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Abstract
The invention relates to 2-imidazolin-5-one or 2-imidazoline-5-thione derivatives of general formula (I) <IMAGE> in which, - W is a sulphur or oxygen atom or the S=O group, - A represents O or S - n = 0 or 1 - B represents NR5 or O or S or CR5R6 or SO2 or C=O - R1 to R4 represent a hydrogen atom or a hydrocarbon radical, optionally substituted, especially by halogen atoms. The invention also relates to the preparation of these compounds and to their use as broad-spectrum fungicides.
Claims (28)
1 Patentni zahtevki 1. Spojine z imidazolinon ali imidazolintion skupino, označene s tem, da ustrezajo splošni formuli (I)Claims with imidazolinone or imidazolintion group, characterized in that they correspond to general formula (I)(I) W kjer je - W atom žvepla ali kisika ali skupina S=0 - A predstavlja O ali S - n = 0 ali 1 - B predstavlja NR5 ali O ali S ali CR5R6 ali S02 ali C=0. - Ri in R2, ki sta enaka ali različna, predstavljata: - H, pod pogojem, daje ena od dveh skupin različna od H, ali - alkilni ali haloalkilni radikal z 1 do 6 atomi ogljika ali - alkoksialkilni, alkiltioalkilni, alkilsulfonilalkilni, monoalkilaminoalkilni, alkenilni ali alkinilni radikal z 2 do 6 atomi ogljika ali - dialkilaminoalkilni radikal ali cikloalkilni radikal z 3 do 7 atomi ogljika ali - arilni radikal, prednostno fenil, naftil, tienil, furil, piridil, benzotienil, benzofuril, kinolil, izokinolil ali metilendioksifenil, eventualno substituiran z 1 do 3 skupinami, izbranimi izmed R7, ali - arilalkilni, ariloksialkilni, ariltioalkilni ali arilsulfonilalkilni radikal, ali - R! in R2 lahko tvorita z ogljikom, na katerega sta vezana na obroču, karbocikel ali heterocikel s 5 do 7 atomi, pri čemer pa je mogoče, da so ti obroči kondenzirani na fenil, eventualno substituiran z 1 do 3 skupinami, izbranimi izmed R7; - R3 predstavlja - alkilno skupino z 1 do 6 atomi ogljika ali 2 - alkoksialkilno, alkiltioalkilno, alkilsulfonilalkilno, haloalkilno, cianoalkilno, tiocianatoalkilno, oksoalkilno, alkenilno ali alkinilno skupino z 2 do 6 atomi ogljika ali - dialkilaminoalkilno, alkoksikarbonilalkilno ali N-alkilkarbamoilalkilno skupino s 3 do 6 atomi ogljika ali - Ν,Ν-dialkilkarbamoilalkilno skupino s 4 do 8 atomi ogljika ali - arilalkilno skupino, pri čemer je alkilni del radikal z 1 do 6 atomi ogljika in je arilni del fenil, naftil, tienil, furil ali piridil, eventualno substituiran z 1 do 3 skupinami, izbranimi izmed R7; - R4 predstavlja: - atom vodika, kadar je n enak 1, ali - alkilno skupino z 1 do 6 atomi ogljika ali - alkoksialkilno, alkiltioalkilno, haloalkilno, cianoalkilno, tiocianatoalkilno, alkenilno ali alkinilno skupino z 2 do 6 atomi ogljika ali - dialkilaminoalkilno, alkoksikarbonilalkilno ali N-alkilkarbamoilalkilno skupino s 3 do 6 atomi ogljika ali - Ν,Ν-dialkilkarbamoilalkilno skupino s 4 do 8 atomi ogljika ali - arilni radikal, prednostno fenil, naftil, tienil, furil, piridil, pirimidil, piridazinil, pirazinil, benzotienil, benzofuril, kinolil, izokinolil ali metilendioksifenil, eventualno substituiran z 1 do 3 skupinami, izbranimi izmed R7 ali - arilalkilni, ariloksialkilni, ariltioalkilni ali arilsulfonilalkilni radikal ali - amino skupino, disubstituirano z dvema enakima ali različnima skupinama, izbranima izmed: - alkilnega radikala z 1 do 6 atomi ogljika - alkoksialkilnega, alkenilnega ali alkinilnega radikala s 3 do 6 atomi ogljika - cikloalkilnega radikala s 3 do 7 atomi ogljika - arilalkilnega, fenilnega ali naftilnega radikala, eventualno substituiranega z 1 do 3 skupinami, izbranimi izmed R7, ali - tienilmetilnega ali furfurilnega radikala 3 - pirolidino, piperidino, morfolino ali piperazino skupino, eventualno substituirano z alkilom z 1 do 3 atomi ogljika; - R5 predstavlja: - H, razen kadar je R* H, ali - alkilni, haloalkilni, alkilsulfonilni ali haloalkilsulfonilni radikal z 1 do 6 atomi ogljika ali - alkoksialkilni, alkiltioalkilni, acilni, alkenilni, alkinilni, haloacilni, alkoksikarbonilni, haloalkoksikarbonilni, alkoksialkilsulfonilni ali cianoalkilsulfonilni radikal z 2 do 6 atomi ogljika ali - alkoksialkoksikarbonilni, alkiltioalkoksikarbonilni ali cianoalkoksikarbonilni radikal s 3 do 6 atomi ogljika ali - formilni radikal ali - cikloalkilni, alkoksiacilni, alkiltioacilni, cianoacilni, alkenilkarbonilni ali alkinilkarbonilni radikal s 3 do 6 atomi ogljika ali - cikloalkilkarbonilni radikal s 4 do 8 atomi ogljika ali - fenil; arilalkilkarbonil, prednostno fenilacetil in fenilpropionil; arilkarbonil, prednostno benzoil, eventualno substituiran z 1 do 3 skupinami izmed R7; tienilkarbonil; furilkarbonil; piridilkarbonil; benziloksikarbonil; furfuriloksikarbonil; tetrahidrofurfuriloksikarbonil; tienilmetoksikarbonil; piridilmetoksikarbonil; fenoksikarbonil ali (feniltio)karbonil, pri čemer je fenil sam eventualno substituiran z 1 do 3 skupinami izmed R7; (alkiltio)karbonil; (haloalkiltio)karbonil; (alkoksialkiltio)karbonil; (cianoalkiltio)karbonil; (benziltio)karbonil; (furfuriltio)karbonil; (tetrahidrofurfuriltio)karbonil; (tienilmetiltio)-karbonil; (piridilmetiltio)karbonil; ali arilsulfonilni radikal ali - karbamoilni radikal, eventualno mono- ali disubstituiran z - alkilno ali haloalkilno skupino z 1 do 6 atomi ogljika ali - cikloalkilno, alkenilno ali alkinilno skupino s 3 do 6 atomi ogljika ali - alkoksialkilno, alkiltioalkilno ali cianoalkilno skupino z 2 do 6 atomi ogljika ali - fenilom, eventualno substituiranim z 1 do 3 R7 skupinami; - sulfamoilno skupino, eventualno mono- ali disubstituirano z 4 - alkilno ali haloalkilno skupino z 1 do 6 atomi ogljika ali - cikloalkilno, alkenilno ali alkinilno skupino s 3 do 6 atomi ogljika ali - alkoksialkilno, alkiltioalkilno ali cianoalkilno skupino z 2 do 6 atomi ogljika ali - fenilom, eventualno substituiranim z 1 do 3 R7 skupinami; - alkiltioalkilsulfonilno skupino s 3 do 8 atomi ogljika ali cikloalkilsulfonilno skupino s 3 do 7 atomi ogljika; - R<5 predstavlja: - atom vodika ali - ciano skupino ali - alkilno skupino z 1 do 6 atomi ogljika ali cikloalkilno skupino s 3 do 7 atomi ogljika ali - acilno ali alkoksikarbonilno skupino z 2 do 6 atomi ogljika ali - benzoilno skupino, eventualno substituirano z 1 do 3 R7 skupinami; - R7 predstavlja: - atom halogena ali - alkilni, haloalkilni, alkoksi, haloalkoksi, alkiltio, haloalkiltio ali alkilsulfonilni radikal z 1 do 6 atomi ogljika ali - cikloalkilni, halocikloalkilni, alkeniloksi, alkiniloksi, alkeniltio ali alkiniltio radikal s 3 do 6 atomi ogljika ali - nitro ali ciano skupino ali - amino radikal, eventualno mono- ali disubstituiran z alkilnim ali acilnim radikalom z 1 do 6 atomi ogljika ali alkoksikarbonilnim radikalom z 2 do 6 atomi ogljika - fenilni, fenoksi ali piridiloksi radikal, pri čemer so ti radikali eventualno substituirani; in njihove soli, z izjemo spojin, za katere, kadar sta Ri in R2 istočasno fenil ali istočasno metil, je B CR5R6, A je žveplo in W je O ali S; z izjemo treh spojin z Ri = vodik, n = 1, B = NR5, z R5 in R4 = metil, AR3 = SCH3, W = O in pri čemer je R2 bodisi vodik, metil ali fenil; 5 tudi z izjemo spojine, v kateri je R) fenil, R2, R3 in R4 so metil, nje enak ničla, A in W sta oba atoma žvepla.(I) W wherein - W is a sulfur or oxygen atom or the group S = 0 - A represents O or S - n = 0 or 1 - B represents NR5 or O or S or CR5R6 or SO2 or C = 0. - R 1 and R 2, which are the same or different, represent: - H, provided that one of the two groups is other than H, or - an alkyl or haloalkyl radical having 1 to 6 carbon atoms, or - alkoxyalkyl, alkylthioalkyl, alkylsulfonylalkyl, monoalkylaminoalkyl, alkenyl or alkynyl radical having 2 to 6 carbon atoms or - dialkylaminoalkyl radical or cycloalkyl radical having 3 to 7 carbon atoms or - aryl radical, preferably phenyl, naphthyl, thienyl, furyl, pyridyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl or methylenedio substituted with 1 to 3 groups selected from R7, or - an arylalkyl, aryloxyalkyl, arylthioalkyl or arylsulfonylalkyl radical, or - R1. and R 2 may be formed by the carbon to which they are attached on the ring, a carbocycle or a heterocycle of 5 to 7 atoms, it being possible for these rings to be fused to phenyl optionally substituted by 1 to 3 groups selected from R 7; - R3 represents - an alkyl group with 1 to 6 carbon atoms or 2 - alkoxyalkyl, alkylthioalkyl, alkylsulfonylalkyl, haloalkyl, cyanoalkyl, thiocyanatoalkyl, oxoalkyl, alkenyl or alkynyl group with 2 to 6 carbon atoms or - dialkylaminoalkylalkylalkylalkyl 3 to 6 carbon atoms or a - N, N-dialkylcarbamoylalkyl group having 4 to 8 carbon atoms or - an arylalkyl group, the alkyl moiety being a radical having 1 to 6 carbon atoms and the aryl moiety being phenyl, naphthyl, thienyl, furyl or pyridyl, optionally substituted with 1 to 3 groups selected from R7; - R 4 represents: - a hydrogen atom when n is 1, or - an alkyl group having 1 to 6 carbon atoms, or - an alkoxyalkyl, alkylthioalkyl, haloalkyl, cyanoalkyl, thiocyanatoalkyl, alkenyl or alkynyl group having 2 to 6 carbon atoms, or - dialkylaminoalkyl, alkoxycarbonylalkyl or N-alkylcarbamoylalkyl group having 3 to 6 carbon atoms or - N, N-dialkylcarbamoylalkyl group having 4 to 8 carbon atoms or - aryl radical, preferably phenyl, naphthyl, thienyl, furyl, pyridyl, pyrimidyl, pyridine benzofuryl, quinolyl, isoquinolyl or methylenedioxyphenyl optionally substituted with 1 to 3 groups selected from R7 or - an arylalkyl, aryloxyalkyl, arylthioalkyl or arylsulfonylalkyl radical or - an amino group disubstituted by two identical or different groups; up to 6 carbon atoms - alkoxyalkyl, alkenyl or alkynyl radical with 3 to 6 carbon atoms - cycloalkyl radical with 3 to 7 carbon atoms - an arylalkyl, phenyl or naphthyl radical optionally substituted by 1 to 3 groups selected from R7, or - a thienylmethyl or furfuryl radical 3 - a pyrrolidino, piperidino, morpholino or piperazine group optionally substituted by alkyl having 1 to 3 carbon atoms; - R5 represents: - H, except when R * H, or - an alkyl, haloalkyl, alkylsulfonyl or haloalkylsulfonyl radical having 1 to 6 carbon atoms, or - alkoxyalkyl, alkylthioalkyl, acyl, alkenyl, alkynyl, haloacyl, alkoxycarbonyl, haloalkoxycarbonyl cyanoalkylsulfonyl radical having 2 to 6 carbon atoms or - alkoxyalkyloxycarbonyl, alkylthioalkoxycarbonyl or cyanoalkoxycarbonyl radical having 3 to 6 carbon atoms or - formyl radical or - cycloalkyl, alkoxyacyl, alkylthioacyl, cyanoalkylcarbonyl, alkenyl with 4 to 8 carbon atoms or - phenyl; arylalkylcarbonyl, preferably phenylacetyl and phenylpropionyl; arylcarbonyl, preferably benzoyl, optionally substituted with 1 to 3 groups from R7; thienylcarbonyl; furylcarbonyl; pyridylcarbonyl; benzyloxycarbonyl; furfuryloxycarbonyl; tetrahydrofurfuryloxycarbonyl; thienylmethoxycarbonyl; pyridylmethoxycarbonyl; phenoxycarbonyl or (phenylthio) carbonyl, wherein the phenyl itself is optionally substituted with 1 to 3 groups from R7; (alkylthio) carbonyl; (haloalkylthio) carbonyl; (alkoxyalkylthio) carbonyl; (cyanoalkylthio) carbonyl; (benzylthio) carbonyl; (furfurylthio) carbonyl; (tetrahydrofurfurylthio) carbonyl; (thienylmethylthio) -carbonyl; (pyridylmethylthio) carbonyl; or an arylsulfonyl radical or - a carbamoyl radical optionally mono- or disubstituted by - an alkyl or haloalkyl group of 1 to 6 carbon atoms or - a cycloalkyl, alkenyl or alkynyl group of 3 to 6 carbon atoms or - an alkoxyalkyl, alkylthioalkyl or cyanoalkyl group of 2 to 6 6 carbon atoms or - phenyl optionally substituted with 1 to 3 R7 groups; - a sulfamoyl group optionally mono- or disubstituted by a 4-alkyl or haloalkyl group having 1 to 6 carbon atoms, or - a cycloalkyl, alkenyl or alkynyl group having 3 to 6 carbon atoms, or - an alkoxyalkyl, alkylthioalkyl or cyanoalkyl group having 2 to 6 carbon atoms or - phenyl optionally substituted with 1 to 3 R7 groups; - an alkylthioalkylsulfonyl group having 3 to 8 carbon atoms or a cycloalkylsulfonyl group having 3 to 7 carbon atoms; - R < 5 represents: - a hydrogen atom or - a cyano group or - an alkyl group with 1 to 6 carbon atoms or a cycloalkyl group with 3 to 7 carbon atoms or - an acyl or alkoxycarbonyl group with 2 to 6 carbon atoms or - a benzoyl group, optionally substituted with 1 to 3 R7 groups; - R7 represents: - a halogen atom, or - an alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio or alkylsulfonyl radical having 1 to 6 carbon atoms, or - a cycloalkyl, halocycloalkyl, alkenyloxy, alkynyloxy, alkenylthio or alkynyl alkyl radical with 3 to - a nitro or cyano group, or - an amino radical optionally mono- or disubstituted by an alkyl or acyl radical having 1 to 6 carbon atoms or an alkoxycarbonyl radical having 2 to 6 carbon atoms - a phenyl, phenoxy or pyridyloxy radical, these radicals being optionally substituted ; and their salts, with the exception of compounds wherein, when R1 and R2 are simultaneously phenyl or simultaneously methyl, B is CR5R6, A is sulfur and W is O or S; with the exception of three compounds with R 1 = hydrogen, n = 1, B = NR 5, with R 5 and R 4 = methyl, AR 3 = SCH 3, W = O and wherein R 2 is either hydrogen, methyl or phenyl; 5 also with the exception of a compound in which R 1 is phenyl, R 2, R 3 and R 4 are methyl, n is zero, A and W are both sulfur atoms.2. Spojine po zahtevku 1, označene s tem, da je A atom žvepla.Compounds according to Claim 1, characterized in that A is a sulfur atom.3. Spojine po zahtevku 1, označene s tem, daje W atom kisika.Compounds according to Claim 1, characterized in that W is an oxygen atom.4. Spojine po zahtevku 2, označene s tem, da ustrezajo splošni formuliCompounds according to Claim 2, characterized in that they correspond to the general formulala kjer imajo W, n in Rj do R$ enak pomen kot v zahtevku 1.1a wherein W, n and R 1 to R 8 have the same meaning as in claim 1.5. Spojine po zahtevku 2, označene s tem, da ustrezajo splošni formuliCompounds according to Claim 2, characterized in that they correspond to the general formula5 Ib kjer imajo W ter Rj do R5 enak pomen kot v zahtevku 1.Ib where W and R 1 to R 5 have the same meaning as in claim 1.6. Spojine po zahtevku 2, označene s tem, da ustrezajo splošni formuliCompounds according to Claim 2, characterized in that they correspond to the general formulaIc kjer imajo B, n in Ri do R4 enak pomen kot v zahtevku 1. 6Ic wherein B, n and R 1 to R 4 have the same meaning as in claim 1. 67. Spojine po zahtevku 2, označene s tem, da ustrezajo splošni formuliCompounds according to Claim 2, characterized in that they correspond to the general formulav kateri imajo B, n in do R4 enak pomen kot v zahtevku 1.in which B, n and up to R4 have the same meaning as in claim 1.8. Spojine po enem od zahtevkov 1 do 7, označene s tem, da je R5 atom vodika.Compounds according to one of Claims 1 to 7, characterized in that R 5 is a hydrogen atom.9. Spojine po zahtevku 5, označene s tem, daje R5 atom vodika (spojina Ib').Compounds according to Claim 5, characterized in that R 5 is a hydrogen atom (compound Ib ').10. Spojine po enem od zahtevkov 1 do 9, označene s tem, da R! in R2 nista atoma vodika.Compounds according to one of Claims 1 to 9, characterized in that R 1. and R2 are not hydrogen atoms.11. Spojine po enem od zahtevkov 1 do 10, označene s tem, daje R2 alkilna skupina z 1 do 3 atomi ogljika.Compounds according to one of Claims 1 to 10, characterized in that R 2 is an alkyl group having 1 to 3 carbon atoms.12. Spojine po enem od zahtevkov 1 do 11, označene s tem, daje Ri fenil, eventualno substituiran s skupino R7.Compounds according to one of Claims 1 to 11, characterized in that R 1 is phenyl optionally substituted by an R 7 group.13. Spojine po enem od zahtevkov 1 do 12, označene s tem, daje R3 alkilna skupina z 1 do 3 atomi ogljika.Compounds according to one of Claims 1 to 12, characterized in that R 3 is an alkyl group having 1 to 3 carbon atoms.14. Spojine po enem od zahtevkov 1 do 13, označene s tem, daje R4 fenil, eventualno substituiran s skupino R7.Compounds according to one of Claims 1 to 13, characterized in that R 4 is phenyl, optionally substituted by an R 7 group.15. Spojine po enem od zahtevkov 1 do 14, označene s tem, daje R3 metilni radikal.Compounds according to one of Claims 1 to 14, characterized in that R 3 is a methyl radical.16. Postopek (postopek A) za pripravo spojin s formulo (I) po zahtevku 2, označen s tem, da izvedemo S-alkilacijo 2-tiohidantoinov s formulo (II) s spojino s formulo R3X v prisotnosti baze in topila v skladu s shemo: 7 7Process (process A) for the preparation of compounds of formula (I) according to Claim 2, characterized in that the S-alkylation of 2-thiohydantoins of formula (II) is carried out with a compound of formula R3X in the presence of a base and a solvent according to the scheme : 7 7+ RiX (Π) (I) baza --► topilo kjer imajo Ri, R2, R3, R*, B in W pomen v zahtevku 1 in je X atom klora, broma ali joda ali sulfatna skupina ali alkilsulfoniloksi ali arilsulfoniloksi skupina.+ RiX (Π) (I) base --► solvent wherein R 1, R 2, R 3, R *, B and W have the meaning in claim 1 and X is a chlorine, bromine or iodine atom or a sulphate group or an alkylsulfonyloxy or arylsulfonyloxy group.17. Postopek za pripravo 2-metiltio-2-imidazolin-5-onskih spojin s formulo (Ic) (postopek B) po zahtevku 6, označen s tem, da spojino s formulo (V) cikliziramo s preprostim segrevanjem v aromatskem topilu pri refluksu po shemi: R R 2'X*=C' r .C-NH θ' .sch3 sch3 —(B)n (V) -R4Process for the preparation of 2-methylthio-2-imidazolin-5-one compounds of formula (Ic) (method B) according to Claim 6, characterized in that the compound of formula (V) is cyclized by simple heating in an aromatic solvent at reflux according to the scheme: RR 2'X * = C 'r .C-NH θ' .sch3 sch3 - (B) n (V) -R4kjer imajo Ri, R2, R4, B in n enak pomen kot v zahtevku 1.wherein R 1, R 2, R 4, B and n have the same meaning as in claim 1.18. Postopek za pripravo spojin s formulo (Ib) (postopek Cl) po shemi:A process for the preparation of compounds of formula (Ib) (process Cl) according to the scheme:označen s tem, da v topilu v prisotnosti baze spojino s formulo R5X presnovimo s spojino s formulo (Ib) po zahtevku 5, kjer je skupina R5 atom vodika po zahtevku 9 (spojina (Ib1)), skupine Ri do R4 imajo pomen, naveden v zahtevku 1, skupina R5 je alkilna, alkoksikarbonilna, acilna, aroilna, alkilsulfonilna, arilsulfonilna, karbamoilna ali sulfamoilna skupina in X predstavlja odhodno skupino, prednostno halogen, sulfatno skupino, eventualno substituiran fenoksi, R50, kjer je R5 acil, ali alkilsulfoniloksi ali arilsulfoniloksi skupino ali neodhodno skupino, prednostno izocianat ali izotiocianat. 8characterized in that in the solvent in the presence of a base the compound of formula R5X is reacted with a compound of formula (Ib) according to claim 5, wherein the group R 5 is a hydrogen atom according to claim 9 (compound (Ib1)), the groups R 1 to R 4 have the meaning given in claim 1, the group R5 is an alkyl, alkoxycarbonyl, acyl, aroyl, alkylsulfonyl, arylsulfonyl, carbamoyl or sulfamoyl group and X represents a leaving group, preferably halogen, a sulfate group, optionally substituted phenoxy, R50 wherein R5 is acyl, or alkylsulfonyloxy or arylsulfonyloxy or a group or a non-leaving group, preferably an isocyanate or an isothiocyanate. 819. Postopek za pripravo spojin s formulo (Id) (postopek C2) po shemi:19. A process for the preparation of compounds of formula (Id) (process C2) according to the scheme:označen s tem, da spojino s formulo (Id) po zahtevku 7, kjer je R2 atom vodika (spojina (Id')), presnovimo s spojino s formulo R2X v topilu in v prisotnosti baze pri temperaturi med -30 °C in +80 °C, pri čemer je X atom klora, broma ali joda in imajo Ri do R4, B in n enak pomen kot v zahtevku 1.characterized in that the compound of formula (Id) according to claim 7, wherein R 2 is a hydrogen atom (compound (Id ')) is reacted with a compound of formula R 2X in a solvent and in the presence of a base at a temperature between -30 ° C and +80 ° C, wherein X is a chlorine, bromine or iodine atom and R 1 to R 4, B and n have the same meaning as in claim 1.20. Postopek po zahtevku 19, označen s tem, da bazo izberemo iz skupine, ki obsega alkoksid, kovinski hidrid ali amid, in topilo izberemo iz skupine, ki obsega etre, ciklične etre, dimetilformamid, dimetil sulfoksid in aromatska topila.The process of claim 19, wherein the base is selected from the group consisting of alkoxide, metal hydride or amide, and the solvent is selected from the group consisting of ethers, cyclic ethers, dimethylformamide, dimethyl sulfoxide, and aromatic solvents.21. Postopek za pripravo spojin s formulo (I) (postopek D) po zahtevku 1, kjer W predstavlja skupino S=0, označen s tem, da izvedemo S-oksidacijo spojine s formulo (I), kjer je W atom žvepla, pri čemer to oksidacijo 2-imidazolin-5-tionov izvedemo s stehiometrično količino peroksidov v topilu pri temperaturi med -20 °C in +20 °C.A process for the preparation of compounds of formula (I) (process D) according to claim 1, wherein W represents a group S = 0, characterized in that the S-oxidation of the compound of formula (I), wherein W is a sulfur atom, is carried out at wherein this oxidation of 2-imidazoline-5-thiones is carried out with a stoichiometric amount of peroxides in a solvent at a temperature between -20 ° C and +20 ° C.22. Postopek po zahtevku 21, označen s tem, da je peroksid perkislina in topilo izberemo iz skupine, ki obsega kloroform in metilenklorid.Process according to Claim 21, characterized in that the peroxide is a peracid and the solvent is selected from the group consisting of chloroform and methylene chloride.23. Fungicidni sestavki, označeni s tem, da obsegajo v kombinaciji z enim ali več trdnimi ali tekočimi nosilci, ki so agrikulturno sprejemljivi, in/ali površinsko aktivnimi sredstvi, ki so tudi agrikulturno sprejemljiva, enega (ali več) aktivnih materialov, ki je/so spojina s formulo I: (I) 923. Fungicidal compositions, characterized in that they comprise, in combination with one or more solid or liquid carriers which are agriculturally acceptable and / or surfactants which are also agriculturally acceptable, one (or more) active materials which is is a compound of formula I:kjer je - W atom žvepla ali kisika ali skupina S=0 - A predstavlja O ali S - n = 0 ali 1 - B predstavlja NR5 ali O ali S ali CR^ ali S02 ali C=0. - Ri in R2, ki sta enaka ali različna, predstavljata - H, pod pogojem, daje ena od dveh skupin različna od H, ali - alkilni ali haloalkilni radikal z 1 do 6 atomi ogljika ali - alkoksialkilni, alkiltioalkilni, alkilsulfonilalkilni, monoalkilaminoalkilni, alkenilni ali alkinilni radikal z 2 do 6 atomi ogljika ali - dialkilaminoalkilni ali cikloalkilni radikal s 3 do 7 atomi ogljika ali - arilni radikal, prednostno fenil, naftil, tienil, furil, piridil, benzotienil, benzofuril, kinolil, izokinolil, ali metilendioksifenil, eventualno substituiran z 1 do 3 skupinami, izbranimi izmed R7 ali - arilalkilni, ariloksialkilni, ariltioalkilni ali arilsulfonilalkilni radikal, ali - Ri in R2 lahko tvorita z ogljikom, na katerega sta vezana na obroču, karbocikel ali heterocikel s 5 do 7 atomi, pri čemer je