123312-89-0

Basic information

• Product Name: Pymetrozine
• Synonyms: Hsdb 7054;6-Methyl-4-((pyridin-3-ylMethylene)aMino)-4,5-dihydro-1,2,4-triazin-3(2H)-one;(E)-4,5-dihydro-6-Methyl-4-[(3-pyridinylMethylene)aMino]-1,2,4-triazin-3(2H)-one;4,5-Dihydro-6-Methyl-4-[(E)-(3-pyridinylMethylene)aMino]-1,2,4-triazin-3(2H)-one;A 9364A;(E)-6-Methyl-4-((pyridin-3-ylMethylene)aMino)-4,5-dihydro-1,2,4-triazin-3(2H)-one;Pymetrozine 0;Pymetrozin Solution, 100ppm
• CAS NO: 123312-89-0
• Molecular Formula: C₁₀H₁₁N₅O
• Molecular Weight: 217.23
• EINECS: 200-258-5
• Product Categories: Agro-Products;Aromatics;Heterocycles;Alpha sort;N-PPesticides&Metabolites;OthersAlphabetic;P;Pesticides;Pesticides&Metabolites;PU - PZ
• Mol File: 123312-89-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 234.4°
• Flash Point: >230 °C
• Appearance: colorless crystals
• Density: 1.33 g/cm³
• Vapor Pressure: 0Pa at 25.03℃
• Refractive Index: 1.665
• Storage Temp.: 0-6°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.90±0.40(Predicted)
• Stability: Hygroscopic
• BRN: 7814151
• CAS DataBase Reference: Pymetrozine(CAS DataBase Reference)
• NIST Chemistry Reference: Pymetrozine(123312-89-0)
• EPA Substance Registry System: Pymetrozine(123312-89-0)

Safety Data

• Hazard Codes: Xn
• Statements: 40-52/53-R52/53-R40
• Safety Statements: 36/37-61-S61-S36/37
• WGK Germany: 2
• RTECS: XZ3018620
• Hazardous Substances Data: 123312-89-0(Hazardous Substances Data)

Usage

Descriptioin

Pymetrozine is a new neuroactive insecticide. It has a remarkable selectivity for sucking insect pests, such as aphids, whiteflies, and plant hoppers, due to its systemic action. Pymetrozine is the only representative of the pyridine azomethines, a new class of insecticides. Pymetrozine has been determined to be of low acute toxicity to humans, birds, aquatic organisms, mammals, and bees. It is also not mutagenic.

Reference

J. Ausborn, H. Wolf, W. Mader, H. Kayser, The insecticide pymetrozine selectively against affects chordotonal mechanoreceptors, Journal of Experimental Biology, 2005, vol. 208, pp. 4451-4466 D. Fuog, S. J. Fergusson, C. Flückiger, Pymetrozine: A Novel Insecticide Affecting Aphids and Whiteflies, Insecticides with Novel Modes of Action, 1998, ISBN 978-3-642-08314-3

Uses

Pymetrozine ia a pyridine azomethine antifeedant. Pymetrozine is used as insecticide.

Uses

Insecticide.

Uses

Pymetrozine is a pyridine azomethine antifeedant. Pymetrozine is used as insecticide.

Definition

ChEBI: A member of the class of 1,2,4-triazines that is 4,5-dihydro-1,2,4-triazin-3(2H)-one substituted by a methyl group at position 6 and a (pyridin-3-ylmethylidene)amino group at position 4.

InChI:InChI=1/C10H11N5O/c1-8-7-15(10(16)14-13-8)12-6-9-3-2-4-11-5-9/h2-6H,7H2,1H3,(H,14,16)/b12-6+

Synthetic route

3-pyridinecarboxaldehyde (500-22-1) + 2,3,4,5-tetrahydro-3-oxo-4-amino-6-methyl-1,2,4-triazine (123313-07-5) → pymetrozine (123312-89-0)

Conditions	Yield
In ethanol at 50℃; Reflux;	92%

C10H12ClN5O → pymetrozine (123312-89-0)

Conditions	Yield
With potassium carbonate In methanol at 25 - 30℃; for 5h; Reagent/catalyst;	85%

methyl (E)-1- (2-oxopropyl)-2-(pyridin-3-ylmethylene)hydrazine-1-carboxylate → pymetrozine (123312-89-0)

Conditions	Yield
With hydrazine hydrate In tetrahydrofuran at 0 - 25℃; Cooling; Green chemistry;	70%

methyl (E)-1- (2-oxopropyl)-2-(pyridin-3-ylmethylene)hydrazine-1-carboxylate → C11H15N5O2 + pymetrozine (123312-89-0) + hydrazone of pyridine-3-carboxaldehyde (26364-02-3) + 1,4-bis(3-pyridyl)-2,3-diaza-1,3-butadiene (13362-77-1)

Conditions	Yield
With hydrazine hydrate In ethanol at 25℃;	A 28% B 37% C 14% D 15%
With hydrazine hydrate In ethanol at 80℃; Solvent;	A 36% B 16% C 21% D 18%
With hydrazine hydrate In ethanol at 80℃;	A 35% B 15% C 17% D 19%
With hydrazine hydrate In ethanol at 50℃;	A 24% B 21% C 8% D 10%

methyl (E)-1- (2-oxopropyl)-2-(pyridin-3-ylmethylene)hydrazine-1-carboxylate → C11H15N5O2 + pymetrozine (123312-89-0)

Conditions	Yield
With hydrazine hydrate In ethanol at 0 - 25℃;	A 20% B 23%

3-pyridinecarboxaldehyde (500-22-1) + 4-amino-6-methyl-3-oxo-2,3,4,5-tetrahydro-1,2,4-triazine hydrochloride → pymetrozine (123312-89-0)

Conditions	Yield
With sodium hydroxide In methanol; water

3-pyridinecarboxaldehyde (500-22-1) + 2,3,4,5-tetrahydro-3-oxo-4-amino-6-methyl-1,2,4-triazine (123313-07-5) → pymetrozine (123312-89-0)

Conditions	Yield
In methanol at 65℃; for 12h; Temperature; Green chemistry; Large scale;	2080 g

methyl (E)-2-(pyridin-3-ylmethylene)hydrazine-1-carboxylate → pymetrozine (123312-89-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 25 - 30 °C / Cooling with ice; Green chemistry 2: hydrazine hydrate / tetrahydrofuran / 0 - 25 °C / Cooling; Green chemistry View Scheme

methyl (E)-2-(pyridin-3-ylmethylene)hydrazine-1-carboxylate → C11H15N5O2 + pymetrozine (123312-89-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 25 - 30 °C / Cooling with ice; Green chemistry 2: hydrazine hydrate / ethanol / 0 - 25 °C View Scheme

methanol (67-56-1) + pymetrozine (123312-89-0) → 5-Methoxy-6-methyl-4-{[1-pyridin-3-yl-meth-(E)-ylidene]-amino}-4,5-dihydro-2H-[1,2,4]triazin-3-one

Conditions	Yield
With tetraethylammonium tosylate for 24h; current (6 V, 200 mA), graphite electrodes;	30%

(2,4-dinitro-phenyl)-hydrazine (119-26-6) + pymetrozine (123312-89-0) → pyridine-3-carbaldehyde-(2,4-dinitro-phenylhydrazone) (1834-93-1) + 2,3,4,5-tetrahydro-3-oxo-4-amino-6-methyl-1,2,4-triazine (123313-07-5)

Conditions	Yield
In ethanol

pymetrozine (123312-89-0) → 5-Hydroxy-6-methyl-4-{[1-pyridin-3-yl-meth-(E)-ylidene]-amino}-4,5-dihydro-2H-[1,2,4]triazin-3-one

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; oxygen; iron(II) sulfate 1.) -78 deg C, 150 min, -78 deg C to 25 deg C, 8 h, rt, overnight, THF, cyclohexane; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: 30 percent / tetraethylammonium p-toluenesulfonate / 24 h / current (6 V, 200 mA), graphite electrodes 2: 53 percent / aq. citric acid / tetrahydrofuran / Ambient temperature; overnight View Scheme

