Profoxydim (Ref: BAS 625H)

Profoxydim (Ref: BAS 625H)	Last updated: 12/01/2021
(Also known as: clefoxydim; clefoxidim)

SUMMARY

Profoxydim is an EU approved, post-emergence rice herbicide. It has a low aqueous solubility, is volatile and does not present a risk of leaching to groundwater. It is non-persistent in soil but can be persistent in water. It has a low mammalian toxicity and the risk of bioaccumulation is low. No other serious human health risks have been identified. It shows a low to moderate toxicity to birds, aquatic organisms, honeybees and earthworms.

GENERAL INFORMATION

Description

Used for the post-emergence control of grass weeds in rice

Example pests controlled

Barnyard grass; Silvertop grass; Giant reed (Arundo donax); Crab grass; Yellow bristlegrass

Example applications

Rice

Efficacy & activity

Availability status

Current

Introduction & key dates

1998

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Spain/Greece

Date EC 1107/2009 inclusion expires

31/07/2021

EU Candidate for substitution (CfS)

Yes - endocrine disrupting properties

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece
								✓
ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg
✓						✓
LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia
				✓

Also used in

Chemical structure

Isomerism

A chiral molecule existing in both the E- and Z-forms

Chemical formula

C₂₄H₃₂ClNO₄S

Canonical SMILES

CCCC(=C1C(=O)CC(CC1=O)C2CCCSC2)NOCC(C)OC3=CC=C(C=C3)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

NZYQPWCHQXECMD-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C24H32ClNO4S/c1-3-5-21(26-29-14-16(2)30-20-9-7-19(25)8-10-20)24-22(27)12-18(13-23(24)28)17-6-4-11-31-15-17/h7-10,16-18,26H,3-6,11-15H2,1-2H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Cyclohexadione

Minimum active substance purity

>940 g kg⁻¹

Known relevant impurities

Substance origin

Synthetic

Mode of action

Selective in rice, inhibiting weed growth, ACCase inhibitor.

CAS RN

139001-49-3

EC number

CIPAC number

621

US EPA chemical code

121007

PubChem CID

197395

Molecular mass

466.03

PIN (Preferred Identification Name)

(5E)-2-{(1E)-N-[(2E)-2-(4-chlorophenoxy)propoxy]butanimidoyl}-3-hydroxy-5-[(3?)-thian-3-yl]cyclohex-2-en-1-one

IUPAC name

(5RS)-2-{(EZ)-1-[(2RS)-2-(4-chlorophenoxy)propoxyimino]butyl}-3-hydroxy-5-[(3RS)-thian-3-yl]cyclohex-2-en-1-one

CAS name

2-[1-[[2-(4-chlorophenoxy)propoxy]imino]butyl]-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen-1-one

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Leptochloa chinensis

Physical state

Colourless liquid

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Aura

Example products using this active

BASF

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

27.8

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

1900000

Acetone

1700000

Ethyl acetate

480000

Methanol

1300000

Toluene

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

150

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

Octanol-water partition coefficient at pH 7, 20 °C

7.94 X 10⁰³

Calculated

Log P

3.9

High

Bulk density (g ml⁻¹)

1.198

Dissociation constant pKa) at 25 °C

5.91

Weak acid

Vapour pressure at 20 °C (mPa)

0.17

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

0.0176

Non-volatile

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Max @ 300nm

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

21.5

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dosiser Lab DT₅₀ range 3-13 days, DT₉₀ 2-41days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

140

Persistent

Note

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

11.49

Slightly mobile

K_foc

3032

¹/_n

1.01

Notes and range

EU dossier K_f range 2.04-20.94 mL g⁻¹; K_foc range 81-5983 mL g⁻¹, ¹/_n range 0.92-1.1, soils-6

pH sensitivity

Yes, higher Koc values for lower pH values.

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.47

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

7.25 X 10^-03

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

Ref: BH 625-1
Note: DT50 soil= 185-374 days; Koc= 24-1749 mL/g

Soil

0.731

Ref: BH 625-10
Note: DT50 soil= 239-318 days; Koc= 89-6585 mL/g

Soil

0.155

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

1.85

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

3.13

Oncorhynchus mykiss 28 day

Moderate

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

18.1

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

10.9

Daphnia magna

Low

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

> 29.4

Lemna gibba

Low

Non-target plants

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

Anabaena flos-aquae

Low

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

18.1

Unknown species

Low

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 200

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 200

Low

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other pollinators (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other pollinators (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 1000

Eisenia foetida

Low

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

70.53

Mortality
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

50.6

Mortality
Typhlodromus pyri

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 5x field rate

Mesocosm study data

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

4000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.2

Rat

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.005

Rat SF=1000

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.05

Rat SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.025

Dog SF=100

Dermal penetration studies (%)

1.5

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Liver toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H317, H351, H361d

EC Risk Classification

Carcinogen category 3: R40
Reproduction risk category 3: R63
Xn - Harmful: R43

EC Safety Classification

S2, S36/37, S46

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

profoxydim

French

German

Danish

Italian

Spanish

Greek

Polish

profoksydim

Swedish

Hungarian

Dutch

Record last updated:	12/01/2021
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242