picloram

picloram (Ref: X 159868)
** piclorame ** picloram acid ** Translations

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GENERAL INFORMATION
for picloram

Description: A persistent herbicide for the control of broad-leaved weeds on non-crop and utility areas

Introduction: 1963

EC Regulation 1107/2009 (repealing 91/414): 0 cellpadding= 5 cellspacing= 1 width= 99% > valign= top bgcolor= #E2E2E2 > Status valign= top bgcolor= #E2E2E2 > Approved valign= top bgcolor= #E2E2E2 > Dossier rapporteur/co-rapporteur valign= top bgcolor= #E2E2E2 > UK valign= top bgcolor= #E2E2E2 > Date inclusion expires valign= top bgcolor= #E2E2E2 > 31/12/2018 > Approved for use () or known to be used () in the following European countries: 0 cellpadding= 5 cellspacing= 1 width= 99% > bgcolor= #E2E2E2 >

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> Also registered in: Australia

General status:

Pesticide type Herbicide

Substance group Pyridine compound

Substance origin Synthetic
Mode of action Selective, systemic absorbed by roots and leaves and translocated. Synthetic auxin.

CAS RN 1918-02-1

EC number 217-636-1

CIPAC number 174

US EPA chemical code 005101

Chiral molecule No

Chemical formula C₆H₃Cl₃N₂O₂

SMILES Clc1c(N)c(Cl)c(nc1Cl)C(=O)O

International Chemical Identifier key (InChIKey) NQQVFXUMIDALNH-UHFFFAOYSA-N

International Chemical Identifier (InChI) InChI=1S/C6H3Cl3N2O2/c7-1-3(10)2(8)5(9)11-4(1)6(12)13/h(H2,10,11)(H,12,13)

Structure diagram/image available? Yes

Molecular mass (g mol^-1) 241.46

PIN (Preferred Identification Name) -

IUPAC name 4-amino-3,5,6-trichloropyridine-2-carboxylic acid

CAS name 4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid

Other status information -

Herbicide Resistance Classification (HRAC) O

Herbicide Resistance Classification (WSSA) 4

Insecticide Resistance Classification (IRAC) Not applicable

Fungicide Resistance Classification (FRAC) Not applicable

Physical state Light brown to tan coloured solid

Related substances & organisms
clopyralid

2,4-D

dicamba

fluroxypyr

Formulations:

Property Value
Example manufacturers & suppliers of products using this active
AgriGuard
Dow AgroSciences
Nomix Environ
Pan Agriculture

Example products using this active
Galera
Tordone 22K
Tordone 101

UK LERAP status None

Formulation and application details Often supplied as a soluble concentrate or liquid that is mixed with water and used as a spray.

ENVIRONMENTAL FATE
for picloram

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20^oC (mg l^-1)		560	A5	High
Solubility - In organic solvents at 20^oC (mg l^-1)		10	A5 - n-Heptane	-
		105	A5 - Xylene	-
		23900	A5 - Acetone	-
		19100	A5 - Methanol	-
Melting point (^oC)		174	A5	-
Boiling point (^oC)		Decomposes before boiling	A5	-
Degradation point (^oC)		179	A5	-
Flashpoint (^oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20^oC	P	1.20 X 10^-02	Calculated	-
Octanol-water partition coefficient at pH 7, 20^oC	Log P	-1.92	A5	Low
Bulk density (g ml^-1)/Specific gravity		1.81	Q2	-
Dissociation constant (pKa) at 25^oC		2.3	A5	-
Dissociation constant (pKa) at 25^oC		Note: Strong acid
Vapour pressure at 25^oC (mPa)		8.0 X 10^-05	A5	Non-volatile
Henry's law constant at 25^oC (Pa m³ mol^-1)		3.0 X 10^-07	A5	Non-volatile
Henry's law constant at 20^oC (dimensionless)		1.42 X 10^-11	Calculated	Non-volatile
GUS leaching potential index		6.03	Calculated	High leachability
SCI-GROW groundwater index (μg l^-1) for a 1 kg ha^-1 or 1 l ha^-1 application rate	Value	1.17 X 10⁺⁰¹	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Medium
Maximum UV-vis absorption L mol^-1 cm^-1		Unbuffered pH4.42 solution: 223nm = 28900; [Acidic solution: 223nm = 28700, 293nm = 2100; [Basic solution: 223nm = 30400, 293nm = 2100	A5	-
Surface tension (mN m^-1)		72.0	A5 at 20^oC	-

Degradation:

Property Value Source/Quality Score/Other Information Interpretation

Soil degradation (days) (aerobic) DT50 (typical) 82.8 A5 Moderately persistent

DT50 (lab at 20^oC) 82.8 A5 Moderately persistent

DT50 (field) 36 A4 Moderately persistent

DT90 (lab at 20^oC) 318 A5 -

DT90 (field) 120 A5 -

Note EU dossier Lab studies DT50 range 5.2-292 days, DT90 range 16.7-982.1 days; Field studies DT50 range 20-49 days, DT90 range 67-163 days

Aqueous photolysis DT50 (days) at pH 7 Value 2.0 A5 Moderately fast

Note DT50: 3.5 days sterile water , 2 days natural water both in summer sunlight 40 deg N and pH 5

Aqueous hydrolysis DT50 (days) at 20^oC and pH 7 Value Stable A5 Very persistent

Note Stable pH 5 to pH 9, at 25 degC

Water-sediment DT50 (days) 196.1 A5 Slow

Water phase only DT50 (days) 80.8 A5 Stable

Soil adsorption and mobility:

Property Value Source/Quality Score/Other Information Interpretation

Linear K_d - DW3 Very mobile

K_oc 13

Notes and range -

Freundlich K_f 0.14 A5 Very mobile

K_foc 7.22

¹/_n 0.773

Notes and range EU dossier Kf range 0.04-0.73 mL/g, Kfoc range 0.31-20.3 mL/g, 1/n range 0.44-1.52, Soils=14

pH sensitivity Yes - soils pH >5 show lower adsorption

Other known metabolites:

Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes

4-amino-3,5-dichloro-6-hydroxypicolinic acid 6-OH picloram Plant - -

oxamic acid - Water (Photolysis) - -

3-oxo-beta-alanine - Water (Photolysis) - -

4-amino-2,3,5-trichloropyridine
(Ref: K-041160) PYR Plant - -

aminopyralid
(Ref: XDE 750)
Note: A5 - Water; Sediment - -

ECOTOXICOLOGY
for picloram

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF	74	F4 Whole fish	Low potential
Bio-concentration factor	CT₅₀ (days)	Not available	F4 Whole fish	-
Bioaccumulation potential		-	Calculated	Low
Mammals - Acute oral LD₅₀ (mg kg^-1)		4012	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg^-1)	-	L2 Rat, 2 year	-
Mammals - Short term dietary NOEL	(ppm diet)	20	L2 Rat, 2 year	-
Birds - Acute LD₅₀ (mg kg^-1)		> 1944	A5 Anas platyrhynchos	Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)		> 5620 mg kg feed^-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC₅₀ (mg l^-1)		8.8	A5 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l^-1)		0.55	A5 Oncorhynchus mykiss	-
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l^-1)		44.2	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l^-1)		6.79	A5 Daphnia magna	-
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)		100	A5 Chironomus riparius	Low
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg^-1)		-	-	-
Aquatic plants - Acute 7 day EC₅₀, biomass (mg l^-1)		102	A5 Lemna gibba	Low
Algae - Acute 72 hour EC₅₀, growth (mg l^-1)		60.2	A5 Pseudokirchneriella subcapitata	Low
Algae - Chronic 96 hour NOEC, growth (mg l^-1)		-	-	-
Honeybees	Contact acute 48 hour LD₅₀ (μg bee^-1)	-	-	-
	Oral acute 48 hour LD₅₀ (μg bee^-1)	> 74	A5	Moderate
	Unknown mode acute 48 hour LD₅₀ (μg bee^-1)	-	-	-
Earthworms - Acute 14 day LC₅₀ (mg kg^-1)		> 4475	A5 Eisenia foetida	Low
Earthworms - Chronic 14 day NOEC, reproduction (mg kg^-1)		0.167	A4 Eisenia foetida, 8 week	Moderate
Other soil macro-organisms - e.g. Collembola	LR₅₀ / EC₅₀ / NOEC / % Effect	-	-	-
Other arthropod (1)	LR₅₀ g ha^-1	23.45	A5 Aphidius rhopalosiphi	Harmful at 1 kg ha^-1 Moderately harmful at 0.1 kg ha^-1 Harmless at 0.01 kg ha^-1
Other arthropod (1)	% Effect	-	-	-
Other arthropod (2)	LR₅₀ g ha^-1	23.45	A5 Typhlodromus pyri	Harmful at 1 kg ha^-1 Moderately harmful at 0.1 kg ha^-1 Harmless at 0.01 kg ha^-1
Other arthropod (2)	% Effect	-	-	-
Soil micro-organisms		-	-	-
Mesocosm study data	NOEAEC mg l^-1	-	-	-
Mesocosm study data	NOEAEC mg l^-1	-	-	-

