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 PDFInfo
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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
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- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims abstract description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000012948 isocyanate Substances 0.000 claims abstract description 3
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000008096 xylene Substances 0.000 claims abstract description 3
- -1 1-methoxy-2-propyl Chemical group 0.000 claims description 28
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 3
- 230000002363 herbicidal effect Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- KQRMGBSYWRUESQ-UHFFFAOYSA-N (2-chlorophenyl)sulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1Cl KQRMGBSYWRUESQ-UHFFFAOYSA-N 0.000 description 2
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- 240000008620 Fagopyrum esculentum Species 0.000 description 2
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- RUTYWCZSEBLPAK-UHFFFAOYSA-N (4-methylphenyl)sulfonylurea Chemical compound CC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 RUTYWCZSEBLPAK-UHFFFAOYSA-N 0.000 description 1
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 235000006463 Brassica alba Nutrition 0.000 description 1
- 244000140786 Brassica hirta Species 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- 244000211187 Lepidium sativum Species 0.000 description 1
- 235000007849 Lepidium sativum Nutrition 0.000 description 1
- AZEPYUPSYWCRBG-UHFFFAOYSA-N N-Carbamoyl-4-chlorobenzenesulfonamide Chemical compound NC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 AZEPYUPSYWCRBG-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000005005 aminopyrimidines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
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
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
CS 266 985 BlCS 266 985 Bl
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