1. Full Identification & Nomenclature

Core Registry Data

• Standard Short Name: Triazinamide / Pymetrozine Intermediate P4
• CAS Registry Number: 136738-23-3
• Full IUPAC Name: 4-Acetylamino-6-methyl-3-oxo-2,3,4,5-tetrahydro-1,2,4-triazine
• Systematic Alias: N-(6-methyl-3-oxo-2,5-dihydro-1,2,4-triazin-4(3H)-yl)acetamide
• Chinese Name: 4 – 乙酰氨基 – 6 – 甲基 – 3 – 氧代 – 2,3,4,5 – 四氢 – 1,2,4 – 三嗪
• HS Customs Code: 2933699099 (Triazine heterocyclic fine chemicals)
• EINECS: Unassigned

Molecular Coding (Copyable Text)

• Molecular Formula: C₆H₁₀N₄O₂
• Exact Molecular Weight: 170.169 g/mol
• SMILES: CC(=O)NN1CC(C)=NNC1=O
• InChI: 1S/C6H10N4O2/c1-4-3-10(9-5(2)11)6(12)8-7-4/h3H2,1-2H3,(H,8,12)(H,9,11)
• InChIKey: NCSCAWXVGUIUEY-UHFFFAOYSA-N

Triazinamide Molecular Structure

2. Molecular Structural Characteristics

1. Heterocyclic Backbone: Saturated aliphatic 1,2,4-tetrahydrotriazine six-membered ring, non-aromatic, distinct from fully conjugated aromatic 1,3,5-triazine (melamine)
2. Ring Substituent Distribution
   • C6 position: Methyl group (-CH₃)
   • C3 position: Lactam carbonyl (C=O), forming cyclic amide structure
   • N4 ring nitrogen: Acetylamino reactive side chain (-NH-COCH₃)
3. Structural Advantages
   • Abundant hydrogen bond donors & acceptors (4 ring N, 2 carbonyl O, 2 amide NH)
   • Low steric hindrance on N4 site, easy to conduct aldehyde condensation
   • Flexible saturated ring without aromatic π-conjugation, mild reaction conditions required for derivatization

3. Complete Physical & Chemical Properties

Physical Index

表格

Parameter	Standard Value	Supplementary Note
Appearance	White / off-white crystalline powder	Industrial purified solid
Melting Point	218–224 °C	Decomposes immediately upon melting
Thermal Decomposition Threshold	≥220 °C	Releases NH3, N2 and nitrogenous volatile organics
LogP (Partition Coefficient)	-0.708	Strongly hydrophilic
Predicted Density	1.43 g/cm³	Computational simulation value
pKa	11.22	Weak acidity from lactam N-H
Hygroscopy	Low	No deliquescence under normal humidity
Solubility	Soluble in hot water, DMF, DMSO; slightly soluble in methanol; insoluble in ethers, alkanes	Polar solvent selective dissolution

Core Chemical Reactivity

1. Acidic HydrolysisCleaves terminal acetyl group to produce 4-amino-6-methyl-3-oxo-tetrahydrotriazine, the direct precursor for pymetrozine synthesis.
2. Condensation & Reductive Amination (Industrial Core Reaction)Acetylamino N-H condenses with pyridine-3-carboxaldehyde to form Schiff base; subsequent catalytic reduction yields technical-grade pymetrozine insecticide.
3. Alkaline DegradationStrong base with heating triggers ring-opening cleavage of the lactam structure.
4. Salt FormationCombines with strong mineral acids (HCl, H2SO4) via ring N protonation to form water-soluble inorganic salts.
5. Oxidation ResistanceStable under mild oxidation; high-temperature air or H2O2 oxidizes saturated ring into unsaturated triazinone impurities.

4. Industrial Synthetic Manufacturing Routes

Main Mass-Production Route (Global Standard Process)

1. Cyclization Step: Methylthiosemicarbazide reacts with ethyl pyruvate to generate triazinamine crude intermediate
2. Acetylation Step: Reaction with acetic anhydride / acetyl chloride under triethylamine catalysis at 40–60 °C
3. Purification: Recrystallization with hot water to raise purity
4. Post-treatment: Filtration + low-temperature vacuum drying to obtain finished crystalline powder

Lab Minor Route

Cyanamide + urea thermal cyclization followed by acetylation; low total yield, only for small laboratory trial batches, not suitable for large-scale industrial output.

5. Industrial Quality Control Specifications

1. HPLC Purity
   • Technical industrial grade: ≥99.0%
   • High-purity fine intermediate grade: ≥99.5%
2. Moisture Content: ≤0.3%
3. Hot Water Insoluble Residue: ≤0.1%
4. Heavy Metal Impurities (Pb, As, Cd): <10 ppm
5. Residual Acetic Acid: ≤0.2%

6. Application Field Analysis

Dominant Application: Penultimate Intermediate of Pymetrozine Insecticide

Triazinamide is the mandatory upstream raw material for pymetrozine, a selective systemic agrochemical developed for piercing-sucking pest control:

• Target pests: Aphids, whiteflies, rice planthoppers, leafhoppers on grain, vegetable and cash crops
• Insecticidal mechanism: Blocks serotonin transmission in insect stylets, causing permanent feeding cessation

Secondary Research & Lab Applications

1. Medicinal chemistry building block for nitrogen heterocyclic drug candidates
2. Ligand precursor for metal coordination catalyst research
3. Nitrogen-rich monomer for polyamide and COF (covalent organic framework) lab synthesis

7. Safety, Handling & Storage Guidelines

Hazard Profile

• Mild irritant to skin, eyes and respiratory tract; avoid dust inhalation and direct contact
• Thermal decomposition generates toxic ammonia and nitrogen oxide fumes
• Non-flammable solid, but accelerates combustion when mixed with strong oxidants

Personal Protection

Wear dust respirator, chemical-resistant gloves and safety goggles during weighing, feeding and synthesis operations.

Storage & Transportation

• Packaging: 25kg woven bags lined with PE inner film, sealed tightly
• Storage environment: Cool, dry, ventilated warehouse; segregate from oxidants, strong acids and food chemicals
• Transport classification: General industrial chemical, no dangerous goods label required; shield from rain and high temperature

Waste Disposal

Solid waste sent to dedicated chemical incinerators with tail gas absorption system; liquid wastewater neutralized before discharge complying with local environmental standards.

8. Market & Production Overview

• Global monthly industrial capacity: ~100 metric tons
• Bulk FOB pricing: ≥1000kg USD 4–6/kg; small batches (1–200kg) USD 35–40/kg
• Major manufacturers: Fine chemical factories in Jiangsu, Zhejiang and Shandong (China), supplying global pymetrozine manufacturers