CS266985B1 - Substituted n-(2,6-dialkyl phenyl)n-arene sulphonyl urea and method of their preparation - Google Patents

Substituted n-(2,6-dialkyl phenyl)n-arene sulphonyl urea and method of their preparation Download PDF

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CS266985B1
CS266985B1 CS88725A CS72588A CS266985B1 CS 266985 B1 CS266985 B1 CS 266985B1 CS 88725 A CS88725 A CS 88725A CS 72588 A CS72588 A CS 72588A CS 266985 B1 CS266985 B1 CS 266985B1
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ethyl
methoxycarbonyl
methyl
substituted
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Vaclav Rndr Csc Konecny
Emanuel Ing Csc Beska
Peter Rndr Magdolen
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Konecny Vaclav
Beska Emanuel
Magdolen Peter
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Abstract

Riešenie sa týká substituovaných N- -/2,6-dialkylfenyl/-N'-arénsulfonylmočovín všeobecného vzorca I, ktoré majú herbicídny účinok. Uvedené zlúčeniny sa dajú připravit reakciou substituovaných N-2,6-dialkylanilí- nov všeobecného vzorca II s arénsulfonylizokyanátom všeobecného vzorca III v prostředí inertného organického rozpúštadla zo skupiny zahrftujúcej benzén, toluén, xylén, acetonitril, chloroform, dichlórmetén, tetrahydrofurán pri teplote do 120 °C. Ve vzoroch Rl je H, Cl, CH3 alebo metoxykarbonyl a R2 a R3 znamenajú CHj alebo ethyl a R4 je metoxy-Cj-salkyl.The solution relates to substituted N- - / 2,6-dialkylphenyl / N 'arénsulfonylmočovín of formula I having herbicidal compounds effect. These compounds can be prepared by reaction of substituted N-2,6-dialkylaniline- of formula II with arenesulfonyl isocyanate of Formula III in the medium an inert organic solvent of benzene, toluene, xylene, acetonitrile, chloroform, dichloromethane, tetrahydrofuran at a temperature of up to 120 ° C. in R 1 is H, Cl, CH 3 or methoxycarbonyl and R 2 and R 3 are CH 3 or ethyl and R4 is methoxy-C1-6alkyl.

Description

Vynález sa týká spósobu substituovaných N-/2,6-dialkylfenyl/-N'-arénsulfonylmočovín ako aj spósobu ich přípravy. Uvedené zlúčeniny sa móžu použiť ako herbicidy.The invention relates to a process for substituted N- (2,6-dialkylphenyl) -N'-arenesulfonylureas and to a process for their preparation. Said compounds can be used as herbicides.

Sulfonylmočoviny sú v patentovéj aj v ódborenej literatúre široko opísáné. Jedná sa napr.· o deriváty sulfónamidov s heterocyklickými amínmi ako sú aminotriazíny a aminopyrimidíny (Houben-Weyl: Methoden der organischen Chemie, 4 vydanie, zvSzok E 4, Georg Thieme Verlag, Stuttgart 1983, str. 400 až 402). Celý rad zlúčenín tejto skupiny má herbicídne resp. farmakologické vlastnosti. Menej sú známe zlúčeniny sulfónamidov so stéricky tienenými anilínmi (Atanasova, I. A. a spol.: Synthesis (8), 734 až 6 (1987)).Sulfonylureas are widely described in both patent and literature. These are, for example, sulfonamide derivatives with heterocyclic amines, such as aminotriazines and aminopyrimidines (Houben-Weyl: Methoden der organischen Chemie, 4th edition, Volume E 4, Georg Thieme Verlag, Stuttgart 1983, pp. 400-402). A number of compounds of this group have herbicidal or pharmacological properties. Less known are sulfonamide compounds with sterically shielded anilines (Atanasova, I. A. et al .: Synthesis (8), 734-6 (1987)).

