DD149935A5 - Verfahren zur herstellung von racemen oder optisch aktivem 2-(propargyloxyimino)-1,7,7-trimethylbicyclo(2,2,1)heptan - Google Patents
Verfahren zur herstellung von racemen oder optisch aktivem 2-(propargyloxyimino)-1,7,7-trimethylbicyclo(2,2,1)heptan Download PDFInfo
- Publication number
- DD149935A5 DD149935A5 DD79220010A DD22001079A DD149935A5 DD 149935 A5 DD149935 A5 DD 149935A5 DD 79220010 A DD79220010 A DD 79220010A DD 22001079 A DD22001079 A DD 22001079A DD 149935 A5 DD149935 A5 DD 149935A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- item
- general formula
- heptane
- bicyclo
- sulfur
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- RYOCQKYEVIJALB-UHFFFAOYSA-N 4,7,7-trimethyl-n-prop-2-ynoxybicyclo[2.2.1]heptan-3-imine Chemical compound C1CC2(C)C(=NOCC#C)CC1C2(C)C RYOCQKYEVIJALB-UHFFFAOYSA-N 0.000 title 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003544 oxime group Chemical group 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 239000011593 sulfur Chemical group 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims abstract description 5
- 150000002367 halogens Chemical group 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 15
- -1 propargyloxyimino Chemical group 0.000 abstract description 9
- 239000005648 plant growth regulator Substances 0.000 abstract description 6
- 239000002917 insecticide Substances 0.000 abstract description 2
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical class CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 abstract description 2
- 101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000013543 active substance Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- 240000006240 Linum usitatissimum Species 0.000 description 3
- 235000004431 Linum usitatissimum Nutrition 0.000 description 3
- 244000300264 Spinacia oleracea Species 0.000 description 3
- 235000009337 Spinacia oleracea Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 235000004426 flaxseed Nutrition 0.000 description 3
- 230000035784 germination Effects 0.000 description 3
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000902 placebo Substances 0.000 description 3
- 229940068196 placebo Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 244000000626 Daucus carota Species 0.000 description 2
- 235000002767 Daucus carota Nutrition 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 239000005445 natural material Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DSSYKIVIOFKYAU-XVKPBYJWSA-N (1s,4r)-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound C1C[C@@]2(C)C(=O)C[C@H]1C2(C)C DSSYKIVIOFKYAU-XVKPBYJWSA-N 0.000 description 1
- NGTGENGUUCHSLQ-BQYQJAHWSA-N (ne)-n-heptan-2-ylidenehydroxylamine Chemical compound CCCCC\C(C)=N\O NGTGENGUUCHSLQ-BQYQJAHWSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- OCBMEHIWWYEZHZ-UHFFFAOYSA-N 3,3,4-trimethylbicyclo[2.2.1]heptane Chemical compound C1CC2(C)C(C)(C)CC1C2 OCBMEHIWWYEZHZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229930192334 Auxin Natural products 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 240000004160 Capsicum annuum Species 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000003914 Cholinesterases Human genes 0.000 description 1
- 108090000322 Cholinesterases Proteins 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 229930191978 Gibberellin Natural products 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 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 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241000758706 Piperaceae Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002363 auxin Substances 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001511 capsicum annuum Substances 0.000 description 1
- 150000001785 cerium compounds Chemical class 0.000 description 1
- 229940048961 cholinesterase Drugs 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 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
- 239000004009 herbicide Substances 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005497 microtitration Methods 0.000 description 1
- CJBSHJOOFLPMKG-UHFFFAOYSA-N n,n,2-trimethylbutanamide Chemical compound CCC(C)C(=O)N(C)C CJBSHJOOFLPMKG-UHFFFAOYSA-N 0.000 description 1
- PUPKPAZSFZOLOR-UHFFFAOYSA-N n,n-dimethylformamide;toluene Chemical compound CN(C)C=O.CC1=CC=CC=C1 PUPKPAZSFZOLOR-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000009105 vegetative growth Effects 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU78EE2589A HU181873B (en) | 1978-08-22 | 1978-08-22 | 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD149935A5 true DD149935A5 (de) | 1981-08-05 |
Family
ID=10995789
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79220010A DD149935A5 (de) | 1978-08-22 | 1979-08-17 | Verfahren zur herstellung von racemen oder optisch aktivem 2-(propargyloxyimino)-1,7,7-trimethylbicyclo(2,2,1)heptan |
| DD79215051A DD145491A5 (de) | 1978-08-22 | 1979-08-17 | Pflanzenwachstumsregelndes oder insekticides mittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79215051A DD145491A5 (de) | 1978-08-22 | 1979-08-17 | Pflanzenwachstumsregelndes oder insekticides mittel |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US4244888A (cs) |
| JP (1) | JPS5551002A (cs) |
| AT (1) | AT370586B (cs) |
| BE (1) | BE878266A (cs) |
| BG (2) | BG31488A3 (cs) |
| CH (1) | CH643537A5 (cs) |
| CS (1) | CS214672B2 (cs) |
| DD (2) | DD149935A5 (cs) |
| DE (1) | DE2933405C2 (cs) |
| DK (1) | DK349379A (cs) |
| FR (1) | FR2434148A1 (cs) |
| HU (1) | HU181873B (cs) |
| IL (1) | IL57991A (cs) |
| IT (1) | IT1163699B (cs) |
| NL (1) | NL189252C (cs) |
| PL (1) | PL118502B1 (cs) |
| SU (1) | SU1248532A3 (cs) |
Families Citing this family (10)
| 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 |
| US4469663A (en) * | 1982-10-15 | 1984-09-04 | The Dow Chemical Company | Scale control in flue gas desulfurization |
| PH19023A (en) * | 1983-06-16 | 1985-12-03 | Egyt Gyogyszervegyeszeti Gyar | Seed treatment method for safening rice and sorghun |
| US4752319A (en) * | 1983-08-15 | 1988-06-21 | Westvaco Corporation | Seed treatment method with aqueous suspension of alkali lignin |
| US4624694A (en) * | 1983-08-15 | 1986-11-25 | Westvaco Corporation | Seed treatment method with aqueous suspension of alkali lignin |
| US4581057A (en) * | 1984-03-15 | 1986-04-08 | The Board Of Regents Of University Of Michigan, Corp. Of Michigan | Abscisic acid containing foliar fertilizers and method of using same to enhance crop yields |
| KR100381558B1 (ko) * | 1994-07-01 | 2003-08-19 | 에지스 지오기스제르기아르 알티. | 약제조성물및이의제조방법 |
| DE29912822U1 (de) | 1999-07-22 | 2000-08-17 | Anton Heggenstaller AG, 86556 Kühbach | Strangpresse für pflanzliche Kleinteile |
| DE10013184A1 (de) | 2000-03-17 | 2001-09-20 | Deutsche Telekom Ag | Verfahren zur Veränderung der Polarisation wenigstens eines der aus einer Photonenpaarquelle in verschiedene Teilstrahlengänge abgestrahlten Photonen sowie Verfahren zur Erzeugung von wahlweise Einzelphotonen oder Photonenpaaren in einem optischen Kanal |
| DE20018347U1 (de) | 2000-10-26 | 2001-10-31 | Anton Heggenstaller AG, 86556 Kühbach | Strangpresse für mit Bindemittel vermengte pflanzliche Kleinteile |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1733462A (en) * | 1926-09-23 | 1929-10-29 | Winthrop Chem Co Inc | New basic oxime ethers of cyclic compounds |
| CH455386A (de) * | 1965-01-22 | 1968-07-15 | Ciba Geigy | Schädlingsbekämpfungsmittel |
| US3941839A (en) * | 1965-01-22 | 1976-03-02 | Ciba-Geigy Ag | Oxime ethers and pesticidal preparations containing them |
| FR1601217A (cs) * | 1968-01-15 | 1970-08-10 | ||
| GB1318681A (en) * | 1971-01-01 | 1973-05-31 | Shell Int Research | Phenyl ketoxime derivatives |
| US4020111A (en) * | 1973-09-13 | 1977-04-26 | Hennessy Douglas J | Propynyloxy alkyl arene insecticides |
| JPS577122B2 (cs) * | 1973-12-24 | 1982-02-09 | ||
| US4052194A (en) * | 1974-01-24 | 1977-10-04 | Merrill Wilcox | Oxime abscission agents |
-
1978
- 1978-08-22 HU HU78EE2589A patent/HU181873B/hu not_active IP Right Cessation
-
1979
- 1979-08-06 IL IL57991A patent/IL57991A/xx unknown
- 1979-08-06 AT AT0535479A patent/AT370586B/de not_active IP Right Cessation
- 1979-08-08 CS CS795443A patent/CS214672B2/cs unknown
- 1979-08-09 US US06/065,156 patent/US4244888A/en not_active Expired - Lifetime
- 1979-08-16 FR FR7920764A patent/FR2434148A1/fr active Granted
- 1979-08-16 BE BE1/9491A patent/BE878266A/fr not_active IP Right Cessation
- 1979-08-17 DD DD79220010A patent/DD149935A5/de unknown
- 1979-08-17 DE DE2933405A patent/DE2933405C2/de not_active Expired
- 1979-08-17 DD DD79215051A patent/DD145491A5/de unknown
- 1979-08-20 BG BG047546A patent/BG31488A3/xx unknown
- 1979-08-20 IT IT25164/79A patent/IT1163699B/it active
- 1979-08-20 BG BG044692A patent/BG30626A3/xx unknown
- 1979-08-20 CH CH758779A patent/CH643537A5/de not_active IP Right Cessation
- 1979-08-20 NL NLAANVRAGE7906297,A patent/NL189252C/xx not_active IP Right Cessation
- 1979-08-21 JP JP10654979A patent/JPS5551002A/ja active Granted
- 1979-08-21 PL PL1979217880A patent/PL118502B1/pl unknown
- 1979-08-21 DK DK349379A patent/DK349379A/da not_active Application Discontinuation
-
1980
- 1980-07-09 US US06/166,975 patent/US4310348A/en not_active Expired - Lifetime
-
1984
- 1984-10-19 SU SU843803960A patent/SU1248532A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| IT1163699B (it) | 1987-04-08 |
| JPS5551002A (en) | 1980-04-14 |
| IT7925164A0 (it) | 1979-08-20 |
| AT370586B (de) | 1983-04-11 |
| IL57991A0 (en) | 1979-12-30 |
| JPS5748150B2 (cs) | 1982-10-14 |
| ATA535479A (de) | 1982-09-15 |
| HU181873B (en) | 1983-11-28 |
| DE2933405A1 (de) | 1980-03-06 |
| CH643537A5 (de) | 1984-06-15 |
| NL7906297A (nl) | 1980-02-26 |
| FR2434148A1 (fr) | 1980-03-21 |
| SU1248532A3 (ru) | 1986-07-30 |
| IL57991A (en) | 1983-06-15 |
| CS214672B2 (en) | 1982-05-28 |
| DE2933405C2 (de) | 1985-12-05 |
| PL118502B1 (en) | 1981-10-31 |
| DD145491A5 (de) | 1980-12-17 |
| NL189252C (nl) | 1993-02-16 |
| BG30626A3 (en) | 1981-07-15 |
| PL217880A1 (cs) | 1980-05-19 |
| US4244888A (en) | 1981-01-13 |
| DK349379A (da) | 1980-02-23 |
| US4310348A (en) | 1982-01-12 |
| BG31488A3 (en) | 1982-01-15 |
| BE878266A (fr) | 1980-02-18 |
| FR2434148B1 (cs) | 1983-03-25 |
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