CA1079735A - Organic fluoroethyl-imides and amides, their preparation and use - Google Patents
Organic fluoroethyl-imides and amides, their preparation and useInfo
- Publication number
- CA1079735A CA1079735A CA266,200A CA266200A CA1079735A CA 1079735 A CA1079735 A CA 1079735A CA 266200 A CA266200 A CA 266200A CA 1079735 A CA1079735 A CA 1079735A
- Authority
- CA
- Canada
- Prior art keywords
- difluoro
- compound according
- trichloroethylthio
- compound
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000001408 amides Chemical class 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- 239000000460 chlorine Substances 0.000 claims abstract description 19
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
- 239000011737 fluorine Substances 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- 239000002023 wood Substances 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 5
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 5
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 5
- CIFFBTOJCKSRJY-UHFFFAOYSA-N 3α,4,7,7α-tetrahydro-1h-isoindole-1,3(2h)-dione Chemical compound C1C=CCC2C(=O)NC(=O)C21 CIFFBTOJCKSRJY-UHFFFAOYSA-N 0.000 claims description 3
- 241000238876 Acari Species 0.000 claims description 3
- BOMWUICNTBDQAJ-UHFFFAOYSA-N 2-(1,1,2-trichloro-2,2-difluoroethyl)sulfanyl-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1CC=CC2C(=O)N(SC(Cl)(Cl)C(F)(Cl)F)C(=O)C21 BOMWUICNTBDQAJ-UHFFFAOYSA-N 0.000 claims description 2
- NLGZRKQHMNPTGW-UHFFFAOYSA-N 2-(1,1,2-trichloro-2,2-difluoroethyl)sulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)C(F)(Cl)F)C(=O)C2=C1 NLGZRKQHMNPTGW-UHFFFAOYSA-N 0.000 claims description 2
- YLGSVUZVGYPLLJ-UHFFFAOYSA-N 2-(1,2-dichloro-1,2,2-trifluoroethyl)sulfanyl-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1CC=CC2C(=O)N(SC(F)(Cl)C(F)(Cl)F)C(=O)C21 YLGSVUZVGYPLLJ-UHFFFAOYSA-N 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 230000002538 fungal effect Effects 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 244000038559 crop plants Species 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000000376 reactant Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- AVXHCUKQISJQBN-UHFFFAOYSA-N chloromethanesulfonamide Chemical compound NS(=O)(=O)CCl AVXHCUKQISJQBN-UHFFFAOYSA-N 0.000 claims 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 8
- 230000000855 fungicidal effect Effects 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 241000233866 Fungi Species 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- 244000141359 Malus pumila Species 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 3
- ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 description 3
- 239000005745 Captan Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000011430 Malus pumila Nutrition 0.000 description 3
- 235000015103 Malus silvestris Nutrition 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000007238 Secale cereale Nutrition 0.000 description 3
- 244000082988 Secale cereale Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 229940117949 captan Drugs 0.000 description 3
- 230000003129 miticidal effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 241001626940 Coniophora cerebella Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
- 241000018646 Pinus brutia Species 0.000 description 2
- 235000011613 Pinus brutia Nutrition 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 2
- 229920000940 maneb Polymers 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- ZEVCJZRMCOYJSP-UHFFFAOYSA-N sodium;2-(dithiocarboxyamino)ethylcarbamodithioic acid Chemical compound [Na+].SC(=S)NCCNC(S)=S ZEVCJZRMCOYJSP-UHFFFAOYSA-N 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- RZZPDXZPRHQOCG-OJAKKHQRSA-O CDP-choline(1+) Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OCC[N+](C)(C)C)O[C@H]1N1C(=O)N=C(N)C=C1 RZZPDXZPRHQOCG-OJAKKHQRSA-O 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241001600093 Coniophora Species 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 241001492222 Epicoccum Species 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000222640 Polyporus Species 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 241001674251 Serpula lacrymans Species 0.000 description 1
- 241000722133 Tilletia Species 0.000 description 1
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 241001154828 Urocystis <tapeworm> Species 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004453 electron probe microanalysis Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229940096118 ella Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- UFZOPKFMKMAWLU-UHFFFAOYSA-N ethoxy(methyl)phosphinic acid Chemical compound CCOP(C)(O)=O UFZOPKFMKMAWLU-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- TZBQEYJPVLKASB-UHFFFAOYSA-N n-(4-chlorophenyl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(Cl)C=C1 TZBQEYJPVLKASB-UHFFFAOYSA-N 0.000 description 1
- LBTPIFQNEKOAIM-UHFFFAOYSA-N n-phenylmethanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1 LBTPIFQNEKOAIM-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- OOLLAFOLCSJHRE-ZHAKMVSLSA-N ulipristal acetate Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(OC(C)=O)C(C)=O)[C@]2(C)C1 OOLLAFOLCSJHRE-ZHAKMVSLSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/343—Heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB48441/75A GB1499169A (en) | 1975-11-25 | 1975-11-25 | Organic fluoro-imides their preparation and use |
| GB3582076 | 1976-08-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1079735A true CA1079735A (en) | 1980-06-17 |
Family
ID=26262871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA266,200A Expired CA1079735A (en) | 1975-11-25 | 1976-11-22 | Organic fluoroethyl-imides and amides, their preparation and use |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4148901A (d) |
| JP (1) | JPS5265244A (d) |
| AT (1) | AT355006B (d) |
| BR (1) | BR7607880A (d) |
| CA (1) | CA1079735A (d) |
| CH (1) | CH618679A5 (d) |
| DD (1) | DD129283A5 (d) |
| DE (1) | DE2652451A1 (d) |
| DK (1) | DK527176A (d) |
| ES (1) | ES453600A1 (d) |
| FR (2) | FR2333783A1 (d) |
| NL (1) | NL7613166A (d) |
| SU (1) | SU701533A3 (d) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4282241A (en) * | 1975-11-25 | 1981-08-04 | A/S Cheminova | Organic fluoro-imides, their preparation and use |
| GB1499169A (en) * | 1975-11-25 | 1978-01-25 | Cheminova As | Organic fluoro-imides their preparation and use |
| US4210759A (en) * | 1978-05-24 | 1980-07-01 | Henkel Corporation | Benzene sulfonamido pyridine derivatives |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1193037B (de) * | 1959-11-10 | 1965-05-20 | Bayer Ag | Verfahren zur Herstellung von N-(Polyhalogen-alkansulfenyl)-sulfonsaeureamiden |
| BE607558A (d) * | 1960-08-26 | |||
| BE616336A (d) * | 1960-11-03 | |||
| DK109482C (da) * | 1960-11-03 | 1968-04-29 | Bayer Ag | Fungicid og fremgangsmåder til fremstilling af sulfensyrederivater til anvendelse i fungicidet. |
| FR1365808A (fr) * | 1962-08-08 | 1964-07-03 | Bayer Ag | Agents acaricides |
| US3314969A (en) * | 1963-07-30 | 1967-04-18 | Chevron Res | Process for the preparation of n-polyhaloethylthio compounds |
| DE1238139B (de) * | 1964-04-11 | 1967-04-06 | Bayer Ag | Mikrobizide Mittel fuer Anstriche und Kunststoffueberzuege |
| AT302721B (de) * | 1967-10-05 | 1972-10-25 | Stauffer Chemical Co | Mittel zur Bekämpfung von Milben und Pilzen |
| IL30807A0 (en) * | 1967-10-05 | 1968-12-26 | Stauffer Chemical Co | (tetrachloro-fluoro-ethyl-thio)-n-phenyl sulfamides and their use in controlling pests |
| US3840555A (en) * | 1971-03-10 | 1974-10-08 | Stauffer Chemical Co | Miticidal active fluoro phthalimide derivatives |
| US4092429A (en) * | 1976-02-09 | 1978-05-30 | Stauffer Chemical Company | (Tetrachloro-fluoro-ethyl-thio)N-phenyl sulfonamides and their use in controlling pests |
-
1976
- 1976-11-17 DE DE19762652451 patent/DE2652451A1/de not_active Withdrawn
- 1976-11-17 US US05/742,592 patent/US4148901A/en not_active Expired - Lifetime
- 1976-11-19 AT AT862276A patent/AT355006B/de not_active IP Right Cessation
- 1976-11-22 CH CH1466476A patent/CH618679A5/fr not_active IP Right Cessation
- 1976-11-22 CA CA266,200A patent/CA1079735A/en not_active Expired
- 1976-11-23 DK DK527176A patent/DK527176A/da unknown
- 1976-11-24 ES ES453600A patent/ES453600A1/es not_active Expired
- 1976-11-24 DD DD7600195939A patent/DD129283A5/xx unknown
- 1976-11-24 BR BR7607880A patent/BR7607880A/pt unknown
- 1976-11-25 SU SU762425174A patent/SU701533A3/ru active
- 1976-11-25 JP JP51141749A patent/JPS5265244A/ja active Pending
- 1976-11-25 NL NL7613166A patent/NL7613166A/xx not_active Application Discontinuation
- 1976-11-25 FR FR7635597A patent/FR2333783A1/fr not_active Withdrawn
-
1977
- 1977-05-06 FR FR7713945A patent/FR2339599A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2333783A1 (fr) | 1977-07-01 |
| AT355006B (de) | 1980-02-11 |
| FR2339599B1 (d) | 1982-03-26 |
| BR7607880A (pt) | 1977-10-25 |
| FR2339599A1 (fr) | 1977-08-26 |
| JPS5265244A (en) | 1977-05-30 |
| NL7613166A (nl) | 1977-05-27 |
| CH618679A5 (d) | 1980-08-15 |
| DE2652451A1 (de) | 1977-06-08 |
| US4148901A (en) | 1979-04-10 |
| DK527176A (da) | 1977-05-26 |
| ATA862276A (de) | 1979-07-15 |
| SU701533A3 (ru) | 1979-11-30 |
| ES453600A1 (es) | 1977-11-16 |
| DD129283A5 (de) | 1978-01-11 |
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