CS266987B1 - N- (2,6-dialkylphenyl) -N-furthiryl-N '- (arenesulfonyl) urea and their method of preparation - Google Patents

Abstract

The solution relates to N-(2,6-dialkylphenyl)-N-furfuryl-N'-(arenesulfonyl) ureas of general formula I, as well as to a method for their preparation from 2,6-dialkyl-N-furfurylaniline of general formula II, which are treated with arenesulfonyl isocyanates of general formula III in an inert organic solvent such as benzene, toluene, xylene, acetonitrile chloroform, dichloromethane, tetrahydrofuran, at temperatures up to 120 °C. The solution can be used in the chemical industry.

Description

The invention relates to N- (2,6-dialkylphenyl) -N-furfuryl [-N '- (arenesulfonyl) ureas and to a process for their preparation. Said compounds can be used as herbicides.

Sulfonylureas derived from usulfonamides and heterocyclic amines are abundantly described in the technical and patent literature (Petersen, U., HOUBEN-WEYL, V .: Methoden der organischen Chemie, 4th edition E 4, Georg Thieme Verlag, Stuttgard 1983, pp. 400-400. 402). Many compounds of this group have herbicidal or pharmacological properties.

N- (2,6-dialkylphenyl) -N-furfuryl-N '- (arenesulfonyl) ureas of the formula I have now been found.

Wherein R is hydrogen, methyl, chloro or methoxycarbonyl, R and R are methyl or ethyl. A process for the preparation of said compounds of formula I by reacting 2,6-dialkyl-N-furfurylaniline of formula II, R ^{2 has also been found.}

NH-CH ₂ - (TJ / IV, 'r ³

3 in which R and R are as defined above, with arenesulphonyl isocyanates of the general formula III -so ₂ nco / 111 /

R ¹ in which R ⁴ is as defined above, in the presence of an inert organic solvent such as benzene, toluene, xylene, dichloromethane, acetonitrile, tetrahydrofuran at a temperature of up to 120 ° C. It has also been found advantageous to carry out the reaction at reflux of the solvent or in a pressure vessel.

The reaction can be catalyzed by tertiary bases such as triethylamine, pyridine and the like.

After cooling the mixture, the reaction products are insoluble in the reaction medium, they can be separated from the solvent or reactants, e.g. suction.

Intermediates of formula II for the preparation of the compounds of the invention may be prepared by methods known in the art such as hydrogenation of the corresponding azomethine, hydrogenation alkylation of 2,6-dialkylanilines with furfural or alkylation of 2,6-dialkylanilines with furfuryl chloride.

The starting compounds of the formula III can also be prepared by methods known from the literature, for example by reacting sulfonamides with phosgene (U.S. Pat. No. 3,317,114, DE 2,152,971, H. Ulrich et al .: Angew. Chem. 78, 761 (1966)) or by reacting arenesulfonamides. with chlorosulfonyl isocyanate (DE 1 289 526).

The N- (2,6-dialkylphenyl) -N-furfuryl-N '- (arenesulfonyl) urea according to the invention can be used for weed control. For this purpose, they can be formulated as solutions, emulsions, suspensions, powders and the like. These are prepared in a known manner, for example by mixing the active compound with auxiliaries such as liquid solvents or solid carriers, optionally using surfactants such as emulsifiers or dispersants.

The following examples illustrate but do not limit the scope of the invention.

CS 266 987 Bl

Example 1

To a stirred mixture of 6.5 g (0.03 mol) of 2-methyl-6-ethyl-N-furfurylaniline and 20 ml of anhydrous benzene was gradually added 5.5 g (0.03 mol) of benzenesulfonyl isocyanate in 10 ml of benzene. slightly exothermic reaction. The mixture was stirred for another 2 h to react. The solid was filtered off with suction and washed with benzene. 10.45 g (87%) of N- [2-methyl-6-ethylphenyl-N-furfuryl-N'-benzenesulfonylurea] are obtained. t. 176.3 ° C.

