JPS6026110B2 - 新規アゾリル−カルボン酸誘導体，その製造方法およびそれを有効成分として含有する殺菌剤組成物 - Google Patents
新規アゾリル−カルボン酸誘導体，その製造方法およびそれを有効成分として含有する殺菌剤組成物Info
- Publication number
- JPS6026110B2 JPS6026110B2 JP52093448A JP9344877A JPS6026110B2 JP S6026110 B2 JPS6026110 B2 JP S6026110B2 JP 52093448 A JP52093448 A JP 52093448A JP 9344877 A JP9344877 A JP 9344877A JP S6026110 B2 JPS6026110 B2 JP S6026110B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- keto
- carboxylic acid
- acid derivative
- 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
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- 238000004519 manufacturing process Methods 0.000 title claims description 4
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- 238000000034 method Methods 0.000 claims description 16
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
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- 229910010277 boron hydride Inorganic materials 0.000 claims 2
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- 238000009472 formulation Methods 0.000 description 4
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 3
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
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- 150000001298 alcohols Chemical class 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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- GKMQWTVAAMITHR-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O.CCC(C)O GKMQWTVAAMITHR-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- QVQGTNFYPJQJNM-UHFFFAOYSA-N dicyclohexylmethanamine Chemical compound C1CCCCC1C(N)C1CCCCC1 QVQGTNFYPJQJNM-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- NVAHZHOCRQCUBY-UHFFFAOYSA-N ethyl 2,2-dimethyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)(C)C(C)=O NVAHZHOCRQCUBY-UHFFFAOYSA-N 0.000 description 1
- CIVBBCZFELVGRL-UHFFFAOYSA-N ethyl 2-[2-(4-chlorophenoxy)-2-imidazol-1-ylacetyl]-2-methylhexanoate Chemical compound C1=CN=CN1C(C(=O)C(C)(C(=O)OCC)CCCC)OC1=CC=C(Cl)C=C1 CIVBBCZFELVGRL-UHFFFAOYSA-N 0.000 description 1
- FNYOWFAFTAIYJA-UHFFFAOYSA-N ethyl 2-[2-bromo-2-(4-chlorophenoxy)acetyl]-2-methylpentanoate Chemical compound CCOC(=O)C(C)(CCC)C(=O)C(Br)OC1=CC=C(Cl)C=C1 FNYOWFAFTAIYJA-UHFFFAOYSA-N 0.000 description 1
- HFOAIZDEIGDHSV-UHFFFAOYSA-N ethyl 4-(4-bromophenoxy)-4-imidazol-1-yl-2,2-dimethyl-3-oxobutanoate Chemical compound C1=CN=CN1C(C(=O)C(C)(C)C(=O)OCC)OC1=CC=C(Br)C=C1 HFOAIZDEIGDHSV-UHFFFAOYSA-N 0.000 description 1
- QJWAXBIEFREGHZ-UHFFFAOYSA-N ethyl 4-(4-chlorophenoxy)-2,2-dimethyl-3-oxo-4-(1,2,4-triazol-1-yl)butanoate Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C(=O)OCC)OC1=CC=C(Cl)C=C1 QJWAXBIEFREGHZ-UHFFFAOYSA-N 0.000 description 1
- FPASGAFVNIAGEZ-UHFFFAOYSA-N ethyl 4-(4-chlorophenoxy)-2,2-dimethyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)(C)C(=O)COC1=CC=C(Cl)C=C1 FPASGAFVNIAGEZ-UHFFFAOYSA-N 0.000 description 1
