JPS627195B2 - - Google Patents
Info
- Publication number
- JPS627195B2 JPS627195B2 JP58130372A JP13037283A JPS627195B2 JP S627195 B2 JPS627195 B2 JP S627195B2 JP 58130372 A JP58130372 A JP 58130372A JP 13037283 A JP13037283 A JP 13037283A JP S627195 B2 JPS627195 B2 JP S627195B2
- Authority
- JP
- Japan
- Prior art keywords
- oxa
- homo
- ethyl
- cholestan
- group
- 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
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 15
- 241000196324 Embryophyta Species 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 230000008635 plant growth Effects 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 230000001105 regulatory effect Effects 0.000 claims description 5
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 230000001850 reproductive effect Effects 0.000 claims description 3
- 244000068988 Glycine max Species 0.000 claims description 2
- 235000010469 Glycine max Nutrition 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 230000016574 developmental growth Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 238000002844 melting Methods 0.000 description 24
- 230000008018 melting Effects 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000013543 active substance Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000012010 growth Effects 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- WSSZZUWWCXSGKJ-WFDUKQKSSA-N (8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one Chemical compound C1C(=O)C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 WSSZZUWWCXSGKJ-WFDUKQKSSA-N 0.000 description 2
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000002734 clay mineral Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- -1 fatty alcohol sulfates Chemical class 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 235000021374 legumes Nutrition 0.000 description 2
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- FCOGYPACUCYJOO-UHFFFAOYSA-N (2-ethoxyacetyl) 2-ethoxyacetate Chemical compound CCOCC(=O)OC(=O)COCC FCOGYPACUCYJOO-UHFFFAOYSA-N 0.000 description 1
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JACPTQMMZGZAOL-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCN(C)CCS(O)(=O)=O JACPTQMMZGZAOL-KHPPLWFESA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- IXVMHGVQKLDRKH-VRESXRICSA-N Brassinolide Natural products O=C1OC[C@@H]2[C@@H]3[C@@](C)([C@H]([C@@H]([C@@H](O)[C@H](O)[C@H](C(C)C)C)C)CC3)CC[C@@H]2[C@]2(C)[C@@H]1C[C@H](O)[C@H](O)C2 IXVMHGVQKLDRKH-VRESXRICSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 208000012868 Overgrowth Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
- 230000002180 anti-stress Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IXVMHGVQKLDRKH-KNBKMWSGSA-N brassinolide Chemical compound C1OC(=O)[C@H]2C[C@H](O)[C@H](O)C[C@]2(C)[C@H]2CC[C@]3(C)[C@@H]([C@H](C)[C@@H](O)[C@H](O)[C@@H](C)C(C)C)CC[C@H]3[C@@H]21 IXVMHGVQKLDRKH-KNBKMWSGSA-N 0.000 description 1
- 150000001646 brassinolides Chemical class 0.000 description 1
- 150000001647 brassinosteroids Chemical class 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N carbon tetrachloride Substances ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000014100 regulation of seed germination Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
- C07J73/001—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
- C07J73/003—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by oxygen as hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Insects & Arthropods (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Steroid Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は新規28−メチル−ブラツシノステロイ
ド誘導体、その製法及び該化合物を含有する植物
生長調節作用を有する薬剤に関する。
セイヨウアブラナの花粉から植物の生長を促進
するステロイドであるブラツシノリドが単離さ
れ、構造が解明された(M.D.Grove等著、
Nature第281巻、第216頁(1979年)参照)。しか
しながらこの化合物の生長調節作用は不十分であ
る。
本発明の課題は公知の構造類似ブラツシノリド
に比較して優れた植物生長調節作用を有する新規
ブラツシノステロイド誘導体を得ることである。
この課題は本発明において、一般式
[式中、Zは基
The present invention relates to a novel 28-methyl-bratusinosteroid derivative, a method for producing the same, and a drug containing the compound that has a plant growth regulating effect. Brassinolide, a steroid that promotes plant growth, was isolated from rapeseed pollen and its structure was elucidated (MD Grove et al.
(See Nature, Vol. 281, p. 216 (1979)). However, the growth regulating effect of this compound is insufficient. The object of the present invention is to obtain a novel brassinosteroid derivative having superior plant growth regulating activity compared to known structurally similar brassinolides. In the present invention, this problem is solved by the general formula [In the formula, Z is a group
【式】を表わし、R2は
アセチル又はバレリル基を表わし、R3は水素又
はアセチル基を表わし、R22は水素又はアセチル
基を表わし、かつR3及びR22は同時にアセチル基
を表わさない]の化合物を少なくとも1種含有す
ることを特徴とする薬剤により解決する。
本発明による化合物は幾何異性体として生じ、
ここで−OR2及び−OR3はシス2α・3αであ
り、OR22及びOH23はシス22R・23Rの構造である
か、又はシス22S・23Sの構造である。個々の異
性体もその混合物も本発明の目的物質に属する。
本発明による化合物は種々の栽培植物において
植物生長を調節するために著しく好適であり、冒
頭にあげた同じ作用方向の生成物をその作用スペ
クトルにおいて並びにその相容性において上回
る。
本発明による化合物は栽培植物の増殖的生長を
促進することが可能であるが、ある濃度範囲では
抑制することも可能である。更に、発生段階への
影響により一定の増収を達成することができる。
一般にこの物質は栽培植物において膜システム
に作用し、種々の物質に対する浸透性を変える。
この物質は一定の条件下に抗ストレス作用をく
り広げることもできる。
本発明による化合物は植物の質的及び量的変化
も、植物の代謝における変化をもひき起すので、
植物生長調節剤の分類に入れることができ、これ
は次の使用可能性により優れている。
例えば道路端、軌条設備等の大本及び草本植物
においては繁茂生長を阻止するための増殖的生長
の抑制。殻物においては倒れたり、折れることを
阻止するための生長抑制、綿花においては収穫増
大のための生長抑制。
観賞植物及び栽培植物においては花芽を増加す
るために増殖器官及び発生器官の分枝への影響又
はタバコ及びトマトにおいては側芽の抑制。
果実品質の改良、例えばサトウキビ、サトウダ
イコン又は果物における糖含量の上昇及び収穫量
を高める収穫物の一定の成熟。
ストレス、例えば寒冷及び乾燥のような気象条
件の影響に対しても、化学物質の植物毒的影響に
対しても抵抗力の増大。
ゴムの木におけるラテツクス液への影響。
単為結実果実の形成、花粉不稔性及び性への影
響にも同様に使用可能である。
種子の発芽調節又は花芽の発芽の調節。
収穫を容易にするための落葉又は果実落下の影
響。
本発明による化合物は特にいくつかの豆科植
物、例えば大豆において増殖的及び発生的生長へ
の影響に好適である。
使用量はそれぞれ使用目的により一般に作用物
質0.001〜1Kg/haであり、場合により更に高使
用量も使用することができる。
使用時期は使用目的及び気候上の条件により決
まる。
本発明による化合物は単一で、相互に混合物
で、又は他の作用物質と共に使用することができ
る。場合により、それぞれ所望の目的に従つて落
葉剤、植物保護剤又は有害動植物駆除剤を添加す
ることができる。
作用スペクトルを拡大することが所望であれ
ば、他の殺生剤を添加することもできる。除草作
用性混合対としてはウイード・アブストラクツ
(Weed Abstracts)、第31巻、1981年中の表題
“リスト・オブ・コモン・ネームズ・アンド・ア
ブレビエイシヨンズ・エンプロイド・フオー・カ
レントリー・ユーズド・ハービサイズ・アンド・
プラント・グロース・レグユレイターズ・イン・
ウイード・アブストラクツ(List of common
names and Abbreviations employed for
currently used herbicides and plant growth
regulators in weed abstracts)”中に記載され
ている作用物質が好適である。更に、除草剤及
び/又は生長調節剤と相乗的に作用効果を高め
る、植物毒でない薬剤、例えば特に湿潤剤、乳化
剤、溶剤及び油状添加物を使用することができ
る。
本発明による作用物質又はその混合物を液状及
び/又は固体担体もしくは希釈剤及び場合により
湿潤剤、接着剤、乳化助剤及び/又は分散助剤を
添加して調剤形、例えば粉末、散布剤、顆粒剤、
溶液、乳剤又は懸濁剤の形で使用するのが有利で
ある。
好適な液状担体は例えば水、脂肪族及び芳香族
炭化水素、例えばベンゾール、トルオール、キシ
ロール、シクロヘキサノン、イソホロン、ジメチ
ルスルホキシド、ジメチルホルムアミド、更に鉱
油留分である。
固体担体としては鉱土、例えばトーンシル、シ
リカゲル、タルク、カオリン、アタツクレー、石
灰石、珪酸及び植物製品、例えば穀粉が好適であ
る。
界面活性物質としては例えばリグニンスルホン
酸カルシウム、ポリオキシエチレン−アルキルフ
エノールエーテル、ナフタリンスルホン酸及びそ
の塩、フエノールスルホン酸及びその塩、ホルム
アルデヒド縮合体、脂肪アルコールスルフエート
並びに置換ベンゾールスルホン酸及びその塩であ
る。
種々の調剤形におけるそれぞれの作用物質の量
は広い範囲で変化させることができる。例えばこ
の薬剤は作用物質を約10〜80重量%、液状又は固
体担体を90〜20重量%並びに場合により表面活性
物質を20重量%まで含有していてよい。
この薬剤の散布は常法で行なわれ、例えば担体
として水を用いて約100〜1000/haの散布液量
にするのがよい。いわゆる低容量又は超低容量法
にこの薬剤を適用することは、いわゆるマイクロ
顆粒の形で適用すると同様に可能である。
調剤の製造には例えば次の成分を使用する。
A 散布用粉末
(a) 作用物質 80重量%
カオリン 15重量%
界面活性剤(N−メチル−N−オレイル−タ
ウリンのナトリウム塩及びリグニンスルホン
酸のカルシウム塩を基礎とする) 5重量%
(b) 作用物質 50重量%
粘土鉱物 40重量%
セルピツチ 5重量%
界面活性剤(リグニンスルホン酸のカルシウ
ム塩とアルキルフエノールポリグリコールエ
ーテルとの混合物を基礎とする) 5重量%
(c) 作用物質 20重量%
粘土鉱物 70重量%
セルピツチ 5重量%
界面活性剤(リグニンスルホン酸のカルシウ
ム塩とアルキルフエノールポリグリコールエ
ーテルとの混合物を基礎とする) 5重量%
(d) 作用物質 5重量%
トーンシル 80重量%
セルピツチ 10重量%
界面活性剤(脂肪酸縮合製品を基礎とする)
5重量%
B 乳剤濃縮物
作用物質 20重量%
キシロール 40重量%
ジメチルスルホキシド 35重量%
ノニルフエニルポリオキシエチレン又はドデシ
ルベンゼンスルホン酸カルシウムの混合物
5重量%
C ペースト
作用物質 45重量%
珪酸アルミニウムナトリウム 5重量%
エチレンオキシド8モルを有するセチルポリグ
リコールエーテル 15重量%
スピンドルオイル 2重量%
ポリエチレングリコール 10重量%
水 23部
新規本発明による化合物は例えば、一般式
[式中、Zは前記のものを表わす]の化合物を場
合により触媒の存在下にカルボン酸無水物と反応
させ、所望の目的化合物を自体公知法で単離する
ことにより製造される。
出発物質28−メチル−ブラツシノリドは例えば
ステロイド第39巻、第89頁(1982年)に記載され
ているように、ステイグマステリンから製造され
る。
次の実施例につき本発明の化合物の製法に関し
て詳細に説明する。
例 1
2α・3α・22S・23S−テトラヒドロキシ−
24−エチル−7−オキサ−B−ホモ−5α−コレ
スタン−6−オン1gをピリジン10ml中に溶か
し、0℃に冷却し、無水酢酸0.5mlを加え、−5〜
0℃で5.5時間撹拌する。その後、氷水中で析出
させ、生成物を吸引濾過し、水で洗浄し、乾燥さ
せ、シリカゲル上でクロマトグラフイーにかけ
る。アセトン/ヘキサンから再結晶させた後、融
点125℃の2α−アセトキシ−3α・22S・23S−
トリヒドロキシ−24−エチル−7−オキサ−B−
ホモ−5α−コレスタン−6−オン810mgが得ら
れる。
例 2
2α・3α・22S・23S−テトラヒドロキシ−
24−エチル−7−オキサ−B−ホモ−5α−コレ
スタン−6−オン1gをピリジン10ml中に溶か
し、0℃に冷却し、無水酢酸1mlと混合し、0℃
で7時間撹拌する。その後、氷水中で析出させ、
吸引濾過し、水で洗浄し、乾燥させる。シリカゲ
ル上でクロマトグラフイーにかけた後(クロロホ
ルム/アセトンでの傾斜溶離)、融点120℃の2
α・3α−ジアセトキシ−22S・23S−ジヒドロ
キシ−24−エチル−7−オキサ−B−ホモ−5α
−コレスタン−6−オン320mg及び融点146℃の2
α・22S−ジアセトキシ−3α・23S−ジヒドロ
キシ−24−エチル−7−オキサ−B−ホモ−5α
−コレスタン−6−オン535mgが得られる。
例 3
2α・3α・22R・23R−テトラヒドロキシ−
24−エチル−7−オキサ−B−ホモ−5α−コレ
スタン−6−オン210mgを例1に記載したように
反応させる。アセトン/ヘキサンから再結晶させ
ると、融点246〜248℃の2α−アセトキシ−3
α・22R・23R−トリヒドロキシ−24−エチル−
7−オキサ−B−ホモ−5α−コレスタン−6−
オン170mgが得られる。
例 4(参考例)
2α・3α・22S・23S−テトラヒドロキシ−
24−エチル−6−オキサ−B−ホモ−5α−コレ
スタン−7−オン500mgを例1と同様にして反応
させる。塩化メチレン/イソプロピルエーテルか
ら再結晶させた後、融点198〜200℃の2α−アセ
トキシ−3α・22S・23S−トリヒドロキシ−24
−エチル−6−オキサ−B−ホモ−5α−コレス
タン−7−オン385gが得られる。
例 5(参考例)
2α・3α・22S・23S−テトラヒドロキシ−
24−エチル−6−オキサ−B−ホモ−5α−コレ
スタン−7−オン1gを例2に記載したように反
応させ、分離する。融点135℃の2α・3α−ジ
アセトキシ−22S・23S−ジヒドロキシ−24−エ
チル−6−オキサ−B−ホモ−5α−コレスタン
−7−オン290mg及び融点152℃の2α・22S−ジ
アセトキシ−3α・23S−ジヒドロキシ−24−エ
チル−6−オキサ−B−ホモ−5α−コレスタン
−7−オン560mgが得られる。
例 6(参考例)
2β・3β・22S・22S−テトラヒドロキシ−
24−エチル−7−オキサ−B−ホモ−5α−コレ
スタン−6−オン(融点:182〜183℃)500mgを
例1に記載したようにアセチル化した。融点161
〜162℃の3β−アセトキシ−2β・22S・23S−
トリヒドロキシ−24−エチル−7−オキサ−B−
ホモ−5α−コレスタン−6−オン410mgが得ら
れる。
例 7
2α・3α・22S・23S−テトラヒドロキシ−
24−エチル−7−オキサ−B−ホモ−5α−コレ
スタン−6−オン300mgをピリジン3ml中に溶か
し、0℃に冷却し、吉草酸無水物0.6mlと混合す
る。0℃で10時間撹拌し、氷水中で析出させ、水
で洗浄し、乾燥させる。この粗生成物をシリカゲ
ル上でクロマトグラフイーにかけ、得られた2α
−バレリルオキシ−3α・22S・23S−トリヒド
ロキシ−24−エチル−7−オキサ−B−ホモ−5
α−コレスタン−6−オンをアセトン/ヘキサン
から再結晶させる、融点100〜105℃。
同様にして製造(参考):
2α−ヘプタノイルオキシ−3α・22R・23R
−トリヒドロキシ−24−エチル−7−オキサ−2
−ホモ−5α−コレスタン−6−オン、融点:85
〜87℃、
2α−ジメチルアセトキシ−3α・22S・23S
−トリヒドロキシ−24−エチル−7−オキサ−B
−ホモ−5α−コレスタン−6−オン、融点:
121〜122.5℃、
2α−ブチリルオキシ−3α・22S・23S−ト
リヒドロキシ−24−エチル−6−オキサ−B−ホ
モ−5α−コレスタン−7−オン、融点:92〜94
℃、
2α−ジエチルアセトキシ−3α・22S・23S
−トリヒドロキシ−24−エチル−7−オキサ−B
−ホモ−5α−コレスタン−6−オン、融点:
113〜115℃。
例 8(参考例)
2α・3α・22S・23S−テトラヒドロキシ−
24−エチル−7−オキサ−B−ホモ−5α−コレ
スタン−6−オン300mgをピリジン3ml中に溶か
し、0℃に冷却し、吉草酸無水物1mlを加える。
0℃で20時間撹拌し、氷水中で析出させ、水で洗
浄し、乾燥させる。シリカゲル上でクロマトグラ
フイーにかけた後(クロロホルム/アセトンで傾
斜溶離)、融点:109〜111℃の2α・3α−ジバ
レリルオキシ−22S・23S−ジヒドロキシ−24−
エチル−7−オキサ−B−ホモ−5α−コレスタ
ン−6−オン120mg及び融点:128.5〜130℃の2
α・22S−ジバレリルオキシ−3α・23S−ジヒ
ドロキシ−24−エチル−7−オキサ−B−ホモ−
5α−コレスタン−6−オン160mgが得られる。
同様にして次のものが製造される:
2α・3α−ジヘキサノイルオキシ−22S・
23S−ジヒドロキシ−24−エチル−7−オキサ−
B−ホモ−5α−コレスタン−6−オン、融点:
88〜90℃
2α・22S−ジヘキサノイルオキシ−3α・
23S−ジヒドロキシ−24−エチル−7−オキサ−
B−ホモ−5α−コレスタン−6−オン、融点:
117〜120℃。
例 9(参考)
2α・3α・22R・23R−テトラヒドロキシ−
24−エチル−7−オキサ−B−ホモ−5α−コレ
スタン−6−オン500mgをピリジン5ml中に溶か
し、0℃に冷却し、エトキシ酢酸無水物0.3mlを
加え、−5〜0℃で6時間撹拌する。例1と同様
に処理及び単離した後、2α−エトキシアセトキ
シ−3α・22R・23R−トリヒドロキシ−24−エ
チル−7−オキサ−B−ホモ−5α−コレスタン
−6−オン、融点182〜185℃、310mgが得られ
る。
例 10(参考例)
2α・3α・22S・23S−テトラヒドロキシ−
24−エチル−7−オキサ−B−ホモ−5α−コレ
スタン−6−オン1gをテトラヒドロフラン100
ml及びアセトン100ml中で三弗化硼素エーテル錯
化合物0.5mlと反応させ、−5〜0℃で30分間撹す
る。ピリジン1mlを添加した後、真空中で濃縮
し、水で析出させ、吸引濾別し、水で洗浄する。
アセトンから再結晶させた後、融点198〜201℃の
2α・3α−イソプロピリデンジオキシ−22S・
23S−ジヒドロキシ−24−エチル−7−オキサ−
B−ホモ−5α−コレスタン−6−オン731mgが
得られる。
同様にして次のものが製造される:
2α・3α−イソプロピリデンジオキシ−22S
−23S−ジヒドロキシ−24−エチル−6−オキサ
−B−ホモ−5α−コレスタン−7−オン、融
点:211〜213℃、
2β・3β−イソプロピリデンジオキシ−
22S・23S−ジヒドロキシ−24−エチル−7−オ
キサ−B−ホモ−5α−コレスタン−6−オン、
融点:189〜191℃。
例 11(参考例)
2α・3α・22S・23S−テトラヒドロキシ−
24−エチル−7−オキサ−B−ホモ−5α−コレ
スタン−6−オン1gをベンゾール100ml中でト
リエチルオルト酢酸エステル1.5ml及びp−トル
オールスルホン酸5mgと混合し、室温で30分間撹
拌する。ピリジン2滴を添加した後、真空中で濃
縮し、塩化メチレンで希釈し、水で洗浄し、濃縮
する。粗生成物をイソプロピルエーテルと一縮に
こすると、無定形2α・3α−(1−エトキシエ
チレンジオキシ)−22S・23S−ジヒドロキシ−24
−エチル−7−オキサ−B−ホモ−5α−コレス
タン−6−オン720mgはジアステレオマー混合物
として得られる。
同様にして次のものが得られる:
2α・3α−(1−エトキシ−プロピリデンジ
オキシ)−22S・23S−ジヒドロキシ−24−エチル
−7−オキサ−B−ホモ−5α−コレスタン−6
−オン、無定形、
2α・3α−(1−メトキシ−メチレンジオキ
シ)−22R・23R−ジヒドロキシ−24−エチル−7
−オキサ−B−ホモ−5α−コレスタン−6−オ
ン、融点:96〜99℃、
2β・3β−(1−エトキシ−エチレンジオキ
シ)−22S・23S−ジヒドロキシ−24−エチル−7
−オキサ−B−ホモ−5α−コレスタン−6−オ
ン、融点:84〜87℃。
例 12(参考例)
2α・3α・22S・23S−テトラヒドロキシ−
24−エチル−7−オキサ−B−ホモ−5α−コレ
スタン−6−オン200mgをアセトフエノン2ml中
で72%過塩素酸0.01mlと混合し、室温で16時間撹
拌する。引き続き、ピリジン0.1mlを添加し、シ
リカゲル上でクロマトグラフイーにかける。トル
オール/酢酸エステルでの傾斜溶離により、無定
形2α・3α−(1−メチル−l−フエニル−メ
チレンジオキシ)−22S・23S−ジヒドロキシ−24
−エチル−7−オキサ−B−ホモ−5α−コレス
タン−6−オン120mgがジアステレオマー混合物
として得られる。
同様にして次のものが製造される:
2α・3α−(1−メチル−1−フエニル−メ
チレンジオキシ)−22S・23S−ジヒドロキシ−24
−エチル−6−オキサ−B−ホモ−5α−コレス
タン−7−オン。
例 13(参考例)
2α・3α−22S・23S−テトラヒドロキシ−
24−エチル−6−オキサ−B−ホモ−5α−コレ
スタン−7−オン200mgを炭酸ジエチル7ml及び
テトラヒドロフラン2ml中でナトリウムメチレー
ト15mgを添加した後130℃(浴温)に2.5時間加熱
する。冷却後、酢酸で中和し、真空中で濃縮す
る。残分をクロロホルム/アセトン中に溶かし、
シリカゲル上で濾過し、濾液を濃縮する。アセト
ン/ヘキサンから再結晶させることにより、融
点:242.5〜244℃の2α・3α−カルボニルジオ
キシ−22S・23S−ジヒドロキシ−24−エチル−
6−オキサ−B−ホモ−5α−コレスタン−7−
オン155mgが得られる。
同様にして次のものが得られる:
2α・3α−カルボニルジオキシ−22R・23R
−ジヒドロキシ−24−エチル−6−オキサ−B−
ホモ−5α−コレスタン−7−オン、融点:216
〜217℃
例 14(参考例)
2α・3α・22S・23S−テトラヒドロキシ−
24−エチル−6−オキサ−B−ホモ−5α−コレ
スタン−7−オン200mgをテトラヒドロフラン4
ml中に溶かし、ベンジルアルデヒド1mlを加え、
−15℃に冷却し、過塩素酸溶液(テトラヒドロフ
ラン1.5ml中の70%過塩素酸0.5mlから製造)0.2ml
を加える。−15℃で15分間撹拌し、ピリジンで中
和し、クロロホルムで希釈し、シリカゲル上でク
ロマトグラフイーにかける。クロロホルム/アセ
トン(1:1)で無定形2α・3α−ベンジリデ
ンジオキシ−22S・23S−ジヒドロキシ−24−エ
チル−6−オキサ−B−ホモ−5α−コレスタン
−7−オン153mgが溶離される。
同様にして次のものが得られる:
2α・3α−ベンジリデンジオキシ−22R・
23R−ジヒドロキシ−24−エチル−7−オキサ−
B−ホモ−5α−コレスタン−6−オン、
2α・3α−ベンジリデンジオキシ−22S・
23S−ジヒドロキシ−24−エチル−7−オキサ−
B−ホモ−5α−コレスタン−6−オン。
本発明による化合物は一般に無色無臭の結晶性
物質であり、これは水中に難溶性であり、石油エ
ーテル、ヘキサン、ペンタン及びシクロヘキサン
のような脂肪族炭化水素中に一定量可溶性であ
り、クロロホルム、塩化メチレン、四塩化炭素の
ようなハロゲン化炭化水素、芳香族炭化水素、例
えばベンゾール、トルオール及びキシロール、エ
ーテル、例えばジエチルエーテル、テトラヒドロ
フラン及びジオキサン、アセトニトリルのような
カルボン酸ニトリル、アセトンのようなケトン、
メタノール及びエタノールのようなアルコール、
ジメチルホルムアミドのようなカルボン酸アミド
及びジメチルスルホキシドのようなスルホキシド
には易溶性である。
次の実施例につき前記の調剤形で行なわれる本
発明の化合物の使用可能性を詳述する。
例 15
つるなし豆類における生長促進
種“ピント(Pinto)”のつるなし豆類を空気調
整室中で25℃、空中湿度90%で、660nmの範囲
で強度の高い部分を、かつ730nmの範囲で非常
に低い部分を有する光の作用下に栽培する。
6日間栽培した後、試験すべき化合物10及び50
μgを溶剤中に溶かし、生長する第2の節間に担
持させる。
適用3日後節間の伸びを測定し、かつコントロ
ールにくらべて伸び率を調べる。
次の表にこの結果を記載する。[Formula], R 2 represents an acetyl or valeryl group, R 3 represents hydrogen or an acetyl group, R 22 represents hydrogen or an acetyl group, and R 3 and R 22 do not represent an acetyl group at the same time] The problem is solved by a drug characterized by containing at least one compound. The compounds according to the invention occur as geometric isomers;
Here, -OR 2 and -OR 3 are cis 2α/3α, and OR 22 and OH 23 are cis 22R/23R structures or cis 22S/23S structures. Both individual isomers and mixtures thereof belong to the target substances of the present invention. The compounds according to the invention are eminently suitable for regulating plant growth in various cultivated plants and exceed the products mentioned at the outset with the same direction of action in their spectrum of action as well as in their compatibility. The compounds according to the invention are capable of promoting the productive growth of cultivated plants, but also inhibiting it within a certain concentration range. Furthermore, certain increases in yield can be achieved by influencing the developmental stage. Generally, these substances act on membrane systems in cultivated plants, changing their permeability to various substances. This substance can also develop anti-stress effects under certain conditions. Since the compounds according to the invention cause qualitative and quantitative changes in plants as well as changes in the metabolism of plants,
It can be placed in the class of plant growth regulators, which is distinguished by the following possible uses: For example, suppressing the reproductive growth of large plants and herbaceous plants on roadsides, rail facilities, etc. to prevent overgrowth. Growth control is used to prevent shell crops from falling over or breaking, and growth control is used to increase yields of cotton. In ornamental and cultivated plants, influencing the branching of propagating and developmental organs to increase flower buds, or in tobacco and tomato, suppressing lateral buds. Improving fruit quality, such as increasing the sugar content in sugar cane, sugar beets or fruits and constant ripening of the crop to increase yield. Increased resistance to stress, both to the effects of weather conditions such as cold and dryness, and to the phytotoxic effects of chemicals. Effects on latex fluid in rubber trees. It can also be used to affect parthenocarpic fruit formation, pollen sterility and sex. Regulation of seed germination or regulation of flower bud germination. Effect of leaf or fruit fall to facilitate harvesting. The compounds according to the invention are particularly suitable for influencing reproductive and developmental growth in some leguminous plants, such as soybean. Depending on the purpose of use, the amounts used are generally from 0.001 to 1 kg/ha of active substance; higher amounts can also be used if necessary. The timing of use depends on the purpose of use and climatic conditions. The compounds according to the invention can be used alone, in mixtures with one another or together with other active substances. Optionally, defoliants, plant protection agents or pest control agents can be added, depending in each case on the desired purpose. Other biocides can also be added if it is desired to widen the spectrum of action. Herbicidal mixtures are listed in Weed Abstracts, Volume 31, 1981 under the title "List of Common Names and Abbreviations Employed for Current Used." Herbisize &
Plant Growth Regulators in
Weed Abstracts (List of common
names and abbreviations employed for
currently used herbicides and plant growth
In addition, non-phytotoxic agents, such as in particular wetting agents, emulsifiers, Solvents and oily additives can be used.The active substances according to the invention or their mixtures are added to liquid and/or solid carriers or diluents and optionally wetting agents, adhesives, emulsifying and/or dispersing agents. and dosage forms, e.g. powders, dusting powders, granules,
It is advantageous to use them in the form of solutions, emulsions or suspensions. Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons such as benzole, toluol, xylol, cyclohexanone, isophorone, dimethyl sulfoxide, dimethyl formamide, and also mineral oil fractions. Suitable solid carriers are mineral earths, such as tonesil, silica gel, talc, kaolin, attack clay, limestone, silicic acid, and vegetable products, such as flour. Examples of surface-active substances include calcium lignin sulfonate, polyoxyethylene-alkyl phenol ether, naphthalene sulfonic acid and its salts, phenolsulfonic acid and its salts, formaldehyde condensates, fatty alcohol sulfates, and substituted benzene sulfonic acids and their salts. It is. The amounts of the respective active substances in the various dosage forms can vary within wide limits. For example, the medicament may contain about 10-80% by weight of active substance, 90-20% by weight of liquid or solid carrier and optionally up to 20% by weight of surface-active substance. Spraying of this agent is carried out in a conventional manner, for example, using water as a carrier at a spray volume of about 100 to 1000/ha. It is likewise possible to apply this drug in the so-called low-volume or ultra-low-volume method, as well as in the form of so-called microgranules. For the preparation of the preparation, the following ingredients are used, for example: A. Spraying powder (a) Active substances 80% by weight Kaolin 15% by weight Surfactants (based on the sodium salt of N-methyl-N-oleyl-taurine and the calcium salt of ligninsulfonic acid) 5% by weight (b) Active substances 50% by weight Clay minerals 40% by weight Serpitz 5% by weight Surfactants (based on mixtures of calcium salts of lignosulfonic acid and alkylphenol polyglycol ethers) 5% by weight (c) Active substances 20% by weight Clay Minerals 70% by weight Serpitz 5% by weight Surfactants (based on a mixture of calcium salts of lignosulfonic acid and alkylphenol polyglycol ethers) 5% by weight (d) Active substances 5% by weight Tonesil 80% by weight Serpitz 10% by weight % surfactants (based on fatty acid condensation products)
5% by weight B Emulsion concentrate active substance 20% by weight Xylol 40% by weight Dimethyl sulfoxide 35% by weight Nonylphenylpolyoxyethylene or mixture of calcium dodecylbenzenesulfonate
5% by weight C Paste active substance 45% by weight Sodium aluminum silicate 5% by weight Cetyl polyglycol ether with 8 moles of ethylene oxide 15% by weight Spindle oil 2% by weight Polyethylene glycol 10% by weight Water 23 parts The new compounds according to the invention can be used, for example, in general formula It is produced by reacting the compound [wherein Z represents the above] with a carboxylic acid anhydride, optionally in the presence of a catalyst, and isolating the desired target compound by a method known per se. The starting material 28-methyl-bratusinolide is prepared, for example, from stigmamasterin, as described in Steroids Vol. 39, p. 89 (1982). The following examples provide details regarding the preparation of the compounds of the present invention. Example 1 2α・3α・22S・23S-tetrahydroxy-
1 g of 24-ethyl-7-oxa-B-homo-5α-cholestan-6-one was dissolved in 10 ml of pyridine, cooled to 0°C, and 0.5 ml of acetic anhydride was added.
Stir at 0°C for 5.5 hours. Thereafter, it is precipitated out in ice water, the product is filtered off with suction, washed with water, dried and chromatographed on silica gel. After recrystallization from acetone/hexane, 2α-acetoxy-3α・22S・23S− has a melting point of 125°C.
Trihydroxy-24-ethyl-7-oxa-B-
810 mg of homo-5α-cholestan-6-one are obtained. Example 2 2α・3α・22S・23S-tetrahydroxy-
1 g of 24-ethyl-7-oxa-B-homo-5α-cholestan-6-one was dissolved in 10 ml of pyridine, cooled to 0°C, mixed with 1 ml of acetic anhydride and heated to 0°C.
Stir for 7 hours. After that, it was precipitated in ice water,
Filter with suction, wash with water and dry. After chromatography on silica gel (gradient elution with chloroform/acetone), 2
α・3α-diacetoxy-22S・23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α
- 320 mg of cholestan-6-one and 2 with a melting point of 146°C
α・22S-diacetoxy-3α・23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α
-535 mg of cholestan-6-one are obtained. Example 3 2α・3α・22R・23R-tetrahydroxy-
210 mg of 24-ethyl-7-oxa-B-homo-5α-cholestan-6-one are reacted as described in Example 1. Recrystallization from acetone/hexane gives 2α-acetoxy-3 with a melting point of 246-248°C.
α・22R・23R-trihydroxy-24-ethyl-
7-oxa-B-homo-5α-cholestane-6-
You get 170mg of on. Example 4 (reference example) 2α・3α・22S・23S-tetrahydroxy-
500 mg of 24-ethyl-6-oxa-B-homo-5α-cholestan-7-one are reacted as in Example 1. 2α-acetoxy-3α·22S·23S-trihydroxy-24 with a melting point of 198-200°C after recrystallization from methylene chloride/isopropyl ether.
385 g of -ethyl-6-oxa-B-homo-5α-cholestan-7-one are obtained. Example 5 (reference example) 2α・3α・22S・23S-tetrahydroxy-
1 g of 24-ethyl-6-oxa-B-homo-5α-cholestan-7-one is reacted and separated as described in Example 2. 290 mg of 2α·3α-diacetoxy-22S·23S-dihydroxy-24-ethyl-6-oxa-B-homo-5α-cholestan-7-one with a melting point of 135°C and 2α·22S-diacetoxy-3α·23S with a melting point of 152°C. 560 mg of -dihydroxy-24-ethyl-6-oxa-B-homo-5α-cholestan-7-one are obtained. Example 6 (reference example) 2β・3β・22S・22S-tetrahydroxy-
500 mg of 24-ethyl-7-oxa-B-homo-5α-cholestan-6-one (melting point: 182-183°C) were acetylated as described in Example 1. Melting point 161
3β-acetoxy-2β・22S・23S− at ~162℃
Trihydroxy-24-ethyl-7-oxa-B-
410 mg of homo-5α-cholestan-6-one are obtained. Example 7 2α・3α・22S・23S-tetrahydroxy-
300 mg of 24-ethyl-7-oxa-B-homo-5α-cholestan-6-one are dissolved in 3 ml of pyridine, cooled to 0° C. and mixed with 0.6 ml of valeric anhydride. Stir at 0°C for 10 hours, precipitate in ice water, wash with water and dry. This crude product was chromatographed on silica gel to obtain 2α
-valeryloxy-3α・22S・23S-trihydroxy-24-ethyl-7-oxa-B-homo-5
α-cholestan-6-one is recrystallized from acetone/hexane, melting point 100-105°C. Produced in the same manner (reference): 2α-heptanoyloxy-3α・22R・23R
-trihydroxy-24-ethyl-7-oxa-2
-Homo-5α-cholestan-6-one, melting point: 85
~87℃, 2α-dimethylacetoxy-3α・22S・23S
-trihydroxy-24-ethyl-7-oxa-B
-Homo-5α-cholestan-6-one, melting point:
121-122.5°C, 2α-butyryloxy-3α・22S・23S-trihydroxy-24-ethyl-6-oxa-B-homo-5α-cholestan-7-one, melting point: 92-94
°C, 2α-diethylacetoxy-3α・22S・23S
-trihydroxy-24-ethyl-7-oxa-B
-Homo-5α-cholestan-6-one, melting point:
113-115℃. Example 8 (reference example) 2α・3α・22S・23S-tetrahydroxy-
300 mg of 24-ethyl-7-oxa-B-homo-5α-cholestan-6-one are dissolved in 3 ml of pyridine, cooled to 0° C. and 1 ml of valeric anhydride is added.
Stir at 0° C. for 20 hours, precipitate in ice water, wash with water and dry. After chromatography on silica gel (gradient elution with chloroform/acetone), 2α·3α-divaleryloxy-22S·23S-dihydroxy-24- with a melting point of 109-111 °C
120 mg of ethyl-7-oxa-B-homo-5α-cholestan-6-one and 2 with a melting point of 128.5-130°C
α・22S-Divaleryloxy-3α・23S-dihydroxy-24-ethyl-7-oxa-B-homo-
160 mg of 5α-cholestan-6-one are obtained. Similarly, the following is produced: 2α・3α-dihexanoyloxy-22S・
23S-dihydroxy-24-ethyl-7-oxa-
B-homo-5α-cholestan-6-one, melting point:
88~90℃ 2α・22S-dihexanoyloxy-3α・
23S-dihydroxy-24-ethyl-7-oxa-
B-homo-5α-cholestan-6-one, melting point:
117-120℃. Example 9 (reference) 2α・3α・22R・23R-tetrahydroxy-
500 mg of 24-ethyl-7-oxa-B-homo-5α-cholestan-6-one was dissolved in 5 ml of pyridine, cooled to 0°C, 0.3 ml of ethoxyacetic anhydride was added, and the mixture was heated at -5 to 0°C for 6 hours. Stir. After treatment and isolation as in Example 1, 2α-ethoxyacetoxy-3α·22R·23R-trihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one, m.p. 182-185 °C, 310 mg is obtained. Example 10 (reference example) 2α・3α・22S・23S-tetrahydroxy-
1 g of 24-ethyl-7-oxa-B-homo-5α-cholestan-6-one was added to 100 g of tetrahydrofuran.
ml and 0.5 ml of boron trifluoride ether complex compound in 100 ml of acetone and stirred at -5 to 0°C for 30 minutes. After addition of 1 ml of pyridine, it is concentrated in vacuo, precipitated with water, filtered off with suction and washed with water.
After recrystallization from acetone, 2α·3α-isopropylidenedioxy-22S· with a melting point of 198–201°C.
23S-dihydroxy-24-ethyl-7-oxa-
731 mg of B-homo-5α-cholestan-6-one are obtained. The following is produced in the same way: 2α・3α-isopropylidenedioxy-22S
-23S-dihydroxy-24-ethyl-6-oxa-B-homo-5α-cholestan-7-one, melting point: 211-213°C, 2β・3β-isopropylidenedioxy-
22S/23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one,
Melting point: 189-191℃. Example 11 (reference example) 2α・3α・22S・23S-tetrahydroxy-
1 g of 24-ethyl-7-oxa-B-homo-5α-cholestan-6-one is mixed with 1.5 ml of triethylorthoacetate and 5 mg of p-toluolsulfonic acid in 100 ml of benzene and stirred for 30 minutes at room temperature. After adding 2 drops of pyridine, concentrate in vacuo, dilute with methylene chloride, wash with water and concentrate. When the crude product is triturated with isopropyl ether, the amorphous 2α・3α-(1-ethoxyethylenedioxy)-22S・23S-dihydroxy-24
720 mg of -ethyl-7-oxa-B-homo-5α-cholestan-6-one are obtained as a diastereomeric mixture. Similarly, the following is obtained: 2α·3α-(1-ethoxy-propylidenedioxy)-22S·23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestane-6
-one, amorphous, 2α・3α-(1-methoxy-methylenedioxy)-22R・23R-dihydroxy-24-ethyl-7
-Oxa-B-homo-5α-cholestan-6-one, melting point: 96-99°C, 2β・3β-(1-ethoxy-ethylenedioxy)-22S・23S-dihydroxy-24-ethyl-7
-Oxa-B-homo-5α-cholestan-6-one, melting point: 84-87°C. Example 12 (reference example) 2α・3α・22S・23S-tetrahydroxy-
200 mg of 24-ethyl-7-oxa-B-homo-5α-cholestan-6-one are mixed with 0.01 ml of 72% perchloric acid in 2 ml of acetophenone and stirred for 16 hours at room temperature. Subsequently, 0.1 ml of pyridine is added and chromatographed on silica gel. Gradient elution with toluene/acetate gave the amorphous 2α·3α-(1-methyl-l-phenyl-methylenedioxy)-22S·23S-dihydroxy-24
120 mg of -ethyl-7-oxa-B-homo-5α-cholestan-6-one are obtained as a diastereomeric mixture. The following is produced in the same way: 2α·3α-(1-methyl-1-phenyl-methylenedioxy)-22S·23S-dihydroxy-24
-Ethyl-6-oxa-B-homo-5α-cholestan-7-one. Example 13 (reference example) 2α・3α-22S・23S-tetrahydroxy-
200 mg of 24-ethyl-6-oxa-B-homo-5α-cholestan-7-one are heated in 7 ml of diethyl carbonate and 2 ml of tetrahydrofuran to 15 mg of sodium methylate and then heated to 130° C. (bath temperature) for 2.5 hours. After cooling, neutralize with acetic acid and concentrate in vacuo. Dissolve the residue in chloroform/acetone and
Filter on silica gel and concentrate the filtrate. By recrystallization from acetone/hexane, 2α·3α-carbonyldioxy-22S·23S-dihydroxy-24-ethyl-, melting point: 242.5-244°C.
