HU184353B - Plant growth regulating composition containing bicyclo/2.2.1/ heptane derivative further process for preparing bicyclo/2.2.1/ heptane derivatives - Google Patents
Plant growth regulating composition containing bicyclo/2.2.1/ heptane derivative further process for preparing bicyclo/2.2.1/ heptane derivatives Download PDFInfo
- Publication number
- HU184353B HU184353B HU802774A HU277480A HU184353B HU 184353 B HU184353 B HU 184353B HU 802774 A HU802774 A HU 802774A HU 277480 A HU277480 A HU 277480A HU 184353 B HU184353 B HU 184353B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- group
- heptane
- active ingredient
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 53
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 title description 8
- 230000008635 plant growth Effects 0.000 title description 6
- 230000001105 regulatory effect Effects 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000004480 active ingredient Substances 0.000 claims abstract description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 239000005648 plant growth regulator Substances 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- -1 n-dodecyl Chemical group 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
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- 239000007921 spray Substances 0.000 claims description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000008096 xylene Substances 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
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- 239000004094 surface-active agent Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
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- 239000002904 solvent Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
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- 239000002736 nonionic surfactant Substances 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
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- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 4
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- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
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- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- UMRZSTCPUPJPOJ-UHFFFAOYSA-N norbornane Chemical class C1CC2CCC1C2 UMRZSTCPUPJPOJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000011282 treatment Methods 0.000 description 23
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- 239000002689 soil Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 20
- 239000010408 film Substances 0.000 description 18
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- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 14
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 14
- 235000009973 maize Nutrition 0.000 description 14
- 239000000969 carrier Substances 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- BEWYHVAWEKZDPP-UHFFFAOYSA-N bornane Chemical compound C1CC2(C)CCC1C2(C)C BEWYHVAWEKZDPP-UHFFFAOYSA-N 0.000 description 10
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- 238000002474 experimental method Methods 0.000 description 10
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- 235000019441 ethanol Nutrition 0.000 description 8
- 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 7
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- 238000010790 dilution Methods 0.000 description 7
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- 239000002270 dispersing agent Substances 0.000 description 7
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- 239000011734 sodium Substances 0.000 description 7
- 238000009331 sowing Methods 0.000 description 7
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 244000020551 Helianthus annuus Species 0.000 description 6
- 235000003222 Helianthus annuus Nutrition 0.000 description 6
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 5
- 240000003768 Solanum lycopersicum Species 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
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- 239000000725 suspension Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- 230000012010 growth Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
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- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- POYGWXWGOBEMAT-UHFFFAOYSA-N n-(2,2,4-trimethyl-3-bicyclo[2.2.1]heptanylidene)hydroxylamine Chemical compound C1CC2C(C)(C)C(=NO)C1(C)C2 POYGWXWGOBEMAT-UHFFFAOYSA-N 0.000 description 1
- OVFDEGGJFJECAT-UHFFFAOYSA-N n-(4,7,7-trimethyl-3-bicyclo[2.2.1]heptanylidene)hydroxylamine Chemical compound C1CC2(C)C(=NO)CC1C2(C)C OVFDEGGJFJECAT-UHFFFAOYSA-N 0.000 description 1
- GTOSUNVDAYWGBM-UHFFFAOYSA-N n-dodecoxy-4,7,7-trimethylbicyclo[2.2.1]heptan-3-imine Chemical compound C1CC2(C)C(=NOCCCCCCCCCCCC)CC1C2(C)C GTOSUNVDAYWGBM-UHFFFAOYSA-N 0.000 description 1
- NGTGENGUUCHSLQ-UHFFFAOYSA-N n-heptan-2-ylidenehydroxylamine Chemical compound CCCCCC(C)=NO NGTGENGUUCHSLQ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
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- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000001737 promoting effect Effects 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
- 239000008262 pumice Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000007226 seed germination Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
Classifications
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (27)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU802774A HU184353B (en) | 1980-11-21 | 1980-11-21 | Plant growth regulating composition containing bicyclo/2.2.1/ heptane derivative further process for preparing bicyclo/2.2.1/ heptane derivatives |
| FI813498A FI65529C (fi) | 1980-11-21 | 1981-11-06 | Reglerkomposition foer vaextodling |
| BE1/10356A BE891128A (fr) | 1980-11-21 | 1981-11-16 | Nouveaux derives du bicyclo (2,2,1) heptane, un procede pour les preparer et compositions controlant la croissance des plantes renfermant ceux-ci |
| US06/322,675 US4425158A (en) | 1980-11-21 | 1981-11-18 | Bicyclo(2.2.1)heptane oximes used for plant growth regulating |
| FR8121661A FR2494687A1 (fr) | 1980-11-21 | 1981-11-19 | Nouveaux derives du bicyclo(2,2,1)heptane, un procede pour les preparer et compositions controlant la croissance des plantes renfermant ceux-ci |
| CS818509A CS234037B2 (en) | 1980-11-21 | 1981-11-19 | Agent for plant growth regulation and method of its active component preparation |
| NL8105235A NL8105235A (nl) | 1980-11-21 | 1981-11-19 | Nieuwe bicyclo(2.2.1)heptaanderivaten, werkwijze voor de bereiding ervan en plantengroeiregulerende samenstellingen, die deze derivaten bevatten. |
| CH7430/81A CH647756A5 (de) | 1980-11-21 | 1981-11-19 | Bicyclo(2.2.1)heptan-derivate. |
| IL64319A IL64319A (en) | 1980-11-21 | 1981-11-19 | Plant growth regulating compositions containing bicyclo(2.2.1)heptane-2-oxime derivatives,certain such novel compounds and their preparation |
| PL1981233896A PL128561B1 (en) | 1980-11-21 | 1981-11-19 | Plant growth regulating agent and method of manufacture of novel derivatives of bicyclo /2.2.1/ heptane |
| AT0498381A AT380233B (de) | 1980-11-21 | 1981-11-19 | Verfahren zur herstellung von neuen 1,7,7 |
| GR66572A GR77308B (en, 2012) | 1980-11-21 | 1981-11-19 | |
| ZA818033A ZA818033B (en) | 1980-11-21 | 1981-11-19 | Plant growth regulating compositions containing bicyclo(2.2.1)heptane derivatives and process for preparing their active agents |
| GB8134890A GB2087888B (en) | 1980-11-21 | 1981-11-19 | New bicyclo(2.2.1)heptane derivatives and their use as plant growth regulants |
| DK516781A DK516781A (da) | 1980-11-21 | 1981-11-20 | Racemiske eller optisk aktive bicyclo (2,2,1) heptanderivater deres fremstilling og anvendelse som plantevaekstregulerende midler |
| DD81235014A DD202086A5 (de) | 1980-11-21 | 1981-11-20 | Pflanzenwachstumsregulierendes mittel |
| ES507350A ES8207137A1 (es) | 1980-11-21 | 1981-11-20 | Procedimiento de preparacion de nuevos derivados biciclo (2.2.1)heptanos. |
| IT8125197A IT1211134B (it) | 1980-11-21 | 1981-11-20 | Derivati del biciclo (2.2.1) eptano procedimento per la loro preparazione e composizioni regolatrici della crescita delle piante. |
| JP56186760A JPS57116042A (en) | 1980-11-21 | 1981-11-20 | Racemic compound or optically active compound, plant growth regulant composition, manufacture and agricultural use |
| ZW282/81A ZW28281A1 (en) | 1980-11-21 | 1981-11-20 | New bicyclo (2.2.1) heptane derivatives a process for the preparation thereof and plant growth regulating compositions containing same |
| BG054236A BG43523A3 (en) | 1980-11-21 | 1981-11-20 | Means for growth regulation of plants |
| SE8106926A SE447377B (sv) | 1980-11-21 | 1981-11-20 | Nya bicyklo/2.2.1/heptanderivat och kompositioner innehallande dem och avsedda for reglering av vexters tillvext |
| DE19813146106 DE3146106A1 (de) | 1980-11-21 | 1981-11-20 | Racemische und optisch aktive 2-substituierte 1,7,7-trimethylbicyclo(2,2,1)heptanderivate, verfahren zu deren herstellung und solche enthaltende pflanzenwuchsregler sowie fungicide und insekticide |
| SU813369302A SU1209027A3 (ru) | 1980-11-21 | 1981-11-20 | Способ получени производных бицикло (2,2,1) гептана в виде рацемата или оптически активного антипода |
| IE2721/81A IE51856B1 (en) | 1980-11-21 | 1981-11-20 | New bicyclo(2.2.1)heptane derivatives,a process for the preparation thereof and plant growth regulating compositions containing same |
| EG677/81A EG15682A (en) | 1980-11-21 | 1981-11-21 | New bicyclo(2-2-1)heptane derivatives,a process for their preparation thereof and plant growth regulating composition containing same |