HUMAN HEALTH AND PROTECTION
for picloram

General:

Property Value Source/Quality Score/Other Information Interpretation

Mammals - Acute oral LD₅₀ (mg kg^-1) 4012 A5 Rat Low

Mammals - Dermal LD50 (mg kg^-1 body weight) > 2000 A5 Rat -

Mammals - Inhalation LC50 (mg l^-1) > 0.035 A5 Rat, 4 hr (whole body) -

Other Mammal toxicity endpoints - -

ADI - Acceptable Daily Intake (mg kg^-1bw day^-1) 0.3 A5 Rabbit, SF=100 -

ARfD - Acute Reference Dose (mg kg^-1bw day^-1) 0.3 A5 Rabbit, SF=100 -

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg^-1bw day^-1) 0.3 A5 Rabbit, SF=100 -

Dermal penetration studies (%) 0.1-10.0 A5 concentration dependant -

Dangerous Substances Directive 76/464 - - -

Exposure Limits [LT TWA 8hr: 10 mg/m³], [ST 15 mins: 20 mg/m³] MEL UK HSE -

Exposure Routes Public No unacceptable risks to bystanders identified

Occupational No unacceptable risks to operators or other workers identified

Examples of European MRLs (mg kg^-1) Value Rapeseed: 0.01

Note A5 EU dossier proposals
For the EU pesticides database click here

Drinking Water MAC (μg l^-1) 0.1 EU Dir 89/778/EC limit; Calc MAC=900 �g/l; A5 -

Health issues:

Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant Respiratory tract irritant Skin irritant Eye irritant

-

General human health issues Slightly toxic

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data

Handling issues:

Property Value Source/Quality Score/Other Information Interpretation

General Prevent generation of dust
Not oxidising or explosive
IMDG Transport Code is usually 9

CLP classification 2013 -

EC Risk Classification N - Dangerous for the environment: R51, R53

EC Safety Classification S60, S61

WHO Classification U - Unlikely to present an acute hazard

US EPA Classification (formulation) I - Danger - Highly toxic

UN Number Usually 3082

Waste disposal & packaging Packaging Group III (minor danger)

TRANSLATIONS
for picloram

Language	Name
English	picloram
French	piclorame
German	Picloram
Danish	picloram
Italian	picloram
Spanish	picloram
Greek	-
Slovenian	pikloram
Polish	pikloram
Swedish	-
Hungarian	-
Dutch	-

Record last updated: Wednesday 10 December 2014
Contact: aeru@herts.ac.uk

Pesticide type	Herbicide
Substance group	Pyridine compound
Substance origin	Synthetic
Mode of action	Selective, systemic absorbed by roots and leaves and translocated. Synthetic auxin.
CAS RN	1918-02-1
EC number	217-636-1
CIPAC number	174
US EPA chemical code	005101
Chiral molecule	No
Chemical formula	C₆H₃Cl₃N₂O₂
SMILES	Clc1c(N)c(Cl)c(nc1Cl)C(=O)O
International Chemical Identifier key (InChIKey)	NQQVFXUMIDALNH-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C6H3Cl3N2O2/c7-1-3(10)2(8)5(9)11-4(1)6(12)13/h(H2,10,11)(H,12,13)
Structure diagram/image available?	Yes
Molecular mass (g mol^-1)	241.46
PIN (Preferred Identification Name)	-
IUPAC name	4-amino-3,5,6-trichloropyridine-2-carboxylic acid
CAS name	4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid
Other status information	-
Herbicide Resistance Classification (HRAC)	O
Herbicide Resistance Classification (WSSA)	4
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	Not applicable
Physical state	Light brown to tan coloured solid
Related substances & organisms	clopyralid 2,4-D dicamba fluroxypyr

Property	Value
Example manufacturers & suppliers of products using this active	AgriGuard Dow AgroSciences Nomix Environ Pan Agriculture
Example products using this active	Galera Tordone 22K Tordone 101
UK LERAP status	None
Formulation and application details	Often supplied as a soluble concentrate or liquid that is mixed with water and used as a spray.

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
4-amino-3,5-dichloro-6-hydroxypicolinic acid	6-OH picloram	Plant	-	-
oxamic acid	-	Water (Photolysis)	-	-
3-oxo-beta-alanine	-	Water (Photolysis)	-	-
4-amino-2,3,5-trichloropyridine (Ref: K-041160)	PYR	Plant	-	-
aminopyralid (Ref: XDE 750) Note: A5	-	Water; Sediment	-	-

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant	Respiratory tract irritant	Skin irritant	Eye irritant
					-
General human health issues		Slightly toxic