HU185876B - Composition for controlling growth of plants and process for producing the active agent - Google Patents
Composition for controlling growth of plants and process for producing the active agent Download PDFInfo
- Publication number
- HU185876B HU185876B HU80464A HU46480A HU185876B HU 185876 B HU185876 B HU 185876B HU 80464 A HU80464 A HU 80464A HU 46480 A HU46480 A HU 46480A HU 185876 B HU185876 B HU 185876B
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- hydrogen
- formula
- phenyl
- group
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims description 26
- 230000008635 plant growth Effects 0.000 title abstract description 17
- 239000013543 active substance Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 239000001257 hydrogen Substances 0.000 claims abstract description 33
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 17
- -1 morpholino, pyrrolidino, piperidino Chemical group 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 3
- 239000007787 solid Substances 0.000 claims abstract description 3
- 230000002152 alkylating effect Effects 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 239000004480 active ingredient Substances 0.000 claims description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000000843 powder Substances 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000010459 dolomite Substances 0.000 claims description 8
- 229910000514 dolomite Inorganic materials 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000000460 chlorine Substances 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000005648 plant growth regulator Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- DKFPBXQCCCIWLC-UHFFFAOYSA-N 2-cyano-2-phenylacetic acid Chemical class OC(=O)C(C#N)C1=CC=CC=C1 DKFPBXQCCCIWLC-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 239000005862 Whey Substances 0.000 claims description 4
- 102000007544 Whey Proteins Human genes 0.000 claims description 4
- 108010046377 Whey Proteins Proteins 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 239000010451 perlite Substances 0.000 claims description 4
- 235000019362 perlite Nutrition 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 206010029897 Obsessive thoughts Diseases 0.000 claims description 3
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 2
- 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 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 239000002736 nonionic surfactant Substances 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims 2
- 229920000945 Amylopectin Polymers 0.000 claims 1
- 239000003945 anionic surfactant Substances 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 239000003093 cationic surfactant Substances 0.000 claims 1
- 239000003350 kerosene Substances 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 abstract description 8
- 239000004094 surface-active agent Substances 0.000 abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 abstract description 3
- 239000003085 diluting agent Substances 0.000 abstract description 3
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 abstract description 2
- 239000000654 additive Substances 0.000 abstract description 2
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- 239000000126 substance Substances 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 21
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- GXJQMKFJQFGQKV-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS(O)(=O)=O GXJQMKFJQFGQKV-KHPPLWFESA-N 0.000 description 5
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- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- DJEAUFPPXDHFCN-UHFFFAOYSA-N 2-cyano-2-phenylacetamide Chemical class NC(=O)C(C#N)C1=CC=CC=C1 DJEAUFPPXDHFCN-UHFFFAOYSA-N 0.000 description 3
- 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
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- PTXLMDGMBJFHGQ-UHFFFAOYSA-N 2-(morpholine-4-carbonyl)-2-phenylbutanenitrile Chemical group C=1C=CC=CC=1C(C#N)(CC)C(=O)N1CCOCC1 PTXLMDGMBJFHGQ-UHFFFAOYSA-N 0.000 description 2
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- 238000005119 centrifugation Methods 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012272 crop production Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 description 1
- 239000004062 cytokinin Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- VCJAUIYSQAXNGB-UHFFFAOYSA-N ethyl 2-cyano-2-phenylbutanoate Chemical compound CCOC(=O)C(CC)(C#N)C1=CC=CC=C1 VCJAUIYSQAXNGB-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003448 gibberellin Substances 0.000 description 1
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 235000019426 modified starch Nutrition 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
- 239000005445 natural material Substances 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 235000021231 nutrient uptake Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000002700 urine Anatomy 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
- 239000001993 wax Substances 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)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU80464A HU185876B (en) | 1980-02-29 | 1980-02-29 | Composition for controlling growth of plants and process for producing the active agent |
| CH129281A CH646945A5 (de) | 1980-02-29 | 1981-02-26 | Phenylessigsaeurederivate, deren herstellung und diese enthaltendes pflanzenwachstumsregulierendes mittel. |
| BE1/10151A BE887683A (fr) | 1980-02-29 | 1981-02-26 | Composes et compositions pour la regulation de la croissance des plantes et procede de preparation de ces composes et compositions |
| CA000371912A CA1174866A (en) | 1980-02-29 | 1981-02-27 | Plant growth regulating cyano-phenyl-acetamide derivatives |
| IT8120025A IT1210996B (it) | 1980-02-29 | 1981-02-27 | Composti e composizioni regolanti la crescita delle piante eprocedimento per la loro preparazione. |
| PL1981229912A PL128639B1 (en) | 1980-02-29 | 1981-02-27 | Plant growth control agent |
| CS811442A CS222243B2 (en) | 1980-02-29 | 1981-02-27 | Means for regulation fo the plant growth and method of preparation of the active agent |
| IL62228A IL62228A (en) | 1980-02-29 | 1981-02-27 | Plant growth regulating compositions comprising alpha-cyano-alpha-phenylalkan-amide derivatives |
| SU813325354A SU1478991A3 (ru) | 1980-02-29 | 1981-02-27 | Средство, регулирующее рост подсолнечника |
| AT0091581A AT371667B (de) | 1980-02-29 | 1981-02-27 | Pflanzenwachstumsregulierendes mittel |
| GB8106327A GB2072645B (en) | 1980-02-29 | 1981-02-27 | Plant growth regulating compounds and compositions and the preparation therof |
| NL8100962A NL8100962A (nl) | 1980-02-29 | 1981-02-27 | Plantengroei regelende verbindingen en preparaten en werkwijzen voor de bereiding daarvan. |
| AU67920/81A AU544732B2 (en) | 1980-02-29 | 1981-02-27 | Substituted benzylnitriles-amides as plant growth regulating compounds |
| DE3107629A DE3107629C2 (de) | 1980-02-29 | 1981-02-27 | 2-Cyan-2-phenylacetamide und diese enthaltende pflanzenwachstumsregulierende Mittel |
| YU500/81A YU41971B (en) | 1980-02-29 | 1981-02-27 | Process for obtaining alpna-cyanophenyl acetic acid derivatives |
| DK92181A DK92181A (da) | 1980-02-29 | 1981-02-27 | Plantevaekstregulerende midler fremgangsmaade til fremstilling heraf samt deres anvendelse |
| SE8101304A SE460249B (sv) | 1980-02-29 | 1981-02-27 | Blandning foer reglering av vaexters tillvaext innehaallande som aktiv substans 2-cyano-2-etyl-2-fenylaettiksyraamid och/eller 2-cyano-2-etyl-2-fenylaettiksyramorfolid, anvaendning daerav samt 2-cyano-2-etyl-2-fenylaettiksyramorfolid |
| FR8103917A FR2483176A1 (fr) | 1980-02-29 | 1981-02-27 | Composes et compositions pour la regulation de la croissance des plantes et procede de preparation de ces composes et compositions |
| GR64254A GR74096B (en, 2012) | 1980-02-29 | 1981-02-27 | |
| FI810629A FI65358C (fi) | 1980-02-29 | 1981-02-27 | Komposition foer reglering av vaexters tillvaext |
| JP2929881A JPS56135407A (en) | 1980-02-29 | 1981-02-28 | Plant growth regulant compound and composition |
| ES499940A ES8201538A1 (es) | 1980-02-29 | 1981-02-28 | Procedimiento para producir agentes reguladores del creci- miento de los vegetales |
| FR8121446A FR2491061A1 (fr) | 1980-02-29 | 1981-11-17 | Composes pour la regulation de la croissance des plantes et procede de preparation de ces composes |
| SU823493198A SU1318152A3 (ru) | 1980-02-29 | 1982-09-20 | Способ получени производных 2-циано-2-фенилуксусной кислоты |
| SU823491803A SU1389677A3 (ru) | 1980-02-29 | 1982-09-20 | Способ получени производных 2-циано-2-фенилуксусной кислоты |
| US06/569,594 US4740228A (en) | 1980-02-29 | 1984-01-10 | Plant growth regulating compounds and compositions and a process for the preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
|---|---|
| HU185876B true HU185876B (en) | 1985-04-28 |
Family
ID=10949708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU80464A HU185876B (en) | 1980-02-29 | 1980-02-29 | Composition for controlling growth of plants and process for producing the active agent |
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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| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |