FR2631624A1 - Phenylalcoylformamides substitues et composition fongicide les contenant - Google Patents
Phenylalcoylformamides substitues et composition fongicide les contenant Download PDFInfo
- Publication number
- FR2631624A1 FR2631624A1 FR8906515A FR8906515A FR2631624A1 FR 2631624 A1 FR2631624 A1 FR 2631624A1 FR 8906515 A FR8906515 A FR 8906515A FR 8906515 A FR8906515 A FR 8906515A FR 2631624 A1 FR2631624 A1 FR 2631624A1
- Authority
- FR
- France
- Prior art keywords
- fungicidal
- formamido
- substituted
- compounds
- product
- 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.)
- Withdrawn
Links
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 38
- 239000000203 mixture Substances 0.000 title claims abstract description 23
- 239000000417 fungicide Substances 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 229910052801 chlorine Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000460 chlorine Chemical group 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- -1 2,4-dichlorophenoxy Chemical group 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 13
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 10
- 239000004563 wettable powder Substances 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims 2
- 241001331845 Equus asinus x caballus Species 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 235000013339 cereals Nutrition 0.000 abstract description 5
- 201000010099 disease Diseases 0.000 abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 5
- 239000000047 product Substances 0.000 description 32
- 238000012360 testing method Methods 0.000 description 18
- 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 11
- 239000005846 Triadimenol Substances 0.000 description 10
- 241000209219 Hordeum Species 0.000 description 8
- 235000007340 Hordeum vulgare Nutrition 0.000 description 8
- 241000209140 Triticum Species 0.000 description 8
- 235000021307 Triticum Nutrition 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000000034 method Methods 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
- 241000233866 Fungi Species 0.000 description 4
- 244000062793 Sorghum vulgare Species 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000012678 infectious agent Substances 0.000 description 4
- 235000019713 millet Nutrition 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000190150 Bipolaris sorokiniana Species 0.000 description 2
- 241000736122 Parastagonospora nodorum Species 0.000 description 2
- 239000005822 Propiconazole Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 150000002344 gold compounds Chemical class 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JJHMFMLNPPNLAL-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethylbutan-2-ol Chemical compound CC(C)(C)C(O)COC1=CC=C(Cl)C=C1 JJHMFMLNPPNLAL-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- DTCCTIQRPGSLPT-UHFFFAOYSA-N 2-pentenal Chemical compound CCC=CC=O DTCCTIQRPGSLPT-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 244000205754 Colocasia esculenta Species 0.000 description 1
- 235000006481 Colocasia esculenta Nutrition 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241001517923 Douglasiidae Species 0.000 description 1
- 241000223195 Fusarium graminearum Species 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- 108010034145 Helminth Proteins Proteins 0.000 description 1
- 241001459558 Monographella nivalis Species 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 241001558145 Mucor sp. Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241000287531 Psittacidae Species 0.000 description 1
- 241000520648 Pyrenophora teres Species 0.000 description 1
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 1
- 241001533598 Septoria Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 230000005764 inhibitory process Effects 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
- 230000003902 lesion Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QOCXLGWYHYULLD-UHFFFAOYSA-N n-(3,3-dimethylbutyl)formamide Chemical compound CC(C)(C)CCNC=O QOCXLGWYHYULLD-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect 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 |
|---|---|
| FR2631624A1 true FR2631624A1 (fr) | 1989-11-24 |
Family
ID=26666163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8906515A Withdrawn FR2631624A1 (fr) | 1988-05-18 | 1989-05-18 | Phenylalcoylformamides substitues et composition fongicide les contenant |
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 |
Citations (7)
| 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 |
| FR2055413A5 (enrdf_load_stackoverflow) * | 1969-07-21 | 1971-05-07 | Boehringer Sohn Ingelheim | |
| US3835184A (en) * | 1970-07-15 | 1974-09-10 | Boehringer Sohn Ingelheim | Formamide derivatives |
| 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 |
| EP0094539B1 (de) * | 1982-05-18 | 1985-08-21 | Bayer Ag | Halogenpropargylformamide |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4915768B1 (enrdf_load_stackoverflow) * | 1970-09-04 | 1974-04-17 | ||
| DE2939350A1 (de) * | 1979-09-28 | 1981-04-30 | Basf Ag, 6700 Ludwigshafen | Glykoletheranilide, verfahren zu ihrer herstellung und diese enthaltende fungizide |
-
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
Patent Citations (7)
| 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 |
| FR2055413A5 (enrdf_load_stackoverflow) * | 1969-07-21 | 1971-05-07 | Boehringer Sohn Ingelheim | |
| US3835184A (en) * | 1970-07-15 | 1974-09-10 | Boehringer Sohn Ingelheim | Formamide derivatives |
| 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 |
| EP0094539B1 (de) * | 1982-05-18 | 1985-08-21 | Bayer Ag | Halogenpropargylformamide |
Also Published As
| Publication number | Publication date |
|---|---|
| HUT49982A (en) | 1989-12-28 |
| CH676597A5 (enrdf_load_stackoverflow) | 1991-02-15 |
| 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 |
| PL153872B1 (en) | 1991-06-28 |
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