Upstream product

• 123312-57-2 2,8-Diazatetracyclo[4.3.0.03,9.04,7]nonane(9CI) 
• 123312-54-9 N,N-DIMETHYL-N,N-DISTEARYLAMMONIUM HYDROGEN SULFATE 
• 123312-25-4 2-(3-METHOXYPHENYL)BUTAN-1-AMINE 
• 123312-22-1 (4-CHLOROPHENYL)(CYCLOPROPYL)METHYLAMINE 
• 123312-21-0 cyano(3-phenoxyphenyl)methyl [2-(4-bromophenyl)propan-2-yl]carbamate 
• 123312-20-9 cyano(3-phenoxyphenyl)methyl [(4-chlorophenyl)(cyclopropyl)methyl]carbamate 
• 123312-19-6 cyano(3-phenoxyphenyl)methyl [1-(4-methoxyphenyl)propyl]carbamate 
• 123312-18-5 cyano(3-phenoxyphenyl)methyl [1-(4-chlorophenyl)propyl]carbamate 
• 123312-17-4 cyano(3-phenoxyphenyl)methyl [1-(4-chlorophenyl)ethyl]carbamate 
• 123312-16-3 cyano(3-phenoxyphenyl)methyl (4-chlorobenzyl)carbamate 
• 123312-15-2 cyano(3-phenoxyphenyl)methyl (1-phenylethyl)propan-2-ylcarbamate 
• 123312-14-1 cyano(3-phenoxyphenyl)methyl (4-chlorobenzyl)propan-2-ylcarbamate 
• 123312-13-0 cyano(3-phenoxyphenyl)methyl (4-chlorophenyl)propan-2-ylcarbamate 
• 123312-12-9 cyano(3-phenoxyphenyl)methyl 1,3-benzodioxol-5-yl(propan-2-yl)carbamate 

Downstream Products

• 1233131-04-8 1-Piperazineethanol, α-(5-chloro-6-Methoxy-2-naphthalenyl)-4-(1-phenylethyl)-β-propyl-, hydrochloride, hydrate (1:2:2) 
• 123313-11-1 1,2,4-Triazin-3(2H)-one,4-amino-4,5-dihydro-6-(1-methylethyl)-(9CI) 
• 1233131-18-4 4-(quinoliN-8-yl)phenylbornic acid,pinacol ester 
• 123313-61-1 2-chloro-5-[(2,4,4-trimethylcyclohex-1-en-1-yl)methyl]phenazin-1(5H)-one 
• 1233143-48-0 2-Thia-6-azaspiro[3.3]heptane hemioxalate 
• 123314-39-6 H-CIT-AMC HBR 
• 1233145-49-7 1-PiperidineacetaMide, 4-[3-Methoxy-4-[[7-(2-Methoxyphenyl)pyrrolo[2,1-f][1,2,4]triazin-2-yl]aMino]phenyl]- 
• 123316-14-3 Biliverdin 
• 123316-60-9 azidoioxynil 
• 123316-61-0 2-(2,4-dimethoxyphenyl)-5-hydroxy-7,8-dimethoxy-chromen-4-one 
• 123316-64-3 2'-O-Methylhelichrysetin 
• 123316-86-9 1,1'-DIOCTYL-3,3,3',3'-TETRAMETHYLINDOCARBOCYANINE IODIDE 
• 123317-51-1 2-(4-nitrobenzyl)-1,4,7,10-tetraazacyclododecane-N,N',N'',N'''-tetraacetic acid 
• 123317-52-2 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid, 2-[(4-aMinophenyl)Methyl]- 

Recommend Products

• 500-22-1  3-pyridinecarboxaldehyde 
• 123313-07-5  2,3,4,5-tetrahydro-3-oxo-4-amino-6-methyl-1,2,4-triazine 
• 26364-02-3  hydrazone of pyridine-3-carboxaldehyde 
• 13362-77-1  1,4-bis(3-pyridyl)-2,3-diaza-1,3-butadiene 
• 1834-93-1  pyridine-3-carbaldehyde-(2,4-dinitro-phenylhydrazone) 
• 119-26-6  (2,4-dinitro-phenyl)-hydrazine