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oryzalin (Ref: EL 119)
** dinitrodipropylsulfanilamide ** dirimal ** surflan ** Translations

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

SUMMARY

Oryzalin is a pre-emergence surface-applied herbicide that is not approved for use in the EU. It has a low aqueous solubility, is not volatile and, based on its chemical properties, is not expected to leach to groundwater. However, groundwater monitoring programmes have ientified it as a pollutant. It generally tends not to be persistent in soil or water systems. It has a low mammalian toxicity and is a potential carcinogen. It is moderately toxic to birds, most aquatic organisms, honeybees and earthworms.

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

Description: A pre-emergence surface-applied herbicide used for control of annual grasses and broad-leaved weeds in fruit trees and around ornamentals

Example pests controlled: Annual grass weeds including Barnyardgrass; Pigeon grass; Crabgrass; Guinea grass; Broad-leaved weeds including Deadnettle, Fathen; Pigweeds; Nightshade

Example applications: Fruit including citrus, stone fruit, apples, pears and berries; Nuts; Vines; Christmas trees; Ornamental trees; Nursery stock

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1973

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Netherlands/France
Date inclusion expires 31/05/2021
EU Candidate for substitution (CfS) No
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

Also used in: Australia, USA

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism -
Chemical formula C12H18N4O6S
Canonical SMILES CCCN(CCC)C1=C(C=C(C=C1[N+](=O)[O-])S(=O)(=O)N)[N+](=O)[O-]
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) UNAHYJYOSSSJHH-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C12H18N4O6S/c1-3-5-14(6-4-2)12-10(15(17)18)7-9(23(13,21)22)8-11(12)16(19)20/h7-8H,3-6H2,1-2H3,(H2,13,21,22)
Structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Herbicide
Substance group Dinitroaniline
Minimum active substance purity 960 g/kg
Known relevant impurities EU dossier - N-nitrosodipropylamine 0.1 mg/kg; toluene 4g/kg
Substance origin Synthetic
Mode of action Selective affecting physiological growth process. Microtubule assembly inhibition.
CAS RN 19044-88-3
EC number 242-777-0
CIPAC number 537
US EPA chemical code 104201
PubChem CID 29393
Molecular mass (g mol-1) 346.4
PIN (Preferred Identification Name) -
IUPAC name 3,5-dinitro-N4,N4-dipropylsulfanilamide
CAS name 4-(dipropylamino)-3,5-dinitrobenzenesulfonamide
Other status information Potential groundwater contaminant
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) K1
Herbicide Resistance Classification (WSSA) 3
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance -
Physical state Orange crystalline powder
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
  • Dow AgroSciences
  • Elanco
Example products using this active
  • Surflan
  • Dirimal
  • Ryzelan
UK LERAP status No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details Usually supplied as an aqueous suspension or wettable powder.


