (single vs. multiple doses) and time of collection, although some quantitative variations were observed in feces. Parent compound was not detected in blood, urine or feces. Metabolite M2 (NOA 407854) was the major component identified in all three matrices, accounting for approximately 67-93% of the extractable blood radioactivity, 69-89% of the total radioactivity in urine, and 35-75% of the radioactivity extractable from feces. Substantial amounts of Metabolite M4 were also detected in blood (2-11% extractable blood radioactivity), urine (5-14% of total radioactivity), and feces (12-41% of the extractable radioactivity). The remaining components detected in each matrix were minor (<8% of the sample radioactivity) and included five components in blood extracts, eight components in urine, and 8-11 components in fecal extracts. The presence of Metabolites M2 and M4 in urine and feces were confirmed by LC/MS and LC/NMR analyses of fractions isolated from composited samples. These analyses also identified minor amounts (<3% sample radioactivity) of Metabolites M13, M21, M50, and M51 in urine and Metabolites M13, M19, M20, M22, M49, and M50 in fecal extracts. Based on the metabolites identified in blood, urine and feces and their relative abundance, the metabolism of NOA 407855 in mice primarily involves hydrolysis of the ester moiety to form Metabolite M2, which is the primary component excreted in urine and feces. To a minor extent, Metabolite M2 may also undergo a number of secondary reactions to produce variety of minor metabolites. These secondary reactions include: hydroxylation, oxidation, hydrolysis, dealkylation, ring formation, and cleavage of the ether bond in the oxadiazepine moiety.
USEPA; Pinoxaden: Human Health Risk Assessment.p.77-8 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf
In a ... study designed to correlate the levels of Metabolite M2 (NOA 407854) in the blood with the ingestion of NOA 407855 /pinoxaden/ in the diet, four groups of C57Bl/10JfCD-1 mice (24/sex/dose group) were fed diets containing NOA 407855 (97.2% ai, Lot #EZ005006) for at least 39 consecutive days. Two groups were fed diets containing NOA 407855 at 1000 or 2500 ppm for the entire period; the third group was fed at 2500 ppm for 7 days, followed by 5000 ppm for at least 32 consecutive days; and the fourth group was fed at 2500 ppm for 7 days, followed by 5000 ppm for 14 days, and then 7000 ppm for at least 18 days. A fifth group of mice (3 or 4/sex) of the same source and strain served as controls for the duration of the study. ... Concentrations of M2 in blood on Study days 40 and 41 averaged 1.7-2.3 mg/kg at 1000 mg/kg, 4.6-7.4 mg/kg at 2500 ppm, 11.8-12.7 mg/kg at 5000 ppm, and 17.0-20.8 mg/kg at 7000 ppm. Linear regression showed a direct correlation between the concentration of M2 in the blood and the concentration of the test material in the diet, with R2 = 0.96 for females and 0.98 for males. There were no apparent differences in M2 blood concentrations between sexes or time of blood sampling at any dose.
USEPA; Pinoxaden: Human Health Risk Assessment.p.78-9 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf

8.3 Biological Half-Life

In a ... rabbit metabolism study, a single oral dose of (Phenyl-1-(14)C) NOA 407855 (/pinoxaden/ Batch/lot # ILA-8.1B-5 and ILA-8.1C-1B; radiochemical purity $98.9%) was administered in aqueous 0.5% carboxymethylcellulose and 0.1% Tween 80 to female Chbb-HM rabbits (3/dose) via gavage at nominal dose levels of 0.5 and 300 mg/kg. Urine, feces, and blood samples were collected up to 168 hours after dosing. ... Half lives for radioactivity in the blood were 3 and 12 hours for the low and high dose groups, and radioactivity in blood was non-detectable by 48 and 96 hours for the low and high dose groups.
USEPA; Pinoxaden: Human Health Risk Assessment.p.76 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf

8.4 Mechanism of Action

Pinoxaden (NOA 407855) is a representative of the new phenylpyrazolin class of chemicals. The mode of action is the inhibition of the enzyme, acetyl-coenzyme A carboxylase (ACCase). ACCase activity in plants can be attributed to two isoenzymes located in different compartments of the plant cell, the chloroplast and the cytosol. The chloroplastic enzyme is responsible for the de novo biosynthesis of all fatty acids in the cell. The malonyl-coenzyme A produced by the cytosolic ACCase is required for fatty acid elongation to form very long-chain fatty acids, and for the biosynthesis of flavonoids and malonylated metabolites. Pinoxaden has been found to inhibit both the chloroplastic and the cytosolic ACCase enzyme in gramineae.
USEPA; Pinoxaden: Human Health Risk Assessment.p.5 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf

8.5 Transformations

9 Use and Manufacturing

9.1 Uses

For pinoxaden (USEPA/OPP Pesticide Code: 147500) 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./
National Pesticide Information Retrieval System's USEPA/OPP Chemical Ingredients Database on Pinoxaden (243973-20-8). Available from, as of January 5, 2011: https://npirspublic.ceris.purdue.edu/ppis/
Herbicides (phenylpyrazole herbicides)
Alan Wood; Compendium of Pesticide Common Names, Pinoxaden. Available from, as of February 5, 2011: https://www.alanwood.net/pesticides/pinoxaden.html
Herbicide
Meister, R.T., Sine, C; Crop Protection Handbook Volume 94. Meister Media Worldwide, Willoughby, OH 2008, p. D 349
For use in barley and spring and winter wheat. Not for use on durum wheat.
Crop Protection Handbook Volume 96, Meister Media Worldwide, Willoughby, OH 2010, p. 516

