Penoxsulam (Ref: XDE 638)

Penoxsulam (Ref: XDE 638)	Last updated: 12/01/2021
(Also known as: DE 638; DASH-001; DASH-1100)

GENERAL INFORMATION

Description

A new post-emergence herbicide used on rice crops for the control of broad-leaved weeds, aquatic weeds and certain grasses

Example pests controlled

Sedges; Broad-leaved weeds including loosestrife, chickweed and clover; Aquatic weeds including water plaintain and water hyacinth; Certain grasses including barnyardgrass, young watergrass, annual blackgrass and buckwheat

Example applications

Lawns; Rice; Cereals; Orchards; Olives

Efficacy & activity

Availability status

Current

Introduction & key dates

2004, Turkey

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

Italy/Poland

Date EC 1107/2009 inclusion expires

31/07/2023

EU Candidate for substitution (CfS)

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

Chemical formula

C₁₆H₁₄F₅N₅O₅S

Canonical SMILES

COC1=CN=C(N2C1=NC(=N2)NS(=O)(=O)C3=C(C=CC=C3OCC(F)F)C(F)(F)F)OC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

SYJGKVOENHZYMQ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H14F5N5O5S/c1-29-10-6-22-15(30-2)26-13(10)23-14(24-26)25-32(27,28)12-8(16(19,20)21)4-3-5-9(12)31-7-11(17)18/h3-6,11H,7H2,1-2H3,(H,24,25)/f/h25H

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Triazopyrimidine

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - Bis-CHYMP, max content 0.5g kg⁻¹

Substance origin

Synthetic

Mode of action

Broad spectrum, absorbed mainly by leaves and, to lesser extent, roots and translocated, exhibits knockdown and residual control. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS.

CAS RN

219714-96-2

EC number

CIPAC number

758

US EPA chemical code

119031

PubChem CID

11784975

Molecular mass

483.37

PIN (Preferred Identification Name)

IUPAC name

3-(2,2-difluoroethoxy)-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-α,α,α-trifluorotoluene-2-sulfonamide

CAS name

2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy(1,2,4)triazolo(1,5-c)pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide

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

Echinochloa crus-galli

Physical state

Off-white to pale pink solid

Related substances & organisms

propylene glycol

cyhalofop-butyl

Formulations

Property

Value

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

Penoxsulam DE638
Galleon
Granite
Grasp Xtra
Sapphire

Example products using this active

Dow AgroSciences

Formulation and application details

Used as a broadcast spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

408

Moderate

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

20300

Acetone

1480

Methanol

n-Octanol

15300

Acetonitrile

Melting point (°C)

212

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

214

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.50 X 10^-01

Calculated

Log P

-0.602

Low

Bulk density (g ml⁻¹)

1.61

Dissociation constant pKa) at 25 °C

5.1

Weak acid

Vapour pressure at 20 °C (mPa)

2.49 X 10^-11

Low volatility

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

2.94 X 10^-14

Non-volatile

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

Neutral solution: 284nm = 9530
Acidic solution: 251nm = 7450, 284nm = 9520
Basic solution: 228nm = 44300, 284nm = 9380

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

Moderately persistent

DT₅₀ (field)

5.9

Non-persistent

DT₉₀ (lab at 20 °C)

107

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 22-58 days, DT₉₀ range 74-192 day, Field studies DT₅₀ range 5.6-6.1 days; Literature lab values DT₅₀ range 4.8-10.6 days (anaerobic, global), 22-118 days (aerobic global), 6.6 days (anaerobic EU), 22-58 days (aerobic, EU)

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

2.8

Note

Published literature RL₅₀ range 1.1-4.4 days, 2 field crops, various matrices, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Moderately fast

Note

Main degradation route in water

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

Value

Stable

Note

Stable under all normal environmental conditions

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

1.4

Mobile

K_oc

73.2

Notes and range

EU dossier K_d range 0.13-1.44 mL g⁻¹, K_oc range 13-305 mL g⁻¹, Soils=17; Literature K_oc 12-1141 mL g⁻¹ (global), 12-305 mL g⁻¹ (EU)

Freundlich

K_f

1.27

Moderately mobile

K_foc

¹/_n

0.91

Notes and range

EU dossier K_f range 0.16-4.69, K_foc range 10-382 mL g⁻¹, ¹/_n range 0.80-1.09, Soils=12

pH sensitivity

Sorption increases with decreasing pH

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.56

Calculated

Low leachability

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

Value

5.02 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

2-(2,2-difluoroethoxy)-N-(5-hydroxy-8-methoxy(1,2,4)triazolo(1,5-c)pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide

Soil

0.405

Major fraction, Relevant

3-(((2-(2,2-difluoroethoxy)-6-(trifluoromethyl)phenyl)sulfonyl)amino)-1H-1,2,4-triazole-5-carboxylic acid

Soil

0.530

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)sulfamic acid

TPSA

Water (Photolysis)

0.560

5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amine

2-amino-TP

Water (Photolysis)

0.230

3-(2,2-difluoroethoxy)-2-[(5-hydroxy-8-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)sulfamoyl]benzoic acid

PCA-5-OH

Water/sediment

3-({[2-(2,2-difluoroethoxy)-?-hydroxy-6-(trifluoromethyl)phenyl]sulfonyl}amino)-1H-1,2,4-triazole-5-carboxylic acid

OH-BSTCA

Water/sediment

2-hydroxyphenyl-penoxsulam: N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-2-hydroxy-6-(trifluoromethyl)benzenesulfonamide

2-hydroxyphenyl-penoxsulam

Unknown

2-(2,2-difluoroethoxy)-N-(1H-1,2,4-triazol-3-yl)-6-(trifluoromethyl)benzenesulfonamide

BST

Soil; Plants

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

100

Threshold for concern

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2025

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 804 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 100

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

10.2

Pimephales promelas

Low

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

98.3

Daphnia magna

Moderate

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

2.95

Daphnia magna

Moderate

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

114

Americamysis bahia

Low

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

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

61.0

Chironomus riparius

Low

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

810

Chironomus riparius

Low

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

0.003

Lemna gibba

High

Non-target plants

6.2

Sugarbeet
Seedling emergence, EC₅₀, shoot weight
as g ha⁻¹

6.2

Soybean
Vegetative vigour, shoot weight, EC₅₀
as g ha⁻¹

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

0.49

Anabaena flos-aquae

Moderate

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

Honeybees (Apis spp.)

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

> 100

Low

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

> 100

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)

> 1000

Eisenia foetida

Low

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

>, 48 hour
Aphidius rhopalosiphi

% Effect

0 / 26

Mortality / Fecundity [Dose: 40 g ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

7.46

Fecundity
Typhlodromus pyri

% Effect

0 / 8.2

Mortality / Fecundity [Dose: 40 g ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

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)

5000

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

3.5

Rat

Other Mammal toxicity endpoints

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

0.05

Rat SF=100

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

Not allocated

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

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

0.18

Dog SF=100

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Acceptable for proposed uses

Occupational

Acceptable for proposed uses

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

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible blood, liver and kidney toxicant
USEPA - some evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Environment: H400, H410

EC Risk Classification

N - Dangerous for the environment: R50/53

EC Safety Classification

S57

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

penoxsulam

French

penoxsulame

German

Penoxsulam

Danish

penoxsulam

Italian

penoxsulam

Spanish

penoxsulam

Greek

Polish

penoksulam

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