za te obroče mogoče, da so kondenzirani na fenil, eventualno substituiran z 1 do 3 skupinami, izbranimi izmed R7; - R3 predstavlja - alkilno skupino z 1 do 6 atomi ogljika ali - alkoksialkilno, alkiltioalkilno, alkilsulfonilalkilno, haloalkilno, cianoalkilno, tiocianatoalkilno, oksoalkilno, alkenilno ali alkinilno skupino z 2 do 6 atomi ogljika ali - dialkilaminoalkilno, alkoksikarbonilalkilno ali N-alkilkarbamoilalkilno skupino s 3 do 6 atomi ogljika ali - Ν,Ν-dialkilkarbamoilalkilno skupino s 4 do 8 atomi ogljika ali 10 - arilalkilno skupino, pri čemer je alkilni del radikal z 1 do 6 atomi ogljika in je arilni del fenil, naftil, tienil, furil ali piridil, eventualno substituiran z 1 do 3 skupinami, izbranimi izmed R7; - R4 predstavlja - atom vodika, kadar je n enako 1, ali - alkilno skupino z 1 do 6 atomi ogljika ali - alkoksialkilno, alkiltioalkilno, haloalkilno, cianoalkilno, tiocianatoalkilno, alkenilno ali alkinilno skupino z 2 do 6 atomi ogljika ali - dialkilaminoalkilno, alkoksikarbonilalkilno ali N-alkilkarbamoilalkilno skupino s 3 do 6 atomi ogljika ali - Ν,Ν-dialkilkarbamoilalkilno skupino s 4 do 8 atomi ogljika ali - arilni radikal, prednostno fenil, naftil, tienil, furil, piridil, pirimidil, piridazinil, pirazinil, benzotienil, benzofuril, kinolil, izokinolil ali metilendioksifenil, eventualno substituiran z 1 do 3 skupinami, izbranimi izmed R7, ali - arilalkilni, ariloksialkilni, ariltioalkilni ali arilsulfonilalkilni radikal, ali - amino skupino, disubstituirano z dvema enakima ali različnima skupinama, izbranima izmed - alkilnega radikala z 1 do 6 atomi ogljika - alkoksialkilnega, alkenilnega ali alkinilnega radikala s 3 do 6 atomi ogljika - cikloalkilnega radikala s 3 do 7 atomi ogljika arilalkilnega, fenilnega ali naftilnega radikala, eventualno substituiranega z 1 do 3 skupinami, izbranimi izmed R7, ali - tienilmetilnega ali furfurilnega radikala - pirolidino, piperidino, morfolino ali piperazino skupino, eventualno substituirano z alkilom z 1 do 3 atomi ogljika; - R5 predstavlja - H, razen, kadar je R4 H, ali - alkilni, haloalkilni, alkilsulfonilni ali haloalkilsulfonilni radikal z 1 do 6 atomi ogljika ali 11 - alkoksialkilni, alkiltioalkilni, acilni, alkenilni, alkinilni, haloacilni, alkoksikarbonilni, haloalkoksikarbonilni, alkoksialkilsulfonilni ali cianoalkilsulfonilni radikal z 2 do 6 atomi ogljika ali - alkoksialkoksikarbonilni, alkiltioalkoksikarbonilni ali cianoalkoksikarbonilni radikal s 3 do 6 atomi ogljika ali - formilni radikal ali - cikloalkilni, alkoksiacilni, alkiltioacilni, cianoacilni, alkenilkarbonilni ali alkinilkarbonilni radikal s 3 do 6 atomi ogljika ali - cikloalkilkarbonilni radikal s 4 do 8 atomi ogljika ali - radikal fenil; arilalkilkarbonil, prednostno fenilacetil in fenilpropionil; arilkarbonil, prednostno benzoil, eventualno substituiran z 1 do 3 skupinami izmed R7; tienilkarbonil; furilkarbonil; piridilkarbonil; benziloksikarbonil; furfuriloksikarbonil; tetrahidrofurfuriloksikarbonil; tienilmetoksikarbonil; piridilmetoksikarbonil; fenoksikarbonil ali (feniltio)karbonil; pri čemer je fenil sam eventualno substituiran z 1 do 3 skupinami izmed R7; (alkiltio)karbonil; (haloalkiltio)karbonil; (alkoksialkiltio)karbonil; (cianoalkiltio)karbonil; (benziltio)karbonil; (fiirfuriltio)karbonil; (tetrahidrofurfuriltio)karbonil; (tienilmetiltio)-karbonil; (piridilmetiltio)karbonil; ali arilsulfonilni radikal ali - karbamoilni radikal, eventualno mono- ali disubstituiran z - alkilno ali haloalkilno skupino z 1 do 6 atomi ogljika ali - cikloalkilno, alkenilno ali alkinilno skupino s 3 do 6 atomi ogljika ali - alkoksialkilno, alkiltioalkilno ali cianoalkilno skupino z 2 do 6 atomi ogljika ali - fenilom, eventualno substituiranim z 1 do 3 R7 skupinami; - sulfamoilno skupino, eventualno mono- ali disubstituirano z - alkilno ali haloalkilno skupino z 1 do 6 atomi ogljika ali - cikloalkilno, alkenilno ali alkinilno skupino s 3 do 6 atomi ogljika ali - alkoksialkilno, alkiltioalkilno ali cianoalkilno skupino z 2 do 6 atomi ogljika ali - fenilom, eventualno substituiranim z 1 do 3 R7 skupinami; 12 - alkiltioalkilsulfonilno skupino s 3 do 8 atomi ogljika ali cikloalkilsulfonilno skupino s 3 do 7 atomi ogljika; - Rč predstavlja - atom vodika ali - ciano skupino ali - alkilno skupino z 1 do 6 atomi ogljika ali cikloalkilno skupino s 3 do 7 atomi ogljika ali - acilno ali alkoksikarbonilno skupino z 2 do 6 atomi ogljika ali - benzoilno skupino, eventualno substituirano z 1 do 3 R7 skupinami; - R7 predstavlja - atom halogena ali - alkilni, haloalkilni, alkoksi, haloalkoksi, alkiltio, haloalkiltio ali alkilsulfonilni radikal z 1 do 6 atomi ogljika ali - cikloalkilni, halocikloalkilni, alkeniloksi, alkiniloksi, alkeniltio ali alkiniltio radikal s 3 do 6 atomi ogljika ali - nitro ali ciano skupino ali - amino radikal, eventualno mono- ali disubstituiran z alkilnim ali acilnim radikalom z 1 do 6 atomi ogljika ali alkoksikarbonilnim radikalom z 2 do 6 atomi ogljika - fenilni, fenoksi ali piridiloksi radikal, pri čemer so ti radikali eventualno substituirani; in njihovih soli.wherein - W is a sulfur or oxygen atom or the group S = 0 - A represents O or S - n = 0 or 1 - B represents NR5 or O or S or CR2 or SO2 or C = 0. - R 1 and R 2, which are the same or different, represent - H, provided that one of the two groups is other than H, or - an alkyl or haloalkyl radical having 1 to 6 carbon atoms, or - alkoxyalkyl, alkylthioalkyl, alkylsulfonylalkyl, monoalkylaminoalkyl, alkenyl or an alkynyl radical of 2 to 6 carbon atoms or - a dialkylaminoalkyl or cycloalkyl radical of 3 to 7 carbon atoms or - an aryl radical, preferably phenyl, naphthyl, thienyl, furyl, pyridyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl, or methylenedioxyphenylene with 1 to 3 groups selected from R7 or - an arylalkyl, aryloxyalkyl, arylthioalkyl or arylsulfonylalkyl radical, or - R1 and R2 may form with a ring-attached carbon a carbocycle or heterocycle of 5 to 7 atoms, with these rings may be fused to phenyl optionally substituted with 1 to 3 groups selected from R7; - R3 represents - an alkyl group having 1 to 6 carbon atoms or - an alkoxyalkyl, alkylthioalkyl, alkylsulfonylalkyl, haloalkyl, cyanoalkyl, thiocyanatoalkyl, oxoalkyl, alkenyl or alkynyl group having 2 to 6 carbon atoms or - dialkylaminoalkylalkylalkyl, alkoxyalkyl up to 6 carbon atoms or a Ν, Ν-dialkylcarbamoylalkyl group having 4 to 8 carbon atoms or a 10-arylalkyl group, the alkyl moiety being a radical having 1 to 6 carbon atoms and the aryl moiety being phenyl, naphthyl, thienyl, furyl or pyridyl, optionally substituted with 1 to 3 groups selected from R7; - R 4 represents - a hydrogen atom when n is 1, or - an alkyl group having 1 to 6 carbon atoms or - an alkoxyalkyl, alkylthioalkyl, haloalkyl, cyanoalkyl, thiocyanatoalkyl, alkenyl or alkynyl group having 2 to 6 carbon atoms or - dialkylaminoalkyl, alkoxycarbonyl or an N-alkylcarbamoylalkyl group having 3 to 6 carbon atoms or - N, a N-dialkylcarbamoylalkyl group having 4 to 8 carbon atoms or - an aryl radical, preferably phenyl, naphthyl, thienyl, furyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, benzothiene , quinolyl, isoquinolyl or methylenedioxyphenyl optionally substituted with 1 to 3 groups selected from R7, or - an arylalkyl, aryloxyalkyl, arylthioalkyl or arylsulfonylalkyl radical, or - an amino group disubstituted by two identical or different groups - alkyl selected from up to 6 carbon atoms - alkoxyalkyl, alkenyl or alkynyl radical with 3 to 6 carbon atoms - cycloalkyl radical with 3 to 7 the carbon atoms of an arylalkyl, phenyl or naphthyl radical optionally substituted by 1 to 3 groups selected from R7, or - a thienylmethyl or furfuryl radical - a pyrrolidino, piperidino, morpholino or piperazine group optionally substituted by alkyl having 1 to 3 carbon atoms; - R 5 represents - H, except when R 4 is H, or - an alkyl, haloalkyl, alkylsulfonyl or haloalkylsulfonyl radical having 1 to 6 carbon atoms or 11 - alkoxyalkyl, alkylthioalkyl, acyl, alkenyl, alkynyl, haloacyl, alkoxycarbonyl, haloalkoxyalkyl cyanoalkylsulfonyl radical having 2 to 6 carbon atoms or - alkoxyalkyloxycarbonyl, alkylthioalkoxycarbonyl or cyanoalkoxycarbonyl radical having 3 to 6 carbon atoms or - formyl radical or - cycloalkyl, alkoxyacyl, alkylthioacyl, cyanoalkylcarbonyl, alkenyl with 4 to 8 carbon atoms or - a phenyl radical; arylalkylcarbonyl, preferably phenylacetyl and phenylpropionyl; arylcarbonyl, preferably benzoyl, optionally substituted with 1 to 3 groups from R7; thienylcarbonyl; furylcarbonyl; pyridylcarbonyl; benzyloxycarbonyl; furfuryloxycarbonyl; tetrahydrofurfuryloxycarbonyl; thienylmethoxycarbonyl; pyridylmethoxycarbonyl; phenoxycarbonyl or (phenylthio) carbonyl; wherein the phenyl itself is optionally substituted with 1 to 3 groups from R7; (alkylthio) carbonyl; (haloalkylthio) carbonyl; (alkoxyalkylthio) carbonyl; (cyanoalkylthio) carbonyl; (benzylthio) carbonyl; (fiurfurylthio) carbonyl; (tetrahydrofurfurylthio) carbonyl; (thienylmethylthio) -carbonyl; (pyridylmethylthio) carbonyl; or an arylsulfonyl radical or - a carbamoyl radical optionally mono- or disubstituted by - an alkyl or haloalkyl group of 1 to 6 carbon atoms or - a cycloalkyl, alkenyl or alkynyl group of 3 to 6 carbon atoms or - an alkoxyalkyl, alkylthioalkyl or cyanoalkyl group of 2 to 6 6 carbon atoms or - phenyl optionally substituted with 1 to 3 R7 groups; - a sulfamoyl group, optionally mono- or disubstituted by - an alkyl or haloalkyl group of 1 to 6 carbon atoms, or - a cycloalkyl, alkenyl or alkynyl group of 3 to 6 carbon atoms, or - an alkoxyalkyl, alkylthioalkyl or cyanoalkyl group of 2 to 6 carbon atoms, or - phenyl optionally substituted with 1 to 3 R7 groups; 12 - an alkylthioalkylsulfonyl group having 3 to 8 carbon atoms or a cycloalkylsulfonyl group having 3 to 7 carbon atoms; - Rč represents - a hydrogen atom or - a cyano group or - an alkyl group with 1 to 6 carbon atoms or a cycloalkyl group with 3 to 7 carbon atoms or - an acyl or alkoxycarbonyl group with 2 to 6 carbon atoms or - a benzoyl group optionally substituted by 1 up to 3 R7 groups; - R7 represents - a halogen atom or - an alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio or alkylsulfonyl radical of 1 to 6 carbon atoms or - a cycloalkyl, halocycloalkyl, alkenyloxy, alkynyloxy, alkenylthio or alkynylthioalkyl radical of 3 to 6 alkyl a nitro or cyano group or an amino radical optionally mono- or disubstituted by an alkyl or acyl radical having 1 to 6 carbon atoms or an alkoxycarbonyl radical having 2 to 6 carbon atoms - a phenyl, phenoxy or pyridyloxy radical, these radicals being optionally substituted; and their salts.24. Fungicidni sestavki po zahtevku 23, označeni s tem, da vsebujejo od 0,5 do 95 mas.% spojin po enem od zahtevkov 1 do 15.Fungicidal compositions according to Claim 23, characterized in that they contain from 0.5 to 95% by weight of the compounds according to one of Claims 1 to 15.25. Postopek za obdelavo pridelkov, ki so jih prizadele ali ki so zmožni, da jih prizadenejo glivične bolezni, označen s tem, da preventivno ali kurativno apliciramo učinkovito količino spojine po enem od zahtevkov 1 do 15 ali sestavka po zahtevkih 23 ali 24. 13A process for treating crops affected or capable of being affected by fungal diseases, characterized in that an effective amount of a compound according to one of claims 1 to 15 or a composition according to claims 23 or 24 is applied preventively or curatively.26. Postopek za obdelavo po zahtevku 25, označen s tem, daje učinkovita doza med 0,005 in 5 kg/ha.The treatment method according to claim 25, characterized in that the effective dose is between 0.005 and 5 kg / ha.27. Postopek za obdelavo po zahtevku 26, označen s tem, da je učinkovita doza med 0,01 in 1 kg/ha.The treatment method according to claim 26, characterized in that the effective dose is between 0.01 and 1 kg / ha.28. Postopek za pripravo spojin s formulo (V), označen s tem, da iminoditiokarbonat s formulo (III) kondenziramo z aminom ali hidrazinom s formulo (IV) po shemi: R RProcess for the preparation of compounds of formula (V), characterized in that the iminodithiocarbonate of formula (III) is condensed with an amine or hydrazine of formula (IV) according to the scheme: RS CH3 sch3 R4—(B)n— NH2 (IV) m R V "sch3 Rf C-NH-(B)n-R4 O(V) kjer je - n = 0 ali 1 - B predstavlja NR5 ali O ali S ali CR5R6 ali SO2 ali C=0 - R in R , ki sta enaka ali različna, predstavljata - H, pod pogojem, daje ena od dveh skupin različna od H, ali - alkilni ali haloalkilni radikal z 1 do 6 atomi ogljika ali - alkoksialkilni, alkiltioalkilni, alkilsulfonilalkilni, monoalkilaminoalkilni, alkenilni ali alkinilni radikal z 2 do 6 atomi ogljika ali - dialkilaminoalkilni ali cikloalkilni radikal s 3 do 7 atomi ogljika ali - arilni radikal, prednostno fenil, naftil, tienil, furil, piridil, benzotienil, benzofuril, kinolil, izokinolil ali metilendioksifenil, eventualno substituiran z 1 do 3 skupinami, izbranimi izmed R7, ali - arilalkilni, ariloksialkilni, ariltioalkilni ali arilsulfonilalkilni radikal ali - Ri in R2 lahko tvorita z ogljikom, na katerega sta vezana na obroču, karbocikel ali heterocikel s 5 do 7 atomi, pri čemer je za te obroče mogoče, da so kondenzirani na fenil, eventualno substituiran z 1 do 3 skupinami, izbranimi izmed R7; - R4 predstavlja - atom vodika, kadar je n = 1, ali 14 - alkilno skupino z 1 do 6 atomi ogljika ali - alkoksialkilno, alkiltioalkilno, haloalkilno, cianoalkilno, tiocianatoalkilno, alkenilno ali alkinilno skupino z 2 do 6 atomi ogljika ali - dialkilaminoalkilno, alkoksikarbonilalkilno ali N-alkilkarbamoilalkilno skupino s 3 do 6 atomi ogljika ali - Ν,Ν-dialkilkarbamoilalkilno skupino s 4 do 8 atomi ogljika ali - arilni radikal, prednostno fenil, naftil, tienil, furil, piridil, pirimidil, piridazinil, pirazinil, benzotienil, benzofuril, kinolil, izokinolil ali metilendioksifenil, eventualno substituiran z 1 do 3 skupinami, izbranimi izmed R7, ali - arilalkilni, ariloksialkilni, ariltioalkilni ali arilsulfonilalkilni radikal ali - amino skupino, disubstituirano z 2 enakima ali različnima skupinama, izbranima izmed - alkilnega radikala z 1 do 6 atomi ogljika - alkoksialkilnega, alkenilnega ali alkinilnega radikala s 3 do 6 atomi ogljika - cikloalkilnega radikala s 3 do 7 atomi ogljika arilalkilnega, fenilnega ali naftilnega radikala, eventualno substituiranega z 1 do 3 skupinami, izbranimi izmed R7, ali - tienilmetilnega ali furfurilnega radikala - pirolidino, piperidino, morfolino ali piperazino skupino, eventualno substituirano z alkilom z 1 do 3 atomi ogljika; - R5 predstavlja - H, razen kadar je R4 H, ali - alkilni, haloalkilni, alkilsulfonilni ali haloalkilsulfonilni radikal z 1 do 6 atomi ogljika ali - alkoksialkilni, alkiltioalkilni, acilni, alkenilni, alkinilni, haloacilni, alkoksikarbonilni, haloalkoksikarbonilni, alkoksialkilsulfonski ali cianoalkilsulfonilni radikal z 2 do 6 atomi ogljika ali - alkoksialkoksikarbonilni, alkiltioalkoksikarbonilni ali cianoalkoksikarbonilni radikal s 3 do 6 atomi ogljika ali - formilni radikal ali 15 - cikloalkilni, alkoksiacilni, alkiltioacilni, cianoacilni, alkenilkarbonilni ali alkinilkarbonilni radikal s 3 do 6 atomi ogljika ali - cikloalkilkarbonilni radikal s 4 do 8 atomi ogljika ali - radikal fenil; arilalkilkarbonil, prednostno fenilacetil ali fenilpropionil; arilkarbonil, prednostno benzoil, eventualno substituiran z 1 do 3 skupinami izmed R7; tienilkarbonil; furilkarbonil; piridilkarbonil; benziloksikarbonil; furfuriloksikarbonil; tetrahidrofurfuriloksikarbonil; tienilmetoksikarbonil; piridilmetoksikarbonil; fenoksikarbonil ali (feniltio)karbonil, pri čemer je sam fenil eventualno substituiran z 1 do 3 skupinami izmed R7; (alkiltio)karbonil; (haloalkiltio)karbonil; (alkoksialkiltio)karbonil; (cianoalkiltio)karbonil; (benziltio)karbonil; (furfuriltio)karbonil; (tetrahidrofurfuriltio)karbonil; (tienilmetiltio)karbonil; (piridilmetiltio)karbonil; ali arilsulfonil ali - karbamoilni radikal, eventualno mono- ali disubstituiran z - alkilno ali haloalkilno skupino z 1 do 6 atomi ogljika ali - cikloalkilno, alkenilno ali alkinilno skupino s 3 do 6 atomi ogljika ali - alkoksialkilno, alkiltioalkilno ali cianoalkilno skupino z 2 do 6 atomi ogljika ali - fenilom, eventualno substituiranim z 1 do 3 R7 skupinami; - sulfamoilno skupino, eventualno mono- ali disubstituirano z - alkilno ali haloalkilno skupino z 1 do 6 atomi ogljika ali - cikloalkilno, alkenilno ali alkinilno skupino s 3 do 6 atomi ogljika ali - alkoksialkilno, alkiltioalkilno ali cianoalkilno skupino z 2 do 6 atomi ogljika ali - fenilom, eventualno substituiranim z 1 do 3 R7 skupinami; - alkiltioalkilsulfonilno skupino s 3 do 8 atomi ogljika ali cikloalkilsulfonilno skupino s 3 do 7 atomi ogljika; - R<5 predstavlja - atom vodika ali - ciano skupino ali - alkilno skupino z 1 do 6 atomi ogljika ali cikloalkilno skupino s 3 do 7 atomi ogljika ali 16 - acilno ali alkoksikarbonilno skupino z 2 do 6 atomi ogljika ali - benzoilno skupino, eventualno substituirano z 1 do 3 R7 skupinami; - R7 predstavlja - atom halogena ali - alkilni, haloalkilni, alkoksi, haloalkoksi, alkiltio, haloalkiltio ali alkilsulfonilni radikal z 1 do 6 atomi ogljika ali - cikloalkilni, halocikloalkilni, alkeniloksi, alkiniloksi, alkeniltio ali alkiniltio radikal s 3 do 6 atomi ogljika ali - nitro ali ciano skupino ali - amino radikal, eventualno mono- ali disubstituiran z alkilnim ali acilnim radikalom z 1 do 6 atomi ogljika ali alkoksikarbonilnim radikalom z 2 do 6 atomi ogljika - fenilni, fenoksi ali piridiloksi radikal, pri čemer so ti radikali eventualno substituirani; pri čemer je potrebno, da se kislina (III) aktivira za to kondenzacijo v obliki kislinskega klorida, v dicikloheksilizosečninski obliki ob uporabi dicikloheksilkarbodiimida ali v imidazolidni obliki ob uporabi karbonildiimidazola.S CH3 sch3 R4— (B) n— NH2 (IV) m RV " sch3 Rf C-NH- (B) n-R4 O (V) where - n = 0 or 1 - B represents NR5 or O or S or CR5R6 or SO2 or C = O - R and R, which are the same or different, represent - H, provided that one of the two groups is other than H, or - an alkyl or haloalkyl radical having 1 to 6 carbon atoms, or - an alkoxyalkyl , alkylthioalkyl, alkylsulfonylalkyl, monoalkylaminoalkyl, alkenyl or alkynyl radical having 2 to 6 carbon atoms or - dialkylaminoalkyl or cycloalkyl radical having 3 to 7 carbon atoms or - aryl radical, preferably phenyl, naphthyl, thienyl, furyl, pyridyl , isoquinolyl or methylenedioxyphenyl optionally substituted with 1 to 3 groups selected from R7, or - an arylalkyl, aryloxyalkyl, arylthioalkyl or arylsulfonylalkyl radical or - R1 and R2 may be formed by the ring-linked carbon, carbocycle or heterocyl. 7 atoms, it being possible for these rings to be condensed not on phenyl optionally substituted with 1 to 3 groups selected from R7; - R 4 represents - a hydrogen atom when n = 1, or a 14 - alkyl group having 1 to 6 carbon atoms, or - an alkoxyalkyl, alkylthioalkyl, haloalkyl, cyanoalkyl, thiocyanatoalkyl, alkenyl or alkynyl group having 2 to 6 carbon atoms, or - dialkylaminoalkyl, alkoxycarbonylalkyl or N-alkylcarbamoylalkyl group having 3 to 6 carbon atoms or - N, N-dialkylcarbamoylalkyl group having 4 to 8 carbon atoms or - aryl radical, preferably phenyl, naphthyl, thienyl, furyl, pyridyl, pyrimidyl, pyridine benzofuryl, quinolyl, isoquinolyl or methylenedioxyphenyl optionally substituted with 1 to 3 groups selected from R7, or - an arylalkyl, aryloxyalkyl, arylthioalkyl or arylsulfonylalkyl radical or - an amino group disubstituted by 2 identical or different groups up to 6 carbon atoms - alkoxyalkyl, alkenyl or alkynyl radical with 3 to 6 carbon atoms - cycloalkyl radical with 3 to 7 atom i a carbon of an arylalkyl, phenyl or naphthyl radical optionally substituted by 1 to 3 groups selected from R7, or - a thienylmethyl or furfuryl radical - a pyrrolidino, piperidino, morpholino or piperazine group optionally substituted by alkyl having 1 to 3 carbon atoms; - R 5 represents - H, except when R 4 is H, or - an alkyl, haloalkyl, alkylsulfonyl or haloalkylsulfonyl radical having 1 to 6 carbon atoms, or - alkoxyalkyl, alkylthioalkyl, acyl, alkenyl, alkynyl, haloacyl, alkoxycarbonyl, haloalkyloxyalkylcarbonyl with 2 to 6 carbon atoms or - alkoxyalkoxycarbonyl, alkylthioalkoxycarbonyl or cyanoalkoxycarbonyl radical with 3 to 6 carbon atoms or - formyl radical or 15 - cycloalkyl, alkoxyacyl, alkylthioacyl, cyanoacyl, alkenylcarbonyl - alkylcarbonyl or alkynylcarkyl 4 to 8 carbon atoms or - phenyl radical; arylalkylcarbonyl, preferably phenylacetyl or phenylpropionyl; arylcarbonyl, preferably benzoyl, optionally substituted with 1 to 3 groups from R7; thienylcarbonyl; furylcarbonyl; pyridylcarbonyl; benzyloxycarbonyl; furfuryloxycarbonyl; tetrahydrofurfuryloxycarbonyl; thienylmethoxycarbonyl; pyridylmethoxycarbonyl; phenoxycarbonyl or (phenylthio) carbonyl, wherein the phenyl itself is optionally substituted with 1 to 3 groups from R7; (alkylthio) carbonyl; (haloalkylthio) carbonyl; (alkoxyalkylthio) carbonyl; (cyanoalkylthio) carbonyl; (benzylthio) carbonyl; (furfurylthio) carbonyl; (tetrahydrofurfurylthio) carbonyl; (thienylmethylthio) carbonyl; (pyridylmethylthio) carbonyl; or an arylsulfonyl or - carbamoyl radical optionally mono- or disubstituted by - an alkyl or haloalkyl group of 1 to 6 carbon atoms or - a cycloalkyl, alkenyl or alkynyl group of 3 to 6 carbon atoms or - an alkoxyalkyl, alkylthioalkyl or cyanoalkyl group of 2 to 6 carbon atoms or - phenyl optionally substituted with 1 to 3 R7 groups; - a sulfamoyl group, optionally mono- or disubstituted by - an alkyl or haloalkyl group of 1 to 6 carbon atoms, or - a cycloalkyl, alkenyl or alkynyl group of 3 to 6 carbon atoms, or - an alkoxyalkyl, alkylthioalkyl or cyanoalkyl group of 2 to 6 carbon atoms, or - phenyl optionally substituted with 1 to 3 R7 groups; - an alkylthioalkylsulfonyl group having 3 to 8 carbon atoms or a cycloalkylsulfonyl group having 3 to 7 carbon atoms; - R < 5 represents - a hydrogen atom or - a cyano group or - an alkyl group with 1 to 6 carbon atoms or a cycloalkyl group with 3 to 7 carbon atoms or a 16 - acyl or alkoxycarbonyl group with 2 to 6 carbon atoms or - a benzoyl group, optionally substituted with 1 to 3 R7 groups; - R7 represents - a halogen atom or - an alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio or alkylsulfonyl radical of 1 to 6 carbon atoms or - a cycloalkyl, halocycloalkyl, alkenyloxy, alkynyloxy, alkenylthio or alkynylthioalkyl radical of 3 to 6 alkyl a nitro or cyano group or an amino radical optionally mono- or disubstituted by an alkyl or acyl radical having 1 to 6 carbon atoms or an alkoxycarbonyl radical having 2 to 6 carbon atoms - a phenyl, phenoxy or pyridyloxy radical, these radicals being optionally substituted; wherein the acid (III) is required to be activated for this condensation in the form of the acid chloride, in the dicyclohexylisourea form using dicyclohexylcarbodiimide or in the imidazolid form using carbonyldiimidazole.
SI9200391A1991-12-201992-12-16Fungicidal 2-imidazolin-5-one and 2-imidazolin-5-thione derivatives
SI9200391B
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