9.1.1 Use Classification

Herbicides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688
Environmental transformation -> Pesticides (parent, predecessor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759

9.2 Methods of Manufacturing

Pinoxaden can be produced by condensation of 2-6-diethyl-4-methylphenylacetic tert-butylanhydride, hydrazine, and diethylene glycol.
Muller F and Appleby AP; Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (2010). NY, NY: John Wiley & Sons; Weed Control, 2. Individual Herbicides. Online Posting Date: September 15, 2010

9.3 Formulations / Preparations

Emulsifiable concentrate
Crop Protection Handbook Volume 96, Meister Media Worldwide, Willoughby, OH 2010, p. 516
PREMIX PARTNERS: Florasulam
Crop Protection Handbook Volume 96, Meister Media Worldwide, Willoughby, OH 2010, p. 516
Axial XL (Syngenta Crop Protection, LLC.) 5.05% Pinoxaden
Purdue University; National Pesticide Information Retrieval System, Pinoxaden PC Code: 147500. Available from, as of January 25, 2011: https://npirspublic.ceris.purdue.edu/ppis/
Axial Herbicide (Syngenta Crop Protection, LLC.) 9.71% Pinoxaden
Purdue University; National Pesticide Information Retrieval System, Pinoxaden PC Code: 147500. Available from, as of January 25, 2011: https://npirspublic.ceris.purdue.edu/ppis/
For more Formulations/Preparations (Complete) data for Pinoxaden (6 total), please visit the HSDB record page.

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 3
View All
Pictogram(s)
Irritant
Health Hazard
Environmental Hazard
Signal
Warning
GHS Hazard Statements

H302+H332 (55%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]

H302 (72.7%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (22.5%): Causes skin irritation [Warning Skin corrosion/irritation]

H317 (81.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H361 (17.7%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

H361d (55%): Suspected of damaging the unborn child [Warning Reproductive toxicity]

H400 (72.7%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (31.1%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

H412 (80.4%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P203, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 209 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Acute Tox. 4 (72.7%)

Skin Irrit. 2 (22.5%)

Skin Sens. 1B (81.8%)

Eye Irrit. 2 (100%)

Acute Tox. 4 (100%)

STOT SE 3 (100%)

Repr. 2 (17.7%)

Repr. 2 (55%)

Aquatic Acute 1 (72.7%)

Aquatic Chronic 1 (31.1%)

Aquatic Chronic 3 (80.4%)

Reproductive toxicity - category 2

Acute toxicity (inhalation) - category 4

Acute toxicity (ingestion) - category 4

Eye irritation - category 2

Specific target organ toxicity (single exposure) - category 3

Skin sensitisation - category 1A

Hazardous to the aquatic environment (acute) - category 1

Hazardous to the aquatic environment (chronic) - category 3

10.2 Fire Fighting

10.2.1 Fire Fighting Procedures

Use appropriate extinguishing media for combustibles in the area. Wear full protective clothing and self-contained breathing apparatus. Evacuate nonessential personnel from the area to prevent human exposure to fire, smoke, fumes or products of combustion. Prevent use of contaminated buildings, area, and equipment until decontaminated. Water runoff can cause environmental damage. If water is used to fight fire, dike and collect runoff. /Axial Herbicide/
Syngenta Crop Protection, Inc; MSDS, Axial Herbicide (January 20, 2011). Available from, as of February 10, 2011: https://www.syngentacropprotection.com/pdf/msds/03_263831202011.pdf
Combustible liquid. Can release vapors that form explosive mixtures at temperatures at or above the flash point. Heavy vapors can flow along surfaces to distant ignition sources and flash back. /Axial Herbicide/
Syngenta Crop Protection, Inc; MSDS, Axial Herbicide (January 20, 2011). Available from, as of February 10, 2011: https://www.syngentacropprotection.com/pdf/msds/03_263831202011.pdf
During a fire, irritating and possibly toxic gases may be generated by thermal decomposition or combustion. /Axial Herbicide/
Syngenta Crop Protection, Inc; MSDS, Axial Herbicide (January 20, 2011). Available from, as of February 10, 2011: https://www.syngentacropprotection.com/pdf/msds/03_263831202011.pdf

