TRI-ALLATE

Tri-allate is a selective, soil-acting thiocarbamate herbicide used before crop emergence to control wild oats and other susceptible annual grasses.
Tri-allate works in the narrow zone through which weed shoots pass, so incorporation quality and treated-layer placement are as important as the quantity of active ingredient applied.
Tri-allate is commercially supplied as technical active, emulsifiable concentrate and soil-applied granules, with each form creating a different combination of transfer, distribution, volatility and application-control requirements.

CHEMICAL IDENTITY AND COMMON NAMES

Tri-allate is the approved common name for S-(2,3,3-trichloroallyl) diisopropylthiocarbamate.
The systematic name S-(2,3,3-trichloroprop-2-en-1-yl) N,N-di(propan-2-yl)carbamothioate describes a tertiary thiocarbamate carrying a chlorinated allylic group through sulfur.
Triallate is the established unhyphenated spelling, while Triallat, Tri-allat, Triamyl and Trillate occur as recognised alternative names or spelling forms.
CP 23426 is a historical development code associated with the same active substance.

Synonyms and Common Names: Tri-allate, Triallate, Triallat, Tri-allat, Triamyl, Trillate, CP 23426, S-(2,3,3-trichloroprop-2-en-1-yl) N,N-di(propan-2-yl)carbamothioate, S-(2,3,3-trichloroallyl) diisopropylcarbamothioate, S-2,3,3-trichloroallyl diisopropylthiocarbamate, S-2,3,3-trichloroallyl N,N-diisopropylthiocarbamate, S-(2,3,3-trichloro-2-propenyl) bis(1-methylethyl)carbamothioate, S-(2,3,3-trichloro-2-propen-1-yl) N,N-bis(1-methylethyl)carbamothioate, 2,3,3-trichloroallyl N,N-diisopropylthiocarbamate, carbamic acid, diisopropylthio-, S-(2,3,3-trichloroallyl) ester, N,N-diisopropylthiocarbamic acid S-(2,3,3-trichloro-2-propenyl) ester, 2-propene-1-thiol, 2,3,3-trichloro-, diisopropylcarbamate, carbamothioic acid, bis(1-methylethyl)-, S-(2,3,3-trichloro-2-propenyl) ester, diisopropyltrichloroallylthiocarbamate, N,N-diisopropyl-2,3,3-trichloroallylthiol carbamate

TECHNICAL IDENTIFICATION

CAS Number: 2303-17-5
EC / EINECS Number: 218-962-7
CLP Index Number: 006-039-00-X
CIPAC Number: 97
Molecular Formula: C10H16Cl3NOS
Molar Mass: 304.66 g/mol
Chemical Class: Chlorinated S-alkyl thiocarbamate herbicide
UNII: A9S097HS99
InChIKey: MWBPRDONLNQCFV-UHFFFAOYSA-N
Canonical SMILES: CC(C)N(C(C)C)C(=O)SCC(=C(Cl)Cl)Cl

PHYSICAL AND CHEMICAL PROFILE

Appearance: Colourless crystals when purified and yellow to brown material in technical form
Physical State: Low-melting solid or clear to amber oily liquid, depending on temperature
Melting Range: Approximately 29–33.5 °C
Boiling Behaviour: Approximately 117 °C at 0.3 mmHg, with decomposition occurring before a practical atmospheric boiling point is reached
Thermal Decomposition: Begins above approximately 200 °C
Density: Approximately 1.27 g/mL at 25 °C
Vapour Pressure: 12 mPa at 20 °C and approximately 16 mPa at 25 °C
Henry’s Law Constant: Approximately 0.89 Pa·m³/mol at 25 °C
Water Solubility: Approximately 4.1 mg/L at 20 °C and pH 7
Organic-Solvent Solubility: Highly soluble in acetone, ethanol, methanol, xylene, ether, ethyl acetate and hydrocarbon solvents
Partition Coefficient: log Kow approximately 4.06 at 20 °C and pH 7
Dissociation: Non-ionising under ordinary environmental and formulation conditions
Hydrolysis: Stable at pH 4 and pH 7, with a half-life of approximately 52 days at pH 9 and 25 °C
Photochemical Behaviour: Direct aqueous photolysis is limited because Tri-allate has little environmentally relevant ultraviolet absorption

Tri-allate changes phase close to normal warehouse and processing temperatures.
A technical batch may therefore be solid, partly molten or fully liquid without any change in chemical identity.
Transfer systems for technical active account for this low melting range through controlled warming, suitable pumps and protection against local overheating.

