34014-18-1

Basic information

• Product Name: 1-(5-tert-Butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea
• Synonyms: Perflan;Perfmid;Preflan;Prefmid;sha105501;spike80w;Tebithiuron;Tebulan
• CAS NO: 34014-18-1
• Molecular Formula: C₉H₁₆N₄OS
• Molecular Weight: 228.31
• EINECS: 251-793-7
• Product Categories: Alphabetic;Herbicides;TA - TEPesticides&Metabolites;Urea structure;Alpha sort;Pesticides&Metabolites;Q-ZAlphabetic;Pesticides intermediate
• Mol File: 34014-18-1.mol

Chemical Properties

• Melting Point: 161-164°C
• Appearance: /Solid
• Density: 1.2080 (rough estimate)
• Refractive Index: 1.6390 (estimate)
• Storage Temp.: 0-6°C
• PKA: 13.36±0.46(Predicted)
• Water Solubility: 2.3g/L(temperature not stated)
• Merck: 14,9095
• BRN: 527479
• CAS DataBase Reference: 1-(5-tert-Butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(5-tert-Butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea(34014-18-1)
• EPA Substance Registry System: 1-(5-tert-Butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea(34014-18-1)

Safety Data

• Hazard Codes: Xn;N,N,Xn
• Statements: 22-50/53
• Safety Statements: 37-60-61
• RIDADR: UN 3077
• WGK Germany: 3
• RTECS: YS4250000
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 34014-18-1(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Applications:
1-(5-tert-Butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea is used as a herbicide for controlling weeds in non-cropland areas, rangelands, rights-of-way, and industrial sites. It is effective against a wide range of plant species, including alfalfa, bluegrasses, chickweed, clover, dock, goldenrod, and mullein.
Used in Non-cropland Management:
1-(5-tert-Butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea is used as a nonselective herbicide to control herbaceous and woody plants in non-cropland areas. It helps in maintaining the land free from unwanted vegetation, which can be beneficial for various purposes such as construction, infrastructure development, and land management.
Used in Grassland Management:
In grasslands, 1-(5-tert-Butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea is used as a herbicide to control woody and herbaceous plants, ensuring the proper growth and maintenance of grasslands.
Used in Sugar Cane Cultivation:
1-(5-tert-Butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea is used as a herbicide in sugar cane cultivation to control weeds and other competing plants, which can negatively impact sugar cane growth and yield.

Reactivity Profile

A urea, thiadiazole derivative.

Trade name

BRULAN?; BRUSH-BULLET?; E-103?; GRASLAN?; HERBEC?; HERBIC?; PERFLAN?; RECLAIM; SHA-105501?; SPIKE?; SPRAKIL?; TEBULAN?; TIUROLAN?

Environmental Fate

Soil. In microbially active soils, tebuthiuron is degraded via demethylation. The average half-life in soil 12–15 months in areas receiving 60 inches of rainfall a year (Humburg et al., 1989).When tebuthiuron was applied to a rangeland at a rate of 0.84 kg/ha, 38% remained after 21 months (Emmerich et al., 1984).Groundwater . According to the U.S. EPA (1986) tebuthiuron has a high potential to leach to groundwater .Plant. Degrades in plants via N-demethylation and hydroxylation of the t-butyl sidechain (Hartley and Kidd, 1987; Humburg et al., 1989).

InChI:InChI=1/C9H16N4OS/c1-9(2,3)6-11-12-8(15-6)13(5)7(14)10-4/h1-5H3,(H,10,14)

Upstream product

• 96-31-1 N,N'-Dimethylurea 
• 95517-81-0 5-tert-butyl-2-methanesulfonyl-1,3,4-thiadiazole 
• 74-89-5 methylamine 
• 75-98-9 Trimethylacetic acid 
• 42826-42-6 pivalohydrazide 
• 50608-12-3 2-tert-butyl-5-methylamino-1,3,4-thiadiazole 
• 106141-32-6 N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-N-methylcarbamoyl chloride 

Downstream Products

• 74-89-5 methylamine 

Relevant articles and documents

Industrial production method of tebuthiuron active compound

The invention discloses an industrial production method of a tebuthiuron active compound. The method comprises the following steps: (1) dissolving a raw material 2-methylamino-5-tertbutyl-1, 3, 4-thiadiazole in an inert solvent to prepare an inert solvent solution with a certain concentration; (2) carrying out a photochemical reaction on the 2-methylamino-5-tertbutyl-1, 3, 4-thiadiazole toluene solution and phosgene or a diphosgene or triphosgene solution; (3) removing phosgene from the material after the photochemical reaction is finished; (4) carrying out amidation reaction on the phosgene-removed material and monomethylamine gas; and (5) after the amidation reaction is finished, carrying out post-treatment on the material to obtain the tebuthiuron product. The product quality is more stable. The device investment is reduced, the device production capacity is improved, the technological process is simpler, and continuous self-control operation of the device is facilitated.

Synthetic method of 1,3,4-thiadiazole derivative

The invention discloses a synthetic method of a 1,3,4-thiadiazole derivative. The method comprises the following steps: (1) using hydrazine hydrate as a raw material, under the action of a catalyst, reacting with acid, to obtain a hydrazide compound I; (2) using alkyl chloroformate and thiocyanate to react in a condition of a solvent, to obtain an isothiocyanate compound II; (3) in a reaction system of the isothiocyanate compound II, adding solution containing the compound I, reacting to obtain solution containing a compound III; (4) processing the solution of the compound III by dehydrating,neutralizing, and washing, to obtain a compound IV; (5) in the conditions of an acid-binding agent and a solvent, adding alkyl halide or sulfuric acid diester into the compound IV, reacting to obtaina compound V; and (6) enabling the compound V to perform an amination reaction with primary amine, to obtain the 1,3,4-thiadiazole derivative VI. The preparation method has the advantages of green andno pollution, simple and convenient operation, higher yield, mild reaction condition and the like.

NOXIOUS ARTHROPOD CONTROL AGENT CONTAINING AMIDE COMPOUND

An object of the present invention is to provide a compound having the controlling activity on a noxious arthropod, and a noxious arthropod controlling agent containing an amide compound of formula (I): wherein X represents a nitrogen atom or a CH group, p represents 0 or 1, A represents a tetrahydrofuranyl group or the like, R1, R2, R3, R4, R5, R6 and R7 represent a hydrogen atom or the like, n represents 1 or 2, Y represents an oxygen atom or the like, m represents any integer of 0 to 7, and Q represents a C1-8 chain hydrocarbon group optionally having a phenyl group or the like, has the excellent noxious arthropod controlling effect.

A method for synthesizing special Ding Saicao is prosperous (by machine translation)

The present invention provides a method for synthesizing special Ding Saicao is prosperous, in order to 1,3-dimethoxy ylurea and 5-tert-butyl -1, 3, 4-thiadiazole derivatives in alkaline condition reaction special Ding Saicao is prosperous. The method solves the problem that the conventional method with the use of toxic substances in methyl isocyanate, N-methyl formyl chloride or phosgene and security risk, the difficulties and problems such as the production operation. (by machine translation)

Process for preparing herbicidal ureas and insecticidal carbamates and carbamate derivatives

The present invention provides a process for preparing herbicidal ureas and insecticidal carbamates and carbamate derivatives comprising reacting an amine, alcohol, or oxime nucleophile with a urea in an inert organic solvent.

Process for preparing ureas

The present invention provides a novel process for preparing herbicidal and insecticidal ureas, carbamates and carbamate derivatives of the formula E is -O- or -C(R4)2- ;, R is C1-C7 alkyl;, R1 is H, C1-C7 alkyl, C3-C7 cycloalkyl, phenyl, or C1-C4 alkylphenyl;, R2 is H, C1-C7 alkyl, C3-C7 cycloalkyl, C2-C7 alkenyl, C2-C7 alkynyl, or phenyl optionally substituted with Cl, Br, -NO2, -CF3, C1-C4 alkyl, C1-C4 alkoxy, or -N(C1-C4 alkyl)2;, R3 is H, F, Cl, Br, -CF3, C1-C7 alkyl option-ally substituted with F, Cl, or Br, -S(O)nC1-C7 alkyl, C1-C7 alkoxy, C3-C7 cycloalkyl optionally substituted with F, Cl, or Br, or phenyl optionally substituted with F, Cl, Br, -NO2, -CF3, or C1-C4 alkyl;, R4 is H or C1-C4 alkyl;, R5 is C1-C7 alkoxy or -S(O)nC1-C7 alkyl;, R6 is C1-C5 alkyl optionally substituted with F, Cl, or Br, C3-C5 cycloalkyl, phenyl, or, , - X is R3, -N=CH-N(C1-C4 alkyl)2, -N(C1-C4 alkyl)2 or -N(C2-C4 alkenyl)2, Y is H or S(O)nC1-C7 alkyl;, Z is H, C1-C4 alkyl, Cl, F, Br, haloalkyl, -NO2, -N(C1-C4 alkyl)2, -C≡N, phenyl, -S(C1-C4 alkyl), or C1-C4 alkoxy;, n is 0, 1, or 2; and, m is 1, 2 or 3,comprising reacting a nucleophile of the formula A-H, wherein A is as defined above, with a urea of the formula wherein each R is independently chosen from R as set forth above and each R1 is independently chosen from R1 as set forth above.

Process for preparing the compound 5-t-butyl-2-methylamino-1,3,4-triadiazole

A process for preparing the compound 5-t-butyl-2-methylamino-1,3,4-thiadiazole, STR1 in high yield by the reaction of 4-methyl-3-thiosemicarbazide with pivalic acid in a solution containing both polyphosphoric acid and concentrated sulfuric acid, followed by neutralizing the reaction mixture with a neutralizing mixture comprising an organic solvent and an alkaline substance dissolved in water and separating 5-t-butyl-2-methylamino-1,3,4-thiadiazole from the organic phase.

Herbicidal method

There is disclosed a method of controlling unwanted vegetation in fallow wheatland by the application of a substituted thiadiazol-2-ylurea following the harvesting of the wheat crop.