Analysis for ^N 2 ^{O 4 S} < ^m · ³⁹⁸ '48) calculated:% C 63.29; % H 5.56; % N 7.03; % S 8.04 found:% C 63.1; % H 5.6; % N 6.7; % S 7.9

The compounds listed in Table 1 were prepared in the same manner at different temperatures.

Table 1

Compound T. t. ° C Yield% Molar mass Analysis found / calculated % C % H % N % WITH N- (2-methyl-6-ethylphenyl) -N-furfuryl-N'-o-methoxycarbonylbenzenesulfonylurea 83.7 47 456.53 59.9 60.46 5.2 5.30 6.1 6.14 7.2 6.99 N- (2-methyl-6-ethyl-phenyl) -N- -fur furyl-N'-p-toluene sulfonylurea 162.2 70 412.49 63.9 64.06 5.9 5.86 6.4 6.79 7.5 7 _ø 77 N- (2-methyl-6-ethylphenyl) -N-furfuryl-N'-o-chlorobenzene sulfonylurea 162.3 80 412.49 64.4 64.06 5.9 5.86 6.4 6.79 7.5 7.77 N- (2-methyl-6-ethylphenyl) -N-furfuryl-N'-chlorobenzene sulfonesIurea 182.1 85 432.93 58.4 58.26 4.9 4.89 6.1 6.47 7.2 7.41 N- (2,6-dimethylphenyl) -N-fururyl 1-N'-benzenesulfonates Urea 204.8 86 384.46 63.1 62.47 5.2 5.24 7.3 7.28 8.6 8.34 N- (2,6-diethylphenyl) -N-furfuryl- -N'-benzenesulfonylurea 148.5 80 412.44 64.4 64.06 5.8 5.86 6.8 6.79 7.5 7.77 N- (2,6-dimethylphenyl) -N-furfuryl-N'-p-toluenesulfonylurea 172.1 87 398.48 64.3 63.29 5.6 5.56 7.2 7.03 8.4 8.05 N- (2,6-diethylphenyl) -N-furfuryl- -N "-p-toluenesulfonylurea 159.5 67.5 426.46 65.0 64.77 6.2 6.14 6.6 6.57 7.3 7.52 N- (2,6-dimethylphenyl) -N-furfuryl- -N'-o-toluenesulfonylurea 194.1 87 398.48 63.5 63.29 5.6 5.56 7.0 7.03 8.3 8.05 N- (2,6-dimethylphenyl) -N-furfuryl- -H'-o-toluenesulfonylurea 194.5 78 426.46 63.4 64.77 5.6 6.14 7.0 6.57 8.3 7.52 N- (2,6-dimethylphenyl) -N-furfuryl- -Ν'-o-chlorobenzenesulfonylurea 213.2 95 418.90 57.7 57.34 4.6 4.57 6.7 6.69 7.8 7.65 N- (2,6-diethylphenyl) -N-furfuryl- -N'-o-chlorobenzenesulfonylurea 170.3 65 446.88 59.2 59.12 5.2 5.19 6.3 6.27 7.0 7.17 N- (2,6-dimethylphenyl) -N-furfuryl- -N'-o-methoxycarbonylbenzenesulfonylurea 170.7 70 442.50 59.2 59.71 4.9 5.0 6.2 6.33 7.5 7.25 N- (2,6-diethylphenyl) -N-furfuryl-N'-o-methoxycarbonylbenzene sulfonylurea 112.8 51 470.55 61.1 56.51 5.5 5.57 5.9 5.95 7.2 6.81

Example 2

In polyvinyl chloride containers (16.5x21x3 cm) filled with standard aluminum sand

CS 266 987 Bl soil was sown as test objects in the following rows:

A - deaf oats (Avena fatua), F - buckwheat (Fagopyrum vulgare), S - mustard (Sinapis alba), P - millet (Panicům milliaceum), L - mustard (Lepidium sativum).

