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123312-89-0

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123312-89-0 Usage

Description

Pymetrozine is a pyridine azomethine antifeedant and a member of the class of 1,2,4-triazines. It is characterized by the presence of a methyl group at position 6 and a (pyridin-3-ylmethylidene)amino group at position 4. Pymetrozine is a selective insecticide that targets specific pests without causing harm to beneficial insects or the environment.

Uses

Used in Agriculture:
Pymetrozine is used as an insecticide for controlling various pests, particularly aphids, whiteflies, and leafhoppers. It works by inhibiting the feeding behavior of these pests, leading to their eventual starvation and death. This selective action makes Pymetrozine an environmentally friendly alternative to traditional insecticides.
Used in Horticulture:
In horticulture, Pymetrozine is used as an insecticide to protect ornamental plants and crops from damage caused by sucking pests such as aphids and whiteflies. Its selective nature ensures that beneficial insects, pollinators, and natural predators are not harmed, promoting a balanced ecosystem and sustainable pest management.
Used in Integrated Pest Management (IPM):
Pymetrozine is an essential component of Integrated Pest Management strategies, which aim to reduce the reliance on chemical pesticides and promote a more sustainable approach to pest control. By targeting specific pests and minimizing harm to beneficial organisms, Pymetrozine contributes to the overall success of IPM programs.
Used in Public Health:
Pymetrozine can also be used in public health applications to control pests that transmit diseases or cause nuisances. Its selective action and low toxicity make it suitable for use in areas where human exposure is a concern, such as residential and recreational settings.

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

Check Digit Verification of cas no

The CAS Registry Mumber 123312-89-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,3,3,1 and 2 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 123312-89:
(8*1)+(7*2)+(6*3)+(5*3)+(4*1)+(3*2)+(2*8)+(1*9)=90
90 % 10 = 0
So 123312-89-0 is a valid CAS Registry Number.
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+

123312-89-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name pymetrozine

1.2 Other means of identification

Product number -
Other names Pymetrozine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:123312-89-0 SDS

123312-89-0Synthetic route

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

2,3,4,5-tetrahydro-3-oxo-4-amino-6-methyl-1,2,4-triazine
123313-07-5

2,3,4,5-tetrahydro-3-oxo-4-amino-6-methyl-1,2,4-triazine

pymetrozine
123312-89-0

pymetrozine

Conditions
ConditionsYield
In ethanol at 50℃; Reflux;92%
C10H12ClN5O

C10H12ClN5O

pymetrozine
123312-89-0

pymetrozine

Conditions
ConditionsYield
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

methyl (E)-1- (2-oxopropyl)-2-(pyridin-3-ylmethylene)hydrazine-1-carboxylate

pymetrozine
123312-89-0

pymetrozine

Conditions
ConditionsYield
With hydrazine hydrate In tetrahydrofuran at 0 - 25℃; Cooling; Green chemistry;70%
methyl (E)-1- (2-oxopropyl)-2-(pyridin-3-ylmethylene)hydrazine-1-carboxylate

methyl (E)-1- (2-oxopropyl)-2-(pyridin-3-ylmethylene)hydrazine-1-carboxylate

A

C11H15N5O2

C11H15N5O2

B

pymetrozine
123312-89-0

pymetrozine

C

hydrazone of pyridine-3-carboxaldehyde
26364-02-3

hydrazone of pyridine-3-carboxaldehyde

D

1,4-bis(3-pyridyl)-2,3-diaza-1,3-butadiene
13362-77-1

1,4-bis(3-pyridyl)-2,3-diaza-1,3-butadiene

Conditions
ConditionsYield
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

methyl (E)-1- (2-oxopropyl)-2-(pyridin-3-ylmethylene)hydrazine-1-carboxylate

A

C11H15N5O2

C11H15N5O2

B

pymetrozine
123312-89-0

pymetrozine

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 0 - 25℃;A 20%
B 23%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

4-amino-6-methyl-3-oxo-2,3,4,5-tetrahydro-1,2,4-triazine hydrochloride

4-amino-6-methyl-3-oxo-2,3,4,5-tetrahydro-1,2,4-triazine hydrochloride

pymetrozine
123312-89-0

pymetrozine

Conditions
ConditionsYield
With sodium hydroxide In methanol; water
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