BIOACTIVATION BEFORE LIPID-SYNTHESIS INHIBITION

Tri-allate belongs to current Herbicide Resistance Group 15, the inhibitors of very-long-chain fatty-acid synthesis.
Older classification systems and some legacy labels identify the same thiocarbamate mode of action as Group 8, HRAC Group N or HRAC Group K3.
The numbering difference does not create a new resistance group, and all of these descriptions refer to the same Tri-allate site-of-action family.

Susceptible seedlings first oxidise Tri-allate to a more phytotoxic sulfoxide.
The activated form disrupts fatty-acid elongation and the production of very-long-chain fatty acids needed for cell membranes, cuticular waxes and normal shoot development.
Affected grasses show restricted coleoptile and first-leaf growth, abnormal thickening or twisting, and failure to emerge successfully through the soil surface.

Uptake occurs mainly mainly through the emerging shoot from the dissolved and vapour phases in the treated soil zone.
Root effects are secondary to the injury at rapidly developing shoot tissues.
Because Tri-allate acts during germination and emergence, it does not provide the foliar rescue function expected from a post-emergence grass herbicide.

Reduced bioactivation is a documented resistance mechanism in wild oats.
Some resistant populations convert Tri-allate to its sulfoxide more slowly even though their tissues remain sensitive to the activated compound.
This unusual mechanism makes field history, population sensitivity and resistance management particularly important when evaluating performance.

PRODUCTION AND TECHNICAL-ACTIVE COMPOSITION

A commercial synthesis can form a diisopropylthiocarbamate salt from diisopropylamine and carbonyl sulfide under alkaline conditions.
Condensation of that intermediate with a tetrachloropropene precursor establishes the sulfur-linked 2,3,3-trichloroallyl group and produces Tri-allate.
Purification removes residual chlorinated intermediates, sulfur-containing coupling products, amine-derived material and process solvent.

Technical Tri-allate is commonly produced at 95–97% active content.
The European active-substance specification establishes a minimum purity of 940 g/kg and limits N-nitrosodiisopropylamine to 0.02 mg/kg.
This very low nitrosamine limit makes control of amine quality, nitrosating contamination, process conditions and sensitive trace analysis part of technical-active manufacturing.

Recognised process-related impurities include bis(2,3,3-trichloroallyl) sulfide, the corresponding disulfide, hexachloropropane, a dichloroallyl analogue and an N-ethyl-N-isopropyl thiocarbamate analogue.
Their pattern can indicate precursor quality, reaction selectivity and purification efficiency.
Technical procurement therefore combines total active assay with a defined impurity profile rather than treating colour and physical state as sufficient release criteria.

APPLICATIONS AND INDUSTRIES

Wild-oat control in cereal production

Tri-allate is used primarily for pre-emergence control of wild oats in spring wheat, winter wheat, durum wheat, barley, rye and triticale where authorised.
Early control protects the cereal stand from competition during crop establishment and reduces dependence on later foliar grass-herbicide treatments.
Tri-allate can be applied before planting and incorporated mechanically, incorporated during sowing, or applied after sowing but before emergence under formulation-specific label directions.

Black-grass, meadow-grass and ryegrass programmes

Tri-allate also contributes to authorised programmes targeting black-grass, annual meadow-grass, annual ryegrass and selected brome species.
Performance against these weeds depends on population sensitivity, germination depth, incorporation uniformity and access to the treated soil zone.
Tri-allate resistance has been documented in wild oats and annual ryegrass, so a previously effective field history does not remove the need for current resistance planning.

Pulse and oilseed rotations

Registered crop uses in different markets include peas, lentils, chickpeas, flax or linseed, canola, mustard, safflower and lupins.
These uses retain the same soil-acting principle but differ in crop tolerance, sowing system, residue restrictions and rotational-crop requirements.
Crop seed placement and the separation between seed and treated zone are especially important where selectivity depends partly on physical position.

Sugar beet and selected specialist crops

Tri-allate has also been authorised in particular jurisdictions for sugar beet and selected brassica, carrot, onion or other specialist-crop systems.
These are registration-defined uses rather than a general extension of cereal recommendations.
The appropriate product form, timing, incorporation method and crop restrictions are taken from the authorised label for that market.

Resistance-management systems

Tri-allate provides a pre-emergence Group 15 component for programmes that combine different herbicide sites of action with non-chemical control.
Seed-bank reduction, competitive crops, delayed sowing where agronomically suitable, harvest weed-seed control, cultivation and effective post-emergence options reduce reliance on one activation pathway.
Repeated use of Tri-allate alone against dense populations increases selection pressure for reduced activation, enhanced detoxification and other resistance mechanisms.

Formulation manufacture

Technical Tri-allate is formulated mainly as emulsifiable concentrate or granules for broadcast application and soil incorporation.
Emulsifiable concentrate provides rapid metering and spray distribution, while granular formulations place active on a solid carrier that can be spread without preparing a spray emulsion.
Formulation choice changes volatility management, application equipment, worker-exposure profile, package type and the quality tests required for release.

Residue and environmental laboratories

Analytical-grade Tri-allate supports residue analysis in grain, plant tissue, soil, water and sediment.
Parent-only monitoring is supplemented in advanced fate studies by measurement of 2,3,3-trichloropropene sulfonic acid and diisopropylamine.
The parent and acidic metabolite require different extraction and chromatographic conditions because one is hydrophobic and neutral while the other is strongly polar.

FORMULATION PATHS: EMULSIFIABLE CONCENTRATE OR GRANULE

An emulsifiable concentrate dissolves Tri-allate in an organic solvent with surfactants that form a fine emulsion after dilution in water.
The formulation must remain homogeneous in its package, emulsify across relevant water hardness and temperature, resist excessive creaming or oil separation and retain active content during storage.
Because the active melts near ambient temperature, solvent capacity must remain adequate during cold storage as well as normal processing.

Granular products commonly contain approximately 10–15% Tri-allate on a mineral or engineered carrier.
Granule-size distribution, active uniformity, dust generation, attrition resistance, bulk density and flowability determine whether the field receives an even dose.
Excess fines raise inhalation and segregation concerns, while oversized or fragile granules can create streaking and poor metering.

The two formulation routes should not be assessed by active concentration alone.
An emulsifiable concentrate requires solvent compatibility, emulsion performance, flash-point and pourability data, whereas a granular product requires carrier, dust, particle-size, attrition and spreading data.
Both forms require active-content uniformity, storage stability and a packaging system that preserves physical performance.

SOIL, WEATHER AND APPLICATION WINDOW

Tri-allate performs best when the active is distributed evenly through a prepared seedbed and the target grasses germinate into that treated layer.
Moisture after incorporation supports redistribution and weed germination, while prolonged dryness can delay both activation of the weed population and contact with the herbicide.
Cool or dry conditions can also extend soil persistence and influence rotational-crop planning.

Heavy crop residue can intercept liquid spray and prevent part of the dose from reaching mineral soil.
Granules may offer a different placement profile in high-residue systems, but carrier distribution and incorporation still control the final treated zone.
Cloddy seedbeds, pronounced ridges and variable cultivation depth create local underdosing even when the field-average application is correct.

Tank or sequence partners are selected by authorised label, physical compatibility, soil-placement requirement and resistance objective.
A companion herbicide does not compensate for poor Tri-allate incorporation if the two active ingredients occupy different effective soil zones.
Application planning therefore begins with weed-germination biology and tillage geometry rather than with mixture convenience.

GRADE SELECTION AND PROCUREMENT LOGIC

Technical-active buyers evaluate Tri-allate assay, manufacturing-impurity profile, nitrosamine control, appearance, melting behaviour, water, residual solvent and batch consistency.
The intended formulation process also determines whether low-temperature phase behaviour, colour or pumpability requires a tighter internal operating range.
Regulated formulation manufacture additionally requires manufacturing-source identity and dossier-compatible impurity information.

Emulsifiable-concentrate procurement specifies active concentration, solvent system, density, flash point, pH, emulsion stability, persistent foam, low-temperature stability, accelerated storage and package compatibility.
Granular procurement specifies active concentration, carrier type, particle-size range, bulk density, dust, attrition resistance, flow rate, storage stability and uniformity between samples.
Destination country, registered crops, weed spectrum, application method and package size complete the commercial selection.

Analytical reference material is supplied as a neat standard or accurately prepared solution for instrument calibration.
Reference-material procurement focuses on chemical identity, purity assignment, uncertainty, solvent, concentration, expiry control and storage condition rather than agricultural formulation performance.
Separate standards for Tri-allate, TCPSA and DIPA support a complete residue or environmental method.

QUALITY CONTROL AND DOCUMENTATION

Gas chromatography with flame-ionisation detection is suitable for routine Tri-allate assay, while gas chromatography with mass-spectrometric detection strengthens identity and impurity assignment.
Electron-capture detection provides high sensitivity for the chlorinated parent in residue work, and liquid chromatography with tandem mass spectrometry can measure Tri-allate and selected metabolites after appropriate extraction.
Infrared and nuclear magnetic resonance spectroscopy confirm the thiocarbamate and trichloroallyl structure.

Trace nitrosamine determination requires a dedicated, highly sensitive method with contamination control and matrix-matched quantitation.
TCPSA analysis commonly uses polar or ion-exchange sample preparation, while parent Tri-allate is efficiently recovered into an organic phase or reversed-phase sorbent.
DIPA requires a method designed for a small, basic and highly water-soluble amine rather than the parent-herbicide procedure.