10.3 Accidental Release Measures

10.3.1 Cleanup Methods

Do not contaminate water when disposing of equipment wash water or rinsate. /Axial Herbicide/
Syngenta Crop Protection, Inc; Product Label for Axial Herbicide (2008). Available from, as of February 10, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP1199AL1C0308nn.pdf
ACCIDENTAL RELEASE MEASURES. Control the spill at its source. Contain the spill to prevent from spreading or contaminating soil or from entering sewage and drainage systems or any body of water. Clean up spills immediately, observing precautions outlined in Section 8. Cover entire spill with absorbing material and place into compatible disposal container. Scrub area with hard water detergent (e.g. commercial products such as Tide, Joy, Spic and Span). Pick up wash liquid with additional absorbent and place into compatible disposal container. Once all material is cleaned up and placed in a disposal container, seal container and arrange for disposition. /Axial Herbicide/
Syngenta Crop Protection, Inc; MSDS, Axial Herbicide (January 20, 2011). Available from, as of February 10, 2011: https://www.syngentacropprotection.com/pdf/msds/03_263831202011.pdf
If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label./Residential users/
USEPA/Prevention, Pesticides, and Toxic Substances; Citizen's Guide to Pest Control and Pesticide Safety p.20 (March 2005) EPA 730-K-04-002
After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide. To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash. /Residential users/
USEPA/Prevention, Pesticides, and Toxic Substances; Citizen's Guide to Pest Control and Pesticide Safety p.22 (March 2005) EPA 730-K-04-002

10.3.2 Disposal Methods

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: Pesticide wastes are toxic. Improper disposal of excess pesticides, spray mixture, or rinsate is a violation of Federal law. If these wastes cannot be disposed of by use according to label instructions, contact your State Pesticide or Environmental Control Agency, or the Hazardous Waste representative at the nearest EPA Regional Office for guidance. /Axial Herbicide/
Syngenta Crop Protection, Inc; Product Label for Axial Herbicide (2008). Available from, as of February 10, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP1199AL1C0308nn.pdf
Container Disposal: Do not reuse empty container. Triple rinse (or equivalent). Then offer for recycling or reconditioning, or puncture and dispose of in a sanitary landfill, or incineration, or, if allowed by state and local authorities, by burning. If burned, stay out of smoke. /Axial Herbicide/
Syngenta Crop Protection, Inc; Product Label for Axial Herbicide (2008). Available from, as of February 10, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP1199AL1C0308nn.pdf
Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal. /Residential users/
USEPA/Prevention, Pesticides, and Toxic Substances; Citizen's Guide to Pest Control and Pesticide Safety p.24 (March 2005) EPA 730-K-04-002
Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it. /Residential users/
USEPA/Prevention, Pesticides, and Toxic Substances; Citizen's Guide to Pest Control and Pesticide Safety p.25 (March 2005) EPA 730-K-04-002

10.3.3 Preventive Measures

Use this product only in accordance with its labelling and with the Worker Protection Standard, 40 CFR part 170. /Axial Herbicide/
Syngenta Crop Protection, Inc; Product Label for Axial Herbicide (2008). Available from, as of February 10, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP1199AL1C0308nn.pdf
If in eyes: Hold eye open and rinse slowly and gently with water for 15-20 minutes. Remove contact lenses, if present after the first 5 minutes, then continue rinsing eye. Call a poison control center or doctor for treatment advice. /Axial Herbicide/
Syngenta Crop Protection, Inc; Product Label for Axial Herbicide (2008). Available from, as of February 10, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP1199AL1C0308nn.pdf
If on skin or clothing: Take off contaminated clothing. Rinse skin immediately with plenty of water for 15-20 minutes. Call a poison control center or doctor for treatment advice. /Axial Herbicide/
Syngenta Crop Protection, Inc; Product Label for Axial Herbicide (2008). Available from, as of February 10, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP1199AL1C0308nn.pdf
If swallowed: Immediately call a poison control center or doctor. Do not induce vomiting unless told to do so by a poison control center or doctor. Do not give any liquid to the person. Do not give anything by mouth to an unconscious person. /Axial Herbicide/
Syngenta Crop Protection, Inc; Product Label for Axial Herbicide (2008). Available from, as of February 10, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP1199AL1C0308nn.pdf
For more Preventive Measures (Complete) data for Pinoxaden (17 total), please visit the HSDB record page.

10.4 Handling and Storage

10.4.1 Storage Conditions

Store in a cool, dry place. Do not store near seeds, fertilizers, or foodstuffs. /Axial Herbicide/
Syngenta Crop Protection, Inc; Product Label for Axial Herbicide (2008). Available from, as of February 10, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP1199AL1C0308nn.pdf
MaxImum Storage Temp: 95 °F (35 °C) Minimum Storage Temp: 14 °F (-10 °C). Store the material in a well-ventilated, secure area out of reach of children and domestic animals. Do not store food, beverages or tobacco products in the storage area. Prevent eating, drinking, tobacco use, and cosmetic application in areas where there is a potential for exposure to the material. Wash thoroughly with soap and water after handling. /Axial Herbicide/
Syngenta Crop Protection, Inc; MSDS, Axial Herbicide (January 20, 2011). Available from, as of February 10, 2011: https://www.syngentacropprotection.com/pdf/msds/03_263831202011.pdf
Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water. /Residential users/
USEPA/Prevention, Pesticides, and Toxic Substances; Citizen's Guide to Pest Control and Pesticide Safety p.23 (March 2005) EPA 730-K-04-002