| US06/551,941 US4511737A (en) | 1980-11-21 | 1983-11-15 | Bicyclo(2.2.1)heptane oximes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU802774A HU184353B (en) | 1980-11-21 | 1980-11-21 | Plant growth regulating composition containing bicyclo/2.2.1/ heptane derivative further process for preparing bicyclo/2.2.1/ heptane derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU184353B true HU184353B (en) | 1984-08-28 |
Family
ID=10961039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU802774A HU184353B (en) | 1980-11-21 | 1980-11-21 | Plant growth regulating composition containing bicyclo/2.2.1/ heptane derivative further process for preparing bicyclo/2.2.1/ heptane derivatives |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US4425158A (en, 2012) |
| JP (1) | JPS57116042A (en, 2012) |
| AT (1) | AT380233B (en, 2012) |
| BE (1) | BE891128A (en, 2012) |
| BG (1) | BG43523A3 (en, 2012) |
| CH (1) | CH647756A5 (en, 2012) |
| CS (1) | CS234037B2 (en, 2012) |
| DD (1) | DD202086A5 (en, 2012) |
| DE (1) | DE3146106A1 (en, 2012) |
| DK (1) | DK516781A (en, 2012) |
| EG (1) | EG15682A (en, 2012) |
| ES (1) | ES8207137A1 (en, 2012) |
| FI (1) | FI65529C (en, 2012) |
| FR (1) | FR2494687A1 (en, 2012) |
| GB (1) | GB2087888B (en, 2012) |
| GR (1) | GR77308B (en, 2012) |
| HU (1) | HU184353B (en, 2012) |
| IE (1) | IE51856B1 (en, 2012) |
| IL (1) | IL64319A (en, 2012) |
| IT (1) | IT1211134B (en, 2012) |
| NL (1) | NL8105235A (en, 2012) |
| PL (1) | PL128561B1 (en, 2012) |
| SE (1) | SE447377B (en, 2012) |
| SU (1) | SU1209027A3 (en, 2012) |
| ZA (1) | ZA818033B (en, 2012) |
| ZW (1) | ZW28281A1 (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU184353B (en) * | 1980-11-21 | 1984-08-28 | Egyt Gyogyszervegyeszeti Gyar | Plant growth regulating composition containing bicyclo/2.2.1/ heptane derivative further process for preparing bicyclo/2.2.1/ heptane derivatives |
| US4735943A (en) * | 1984-06-29 | 1988-04-05 | Sanwa Kagaku Kenkyusho Co., Ltd. | Eburnamonine oxime derivatives, salts thereof, and pharmaceutical agents containing the same |
| MXPA01005352A (es) * | 2000-05-26 | 2005-08-26 | Ajinomoto Kk | Alimento para ganado. |
| JP6287499B2 (ja) * | 2014-04-02 | 2018-03-07 | 住友化学株式会社 | 重合性モノマー、樹脂、レジスト組成物及びレジストパターンの製造方法 |
| US20220162390A1 (en) * | 2019-03-20 | 2022-05-26 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Chalcogenide hybrid organic/inorganic polymers and methods for producing and using the same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU181873B (en) | 1978-08-22 | 1983-11-28 | Egyt Gyogyszervegyeszeti Gyar | Plant growth regulating and/or insecticide composition containing 2-/propagyl-oxy-imino/-1,7,7-trimethyl-byciclo/2.2.1/heptane further process for preparing the active suastance |
| GB2031874B (en) * | 1978-08-22 | 1982-12-15 | Egyt Gyogyszervegyeszeti Gyar | Plant growth regulating and insecticidal compositions |
| HU184353B (en) * | 1980-11-21 | 1984-08-28 | Egyt Gyogyszervegyeszeti Gyar | Plant growth regulating composition containing bicyclo/2.2.1/ heptane derivative further process for preparing bicyclo/2.2.1/ heptane derivatives |
-
1980
- 1980-11-21 HU HU802774A patent/HU184353B/hu not_active IP Right Cessation
-
1981
- 1981-11-06 FI FI813498A patent/FI65529C/fi not_active IP Right Cessation
- 1981-11-16 BE BE1/10356A patent/BE891128A/fr not_active IP Right Cessation
- 1981-11-18 US US06/322,675 patent/US4425158A/en not_active Expired - Fee Related
- 1981-11-19 AT AT0498381A patent/AT380233B/de not_active IP Right Cessation
- 1981-11-19 NL NL8105235A patent/NL8105235A/nl not_active Application Discontinuation
- 1981-11-19 IL IL64319A patent/IL64319A/xx unknown
- 1981-11-19 FR FR8121661A patent/FR2494687A1/fr active Granted
- 1981-11-19 ZA ZA818033A patent/ZA818033B/xx unknown
- 1981-11-19 CS CS818509A patent/CS234037B2/cs unknown
- 1981-11-19 CH CH7430/81A patent/CH647756A5/de not_active IP Right Cessation
- 1981-11-19 PL PL1981233896A patent/PL128561B1/pl unknown
- 1981-11-19 GR GR66572A patent/GR77308B/el unknown
- 1981-11-19 GB GB8134890A patent/GB2087888B/en not_active Expired
- 1981-11-20 JP JP56186760A patent/JPS57116042A/ja active Pending
- 1981-11-20 DD DD81235014A patent/DD202086A5/de unknown
- 1981-11-20 ES ES507350A patent/ES8207137A1/es not_active Expired
- 1981-11-20 BG BG054236A patent/BG43523A3/xx unknown
- 1981-11-20 DK DK516781A patent/DK516781A/da not_active Application Discontinuation
- 1981-11-20 DE DE19813146106 patent/DE3146106A1/de not_active Ceased
- 1981-11-20 IE IE2721/81A patent/IE51856B1/en unknown
- 1981-11-20 SE SE8106926A patent/SE447377B/sv not_active IP Right Cessation
- 1981-11-20 ZW ZW282/81A patent/ZW28281A1/xx unknown
- 1981-11-20 IT IT8125197A patent/IT1211134B/it active
- 1981-11-20 SU SU813369302A patent/SU1209027A3/ru active
- 1981-11-21 EG EG677/81A patent/EG15682A/xx active
-
1983
- 1983-11-15 US US06/551,941 patent/US4511737A/en not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |