41814-78-2

Basic information

• Product Name: Tricyclazole
• Synonyms: Blascide;El 291;el-291;Elanco 291;elanco291;s-Triazolo(3,4-b)benzothiazole, 5-methyl-;Tricyclazone;Tricyclozole
• CAS NO: 41814-78-2
• Molecular Formula: C₉H₇N₃S
• Molecular Weight: 189.24
• EINECS: 255-559-5
• Product Categories: HERBICIDE;Alpha sort;Fungicides;OthersPesticides&Metabolites;Pesticides;Q-ZAlphabetic;TP - TZ;pesticide;Agricultural Usage
• Mol File: 41814-78-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 187-188°C
• Boiling Point: 275 °C
• Appearance: powder
• Density: 1.2292 (rough estimate)
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 0-6°C
• PKA: 2.40±0.40(Predicted)
• Water Solubility: 1.6g/L(25 oC)
• BRN: 980261
• CAS DataBase Reference: Tricyclazole(CAS DataBase Reference)
• NIST Chemistry Reference: Tricyclazole(41814-78-2)
• EPA Substance Registry System: Tricyclazole(41814-78-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RIDADR: 2588
• WGK Germany: 1
• RTECS: XZ5475000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 41814-78-2(Hazardous Substances Data)

Usage

Description

log Kow: 1.4. Solubility: In water at 25 ?C, 1.6 g/L. In acetone 10.4, methanol 25, xylene 2.1 (all in g/l, 25 ?C). Stability: Stable at 52 ?C. Relatively stable to ultraviolet light.

Uses

Tricyclazole is an common active ingredient in several commercial fungicide products used to control rice blast fungus, in transplanted and direct-seeded rice.

Definition

ChEBI: A triazolobenzothiazole that is [1,2,4]triazolo[3,4-b][1,3]benzothiazole which is substituted at position 5 by a methyl group. A fungicide used for the control of rice blast, it is not approved for use within the European Union.

Metabolism

Animals: Rapid and extensive metabolism. Plants: The principal metabolite is the hydroxymethyl analog. Soil/Environment: Kd 4 (loamy sand, pH 6.5, 1.5% o.m.), 45 (loam, pH 5.7, 3.1% o.m.), 21 (clay loam, pH 7.4, 1.9% o.m.), 22 (silty clay loam, pH 5.7, 4.1% o.m.).

Toxicity evaluation

Mammalian toxicology. Oral: Acute oral LD50 for rats 314, mice 245, dogs >50 mg/kg. Skin and eye: Acute percutaneous LD50 for rabbits >2000 mg/kg. Slight eye irritant; nonirritating to skin (rabbits). Inhalation: LC50 (1 h) for rats 0.146 mg/L air. NOEL: (2 yr) for rats 9.6 mg/kg b.w.; for mice 6.7 mg/kg b.w.; (1 yr) for dogs 5 mg/kg b.w.; 3-generation reproduction for rat 3 mg/kg b.w. ADI: 0.03 mg/kg. Toxicity class: World Health Organization (WHO) (a.i.) II; U.S. Environmental Protection Agency (EPA) (formulation) II RC risk Xn (R22). Ecotoxicology. Birds: Acute oral LD50 for mallard ducks and bobwhite quail >100 mg/kg. Fish: LC50 for bluegill sunfish 16.0, rainbow trout 7.3, goldfish fingerlings 13.5 mg/l. Daphnia: LC50 (48 h) > 20 mg/l; NOEC (21 d) 0.96 mg/L.

InChI:InChI=1/C9H7N3S/c1-6-3-2-4-7-8(6)12-5-10-11-9(12)13-7/h2-5H,1H3

Synthetic route

3-allenylthio-5-methyl-s-triazolo<3,4-b>benzothiazole → 5-methyl-1,2,4-triazolo[3,4-b]benzothizole (41814-78-2)

Conditions	Yield
With hydrogen; nickel In ethanol for 6h; Heating;	78.7%

5-methyl-3-mercapto<1,2,4>triazolo<3,4-b>benzothiazole (147423-88-9) → 5-methyl-1,2,4-triazolo[3,4-b]benzothizole (41814-78-2)

Conditions	Yield
With nickel In ethanol for 8h; Heating; further reagent: dilute nitric acid;	66.6%
Multi-step reaction with 2 steps 1: aq. NaOH / 2 h 2: 78.7 percent / H2 / Raney-Ni / ethanol / 6 h / Heating View Scheme

formic acid (64-18-6) + 4-methyl-2-hydrazinobenzothiazole (20174-68-9) → 5-methyl-1,2,4-triazolo[3,4-b]benzothizole (41814-78-2)

Conditions	Yield
for 1h; Heating;	61.3%
Stage #1: 4-methyl-2-hydrazinobenzothiazole With sodium carbonate In water; ethylene glycol; xylene at 110 - 115℃; for 4 - 5h; Azeotropic distilation; Stage #2: formic acid With toluene-4-sulfonic acid In ethylene glycol; xylene at 110 - 120℃; for 4 - 5h; Azeotropic distilation;

4-methyl-1,3-benzothiazol-2-amine (1477-42-5) → 5-methyl-1,2,4-triazolo[3,4-b]benzothizole (41814-78-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / hydrazine hydrate, conc. HCl / ethane-1,2-diol / 2 h / 150 - 160 °C 2: 63.3 percent / KOH / ethanol; H2O / 1 h / Heating 3: 66.6 percent / Raney Ni / ethanol / 8 h / Heating; further reagent: dilute nitric acid View Scheme
Multi-step reaction with 2 steps 1: 81 percent / hydrazine hydrate, conc. HCl / ethane-1,2-diol / 2 h / 150 - 160 °C 2: 61.3 percent / 1 h / Heating View Scheme

4-methyl-2-hydrazinobenzothiazole (20174-68-9) → 5-methyl-1,2,4-triazolo[3,4-b]benzothizole (41814-78-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 63.3 percent / KOH / ethanol; H2O / 1 h / Heating 2: 66.6 percent / Raney Ni / ethanol / 8 h / Heating; further reagent: dilute nitric acid View Scheme

formaldehyd (50-00-0) + N-methylaniline (100-61-8) + 5-methyl-1,2,4-triazolo[3,4-b]benzothizole (41814-78-2) → 5-methyl-3-(N-methylanilinomethyl)<1,2,4>triazolo<3,4-b>benzothiazole

Conditions	Yield
In ethanol at 60℃; for 3h;	26%

5-methyl-1,2,4-triazolo[3,4-b]benzothizole (41814-78-2) → 5-methyl<1,2,4>triazolo<5,1-b>benzothiazole (61073-33-4)

Conditions	Yield
With sodium hydroxide for 0.5h; Heating;

Upstream product

• 64-18-6 formic acid 
• 20174-68-9 4-methyl-2-hydrazinobenzothiazole 
• 147423-88-9 5-methyl-3-mercapto<1,2,4>triazolo<3,4-b>benzothiazole 
• 1477-42-5 4-methyl-1,3-benzothiazol-2-amine 

Relevant articles and documents

Synergistic Combinations Of Active Ingredients

The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and A have the meanings given in the description and, secondly, at least one further known active compound from groups (2) to (27) listed in the description, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids and also phytopathogenic fungi.

INDUSTRIAL PROCESS FOR PREPARING ENVIRONMENTALLY SAFE TRICYCLAZOLE

An improved efficient environmentally safe process for the production of Tricyclazole useful fungicide for rice blast in aqueous slurry form, which involves reacting Hydrazino intermediate (2) obtained from amino compound (1) with formic acid in the presence of p- Toluene sulphonic acid catalyst in two step reaction is discussed. In reaction step (a) 2- Hydrazine -4- methyl benzothiazole (2) is prepared by reacting Amino compound (1) with 80 % Hydrazine Hydrate in the presence of MEG and Hydrochloric acid at 100- 120 ° C. In step (b) the condensation process with 85-98 % formic acid is carried in the presence of acid promotor catalyst at 100- 140° C. The final product is isolated in aqueous slurry form by dumping solvent free molton stirrable mass in precooled water.

Iminoacetic acid amides and their use as pest control agents

PCT No. PCT/EP96/04345 Sec. 371 Date Apr. 15, 1998 Sec. 102(e) Date Apr. 15, 1998 PCT Filed Oct. 7, 1996 PCT Pub. No. WO97/14673 PCT Pub. Date Apr. 24, 1997Iminoacetamides of the formula (I) in which A represents a single bond or optionally substituted alkylene, Q represents oxygen or sulphur, R1 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl, R2 represents respectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, R3 represents hydrogen or respectively optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl, R4 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclcyl a process for their preparation, pesticidal compositions containing them, and their use for controlling pests.