CH676597A5 - - Google Patents
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- Publication number
- CH676597A5 CH676597A5 CH28090A CH28090A CH676597A5 CH 676597 A5 CH676597 A5 CH 676597A5 CH 28090 A CH28090 A CH 28090A CH 28090 A CH28090 A CH 28090A CH 676597 A5 CH676597 A5 CH 676597A5
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
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- subhead col
- subhead
- formamido
- Prior art date
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- 230000000855 fungicidal effect Effects 0.000 claims abstract description 46
- 239000000417 fungicide Substances 0.000 claims description 32
- 239000004480 active ingredient Substances 0.000 claims description 21
- 239000004563 wettable powder Substances 0.000 claims description 9
- VATSHOWYLSHEDJ-UHFFFAOYSA-N n-[1-(2,4-dichlorophenyl)-4,4-dimethylpent-1-en-3-yl]formamide Chemical compound O=CNC(C(C)(C)C)C=CC1=CC=C(Cl)C=C1Cl VATSHOWYLSHEDJ-UHFFFAOYSA-N 0.000 claims description 8
- -1 1- (2,4-dichlorophenyl) -2-formamido-3,3-dimethylbutane Chemical compound 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 abstract description 32
- 150000001875 compounds Chemical class 0.000 abstract description 25
- 239000013543 active substance Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 18
- 239000005846 Triadimenol Substances 0.000 description 13
- 201000010099 disease Diseases 0.000 description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 13
- 241000209219 Hordeum Species 0.000 description 10
- 235000007340 Hordeum vulgare Nutrition 0.000 description 10
- ZVHHCHZVHJMAGW-UHFFFAOYSA-N N-[1-(2,4-dichlorophenoxy)-3,3-dimethylbutan-2-yl]formamide Chemical compound CC(C)(C)C(COC1=C(Cl)C=C(Cl)C=C1)NC=O ZVHHCHZVHJMAGW-UHFFFAOYSA-N 0.000 description 10
- 241000209140 Triticum Species 0.000 description 10
- 235000021307 Triticum Nutrition 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 6
- 230000035784 germination Effects 0.000 description 6
- 244000052769 pathogen Species 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 244000062793 Sorghum vulgare Species 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000002538 fungal effect Effects 0.000 description 5
- 238000011835 investigation Methods 0.000 description 5
- 235000019713 millet Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- NVHGPUNRDSHVIF-UHFFFAOYSA-N N-[1-(4-chlorophenyl)-4,4-dimethylpent-1-en-3-yl]formamide Chemical compound ClC1=CC=C(C=C1)C=CC(C(C)(C)C)NC=O NVHGPUNRDSHVIF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 3
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000228245 Aspergillus niger Species 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 241000223195 Fusarium graminearum Species 0.000 description 2
- 241000223221 Fusarium oxysporum Species 0.000 description 2
- 241000736122 Parastagonospora nodorum Species 0.000 description 2
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 2
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004362 fungal culture Methods 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- LXJZYHPGRKBVGF-RMKNXTFCSA-N (e)-1-(4-chlorophenyl)-4,4-dimethylpent-1-en-3-one Chemical compound CC(C)(C)C(=O)\C=C\C1=CC=C(Cl)C=C1 LXJZYHPGRKBVGF-RMKNXTFCSA-N 0.000 description 1
- QGSJVMUQCRYUIZ-UHFFFAOYSA-N 1-(2,4-dichlorophenoxy)-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)COC1=CC=C(Cl)C=C1Cl QGSJVMUQCRYUIZ-UHFFFAOYSA-N 0.000 description 1
- WISVKXCNQOLCJL-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)COC1=CC=C(Cl)C=C1 WISVKXCNQOLCJL-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000190150 Bipolaris sorokiniana Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 239000005746 Carboxin Substances 0.000 description 1
- MMHBOANOTOQIMO-UHFFFAOYSA-N ClC1=CC=C(OCC(C(C)(C)C)NC=O)C=C1 Chemical compound ClC1=CC=C(OCC(C(C)(C)C)NC=O)C=C1 MMHBOANOTOQIMO-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241001459558 Monographella nivalis Species 0.000 description 1
- 241001558145 Mucor sp. Species 0.000 description 1
- 241000228168 Penicillium sp. Species 0.000 description 1
- 241000520648 Pyrenophora teres Species 0.000 description 1
- 241000872198 Serjania polyphylla Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241001123668 Verticillium dahliae Species 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000000543 intermediate 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
- C07C233/13—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU884427664A RU1775395C (ru) | 1988-05-18 | 1988-05-18 | 1-(2,4-Дихлорфенокси)-2-формамидо-3,3-диметилбутан, обладающий фунгицидной активностью |
| SU884443133A RU1775394C (ru) | 1988-05-18 | 1988-05-18 | 1-(4-Хлор-или 2,4-дихлорфенил)-3-формамидо-4,4-диметилпентены-1, обладающие фунгицидной активностью |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH676597A5 true CH676597A5 (enrdf_load_stackoverflow) | 1991-02-15 |
Family
ID=26666163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH28090A CH676597A5 (enrdf_load_stackoverflow) | 1988-05-18 | 1989-02-17 |
Country Status (11)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110407681B (zh) * | 2019-08-12 | 2023-05-02 | 海南大学 | 一种脱氢姜酮衍生物、其制备方法及应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2011790A (en) * | 1934-03-13 | 1935-08-20 | Gordon A Alles | 1-(paramethoxyphenyl)-2-formylaminopropanes and method of preparing same |
| US2368073A (en) * | 1943-04-12 | 1945-01-23 | Commercial Solvents Corp | Process for preparing hydroxy amides |
| AT296242B (de) * | 1969-07-21 | 1972-02-10 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von neuen Formamidderivaten |
| US3835184A (en) * | 1970-07-15 | 1974-09-10 | Boehringer Sohn Ingelheim | Formamide derivatives |
| JPS4915768B1 (enrdf_load_stackoverflow) * | 1970-09-04 | 1974-04-17 | ||
| 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 |
| US4160838A (en) * | 1977-06-02 | 1979-07-10 | Janssen Pharmaceutica N.V. | Antimicrobial and plant-growth-regulating triazole derivatives |
| DE2939350A1 (de) * | 1979-09-28 | 1981-04-30 | Basf Ag, 6700 Ludwigshafen | Glykoletheranilide, verfahren zu ihrer herstellung und diese enthaltende fungizide |
| DE3236522A1 (de) * | 1982-05-18 | 1983-11-24 | Bayer Ag, 5090 Leverkusen | Halogenpropargylformamide |
-
1989
- 1989-02-17 CH CH28090A patent/CH676597A5/de not_active IP Right Cessation
- 1989-02-17 AU AU33624/89A patent/AU3362489A/en not_active Abandoned
- 1989-02-17 JP JP1503855A patent/JPH02504281A/ja active Pending
- 1989-02-17 NL NL8920256A patent/NL8920256A/nl not_active Application Discontinuation
- 1989-02-17 WO PCT/SU1989/000044 patent/WO1989011472A1/ru active Application Filing
- 1989-05-17 PL PL27949089A patent/PL153872B1/pl unknown
- 1989-05-17 HU HU245789A patent/HUT49982A/hu unknown
- 1989-05-18 RO RO13980489A patent/RO103770B1/ro unknown
- 1989-05-18 CN CN 89104607 patent/CN1038276A/zh active Pending
- 1989-05-18 FR FR8906515A patent/FR2631624A1/fr not_active Withdrawn
-
1990
- 1990-01-17 GB GB9001044A patent/GB2229437A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| HUT49982A (en) | 1989-12-28 |
| GB2229437A (en) | 1990-09-26 |
| AU3362489A (en) | 1989-12-12 |
| RO103770B1 (en) | 1993-04-15 |
| GB9001044D0 (en) | 1990-07-11 |
| WO1989011472A1 (en) | 1989-11-30 |
| PL279490A1 (en) | 1990-01-08 |
| CN1038276A (zh) | 1989-12-27 |
| JPH02504281A (ja) | 1990-12-06 |
| NL8920256A (nl) | 1990-04-02 |
| FR2631624A1 (fr) | 1989-11-24 |
| PL153872B1 (en) | 1991-06-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |