CA1174866A - Plant growth regulating cyano-phenyl-acetamide derivatives - Google Patents
Plant growth regulating cyano-phenyl-acetamide derivativesInfo
- Publication number
- CA1174866A CA1174866A CA000371912A CA371912A CA1174866A CA 1174866 A CA1174866 A CA 1174866A CA 000371912 A CA000371912 A CA 000371912A CA 371912 A CA371912 A CA 371912A CA 1174866 A CA1174866 A CA 1174866A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- group
- plant growth
- hydrogen
- plants
- 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
- 230000008635 plant growth Effects 0.000 title claims description 22
- 230000001105 regulatory effect Effects 0.000 title claims description 17
- DJEAUFPPXDHFCN-UHFFFAOYSA-N 2-cyano-2-phenylacetamide Chemical class NC(=O)C(C#N)C1=CC=CC=C1 DJEAUFPPXDHFCN-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000013543 active substance Substances 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 14
- -1 morpholino, pyrrolidino, piperidino Chemical group 0.000 claims description 14
- 239000007921 spray Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000002689 soil Substances 0.000 claims description 10
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 8
- 239000004563 wettable powder Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 239000007888 film coating Substances 0.000 claims description 6
- 238000009501 film coating Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- QKSRTQXCXWMMLG-UHFFFAOYSA-N 2-cyano-2-phenylbutanamide Chemical compound CCC(C#N)(C(N)=O)C1=CC=CC=C1 QKSRTQXCXWMMLG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 239000002184 metal Substances 0.000 abstract 2
- 230000006641 stabilisation Effects 0.000 abstract 1
- 238000011105 stabilization Methods 0.000 abstract 1
- 235000013350 formula milk Nutrition 0.000 description 34
- 239000003795 chemical substances by application Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000126 substance Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 229910000514 dolomite Inorganic materials 0.000 description 8
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- 239000000843 powder Substances 0.000 description 8
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- 238000006243 chemical reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
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- 239000000080 wetting agent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XAYBZYXKFHHIHQ-UHFFFAOYSA-N 2-cyano-2-phenylbutanoyl chloride Chemical compound CCC(C#N)(C(Cl)=O)C1=CC=CC=C1 XAYBZYXKFHHIHQ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000005862 Whey Substances 0.000 description 3
- 102000007544 Whey Proteins Human genes 0.000 description 3
- 108010046377 Whey Proteins Proteins 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
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- 239000004576 sand Substances 0.000 description 3
- 230000004936 stimulating effect Effects 0.000 description 3
- PTXLMDGMBJFHGQ-UHFFFAOYSA-N 2-(morpholine-4-carbonyl)-2-phenylbutanenitrile Chemical compound C=1C=CC=CC=1C(C#N)(CC)C(=O)N1CCOCC1 PTXLMDGMBJFHGQ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000020551 Helianthus annuus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
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- 240000003768 Solanum lycopersicum Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 229940060038 chlorine Drugs 0.000 description 2
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- 150000002500 ions Chemical class 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
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- 239000012074 organic phase Substances 0.000 description 2
- 229910001562 pearlite Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- 229920006395 saturated elastomer Polymers 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
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- HYFRWPLUNOFOCF-UHFFFAOYSA-N 2-cyano-2-phenylpropanoyl chloride Chemical compound N#CC(C)(C(Cl)=O)C1=CC=CC=C1 HYFRWPLUNOFOCF-UHFFFAOYSA-N 0.000 description 1
- FGCWOPKPCQWFHJ-UHFFFAOYSA-N 2-cyano-n,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C#N)C(=O)NC1=CC=CC=C1 FGCWOPKPCQWFHJ-UHFFFAOYSA-N 0.000 description 1
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- 235000009973 maize Nutrition 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- VVAHBRVAXFGEPI-UHFFFAOYSA-N methyl 2-cyano-2-phenylacetate Chemical compound COC(=O)C(C#N)C1=CC=CC=C1 VVAHBRVAXFGEPI-UHFFFAOYSA-N 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- A01N37/34—Nitriles
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU464/80 | 1980-02-29 | ||
| HU80464A HU185876B (en) | 1980-02-29 | 1980-02-29 | Composition for controlling growth of plants and process for producing the active agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1174866A true CA1174866A (en) | 1984-09-25 |
Family
ID=10949708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000371912A Expired CA1174866A (en) | 1980-02-29 | 1981-02-27 | Plant growth regulating cyano-phenyl-acetamide derivatives |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4740228A (en, 2012) |
| JP (1) | JPS56135407A (en, 2012) |
| AT (1) | AT371667B (en, 2012) |
| AU (1) | AU544732B2 (en, 2012) |
| BE (1) | BE887683A (en, 2012) |
| CA (1) | CA1174866A (en, 2012) |
| CH (1) | CH646945A5 (en, 2012) |
| CS (1) | CS222243B2 (en, 2012) |
| DE (1) | DE3107629C2 (en, 2012) |
| DK (1) | DK92181A (en, 2012) |
| ES (1) | ES8201538A1 (en, 2012) |
| FI (1) | FI65358C (en, 2012) |
| FR (2) | FR2483176A1 (en, 2012) |
| GB (1) | GB2072645B (en, 2012) |
| GR (1) | GR74096B (en, 2012) |
| HU (1) | HU185876B (en, 2012) |
| IL (1) | IL62228A (en, 2012) |
| IT (1) | IT1210996B (en, 2012) |
| NL (1) | NL8100962A (en, 2012) |
| PL (1) | PL128639B1 (en, 2012) |
| SE (1) | SE460249B (en, 2012) |
| SU (3) | SU1478991A3 (en, 2012) |
| YU (1) | YU41971B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3265935A (en) * | 1963-08-30 | 1966-08-09 | Aerojet General Co | Modular chassis |
| US3751127A (en) * | 1970-09-10 | 1973-08-07 | Telecommunication Technology I | Modular instrument housing |
| SE7311226L (en, 2012) * | 1973-08-17 | 1975-02-18 | Expo Nord Ab | |
| US4162113A (en) * | 1977-05-09 | 1979-07-24 | Piero Pallavicini | Composite modular furniture |
| JPH01270020A (ja) * | 1988-04-22 | 1989-10-27 | Ryuichi Hayashi | 永久磁石を用いた光スイッチ |
| US5130456A (en) * | 1989-10-06 | 1992-07-14 | Virginia Tech Intellectual Properties, Inc. | Bis(reissert compounds) from reaction of monoaldehyde, monoamine and diacid halide |
| US5041601A (en) * | 1989-10-06 | 1991-08-20 | Virginia Tech Intellectual Properties, Inc. | Preparation of acyclic bis (reissert compounds) |
| DE59105562D1 (de) * | 1990-06-28 | 1995-06-29 | Ciba Geigy Ag | Alpha-Carbonylphenylacetonitrilderivate als Stabilisatoren für organische Materialien. |
| DE50002073D1 (de) | 1999-03-02 | 2003-06-12 | Basf Ag | Verwendung von phenylessigsaüreamide als pflanzenschutzmittel mit herbizider und fungizider wirkung |
| US6462076B2 (en) * | 2000-06-14 | 2002-10-08 | Hoffmann-La Roche Inc. | Beta-amino acid nitrile derivatives as cathepsin K inhibitors |
| JP4928276B2 (ja) * | 2007-01-11 | 2012-05-09 | オタリ株式会社 | フィルム除去装置 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2412510A (en) * | 1944-06-02 | 1946-12-10 | American Chem Paint Co | Methods and compositions for killing weeds |
| US3020146A (en) * | 1958-09-22 | 1962-02-06 | Velsicol Chemical Corp | Method of destroying undesirable plants |
| DE1542777C3 (de) * | 1965-04-17 | 1978-12-07 | Bayer Ag, 5090 Leverkusen | a-ChIor-ß-(4-chlorphenyl) propionsäruemethylester und Herbizide mit einem Gehalt an einem cx-Chlorß-phenylpropionsäruederivat |
| DE1542822A1 (de) * | 1966-03-10 | 1970-03-26 | Basf Ag | Selektive Herbizide |
| JPS5353617A (en) * | 1976-10-23 | 1978-05-16 | Tanabe Seiyaku Co Ltd | Alpha-isocyano fatty acid amide derivatives and process for preparation of thesame |
| DE2751782A1 (de) * | 1977-11-19 | 1979-05-23 | Bayer Ag | Mittel zur regulierung des pflanzenwachstums |
| US4313754A (en) * | 1978-05-05 | 1982-02-02 | American Cyanamid Company | Polysubstituted butanoic acids, esters and derivatives thereof utilizing the same as herbicides |
| DE2842639A1 (de) * | 1978-09-29 | 1980-04-10 | Bayer Ag | Alpha -isocyano-carbonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatoren |
-
1980
- 1980-02-29 HU HU80464A patent/HU185876B/hu not_active IP Right Cessation
-
1981
- 1981-02-26 BE BE1/10151A patent/BE887683A/fr not_active IP Right Cessation
- 1981-02-26 CH CH129281A patent/CH646945A5/de not_active IP Right Cessation
- 1981-02-27 CA CA000371912A patent/CA1174866A/en not_active Expired
- 1981-02-27 CS CS811442A patent/CS222243B2/cs unknown
- 1981-02-27 IL IL62228A patent/IL62228A/xx unknown
- 1981-02-27 YU YU500/81A patent/YU41971B/xx unknown
- 1981-02-27 SE SE8101304A patent/SE460249B/sv not_active IP Right Cessation
- 1981-02-27 AT AT0091581A patent/AT371667B/de not_active IP Right Cessation
- 1981-02-27 AU AU67920/81A patent/AU544732B2/en not_active Ceased
- 1981-02-27 IT IT8120025A patent/IT1210996B/it active
- 1981-02-27 NL NL8100962A patent/NL8100962A/nl not_active Application Discontinuation
- 1981-02-27 FI FI810629A patent/FI65358C/fi not_active IP Right Cessation
- 1981-02-27 FR FR8103917A patent/FR2483176A1/fr active Granted
- 1981-02-27 DE DE3107629A patent/DE3107629C2/de not_active Expired
- 1981-02-27 GB GB8106327A patent/GB2072645B/en not_active Expired
- 1981-02-27 SU SU813325354A patent/SU1478991A3/ru active
- 1981-02-27 GR GR64254A patent/GR74096B/el unknown
- 1981-02-27 DK DK92181A patent/DK92181A/da not_active Application Discontinuation
- 1981-02-27 PL PL1981229912A patent/PL128639B1/pl unknown
- 1981-02-28 JP JP2929881A patent/JPS56135407A/ja active Granted
- 1981-02-28 ES ES499940A patent/ES8201538A1/es not_active Expired
- 1981-11-17 FR FR8121446A patent/FR2491061A1/fr active Granted
-
1982
- 1982-09-20 SU SU823493198A patent/SU1318152A3/ru active
- 1982-09-20 SU SU823491803A patent/SU1389677A3/ru active
-
1984
- 1984-01-10 US US06/569,594 patent/US4740228A/en not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |