Product Name

  • Name

    Picloram

  • EINECS 217-636-1
  • CAS No. 1918-02-1
  • Article Data16
  • CAS DataBase
  • Density 1.811 g/cm3
  • Solubility 420 mg/L in water
  • Melting Point 215 °C
  • Formula C6H3Cl3N2O2
  • Boiling Point 420.5 °C at 760 mmHg
  • Molecular Weight 241.461
  • Flash Point 208.1 °C
  • Transport Information
  • Appearance fine beige crystals or white powder
  • Safety 26
  • Risk Codes 36
  • Molecular Structure Molecular Structure of 1918-02-1 (Picloram)
  • Hazard Symbols IrritantXi
  • Synonyms Picolinicacid, 4-amino-3,5,6-trichloro- (8CI);3,5,6-Trichloro-4-aminopicolinic acid;4-Amino-3,5,6-trichloro-2-picolinic acid;4-Amino-3,5,6-trichloropicolinicacid;4-Amino-3,5,6-trichloropyridine-2-carboxylic acid;4-Aminotrichloropicolinic acid;ATCP;Grazon PC;NSC 233899;Padron(herbicide);Tordon;
  • PSA 76.21000
  • LogP 2.90340

Synthetic route

4-amino-3,5,6-trichloro-2-trichloromethylpyridine
5005-62-9

4-amino-3,5,6-trichloro-2-trichloromethylpyridine

A

4-amino-2,3,5-trichloropyridine
28443-69-8

4-amino-2,3,5-trichloropyridine

B

picloram
1918-02-1

picloram

Conditions
ConditionsYield
With sulfuric acid; trichloroacetic acid In water at 110℃; for 10h;A n/a
B 88.3%
With sulfuric acid; trichloroacetic acid In water at 110℃; for 10h; Product distribution; var. temperature, reaction time, additives, and purity of the substrate; hydrolysis;A n/a
B 88.3%
ammonium hydroxide
1336-21-6

ammonium hydroxide

3,4,5,6-tetrachloropicolinonitrile
17824-83-8

3,4,5,6-tetrachloropicolinonitrile

picloram
1918-02-1

picloram

Conditions
ConditionsYield
With ammonia
C6H3Cl3N2O2*C40H48N8

C6H3Cl3N2O2*C40H48N8

A

C40H48N8
1156544-32-9

C40H48N8

B

picloram
1918-02-1

picloram

Conditions
ConditionsYield
With potassium chloride In methanol; water at 25.04℃; Equilibrium constant; pH-value; Reagent/catalyst; Solvent;
C6H3Cl3N2O2*C36H42N10

C6H3Cl3N2O2*C36H42N10

A

C36H42N10
1156544-33-0

C36H42N10

B

picloram
1918-02-1

picloram

Conditions
ConditionsYield
With potassium chloride In water at 25.04℃; Equilibrium constant; pH-value; Reagent/catalyst; Solvent;
C6H3Cl3N2O2*C42H54N10

C6H3Cl3N2O2*C42H54N10

A

C42H54N10
1156544-34-1

C42H54N10

B

picloram
1918-02-1

picloram

Conditions
ConditionsYield
With potassium chloride In water at 25.04℃; Equilibrium constant; pH-value; Reagent/catalyst; Solvent;
aminopyralid
150114-71-9

aminopyralid

A

4-amino-3,6-dichloro-5-fluoropyridine-2-carboxylic acid

4-amino-3,6-dichloro-5-fluoropyridine-2-carboxylic acid

B

picloram
1918-02-1

picloram

Conditions
ConditionsYield
With Selectfluor In water at 25 - 65℃;A 40 %Chromat.
B 4.5 %Chromat.
picloram
1918-02-1

picloram

4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid monopotassium salt
2545-60-0