10.5 Exposure Control and Personal Protection

10.5.1 Allowable Tolerances

Tolerances are established for the combined residues of pinoxaden (8-(2,6-diethyl-4-methylphenyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo[1,2-d][1,4,5] oxadiazepin-9-yl 2,2-dimethylpropanoate), and its metabolites 8-(2,6-diethyl-4-methyl-phenyl)-tetrahydro-pyrazolo[1,2-d][1,4,5]oxadiazepine-7,9-dione (M2), and free and conjugated forms of 8-(2,6-diethyl-4-hydroxymethyl-phenyl)-tetrahydro-pyrazolo[1,2-d][1,4,5] oxadiazepine-7,9-dione (M4), and 4-(7,9-dioxo-hexahydro-pyrazolo[1,2-d] [1,4,5]oxadiazepin-8-yl)-3,5-diethyl-benzoic acid (M6), calculated as pinoxaden, in/on the following commodities:
Commodity
Barley, bran
Parts per million
1.6
Commodity
Barley, grain
Parts per million
0.9
Commodity
Barley, hay
Parts per million
1.5
Commodity
Barley, straw
Parts per million
1.0
Commodity
Egg
Parts per million
0.06
Commodity
Poultry, fat
Parts per million
0.06
Commodity
Poultry, meat
Parts per million
0.06
Commodity
Poultry, meat byproducts
Parts per million
0.06
Commodity
Wheat, bran
Parts per million
3.0
Commodity
Wheat, forage
Parts per million
3.5
Commodity
Wheat, grain
Parts per million
1.3
Commodity
Wheat, hay
Parts per million
2.0
Commodity
Wheat, straw
Parts per million
1.5
40 CFR 180.611(a) (1) (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of January 4, 2011: https://www.ecfr.gov
For the combined residues of pinoxaden, 8-(2,6-diethyl-4-methylphenyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo[1,2-d][1,4,5] oxadiazepin-9-yl 2,2-dimethylpropanoate), and its metabolites M2, 8-(2,6-diethyl-4-methyl-phenyl)-tetrahydro-pyrazolo[1,2-d][1,4,5]oxadiazepine-7,9-dione, and free and conjugated forms of M4, 8-(2,6-diethyl-4-hydroxymethyl-phenyl)-tetrahydro-pyrazolo[1,2-d][1,4,5] oxadiazepine-7,9-dione, calculated as pinoxaden, in/on the following commodities:
Commodity
Cattle, fat
Parts per million
0.04
Commodity
Cattle, meat
Parts per million
0.04
Commodity
Cattle, meat byproducts
Parts per million
0.04
Commodity
Milk
Parts per million
0.02
40 CFR 180.611(a) (2) (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of January 4, 2011: https://www.ecfr.gov

10.5.2 Personal Protective Equipment (PPE)

Applicators and other handlers must wear: Long-sleeved shirt and long pants. Shoes plus socks. Chemical-resistant gloves, Category A, such as barrier laminate, butyl rubber greater than or equal to 14 mils, nitrile rubber 14 mils, neoprene rubber greater than or equal to 14 mils, polyethylene, polyvinyl chloride (PVC) greater than or equal to 14 mils, or viton 14 mils. /Axial Herbicide/
Syngenta Crop Protection, Inc; Product Label for Axial Herbicide (2008). Available from, as of February 10, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP1199AL1C0308nn.pdf
... Restricted-entry interval (REI) of 48 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. Shoes plus socks. Chemical-resistant gloves, Category A, such as barrier laminate, butyl rubber greater than or equal to 14 mils, nitrile rubber greater than or equal to 14 mils, neoprene rubber greater than or equal to 14 mils, polyethylene, polyvinyl chloride (PVC) greater than or equal to 14 mils, or viton greater than or equal to 14 mils. /Axial Herbicide/
Syngenta Crop Protection, Inc; Product Label for Axial Herbicide (2008). Available from, as of February 10, 2011: https://www.syngentacropprotection.com/pdf/labels/SCP1199AL1C0308nn.pdf

10.6 Regulatory Information

Status Regulation (EC)
2005/459/EC, 2012/191/EU, Reg. (EU) 2016/370, Reg. (EU) No 289/2014, Reg. (EU) No 540/2011
New Zealand EPA Inventory of Chemical Status
Pinoxaden: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

