Cyazofamid (Ref: IKF 916)

Cyazofamid (Ref: IKF 916)	Last updated: 12/01/2021
(Not known by any other names)

SUMMARY

Cyazofamid is a foliar fungicide approved for use in the EU. It has a low aqueous solubility, is unlikely to leach to groundwater and is volatile. It is not persistent in soils or aquatic systems. Whilst it has a low mammalian toxicity there is some concern regarding its potential for bioaccumulation. It is a skin and eye irritant. It is moderately toxic to birds, most aquatic organisms, honeybees and earthworms.

GENERAL INFORMATION

Description

A protectant foliar applied fungicide used mainly for controlling Oomycete and Plasmodiophora diseases

Example pests controlled

Late blight; Downy mildew

Example applications

Potatoes; Tomatoes; Turf; Ornamentals; Curcubit vegetables

Efficacy & activity

Availability status

Current

Introduction & key dates

2001, UK, Japan and Korea

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/07/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

France/Latvia

Date EC 1107/2009 inclusion expires

31/07/2021

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

USA

Chemical structure

Isomerism

Chemical formula

C₁₃H₁₃ClN₄O₂S

Canonical SMILES

CC1=CC=C(C=C1)C2=C(N=C(N2S(=O)(=O)N(C)C)C#N)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

YXKMMRDKEKCERS-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C13H13ClN4O2S/c1-9-4-6-10(7-5-9)12-13(14)16-11(8-15)18(12)21(19,20)17(2)3/h4-7H,1-3H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
cyazofamid	-

General status

Pesticide type

Fungicide

Substance group

Cyanoimidazole

Minimum active substance purity

935 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Foliar and soil preventative action with some residual activity. Respiration inhibitor, inhibition of complex III.

CAS RN

120116-88-3

EC number

CIPAC number

653

US EPA chemical code

085651

PubChem CID

9862076

Molecular mass

324.78

PIN (Preferred Identification Name)

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

IUPAC name

4-chloro-2-cyano-N,N-dimethyl-5-p-tolylimidazole-1-sulfonamide

CAS name

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

Physical state

White powder

Formulations

Property

Value

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

Ranman
Docious
Mildicut

Example products using this active

Belchim
ISK Biosciences

Formulation and application details

Usually supplied as a suspension concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.107

Low

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

41900

Acetone

5300

Toluene

Hexane

250

Octanol

Melting point (°C)

152.7

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.58 X 10⁰³

Calculated

Log P

3.2

High

Bulk density (g ml⁻¹)

1.45

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.0133

Low volatility

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

4.03 X 10^-02

Non-volatile

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

279nm = 13400, 191nm = 5.100, no absorption above 330nm

Surface tension (mN m⁻¹)

72.5

at 20 °C 95.5% sat soln

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)

4.5

Non-persistent

DT₉₀ (lab at 20 °C)

24.5

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 5.9-15.1 days, DT₉₀ range 16.8-37.0 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

13.2

Note

Published literature RL₅₀ range 11.0-15.3 days, 2 field crops, various matrices, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.1

Fast

Note

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

Value

Non-persistent

Note

pH sensitive: DT₅₀ 27.2 days at pH 5 and 20 °C, 25 days at pH 9 and 20 °C

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

6.2

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

23.0

Slightly mobile

K_foc

1338

¹/_n

0.96

Notes and range

EU dossier K_f range 4.1-65.1, K_foc range 736-2172 mL g⁻¹, ¹/_n range 0.83-1.07, Soils=4

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.57

Calculated

Low leachability

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

Value

2.96 X 10^-03

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

4-chloro-5-p-tolylimidazole-2-carbonitrile

Soil

0.313

Major fraction, Not relevant

4-chloro-5-p-tolylimidazole-2-carboxamide

Soil

0.137

Major fraction, Not relevant

4-chloro-5-p-tolylimidazole-2-carboxylic acid

Soil

0.213

Major fraction, Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

5-hydroxy-5-p-tolyl-2,4-imidazolidinedion

HTID

Water (Photolysis)

0.185

p-toluamide

Water (Photolysis)

0.121

6-(4-chloro-2-cyanoimidazol-5-yl)-N,N-dimethyl-m-toluenesulfonamide

CCTS

Water (Photolysis)

0.379

4-(4-chloro-2-cyanoimidazol-5-yl)benzoic acid

CCBA

Animal (Urinary)

4-chloro-5-[â-(methylsulfonyl)-p-tolyl]imidazole-2-carbonitrile

CH3SO2-CCIM

Animal (Urinary)

4-chloro-5-[â-(methylsulfinyl)-p-tolyl]imidazole-2-carbonitrile

CH3SO-CCIM

Animal (Urinary)

dimethylsulfamic acid
Note: Oral LD50(rat)=2948mg/kg

DMSA

2-cyano-N,N-dimethyl-5-p-tolylimidazole-4-sulfonamide

CDTS

5-chloro-1-â-D-glucopyranosyl-4-p-tolylimidazole-2-carbonitrile

5-CGTC

4-chloro-5-(4-hydroxymethylphenyl)imidazole-2-carbonitrile

CHCN

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

286

Threshold for concern

CT₅₀ (days)

0.7

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

29.5

Rat

High

(ppm diet)

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

> 936

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 ppm

Colinus virginianus

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

150.7

Coturnix japonica NOAEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.56

Salmonidae

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.13

Oncorhynchus mykiss

Moderate

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

0.19

Daphnia magna

Moderate

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

0.11

Daphnia magna

Moderate

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)

0.1

Chironomus riparius

Moderate

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

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

0.033

Unknown species

Moderate

Non-target plants

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

0.025

Raphidocelis subcapitata

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

Apis mellifera

Low

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

> 151.7

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)

> 500

Eisenia foetida corr

Moderate

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

2.0

Eisenia foetida 56 days corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

37.4

Folsomia candida

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

2.5 / -0.7

Mortality / Parasitism [Dose: 0.21 kg ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

2.5 / 10

Mortality / Reproduction [Dose: 0.21 kg ha⁻¹]
Typhlodromus pyri protonymph

Soil micro-organisms

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

Dose: 1.07 mg kg⁻¹ soil 28 days

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)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.5

Rat 4 hr (whole body)

Other Mammal toxicity endpoints

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

0.17

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

None 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)

0.3

Rat 90 day SF=100

Dermal penetration studies (%)

100

Dangerous Substances Directive 76/464

Exposure Routes

Public

Minimal risk of dietary exposure
Slight risk to bystanders from spray drift
Source: US EPA

Occupational

Low risk

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

Possible kidney & liver toxicant

Handling issues

Property

Value and interpretation

General

Not oxidising or explosive

CLP classification 2013

Environment: H400, H410

EC Risk Classification

N - Dangerous for the environment: R50/53

EC Safety Classification

S60, S61

WHO Classification

NL (Not listed)

UN Number

Usually 1294

Waste disposal & packaging

Packaging Group II (medium danger)

TRANSLATIONS

Language

Name

English

cyazofamid

French

cyazofamid

German

Cyazofamid

Danish

cyazofamid

Italian

cyazofamid

Spanish

ciazofamida

Greek

Polish

cyazofamid

Swedish

cyazofamid

Hungarian

Dutch

cyazofamid

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