2,3,4,5-tetrahydro-3-oxo-4-amino-6-methyl-1,2,4-triazine
123313-07-5

2,3,4,5-tetrahydro-3-oxo-4-amino-6-methyl-1,2,4-triazine

pymetrozine
123312-89-0

pymetrozine

Conditions
ConditionsYield
In methanol at 65℃; for 12h; Temperature; Green chemistry; Large scale;2080 g
methyl (E)-2-(pyridin-3-ylmethylene)hydrazine-1-carboxylate

methyl (E)-2-(pyridin-3-ylmethylene)hydrazine-1-carboxylate

pymetrozine
123312-89-0

pymetrozine

Conditions
ConditionsYield
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

methyl (E)-2-(pyridin-3-ylmethylene)hydrazine-1-carboxylate

A

C11H15N5O2

C11H15N5O2

B

pymetrozine
123312-89-0

pymetrozine

Conditions
ConditionsYield
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

methanol

pymetrozine
123312-89-0

pymetrozine

5-Methoxy-6-methyl-4-{[1-pyridin-3-yl-meth-(E)-ylidene]-amino}-4,5-dihydro-2H-[1,2,4]triazin-3-one

5-Methoxy-6-methyl-4-{[1-pyridin-3-yl-meth-(E)-ylidene]-amino}-4,5-dihydro-2H-[1,2,4]triazin-3-one

Conditions
ConditionsYield
With tetraethylammonium tosylate for 24h; current (6 V, 200 mA), graphite electrodes;30%
(2,4-dinitro-phenyl)-hydrazine
119-26-6

(2,4-dinitro-phenyl)-hydrazine

pymetrozine
123312-89-0

pymetrozine

A

pyridine-3-carbaldehyde-(2,4-dinitro-phenylhydrazone)
1834-93-1

pyridine-3-carbaldehyde-(2,4-dinitro-phenylhydrazone)

B

2,3,4,5-tetrahydro-3-oxo-4-amino-6-methyl-1,2,4-triazine
123313-07-5

2,3,4,5-tetrahydro-3-oxo-4-amino-6-methyl-1,2,4-triazine

Conditions
ConditionsYield
In ethanol
pymetrozine
123312-89-0

pymetrozine

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

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

Conditions
ConditionsYield
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

123312-89-0Relevant articles and documents

Method for preparing pymetrozine

-

Paragraph 0051; 0055; 0060; 0065, (2018/11/22)

The invention discloses a method for preparing pymetrozine with an aim to provide a synthesis method short in reaction route of the pymetrozine, small in environmental pollution and simple in technology operation, and belongs to the technical field of organic synthesis. The method includes the steps of 1), allowing dimethyl carbonate serving as a raw material to be subjected to hydrazinolysis withhydrazine hydrate to obtain carbazide; 2), subjecting carbazide and smoke aldehyde to condensation reaction to obtain (E)-N'-(pyridine-3-kiya methyl) hydrazine carbon hydrazide; 3), subjecting (E)-N'-( pyridine-3-kiya methyl) hydrazine carbon hydrazide and chloroacetone to condensation reaction to obtain (E)-N'-(Z)-1-chloropropyl-2-subunit)-2-(pyridine-3-kiya methyl) diazanyl-1-carbohydrazide; 4), subjecting (E)-N'-(Z)-1-chloropropyl-2-subunit)-2-(pyridine-3-kiya methyl) diazanyl-1-carbohydrazide to ring formation under the alkaline condition to obtain the pymetrozine.

A high-efficiency green pymetrozine preparation method

-

Paragraph 0014; 0030; 0035; 0040-0042; 0043-0045; 0046-0048, (2017/08/25)

The invention discloses a high-efficiency and green method for preparing pymetrozine. According to the method, a byproduct methyl acetate produced in a pymetrozine condensation step serves as a raw material and replaces ethyl acetate in a traditional process for synthesizing acethydrazide, and the produced byproduct methanol can serve as a solvent in a subsequent step, so that the byproduct is recycled, and the raw material utilization rate is improved. Hydrogen chloride or concentrated hydrochloric acid in a traditional process is replaced by adopting a saturated hydrogen chloride methanol solution in the condensation step, and moisture in the system is avoided, so that amino triazone is subjected to a hydrolysis reaction, and byproducts are basically eliminated. According to the method, the yield of the product and the utilization rate of the hydrogen chloride are improved, the reaction time is shortened, emission of wastewater and waste gas is reduced, the comprehensive production cost is reduced, and better conditions are created for industrial large-scale production of the product.

Active agent combinations

-

, (2008/06/13)

The novel active compound combinations of extracts from seeds of the neem tree and the active compounds of groups (B) to (F) listed in the description have very good insecticidal and acaricidal properties.

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