10.6.1 FIFRA Requirements

Tolerances are established for the combined residues of pinoxaden (8-(2,6-diethyl-4-methylphenyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo[1,2-d][1,4,5] oxadiazepin-9-yl 2,2-dimethylpropanoate), and its metabolites 8-(2,6-diethyl-4-methyl-phenyl)-tetrahydro-pyrazolo[1,2-d][1,4,5]oxadiazepine-7,9-dione (M2), and free and conjugated forms of 8-(2,6-diethyl-4-hydroxymethyl-phenyl)-tetrahydro-pyrazolo[1,2-d][1,4,5] oxadiazepine-7,9-dione (M4), and 4-(7,9-dioxo-hexahydro-pyrazolo[1,2-d] [1,4,5]oxadiazepin-8-yl)-3,5-diethyl-benzoic acid (M6), calculated as pinoxaden, in/on the following commodities:
Commodity
Barley, bran
Commodity
Barley, grain
Commodity
Barley, hay
Commodity
Barley, straw
Commodity
Egg
Commodity
Poultry, fat
Commodity
Poultry, meat
Commodity
Poultry, meat byproducts
Commodity
Wheat, bran
Commodity
Wheat, forage
Commodity
Wheat, grain
Commodity
Wheat, hay
Commodity
Wheat, straw
40 CFR 180.611(a) (1) (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of January 4, 2011: https://www.ecfr.gov
For the combined residues of pinoxaden, 8-(2,6-diethyl-4-methylphenyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo[1,2-d][1,4,5] oxadiazepin-9-yl 2,2-dimethylpropanoate), and its metabolites M2, 8-(2,6-diethyl-4-methyl-phenyl)-tetrahydro-pyrazolo[1,2-d][1,4,5]oxadiazepine-7,9-dione, and free and conjugated forms of M4, 8-(2,6-diethyl-4-hydroxymethyl-phenyl)-tetrahydro-pyrazolo[1,2-d][1,4,5] oxadiazepine-7,9-dione, calculated as pinoxaden, in/on the following commodities:
Commodity
Cattle, fat
Commodity
Cattle, meat
Commodity
Cattle, meat byproducts
Commodity
Milk
40 CFR 180.611(a) (2) (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of January 4, 2011: https://www.ecfr.gov

11 Toxicity

11.1 Toxicological Information

11.1.1 RAIS Toxicity Values

Oral Acute Reference Dose (RfDoa)(mg/kg-day)
0.3
Oral Acute Reference Dose Reference
OPP
Oral Chronic Reference Dose (RfDoc) (mg/kg-day)
0.3
Oral Chronic Reference Dose Reference
OPP

11.1.2 EPA Human Health Benchmarks for Pesticides

Chemical Substance
Acute or One Day PAD (RfD) [mg/kg/day]
0.3
Acute or One Day HHBPs [ppb]
8000
Acute HHBP Sensitive Lifestage/Population
Females 13-49 yrs
Chronic or One Day PAD (RfD) [mg/kg/day]
0.3
Chronic or One Day HHBPs [ppb]
2000
Chronic HHBP Sensitive Lifestage/Population
General Population

11.1.3 Antidote and Emergency Treatment

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 0.9% saline (NS) 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 ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160-1

11.1.4 Human Toxicity Excerpts

/GENOTOXICITY/ In two independent trials of a mammalian cell cytogenetics assay, lymphocyte cultures were prepared from human peripheral blood and exposed to SYN 502836 (a metabolite of Pinoxaden tech.; pinoxaden; 99% a.i., Batch # KI 6513/3M) in dimethylsulfoxide (DMSO) at concentrations of 50, 100, 200, 500, 1000, 1500, 2000, and 2750 ug/mL for either 3 hours with a 17 hour recovery period (Trial 1, +/-S9 and Trial 2, +S9) or 20 hours with no recovery period (Trial 2, -S9). SYN 502836 was tested up to a maximum concentration of 2000 ug/mL (+/-S9), which was limited by reductions in the pH of the treatment medium. Cytotoxicity (as evidenced by reduced mitotic index) was noted at greater than or equal to 1000 ug/mL in Trial 1 (+S9) and at 2000 ug/mL in Trial 2 (+/-S9). No significant increases in aberration frequencies (excluding gaps) were observed in the presence or absence of S9 in either trial. The positive controls induced the appropriate response in all assays. There was no evidence of chromosome aberrations induced over background in the presence or absence of S9-activation. /SYN 502836/
USEPA; Pinoxaden: Human Health Risk Assessment.p.72 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf

11.1.5 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ 5/sex/dose Wistar rats (Age: 8 weeks, Weight: 185.9-199.4 g males, 162.6-176.8 g females) were given a single oral dose of pinoxaden technical(Propanoic acid: 97.2%; Batch #: EZ005006; beige solid) or a control dose of 0.5% w/v carboxymethylcellulose in 0.1% w/v polysorbate 80 by oral gavage. The study was performed at a limit dose of either 5,000 mg/kg or 0 mg/kg (control). Individual animal body-weights were recorded prior to dosing, and again on days 7 and 14. Clinical signs of toxicity were made several times post-dosing on the initial study day and daily thereafter for 14 days. All animals were necropsied on study day 14 or immediately after death. ... All control animals survived, gained weight and appeared healthy during the study. No gross internal findings were observed at necropsy. For those animals dosed at 5,000 mg/kg clinical signs of toxicity noted included slight soft feces and hunched posture, but animals recovered from these symptoms by day 1 of the study. One male was found dead on day 5 post-dosing. Gross necropsy of this animal revealed reddish small and large intestines and a reddish caecum. The surviving animals all gained weight during the study and had no gross internal findings at necropsy.
USEPA; Pinoxaden: Human Health Risk Assessment.p.59 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf
/LABORATORY ANIMALS: Acute Exposure/ In an acute inhalation toxicity study, 15/sex//dose Wistar rats (Age: 8-11 weeks; Weight: 237.8-260.3 g males; 190.4-220.9 g females) were exposed via nose-only, flow-past inhalation to pinoxaden technical(Propanoic acid: 97.2%; Batch #: EZ005006; solid) for 4 hours at analytically determined concentrations of either 2.249, 3.793 or 5.454 mg/L. The test was initiated at a concentration of 5.454 mg/L, but due to death in 50% of test animals, the dose was lowered to 2.249 mg/L. Based on the lack of deaths at this concentration the dose was raised to 3.793 mg/L in order to measure the LC50. Individual body-weights were recorded prior to testing and on days 4, 8 and 15. The animals were observed for clinical signs of toxicity and mortality once per hour during the aerosol exposure period, after exposure and at least once a day thereafter for 15 days or until death. A gross necropsy examination was performed on all the animals on day 15 or when found dead. ... For those animals dosed at 2.249 mg/L, all survived the study. Clinical signs of toxicity noted during and/or after exposure included laboured respiration, rales (breath sounds), salivation, ruffled fur, hunched posture and red secretion from the nose (in one animal). Symptoms of toxicity persisted until day 7 after exposure. The mean body-weight of the animals decreased during the first 4 days of the study but increased thereafter, exceeding their initial body-weight by the end of the study. Red discolouration of the lymph nodes was observed in two test animals at necropsy. No gross necropsy findings were found for the other test animals. For those animals dosed at 3.793 mg/L, all survived the exposure period. 3/10 animals were found dead 2 days after the exposure period. Clinical signs of toxicity noted during and/or after exposure included tachypnea, laboured respiration, rales (breath sounds), salivation, ruffled fur, hunched posture, restlessness and decreased activity. In one female a swollen abdomen was also observed. Symptoms of toxicity persisted until day 7 after exposure. The mean body-weight of the surviving animals decreased during the first 4 days of the study but increased thereafter, exceeding their initial body-weight by the end of the study. Red discolouration of the lungs was observed at necropsy in 2/3 of the test animals that died during the study. No gross necropsy findings were found for the other test animals. For those animals dosed at 5.454 mg/L, all survived the exposure period. 4/10 animals were found dead the day after the exposure period. A fifth animal was found dead 3 days after the exposure period. Clinical signs of toxicity noted during and/or after exposure included bradypnea, laboured respiration, rales (breath sounds), salivation, ruffled fur, hunched posture, restlessness and decreased activity. Symptoms of toxicity persisted up to day 7 after exposure. The mean body-weight of the surviving animals decreased during the first 4 days of the study but increased thereafter. Males exceeded their initial body-weight by the end of the study while females exceeded their initial body-weight. Red discolouration of the lungs was observed at necropsy in 4/5 of the test animals that died during the study. The other test animal that died had several dark red foci in the thymus at necropsy. One surviving animal had incompletely collapsed lungs at necropsy. No gross necropsy findings were found for the other test animals.
USEPA; Pinoxaden: Human Health Risk Assessment.p.60-1 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf
/LABORATORY ANIMALS: Acute Exposure/ In a dermal sensitization study with pinoxaden technical(Propanoic acid: 97.2%; Batch #: EZ005006; solid), 15/sex (5/sex for control and 10/sex for test) Himalayan spotted guinea pigs (Weight: 309-376 g males, 298-403 g females) were tested using the Magnusson-Kligman Design method. During the preliminary testing phase, appropriate concentrations of the test substance to be used were determined for the intradermal induction (test substance at 5% in vehicle (0.5% carboxymethylcellulose + 0.1% Tween 80 in bi-distilled water)), topical induction (test substance at 50 % in vehicle), and topical challenge (test substance at 50 % in vehicle). The first induction phase involved 3, 0.1 mL intradermal paired injections into 20 guinea pigs of the test substance (test substance at 5% in vehicle), test substance and Freund's Adjuvant, and Adjuvant alone. Paired injections were also administered to 10 control guinea pigs of the vehicle, vehicle with Freund's Adjuvant, and Adjuvant alone. One week later, a second induction phase was conducted consisting of a 0.3 mL topical application of the test substance at 50 % in vehicle applied to a patch of filter paper and placed on the dose site of the test animals, which was then covered for 48 hours. Twenty-four and 48 hours after patch removal the animals were scored for erythema. The control group was treated in the same manner with vehicle only. Twenty-three hours prior to this phase the animals were treated with 0.5 mL of 10% sodium lauryl sulfate to provoke a mild inflammatory reaction. Two weeks after the topical application of the induction phase the challenge phase was conducted by applying 0.2 g of a topical application of the test substance at 50 % in vehicle on the left flank, and 0.2 mL of vehicle only on the right flank, to both the test and control guinea pigs for 24 hours. Twenty-four and 48 hours after patch removal the animals were scored for erythema. Observations for clinical signs of toxicity and mortality occurred daily. The procedures were validated using 2-Mercaptobenzothiazole as the positive control substance. Based on this study, pinoxaden technical is not a dermal sensitizer ... . During the induction phase, observations at all dose sites for test animals treated with the test substance during the topical application phases revealed discrete/patchy erythema (score 1) at 24 hours and in 18/19 animals at 48 hours. This reaction was also noted in the control animals at 24 and 48 hours after treatment with vehicle only. One test male died on test day 10 after removal of the dressing in the topical induction phase. Gross necropsy of this animal revealed no internal findings. At challenge no skin reactions were noted for either the test or the control animals.
USEPA; Pinoxaden: Human Health Risk Assessment.p.63 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf
/LABORATORY ANIMALS: Acute Exposure/ In a primary dermal irritation study, 3 young adult New Zealand albino rabbits (1 male, 2 females) were dermally exposed to 0.5 g of pinoxaden technical(Propanoic acid: 97.2%; Batch #: EZ005006; solid). The test substance was moistened with 0.1 mL of bi-distilled water, placed on a 6 sq cm area of a gauze pad, applied to the left flank on each animal and secured with a semi-occlusive wrap for 4 hours. Animals were then observed for 72 hours. Dermal irritation was scored according to the Draize system at 1, 24, 48 and 72 hours post-patch removal. Observations for clinical signs of toxicity and mortality occurred daily. In this study, the formulation is non-irritating to the skin. Pinoxaden technicalis classified as EPA Toxicity Category IV. No erythema or edema were noted at any point during the study.
USEPA; Pinoxaden: Human Health Risk Assessment.p.62 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf
For more Non-Human Toxicity Excerpts (Complete) data for Pinoxaden (32 total), please visit the HSDB record page.

