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isopyrazam (Ref: SYN 520453)
** A15149W ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for isopyrazam

Description: A novel persisent and broad spectrum fungicide for the cereals and some other crops

Example pests controlled: Septoria tritici, Rusts, Black sigatoka (banana leaf spot disease); Scab; Powder mildews; Alternaria

Example applications: Cereals including winter & spring barley, wheat; Bananas; vegetables, Ornamentals; Various speciality crops

Efficacy & activity: Barley/Rhynchosporium=Moderate; Barley/Mildew=Low; Barley/Rust=Moderate; Barley/Net blotch=Moderate; Barley/Ramularia=Moderate

Availability status: Current

Introduction & key dates: 2008

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur UK
Date inclusion expires 31/03/2023
EU Candidate for substitution (CfS) Yes - two 'Persistent-Bioaccumulative-Toxic' criteria
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism A chiral molecule. The technical material is an isomeric mixture of the syn-isomer (approx. 70-100%) and the anti-isomer (approx. 0-30%)
Chemical formula C20H23F2N3O
Canonical SMILES CC(C)C1C2CCC1C3=C2C=CC=C3NC(=O)C4=CN(N=C4C(F)F)C
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) XTDZGXBTXBEZDN-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C20H23F2N3O/c1-10(2)16-12-7-8-13(16)17-11(12)5-4-6-15(17)23-20(26)14-9-25(3)24-18(14)19(21)22/h4-6,9-10,12-13,16,19H,7-8H2,1-3H3,(H,23,26)/f/h23H
2D structure diagram/image available? Yes

Click to access the Cambridge Crystallographic Data Centre (CCDC) website
Cambridge Crystallographic Data Centre diagrams:
Common Name Relationship Link
Isopyrazam Unstated isomer Click here for the CCDC structure diagram

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Fungicide
Substance group Pyrazole
Minimum active substance purity >920 g/kg
Known relevant impurities EU dossier: none declared
Substance origin Synthetic
Mode of action Protectant, foliar absorption, translocates, inhibits respiration and spore germination and so germ tude elongation - a succinate dehydrogenase inhibitor
CAS RN 881685-58-1
EC number -
CIPAC number -
US EPA chemical code 129222
PubChem CID 25271089
Molecular mass (g mol-1) 359.4
PIN (Preferred Identification Name) mixture of 2 syn-isomers rac-3-(difluoromethyl)-1-methyl-N-[(1R,4S,9R)-9-(propan-2-yl)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-1H-pyrazole-4-carboxamide and 2 anti-isomers rac-3-(difluoromethyl)-1-methyl-N-[(1R,4S,9S)-9-(propan-2-yl)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-1H-pyrazole-4-carboxamide
IUPAC name mixture of 2 isomers 3-(difluoromethyl)-1-methyl-N-[(1RS,4SR,9RS)-1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl]pyrazole-4-carboxamide and 2 aisomers 3-(difluoromethyl)-1-methyl-N-[(1RS,4SR,9SR)-1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl]pyrazole-4-carboxamide
CAS name 3-(difluoromethyl)-1-methyl-N-[1,2,3,4-tetrahydro-9-(1-methylethyl)-1,4-methanonaphthalen-5-yl]-1H-pyrazole-4-carboxamide
Other status information Marine pollutant; PAN listed Highly Hazardous Chemical
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) 7
Examples of recorded resistance None identified
Physical state Off-white coloured solid
Related substances & organisms

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • Syngenta Crop Protection
Example products using this active
  • Bontima
  • Seguris Flexi
  • Zulu
  • Reflect 125 EC
UK LERAP status Buffer probably required in UK - see product label
Formulation and application details Usually supplied as an emulsifiable concentrate and used as a foliar spray.


ENVIRONMENTAL FATE

for isopyrazam

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 0.55 A4 Low
Solubility - In organic solvents at 20oC (mg l-1) 314000 A5 - Acetone -
303111 A5 - Dichloromethane -
1170 A5 - Hexane -
77100 A5 - Toluene -
Melting point (oC) 137 A4 -
Boiling point (oC) 267 A4 -
Degradation point (oC) 261 A4 -
Flashpoint (oC) - - -
Octanol-water partition coefficient at pH 7, 20oC P 1.78 X 1004 Calculated -
Log P 4.25 A4 High
Bulk density (g ml-1)/Specific gravity - - -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 1.3 X 10-04 A4 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 1.14 X 10-04 A4 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 1.47 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 4.01 X 10-02 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated High
Maximum UV-vis absorption L mol-1 cm-1 225nm = 169771 isomer mean; [295nm = 6712.3 isomer mean A5 -
Surface tension (mN m-1) 63.1 A5 -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 244 A5 Persistent
DT50 (lab at 20oC) 244 A5 Persistent
DT50 (field) 72 A5 Moderately persistent
DT90 (lab at 20oC) 811 A5 -
DT90 (field) 543 A5 -
DT50 modelling endpoint - - -
Note EU dossier DT50 Lab studies range 29.8-976 days, DT90 range 132-1000 days; Field studies DT50 range 9.11-173 days, DT90 range 63.5-2089 days
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 54.3 A5 Stable
Note Natural light, 30-50 DegN, 12hr day length
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable at all environmentally pH's
Water-sediment DT50 (days) 628 A5 Stable
Water phase only DT50 (days) 2.3 A5 Moderately fast

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf 30.3 A5 Slightly mobile
Kfoc 2416
1/n 0.942
Notes and range EU dossier Kf range 11.56-51.83 mL/g, Kfoc range 1732-2491 mL/g, 1/n range 0.92-0.97, Soils=6
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
3-(difluoromethyl)-1-methyl-N-((1R,4S,9R)-1,2,3,4,-tetrahydro-9-(2-hydroxypropan-2-yl)-1,4-methanonaphthalen-5-yl)pyrazsaole-4-carboxamide (Ref: CSCD459488) This metabolite may cause environmental pollution, click here for further information Soil   0.236   Major fraction, Relevant
3-(difluoromethyl)-1H-pyrazole-4-carboxylic acid (Ref: CSCD465008) This metabolite may cause environmental pollution, click here for further information Soil   0.115   Major fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid CSAA798670 Soil 0.054 -
dihydroxy isopyrazam CDCD656800 Hens; Animal (Milk, Tissue) - -
3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide CSCC210616 Soil 0.080 -


ECOTOXICOLOGY

for isopyrazam

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) - - -
CT50 (days) - -
Mammals - Acute oral LD50 (mg kg-1) 2000 A5 Rat Moderate
Mammals - Short term dietary NOEL (mg kg-1) - - -
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2000 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) 5620 mg kg-1 Feed A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) 0.0258 A5 Cyprinus carpio High
Fish - Chronic 21 day NOEC (mg l-1) 0.00287 A5 Pimephales promelas, 28day High
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.044 A5 Daphnia magna High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.013 A5 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) 1.0 A5 Chironomus riparius Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) - - -
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) > 0.5 A5 Lemna gibba Moderate
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 2.2 A5 Pseudokirchneriella 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) > 200 A5 Low
Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) > 192.3 A5 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 A5 Eisenia foetida, corr Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 60 A5 Eisenia foetida, 56 days Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 174.75 A5 Typhlodromus pyri -
% Effect - - -
Other arthropod (2) LR50 g ha-1 41.2 A5 Aphidius rhopalosiphi -
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 1.67 mg kg-1 soil, 28 days
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for isopyrazam

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class - - -
Mammals - Acute oral LD50 (mg kg-1) 2000 A5 Rat Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) > 5000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 5.28 A5 Rat, 4 hr -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.03 A5 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.2 A5 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.05 A5 -
Dermal penetration studies (%) 1.0 A5 -
Dangerous Substances Directive 76/464 - - -
Exposure Routes Public -
Occupational -
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Genotoxic Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

A3; B3; C3; D0; E3

-

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

General human health issues Possible liver toxicant
USEPA - probable human carcinogen
Key: Genotoxicity
A: Chromosome aberration (EFSA database)
B: DNA damage/repair (EFSA database)
C: Gene mutation (EFSA database)
D: Genome mutation (EFSA database)
E: Unspecified genotoxicity type (miscellaneous data source)
0: No data
1: Positive
2: Mixed/ambiguous results
3: Negative
Key: Other
: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
IMDG Transport Code 9
CLP classification 2013 Health: H317, H361
Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases Xn - Harmful: R22, R43
N - Dangerous for the environment: R50/53
EC Safety Classification Click here to view information omn the EU safety phrases S36/37, S60
WHO Classification NL - Not listed
UN Number 3082
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for isopyrazam

Language Name
English isopyrazam
French isopyrazam
German Isopyrazam
Danish -
Italian -
Spanish -
Greek -
Slovenian -
Polish -
Swedish -
Hungarian -
Dutch -

Record last updated: Tuesday 25 June 2019
Contact: aeru@herts.ac.uk