After leveling the soil surface, a light watering was performed and the soil surface was immediately sprayed with formulations containing as active ingredients the compounds of the formula I in a concentration of 0.5%. The preparations were used in a volume of 2 ml per container, corresponding to a dose of 2.5 kg.ha ^-3 . The herbicide metolachlor was used as a standard. The degree of damage to the test plants was determined at day 21 after treatment and was expressed by a rating scale of 0 to 5, in which grade 0 means plants normally developed, grade 5 means plants dead. The results are summarized in Table 2.

Table 2

/ 1 /

Substituent

Test object

R ¹ R ² R ³ A F with P L 2-carbomethoxy methyl ethyl 3.5 2 1 3 3 4-methyl methyl ethyl 3 2 0 4 2 2-methyl methyl ethyl 3 1 1 3.5 2 2-chlorine methyl ethyl 3.5 2 1 4 3.5 H methyl ethyl 3 1 0 2 2 H ethyl ethyl 3 1 0 2 2 4-methyl methyl methyl 2 2 0 4 2 4-methyl ethyl ethyl 2 2 0 4 1 2-methyl methyl methyl 3 3 1 3.5 2 2-methyl ethyl ethyl 3 2 1 3 2 2-chlorine methyl methyl 4 2 2 4 4 2-chlorine ethyl ethyl 4 2.5 2 4 4.5 2-carbomethoxy methyl methyl 3 2 1 3 3 2-carbomethoxy ethyl ethyl 3 1 2 2 3 Standard metolachlor 3 3 4 2.5 3.5

OBJECT OF THE INVENTION

Claims (2)

CS 266 987 B1, as test subjects, were seeded in rows: A - Deaf Oats (Avena fatua), F - Buckwheat (Fagopyrum vulgare), S - Mustard (Sinapis alba), P - Millet (Panicum milliaceum), L - Duck Lepidium sativum). After leveling the soil, a light water dressing was made and the surface of the soil was immediately sprayed with formulations containing as active ingredients a compound of formula I at a concentration of 0.5%. The formulations were used in a volume of 2 ml per vial, corresponding to a dose of 2.5 kg.ha-3. The standard used was the metolachlor herbicide. The degree of damage to the test plants was found 21 days after treatment and was expressed by a 0 to 5 bonitation scale, in which grade 0 means the plants normally developed, grade 5 means dead plants. The results are summarized in Table 2. Table 2 Substituent Test object R1 R2 R3 AF with PL 2-carbomethoxy methyl ethyl 3,5 2 1 3 3 4-methyl methyl ethyl 3 2 0 4 2 2-methyl methyl ethyl 3 1 1 3,5 2 2-chloromethyl ethyl ethyl 3, 5 2 1 4 3,5 H methyl ethyl 3 1 0 2 2 H ethyl ethyl 3 1 0 2 2 4-methyl methyl methyl 2 2 0 4 2 4-methyl ethyl ethyl 2 2 0 4 1 2-methyl methyl methyl 3 3 1 3,5 2 2-methyl ethyl ethyl 3 2 1 3 2 2-chloro methyl methyl 4 2 2 4 4 2-chloroethyl ethyl 4 2,5 2 4 4,5 2-carbomethoxy methyl methyl 3 2 1 3 3 2 -carbomethoxy ethyl ethyl 3 1 2 2 3 standard metolachlor 3 3 4 2.5 3.5 SUBJECT OF THE INVENTION 1. N- (2,6-dialkylphenyl) -N-furfuryl-N '- (arenesulfonyl) urea of formula (I) Z is CH, -O / 1, conhso2 1 - 2 3 in R is hydrogen, methyl, chloro or methoxycarbonyl, R and R are methyl or ethyl CS 266 987 B1 2. A process for the preparation of the compounds according to claim 1, characterized in that the 2,6-dialkyl-N-furfurylaniline of formula II is o2. In which R and R are as defined above, arenesulfonyl isocyanate of general formula III is used in which R @ 1 is as defined above, in an inert organic solvent medium. such as benzene, toluene, xylene, acetonitrile, chloroform, dichloromethane, tetrahydrofuran at a temperature of up to 120 ° C.