11.1.6 Non-Human Toxicity Values

LD50 Rat dermal > 2,000 mg/kg
USEPA; Pinoxaden: Human Health Risk Assessment.p.60 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf
LD50 Rat oral > 5,000 mg/kg
USEPA; Pinoxaden: Human Health Risk Assessment.p.59 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf
LC50 Rat (combined male and female) inhalation 5.22 mg/L/4 hr (95% Confidence Limits: 4.07 -18.00 mg/l air)
USEPA; Pinoxaden: Human Health Risk Assessment.p.60 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf
LC50 Rat (female) inhalation 6.24 mg/L/4 hr (No Confidence Limits calculated)
USEPA; Pinoxaden: Human Health Risk Assessment.p.60 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf
LC50 Rat (male) inhalation 4.63 mg/L/4 hr (80% Confidence Limits: 3.35 - 20.68 mg/l air)
USEPA; Pinoxaden: Human Health Risk Assessment.p.60 (July 13, 2005). Available from, as of February 10, 2011: https://www.epa.gov/opprd001/factsheets/humanhealth_pinoxaden.pdf

11.2 Ecological Information

11.2.1 EPA Ecotoxicity

Pesticide Ecotoxicity Data from EPA

11.2.2 Environmental Fate / Exposure Summary

Pinoxaden's production may result in its release to the environment through various waste streams; its use as a herbicide will result in its direct release to the environment. If released to air, a vapor pressure of 3.5X10-9 mm Hg at 25 °C indicates pinoxaden will exist solely in the particulate phase in the atmosphere. Particulate-phase pinoxaden will be removed from the atmosphere by wet or dry deposition. If released to soil, pinoxaden is expected to have moderate to high mobility based upon a Koc range of 852 to 121. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 9.1X10-12 atm-cu m/mole. Pinoxaden biodegrades rapidly with an aerobic half-life of 2 to 3 days in soil and an aerobic half-life of <1 day in water. If released into water, pinoxaden is expected to adsorb to suspended solids and sediment based upon the Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 60 suggests the potential for bioconcentration in aquatic organisms is moderate. Pinoxaden hydrolysis half-lives are reported as 24.1, 25.3, 14.9 and 0.3 days at pH 4, 5, 7 and 9, respectively. Occupational exposure to pinoxaden may occur through inhalation and dermal contact with this compound at workplaces where pinoxaden is produced or used. (SRC)

11.2.3 Artificial Pollution Sources

Pinoxaden's production may result in its release to the environment through various waste streams; its use as a herbicide(1) will result in its direct release to the environment(SRC).
(1) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)

11.2.4 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value range of 852 to 121(2), indicates that pinoxaden is expected to have moderate to high mobility in soil(SRC). Volatilization of pinoxaden from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.1X10-12 atm-cu m/mole(SRC), based upon its vapor pressure, 3.5X10-9 mm Hg(2), and water solubility, 200 mg/L(2). Pinoxaden is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Pinoxaden biodegrades rapidly with an aerobic half-life of 2 to 3 days in soil(3).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)
(3) US EPA; Pesticide Fact Sheet. Pinoxaden. July 2005. US EPA, Off Prevt Pest Tox Sub (7501C). Available from, as of Feb 24, 2011: https://www.epa.gov/opprd001/factsheets/pinoxaden.pdf
AQUATIC FATE: Based on a classification scheme(1), a Koc value range of 121 to 852(2), indicates that pinoxaden is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 9.1X10-12 atm-cu m/mole(SRC), derived from its vapor pressure, 3.5X10-9 mm Hg(2), and water solubility, 200 mg/L(2). According to a classification scheme(4), an estimated BCF of 60(SRC), from its log Kow of 3.2(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Pinoxaden hydrolysis half-lives are reported as 24.1, 25.3, 14.9 and 0.3 days at pH 4, 5, 7 and 9, respectively(2). Pinoxaden degrades rapidly with an aerobic aquatic half-life of <1 day(6).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(4) Franke C et al; Chemosphere 29: 1501-14 (1994)
(5) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(6) US EPA; Pesticide Fact Sheet. Pinoxaden. July 2005. US EPA, Off Prevt Pest Tox Sub (7501C). Available from, as of Feb 24, 2011: https://www.epa.gov/opprd001/factsheets/pinoxaden.pdf
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pinoxaden, which has a vapor pressure of 3.5X10-9 Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase pinoxaden may be removed from the air by wet or dry deposition(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)

11.2.5 Environmental Biodegradation

AEROBIC: Pinoxaden degrades rapidly with a half-life of <1 day in aerobic aquatic conditions and a half-life of 2 to 3 days in soil(1).
(1) US EPA; Pesticide Fact Sheet. Pinoxaden. July 2005. US EPA, Off Prevt Pest Tox Sub (7501C). Available from, as of Feb 24, 2011: https://www.epa.gov/opprd001/factsheets/pinoxaden.pdf

11.2.6 Environmental Abiotic Degradation

Pinoxaden hydrolysis half-lives are reported as 24.1, 25.3, 14.9 and 0.3 days at pH 4, 5, 7 and 9, respectively(1).
(1) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)

11.2.7 Environmental Bioconcentration

An estimated BCF of 60 was calculated in fish for pinoxaden(SRC), using a log Kow of 3.2(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).
(1) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)
(2) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

11.2.8 Soil Adsorption / Mobility

The Koc of pinoxaden has been reported to be 852 to 121(1). According to a classification scheme(2), this Koc value range suggests that pinoxaden is expected to have moderate to high mobility in soil.
(1) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)
(2) Swann RL et al; Res Rev 85: 17-28 (1983)

11.2.9 Volatilization from Water / Soil

The Henry's Law constant for pinoxaden is estimated as 9.1X10-12 atm-cu m/mole(SRC) derived from its vapor pressure, 3.5X10-9 mm Hg(1), and water solubility, 200 mg/L(1). This Henry's Law constant indicates that pinoxaden is expected to be essentially nonvolatile from water surfaces(2). Pinoxaden is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
(1) MacBean C, ed; e-Pesticide Manual. 15th ed., ver. 5.1, Alton, UK; British Crop Protection Council. Pinoxaden (243973-20-8) (2008-2010)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)

11.2.10 Probable Routes of Human Exposure

Occupational exposure to pinoxaden may occur through inhalation and dermal contact with this compound at workplaces where pinoxaden is produced or used. (SRC)

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Chemical Co-Occurrences in Literature

12.6 Chemical-Gene Co-Occurrences in Literature

12.7 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Biological Test Results

14.1 BioAssay Results

15 Classification

15.1 MeSH Tree

15.2 ChEBI Ontology

15.3 ChemIDplus

15.4 UN GHS Classification

15.5 NORMAN Suspect List Exchange Classification

15.6 EPA DSSTox Classification

15.7 EPA Substance Registry Services Tree

15.8 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. EPA Safe Drinking Water Act (SDWA)
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    pinoxaden (ISO); 8-(2,6-diethyl-4-methylphenyl)-7-oxo-1,2,4,5-tetrahydro-7H-pyrazolo[1,2-d][1,4,5]oxadiazepin-9-yl 2,2-dimethylpropanoate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.163.258
    pinoxaden (ISO); 8-(2,6-diethyl-4-methylphenyl)-7-oxo-1,2,4,5-tetrahydro-7H-pyrazolo[1,2-d][1,4,5]oxadiazepin-9-yl 2,2-dimethylpropanoate (EC: 635-361-9)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/168079
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Hazardous Substances Data Bank (HSDB)
  8. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  9. Risk Assessment Information System (RAIS)
    LICENSE
    This work has been sponsored by the U.S. Department of Energy (DOE), Office of Environmental Management, Oak Ridge Operations (ORO) Office through a joint collaboration between United Cleanup Oak Ridge LLC (UCOR), Oak Ridge National Laboratory (ORNL), and The University of Tennessee, Ecology and Evolutionary Biology, The Institute for Environmental Modeling (TIEM). All rights reserved.
    https://rais.ornl.gov/
  10. ChEBI
  11. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  12. EPA Pesticide Ecotoxicity Database
  13. EU Pesticides Database
  14. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Pinoxaden
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  15. USDA Pesticide Data Program
  16. Hazardous Chemical Information System (HCIS), Safe Work Australia
  17. Regulation (EC) No 1272/2008 of the European Parliament and of the Council
    LICENSE
    The copyright for the editorial content of this source, the summaries of EU legislation and the consolidated texts, which is owned by the EU, is licensed under the Creative Commons Attribution 4.0 International licence.
    https://eur-lex.europa.eu/content/legal-notice/legal-notice.html
  18. Japan Chemical Substance Dictionary (Nikkaji)
  19. MassBank Europe
  20. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  21. Metabolomics Workbench
  22. Springer Nature
  23. The Cambridge Structural Database
  24. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  25. Wikidata
  26. PubChem
  27. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  28. GHS Classification (UNECE)
  29. EPA Substance Registry Services
  30. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  31. PATENTSCOPE (WIPO)
CONTENTS