CS226916B1 - N-arensulphonyl-n-l,2,4-triazine-5)4h(/on-4-yl) ureas and method of preparing same - Google Patents

Description

(54) N-Arenesulfonyl-N - [1,2,4-triazin-5 (4H) -quin-4-yl] urea and process for their preparation

The invention relates to N ‘- [1,2,4-triazin-5 (4H) -quinaz-4-yl] ureas and a process for their preparation. The compounds can be used as herbicides and plant growth regulators.

Compounds of formula I have now been identified

N-NH-CO-NH-SOF ^ Q ^ <T _{', and} in which the

R ¹ represents hydrogen, halogen such as chloro or fluoro, methyl, nitro, trifluoromethyl,

R ² is methylthio, methoxy, methyl, anilino, morpholino,

R ³ is C 1 -C 4 alkyl, phenyl or cyclohexyl; and n is an integer of 0 to 3, and a process for their preparation by reaction of 4-amino-1,2,4-triazin-5 (4H) -ones of formula II wherein:

R ² and R ⁵ are as defined with formula III arylsulfonylizokyanátmi

SOfNCO (III) wherein

R ¹ and n are as defined above in inert organic aprotic solvents such as benzene, toluene, xylene, chlorobenzene, dichloromethane, chloroform, acetonitrile, tetrahydrofuran, diethyl ether at a temperature of 20 to 140 ° C, optionally in the presence of a catalyst.

The reaction is generally exothermic. The reaction products are usually insoluble in the reaction medium and precipitate in crystalline form when hot. In this case, isolation is effected by aspirating the crystalline substance from the reaction mixture. If the product is soluble in the reaction medium, it is isolated after concentration of the solvent and addition of a suitable solvent from which the product crystallizes.

Compounds of formula (II) for the preparation of the compounds of the invention may be prepared by methods known in the literature, such as A. Dornow et al., Chem. Ber. 97, 2173, 2640 (1964), ibid 100, 2585 (1967), DOS 2,107,757, DOS 2,138,031, MS. No. 179,931.

The starting compounds of formula III can also be prepared by methods known in the literature by reaction of sulfonamides with phosgene, such as described by H. Ulrich et al., J. Org. Chem. 31, 2658 (1966).

G. King: J. Org. Chem. 25, 352 (1960), F. Effenberger et al., Chem. Ber. 97, 1576 (1964), U.S. Pat. No. 3,371,114, DOS 2,152,971.

The compounds of the invention are prepared without catalysts, but catalysts such as triethylamine, pyridine and the like can be used in the reaction.

These examples illustrate but do not limit the scope of the invention.

Example 1

N- (p-toluenesulfonyl) -N- [3-methylthio-6- (1,1-dimethylethyl) -1,2,4-triazin-5 (4H) -one-4-yl] urea.

While stirring at normal temperature, a solution of 4 was added to a solution of 4.3 g of 2-methylthio-4-amino-6-1,1-dimethylethyl-1,2,4-triazin-5 (4H) -one in 30 ml of anhydrous benzene. 1.0 g of p-toluenesulfonyl isocyanate in 15 ml of anhydrous benzene. The mixture was stirred for 15 minutes, then heated to reflux. It was kept at this temperature for 15 minutes. After cooling, the solid was aspirated and washed with benzene.

Yield:

8.0 g (96.3 O / o)

Melting point:

Mp 180-183 ° C.

Analysis for C16H21N5O4S2 (411.5)

Detected:

N 17.04 S 15.05%

Calculated:

N 17.02 S 15.58%.

Example 2

N- (o-toluenesulfonyl) -N- [3-methylthio-6- (1,1-dimethylethyl) -1,2,4-triazin-5 (4H) -one-4-yl] urea.

A solution of 4.3 g of 2-methylthio-4-amino-6- (1,1-dimethylethyl) -1,2,4-triazin-5 (4H) -one in 30 ml of anhydrous benzene was added with stirring at normal temperature. 4.0 g of o-toluenesulfonyl isocyanate in 15 ml of anhydrous benzene After stirring for 15 minutes, the mixture was heated to reflux temperature and maintained at this temperature for 15 minutes, after which the product crystallized, filtered off with suction and washed with benzene.

Yield:

7.9 g (95.1%)

Melting point:

Mp 165-167 ° C.

Analysis for C16H21N5O4S2 (411.5)

Detected:

N 17.02 S 15.75%

Calculated:

N 17.02 S 15.58%

Other compounds listed in Table 1 were prepared analogously.

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Claims (3)

OBJECT OF THE INVENTION 1. An N-arenesulfonyl-N '- [l, 2,4-triazin-5 (4Hj- -one-4-yl] urea of Formula I-N-NH-C0-NH-S0 ₂ - / q \ (I ) in which R ¹ represents hydrogen, chloro or fluoro, methyl, nitro or trifluoromethyl, R ² is methylthio, methoxy, methyl, anilino or morpholino, R ³ is C 1 -C 4 alkyl, phenyl or cyclohexyl; and n is an integer of 0 to 3. 2. A process for the preparation of compounds according to claim 1, characterized in that the 4-amino-1,2,4-triazin-5 (4H) -ones of the general formula III R ² and R ³ are as defined above are reacted with a formula III arylsulfoizokyanátom SOg-NCQ (III) in which R ¹ and n are as previously defined in an inert organic aprotic solvent such as benzene, toluene, xylene, chlorobenzene, acetonitrile, chloroform at a temperature of 20 to 140 ° C. 3. The process of claim 2 wherein the reaction is carried out in the presence of a catalyst.