6-oxa-B-homo-5α-cholestane-7-
You get 155mg of on. Similarly, the following can be obtained: 2α・3α-carbonyldioxy-22R・23R
-dihydroxy-24-ethyl-6-oxa-B-
Homo-5α-cholestan-7-one, melting point: 216
~217℃ Example 14 (Reference example) 2α・3α・22S・23S-Tetrahydroxy-
200 mg of 24-ethyl-6-oxa-B-homo-5α-cholestan-7-one was added to 4 ml of tetrahydrofuran.
ml, add 1 ml of benzylaldehyde,
Cool to -15 °C and 0.2 ml of perchloric acid solution (made from 0.5 ml of 70% perchloric acid in 1.5 ml of tetrahydrofuran).
Add. Stir for 15 minutes at −15° C., neutralize with pyridine, dilute with chloroform and chromatograph on silica gel. 153 mg of amorphous 2α·3α-benzylidenedioxy-22S·23S-dihydroxy-24-ethyl-6-oxa-B-homo-5α-cholestan-7-one are eluted with chloroform/acetone (1:1). Similarly, the following is obtained: 2α・3α-benzylidenedioxy-22R・
23R-dihydroxy-24-ethyl-7-oxa-
B-homo-5α-cholestan-6-one, 2α・3α-benzylidenedioxy-22S・
23S-dihydroxy-24-ethyl-7-oxa-
B-homo-5α-cholestan-6-one. The compounds according to the invention are generally colorless, odorless, crystalline substances that are sparingly soluble in water, soluble to some extent in aliphatic hydrocarbons such as petroleum ether, hexane, pentane and cyclohexane, chloroform, chloride, etc. halogenated hydrocarbons such as methylene, carbon tetrachloride, aromatic hydrocarbons such as benzole, toluol and xylol, ethers such as diethyl ether, tetrahydrofuran and dioxane, carboxylic acid nitriles such as acetonitrile, ketones such as acetone,
alcohols, such as methanol and ethanol;
It is readily soluble in carboxylic acid amides such as dimethylformamide and sulfoxides such as dimethyl sulfoxide. The following examples detail the possible use of the compounds of the invention in the abovementioned dosage forms. Example 15 Growth promotion in hanging legumes Hanging legumes of the species “Pinto” were grown in an air-conditioned room at 25°C and 90% air humidity, with high intensity in the 660 nm range and extremely high intensity in the 730 nm range. Cultivate under the action of light with a low part. Compounds 10 and 50 to be tested after 6 days of cultivation
μg is dissolved in a solvent and loaded onto the growing second internodes. Three days after application, measure the elongation of the internodes and compare the elongation rate with the control. The results are listed in the table below.
【表】
〓オン
[Table] 〓On
【表】
これにより、本発明による化合物が記載した試
験条件下に比較薬剤及びコントロールより強い伸
びに作用することがわかつた。
これに対し比較薬剤は多かれ少なかれ太さの生
長にのみ強く作用し、1部は節間の縮少に導く。
例 16
キユウリにおける生長抑制
キユウリの種子を温室条件下に0.01重量%の濃
度の試験化合物の水性懸濁液中で発芽させる。
6日後、発芽した植物の根及び芽の長さを測定
する。
次の表に実験の結果をパーセンテージで表わし
た。[Table] This shows that the compounds according to the invention exert a stronger elongation effect than the comparative drugs and the control under the test conditions described. On the other hand, comparative drugs have a more or less strong effect only on the growth of thickness, and some of them lead to reduction of internodes. Example 16 Growth inhibition in cucumber cucumber seeds are germinated under greenhouse conditions in an aqueous suspension of the test compound at a concentration of 0.01% by weight. After 6 days, the root and shoot lengths of the germinated plants are measured. The results of the experiment are expressed in percentages in the following table.
【表】
この実験法においては明らかに本発明による化
合物は生長抑制に働らく。[Table] In this experimental method, the compounds according to the invention clearly act to inhibit growth.
Claims (1)
はアセチル基を表わし、R22は水素又はアセチル
基を表わし、かつR3及びR22は同時にアセチル基
を表わさない]の28−メチル−ブラツシノリド誘
導体。 2 2α−アセトキシ−3α・22S・23S−トリ
ヒドロキシ−24−エチル−7−オキサ−B−ホモ
−5α−コレスタン−6−オンである特許請求の
範囲第1項記載の化合物。 3 2α・22S−ジアセトキシ−3α・23S−ジ
ヒドロキシ−24−エチル−7−オキサ−B−ホモ
−5α−コレスタン−6−オンである特許請求の
範囲第1項記載の化合物。 4 2α−アセトキシ−3α・22R・23R−トリ
ヒドロキシ−24−エチル−7−オキサ−B−ホモ
−5α−コレスタン−6−オンである特許請求の
範囲第1項記載の化合物。 5 2α−バレリルオキシ−3α・22S・23S−
トリヒドロキシ−24−エチル−7−オキサ−B−
ホモ−5α−コレスタン−6−オンである特許請
求の範囲第1項記載の化合物。 6 2α・3α−ジアセトキシ−22S・23S−ジ
ヒドロキシ−24−エチル−7−オキサ−B−ホモ
−5α−コレスタン−6−オンでンである特許請
求の範囲第1項記載の化合物。 7 一般式 [式中、Zは基【式】を表わし、R2は アセチル又はバレリル基を表わし、R3は水素又
はアセチル基を表わし、R22は水素又はアセチル
基を表わし、かつR3及びR22は同時にアセチル基
を表わさない]の28−メチル−ブラツシノリド誘
導体を製造するために、一般式 [式中、Zは前記のものを表わす]の化合物を場
合により触媒の存在下に無水カルボン酸と反応さ
せ、所望の目的化合物を自体公知法で単離するこ
とを特徴とする28−メチル−ブラツシノリド誘導
体の製法。 8 一般式 [式中、Zは基【式】を表わし、R2は アセチル又はバレリル基を表わし、R3は水素又
はアセチル基を表わし、R22は水素又はアセチル
基を表わし、かつR3及びR22は同時にアセチル基
を表わさない]の28−メチル−ブラツシノリド誘
導体を少なくとも1種含有することを特徴とする
植物生長調節作用を有する薬剤。 9 担持物質及び/又は助剤と混合した特許請求
の範囲第8項記載の薬剤。 10 豆科植物、特に大豆の増殖的及び発生的生
長に影響を与える特許請求の範囲第8項又は第9
項に記載の薬剤。[Claims] 1. General formula [In the formula, Z represents a group [formula], R 2 represents an acetyl or valeryl group, R 3 represents hydrogen or an acetyl group, R 22 represents hydrogen or an acetyl group, and R 3 and R 22 are 28-methyl-bratsinolide derivatives which do not simultaneously express an acetyl group. The compound according to claim 1, which is 22α-acetoxy-3α·22S·23S-trihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one. 3. The compound according to claim 1, which is 2α·22S-diacetoxy-3α·23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one. 4. The compound according to claim 1, which is 2α-acetoxy-3α·22R·23R-trihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one. 5 2α-valeryloxy-3α・22S・23S−
Trihydroxy-24-ethyl-7-oxa-B-