4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid monopotassium salt

Conditions
ConditionsYield
With potassium hydrogencarbonate at 20 - 65℃; under 760.051 Torr; for 1.33333h; Temperature;99.6%
picloram
1918-02-1

picloram

4-amino-3,5,6-trichloropicolinate sodium

4-amino-3,5,6-trichloropicolinate sodium

Conditions
ConditionsYield
With sodium hydrogencarbonate at 20 - 65℃; under 760.051 Torr; for 1.25h; Temperature;99.6%
picloram
1918-02-1

picloram

trimethylamine
75-50-3

trimethylamine

picloram trimethylamine

picloram trimethylamine

Conditions
ConditionsYield
at 20 - 55℃; under 760.051 Torr; for 1.2h; Sealed tube;99.6%
picloram
1918-02-1

picloram

isopropylamine
75-31-0

isopropylamine

picloram isopropylamine

picloram isopropylamine

Conditions
ConditionsYield
at 20 - 50℃; under 760.051 Torr; for 1.23333h; Sealed tube;99.6%
picloram
1918-02-1

picloram

3-amino-2-propanol
78-96-6, 1674-56-2

3-amino-2-propanol

picloram isopropanolamine

picloram isopropanolamine

Conditions
ConditionsYield
at 20 - 60℃; under 760.051 Torr; for 1.25h; Sealed tube;99.6%
picloram
1918-02-1

picloram

picloram amine salt

picloram amine salt

Conditions
ConditionsYield
With ammonium bicarbonate at 20 - 65℃; under 760.051 Torr; for 1.16667h;99.5%
picloram
1918-02-1

picloram

methylamine
74-89-5

methylamine

picloram methylamine

picloram methylamine

Conditions
ConditionsYield
at 20 - 60℃; under 760.051 Torr; for 1.25h; Sealed tube;99.4%
picloram
1918-02-1

picloram

dimethyl amine
124-40-3

dimethyl amine

picloram dimethylamine

picloram dimethylamine

Conditions
ConditionsYield
at 20 - 65℃; under 760.051 Torr; for 1.25h; Sealed tube;99.2%
picloram
1918-02-1

picloram

4-aminopyridine-2-carboxylic acid
100047-36-7

4-aminopyridine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: picloram With hydrogen; lithium hydroxide; palladium 10% on activated carbon In water at 40 - 70℃; under 2327.23 Torr; for 16h;
Stage #2: With hydrogenchloride In water pH=3;		99%
diquat dibromide
85-00-7

diquat dibromide

picloram
1918-02-1

picloram

2C6H2Cl3N2O2(1-)*C12H12N2(2+)

2C6H2Cl3N2O2(1-)*C12H12N2(2+)

Conditions
ConditionsYield
With sodium hydroxide In water96%
picloram
1918-02-1

picloram

isopropyl alcohol
67-63-0

isopropyl alcohol

iso-propyl 4-amino-3,5,6-trichloropicolinate

iso-propyl 4-amino-3,5,6-trichloropicolinate

Conditions
ConditionsYield
With sulfuric acid for 18h; Reagent/catalyst; Reflux;94%
methanol
67-56-1

methanol

picloram
1918-02-1

picloram

methyl 4-amino-3,5,6-trichloropicolinate
14143-55-6

methyl 4-amino-3,5,6-trichloropicolinate

Conditions
ConditionsYield
With thionyl chloride at 0 - 50℃; for 4h;92.6%
With thionyl chloride at 0℃; for 3h; Reflux;91%
With thionyl chloride at 0 - 50℃; for 4h;78%
With thionyl chloride at 75℃; for 18h; Reagent/catalyst;
picloram
1918-02-1

picloram

aminopyralid
150114-71-9

aminopyralid

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen; sodium hydroxide In water at 50℃; under 1500.15 - 2250.23 Torr; for 20h; Reagent/catalyst; Pressure; Temperature;91.4%
With sodium hydroxide In water at 35 - 38℃; for 36h; Product distribution / selectivity; Electrochemical reaction;
With sodium hydroxide; sodium chloride In water at 35 - 38℃; for 24 - 46h; Product distribution / selectivity; Electrochemical reaction;
picloram
1918-02-1

picloram

sodium 4-amino-3,6-dichloropicolinate

sodium 4-amino-3,6-dichloropicolinate

Conditions
ConditionsYield
With sodium sulfite at 80℃; under 675.068 Torr; pH=7 - 8; Reagent/catalyst; Temperature; pH-value;87.1%
picloram
1918-02-1

picloram

3,4,5,6-tetrachloropyridinecarboxylic acid
10469-09-7

3,4,5,6-tetrachloropyridinecarboxylic acid

Conditions
ConditionsYield
Stage #1: picloram With hydrogenchloride; sodium nitrite In toluene at 0 - 5℃; for 0.5h;
Stage #2: With copper(l) chloride In toluene at 5 - 55℃;		86.9%
tetramethyl ammoniumhydroxide
75-59-2

tetramethyl ammoniumhydroxide

picloram
1918-02-1

picloram

Tetramethylammonium 4-amino-3,5,6-trichloropicolinate
80586-66-9

Tetramethylammonium 4-amino-3,5,6-trichloropicolinate

Conditions
ConditionsYield
In water80%
tetra(n-butyl)ammonium hydroxide
2052-49-5

tetra(n-butyl)ammonium hydroxide

picloram
1918-02-1

picloram

Tetrabutylammonium 4-amino-3,5,6-trichloropicolinate

Tetrabutylammonium 4-amino-3,5,6-trichloropicolinate

Conditions
ConditionsYield
In water
picloram
1918-02-1

picloram

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

1-O-(4-Amino-3,5,6-trichloropicolinyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose
80586-64-7

1-O-(4-Amino-3,5,6-trichloropicolinyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Conditions
ConditionsYield
With silver(l) oxide In 1,4-dioxane at 20℃; for 24h;
picloram
1918-02-1

picloram

A

2-(hydroxymethyl)-4-aminopyridine
100114-58-7

2-(hydroxymethyl)-4-aminopyridine

B

4-aminopyridine-2-carboxylic acid
100047-36-7

4-aminopyridine-2-carboxylic acid

C

4-amino-3-chloro-pyridine-2-carboxylic acid

4-amino-3-chloro-pyridine-2-carboxylic acid

D

4-amino-6-chloropyridine-2-carboxylic acid

4-amino-6-chloropyridine-2-carboxylic acid

Conditions
ConditionsYield
iron In phosphate buffer at 22℃; for 0.333333h; pH=6.6; Kinetics; Product distribution;
...Expand
picloram
1918-02-1

picloram

methyl iodide
74-88-4

methyl iodide

methyl 4-amino-3,5,6-trichloropicolinate
14143-55-6

methyl 4-amino-3,5,6-trichloropicolinate

Conditions
ConditionsYield
With lithium carbonate In N,N-dimethyl-formamide at 60℃;
picloram
1918-02-1

picloram

phenol
108-95-2

phenol

methyl 4-amino-3,5-dichloro-6-phenoxypyridine-2-carboxylate

methyl 4-amino-3,5-dichloro-6-phenoxypyridine-2-carboxylate

Conditions
ConditionsYield
With sodium hydroxide In methanol; hexane; water; dimethyl sulfoxide; ethyl acetate
2,4-diamino-3,5,6-trichloropyridine dihydrobromide

2,4-diamino-3,5,6-trichloropyridine dihydrobromide

diphenylphosphoranyl azide
4129-17-3

diphenylphosphoranyl azide

picloram
1918-02-1

picloram

4-amino-2-iminopiperidine dihydrobromide

4-amino-2-iminopiperidine dihydrobromide

Conditions
ConditionsYield
With aqueous HBr; hydrogen; triethylamine In ethanol; tert-butyl alcohol
...Expand
manganese(II) acetate
638-38-0, 993-02-2, 2180-18-9, 15411-95-7, 22981-23-3, 27004-39-3

manganese(II) acetate

picloram
1918-02-1

picloram

bis(4-amino-3,5,6-trichloropicolinato)manganese(II) dihydrate

bis(4-amino-3,5,6-trichloropicolinato)manganese(II) dihydrate

Conditions
ConditionsYield
In water stoich. amount of a hot aq. soln. of Mn(ac)2 and a neutral soln. of theorg. compd. reacted; left to stand for several weeks, elem. anal.;
picloram
1918-02-1

picloram

silver nitrate

silver nitrate

bis{aquabis(4-amino-3,5,6-trichloropyridine-2-carboxylato)silver(I)} dihydrate

bis{aquabis(4-amino-3,5,6-trichloropyridine-2-carboxylato)silver(I)} dihydrate

Conditions
ConditionsYield
In ammonia aq. ammonia=NH3; mixing of equimol. amts. of AgNO3 and Picloram in aq. NH3, loss of NH3 from the soln. (over a period of a few d in the dark), crystn.; elem. anal.;
C40H48N8
1156544-32-9