- UFHWPMKFZCGMSM-UHFFFAOYSA-N ethyl 4-(4-chlorophenoxy)-4-imidazol-1-yl-2,2-dimethyl-3-oxobutanoate Chemical compound C1=CN=CN1C(C(=O)C(C)(C)C(=O)OCC)OC1=CC=C(Cl)C=C1 UFHWPMKFZCGMSM-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 230000004720 fertilization Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- SPNUOWANWHGNHD-UHFFFAOYSA-N methyl 4-bromo-4-(4-chlorophenoxy)-2,2-dimethyl-3-oxobutanoate Chemical compound COC(=O)C(C)(C)C(=O)C(Br)OC1=CC=C(Cl)C=C1 SPNUOWANWHGNHD-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical group C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- NFLAIYFPVYARNF-UHFFFAOYSA-N propan-2-yl 4-bromo-4-(4-chlorophenoxy)-2,2-dimethyl-3-oxobutanoate Chemical compound CC(C)OC(=O)C(C)(C)C(=O)C(Br)OC1=CC=C(Cl)C=C1 NFLAIYFPVYARNF-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- OWWWINQMSXUHJT-UHFFFAOYSA-N propyl 4-bromo-4-(4-chlorophenoxy)-2,2-dimethyl-3-oxobutanoate Chemical compound CCCOC(=O)C(C)(C)C(=O)C(Br)OC1=CC=C(Cl)C=C1 OWWWINQMSXUHJT-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene 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
-
- 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
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762635663 DE2635663A1 (de) | 1976-08-07 | 1976-08-07 | Azolyl-carbonsaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2635663.8 | 1977-03-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5321163A JPS5321163A (en) | 1978-02-27 |
| JPS6026110B2 true JPS6026110B2 (ja) | 1985-06-21 |
Family
ID=5984990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52093448A Expired JPS6026110B2 (ja) | 1976-08-07 | 1977-08-05 | 新規アゾリル−カルボン酸誘導体，その製造方法およびそれを有効成分として含有する殺菌剤組成物 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4331674A (en, 2012) |
| JP (1) | JPS6026110B2 (en, 2012) |
| AT (1) | AT358872B (en, 2012) |
| AU (1) | AU512557B2 (en, 2012) |
| BE (1) | BE857519A (en, 2012) |
| BR (1) | BR7705203A (en, 2012) |
| CA (1) | CA1092130A (en, 2012) |
| CH (1) | CH631710A5 (en, 2012) |
| CS (1) | CS194815B2 (en, 2012) |
| DD (1) | DD133391A5 (en, 2012) |
| DE (1) | DE2635663A1 (en, 2012) |
| DK (1) | DK150595C (en, 2012) |
| EG (1) | EG12805A (en, 2012) |
| FI (1) | FI772360A7 (en, 2012) |
| FR (1) | FR2360579A1 (en, 2012) |
| GB (1) | GB1532140A (en, 2012) |
| HU (1) | HU177167B (en, 2012) |
| IL (1) | IL52663A (en, 2012) |
| IT (1) | IT1085152B (en, 2012) |
| NL (1) | NL7708658A (en, 2012) |
| NZ (1) | NZ184848A (en, 2012) |
| PL (1) | PL103472B1 (en, 2012) |
| PT (1) | PT66886B (en, 2012) |
| SE (1) | SE7708895L (en, 2012) |
| TR (1) | TR19257A (en, 2012) |
| ZA (1) | ZA774737B (en, 2012) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3721022A (en) * | 1971-01-15 | 1973-03-20 | J Mercorelli | Design device |
| EP0002331A3 (en) * | 1977-12-07 | 1979-06-27 | Imperial Chemical Industries Plc | Imidazole and triazole compounds, fungicidal and plant growth regulating compositions, method of combating fungal infections in plants and method of regulating plant growth |
| DE2811919A1 (de) * | 1978-03-18 | 1979-09-27 | Bayer Ag | Acylierte 1-azolyl-2-hydroxy-butan- derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2827968A1 (de) * | 1978-06-26 | 1980-01-10 | Bayer Ag | Sulfenylierte carbamoyl-triazolyl- o,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2846038A1 (de) * | 1978-10-23 | 1980-05-08 | Basf Ag | 1,2,4-triazolderivate, ihre herstellung und verwendung |
| DE3021551A1 (de) * | 1980-06-07 | 1981-12-24 | Bayer Ag, 5090 Leverkusen | 4-substituierte 1-azolyl-1-phenoxy-3,3-dimethyl-butan-2-one und -ole, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| EP0046633A1 (en) * | 1980-08-22 | 1982-03-03 | Imperial Chemical Industries Plc | Heterocyclic compounds useful as pesticides and processes for making them |
| DE3032326A1 (de) | 1980-08-27 | 1982-04-08 | Bayer Ag, 5090 Leverkusen | Azolylalkyl-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| JPS5758671A (en) * | 1980-09-25 | 1982-04-08 | Ishihara Sangyo Kaisha Ltd | Phenoxyalkylazole type compound and agricultural and gardening fungicide comprising it |
| AR228764A1 (es) * | 1980-12-20 | 1983-04-15 | Bayer Ag | 1-azolil-3,3-dimetilalcan(c3-4)-2-onas y-2-oles,sustituidos,procedimiento para su produccion y composiciones protectoras de plantas fungicidas y reguladoras del crecimiento de las plantas a base de dichos compuestos |
| GB2104065B (en) * | 1981-06-04 | 1985-11-06 | Ciba Geigy Ag | Heterocyclyl-substituted mandelic acid compounds and mandelonitriles and their use for combating microorganisms |
| DE3200414A1 (de) * | 1982-01-09 | 1983-07-21 | Bayer Ag, 5090 Leverkusen | Azolyl-thioether-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und pflanzenwachstumsregulatoren |
| US4517194A (en) * | 1982-06-25 | 1985-05-14 | Ciba-Geigy Corporation | Azolylmandelic acid derivatives and use thereof for controlling microorganisms |
| US4584008A (en) * | 1982-07-14 | 1986-04-22 | Chevron Research Company | Aldol adducts containing triazole groups |
| PH19347A (en) * | 1982-09-30 | 1986-04-02 | Pfizer | Triazole derivatives,pharmaceutical composition containing same and method of use thereof |
| DE3313941A1 (de) * | 1983-04-15 | 1984-10-18 | Schering AG, 1000 Berlin und 4709 Bergkamen | 4-azolyl-pentannitrile, verfahren zur herstellung dieser verbundungen sowie diese enthaltende biozide mittel |
| GB8322983D0 (en) * | 1983-08-26 | 1983-09-28 | Pfizer Ltd | Triazole antifungal agents |
| DE3508909A1 (de) * | 1985-03-13 | 1986-09-18 | Bayer Ag, 5090 Leverkusen | Piperazinylmethyl-1,2,4-triazolylmethyl-carbinole |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH531516A (de) * | 1969-05-21 | 1972-12-15 | Bayer Ag | Verfahren zur Herstellung neuer Phenylimidazolyl-fettsäure-derivate |
| DE2105490C3 (de) * | 1971-02-05 | 1979-06-13 | Bayer Ag, 5090 Leverkusen | 1 -Imidazolylketonderivate |
| US4036966A (en) * | 1972-09-26 | 1977-07-19 | Bayer Aktiengesellschaft | 1,2,4-Triazole antimycotic compositions and use thereof |
| DE2324010C3 (de) * | 1973-05-12 | 1981-10-08 | Bayer Ag, 5090 Leverkusen | 1-Substituierte 2-Triazolyl-2-phenoxyäthanol-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Pilzen |
| DE2423987C2 (de) * | 1974-05-17 | 1986-01-16 | Bayer Ag, 5090 Leverkusen | Metallkomplexe von Azolyläthern, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
| DE2455955A1 (de) * | 1974-11-27 | 1976-08-12 | Bayer Ag | Fungizide mittel |
| DE2455953A1 (de) * | 1974-11-27 | 1976-08-12 | Bayer Ag | Fungizide mittel |
-
1976
- 1976-08-07 DE DE19762635663 patent/DE2635663A1/de active Granted
-
1977
- 1977-07-27 US US05/819,533 patent/US4331674A/en not_active Expired - Lifetime
- 1977-08-02 GB GB32386/77A patent/GB1532140A/en not_active Expired
- 1977-08-02 CH CH951077A patent/CH631710A5/de not_active IP Right Cessation
- 1977-08-03 DD DD77200422A patent/DD133391A5/xx unknown
- 1977-08-03 EG EG457/77A patent/EG12805A/xx active
- 1977-08-04 NL NL7708658A patent/NL7708658A/xx not_active Application Discontinuation
- 1977-08-04 SE SE7708895A patent/SE7708895L/xx unknown
- 1977-08-04 FI FI772360A patent/FI772360A7/fi not_active Application Discontinuation
- 1977-08-04 IL IL7752663A patent/IL52663A/xx unknown
- 1977-08-04 PT PT66886A patent/PT66886B/pt unknown
- 1977-08-04 NZ NZ184848A patent/NZ184848A/xx unknown
- 1977-08-05 JP JP52093448A patent/JPS6026110B2/ja not_active Expired
- 1977-08-05 IT IT26562/77A patent/IT1085152B/it active
- 1977-08-05 TR TR19257A patent/TR19257A/xx unknown
- 1977-08-05 PL PL1977200093A patent/PL103472B1/pl unknown
- 1977-08-05 HU HU77BA3566A patent/HU177167B/hu unknown
- 1977-08-05 CA CA284,241A patent/CA1092130A/en not_active Expired
- 1977-08-05 BE BE179932A patent/BE857519A/xx not_active IP Right Cessation
- 1977-08-05 BR BR7705203A patent/BR7705203A/pt unknown
- 1977-08-05 DK DK352377A patent/DK150595C/da not_active IP Right Cessation
- 1977-08-05 FR FR7724262A patent/FR2360579A1/fr active Granted
- 1977-08-05 CS CS775201A patent/CS194815B2/cs unknown
- 1977-08-05 AU AU27649/77A patent/AU512557B2/en not_active Expired
- 1977-08-05 AT AT576477A patent/AT358872B/de not_active IP Right Cessation
- 1977-08-05 ZA ZA00774737A patent/ZA774737B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA774737B (en) | 1978-06-28 |
| BR7705203A (pt) | 1978-06-06 |
| CS194815B2 (en) | 1979-12-31 |
| PT66886B (en) | 1979-01-25 |
| IL52663A0 (en) | 1977-10-31 |
| DD133391A5 (de) | 1979-01-03 |
| DK150595C (da) | 1987-11-02 |
| FR2360579B1 (en, 2012) | 1981-01-09 |
| NZ184848A (en) | 1978-12-18 |
| AU512557B2 (en) | 1980-10-16 |
| DE2635663A1 (de) | 1978-02-09 |
| SE7708895L (sv) | 1978-02-08 |
| IT1085152B (it) | 1985-05-28 |
| IL52663A (en) | 1981-02-27 |
| GB1532140A (en) | 1978-11-15 |
| PT66886A (en) | 1977-09-01 |
| FR2360579A1 (fr) | 1978-03-03 |
| US4331674A (en) | 1982-05-25 |
| CH631710A5 (de) | 1982-08-31 |
| AT358872B (de) | 1980-10-10 |
| BE857519A (fr) | 1978-02-06 |
| PL200093A1 (pl) | 1978-04-10 |
| NL7708658A (nl) | 1978-02-09 |
| AU2764977A (en) | 1979-02-15 |
| DE2635663C2 (en, 2012) | 1988-08-11 |
| HU177167B (en) | 1981-08-28 |
| ATA576477A (de) | 1980-02-15 |
| PL103472B1 (pl) | 1979-06-30 |
| EG12805A (en) | 1979-09-30 |
| TR19257A (tr) | 1978-08-15 |
| DK352377A (da) | 1978-02-08 |
| DK150595B (da) | 1987-04-06 |
| CA1092130A (en) | 1980-12-23 |
| JPS5321163A (en) | 1978-02-27 |
| FI772360A7 (en, 2012) | 1978-02-08 |
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