Fenpyroximate (Ref: NNI 850)

Fenpyroximate (Ref: NNI 850)	Last updated: 20/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A acaricide used to control important phytophagous mites in fruit

Example pests controlled

Tetranychidae, Tarsonemidae, Tenuipalpidae and Eriophyidae

Example applications

Fruit including citrus, apples, pears, peaches, grapes, strawberries, currants; Tree nuts; Ornamentals; Sugarbeet

Efficacy & activity

Demonstrated to offer equivalent or greater benefit than comparable substances via field trials.

Availability status

Current

Introduction & key dates

1990, first reported; 1991, first introduced

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

Not applicable

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Austria/Denmark

Date EC 1107/2009 inclusion expires

30/04/2021

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

Australia

Chemical structure

Isomerism

Isomeric existing in the E- and Z-forms.

Chemical formula

C₂₄H₂₇N₃O₄

Canonical SMILES

CC1=NN(C(=C1C=NOCC2=CC=C(C=C2)C(=O)OC(C)(C)C)OC3=CC=CC=C3)C

Isomeric SMILES

CC1=NN(C(=C1/C=N/OCC2=CC=C(C=C2)C(=O)OC(C)(C)C)OC3=CC=CC=C3)C

International Chemical Identifier key (InChIKey)

YYJNOYZRYGDPNH-MFKUBSTISA-N

International Chemical Identifier (InChI)

InChI=1S/C24H27N3O4/c1-17-21(22(27(5)26-17)30-20-9-7-6-8-10-20)15-25-29-16-18-11-13-19(14-12-18)23(28)31-24(2,3)4/h6-15H,16H2,1-5H3/b25-15+

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
fenpyroximate	-

General status

Pesticide type

Acaricide, Insecticide

Substance group

Pyrazolium

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU 2019 RAR dossier - 1,3-dimethyl-5-phenoxy-4-pyrazolecarbaldehyde oxime (NN-4) < 1 g kg⁻¹; tert-butyl-4-chloromethylbenzoate (NN-9) < 1.4 g kg⁻¹, methanol < 1.0 g.kg

Substance origin

Synthetic

Mode of action

Mitochondrial electron transport inhibitor with contact action

CAS RN

134098-61-6

EC number

603-792-1

CIPAC number

695

US EPA chemical code

129131

PubChem CID

9576412

Molecular mass

421.49

PIN (Preferred Identification Name)

tert-butyl 4-[({[(E)-(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)methylidene]amino}oxy)methyl]benzoate

IUPAC name

tert-butyl (E)-α-(1,3-dimethyl-5-phenoxypyrazol-4-ylmethyleneaminooxy)-p-toluate

CAS name

1,1-dimethylethyl 4-((((E)-((1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)methylene)amino)oxy)methyl)benzoate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Tetranychus kanzawai, Tetranychus urticae

Physical state

White crystalline powder

Formulations

Property

Value

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

Fenpyroximate 5SC
Edonis
Kiron
Sequel
Acaritan

Example products using this active

Certis
Farma-Chem SA
Ypsilon SA

Formulation and application details

Often supplied as a soluble concentrate which is mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.021

Low

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

116000

Acetone

16500

Ethanol

13400

Methanol

193000

Xylene

Melting point (°C)

102.0

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

215

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

5.01 X 10⁰⁵

Calculated

Log P

5.70

High

Bulk density (g ml⁻¹)

1.25

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.00921

Low volatility

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

0.0168

Non-volatile

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

Acidic: 200nm=45400, 235.5nm=22850, 258nm=19260
Neutral; 200nm=47270, 235nm=22510, 258nm=19520
Basic: 218.5nm=21310, 235.5nm=22610, 258nm=19590

Surface tension (mN m⁻¹)

72.2

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

135,.1

Persistent

DT₅₀ (lab at 20 °C)

135.1

Persistent

DT₅₀ (field)

6.8

Non-persistent

DT₉₀ (lab at 20 °C)

358

Persistent

DT₉₀ (field)

31.7

DT₅₀ modelling endpoint

Note

EU 2019 dossier lab studies DT₅₀ (normalised) range 36.1-282 days, DT₉₀ (measured) range 120-790 days,Soils=5, Field studies DT₅₀ (normalised) range 2.8-23.7 days, DT₉₀ (measured) range 9,.32-78.6 days, Soils=4; Other studies: Lab DT₅₀ range 26-50 days (B5)

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

2.6

Note

Published literature RL₅₀ range 1.6-3.2 days, 5 field crops, various matrices, n=7

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.1

Fast

Note

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

Value

9.4

Non-persistent

Note

pH sensitive: DT₅₀ 7.5 days at pH 5, 9.2 days at pH 9

Water-sediment DT₅₀ (days)

33.8

Moderately fast

Water phase only DT₅₀ (days)

2.91

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

629.2

Non-mobile

K_foc

4838

¹/_n

0.95

Notes and range

EU 2019 dossier K_f range 122-2253 mL g⁻¹, K_foc range 11091-72677 mL g⁻¹, ¹/_n range 0.l849-1.03, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.26

Calculated

Low leachability

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

Value

5.73 X 10^-03

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

(E)-4-((1,3-dimethyl-5-phenocypyrazole-4-yl)methyleneaminooxy-methyl)benzoic acid

Soil

0.595

Major fraction, Relevant

1,3-dimethyl-5-phenoxypyrzole-4-carbonitrile

Soil

0.0052

Minor fraction, Relevant

1,3-dimethyl-5-phenoxypyrazole-4-carboxylic acid

Soil

0.0074

Minor fraction, Relevant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

1601

Whole fish

Threshold for concern

CT₅₀ (days)

5.3

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

245

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

1.3

Rat

High

(ppm diet)

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

Rat Reproductive NOAEL

High

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)

3.65

Anas platyrhynchos NOAEDD

High

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.00105

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.00019

Oncorhynchus mykiss

High

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

0.00328

Daphnia magna

High

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

0.00016

Daphnia magna

High

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)

0.01

Chironomus riparius

Moderate

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

0.81

Chironomus riparius

Moderate

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

Non-target plants

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

0.0094

Desmodesmus subspicatus

High

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

0.01

Scenedesmus subspicatus

Moderate

Honeybees (Apis spp.)

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

> 15.8

Apis mellifera

Moderate

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

> 118.5

Apis mellifera

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)

34.7

Eisenia foetida corr

Moderate

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

2.71

Eisenia foetida as EC10 corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

8.6

Folsomia candida corr

Other arthropod (1)

LR₅₀ g ha⁻¹

2.5

>
Typhlodromus pyri

% Effect

100.0

Mortality [Dose: 0.025 kg ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

2.5

>
Aphidius rhopalosiphi

% Effect

Harmful

[Dose: 50 g ha⁻¹]
Phytoseiulus persimillus

Soil micro-organisms

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

Dose: 22.5 kg ha⁻¹ 28days

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)

245

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.33

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

Intravenous LD₅₀ < 0.69 mg kg⁻¹

Rat

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

0.01

Rat SF=100

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

0.01

Dog SF=200

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

0.006

Dog SF=100

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

0.008

Rat SF=100

Dermal penetration studies (%)

2.0-9.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for registered uses

Occupational

Possible risk to operators and other farm workers identified - PPE/PPC advised

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

; ; ; ; EX

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H301, H330, H317
Environment: H400, H410

EC Risk Classification

T+ - Very Toxic: R26
Xn - Harmful: R22, R43
Xi - Irritant: R36

EC Safety Classification

WHO Classification

II (Moderately hazardous)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

fenpyroximate

French

fenpyroximate

German

Fenpyroximat

Danish

fenpyroximat

Italian

fenprioximate

Spanish

fenpiroximato

Greek

Polish

fenpiroksymat

Swedish

fenpyroximat

Hungarian

fenpiroximat

Dutch

Record last updated:	20/01/2021
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