C40H48N8

picloram
1918-02-1

picloram

C6H3Cl3N2O2*C40H48N8

C6H3Cl3N2O2*C40H48N8

Conditions
ConditionsYield
With potassium chloride In methanol; water at 25.04℃; Equilibrium constant; pH-value; Reagent/catalyst; Solvent;
C36H42N10
1156544-33-0

C36H42N10

picloram
1918-02-1

picloram

C6H3Cl3N2O2*C36H42N10

C6H3Cl3N2O2*C36H42N10

Conditions
ConditionsYield
With potassium chloride In water at 25.04℃; Equilibrium constant; pH-value; Reagent/catalyst; Solvent;

Picloram Consensus Reports

NCI Carcinogenesis Bioassay (feed); No Evidence: mouse NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-23 ,1978. ; Clear Evidence: rat NCITR*    National Cancer Instit   ute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-23 ,1978. .

Picloram Standards and Recommendations

OSHA PEL: TWA Total Dust: 10 mg/m3; Respirable Fraction: 5 mg/m3
ACGIH TLV: TWA 10 mg/m3; Not Classifiable as a Human Carcinogen

Picloram Specification

The Picloram, with the CAS registry number 1918-02-1, is also known as 4-Amino-3,5,6-trichloropicolinic acid. It belongs to the product category of Insect Hormone. Its EINECS registry number is 217-636-1. Its IUPAC name is called 4-amino-3,5,6-trichloropyridine-2-carboxylic acid. This chemical's classification codes are Agricultural Chemical; Herbicide; Herbicides; Mutation data; Pesticides; Reproductive Effect; Tumor data. You should keep the bottle tightly closed (0-6°C)

Physical properties of Picloram: (1)ACD/LogP: 2.94; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.07; (4)ACD/LogD (pH 7.4): -0.21; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.676; (13)Molar Refractivity: 50.19 cm3; (14)Molar Volume: 133.3 cm3; (15)Surface Tension: 78.6 dyne/cm; (16)Density: 1.811 g/cm3; (17)Melting Point: 200 °C (dec.)(lit.); (18)Flash Point: 208.1 °C; (19)Enthalpy of Vaporization: 71.1 kJ/mol; (20)Boiling Point: 420.5 °C at 760 mmHg; (21)Vapour Pressure: 8E-08 mmHg at 25°C.

Preparation: this chemical can be prepared by 2,3,5-trichloro-6-trichloromethyl-pyridin-4-ylamine. This reaction will need reagent trichloroacetic acid, sulfuric acid and solvent H2O. The reaction time is 10 hours with reaction temperature of 110 ℃. The yield is about 88.3%.

Uses of Picloram: Picloram is a systemic herbicide used for general woody plant control, sold under the trade names Tordon and Grazon. It also controls a wide range of broad-leaved weeds, but most grasses are resistant.Picloram can be sprayed on foliage, injected into plants, applied to cut surfaces, or placed at the base of the plant where it will leach to the roots.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1(=C(C(=NC(=C1Cl)Cl)C(=O)O)Cl)N
(2)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)
(3)InChIKey: NQQVFXUMIDALNH-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
duck LD50 oral > 2gm/kg (2000mg/kg)   Down to Earth. Vol. 35, Pg. 25, 1979.
rabbit LD50 oral 2gm/kg (2000mg/kg)   Guide to the Chemicals Used in Crop Protection. Vol. 6, Pg. 414, 1973.
rabbit LD50 skin > 4gm/kg (4000mg/kg)   World Review of Pest Control. Vol. 9, Pg. 119, 1970.
rat LD50 oral 8200mg/kg (8200mg/kg)   Down to Earth. Vol. 35, Pg. 25, 1979.

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