Indaziflam

Indaziflam	Last updated: 04/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

Novel pre-emergence herbicide that controls a broad spectrum of weeds, including species which are difficult to eliminate

Example pests controlled

Annual grasses and broad-leaved weeds including annual bluegrass, goosegrass, ryegrass and goosefoot.

Example applications

Residential; Turf & lawns; Sports fields; Field grown ornamentals; Landscapes; Pome and stone fruit; Citrus; Grapes; Tree nuts; Bananas; Tea; Coffee; Olives

Efficacy & activity

Availability status

Current

Introduction & key dates

2010, first registered USA

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

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Not applicable

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

Japan; Canada; USA; Indonesia; Argentina; Mexico; Philippines; Vietnam

Chemical structure

Isomerism

Indaziflam is a chiral molecule with three asymmetric carbons and two of eight possible isomers (isomer A - IR,2S,1R- and Isomer B - 1R,2S,1S-) are present in the active constituents of indaziflam.

Chemical formula

C₁₆H₂₀FN₅

Canonical SMILES

CC1CC2=C(C1NC3=NC(=NC(=N3)N)C(C)F)C=C(C=C2)C

Isomeric SMILES

C[C@H]1CC2=C([C@@H]1NC3=NC(=NC(=N3)N)C(C)F)C=C(C=C2)C

International Chemical Identifier key (InChIKey)

YFONKFDEZLYQDH-BOURZNODSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H20FN5/c1-8-4-5-11-7-9(2)13(12(11)6-8)19-16-21-14(10(3)17)20-15(18)22-16/h4-6,9-10,13H,7H2,1-3H3,(H3,18,19,20,21,22)/t9-,10?,13+/m0/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Fluoroalkyltriazine

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Inhibits cellulose biosynthesis (CB Inhibitor). Long lasting action and non-selective.

CAS RN

950782-86-2

EC number

CIPAC number

US EPA chemical code

080818

PubChem CID

44146693

Molecular mass

301.36

PIN (Preferred Identification Name)

N2-[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]-6-[(1?)-1-fluoroethyl]-1,3,5-triazine-2,4-diamine

IUPAC name

N-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-[(1RS)-1-fluoroethyl]-1,3,5-triazine-2,4-diamine

CAS name

N-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine

Other status information

Potential groundwater contaminant; Marine pollutant

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

None identified

Physical state

Beige coloured powdery solid

Formulations

Property

Value

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

Alion
Specticle
Becano
Esplanade 200SC

Example products using this active

Bayer CropScience
Bayer Advanced

Formulation and application details

Number of different formulations are emerging world-wide including wettable powders, liquid suspensions, water soluble bags, fertiliser additives, ready-to-use products and granules

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

2.8

at pH 9

Low

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

55000

Acetone

7600

Acetonitrile

13000

Ethanol

Heptane

Melting point (°C)

183

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

6.31 X 10⁰²

Calculated

Log P

2.8

Moderate

Bulk density (g ml⁻¹)

1.23

Dissociation constant pKa) at 25 °C

3.5

Vapour pressure at 20 °C (mPa)

2.5 X 10^-05

Low volatility

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

2.69 X 10^-06

Non-volatile

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

Max @ 213nm, 268nm, 291nm

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

150

Persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

General literature gives DT₅₀ >150 days (aerobic soil), >200 days (anaerobic soils)

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

Moderately fast

Note

Data for clear shallow water

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

Value

Note

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

Slightly mobile

K_oc

1000

Notes and range

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.18

Calculated

Transition state

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

Value

1.06 X 10^-01

Calculated

Note

Potential for particle bound transport index

High

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

fluoroethyldiaminotriazine
Note: Koc <50 mL/g

FDAT

Humans, Soil

triazine-indanone

Environment

indaziflam-carboxylic acid

Environment; Humans

indaziflam-hydroxyethyl

Soil; Water

indaziflam-olefin

Soil; Water

fluoroethyltriazinanedione

Environment

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

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)

> 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)

> 0.42

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.464

Pimephales promelas

Moderate

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

< 9.88

Daphnia magna

Moderate

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

0.34

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)

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

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

0.000019

Lemna gibba NOEC

High

Non-target plants

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

0.75

Pseudokirchneriella subcapitata as formulation

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)

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)

34.0

Eisenia foetida for NOAEC

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

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)

> 2000

Rat

Low

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

2000

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.3

Rat

Other Mammal toxicity endpoints

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

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

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

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

Dermal penetration studies (%)

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

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver and thyroid toxicant
Harmful is swallowed

Handling issues

Property

Value and interpretation

General

IMDG Transport Code is usually 9

CLP classification 2013

EC Risk Classification

Xn - Harmful: R22

EC Safety Classification

WHO Classification

NL (Not listed)

UN Number

3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

indaziflam

French

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	04/01/2021
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