SI9200391B - Derivati fungicidov 2-imidazolin-5-onov in 2-imidazolin-5-tionov - Google Patents
Derivati fungicidov 2-imidazolin-5-onov in 2-imidazolin-5-tionov Download PDFInfo
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- SI9200391B SI9200391B SI9200391A SI9200391A SI9200391B SI 9200391 B SI9200391 B SI 9200391B SI 9200391 A SI9200391 A SI 9200391A SI 9200391 A SI9200391 A SI 9200391A SI 9200391 B SI9200391 B SI 9200391B
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- carbon atoms
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- NXRIDTLKJCKPOG-UHFFFAOYSA-N 1,4-dihydroimidazole-5-thione Chemical class S=C1CN=CN1 NXRIDTLKJCKPOG-UHFFFAOYSA-N 0.000 title claims abstract 3
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 title claims abstract 3
- 230000000855 fungicidal effect Effects 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims abstract 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 8
- 238000002360 preparation method Methods 0.000 claims abstract 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000005843 halogen group Chemical group 0.000 claims abstract 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 98
- -1 haloalkyl radical Chemical class 0.000 claims 78
- 125000000217 alkyl group Chemical group 0.000 claims 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 25
- 125000003342 alkenyl group Chemical group 0.000 claims 22
- 150000003254 radicals Chemical class 0.000 claims 18
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 17
- 125000001188 haloalkyl group Chemical group 0.000 claims 17
- 238000000034 method Methods 0.000 claims 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 15
- 125000000304 alkynyl group Chemical group 0.000 claims 14
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims 10
- 125000002252 acyl group Chemical group 0.000 claims 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
- 125000002541 furyl group Chemical group 0.000 claims 8
- 125000001624 naphthyl group Chemical group 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000001544 thienyl group Chemical group 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 7
- 125000004414 alkyl thio group Chemical group 0.000 claims 6
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 6
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims 6
- 125000005956 isoquinolyl group Chemical group 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000005493 quinolyl group Chemical group 0.000 claims 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 3
- IPEWNTLWCRYSRY-UHFFFAOYSA-N [CH2]C1=CC=CO1 Chemical compound [CH2]C1=CC=CO1 IPEWNTLWCRYSRY-UHFFFAOYSA-N 0.000 claims 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims 3
- 125000005108 alkenylthio group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000005256 alkoxyacyl group Chemical group 0.000 claims 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 3
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 3
- 125000005252 haloacyl group Chemical group 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims 3
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 2
- 239000003849 aromatic solvent Substances 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 150000005840 aryl radicals Chemical class 0.000 claims 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052740 iodine Chemical group 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 125000005188 oxoalkyl group Chemical group 0.000 claims 2
- 150000002978 peroxides Chemical class 0.000 claims 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- SCCCIUGOOQLDGW-UHFFFAOYSA-N 1,1-dicyclohexylurea Chemical group C1CCCCC1N(C(=O)N)C1CCCCC1 SCCCIUGOOQLDGW-UHFFFAOYSA-N 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- AZZPAAYLMUOGNP-UHFFFAOYSA-N 2-methylsulfanyl-1,4-dihydroimidazol-5-one Chemical class CSC1=NC(=O)CN1 AZZPAAYLMUOGNP-UHFFFAOYSA-N 0.000 claims 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- 208000031888 Mycoses Diseases 0.000 claims 1
- SPTHOEKISABNFX-UHFFFAOYSA-N OC(=S)S=N Chemical compound OC(=S)S=N SPTHOEKISABNFX-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000011149 active material Substances 0.000 claims 1
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 150000004292 cyclic ethers Chemical class 0.000 claims 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims 1
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 150000002540 isothiocyanates Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 150000004965 peroxy acids Chemical class 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
- C07C331/20—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/14—Dithiocarbamic acids; Derivatives thereof
- C07C333/18—Esters of dithiocarbamic acids
- C07C333/20—Esters of dithiocarbamic acids having nitrogen atoms of dithiocarbamate groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (28)
1 Patentni zahtevki 1. Spojine z imidazolinon ali imidazolintion skupino, označene s tem, da ustrezajo splošni formuli (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.
2. Spojine po zahtevku 1, označene s tem, da je A atom žvepla.
3. Spojine po zahtevku 1, označene s tem, daje W atom kisika.
4. Spojine po zahtevku 2, označene s tem, da ustrezajo splošni formuli
la kjer imajo W, n in Rj do R$ enak pomen kot v zahtevku 1.
5. Spojine po zahtevku 2, označene s tem, da ustrezajo splošni formuli
5 Ib kjer imajo W ter Rj do R5 enak pomen kot v zahtevku 1.
6. Spojine po zahtevku 2, označene s tem, da ustrezajo splošni formuli
Ic kjer imajo B, n in Ri do R4 enak pomen kot v zahtevku 1. 6
7. Spojine po zahtevku 2, označene s tem, da ustrezajo splošni formuli
v kateri imajo B, n in do R4 enak pomen kot v zahtevku 1.
8. Spojine po enem od zahtevkov 1 do 7, označene s tem, da je R5 atom vodika.
9. Spojine po zahtevku 5, označene s tem, daje R5 atom vodika (spojina Ib').
10. Spojine po enem od zahtevkov 1 do 9, označene s tem, da R! in R2 nista atoma vodika.
11. Spojine po enem od zahtevkov 1 do 10, označene s tem, daje R2 alkilna skupina z 1 do 3 atomi ogljika.
12. Spojine po enem od zahtevkov 1 do 11, označene s tem, daje Ri fenil, eventualno substituiran s skupino R7.
13. Spojine po enem od zahtevkov 1 do 12, označene s tem, daje R3 alkilna skupina z 1 do 3 atomi ogljika.
14. Spojine po enem od zahtevkov 1 do 13, označene s tem, daje R4 fenil, eventualno substituiran s skupino R7.
15. Spojine po enem od zahtevkov 1 do 14, označene s tem, daje R3 metilni radikal.
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 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.
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) -R4
kjer imajo Ri, R2, R4, B in n enak pomen kot v zahtevku 1.
18. Postopek za pripravo spojin s formulo (Ib) (postopek Cl) po shemi:
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. 8
19. Postopek za pripravo spojin s formulo (Id) (postopek C2) po shemi:
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.
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.
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.
22. Postopek po zahtevku 21, označen s tem, da je peroksid perkislina in topilo izberemo iz skupine, ki obsega kloroform in metilenklorid.
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) 9
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.
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.
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. 13
26. Postopek za obdelavo po zahtevku 25, označen s tem, daje učinkovita doza med 0,005 in 5 kg/ha.
27. Postopek za obdelavo po zahtevku 26, označen s tem, da je učinkovita doza med 0,01 in 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 R
S 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.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9116200A FR2685328B1 (fr) | 1991-12-20 | 1991-12-20 | Derives de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9200391A SI9200391A (en) | 1993-06-30 |
| SI9200391B true SI9200391B (sl) | 2002-02-28 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9200391A SI9200391B (sl) | 1991-12-20 | 1992-12-16 | Derivati fungicidov 2-imidazolin-5-onov in 2-imidazolin-5-tionov |
Country Status (32)
| Country | Link |
|---|---|
| EP (1) | EP0551048B1 (sl) |
| JP (1) | JP3462516B2 (sl) |
| KR (1) | KR100263576B1 (sl) |
| CN (1) | CN1035594C (sl) |
| AP (1) | AP405A (sl) |
| AT (1) | ATE221878T1 (sl) |
| AU (2) | AU651021B2 (sl) |
| BR (1) | BR9204699A (sl) |
| CA (1) | CA2085192C (sl) |
| CZ (1) | CZ287207B6 (sl) |
| DE (1) | DE69232719T2 (sl) |
| DK (1) | DK0551048T3 (sl) |
| EC (1) | ECSP920893A (sl) |
| EG (1) | EG19910A (sl) |
| ES (1) | ES2176186T3 (sl) |
| FI (1) | FI119732B (sl) |
| FR (1) | FR2685328B1 (sl) |
| HR (1) | HRP921456B1 (sl) |
| HU (1) | HU215384B (sl) |
| IL (2) | IL104091A (sl) |
| MA (1) | MA22747A1 (sl) |
| MX (1) | MX9207383A (sl) |
| MY (1) | MY110823A (sl) |
| NZ (1) | NZ245489A (sl) |
| PL (1) | PL170819B1 (sl) |
| PT (1) | PT551048E (sl) |
| RU (1) | RU2111207C1 (sl) |
| SI (1) | SI9200391B (sl) |
| SK (1) | SK283470B6 (sl) |
| TW (1) | TW267928B (sl) |
| YU (1) | YU49164B (sl) |
| ZA (1) | ZA929772B (sl) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3931907A1 (de) * | 1989-09-25 | 1991-04-04 | Henkel Kgaa | Waessriges lackoverspray-schutzcoating fuer spritzkabinen sowie verfahren zu dessen herstellung |
| FR2706455B1 (fr) * | 1993-06-18 | 1995-08-04 | Rhone Poulenc Agrochimie | Dérivés optiquement actifs de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
| US6002016A (en) * | 1991-12-20 | 1999-12-14 | Rhone-Poulenc Agrochimie | Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones |
| FR2698359B1 (fr) * | 1992-11-25 | 1995-10-27 | Rhone Poulenc Agrochimie | Derives de 2-alkoxy 2-imidazoline-5-ones fongicides. |
| FR2706456B1 (fr) * | 1993-06-18 | 1996-06-28 | Rhone Poulenc Agrochimie | Dérivés optiquement actifs de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
| FR2685328B1 (fr) * | 1991-12-20 | 1995-12-01 | Rhone Poulenc Agrochimie | Derives de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
| EP1008589A1 (en) * | 1992-05-22 | 2000-06-14 | E.I. Du Pont De Nemours & Company Incorporated | Fungicidal imidazolinones |
| US6008370A (en) * | 1992-11-25 | 1999-12-28 | Rhone-Poulenc Agrochimie | Fungicidal-2-alkoxy/haloalkoxy-1-(mono- or disubstituted)amino-4,4-disubstituted-2-imidazolin-5-ones |
| FR2716192B1 (fr) * | 1994-02-17 | 1996-04-12 | Rhone Poulenc Agrochimie | Dérivés de 2-imidazoline-5-ones fongicides. |
| AU1892495A (en) * | 1994-03-09 | 1995-09-25 | Rhone-Poulenc Agrochimie | Pesticide substituted 2-imidazolinones |
| FR2721022B1 (fr) * | 1994-06-10 | 1996-07-19 | Rhone Poulenc Agrochimie | Dérivés de 5-imino 2-imidazolines fongicides. |
| FR2722499B1 (fr) * | 1994-07-13 | 1996-08-23 | Rhone Poulenc Agrochimie | Nouveaux derives de 2-imidazoline-5-ones fongicides |
| FR2722652B1 (fr) | 1994-07-22 | 1997-12-19 | Rhone Poulenc Agrochimie | Composition fongicide comprenant une 2-imidazoline-5-one |
| EP0760239A3 (en) * | 1995-09-01 | 1999-04-14 | Pfizer Inc. | Therapeutic agents for use in cancer therapy |
| FR2751327A1 (fr) | 1996-07-22 | 1998-01-23 | Rhone Poulenc Agrochimie | Intermediaires pour la preparation de 2-imidazoline-5-ones |
| UA61064C2 (uk) * | 1997-12-02 | 2003-11-17 | Рон-Пуленк Агро | Синергічна фунгіцидна композиція, що містить 2-інідазолін-5-он та спосіб боротьби з фітопатогенними грибками культур |
| UA70327C2 (uk) | 1998-06-08 | 2004-10-15 | Баєр Акціенгезельшафт | Спосіб боротьби з фітопатогенними хворобами сільськогосподарських рослин та фунгіцидна композиція |
| FR2783401B1 (fr) * | 1998-09-21 | 2000-10-20 | Rhone Poulenc Agrochimie | Nouvelles compositions fongicides |
| EP1092712A1 (en) * | 1999-10-13 | 2001-04-18 | E.I. Du Pont De Nemours And Company | Process for preparing fungicidal oxazolidinones and imidazolinones |
| SI1501355T1 (sl) | 2002-04-24 | 2010-09-30 | Basf Se | Uporaba definiranih alkoholnih alkoksilatov kot pripomočkov na agrotehničnem področju |
| CN101863835B (zh) * | 2010-06-29 | 2012-10-10 | 渤海大学 | S-取代-5,5-二苯基-2-硫代海因衍生物的合成方法 |
| CN103081915A (zh) * | 2011-11-07 | 2013-05-08 | 深圳诺普信农化股份有限公司 | 一种杀菌组合物 |
| EP2622961A1 (en) | 2012-02-02 | 2013-08-07 | Bayer CropScience AG | Acive compound combinations |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2329276A1 (fr) * | 1975-10-29 | 1977-05-27 | Roussel Uclaf | Nouvelles imidazolidines substituees, procede de preparation, application comme medicament et compositions les renfermant |
| DE3305203A1 (de) * | 1983-02-16 | 1984-08-16 | Bayer Ag, 5090 Leverkusen | N-sulfenylierte hydantoine, ein verfahren zu ihrer herstellung und ihre verwendung als mikrobizide |
| DE3340595A1 (de) * | 1983-11-10 | 1985-05-23 | Hoechst Ag, 6230 Frankfurt | Imidazolinone, verfahren zu ihrer herstellung und ihre verwendung im pflanzenschutz |
| DE3634887A1 (de) * | 1986-10-14 | 1988-04-21 | Bayer Ag | 2-(5-oxo-2-imidazolin-2-yl)-pyridin-derivate |
| EP0283245A1 (en) * | 1987-03-20 | 1988-09-21 | E.I. Du Pont De Nemours And Company | Fungicidal aminotriazoles and aminoimidazoles |
| DK0393911T3 (da) * | 1989-04-21 | 1994-10-03 | Du Pont | Fungicide oxazolidinoner |
| PT97078B (pt) * | 1990-03-20 | 1997-07-31 | Sanofi Sa | Processo para a preparacao de derivados heterociclicos n-substituidos e de composicoes farmaceuticas que os contem |
| FR2671348B1 (fr) * | 1991-01-09 | 1993-03-26 | Roussel Uclaf | Nouvelles phenylimidazolidines, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant. |
| FR2706456B1 (fr) * | 1993-06-18 | 1996-06-28 | Rhone Poulenc Agrochimie | Dérivés optiquement actifs de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
| FR2685328B1 (fr) * | 1991-12-20 | 1995-12-01 | Rhone Poulenc Agrochimie | Derives de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
| EP1008589A1 (en) * | 1992-05-22 | 2000-06-14 | E.I. Du Pont De Nemours & Company Incorporated | Fungicidal imidazolinones |
-
1991
- 1991-12-20 FR FR9116200A patent/FR2685328B1/fr not_active Expired - Lifetime
-
1992
- 1992-02-17 EG EG78692A patent/EG19910A/xx active
- 1992-12-11 CA CA002085192A patent/CA2085192C/fr not_active Expired - Lifetime
- 1992-12-14 IL IL104091A patent/IL104091A/en not_active IP Right Cessation
- 1992-12-16 MY MYPI92002315A patent/MY110823A/en unknown
- 1992-12-16 AT AT92420461T patent/ATE221878T1/de active
- 1992-12-16 EP EP92420461A patent/EP0551048B1/fr not_active Expired - Lifetime
- 1992-12-16 DK DK92420461T patent/DK0551048T3/da active
- 1992-12-16 NZ NZ245489A patent/NZ245489A/en unknown
- 1992-12-16 EC EC1992000893A patent/ECSP920893A/es unknown
- 1992-12-16 MA MA23037A patent/MA22747A1/fr unknown
- 1992-12-16 ES ES92420461T patent/ES2176186T3/es not_active Expired - Lifetime
- 1992-12-16 SI SI9200391A patent/SI9200391B/sl unknown
- 1992-12-16 DE DE69232719T patent/DE69232719T2/de not_active Expired - Lifetime
- 1992-12-16 PT PT92420461T patent/PT551048E/pt unknown
- 1992-12-17 MX MX9207383A patent/MX9207383A/es unknown
- 1992-12-17 ZA ZA929772A patent/ZA929772B/xx unknown
- 1992-12-18 HU HUP9204030A patent/HU215384B/hu not_active IP Right Cessation
- 1992-12-18 FI FI925763A patent/FI119732B/fi not_active IP Right Cessation
- 1992-12-18 CZ CS19923753A patent/CZ287207B6/cs not_active IP Right Cessation
- 1992-12-18 YU YU109092A patent/YU49164B/sh unknown
- 1992-12-18 PL PL92297064A patent/PL170819B1/pl unknown
- 1992-12-18 BR BR9204699A patent/BR9204699A/pt not_active IP Right Cessation
- 1992-12-18 SK SK3753-92A patent/SK283470B6/sk not_active IP Right Cessation
- 1992-12-18 TW TW081110177A patent/TW267928B/zh active
- 1992-12-18 AU AU30310/92A patent/AU651021B2/en not_active Ceased
- 1992-12-18 RU RU92016214A patent/RU2111207C1/ru active
- 1992-12-19 KR KR1019920024827A patent/KR100263576B1/ko not_active Expired - Lifetime
- 1992-12-21 JP JP35634492A patent/JP3462516B2/ja not_active Expired - Fee Related
- 1992-12-21 AP APAP/P/1992/000466A patent/AP405A/en active
- 1992-12-21 CN CN92115091A patent/CN1035594C/zh not_active Expired - Lifetime
- 1992-12-22 HR HR921456A patent/HRP921456B1/xx not_active IP Right Cessation
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1994
- 1994-10-07 AU AU74499/94A patent/AU671389B2/en not_active Ceased
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1997
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