Teraz sa zistili substituované N-/2,6-dialkylfenyl/-N'-arénsulfonylmočoviny všeobecného vzorca ISubstituted N- (2,6-dialkylphenyl) -N'-arenesulfonylureas of the formula I have now been found.

R2 R 2

2 3 vo ktorom R znamená vodík, chlor, metyl alebo metoxykarbonyl, R a R znamenajú metyl alebo 4 etyl a R znamená l-metoxy-2-propyl alebo 1-(metoxykarbonyl)-etyl.In which R is hydrogen, chlorine, methyl or methoxycarbonyl, R and R are methyl or 4-ethyl and R is 1-methoxy-2-propyl or 1- (methoxycarbonyl) ethyl.

Taktiež bo zistený spósob přípravy uvedených zlúčenín všeobecného vzorca I reakciou substituovaných N-2,6-dialkylanilínov všeobecného vzorca II p2 /Q)--NH-R4 '—/ /11/, 'r3 v ktorom R2, R3 a R4 majú už uvedený význam s arénsulfonylizokyanátom všeobecného vzorca IIIAlso disclosed is a process for the preparation of said compounds of formula I by reacting substituted N-2,6-dialkylanilines of formula II p2 (Q) -NH-R 4 '- (/ 11), wherein R 2 , R 3 and R 3 4 have the meanings already given with the arenesulfonyl isocyanate of the general formula III

/111/, v ktorom R3 má už uvedený význam, v prostředí inertného organického rozpúšťadla zo skupiny zahrňnujúcej benzén, toluén, xylén, acetonitril, chloroform, diichlórmetán, tetrahydrofurán pri teplote do 120 °C. Reakcia sa móže s výhodou uskutočniť za refluxu rozpúšťadla alebo v tlakovej nádobě.(111), in which R 3 is as defined above, in the presence of an inert organic solvent from the group consisting of benzene, toluene, xylene, acetonitrile, chloroform, dichloromethane, tetrahydrofuran at a temperature of up to 120 ° C. The reaction can advantageously be carried out at the reflux of the solvent or in a pressure vessel.

Reakciu je možné katalyzovať trietylamínom, pyridínom a podobné. Reakčné produkty sú v reakčnom prostředí po ochladení zmesi nerozpustné, dajú sa oddeliť od rozpúšťadla alebo reakčných zložiek například odsátím.The reaction can be catalyzed by triethylamine, pyridine and the like. The reaction products are insoluble in the reaction medium after cooling of the mixture and can be separated from the solvent or reactants, for example by suction.

Zlúčeniny všeobecného vzorca II - medziprodukty - je možné pripraviť postupmi známými z literatúry, ako je hydrogenačná alkylácia 2,6-dialkylanilínov ketónmi (BE 810 763, CS 219 856, US 4 200 451) alebo reakciou 2,6-dialkylanilínov s alkylbromidmi, alkylbenzénsulfonátmi alebo alkyltosylátmi, (DE 2 318 340) připadne alkyláciou 2,6-dialkylanilínov estermi kyseliny 2-halogénpropiónovej.Compounds of formula II - intermediates - can be prepared by methods known in the literature, such as the hydrogenation alkylation of 2,6-dialkylanilines with ketones (BE 810 763, CS 219 856, US 4 200 451) or by reacting 2,6-dialkylanilines with alkyl bromides, alkylbenzenesulfonates or alkyl tosylates, (DE 2 318 340) optionally by alkylation of 2,6-dialkylanilines with 2-halopropionic acid esters.

Východiskové zlúčeniny všeobecného vzorca III možno taktiež pripraviť známými postupmi, napr. rekaciou sulfónamidov s fosgénom (US 3 371 114, DOS 2 152 971, Ulrich, H. a spol.: Angew. Chem. 78, 761 (1966), Houben - Weyl: Methoden der organischen Chemie, 4. vydanie, zv. E 4, str. 803 až 810, Hagemann, Stuttgard, 1983).The starting compounds of formula III can also be prepared by known methods, e.g. by the reaction of sulfonamides with phosgene (U.S. Pat. No. 3,371,114, DOS 2,152,971, Ulrich, H. et al., Angew. Chem. 78, 761 (1966), Houben-Weyl: Methods of Organic Chemistry, 4th Edition, Vol. E 4, pp. 803-810, Hagemann, Stuttgard, 1983).

Substituované N-/2,6-dialkylfenyl/-N'-arénsulfonylmočoviny podlá vynálezu je možné použiť na ničenie burín. Na tento účel sa móžu upravit na roztoky, emulzie, suspenzie, prášky a pod. Tieto sa pripravujú známými spósobmi, například zmiešaním účinnej látky s pomocnýmiThe substituted N- (2,6-dialkylphenyl) -N'-arenesulfonylureas of the invention can be used to control weeds. 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 excipients

CS 266 985 Bl látkami ako sú kvapalné rozpúšťadla alebo tuhé nosné látky, připadne za použitia povrchovoaktívnych látok sú emulgátory alebo dispergátory.CS 266 985 B1 substances such as liquid solvents or solid carriers, optionally using surfactants, are emulsifiers or dispersants.

Nasledujúce příklady ilustrujú ale neobmedzujú predmet vynálezu.The following examples illustrate but do not limit the scope of the invention.

Příklad 1Example 1

K 4,15 g (0,02 molu) 2-metyl-6-etyl-N-/l'-metoxy-2'-propyl/anilínu v 30 ml cyklohexánu sa za miešania přidávalo postupné 3,9 g (0,02 molu) p-toluénsulfonylizokyanátu v 20 ml cyklohexánu. Po 2 hodinách reakcie začala vypadávat tuhá látka, ktorá sa na druhý deň odsala a premyla cyklohexánom. Získalo sa 6,75 g (84 %) N-/2-metyl-6-etylfenyl/-N-l'-metoxy-2'-propyl/-N'-p-toluénsulfonylmočoviny s t. t. 114,6 °C.To 4.15 g (0.02 mol) of 2-methyl-6-ethyl-N- (1'-methoxy-2'-propyl) aniline in 30 ml of cyclohexane was gradually added 3.9 g (0.02 mol) of p-toluenesulfonyl isocyanate in 20 ml of cyclohexane. After 2 hours of reaction, a solid began to precipitate, which was filtered off with suction the next day and washed with cyclohexane. 6.75 g (84%) of N- (2-methyl-6-ethylphenyl) -N-1'-methoxy-2'-propyl] -N'-p-toluenesulfonylurea with m.p. t. 114.6 ° C.

Pre C,.H,„N,O,S (404,53) vypočítané: C: 62,37; H: 6,98; N: 6,92; Z X 6 O Za 4For C 11 H 11 N 2 O 5 S (404.53) calculated: C: 62.37; H: 6.98; N: 6.92; Z X 6 O Za 4

S, 7,93 %, zistené: C, 62,7 %,S, 7.93%, found: C, 62.7%,

H, 7,0; N, 6,5; S, 7,8 %.H, 7.0; N, 6.5; S, 7.8%.

Rovnakým postupem boli připravené aj zlúčeniny uvedené v tabulke 1.The compounds listed in Table 1 were prepared in the same manner.

Tabulka 1Table 1

Zlúčenina Compound T. t. °C T. t. ° C Výťažok % Yield% Molová hmotnost Molar mass Analýza zistené/vypočítané Analysis found / calculated % C % C % H % H % N % N % S % WITH N-(2-metyl-6-etylfenyl)-N- N- (2-methyl-6-ethylphenyl) -N- 133,8 133.8 45 45 404,50 404.50 59,0 59.0 5,9 5.9 6,9 6.9 8,3 8.3 -£1- (metoxykarbonyl-etyj|-N'- -benzénsulfonylmočovina - 1- 1- (methoxycarbonyl-ethyl | -N'- -benzenesulfonylurea 59,38 59.38 5,98 5.98 6,93 6.93 7,92 7.92 N-(2-metyl-6-etylfenyl)-N- N- (2-methyl-6-ethylphenyl) -N- 59,8 59.8 6,3 6.3 6,7 6.7 8,0 8.0 -[Ir(metoxykarbony1)etyJ-N'- -o-toluénsulfonylmočovina - [Ir (methoxycarbonyl) ethyl] -N'- -o-toluenesulfonylurea 160,6 160.6 55 55 418,52 418.52 60,26 60.26 6,20 6.20 6,69 6.69 7,66 7.66 N- (2,6-dietylfenyl)-N-[l- N- (2,6-diethylphenyl) -N- [1- 147,1 147.1 48 48 432,55 432.55 61,4 61.4 6,6 6.6 6,4 6.4 7,3 7.3 -(metoxykarbonyl)-etyJ-N--o-toluénsulfonylmočovina- (methoxycarbonyl) -ethyl-N - -o-toluenesulfonylurea 61,08 61.08 6,52 6.52 6,48 6.48 7,41 7.41 N- (2-metyl-6-etylfenyl)-N-[l- N- (2-methyl-6-ethylphenyl) -N- [1- 138,3 138.3 40 40 418,52 418.52 60,2 60.2 6,1 6.1 6,6 6.6 7,9 7.9 -(metoxykarbonyl)-etyljN'- -p-toluénsulfonylmočovina - (methoxycarbonyl) -ethyl] N'- -p-toluenesulfonylurea 60,26 60.26 6,26 6.26 6,69 6.69 7,66 7.66 N- (2,6-dietylfenyl)-Ν-Γ1- N- (2,6-diethylphenyl) -Ν-Γ1- 138,2 138.2 47 47 432,55 432.55 61,5 61.5 6,4 6.4 6,4 6.4 7,7 7.7 -(metoxykarbonyl)-etylj-N'- -p-toluénsulfonylmočovina - (methoxycarbonyl) -ethyl] -N'- -p-toluenesulfonylurea 61,08 61.08 6,26 6.26 6,48 6.48 7,41 7.41 N-(2-metyl-6-etylfenyl)-N-[l- N- (2-methyl-6-ethylphenyl) -N- [1- 184,3 184.3 83,5 83.5 438,94 438.94 54,0 54.0 5,2 5.2 6,3 6.3 7,6 7.6 - (metoxykarbonyl) -etyl) N'-p- -chlorbenzensulfonylmočovina - (methoxycarbonyl) -ethyl) N'-p- -chlorobenzenesulfonylurea 54,72 54.72 5,28 5.28 6,38 6.38 7,31 7.31 N- (2,6-dietylfenyl)-N-Cl- N- (2,6-diethylphenyl) -N-Cl- 152,0 152.0 46 46 452,97 452.97 55,5 55.5 5,6 5.6 6,0 6.0 7,3 7.3 -(metoxykarbonyl)-etyljN'- -o-chlórbenzénsulfonylmočovina - (methoxycarbonyl) -ethyl] N'- -o-chlorobenzenesulfonylurea 55,68 55.68 5,56 5.56 6,18 6.18 7,08 7.08 N-(-2-metyl-6-etylfenyl)-N-Cl- N - (- 2-methyl-6-ethylphenyl) -N-Cl- • 147,6 • 147.6 38 38 462,54 462.54 57,5 57.5 5,6 5.6 6,4 6.4 7,2 7.2 -(metoxykarbonyl)-etyl J-N'-o-metoxykarbonyIbenzénsulfonylmočovina - (methoxycarbonyl) -ethyl J-N'-o-methoxycarbonylbenzenesulfonylurea 57,12 57.12 5,7 5.7 6,06 6.06 6,93 6.93 N- (2,6-dimetylfenyl)-N-Cl- (metoxykarbonyl)-etylJ-N'- N- (2,6-dimethylphenyl) -N-Cl- (methoxycarbonyl) -ethyl] -N'- 166,8 166.8 61 61 390,77 390.77 58,44 58.44 5,68 5.68 7,17 7.17 8,21 8.21 58,58 58.58 5,71 5.71 7,06 7.06 8,91 8.91 -benzénsulfonylmočovina -benzenesulfonylurea N-2,6-dimetyIfeny1-N-C1- N-2,6-dimethylphenyl-N-C1- 202,5 202.5 80 80 424,91 424.91 53,71 53.71 4,98 4.98 6,59 6,59 6.59 6.59 7,55 7.55 - (metoxykarbonyl)J-etyl/N'-o- -chlorbenzénsulfonylmočovina - (methoxycarbonyl) J-ethyl / N'-o- -chlorobenzenesulfonylurea 54,33 54.33 5,11 5.11 8,22 8.22 N-2,6-dimetylfenvl-N-(l- N-2,6-dimethylphenyl-N- (1- 151,8 151.8 67 67 404,49 404.49 59,39 59.39 5,98 5.98 6,93 6.93 7,93 7.93 -(metoxykarbonyiy-etyl/N-p- -toluénsulfonylmočovina - (methoxycarbonyl-ethyl) -N-p- -toluenesulfonylurea 59,22 59.22 6,05 6.05 6,87 6.87 7,50 7.50 N-/2-metyl-6-etylfenyl/-N/l'- N- (2-methyl-6-ethylphenyl) -N / 1'- 106,2 106.2 66 66 390,81 390.81 6,8 6.8 6,8 6.8 6,7 6.7 8,0 8.0 -metoxy-2'-propyl/-N'-benzén- -sulfonylmočovina -methoxy-2'-propyl] -N'-benzene- -sulfonylurea 61,50 61.50 6,71 6.71 7,17 7.17 8,21 8.21