The compound according to claim 1, which is homo-5α-cholestan-6-one. 6. The compound according to claim 1, which is 2α·3α-diacetoxy-22S·23S-dihydroxy-24-ethyl-7-oxa-B-homo-5α-cholestan-6-one. 7 General formula [In the formula, Z represents a group [formula], R 2 represents an acetyl or valeryl group, R 3 represents hydrogen or an acetyl group, R 22 represents hydrogen or an acetyl group, and R 3 and R 22 are In order to produce a 28-methyl-bratusinolide derivative with the general formula 28-methyl-, which is characterized by reacting the compound [wherein Z represents the above] with a carboxylic anhydride, optionally in the presence of a catalyst, and isolating the desired target compound by a method known per se. Method for producing brassynolide derivatives. 8 General formula [In the formula, Z represents a group [formula], R 2 represents an acetyl or valeryl group, R 3 represents hydrogen or an acetyl group, R 22 represents hydrogen or an acetyl group, and R 3 and R 22 are 1. A drug having a plant growth regulating action, characterized in that it contains at least one 28-methyl-bratusinolide derivative which does not simultaneously express an acetyl group. 9. The drug according to claim 8 mixed with a carrier substance and/or an auxiliary agent. 10 Claims 8 or 9 affecting the reproductive and developmental growth of leguminous plants, especially soybeans
Drugs listed in section.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19823234606 DE3234606A1 (en) | 1982-09-15 | 1982-09-15 | 28-METHYL BRASSINOSTEROID DERIVATIVES, METHOD FOR THE PRODUCTION OF THESE COMPOUNDS AND THEIR CONTAINING AGENTS WITH GROWTH REGULATORY EFFECT FOR PLANTS |
DE3234606.9 | 1982-09-15 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5955880A JPS5955880A (en) | 1984-03-31 |
JPS627195B2 true JPS627195B2 (en) | 1987-02-16 |
Family
ID=6173537
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP58130372A Granted JPS5955880A (en) | 1982-09-15 | 1983-07-19 | 28-methyl-brassinolide derivative, manufacture and plant growth regulant drug |
Country Status (27)
Country | Link |
---|---|
JP (1) | JPS5955880A (en) |
KR (1) | KR840005737A (en) |
AU (1) | AU1865583A (en) |
BE (1) | BE897759A (en) |
CH (1) | CH655730A5 (en) |
DD (1) | DD213346A5 (en) |
DE (1) | DE3234606A1 (en) |
DK (1) | DK420383A (en) |
ES (1) | ES525034A0 (en) |
FI (1) | FI833253A (en) |
FR (1) | FR2532942B1 (en) |
GB (1) | GB2127022B (en) |
GR (1) | GR78758B (en) |
HU (1) | HU189336B (en) |
IL (1) | IL69700A (en) |
IT (1) | IT1164378B (en) |
LU (1) | LU85001A1 (en) |
NL (1) | NL8302426A (en) |
NO (1) | NO833296L (en) |
PL (1) | PL136535B1 (en) |
PT (1) | PT77259B (en) |
RO (1) | RO88035A (en) |
SE (1) | SE8304944L (en) |
TR (1) | TR21879A (en) |
YU (1) | YU169783A (en) |
ZA (1) | ZA836870B (en) |
ZW (1) | ZW19583A1 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0322639B1 (en) * | 1987-12-24 | 1992-05-20 | Fujisawa Pharmaceutical Co., Ltd. | (22r,23r,24s)-22,23-epoxy-2 alpha, 3 alpha-isopropylidenedioxy-b-homo-7-oxa-5 alpha-stigmastan-6-one, process for preparation thereof and plant growth regulating composition containing the same |
CN1042431C (en) * | 1993-06-01 | 1999-03-10 | 玉生化学株式会社 | Brassinosteroid derivatives and plant growth regulator containing the same |
US6239073B1 (en) | 1999-03-30 | 2001-05-29 | Exelixis Plant Sciences, Inc. | Brassinosteroid analogs useful as plant growth regulators |
JP2001335406A (en) * | 2000-05-25 | 2001-12-04 | Inst Of Physical & Chemical Res | Plant growth regulator |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6017794B2 (en) * | 1980-05-16 | 1985-05-07 | ア−ス製薬株式会社 | New steroids |
JPS5890578A (en) * | 1981-11-24 | 1983-05-30 | Sumitomo Chem Co Ltd | Novel steroid, its preparation and plant growth regulator containing the same |
-
1982
- 1982-09-15 DE DE19823234606 patent/DE3234606A1/en not_active Withdrawn
-
1983
- 1983-07-07 NL NL8302426A patent/NL8302426A/en not_active Application Discontinuation
- 1983-07-19 JP JP58130372A patent/JPS5955880A/en active Granted
- 1983-08-05 IT IT22439/83A patent/IT1164378B/en active
- 1983-08-15 YU YU01697/83A patent/YU169783A/en unknown
- 1983-08-19 ES ES525034A patent/ES525034A0/en active Granted
- 1983-08-26 PT PT77259A patent/PT77259B/en unknown
- 1983-09-02 AU AU18655/83A patent/AU1865583A/en not_active Abandoned
- 1983-09-09 TR TR21879A patent/TR21879A/en unknown
- 1983-09-12 FI FI833253A patent/FI833253A/en not_active Application Discontinuation
- 1983-09-12 IL IL69700A patent/IL69700A/en unknown
- 1983-09-12 RO RO83112036A patent/RO88035A/en unknown
- 1983-09-12 PL PL1983243720A patent/PL136535B1/en unknown
- 1983-09-12 GB GB08324348A patent/GB2127022B/en not_active Expired
- 1983-09-13 DD DD83254774A patent/DD213346A5/en unknown
- 1983-09-13 CH CH4992/83A patent/CH655730A5/en not_active IP Right Cessation
- 1983-09-13 GR GR72434A patent/GR78758B/el unknown
- 1983-09-14 LU LU85001A patent/LU85001A1/en unknown
- 1983-09-14 HU HU833190A patent/HU189336B/en unknown
- 1983-09-14 BE BE0/211537A patent/BE897759A/en not_active IP Right Cessation
- 1983-09-14 NO NO833296A patent/NO833296L/en unknown
- 1983-09-14 SE SE8304944A patent/SE8304944L/en not_active Application Discontinuation
- 1983-09-14 KR KR1019830004316A patent/KR840005737A/en not_active Application Discontinuation
- 1983-09-15 DK DK420383A patent/DK420383A/en not_active Application Discontinuation
- 1983-09-15 ZW ZW195/83A patent/ZW19583A1/en unknown
- 1983-09-15 FR FR8314672A patent/FR2532942B1/en not_active Expired
- 1983-09-15 ZA ZA836870A patent/ZA836870B/en unknown
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