ENVIRONMENTAL FATE

for oryzalin

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) 1.13 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 250000 A5 - Acetone -
91900 A5 - Methanol -
0.709 A5 - n-Heptane -
1570 A5 - Xylene -
Melting point (oC) 139.7 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 213 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 5.37 X 1003 Calculated -
Log P 3.73 G4 High
Bulk density (g ml-1)/Specific gravity 1.2 L3 -
Dissociation constant (pKa) at 25oC 9.4 A5 -
Note: Very weak acid
Vapour pressure at 20oC (mPa) 1.1 X 10-07 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 3.37 X 10-08 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 2.22 Calculated Transition state
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 1.10 X 10-01 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 Medium
Maximum UV-vis absorption L mol-1 cm-1 Neutral solution: 208nm = 17200, 282nm = 97600, 380nm = 2690; [Acidic solution: 206nm = 17500, 282nm = 380nm = 2740; [Basic solution: 218nm = 14600, 273nm = 10100, 393nm = 2020 A5 -
Surface tension (mN m-1) 63.5 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) 44.8 A5 Moderately persistent
DT50 (lab at 20oC) 88 A5 Moderately persistent
DT50 (field) 98.2 A5 Moderately persistent
DT90 (lab at 20oC) 559 A5 -
DT90 (field) 184.9 A5 -
DT50 modelling endpoint - - -
Note EU dossier lab studies DT50 range 32-456 days, DT90 range 100-1553 days, field studies DT50 range 10.9-113.2 days, DT90 range 66-376 days ; Other sources: DT50 20 days (DW4)
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 0.08 A5 Fast
Note DT50 1.4 hours sterile water, 1.6 hours river water
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable pH 3 to pH 9 at 25 degC
Water-sediment DT50 (days) 32.7 A5 Moderately fast
Water phase only DT50 (days) 5.9 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 13.0 A5 Slightly mobile
Koc 949
Notes and range EU dossier Kd range 5.23-25.21 mL/g, Koc range 441-1596 mL/g, Soils=12
Freundlich Kf 4.93 A5 Slightly mobile
Kfoc 724
1/n 0.943
Notes and range EU dossier Kf range 4.83-5.04, Kfoc range 439-1008, 1/n = 0.926-0.943
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
4-hydroxy-3,5-dinitro-benzenesulfonamide Soil   0.047   Minor fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
7-amino-2-ethyl-1-propyl-1H-benzimidazole-5-sulfonamide OR-14 Soil (Anaerobic) Soil=0.13 -
2-ethyl-7-nitro-1-propyl-5-sulfonylamino-benzimidazole-3-oxide OR-13 Water (Photolysis); Groundwater - -
3,4-diamino-5-nitrobenzensulfonamide OR-6 Water (Photolysis) - -
2-ethyl-7-nitro-1hydroxy-benzimidazole-5-sulfonamide OR-15-OH Water (Photolysis); Groundwater - -
2-ethyl-7-nitro-1H-benzimidazole-5-sulfonamide OR-15 Water (Photolysis) - -
7-amino-2-ethyl-1H-benzimidazole-5-sulfonamide OR-16 Soil Soil=0.053 -
N-nitroso-N-propylpropan-1-amine - - - -


ECOTOXICOLOGY

for oryzalin

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) 66.1 A5 Whole fish Low potential
CT50 (days) 0.6 -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) - L2 Rat, 2 year -
(ppm diet) > 300 -
Birds - Acute LD50 (mg kg-1) 427 A3 Anas platyrhynchos Moderate
Birds - Short term dietary (LC50/LD50) > 1351 mg kg bw-1 day-1 A5 Anas platyrhynchos -
Fish - Acute 96 hour LC50 (mg l-1) 2.86 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.46 A5 Oncorhynchus mykiss Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 1.02 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.36 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) 0.0154 A5 Lemna gibba Moderate
Non-target plants 26.0 A5 Ryegrass
Seedling emergence, ER50
as g/ha
-
53.9 A5 Lettuce
Seedling emergence, ER50
as g/ha
-
Algae - Acute 72 hour EC50, growth (mg l-1) 18.1 A5 Anabaena flos-aquae Low
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) 40.8 A5 Moderate
Oral acute 48 hour LD50 (μg bee-1) 32 A5 Moderate
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 500 A5 Eisenia foetida, corr Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 34.3 A5 Eisenia foetida Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect 2.66 A5 Folsomia candida, 4 Week NOEC mg kg-1 -
Other arthropod (1) LR50 g ha-1 3852 >
A4 Aphidius rhopalosiphi
-
% Effect - - -
Other arthropod (2) LR50 g ha-1 3852 >
A4 Typhlodromus pyri
-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 25.6 mg kg-1 soil, 28 days
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for oryzalin

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 High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rabbit -
Mammals - Inhalation LC50 (mg l-1) > 4.79 A5 Rat, 4 hr (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.005 A5 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) None allocated 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 (%) 2.5-2.8 A5 concentration dependent -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public Very small risk of exposure of bystanders via drift
Occupational No unacceptable risks to operators or other workers identified
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) 0.1 EU Dir 89/778/EC limit; A5 Calc MAC=50 μg l-1 -

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

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

General human health issues Bioaccumulates
Potential liver, kidney & spleen toxicant
USEPA - probable human carcinogen

: 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 oxidising
Classified as explosive category E
CLP classification 2013 -
EC Risk Classification Click here to view information omn the EU risk phrases Carcinogen category 3: R40
Xn - Harmful: R43
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases -
WHO Classification U - Unlikely to present an acute hazard
US EPA Classification (formulation) III - Caution - Slightly toxic
UN Number Usually 3077
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for oryzalin

Language Name
English oryzalin
French oryzalin
German Oryzalin
Danish oryzalin
Italian oryzalin
Spanish orizalina
Greek -
Slovenian orizalin
Polish oryzalina
Swedish -
Hungarian -
Dutch -

Record last updated: Thursday 23 August 2018
Contact: aeru@herts.ac.uk