IL45214A - 1-(1,2,4-triazol-1-yl)-2-phenoxy-4,4-dimethylpentan-3-one derivatives their preparation and fungicidal compositions containing them - Google Patents
1-(1,2,4-triazol-1-yl)-2-phenoxy-4,4-dimethylpentan-3-one derivatives their preparation and fungicidal compositions containing themInfo
- Publication number
- IL45214A IL45214A IL45214A IL4521474A IL45214A IL 45214 A IL45214 A IL 45214A IL 45214 A IL45214 A IL 45214A IL 4521474 A IL4521474 A IL 4521474A IL 45214 A IL45214 A IL 45214A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- active
- triazole
- process according
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 7
- 230000000855 fungicidal effect Effects 0.000 title abstract description 7
- GLQWJGFEJAFCHQ-UHFFFAOYSA-N 4,4-dimethyl-2-phenoxy-1-(1,2,4-triazol-1-yl)pentan-3-one Chemical class C=1C=CC=CC=1OC(C(=O)C(C)(C)C)CN1C=NC=N1 GLQWJGFEJAFCHQ-UHFFFAOYSA-N 0.000 title 1
- 125000000468 ketone group Chemical group 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 3
- 150000002825 nitriles Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 22
- 239000003085 diluting agent Substances 0.000 claims description 13
- 241000233866 Fungi Species 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- -1 alkaline earth metal carbonate Chemical class 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000006378 damage Effects 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- ALNWCYLRUYXLCD-UHFFFAOYSA-N 1-ethyltriazole Chemical class CCN1C=CN=N1 ALNWCYLRUYXLCD-UHFFFAOYSA-N 0.000 claims 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 3
- 239000011230 binding agent Substances 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 208000015181 infectious disease Diseases 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000209219 Hordeum Species 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 5
- 239000007921 spray Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 206010037888 Rash pustular Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 231100000162 fungitoxic Toxicity 0.000 description 2
- 230000002464 fungitoxic effect Effects 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 208000029561 pustule Diseases 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- ONNDGYXYNGPSJT-UHFFFAOYSA-N 2,2-diethyl-1,4-dioxane Chemical compound CCC1(CC)COCCO1 ONNDGYXYNGPSJT-UHFFFAOYSA-N 0.000 description 1
- NXTOCVYXABBSGX-UHFFFAOYSA-N 3-methyloctan-4-one Chemical compound CCCCC(=O)C(C)CC NXTOCVYXABBSGX-UHFFFAOYSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000287436 Turdus merula Species 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- RYPWQHONZWFXBN-UHFFFAOYSA-N dichloromethyl(methylidene)-$l^{3}-chlorane Chemical compound ClC(Cl)Cl=C RYPWQHONZWFXBN-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000008659 phytopathology Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2335020A DE2335020C3 (de) | 1973-07-10 | 1973-07-10 | 1-(1,2,4-Triazol-1-yl)-2-phenoxy-4,4-dimethyl-pentan-3-on-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL45214A0 IL45214A0 (en) | 1974-10-22 |
| IL45214A true IL45214A (en) | 1977-05-31 |
Family
ID=5886459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL45214A IL45214A (en) | 1973-07-10 | 1974-07-08 | 1-(1,2,4-triazol-1-yl)-2-phenoxy-4,4-dimethylpentan-3-one derivatives their preparation and fungicidal compositions containing them |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US3974174A (hu) |
| JP (2) | JPS5756444B2 (hu) |
| AR (1) | AR205894A1 (hu) |
| AT (1) | AT335227B (hu) |
| BE (1) | BE817347A (hu) |
| BR (1) | BR7405669D0 (hu) |
| CA (1) | CA1069907A (hu) |
| CH (1) | CH564543A5 (hu) |
| CS (1) | CS189656B2 (hu) |
| DD (1) | DD117800A5 (hu) |
| DE (1) | DE2335020C3 (hu) |
| DK (1) | DK138181C (hu) |
| ES (1) | ES428101A1 (hu) |
| FR (1) | FR2236863B1 (hu) |
| GB (1) | GB1418287A (hu) |
| HU (1) | HU168174B (hu) |
| IL (1) | IL45214A (hu) |
| IT (1) | IT1046132B (hu) |
| LU (1) | LU70480A1 (hu) |
| NL (1) | NL7409222A (hu) |
| PL (1) | PL91386B1 (hu) |
| SE (1) | SE7409016L (hu) |
| SU (1) | SU515428A3 (hu) |
| TR (1) | TR18438A (hu) |
| ZA (1) | ZA744388B (hu) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4147791A (en) * | 1972-01-11 | 1979-04-03 | Bayer Aktiengesellschaft | 1-Substituted-1,2,4-triazole fungicidal compositions and methods for combatting fungi that infect or attack plants |
| DE2547954A1 (de) * | 1975-10-27 | 1977-04-28 | Bayer Ag | 1-(2-halogen-2-phenyl-aethyl)-triazole, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2645496A1 (de) * | 1976-10-08 | 1978-04-13 | Bayer Ag | (1-phenyl-2-triazolyl-aethyl)-thioaether-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide und wachstumsregulatoren |
| DE2652313A1 (de) * | 1976-11-17 | 1978-05-18 | Basf Ag | Triazolderivate |
| DE2745827A1 (de) * | 1977-10-12 | 1979-04-26 | Basf Ag | Phenylazophenyloxy-triazolylverbindungen |
| DE2832234A1 (de) * | 1978-07-21 | 1980-01-31 | Bayer Ag | Alpha -azolyl-keto-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2833194A1 (de) * | 1978-07-28 | 1980-02-14 | Basf Ag | Triazolderivate |
| DE2846980A1 (de) * | 1978-10-28 | 1980-05-08 | Bayer Ag | 1-ethen-azol-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| US4584307A (en) * | 1983-08-10 | 1986-04-22 | Pfizer Inc. | Antifungal 2-aryl-2-hydroxy perfluoro-1-(1H-1,2,4-triazol-1-yl) alkanones and alkanols |
| DE3407005A1 (de) * | 1983-09-26 | 1985-04-04 | Bayer Ag, 5090 Leverkusen | Hydroxyethylazolyl-oxim-derivate |
| EP2349489B1 (en) * | 2008-11-25 | 2015-11-11 | The Procter and Gamble Company | Low ph oral care compositions with fused silica and a fluoride source |
-
1973
- 1973-07-10 DE DE2335020A patent/DE2335020C3/de not_active Expired
-
1974
- 1974-01-01 AR AR254603A patent/AR205894A1/es active
- 1974-06-27 US US05/483,758 patent/US3974174A/en not_active Expired - Lifetime
- 1974-07-02 CS CS744657A patent/CS189656B2/cs unknown
- 1974-07-08 CH CH934274A patent/CH564543A5/xx not_active IP Right Cessation
- 1974-07-08 NL NL7409222A patent/NL7409222A/xx not_active Application Discontinuation
- 1974-07-08 IL IL45214A patent/IL45214A/en unknown
- 1974-07-08 IT IT24919/74A patent/IT1046132B/it active
- 1974-07-08 DD DD179785A patent/DD117800A5/xx unknown
- 1974-07-08 BE BE146301A patent/BE817347A/xx not_active IP Right Cessation
- 1974-07-08 PL PL1974172542A patent/PL91386B1/pl unknown
- 1974-07-08 SU SU2041672A patent/SU515428A3/ru active
- 1974-07-08 LU LU70480A patent/LU70480A1/xx unknown
- 1974-07-09 ZA ZA00744388A patent/ZA744388B/xx unknown
- 1974-07-09 GB GB3037074A patent/GB1418287A/en not_active Expired
- 1974-07-09 SE SE7409016A patent/SE7409016L/xx unknown
- 1974-07-09 ES ES428101A patent/ES428101A1/es not_active Expired
- 1974-07-09 TR TR18438A patent/TR18438A/xx unknown
- 1974-07-09 CA CA204,388A patent/CA1069907A/en not_active Expired
- 1974-07-09 HU HUBA3112A patent/HU168174B/hu unknown
- 1974-07-09 DK DK367574A patent/DK138181C/da active
- 1974-07-09 AT AT565574A patent/AT335227B/de not_active IP Right Cessation
- 1974-07-10 FR FR7424023A patent/FR2236863B1/fr not_active Expired
- 1974-07-10 JP JP49078355A patent/JPS5756444B2/ja not_active Expired
- 1974-07-10 BR BR5669/74A patent/BR7405669D0/pt unknown
- 1974-07-10 JP JP49078354A patent/JPS5835190B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ZA744388B (en) | 1975-07-30 |
| ATA565574A (de) | 1976-06-15 |
| AU7097074A (en) | 1976-01-08 |
| CH564543A5 (hu) | 1975-07-31 |
| BR7405669D0 (pt) | 1975-05-20 |
| CS189656B2 (en) | 1979-04-30 |
| DE2335020B2 (hu) | 1980-11-20 |
| HU168174B (hu) | 1976-03-28 |
| PL91386B1 (hu) | 1977-02-28 |
| DE2335020A1 (de) | 1975-01-30 |
| JPS5835190B2 (ja) | 1983-08-01 |
| SE7409016L (sv) | 1975-01-13 |
| TR18438A (tr) | 1977-02-16 |
| DK138181C (da) | 1978-12-27 |
| JPS5040750A (hu) | 1975-04-14 |
| JPS5756444B2 (hu) | 1982-11-30 |
| DK367574A (hu) | 1975-03-03 |
| AT335227B (de) | 1977-02-25 |
| DD117800A5 (hu) | 1976-02-05 |
| SU515428A3 (ru) | 1976-05-25 |
| DK138181B (da) | 1978-07-24 |
| IL45214A0 (en) | 1974-10-22 |
| FR2236863A1 (hu) | 1975-02-07 |
| FR2236863B1 (hu) | 1978-02-17 |
| IT1046132B (it) | 1980-06-30 |
| GB1418287A (en) | 1975-12-17 |
| CA1069907A (en) | 1980-01-15 |
| LU70480A1 (hu) | 1975-03-27 |
| DE2335020C3 (de) | 1981-10-08 |
| US3974174A (en) | 1976-08-10 |
| AR205894A1 (es) | 1976-06-15 |
| NL7409222A (nl) | 1975-01-14 |
| BE817347A (fr) | 1975-01-08 |
| ES428101A1 (es) | 1976-07-16 |
| JPS5040569A (hu) | 1975-04-14 |
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