The Certificate of Analysis records the released batch, active assay and grade-specific quality parameters.
The Technical Data Sheet explains product form and performance-related characteristics, and the Safety Data Sheet covers classification, controls, transport and emergency measures for the supplied composition.
Regulatory supply files additionally connect technical source, relevant impurities, formulation composition, analytical methods and destination-market registration.

SAFETY AND OCCUPATIONAL CONTROL

Tri-allate is harmful if swallowed, may cause an allergic skin reaction, may damage organs through prolonged or repeated exposure and is very toxic to aquatic life with long-lasting effects.
The harmonised hazard statements are H302, H317, H373, H400 and H410, with the signal word Warning.
Repeated-exposure findings identify the liver, kidneys and nervous system as important toxicological targets.

Tri-allate should not be treated toxicologically like a cholinesterase-inhibiting carbamate insecticide merely because both names contain the word carbamate.
Tri-allate does not exert its characteristic toxicity by inhibiting blood or brain cholinesterase.
The pesticide still requires strong occupational controls because ingestion, repeated contact, mist, vapour and granular dust create relevant exposure routes.

Closed transfer, local exhaust and mechanically assisted charging reduce exposure during technical-active and formulation handling.
Chemical-resistant gloves, protective clothing and eye protection are used for routine work, with face and respiratory protection added for dust, aerosol, vapour or spill conditions.
Sensitised individuals can react to very small subsequent skin exposures, making contaminated clothing and surfaces an important control point.

The toxicological dossier contains an unresolved genotoxicity question for the parent active and nitrosamine-related concerns associated with DIPA formation.
These issues reinforce the importance of trace-impurity control, residue definitions, groundwater-metabolite assessment and exposure minimisation.
Combustion or severe overheating can produce corrosive and toxic chlorine-, nitrogen- and sulfur-containing fumes.

FIRST AID

Inhalation: Move the affected person to fresh air, keep the person at rest and obtain medical attention if exposure was significant or symptoms develop.

Skin Contact: Remove contaminated clothing, wash the skin thoroughly with soap and running water and obtain medical attention for irritation or an allergic reaction.

Eye Contact: Rinse cautiously with clean water for at least 15 minutes, remove contact lenses when easy to do and obtain medical attention if irritation continues.

Ingestion: Rinse the mouth, do not induce vomiting and obtain immediate medical attention, particularly because liquid formulations may contain hydrocarbon solvents.

Note to Physicians: No specific antidote is established, treatment is supportive and Tri-allate exposure does not by itself indicate cholinesterase-reactivating therapy.

HANDLING, STORAGE AND SPILL RESPONSE

Store Tri-allate in tightly sealed, clearly identified containers in a cool, dry, secure and well-ventilated pesticide area.
Keep Tri-allate away from food, feed, seed, strong oxidising agents, excessive heat and ignition sources associated with formulation solvents.
Secondary containment is required for liquids, while dry granular stores need moisture exclusion and dust control.

Controlled warming may be used to liquefy technical Tri-allate for transfer because the active melts near 30 °C.
Heat must be distributed evenly and kept well below the decomposition range, with temperature monitoring at the container and transfer line.
Emulsifiable concentrates also require bonding, grounding and ignition control when their solvent package is combustible or flammable.

For a spill, isolate the area, stop the release when safe and block entry to drains, ditches and surface water.
Collect intact granules by a low-dust method, absorb liquid with inert non-combustible material and place recovered waste in a labelled pesticide-waste container.
Contaminated soil, absorbent, wash liquid and damaged packaging remain controlled waste because of the aquatic hazard.

PACKAGING AND SUPPLY CONSIDERATIONS

Technical Tri-allate is packed in compatible sealed containers that tolerate both the solid and molten states encountered during transport, storage and unloading.
Emulsifiable concentrates require solvent-resistant closures, gaskets and container walls, while granules require moisture-resistant packaging with adequate mechanical strength and dust containment.
Package selection also reflects hazardous-goods classification, batch consumption, metering equipment and the need to minimise residues after emptying.

A complete Tri-allate enquiry identifies technical active, emulsifiable concentrate, granule or analytical standard; the required concentration; impurity limits; destination country; registered crop and weed use; package size; batch quantity; delivery schedule; and documentation set.
Ataman Kimya supports professional Tri-allate enquiries with attention to active-content specification, nitrosamine control, formulation performance, analytical documentation, packaging and destination-market supply requirements.
For product and procurement discussions, contact Ataman Kimya at +90 216 577 10 10 or info@atamankimya.com.