II

CS 266 985 BlCS 266 985 Bl

Příklad 2Example 2

Do nádobiek z polyvinylchloridu (16,5x21x3 cm) naplněných štandardnou hlinitopiesčitou půdou sa ako testovacie objekty vysiali do.riadkov:In the containers made of polyvinyl chloride (16.5x21x3 cm) filled with standard aluminous-sandy soil, the following rows were sown as test objects:

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

Po urovnaní povrchu půdy sa urobila lahká zálievka vodou a povrch půdy sa ihned póstriekal přípravkami obsahujúcimi ako účinné látky zlúčeniny všeobecného vzorca I v koncentrácii 0,5 %. Přípravky sa použili v objeme 2 ml na nádobku, čo odpovedá dávke 2,5 kg.ha Ako Standard sa použil herbicid metolachlor. Stupeň poškodenia testovacích rastlín sa zistil na 21. deň po ošetření a vyjádřil sa bonitačnou stupnicou 0 až 5, v ktorej stupeň 0 znamená rastliny normálně rozvinuté, stupeň 5 znamená rastliny odumreté. Výsledky sú zhrnuté v tabulke 2.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 formulations were used in a volume of 2 ml per container, corresponding to a dose of 2.5 kg.ha The herbicide metolachlor was used as a standard. The degree of damage to the test plants was determined on 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.

Tabulka 2Table 2

Substituent Testovací objektSubstituent Test object

R1 R 1 R2 R 2 R3 R 3 R4 R 4 A A F F s with P P L L H H metyl methyl etyl ethyl 1-(metoxykarbonyl)-etyl' 1- (methoxycarbonyl) ethyl 2 2 3 3 2 2 3 3 3,5 3.5 2-metyl 2-methyl metyl methyl etyl ethyl 1-(metoxykarbonyl)-1-etyl 1- (methoxycarbonyl) -1-ethyl 2 2 3 3 2 2 4 4 2 2 2-metyl 2-methyl etyl ethyl etyl ethyl 1-(metoxykarbonyl) - -etyl 1- (methoxycarbonyl) - -ethyl 2 2 2 2 1 1 3,5 3.5 2 2 4-metyl 4-methyl metyl methyl etyl ethyl 1-(metoxykarbonyl)-etyl 1- (methoxycarbonyl) ethyl 2 2 3 3 1 1 3,5 3.5 0 0 4-metyl 4-methyl etyl ethyl etyl ethyl 1-(metoxykarbonyl)etyl ' 1- (methoxycarbonyl) ethyl ' 2 2 3 3 0 0 3,5 3.5 2 2 4-chlór 4-chlorine metyl methyl etyl ethyl 1-(metoxykarbonyl)-etyl 1- (methoxycarbonyl) ethyl 1 1 1 1 0 0 3,5 3.5 3,5 3.5 2-chlór 2-chlorine etyl ethyl etyl ethyl 1-(metoxykarbonyl)- -etyl 1- (methoxycarbonyl) - -ethyl 3 3 3 3 2 2 4 4 4 4 2-metoxykarbonyl 2-methoxycarbonyl metyl methyl etyl ethyl 1-(metoxykarbonyl)-etyl 1- (methoxycarbonyl) ethyl 2,5 2.5 3 3 2 2 3 3 2 2 H H metyl methyl metyl methyl 1-(metoxykarbonyl)- -etyl 1- (methoxycarbonyl) - -ethyl 1 1 2 2 0 0 2 2 2 2 2-chlór 2-chlorine metyl methyl metyl methyl 1-(metoxykarbonyl)-etyl 1- (methoxycarbonyl) ethyl 3,5 3.5 3,5 3.5 1 1 2 2 3,5 3.5 4-metyl 4-methyl metyl methyl metyl methyl 1-(metoxykarbonyl)etyl 1- (methoxycarbonyl) ethyl 2 2 0 0 0 0 3,5 3.5 2 2 H H metyl methyl etyl ethyl l-metoxy-2-propyl 1-methoxy-2-propyl 3 3 2 2 2 2 4 4 1 1 Standard Standard metolachlor metolachlor 3 3 3 3 4 4 2,5 2.5 3,5 3.5

CS 266 985 BlCS 266 985 Bl

Claims (2)

PREDMET VYNÁLEZUOBJECT OF THE INVENTION 1 - 2 3 v ktorom R znamená vodík, chlor, metyl alebo metoxykarbonyl, R a R znamenajú metyl alebo 4 etyl a R znamená l-metoxy-2-propyl alebo 1-(metoxykarbonyl)-etyl.1-2 in which R is hydrogen, chlorine, methyl or methoxycarbonyl, R and R are methyl or 4-ethyl and R is 1-methoxy-2-propyl or 1- (methoxycarbonyl) ethyl. 2. Spósob přípravy zlúčenín podia bodu 1 vyznaČujúci sa tým, že na substituovaný N-2,6-2. A process for the preparation of the compounds according to item 1, characterized in that the substituted N-2,6- -dialkylanilín všeobecného vzorca II ,2-dialkylaniline of general formula II, 2 NH-R4 NH-R 4 /1/,/ 1 /, 1. Substituované N-2,6-dialkylfenyl/-N'-arénsulfonylmočoviny všeobecného vzorca ISubstituted N-2,6-dialkylphenyl / -N'-arenesulfonylureas of the general formula I R2 R 2 2 3 4 v ktorom R , R a R majú už uvedený význam, sa pósobí arénsulfonylizokyanátom všeobecného vzorca IIIIn which R 1, R 2 and R 3 are as defined above, are treated with an arenesulfonyl isocyanate of the general formula III so2nco /111/, v ktorom R^ má už uvedený význam, v prostředí inertného organického rozpúšťadla zo skupiny zahrňujúcej benzén, toluén, xylén, acetonitril, chloroform, dichlórmetán, tetrahydrofurán pri teplote do 120 °C.with 2 nco (111), in which R 1 is as defined above, in the presence of an inert organic solvent from the group consisting of benzene, toluene, xylene, acetonitrile, chloroform, dichloromethane, tetrahydrofuran at a temperature of up to 120 ° C.
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