NO753861L

NO753861L -

Info

Publication number: NO753861L
Application number: NO753861A
Authority: NO
Inventors: J Krenzer
Original assignee: Velsicol Chemical Corp
Priority date: 1975-04-14
Filing date: 1975-11-17
Publication date: 1976-10-15
Also published as: DE2548847A1; IN141388B; BR7601233A; ATA880375A; SU588904A3; DK144419B; YU278175A; JPS52100472A; SE418500B; IL48358A; YU39078B; FR2307811B1; JPS613789B2; CA1060022A; AT347452B; IL48358A0; SE7601766L; GB1545827A; IT1053288B; AU8574975A

Abstract

" Herbicide tiadiazolyl- acylimidazolidinoner'*.."Herbicide thiadiazolyl- acylimidazolidinones" * ..

Description

Foreliggende oppfinnelse gjelder herbicide tiadiazolyl-acylimidazolidinoner med den generelle formel: The present invention relates to the herbicidal thiadiazolyl-acylimidazolidinones with the general formula:

hvor R er alkyl, cykloalkyl, alkenyl, halogenalkyl, alkoksy, alkyltio, alkylsulfonyl eller alkylsulfinyl, R er alkyl, alkenyl, halogenalkyl eller: 4 5 3 hvor R og R er hydrogen eller alkyl, og R er alkyl, alkenyl, halogenalkyl, alkynyl, alkoksyalkyl, cykloalkyl eller: where R is alkyl, cycloalkyl, alkenyl, haloalkyl, alkoxy, alkylthio, alkylsulfonyl or alkylsulfinyl, R is alkyl, alkenyl, haloalkyl or: 4 5 3 where R and R are hydrogen or alkyl, and R is alkyl, alkenyl, haloalkyl, alkynyl , alkoxyalkyl, cycloalkyl or:

hvor X er alkyl, alkoksy, halogen, halogenalkyl, alkyltio, nitro eller cyano, n er et tall fra 0 til 3 og m er tallet 0 eller.1. where X is alkyl, alkoxy, halogen, haloalkyl, alkylthio, nitro or cyano, n is a number from 0 to 3 and m is the number 0 or 1.

Forbindelsene ifølge oppfinnelsen er uventet nyttige som herbicider. The compounds of the invention are unexpectedly useful as herbicides.

I en foretrukket utførelsesform av oppfinnelsen er R^* lavere alkyl, cykloalkyl med fra 3 til 7 karbonatomer, lavere alkenyl, lavere kloralkyl, lavere bromalkyl, trifluormetyl, lavere alkoksy, lavere alkyltio, lavere alkylsulfonyl eller lavere alkyl-2 sulfinyl, R er lavere alkyl, lavere alkenyl, lavere halogenalkyl eller: ; 4 5 hvor R og R er hydrogen eller alkyl med opp til 3 karbonatomer, R 3 er lavere alkyl, lavere alkenyl, lavere halogenalkyl, lavere alkynyl, lavere alkoksyalkyl, cykloalkyl med fra 3 til 7 karbonatomer ellers ; hvor X er lavere alkyl, lavere alkoksy, halogen, lavere halogenalkyl, nitro, cyano eller lavere alkyltio, n er et tall fra 0 til 3 og m er tallet 0 eller 1. Uttrykket "laveré" slik det brukes her, angir en lineær eller forgrenet karbonkjede med opp til 6 karbonatomer. ;Forbindelsene ifølge oppfinnelsen kan fremstilles ved å omsette en forbindelse med formelen: ; 12 hvor R og R er som beskrevet foran, med et syreanhydrid med formelen: 3 hvor R er som beskrevet foran, i nærvær av en katalytisk mengde p-toluensulfonsyre. Denne reaksjon kan gjennomføres ved å sammen-blande reaktantene og katalysatoren ved romtemperatur i et inert organisk reaksjonsmedium og så oppvarme reaksjonsblahdingen på et dampbad med omrøring i en periode på fra 1/2 til 4 timer. Deretter kan reaksjonsblandingen avkjøles og det ønskede produkt kan utvinnes ved filtrering om det oppnås et bunnfall eller ved fordampning av det organiske reaksjonsmediet om det er løselig i dette. I noen.tilfeller kan syreanhydridet anvendes som løsningsmiddel for en forbindelse med formel II, hvilket gjør anvendelse av et inert løsningsmiddel som reaksjonsmedium unødvendig. Når det anvendes lavere alkansyreanhydrider, kan vann tilsettes til reaksjonsblandingen for å felle ut det ønskede produkt når reaksjonen er avsluttet. Produktet kan så renses ved konvensjonelle metoder som f.eks. omkrystallisasjon og liknende. I noen tilfeller gir den forannevnte reaksjon som resultat at det dannes en blanding av produkter bestående av den ønskede forbindelse ifølge oppfinnelsen og dehydrert utgangsmateriale med formelen: ; 12 ;hvor R og R er som beskrevet. I disse tilfeller kan det ønskede produkt isoleres ved fraksjonert utfelling. ;Forbindelsene ifølge oppfinnelsen kan også fremstilles ved å omsette en forbindelse med formel II med et syfehalogenid med formelen: ; hvor R 3er som beskrevet foran, ionærvær av-en syreakseptor som f.eks. et tertiært amin. Denne frem3tillingsmetbde kan anvendes når det ønskede ahhydrid med formel III ikke er tilgjengelig. Denne reaksjon kan gjennomføres ved langsomt å tilsette syrekloridet méd formel V med omrøring til en løsning av en omtrent ekvimolar mengde av en forbindelse med formel II i et inert organisk løsningsmiddel, i nærvær av en syreakseptor ved en temperatur på fra ca. 10 til ;30°C. Etter at tilsetningen er ferdig, kan reaksjonsblandingen oppvarmes til en temperatur i området opp til tilbakeløpstempera-turen for blandingen for å sikre fullstendig reaksjon. Det ønskede produkt kan så utvinnes ved først å filtrere reaksjonsblandingen for å fjerne syreakseptorklbrid, deretter fordampe løsningsmidlet dersom produktet er løselig i løsningsmidlet eller, dersom det dannes som bunnfall ved å filtrere og deretter vaske og rense. ;Forbindelsene med formel II kan lett fremstilles ved å oppvarme en forbindelse med formelen: ; 12';hvor R og R er som beskrevet foran, i et fortynnet, vandig, surt reaksjonsmedium i fra ca. 10 til ca. 60 minutter. Temperaturer på ;fra ca. 70°C til tilbakeløpstempemtur for reaksjonsblandingen kan anvendes. Reaksjonsmediet kan omfatte en fortynnet vandig uorganisk syre som f.eks. saltsyre med en konsentrasjon på fra ca. 0,5 til ;ca. 5%. Når reaksjonen er avsluttet kan det ønskede produktet utvinnes som bunnfall ved å avkjøle reaksjonsblandingen. Dette produkt kan anvendes som sådant eller kan renses ytterligere ved ;hjelp av. konvensjonelle metoder som f.eks. omkrystallisasjon og liknende. ;Forbindelsene med formel VI kan fremstilles ved å om-;sette en mol av en isocyanatdimer med formelen:; hvor R3" er som beskrevet foran, med ca. to mol av en dimetylacetal med formelen: ; 2 ;hvor R er som beskrevet foran. Denne reaksjon kan gjennomføres ved å oppvarme en blanding av isocyanatdimeren og acetalen i et inert organisk reaksjonsmedium som f.eks. benzen ved tilbakeløps-temperaturen for reaksjonsblandingen. Oppvarming.under tilbakeløp kan fortsettes i en periode på fra ca. 2 til ca. 30minutter for å sikre fullstendig reaksjon. Deretter kan det ønskede produktet utvinnes ved fordampning av reaksjonsmediet og kan anvendes som sådant eller kan renses ytterligere ved hjelp av stahdardteknikker på området. ;Isocyanatdimeren med formel VII kan fremstilles ved å omsette en tiadiazol ned formelen: ; hvor R^er som beskrevet foran, med fosgen. Denne reaksjon kan ut-føres ved å tilsette en oppslemming eller løsning av tiadiazolen i et egnet organisk løsningsmiddel som f.eks. etylacetat til en mettet løsning av fosgen i et organisk løsningsmiddel som f.eks. etylacetat. Den resulterende blanding kan orarøres ved omgivelses-temperatur i en periode på fra ca. 4 til ca. 24 timer. Reaksjonsblandingen kan så renses ved å blåse nitrogengass gjennom den for å fjerne uomsatt fosgen. Det ønskede produkt kan så utvinnes ved filtrering dersom det har dannet bunnfall, eller ved fordampning dersom det er løselig i det løsningsmiddel som anvendes. Dette produkt kan anvendes som sådant eller kan renses ytterligere.som beskrevet . ;Eksempler på tiadiazoler med formel IX som kan anvendes;for fremstilling av forbindelsene ifølge oppfinnelsen er: 5-metyl-2-amino-l,3,4-tiadiazol, 5-etyl-2-amino-l,3,4-tiadiazol, 5-propyl-2-amino-l,3,4-tiadiazol, 5-t-butyl-2-amino-l,3,4-tiadiazol, 5-allyl-2-amino-l,3,4-tiadiazol, 5-pent-3-enyl-2-aminb-l,3,4-tiadiazol, 5-klormetyl-2-amino-l,3 ,4-tiadiazol, 5-/3-kloretyl-2-amino-l, 3 ,4-tiadiazol , 5-)J'-klorpropyl-2-amino-l, 3 ,4-tiadiazol, 5-triklormetyl-2-amino-l,3,4-tiadiazol, 5-trifluormetyl-2-amino-l,3,4-tiadiazol, 5-metoksy-2-amino-l,3,4-tiadiazol, 5-etoksy-2-amino-l,3,4-tiadiazol, 5-propoksy-2-amino-l,3,4-tiadiazol, 5-butyloksy-2-amin6-l,3,4-tiadiazol, 5-heksyloksy-2-amino-l,3,4-tiadiazol, 5-metyltio-2-amino-1,3.,4-tiadiazol, 5-etyltio-2-amino-l,3,4-tiadiazol, 5-propyl- ;tio-2-amino-l,3,4,-tiadiazol, 5-butyltio-2-amino-l,3,4,tiadiazol, ;5-metylsulfonyl-2-amino-l,3,4-tiadiazol, 5-etylsulfonyl-2-amino-1,3,4-tiadiazol, 5-butylsulfonyl-2-amino-l,3,4-tiadiazol, 5-metyl-sulfinyl-2-amirio-l,3,4-tiadiazol, 5-etylsulfinyl-2-amino-l,3,4-tiadiazol , 5-propylsulf inyl-2-amino-l , 3 ,4-tiadiazol , 5-butylsulfi-nyl-2-amino-l,3,4-tiadiazol og liknende. ;Eksempler på egnede acetaler med formel VIII for fremstilling av forbindelsene ifølge oppfinnelsen er 2-metylaminoacet-aldehyd-dimetylacetal, 2-etylaminoacetaldehyd-dimetylacetal, 2-propylaminoacetaldehyd-dimetylacetal, 2-butylaminoacetaldehyd-dimetylacetal, 2-pentylaminoacetaldehyd-dimétylacetal og 2-heksyl-aminoacetaldehyd-dimetylacetal. ;Eksempler på egnede syroanhydrider med formel niers eddiksyreanhydrid, propionsyreanhydrid, butansyreanhydrid, pentan-syreanhydrid, heksan»yreanhydrid, akrylsyreanhydrid, butensyre-anhydrid, pentensyreanhydrid, kloreddiksyreanhydrid, bromeddik-syreanhydrid,/?-klorbutansyreånhydrid, cykloheksylkarboksylsyre-anhydrid, benzosyreanhydrid, toluensyreanhydrid, 4-klorbenzosyre-anhydrid, 3-brombenzosyreanhydrid, 4-fluorbenzosyreanhydrid, 4-metoksybenzosyreanhydrid, 4-etoksybenzosyreanhydrid, 4-klormetyl-benzosyreanhydrid, 4-trifluormetylbe.nzosyrenhhydrid, 3,4,5-tri-klorbenzosyreanhydrid, 3-metyltiobenzosyreanhydrid, 3-etyltio-benzosyreanhydrid, 4-butyltiobenzosyreanhydrid, fenyleddiksyre-anhydrid, 4-metylfenyleddiksyreanhydrid, propynsyreanhydrid, butyn-syreanhydrid, metoksyeddiksyreanhydrid, /3-metoksypropionsyrean-hydrid, lf -etoksybutansyreanhydrid og liknende. ;Eksempler på egnede syreklorider med formel V som er nyttige ved fremstilling av forbindelsene ifølge oppfinnelsen er syrehalogenider av de samme ayrer nom er angitt ovenfor i eksemp-lene på syreanhydrider. ;Fremgangsmåten for fré:;astilling av forbindelsen ifølge oppfinnelsen er mer spesielt illustrert idé følgende eksempler. ;Eksempel 1;Fremstilling av 5-t-butyl-l,3,4-tiadiazol-2-yl-isocyanatdimer. ;En mettet løsning av fosgen i etylacetat (100 ml) ble innført i et reaksjonskar av glass som var utstyrt med en mekanisk omrører. En oppslemming av 5-t-butyl-2-amino-l,3,4,tiadiazol (10g) i etylacetat (300 ml) ble tilsatt til reaksjonskaret og den re sulterende blanding ble omrørt i ca. 16 timer hvorved det ble dannet et bunnfall.Reaksjonsblandingen ble så renset med nitrogengass for å fjerne uomsatt fosgen. Den rensede blanding ble så filtrert for å utvinne det ønskede produkt, 5-t-butyl-l,3,4-tiadi-åzol-2-yl-isocyanatdimer som et fast produkt med.et smeltepunkt på 261 til 263°C. ;Eksempel 2;Fremstilling av 2-/l-metyl-3=(5-t-butyl-l*3,4-tiadiazol-2-yl)ureido/- acetaldehyd-dimetylacetal. In a preferred embodiment of the invention, R^* is lower alkyl, cycloalkyl with from 3 to 7 carbon atoms, lower alkenyl, lower chloroalkyl, lower bromoalkyl, trifluoromethyl, lower alkoxy, lower alkylthio, lower alkylsulfonyl or lower alkyl-2 sulfinyl, R is lower alkyl, lower alkenyl, lower haloalkyl or: ; 4 5 where R and R are hydrogen or alkyl with up to 3 carbon atoms, R 3 is lower alkyl, lower alkenyl, lower haloalkyl, lower alkynyl, lower alkoxyalkyl, cycloalkyl with from 3 to 7 carbon atoms otherwise; where X is lower alkyl, lower alkoxy, halogen, lower haloalkyl, nitro, cyano or lower alkylthio, n is a number from 0 to 3 and m is the number 0 or 1. The term "lower" as used herein denotes a linear or branched carbon chain with up to 6 carbon atoms. ;The compounds according to the invention can be prepared by reacting a compound with the formula: ; 12 where R and R are as described above, with an acid anhydride of the formula: 3 where R is as described above, in the presence of a catalytic amount of p-toluenesulfonic acid. This reaction can be carried out by mixing the reactants and the catalyst at room temperature in an inert organic reaction medium and then heating the reaction mixture on a steam bath with stirring for a period of 1/2 to 4 hours. The reaction mixture can then be cooled and the desired product can be recovered by filtration if a precipitate is obtained or by evaporation of the organic reaction medium if it is soluble in it. In some cases, the acid anhydride can be used as a solvent for a compound of formula II, which makes the use of an inert solvent as a reaction medium unnecessary. When lower alkanoic anhydrides are used, water can be added to the reaction mixture to precipitate the desired product when the reaction is complete. The product can then be cleaned by conventional methods such as e.g. recrystallization and the like. In some cases, the aforementioned reaction results in the formation of a mixture of products consisting of the desired compound according to the invention and dehydrated starting material with the formula: ; 12 ; where R and R are as described. In these cases, the desired product can be isolated by fractional precipitation. The compounds according to the invention can also be prepared by reacting a compound of formula II with a cyanide halide of the formula: where R 3 is as described above, ionic presence of an acid acceptor such as e.g. a tertiary amine. This preparation method can be used when the desired hydride of formula III is not available. This reaction can be carried out by slowly adding the acid chloride of formula V with stirring to a solution of an approximately equimolar amount of a compound of formula II in an inert organic solvent, in the presence of an acid acceptor at a temperature of from about 10 to ;30°C. After the addition is complete, the reaction mixture can be heated to a temperature in the range up to the reflux temperature of the mixture to ensure complete reaction. The desired product can then be recovered by first filtering the reaction mixture to remove the acid acceptor chloride, then evaporating the solvent if the product is soluble in the solvent or, if it forms as a precipitate by filtering and then washing and purifying. ;The compounds of formula II can be easily prepared by heating a compound of the formula: ; 12'; where R and R are as described above, in a dilute, aqueous, acidic reaction medium in from approx. 10 to approx. 60 minutes. Temperatures of; from approx. 70°C to reflux temperature for the reaction mixture can be used. The reaction medium may comprise a dilute aqueous inorganic acid, such as e.g. hydrochloric acid with a concentration of from approx. 0.5 to approx. 5%. When the reaction is finished, the desired product can be recovered as a precipitate by cooling the reaction mixture. This product can be used as such or can be further purified with the help of. conventional methods such as recrystallization and the like. The compounds of formula VI can be prepared by reacting one mole of an isocyanate dimer with the formula: where R3" is as described above, with about two moles of a dimethyl acetal of the formula: ; 2 ; where R is as described above. This reaction can be carried out by heating a mixture of the isocyanate dimer and the acetal in an inert organic reaction medium such as e.g. benzene at the reflux temperature of the reaction mixture. Heating during reflux can be continued for a period of from approx. 2 to approx. 30 minutes to ensure complete reaction. The desired product can then be recovered by evaporation of the reaction medium and can be used as such or can be further purified using standard techniques in the field. ;The isocyanate dimer with formula VII can be prepared by reacting a thiadiazole down the formula: ; where R^ is as described above, with phosgene. This reaction can be carried out by adding a slurry or solution of the thiadiazole in a suitable organic solvent such as e.g. ethyl acetate to a saturated solution of phosgene in an organic solvent such as ethyl acetate. The resulting mixture can be stirred at ambient temperature for a period of from approx. 4 to approx. 24 hours. The reaction mixture can then be purified by blowing nitrogen gas through it to remove unreacted phosgene. The desired product can then be recovered by filtration if it has formed a precipitate, or by evaporation if it is soluble in the solvent used. This product can be used as such or can be further purified as described. Examples of thiadiazoles with formula IX which can be used for the preparation of the compounds according to the invention are: 5-methyl-2-amino-1,3,4-thiadiazole, 5-ethyl-2-amino-1,3,4-thiadiazole , 5-propyl-2-amino-1,3,4-thiadiazole, 5-t-butyl-2-amino-1,3,4-thiadiazole, 5-allyl-2-amino-1,3,4-thiadiazole , 5-pent-3-enyl-2-aminob-1,3,4-thiadiazole, 5-chloromethyl-2-amino-1,3,4-thiadiazole, 5-/3-chloroethyl-2-amino-1, 3,4-thiadiazole, 5-)J'-chloropropyl-2-amino-1, 3,4-thiadiazole, 5-trichloromethyl-2-amino-1,3,4-thiadiazole, 5-trifluoromethyl-2-amino- 1,3,4-thiadiazole, 5-methoxy-2-amino-1,3,4-thiadiazole, 5-ethoxy-2-amino-1,3,4-thiadiazole, 5-propoxy-2-amino-1, 3,4-thiadiazole, 5-butyloxy-2-amino-6-1,3,4-thiadiazole, 5-hexyloxy-2-amino-1,3,4-thiadiazole, 5-methylthio-2-amino-1,3. ,4-thiadiazole, 5-ethylthio-2-amino-1,3,4-thiadiazole, 5-propyl- ;thio-2-amino-1,3,4,-thiadiazole, 5-butylthio-2-amino-1 ,3,4,thiadiazole, ;5-methylsulfonyl-2-amino-1,3,4-thiadiazole, 5-ethylsulfonyl-2-amino-1,3,4-thiadiazole, 5-butylsulfonyl-2-amino-1, 3,4-thiadiazole, 5-methyl-sulfinyl-2-ami rio-1,3,4-thiadiazole, 5-ethylsulfinyl-2-amino-1,3,4-thiadiazole , 5-propylsulfinyl-2-amino-1 , 3 ,4-thiadiazole , 5-butylsulfinyl-2 -amino-1,3,4-thiadiazole and the like. Examples of suitable acetals with formula VIII for the preparation of the compounds according to the invention are 2-methylaminoacetaldehyde-dimethylacetal, 2-ethylaminoacetaldehyde-dimethylacetal, 2-propylaminoacetaldehyde-dimethylacetal, 2-butylaminoacetaldehyde-dimethylacetal, 2-pentylaminoacetaldehyde-dimethylacetal and 2-hexyl -aminoacetaldehyde-dimethyl acetal. Examples of suitable acid anhydrides of formula nines acetic anhydride, propionic anhydride, butanoic anhydride, pentanoic anhydride, hexane»ic anhydride, acrylic anhydride, butenoic anhydride, pentenoic anhydride, chloroacetic anhydride, bromoacetic anhydride, /?-chlorobutanic anhydride, cyclohexylcarboxylic anhydride, benzoic anhydride, toluene anhydride -chlorobenzoic anhydride, 3-bromobenzoic anhydride, 4-fluorobenzoic anhydride, 4-methoxybenzoic anhydride, 4-ethoxybenzoic anhydride, 4-chloromethyl-benzoic anhydride, 4-trifluoromethylbenzoic anhydride, 3,4,5-tri-chlorobenzoic anhydride, 3-methylthiobenzoic anhydride, 3-ethylthio -benzoic anhydride, 4-butylthiobenzoic anhydride, phenylacetic anhydride, 4-methylphenylacetic anhydride, propynic anhydride, butynic anhydride, methoxyacetic anhydride, /3-methoxypropionic anhydride, 1f -ethoxybutanoic anhydride and the like. Examples of suitable acid chlorides of formula V which are useful in the preparation of the compounds according to the invention are acid halides of the same types as are indicated above in the examples of acid anhydrides. The method for preparing the compound according to the invention is more particularly illustrated by the following examples. ;Example 1;Preparation of 5-t-butyl-1,3,4-thiadiazol-2-yl-isocyanate dimer. A saturated solution of phosgene in ethyl acetate (100 ml) was introduced into a glass reaction vessel equipped with a mechanical stirrer. A slurry of 5-t-butyl-2-amino-1,3,4,thiadiazole (10g) in ethyl acetate (300ml) was added to the reaction vessel and the resulting mixture was stirred for approx. 16 hours whereby a precipitate was formed. The reaction mixture was then purged with nitrogen gas to remove unreacted phosgene. The purified mixture was then filtered to recover the desired product, 5-t-butyl-1,3,4-thiadiazol-2-yl-isocyanate dimer as a solid product with a melting point of 261 to 263°C. ;Example 2;Preparation of 2-(1-methyl-3=(5-t-butyl-1*3,4-thiadiazol-2-yl)ureido/-acetaldehyde-dimethyl acetal.

En blanding av 5-t-butyl-l,3,4-tiadiazol-2-yl-isocyanatdimer (6 g) og benzen (50 ml) ble innført i et glassreaksjonskar utstyrt med en mekanisk omrører og en tilbakeløpskjøler. Reaksjonsblandingen ble oppvarmet under tiibakeløp under omrøring i ca. 5 minutter. Deretter ble benzenet fordampet fra reaksjonsblandingen og det oppnåddes en olje som ble fast ved henstand. Det resulterende faste stoff ble så omkrystallisert fra pentan for å oppnå A mixture of 5-t-butyl-1,3,4-thiadiazol-2-yl-isocyanate dimer (6 g) and benzene (50 ml) was introduced into a glass reaction vessel equipped with a mechanical stirrer and a reflux condenser. The reaction mixture was heated under reflux with stirring for approx. 5 minutes. The benzene was then evaporated from the reaction mixture and an oil was obtained which solidified on standing. The resulting solid was then recrystallized from pentane to give

det ønskede produkt, 2-/lTmetyl-3-(5-t-butyl-l,3,4-tiadiazol-2-yl)ureido/-acetaldehyd-dimetylacetal med smeltepunkt på 80-82°C. the desired product, 2-[1T-methyl-3-(5-t-butyl-1,3,4-thiadiazol-2-yl)ureido]-acetaldehyde dimethyl acetal with a melting point of 80-82°C.

Ek aempel 3 Example 3

Fremstilling av 1-(5-t-butyl-l,3,4-tiadiazol-2-yl)-3-metyl-5-hydroksy-1,3-imidazolidin-2-on. Preparation of 1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-hydroxy-1,3-imidazolidin-2-one.

2-/1-metyl-3-(5-t-butyl-l,3,4-tiadiazol-2-ylJureido/acet-aldehyd-dimetylacetal (16 g), konsentrert saltsyre (lo ml) og vann (500 ml) ble innført i et glassreaksjonskar utstyrt med en mekanisk omrører, et termometer og en tilbakeløpskjøler. Reaksjonsblandingen ble oppvarmet under tiibakeløp i ca. 15 minutter.Reak-sjonsblandingen ble filtrert varm og filtratet ble så avkjølt, hvorved det oppsto et bunnfall. Bunnfallet ble utvunnet ved filtrering, tørket og omkrystallisert frai en benzen-heksan-blanding for å gi det ønskede produkt, 1-(5-t-butyl-l,3,4-tiadiazol-2-yl)-3-metyl-•5-hydroksy-i,3-imidazoliditf-2-on,. med et smeltepunkt på 133-134°C. 2-/1-methyl-3-(5-t-butyl-1,3,4-thiadiazol-2-yljureido/acetaldehyde-dimethyl acetal (16 g), concentrated hydrochloric acid (10 ml) and water (500 ml) was introduced into a glass reaction vessel equipped with a mechanical stirrer, a thermometer and a reflux condenser. The reaction mixture was heated under reflux for about 15 minutes. The reaction mixture was filtered hot and the filtrate was then cooled, whereby a precipitate formed. The precipitate was recovered by filtration, dried and recrystallized from a benzene-hexane mixture to give the desired product, 1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-•5-hydroxy- i,3-imidazolidif-2-one, with a melting point of 133-134°C.

Eksempel 4Example 4

Fremstilling av l-(5-t-butyl-l,3,4-tiadiazol-2-yl)-3-metyl-5-acetyloksy-1,3-imidazolidin-2-on. Preparation of 1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-acetyloxy-1,3-imidazolidin-2-one.

1- (5-t-butyl-l, 3 ,4-t:Ladiazol-2-yl)-3-metyl-5-hydroksy-1,3-imidazolidin-2-on:;(70g), eddiksyreanhydrid (56 g) ' og en kata- 1-(5-t-butyl-1,3,4-t:Ladiazol-2-yl)-3-methyl-5-hydroxy-1,3-imidazolidin-2-one:; (70g), acetic anhydride (56 g) ' and a cata-

lytisk mengde toluensulfonsyre ble innført i et glassreaksjonskar utstyrt med en mekanisk omrører og et termometer. Reaksjonsblandingen ble oppvarmet på et dampbad med kontinuerlig omrøring i ca. 2 timer. Deretter ble vann (500 ml) tilsatt til reaksjonsblandingen hvorved det oppsto et bunnfall. Bunnfallet ble utvunnet ved filtrering og ble tørket i en ovn ved 60°C. Det tørkede produkt ble så omkrystallisert fra metanol for å gi det ønskede produkt, 1<-(5-t-butyl-l,3,4-tiadiazol-2-yl)-3-metyl-5-acetyloksy-l,3-imid-azdlidin-2-on, med smeltepunkt på 141°C. lytic amount of toluenesulfonic acid was introduced into a glass reaction vessel equipped with a mechanical stirrer and a thermometer. The reaction mixture was heated on a steam bath with continuous stirring for approx. 2 hours. Then water (500 ml) was added to the reaction mixture, whereby a precipitate formed. The precipitate was recovered by filtration and was dried in an oven at 60°C. The dried product was then recrystallized from methanol to give the desired product, 1<-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-acetyloxy-1,3- imid-azdlidin-2-one, with a melting point of 141°C.

Eksempel 5Example 5

Fremstilling av 5-trifluormetyl-l,3 ,4-tiadia::ol-2-yl-isocyanatdimer. Preparation of 5-trifluoromethyl-1,3,4-thiadia::ol-2-yl-isocyanate dimer.

En mettet løsning av fo&gen i etylacetat (100 ml) ble innført i et glassreaksjonskar utstyrt med en mekanisk omrører. En oppslemming av 5-triJ:lu6rnietyl-2-amino-l,3 ,4-tiadiazol (45 g) i etylacetat (300ml) ble tilsatt til reakfjjonskafet og den resulterende blanding ble omrørt i c:a. 16 timer, hvorved det oppsto et bunnfall. Nitrogengass ble så boblet gjennom reaksjonsblandingen for å fjerne uomsatt fosgen. Den rensede blanding ble filtrert slik at det ble oppnådd 48 g av et hvitt fast stoff. Dette faste stoff ble omkrystallisert fra dimetylformamid slik at det ønskede produkt, 5-trifluormetyl-l,3,4-tiadiazol-2-yl-isocyanatdimer, ble oppnådd. A saturated solution of fo&gen in ethyl acetate (100 ml) was introduced into a glass reaction vessel equipped with a mechanical stirrer. A slurry of 5-trifluoromethyl-2-amino-1,3,4-thiadiazole (45 g) in ethyl acetate (300 ml) was added to the reaction mixture and the resulting mixture was stirred at c:a. 16 hours, during which a precipitate formed. Nitrogen gas was then bubbled through the reaction mixture to remove unreacted phosgene. The purified mixture was filtered to give 48 g of a white solid. This solid was recrystallized from dimethylformamide so that the desired product, 5-trifluoromethyl-1,3,4-thiadiazol-2-yl-isocyanate dimer, was obtained.

Eksempel 6 Example 6

Fremstilling av 2-/I-metyl-3-(5-trifluormetyl-l,3,4-tiadiazol-2-yl)-ureido/acetaldehyd-dimetylacetal. Preparation of 2-(1-methyl-3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-ureido/acetaldehyde-dimethyl acetal.

En blanding av 5-trif.luormetyi-l,3 ,4-tiadiazol-2-yl-isocyanatdimer (9,5 g), 2-metylnmiiioacetaldehyd-dimetylacetal (5,8 g) og benzen (60 ml), innføres i et glassreaksjonskar utstyrt .med en mekanisk omrører og en tilbakeløpskjøler. Reaksjonsblandingen oppvarmes under tiibakeløp i ca. 15 minutter. Deretter fjernes benzen fra blandingen under redusert trykk slik at det oppstår et fast produkt som rest. Dette produkt omkrystalliseres fra heptan slik at det ønskede produkt 2-,/i-rmetyl-3-(5-trifluormetyl-l,3 ,4-tiadiazol-2-yl)ureidq7acetaldehyd-dimetylacetal med smeltepunkt på lol-102°C, oppnås. A mixture of 5-trifluoromethyl-1,3,4-thiadiazol-2-yl-isocyanate dimer (9.5 g), 2-methylnimiioacetaldehyde-dimethyl acetal (5.8 g) and benzene (60 ml) is introduced into a glass reaction vessel equipped with a mechanical stirrer and a reflux condenser. The reaction mixture is heated under reflux for approx. 15 minutes. Benzene is then removed from the mixture under reduced pressure so that a solid product is formed as a residue. This product is recrystallized from heptane so that the desired product 2-,1-methyl-3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)ureidq7acetaldehyde-dimethylacetal with a melting point of 10-102°C is obtained .

Eksempel 7Example 7

Fremstilling av l-(5-trifluormetyl-l,3,4-tiadiazol-2-yl)-3-métyl-5-hydroksy-l,3-imidazolidin-2-on. Preparation of 1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-hydroxy-1,3-imidazolidin-2-one.

2-/l-metyl-3-(5-trifluormetyl-1,3,4-tiadiazol-2-yl)-ureido/acetaldehyd-dimetylacetal (15 g), vann (400 ml) og saltsyre (4 ml) ble innført i et glassreaksjonskar utstyrt med en mekanisk omrører, et termometer og en tilbakeløpskjøler. Reaksjonsblandingen ble oppvarmet under tiibakeløp i ca. 15 minutter. Re-aks jonsblandingen ble så filtrert varm og filtratet ble avkjølt slik at det oppsto et bunnfall. Bunnfallet ble utvunnet ved filtrering, ble tørket og omkrystallisert fra en blanding av etylacetat og heksan slik at det ønskede produkt, 1-(5-trifluormetyl-1,3,4-tiadiåzol-2-yl)-3-metyl-5-hydroksy-l,3-imidazolidin-2-on med smeltepunkt på 136-138°C, ble oppnådd. 2-(1-methyl-3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-ureido/acetaldehyde-dimethyl acetal (15 g), water (400 ml) and hydrochloric acid (4 ml) were introduced in a glass reaction vessel equipped with a mechanical stirrer, a thermometer and a reflux condenser. The reaction mixture was heated under reflux for approx. 15 minutes. The reactive ion mixture was then filtered hot and the filtrate was cooled to form a precipitate. The precipitate was recovered by filtration, was dried and recrystallized from a mixture of ethyl acetate and hexane to give the desired product, 1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-hydroxy -1,3-imidazolidin-2-one with a melting point of 136-138°C was obtained.

Eksempel 8Example 8

Fremstilling av 1-(5-trifluormetyl-1,3,4-tiadiazol-2-yl)-3-metyl-5-acetyloksy-l, 3-imidazol.idin-2-on. Preparation of 1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-acetyloxy-1,3-imidazolidin-2-one.

1-(5-trifluormetyl-1,3,4-tiadiazol-2-yl)-3-metyl-5-hydroksy-1,3-imidazolidin-2-on (0,05 mol), eddiksyreanhydrid («6 ml), eddiksyre (20 ml) og toluensulfonsyre (0,1 g) innføres i et glass-reaks jonskar utstyrt med en mekanisk omrører og et termometer. Reaksjonsblandingen omrøres ved romtemperatur i ca. 24 timer. Deretter tilsettes vann (200ml) til reaksjonsblandingen. Den resulterende blandingen ekstraheres så med eter.Eterekstrakten vaskes med vandig natriumkarbonat og tørkes over vannfritt magnesiumsul-fat. Den tørkede løsningen filtreres så og løsningsmidlet fjernes under redusert trykk slik at det oppnås en fast rest. Denne faste rest omkrystalliseres fra en vann-metanol-blariding slik at det ønskede produkt, 1-(5-trifluormetyl-l,3,4-tiadiazol-2-yl)-3-metyl-5-acétyloksy-l,3-imidazolidin-2-on oppnå» som et krystallisk fast stoff med smeltepunkt på 72-74°C. 1-(5-Trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-hydroxy-1,3-imidazolidin-2-one (0.05 mol), acetic anhydride («6 ml) , acetic acid (20 ml) and toluenesulfonic acid (0.1 g) are introduced into a glass reaction vessel equipped with a mechanical stirrer and a thermometer. The reaction mixture is stirred at room temperature for approx. 24 hours. Water (200 ml) is then added to the reaction mixture. The resulting mixture is then extracted with ether. The ether extract is washed with aqueous sodium carbonate and dried over anhydrous magnesium sulfate. The dried solution is then filtered and the solvent is removed under reduced pressure to give a solid residue. This solid residue is recrystallized from a water-methanol reflux so that the desired product, 1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-acetyloxy-1,3-imidazolidine -2-one obtain" as a crystalline solid with a melting point of 72-74°C.

Ytterligere forbindelser ifølge oppfinnelsen som kan fremstilles ved fremgangsmåtene i de foregående eksempler er; Further compounds according to the invention which can be prepared by the methods in the preceding examples are;

1-(5-heksyl-l,3,4-tiadiazol-2-yl)-3-etyl-5-acetylbksy-l,3-imid-azolidin-2-on, 1-(5-t-butyl-l,3,4-tiadiazolA2-yl)-3-metyl-5-pro-pionyloksy-l,3-imidazolidin-2-on, 1-(5-trifluormetyl-1,3,4-tiadiazol-2-yl)-3-metyl-5-butanoyloksy-l,3-imidazolidin-2-on, l-(5-pentyl-'l, 3 ,4-tiadiazol-2-yl)-3-etyi-5-akryloyloksy-l, 3-imidazol-idin-2-on, l-<(5-Jt-butyl-l, 3 ,4-tiadiazol-2-yl)-3-propyl-5-klor-acetyloksy-1,3-imidazolidin-2-on, 1-(5-t-butyl-l;3,4-tiadiazol-2-yl)-3-allyl-5-cykloheksylkarbonyloksy-l,3-imidazolidin-2-on, l-(5- 1-(5-hexyl-1,3,4-thiadiazol-2-yl)-3-ethyl-5-acetylboxy-1,3-imidazolidin-2-one, 1-(5-t-butyl-1 ,3,4-thiadiazolA2-yl)-3-methyl-5-prop-pionyloxy-1,3-imidazolidin-2-one, 1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)- 3-methyl-5-butanoyloxy-1,3-imidazolidin-2-one, 1-(5-pentyl-1,3,4-thiadiazol-2-yl)-3-ethyl-5-acryloyloxy-1,3 -imidazol-idin-2-one, 1-<(5-Jt-butyl-1,3,4-thiadiazol-2-yl)-3-propyl-5-chloro-acetyloxy-1,3-imidazolidin-2- one, 1-(5-t-butyl-1;3,4-thiadiazol-2-yl)-3-allyl-5-cyclohexylcarbonyloxy-1,3-imidazolidin-2-one, l-(5-

tri fluormetyl-1,3,4-tiadiazol-2-yl)-3-klormetyl-5-acetyloksy-l,3-imidazolidin-2-on, 1-(5-trifluormetyl-l,3,4-tiadiazol-2-yl)-3-propargyl-5-(3-metylbénzoyloksy) -1,3-imidazo.lidin-2-on, 1- (5-trifluormetyl-l, 3,4-tiadiazol-2-yl)-3-metyl-5-(4-klorbenzoyloksy)-1,3-imidazolidin-2-on, 1-(5-t-butyl-l,3,4-tiadiazol-2-yl)-3-(1,1-dimetylprop-2-ynyl)-5-(4-metoksybenzoyloksy)-1,3-imidazolidin-2-on, 1- (5-t-butyl-l,3,4-tiadiazol-2-yl)-3-metyl-5-(4-trifluormetyl-benzoyloksy)-l,3-imidazolidin-2-on, 1-(5-trifluormetyl-l,3,4-tiadiazol-2-yl)-3-metyl-5-(4-metyltiobenzoyloksy)-1,3-imidazolidin-2- on, 1-(5-trifluormetyl-l,3,4-tiadiazol-2-yl)-3-etyl-5-acetyloksy-1,3-imidazolidin-2-on, 1-(5-trifluormetyl-1,3,4-tiadiazol-2-yl)-3- etyl-5-metoksyacetyloksy-l.3-imidazolidin-2-on, 1-(5-t-butyl-1,3 ,4-tiadiazol-2-yl)-3-metyl-5- (3-metylfeny.l-acetyloksy-l, 3-imid-azolidin-2-on, 1-(5-trifluormetyl-1,3,4-tiadiazol-2-yl)-3-metyl-5-propynoyloksy-l, 3-imidaj:olidin-2-on, 1- (5-trifluormetyl-l ,3 ,4-tiadiazol-2-yl)-3-propyl-5-(3-cyanobenzoyloksy)-1,3-imidazolidin-2-on, 1-(5- sek-butyl-l,3,4-tiadiazol-2-yl)-3-propyl-5-(4-nitro-benzoyloksy)-l,3-imidazolidin-2-on, 1-(5-t-butyl-l,3,4-tiadiazol-2-yl)-3-propyl-5-benzoylok!:»y-l,3-imidazolidin-2-on, l-(5-trifluormetyl-l ,3,4-tiadiazol-2-yl)-3-propyl-5-benzoyloksy-l,3-imid-azolidin-on, 1-(5-etyl-l,3,4-tiadiazol-2-yl)-3-etyl-5-acetyloksy-1,3-imidazolidin-2-on, 1-(5-propyl-l,3,4-tiadiazol-2-yl)-3-propyl-5-propanoyloksy-l,3-imidazolidin-2-on, 1-(5-butyl-l,3,4-tiadiazol-2-yl) -3r-butyl-5-butanoyloksy-l, 3-imidazolidin-2-on, 1- (5-pentyl-1,3,4-tiadiazol-2-yl)-3-pentyl-5-pentanoyloksy-l,3-imidazolidin-2-on, 1-(5-heksyl-l,3,4-tiadiazol-2-yl)-3-heksyl-5-heksanoyloksy-1,3-imidazolidin-2-on, 1-(5-cykloheptyl)-l,3,4-tiadiazol-2-yl)-3-but-3-enyl-5-pent-4-enoyloksy-l,3-imidazolidin-2-on, 1-(5-but-2-enyl-1,3 ,4-tiacLiazol-2-yl,)-3~pent-4-ényl-5-heks-4-enoylbksy-l ,3-imidazolidin-2-on, 1-(5-pent-3-enyl-l,3,4-tiadiazol-2-yl)-3-heks-5-enyl-5-tt-kloracétyloksy-l, 2-imidazo.lidin-2-on, ' 1- (5-heks-4-enyl-1,3 ,4-tiadiazol-2-yl)-3-af-kloretyl-5-^-brombutanoyloksy-l,3-imid-azolidin-2-on, 1- (5-/9-kloretyl-l, 3 ,4-tiadiazol-2-yl)-3-iodmetyl-5-J-klorpentanoyloksy-l, 3-imidazolidin-2-on, 1- (5-if-klorpropyl-1,3 ,4-tiadiazol-2-yl )-3-trifluormetyl-5-k>-klorheksan6yloksy-l, 3-imidazolidin-2-on, lv(5-brom-metyl-l,3,4-tiadiazol-2-yl)-3-0-klor-etyl-5-a-jodacetyloksy-1,3-imidazo.lidih-2-on, 1- (5-0-brometyl-1,3,4-tiadiazol-2-yl)-brompropyl-5-cyklopropylkarbonyloksy-1,3-imidazolidin-2-on, 1-(5-triklormetyl-l,3,4-tiadiazol-2-yl)-3- trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-chloromethyl-5-acetyloxy-1,3-imidazolidin-2-one, 1-(5-trifluoromethyl-1,3,4-thiadiazol-2 -yl)-3-propargyl-5-(3-methylbenzoyloxy)-1,3-imidazo.lidin-2-one, 1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3- methyl 5-(4-chlorobenzoyloxy)-1,3-imidazolidin-2-one, 1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-(1,1-dimethylprop -2-ynyl)-5-(4-methoxybenzoyloxy)-1,3-imidazolidin-2-one, 1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl- 5-(4-trifluoromethyl-benzoyloxy)-1,3-imidazolidin-2-one, 1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-(4-methylthiobenzoyloxy )-1,3-imidazolidin-2-one, 1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-ethyl-5-acetyloxy-1,3-imidazolidin-2-one, 1-(5-Trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-ethyl-5-methoxyacetyloxy-1,3-imidazolidin-2-one, 1-(5-t-butyl-1,3 ,4-thiadiazol-2-yl)-3-methyl-5-(3-methylphenyl-1-acetyloxy-1,3-imid-azolidin-2-one, 1-(5-trifluoromethyl-1,3,4- thiadiazol-2-yl)-3-methyl-5-propynoyloxy-1,3-imidaj:olidin-2-one, 1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3- propyl-5-(3-cyanobenzoyloxy)-1,3-imidazolidin-2-one, 1-(5-sec-butyl-1,3,4-thiadiazol-2-yl)-3-propyl-5-(4 -nitro-benzoyloxy)-1,3-imidazolidin-2-one, 1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-propyl-5-benzoyloxyl-1, 3-Imidazolidin-2-one, 1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-propyl-5-benzoyloxy-1,3-imidazolidin-one, 1-(5 -ethyl-1,3,4-thiadiazol-2-yl)-3-ethyl-5-acetyloxy-1,3-imidazolidin-2-one, 1-(5-propyl-1,3,4-thiadiazol-2 -yl)-3-propyl-5-propanoyloxy-1,3-imidazolidin-2-one, 1-(5-butyl-1,3,4-thiadiazol-2-yl)-3r-butyl-5-butanoyloxy- 1,3-imidazolidin-2-one, 1-(5-pentyl-1,3,4-thiadiazol-2-yl)-3-pentyl-5-pentanoyloxy-1,3-imidazolidin-2-one, 1- (5-hexyl-1,3,4-thiadiazol-2-yl)-3-hexyl-5-hexanoyloxy-1,3-imidazolidin-2-one, 1-(5-cycloheptyl)-1,3,4- thiadiazol-2-yl)-3-but-3-enyl-5-pent-4-enoyloxy-1,3-imidazolidin-2-one, 1-(5-but-2-enyl-1,3 ,4- thiacLiazol-2-yl,)-3~pent-4-enyl-5-hex-4-enoylboxy-1,3-imidazolidin-2-one, 1-(5-pent-3-enyl-1,3,4 -thiadiazol-2-yl)-3-hex-5-enyl-5-tt-chloroacetyloxy-1, 2-imidazo. lidin-2-one, 1-(5-hex-4-enyl-1,3,4-thiadiazol-2-yl)-3-α-chloroethyl-5-β-bromobutanoyloxy-1,3-imidazolidine -2-one, 1-(5-(9-chloroethyl-1,3,4-thiadiazol-2-yl)-3-iodomethyl-5-J-chloropentanoyloxy-1,3-imidazolidin-2-one, 1- (5-if-chloropropyl-1,3,4-thiadiazol-2-yl)-3-trifluoromethyl-5-k>-chlorohexan6yloxy-1, 3-imidazolidin-2-one, lv(5-bromo-methyl-1 ,3,4-thiadiazol-2-yl)-3-0-chloro-ethyl-5-a-iodoacetyloxy-1,3-imidazo.lidih-2-one, 1-(5-0-bromomethyl-1,3 ,4-thiadiazol-2-yl)-bromopropyl-5-cyclopropylcarbonyloxy-1,3-imidazolidin-2-one, 1-(5-trichloromethyl-1,3,4-thiadiazol-2-yl)-3-

£-rbromheksyl-5-cyklobutylkarbonyloksy-l, 3-imidazolidin-2-on, 1-(5-^-klorheksyl-l, 3 ,4-tiadiazol-2-yl)-3-/S-klorheksyl-5-cyklopentyl-karbonyloksy-l,3-imidazolidin-2-on, 1-(5-etoksy-l,3,4-tiadiazol-2- yl)-3-(1,l-dietylprop-2-ynylj-5-cykloheptylkarbonyloksy-l,3-imidazolidin-2-on, 1-(5-butoksy-l,3,4-tiadiazol-2-yl)-3-(1,1-di-propylprop-2-ynyl)-5-(2-etylbenzoyloksy)-1,3-imidazolidin-2-on, 1- (5rheksyloksy-l,3,4-tiadiazol-2-yl)-3-metyl-5-(3-propylbenzoyl-oksy)-1,3-imidazolidin--2-on, 1- (5-etyltio-i,3,4-tiadiazol-2-yl)-3- metyl-5- (4-heksylbenzoyloksy)-1,3-imidazolidin-2-on, 1 ,-.C5-prop-yltio-1,3,4-tiadiazol-2-yl)-3-metyl-5-(3-etoksybenzoyloksy)-1,3-imidazolidin-2-on, 1-(5-pentyltio-l,3,4-tiadiazol-2-yl)-3-metyl-5- (4-butoksyben3:oyloksy)-l,3-imidazolidin-2-on, l-(5-heksyltio-1, 3 ,4-tiadiazoi-r2-yl )-3-metyl-5- (4-heksyloksybenzoyloksy)-l, 3-imidazolidin-2-on, 1-(5 etyisulfonyl-1,3,4-tiadiazpl-2-yl) -3-metyl-5-(4-brombenzoyloksy)-l, 3--imidazolidin-2-on, 1- (5-propyl-sulfonyl-1,3,4-tiadiazol-2-yl)-3-metyl-5~(4-jodbehzoyloksy)-l,3-imidazolidin-2-on, 1-(5-pentylsulfonyl-l,3,4-tiadiazol-2-yl)-3-metyl-5-(4-fluorbenzoyloksy)1,3-rimidazolidin-2-on, i-(5-heksyl-sulfonyl-1,3,4-tiadiazol-2-yl)-3-metyl-5-(2,4-diklorbenzoyloksy)-1,3-imidazolidin-2-on, 1-(5-etylsulfinyl~l,3,4-tiadiazol-2-yl)-3-metyl-5-(2,4,6-triklorbenzoyloksy)-i,3-imidazolidin-2-on, l-(5-propylsulfinyl-1,3,4-tiadiazol-2-yl)-3-metyl-5-(3,4-dibrombenzoyl-oksy)-1,3-imidazolidin-2-on, 1-(5-butylsulfinyl-1,3,4-tiadiazol-2- yl)-3-metyl-5-(4-trifluormetylbenzoyloksy)-!,3-imidåzolidin-2-on, 1-(5-heksylsulfinyl-1,3, 4- tiadiazol-2-yl)-3-metyl-5-(4-klor-metylbenzoyloksy)-1,3-imidazolidin-2-on, 1-(5-isopropyl-l,3,4-tiadiazol-2-yl)-3-metyl-5-alkyltiobenzoyloksy-l,3-imidazolidin-2-on, 1-(5-isopropyl-l,3,4-tiadiazol-2-yl)-3-metyl-5-propyltio-benzoyloksy-1,3-imidazolidin-2-on, 1-(5-isopropyl^l,3,4-tiadiazol-2-yl)-3-metyl-5-péntyltiobenzoyloksy-l,3-imidazplidin-2-on, 1-(5-isopropyl-1,3,4-tiadiazol-2-yi)-3-metyl-5-hekByltiobenzoyloksy-1,3-imidazolidin-2-on, 1-(5-metyl-l,3,4-tiadiazol-2-yl)-3-metyl-5-butynoyloksy-l,3-imidazoiidin-2-on, 1-(5-metyl-l,3,4-tiadiazol-2-yl)-3-metyl-5-pent-4-ynyloksy-i,3-imidazolidin-2-on, 1-(5-metyl-1,3,4-tiadiazol-2-yl)-3-metyl-5-heks-4-ynyloksy-l,3-imidazolidih-2- oh, l-(5-metyl-l,3;4-tiadiazol-2-ylJ-i-metyl-S-Ø-metoksypropio-nyloksy-l ,3-imidazolidin-2-on, 1-(5-metyl-l,3,4-tiadiazol-2-yl)-3- metyl-5-y-metoksybutanoyloksy-l,3-imidazolidin-2-on, 1-(5-metyl-1,3,4-tiadiazol-2-yl)-3-metyl-5-^-metoksypentanoyloksy-l,3-imid- azolidin-2-on, 1-(5-metyl-l',3,4-tiadiazol-2-yl)-3-metyl-5-0-etoksypropionyloksy-l,3-imidazolidin-2-on, 1-(5-metyl-l,3,4-tia-A diazol-2-yl)-3-metyl-5-propoksyacetyloksy-l,3-imidazolidin-2-on, 1- (5-metyl-l,3,4-tiadiazol-2-yl)-3-metyl-5-butoksyacetyloksy-l,3- £-rbromohexyl-5-cyclobutylcarbonyloxy-1, 3-imidazolidin-2-one, 1-(5-β-chlorohexyl-1, 3,4-thiadiazol-2-yl)-3-/S-chlorohexyl-5-cyclopentyl -carbonyloxy-1,3-imidazolidin-2-one, 1-(5-ethoxy-1,3,4-thiadiazol-2-yl)-3-(1,1-diethylprop-2-ynyl-5-cycloheptylcarbonyloxy- 1,3-imidazolidin-2-one, 1-(5-butoxy-1,3,4-thiadiazol-2-yl)-3-(1,1-di-propylprop-2-ynyl)-5-(2 -ethylbenzoyloxy)-1,3-imidazolidin-2-one, 1-(5-hexyloxy-1,3,4-thiadiazol-2-yl)-3-methyl-5-(3-propylbenzoyl-oxy)-1,3- imidazolidin-2-one, 1-(5-ethylthio-i,3,4-thiadiazol-2-yl)-3-methyl-5-(4-hexylbenzoyloxy)-1,3-imidazolidin-2-one, 1 ,-.C5-prop-ylthio-1,3,4-thiadiazol-2-yl)-3-methyl-5-(3-ethoxybenzoyloxy)-1,3-imidazolidin-2-one, 1-(5-pentylthio -1,3,4-thiadiazol-2-yl)-3-methyl-5-(4-butoxyben3:oyloxy)-1,3-imidazolidin-2-one, 1-(5-hexylthio-1,3,4 -thiadiazoi-2-yl)-3-methyl-5-(4-hexyloxybenzoyloxy)-1,3-imidazolidin-2-one, 1-(5-ethylsulfonyl-1,3,4-thiadiazpl-2-yl)-3 -methyl-5-(4-bromobenzoyloxy)-1,3-imidazolidin-2-one, 1-(5-propyl-sulfonyl-1,3,4-thiade iazol-2-yl)-3-methyl-5-(4-iodobezoyloxy)-1,3-imidazolidin-2-one, 1-(5-pentylsulfonyl-1,3,4-thiadiazol-2-yl)-3 -methyl-5-(4-fluorobenzoyloxy)1,3-rimidazolidin-2-one, i-(5-hexyl-sulfonyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-(2 ,4-dichlorobenzoyloxy)-1,3-imidazolidin-2-one, 1-(5-ethylsulfinyl~1,3,4-thiadiazol-2-yl)-3-methyl-5-(2,4,6-trichlorobenzoyloxy )-i,3-imidazolidin-2-one, 1-(5-propylsulfinyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-(3,4-dibromobenzoyl-oxy)-1, 3-imidazolidin-2-one, 1-(5-butylsulfinyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-(4-trifluoromethylbenzoyloxy)-1,3-imidazolidin-2-one, 1-(5-hexylsulfinyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-(4-chloro-methylbenzoyloxy)-1,3-imidazolidin-2-one, 1-(5-isopropyl -1,3,4-thiadiazol-2-yl)-3-methyl-5-alkylthiobenzoyloxy-1,3-imidazolidin-2-one, 1-(5-isopropyl-1,3,4-thiadiazol-2-yl )-3-methyl-5-propylthio-benzoyloxy-1,3-imidazolidin-2-one, 1-(5-isopropyl^1,3,4-thiadiazol-2-yl)-3-methyl-5-pentylthiobenzoyloxy- 1,3-Imidazplidin-2-one, 1-(5-isopropyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-hexylthiobenz oyloxy-1,3-imidazolidin-2-one, 1-(5-methyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-butynoyloxy-1,3-imidazoiidin-2-one, 1-(5-methyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-pent-4-ynyloxy-1,3-imidazolidin-2-one, 1-(5-methyl-1 ,3,4-thiadiazol-2-yl)-3-methyl-5-hex-4-ynyloxy-1,3-imidazolidih-2- oh,l-(5-methyl-1,3;4-thiadiazole-2 -ylJ-i-methyl-S-Ø-methoxypropionyloxy-1,3-imidazolidin-2-one, 1-(5-methyl-1,3,4-thiadiazol-2-yl)-3-methyl-5 -γ-methoxybutanoyloxy-1,3-imidazolidin-2-one, 1-(5-methyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-^-methoxypentanoyloxy-1,3-imide - azolidin-2-one, 1-(5-methyl-1',3,4-thiadiazol-2-yl)-3-methyl-5-0-ethoxypropionyloxy-1,3-imidazolidin-2-one, 1- (5-methyl-1,3,4-thia-A diazol-2-yl)-3-methyl-5-propoxyacetyloxy-1,3-imidazolidin-2-one, 1-(5-methyl-1,3, 4-thiadiazol-2-yl)-3-methyl-5-butoxyacetyloxy-1,3-

, imidazolidin-2-on, 1-metyl-l,3,4-tiadiazpl-2-yl)-3-metyi-5-heksyl-oksyacetyloksy-l,3-imidazolidin-2-on, 1-(5-metyl-l,3,4-tiadiazol-2- yl)-3-metyl-5-(3,4-diklorfenylacetyloksy)-1,3-imidazolidin-2-on, 1-(5-metyl-l,3,4-tiadiazol-2-yl)-3-metyl-5-(4— trifluormetylfenyl-acetyloksy )-1,3-imidazolidin-2-on, 1-(5-metyl-l,3,4-tiadiazol-2-yl)-3-metyl-5-(2-metyl-4-klorfenylacetyloksy)-l,3-imidazolidin-2-on, 1-(5-metyl-l,3,4-tiadiazol-2-yl)-3-metyl-5-(3-metyltiofenyl-acetyloksy)-l,3-imidazolidin-?-on, 1-(5-metyl-l,3,4-tiadiazol-2-yl)-3- met<y>l-5-.(2-me<t>'Gks<y>fen<y>lacet<y>loke,y)-l, 3-imidazolidinr2-on..og liknende. , imidazolidin-2-one, 1-methyl-1,3,4-thiadiazpl-2-yl)-3-methyl-5-hexyl-oxyacetyloxy-1,3-imidazolidin-2-one, 1-(5-methyl -1,3,4-thiadiazol-2-yl)-3-methyl-5-(3,4-dichlorophenylacetyloxy)-1,3-imidazolidin-2-one, 1-(5-methyl-1,3,4 -thiadiazol-2-yl)-3-methyl-5-(4- trifluoromethylphenyl-acetyloxy )-1,3-imidazolidin-2-one, 1-(5-methyl-1,3,4-thiadiazol-2-yl )-3-methyl-5-(2-methyl-4-chlorophenylacetyloxy)-1,3-imidazolidin-2-one, 1-(5-methyl-1,3,4-thiadiazol-2-yl)-3- methyl-5-(3-methylthiophenyl-acetyloxy)-1,3-imidazolidin-?-one, 1-(5-methyl-1,3,4-thiadiazol-2-yl)-3- met<y>l- 5-.(2-me<t>'Gks<y>phen<y>lacet<y>loke,y)-1, 3-imidazolidin 2-one..and the like.

For praktir.k anvendelse som herbicider innblandes vanligvis forbindelsene ifølge oppfinnelsen i herbicide preparater spm omfatter en inert bærer og en herbicid toksisk mengde av en slik forbindelse. Slike herbicidpreparater, som også kan kalles sammen-setninger, gjør det mulig å påføre den aktive forbindelsen på hen-siktsmessig måte på det stedet der ugresset finnes i ønsket mengde. For practical use as herbicides, the compounds according to the invention are usually mixed into herbicidal preparations, eg, comprising an inert carrier and a herbicidally toxic amount of such a compound. Such herbicide preparations, which can also be called compositions, make it possible to apply the active compound in an appropriate manner at the place where the weed is found in the desired amount.

Disse preparater kan være faststoffer som f.eks. støv, granulater, eller fuktbare pulvere, eller de kan være væsker spm f.eks. løs-ninger, aerosoler eller emulgerbare konsentrater. These preparations can be solids such as e.g. dust, granules, or wettable powders, or they can be liquids, e.g. solutions, aerosols or emulsifiable concentrates.

Støv kan eksempelvis fremstilles ved å male og blande den aktive forbindelsen med en fast, inert bærer som f.eks. talk, leire, silisiumdioksyder, pyrofyllitt og liknende. Granulære sammen-setninger kan fremstilles ved å impregnere forbindelsen, vanligvis oppløst i et passende løsningsmiddel, på og inn i granulerte bærere som f.eks. attapulgittene eller vermikulittene, vanligvis med en partikkelstørrelse i området fra ca. 0,3 til 1,5 mm. Fuktbare pulvere, som kan dispergeres i vann eller olje til en hvilken som helst konsentrasjon av den aktive forbindelsen, kan fremstilles ved å innblande fuktemidler i konsentrerte støvpreparater. Dust can, for example, be produced by grinding and mixing the active compound with a solid, inert carrier such as e.g. talc, clay, silicon dioxide, pyrophyllite and the like. Granular compositions can be prepared by impregnating the compound, usually dissolved in a suitable solvent, onto and into granular carriers such as e.g. the attapulgites or vermiculites, usually with a particle size in the range from approx. 0.3 to 1.5 mm. Wettable powders, which can be dispersed in water or oil to any concentration of the active compound, can be prepared by mixing wetting agents into concentrated dust preparations.

•I noen tilfeller er de aktive forbindelsene tilstrekke-lig løselige i , vanlige organiske løsningsmidler som f.eks. kerosen eller xylen, til at de kan anvendes direkte som løsninger i disse løsningsmidlene. Løsninger av herbicider kan ofte dispergeres under •In some cases, the active compounds are sufficiently soluble in common organic solvents such as e.g. kerosene or xylene, so that they can be used directly as solutions in these solvents. Solutions of herbicides can often be dispersed below

overatmosfæriske trykk som aerosoler. Foretrukne flytende herbicidpreparater er imidlertid emulgerbare konsentrater som omfatter en above-atmospheric pressures such as aerosols. However, preferred liquid herbicide preparations are emulsifiable concentrates comprising a

aktiv forbindelse ifølge oppfinnelsen og som inert bærer et løs-ningsmiddel og et emulgeringsmiddei. Slike emulgerbare konsentrater kan fortynnes med vann og/eller olje til enhver ønsket konsentrasjon, av aktiv forbindelse for påføring som spray på ugresset. De mest brukte emulgeringsmidler i disse konsentrater er ikke-ioniske eller blandinger av ikke-ioniske og anioniske overflate-aktive midler. Med bruk av noen emulgeringsmiddelsystemer kan det fremstilles inverterte emulsjoner (vann-i-olje) for direkte på-føring på ugress-forekomster. active compound according to the invention and which inertly carries a solvent and an emulsifying agent. Such emulsifiable concentrates can be diluted with water and/or oil to any desired concentration of active compound for application as a spray to the weeds. The most commonly used emulsifiers in these concentrates are non-ionic or mixtures of non-ionic and anionic surfactants. With the use of some emulsifier systems, inverted emulsions (water-in-oil) can be produced for direct application to weed occurrences.

Et typisk herbicidpreparet ifølge oppfinnelsen illustreres ved følgende eksempel hvor mengdene er angitt som vektdeler. A typical herbicide preparation according to the invention is illustrated by the following example where the amounts are given as parts by weight.

Ekaeittpel 9Ekaeittpel 9

Fremstilling av acøv.Production of acøv.

De ovennevnte ingredienser blandes i en mekanisk malé-blandemaskin og males inntil det oppnås et homogent, frittstrøm-mende støv med ønsket partikkelstørrelse. Dette støv er egnet for direkte påføring på ugressbevokste steder. The above-mentioned ingredients are mixed in a mechanical malé mixing machine and ground until a homogeneous, free-flowing dust with the desired particle size is obtained. This dust is suitable for direct application to weedy areas.

Forbindelsene ifølge oppfinnelsen kan påføres3om herbicider på alle kjente måter på fagområdet. En metode for bekjempelse av ugress omfatter å bringe et herbicidpreparat omfattende en inert bærer og som avgjørende aktiv ingrediens i en mengde som er. toksisk overfor ugresset, en forbindelse ifølge oppfinnelsen i kontakt med ugressforekomsten. Konsentrasjonen av forbindelsene ifølge oppfinnelsen i herbicidpreparatene vil variere meget med typen av Sammensetning og det formål det er bestemt for, men vanligvis vil herbicidpreparatene omfatte fra ca. 0,05 til ca. 95 vekt% av de aktive forbindelsene ifølge oppfinnelsen. I en foretrukket utførelsesform av oppfinnelsen inneholder de herbicide pre-paratene fra ca. 5 til ca. 75 vekt% av den aktive forbindelsen.Preparatene kan også inneholde «like tilleggssubstanser som f.eks. insekticider, nematocider, fungicider og liknende, stabilisatorer, spredemidler, inaktivatorer, klebemidler, festemidler, gjødnings-stoffer, aktivatorer, synergistiske forbindelser og liknende. The compounds according to the invention can be applied as herbicides in all known ways in the field. A method for controlling weeds comprises bringing a herbicide preparation comprising an inert carrier and as the decisive active ingredient in an amount which is. toxic to the weed, a compound according to the invention in contact with the weed occurrence. The concentration of the compounds according to the invention in the herbicide preparations will vary greatly with the type of composition and the purpose for which it is intended, but usually the herbicide preparations will comprise from approx. 0.05 to approx. 95% by weight of the active compounds according to the invention. In a preferred embodiment of the invention, the herbicidal preparations contain from approx. 5 to approx. 75% by weight of the active compound. The preparations may also contain "the same additional substances as e.g. insecticides, nematocides, fungicides and the like, stabilisers, dispersants, inactivators, adhesives, fixing agents, fertilisers, activators, synergistic compounds and the like.

Forbindelsene ifølge oppfinnelsen er. også anvendbare når de kombineres med andre herbicider og/eller bladfjernere, tørke-midler,.vekstinhibitorer og liknende i de herbicidpreparater som The compounds according to the invention are. also usable when combined with other herbicides and/or leaf removers, drying agents, growth inhibitors and the like in the herbicide preparations which

er beskrevet foran. Disse andre materialer kan omfatte fra ca. 5is described above. These other materials can include from approx. 5

til ca. 95% av de aktive ingrediensene i herbicidpreparatene. Anvendelse av kombinasjoner av disse andre herbicider og/eller blad-fjerningsmidler, tørkemidler, osv. med forbindelsene ifølge.oppfinnelsen gir herbicidpreparater som er mer effektive ved bekjempelse av ugress og gir ofte resultater som ikke kan oppnås med. separate preparater av de enkelte herbicider. to approx. 95% of the active ingredients in the herbicide preparations. The use of combinations of these other herbicides and/or defoliants, desiccants, etc. with the compounds according to the invention provides herbicide preparations which are more effective in controlling weeds and often give results that cannot be achieved with. separate preparations of the individual herbicides.

Ugress er uønskede planter som vokser på uønskede steder, de har ingen økonomisk verdi og de forstyrrer produksjonen av kulturvekster, dyrkingen av prydplanter eller kan skade husdyr. Weeds are unwanted plants that grow in unwanted places, they have no economic value and they interfere with the production of crops, the cultivation of ornamental plants or can harm livestock.

Mange typer av ugress er kjent og omfatter ettårige planter som f,eks. perumelde, meldestokk, reverumpe, fingerhirse, åkersennep, engpengeurt, vanlig raigress, gåsemure, vassarv, floghavre, eng-lodnegress, portulakk, hønsehirsé, "smartweed", slirekne, krokfrø, "kochia", snegleskolm, klinte, ambrosia, dylle, "cofféeweed", kro-ton, "cuphea", sniketråd, jordrøyk, åkersvinéblom, då, vill bok-hvete, knavel, vortemelk, vanlig linbendel, "emex", "jungle rice", tjønnaks, toppgåseblomi "carpetweed", ormevindel, maure, andemat, "naiad", rugfaks, høsthirse, piggeple, vanlig kveke, "switchgra3s", Many types of weeds are known and include annual plants such as plum blossom, mullein, foxtail, finger millet, field mustard, meadowsweet, common ryegrass, gooseberry, sedge, ryegrass, meadow furrow grass, purslane, hen's millet, "smartweed", scabbard, hook seed, "kochia", snail columbine, ragweed, ragweed, " cofféeweed", kro-ton, "cuphea", creeping thread, earth smoke, field vine flower, doe, wild beech wheat, knavel, wart milk, common lindendel, "emex", "jungle rice", tjønkax, top goose flower "carpetweed", wormwood, ants , duck food, "naiad", rye fax, autumn millet, prickly pear, common quack, "switchgra3s",

"watergrass", "teaweed", vill turnips og "3prangletop", toårige planter som f.eks. villgulrot, "matricaria", villbygg, hanekam, gåseblom, borre, kongslys, rundbladet kattOBt, veitistel, hunde-tunge, møllkongslys og fiolett tistelknoppurt eller flerårige som f.eks. hvit klinte, flerårig raigress, kveke, "Johnsongrass" (en durra-art), åkertistel, strandvindel, Bermudagrass, småsyre, krøl-let syre, kypergress, storarve, løvetann, blåklokke, åkervindel, russisk knoppurt, "mesquite", torskemunn, vanlig ryllik, asters, steihfrø, snelle, "ironweed", "sesbania", sivaks, dunkjevle, vin-terkarse, søtvier, "riutsedge", "milkweed" og skrinrieblom. "watergrass", "teaweed", wild turnips and "3prangletop", biennial plants such as wild carrot, "matricaria", wild barley, cock's comb, goose flower, burdock, king's wort, round-leaved cat's OBt, road thistle, dog's tongue, moth king's wort and violet thistle bud herb or perennials such as e.g. white sedge, perennial ryegrass, vetch, "Johnsongrass" (a species of sorghum), field thistle, sedge, Bermudagrass, sorrel, curled sorrel, cypress, sedge, dandelion, bluebell, field sedge, Russian knotweed, "mesquite", cod's mouth, common yarrow, asters, sedge, sedge, "ironweed", "sesbania", sivax, dunkjevle, winecress, sweet willows, "riutsedge", "milkweed" and skrinrieblom.

'■ Slike ugress kan klassifiseres som bredbladede eller gress-aktige ugress.' Det er økonomisk ønskelig å bekjempe veksten av slike ugress uten å skade nytteplanter eller husdyr. '■ Such weeds may be classified as broad-leaved or grass-like weeds.' It is economically desirable to combat the growth of such weeds without harming useful plants or livestock.

Forbindelsene ifølge oppfinnelsen er spesielt verdifulle ved ugressbekjempelse fordi de er toksiske overfor mange arter og grupper av ugress, mens de er relativt ikke-toksiske overfor mange nyttevekster. Den nøyaktige mengde av forbindelsen som behøves vil avhenge av mange faktorer, innbefattet de spesielle ugressarters motstandskraft, været, jordtypen, påføringsmetoden, arten av nyttevekster i samme område og liknende. Mens således påføring av opp til bare 11 eller 22 gram aktiv forbindelse pr. ar kan være tilstrekke-lig for effektiv bekjempelse av små forekomster av ugress som vokser under ugunstige betingelser, kan det kreves påføring av 112 g pr. ar eller mer av aktiv forbindelse for effektiv bekjempelse av store forekomster, av hardføre flerårige ugress som vokser .under fordel-aktige betingelser. The compounds according to the invention are particularly valuable in weed control because they are toxic to many species and groups of weeds, while they are relatively non-toxic to many useful crops. The exact amount of compound needed will depend on many factors, including the resistance of the particular weed species, the weather, the type of soil, the method of application, the nature of the crops in the same area and the like. While thus applying up to only 11 or 22 grams of active compound per ar may be sufficient for effective control of small instances of weeds growing under unfavorable conditions, an application of 112 g per years or more of active compound for effective control of large deposits of hardy perennial weeds growing under favorable conditions.

Den herbicide toksisiteten for forbindelsen ifølge oppfinnelsen kan illustreres ved hjelp av mange av de etablerte test-eteknikker innen fagområdet, som f.eks. før- og etterspirings-testing. The herbicidal toxicity of the compound according to the invention can be illustrated using many of the established test techniques in the field, such as e.g. pre- and post-germination testing.

Den herbicide aktiviteten for forbindelsen ifølge oppfinnelsen ble demonstrert ved forsøk som ble utført for før-spir-irigskontroll av forskjellige ugress. I disse forsøk ble det sådd forskjellige ugressfrø i små plastpotter fylt med tørr jord, 24 timer senere eller mindre ble pottene vannet inntil jorden var våt og testforbindelsen i form av en vandig emulsjon av en acetonløs-ning inneholdende emulgeriirgsmidler blt= sprøytet på jordoverflaten i de angitte konsentrasjoner. The herbicidal activity of the compound according to the invention was demonstrated in experiments carried out for pre-emergence control of various weeds. In these experiments, various weed seeds were sown in small plastic pots filled with dry soil, 24 hours later or less the pots were watered until the soil was wet and the test compound in the form of an aqueous emulsion of an acetone solution containing emulsifiers blt= sprayed on the soil surface in the specified concentrations.

Etter sprøyting ble•jordbeholderne plassert i drivhus og tilført varme etter behov og vannet daglig eller oftere. Plantene ble holdt under disse betingelser i 15 til 21 dager, , på hvilket tidspunkt plantenes tilstand og graden av skade på plantene ble be-dømt etter' en.skala fra0til 10 som følgers 0 = ingen skade, After spraying, the soil containers were placed in a greenhouse and heated as needed and watered daily or more often. The plants were kept under these conditions for 15 to 21 days, at which time the condition of the plants and the degree of damage to the plants were assessed according to a scale from 0 to 10 as follows 0 = no damage,

1,2 - svak skade, 3,4 = moderat skade, 5,6 = moderat.alvorlig skade, 7,8,9 alvorlig skade, lo = død. Effektiviteten av forbindelsene fremgår av følgende datas 1,2 - slight damage, 3,4 = moderate damage, 5,6 = moderate.severe damage, 7,8,9 severe damage, lo = death. The effectiveness of the connections can be seen from the following data

pen herbicide, aktiviteten for forbindelsene ifølge oppfinnelsen ble også påvist ved forsøk som ble utført for etter-spiringsbekjempelse av forskjellige ugressarter. i disse forsøk ble testforbindelsen innblandet i en vandig emulsjon og sprøytet på ugressets blader i angitt dose når bladene hadde nådd en fore-skrevet størrelse. Etter sprøytingen ble plantene plassert i drivhus bg vannet daglig eller oftere. Vann ble ikke påført på bladene til de behandlede plantene. Skade<g>raden ble bestemt 10 til 15 dager etter behandlingen og ble bedømt etter en .skala fra 0 til 10 som beskrevet foran. Effektiviteten for forbindelsene fremgår av følgende data: pen herbicide, the activity of the compounds according to the invention was also demonstrated in experiments carried out for post-emergence control of various weed species. in these trials, the test compound was mixed into an aqueous emulsion and sprayed onto the weed's leaves in a specified dose when the leaves had reached a prescribed size. After spraying, the plants were placed in greenhouses and watered daily or more often. Water was not applied to the leaves of the treated plants. The extent of damage was determined 10 to 15 days after treatment and was scored on a scale from 0 to 10 as described above. The efficiency of the connections is evident from the following data:

Claims

1. Herbicidal thiadiazolyl-acylimidazolidinones, characterized in that they have the general formula:

where R is alkyl, cycloalkyl, alkenyl, haloalkyl, alkoxy, alkylthio, alkylsulfonyl or alkylsulfinyl, R <2> is alkyl, alkenyl, haloalkyl or:

4 5 3 where R and R are hydrogen or alkyl and R is alkyl, alkenyl, haloalkyl, alkynyl, alkoxyalkyl, cycloalkyl otherwise

where X is alkyl, alkoxy, halogen, haloalkyl, alkylthio, nitro or cyano, n is an integer from 0 to 3 and m is 0 or 1.

2. Herbicidal compounds according to claim 1, characterized in that they have the general formula

where R* is alkyl with up to 3 carbon atoms, cycloalkyl, alkenyl, chloroalkyl, bromoalkyl, alkoxy, alkylthio, alkylsulfonyl or alkyl-2 sulfmyl, R is alkyl, alkenyl, haloalkyl otherwise

3. Herbicidal compounds, characterized in that they have the general formula

1 2 where R is butyl, pentyl, hexyl or trifluoromethyl, R is alkyl, alkenyl, haloalkyl otherwise

4 5 3 where R and R are hydrogen or alkyl and R is alkyl, alkenyl, haloalkyl, alkynyl, alkoxyalkyl, cycloalkyl or:

where X is alkyl, alkoxy, halogen, haloalkyl, alkylthio, nitro or cyano, n is an integer from 0 to 3 and m is 0 or 1, provided that R 2 is haloalkyl or contains at least 2 carbon atoms , 3 , when R is methyl.

4. Compound according to claim 1, characterized in that it is 1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-ethyl-5-acetyloxy-1,3-imidazolidin-2- Wed.

5. Compound according to claim 1, characterized in that it is 1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-5-acetyloxy-1,3-imidazolidin-2-one.

6. Process for the production of herbicidal thiadiazolylacylimidazolidinones with the formula specified in claim 1, characterized in that a compound with the general formula:

12 where R dg R is as stated in claim 1, is reacted with an acid anhydride with the formula?

or with an acid halide of the formula

3 where R is as stated in claim 1.

7. Method according to claim 6, characterized in that the first-mentioned compound is reacted with the described acid anhydride in the presence of a catalytic amount of p-toluenesulfonic acid.

8. Process according to claim 6, characterized in that the first-mentioned compound is reacted with the described acid halide in the presence of an acid acceptor.

9. Method according to claim 8, characterized in that a tertiary amine is used as acid acceptor.