Дезаминометамитрон

Description

Desaminomethamitron is a derivative of 1,2,4-triazine, in which the amino group of the original metamitron molecule is replaced by a hydrogen atom. The compound is formed as the main product of photodegradation of metamitron when aqueous solutions of this herbicide are exposed to sunlight, that is, it is an environmental marker of the decomposition of the active substance in the environment - soil and surface waters.

Basic Attributes

• CAS No: 36993-94-9
• Chemical formula: C10H9N3O
• Molecular Weight: 187.201
• Exact weight: 187.20
• DSSTox ID: DTXSID30190483
• PSA specifications: 53.8
• XLogP3: 1

Physico-chemical characteristics

• Melting point: 263–265 °C (solvent methanol)

Parent herbicide

Metamitron is a triazinone herbicide that has been widely used in the European Union since the mid-1970s as a selective agent for protecting sugar beet crops from annual dicotyledonous and some cereal weeds. It inhibits photosynthesis of weeds by blocking electron transfer in photosystem II. When decomposed by sunlight, metamitron loses its amino group and turns into desaminomethamitron.

Scope of application

• reference standard for environmental monitoring of metamitron residues in soil and water
• marker of photochemical degradation of triazinone herbicides
• analytical methodology for monitoring pesticide residues using HPLC and mass spectrometry methods
• research into the transformation pathways of agricultural chemicals in the environment

Chemical class

Belongs to derivatives of 1,2,4-triazin-5(2H)-one - a heterocyclic class to which other triazinone herbicides (metamitron, metribuzin) belong. The absence of an amino group at a position critical for binding to the D1 protein of photosystem II explains why deaminomethamitron loses the herbicidal activity of the parent compound and is considered primarily as a transformation product rather than an active substance.

Implications for environmental monitoring

When registering and re-evaluating pesticides, regulatory authorities require that, along with the original active substance, the products of its transformation in soil, water and plants are also assessed. Desaminomethamitron in this context serves as one of the key markers: its detection in water samples indicates a photochemical pathway of metamitron decomposition, different from microbial degradation in the soil, which is important when assessing the environmental risks of using the herbicide near water bodies.

Synonyms

1,2,4-Triazin-5(2H)-one, 3-methyl-6-phenyl-; 3-Methyl-6-phenyl-1,2,4-triazin-5(2H)-one; 3-Methyl-6-phenyl-1,2,4-triazin-5-one; Deaminometatron; Metamitron-desamino; 3-Methyl-6-phenyl-1,2,4-triazin-5(4H)-one; 3-Methyl-6-phenyl-4,5-dihydro-1,2,4-triazin-5-one; 3-Methyl-6-phenyl-4H-[1,2,4]triazin-5-one; 3-Methyl-6-phenyl-2H-1,2,4-triazin-5-one; 3-Methyl-6-phenyl-1,2,4-triazin-5-ol.

Storage and transportation conditions

Store in a dry place, protected from light, at room temperature in an airtight container. No special transport requirements have been established for the substance as an analytical standard.