NO833296L - 28-methyl-brassinosteroidderivater og midler med vekstregulerende virkning paa planter inneholdende disse forbindelser - Google Patents

28-methyl-brassinosteroidderivater og midler med vekstregulerende virkning paa planter inneholdende disse forbindelser

Info

Publication number: NO833296L
Authority: NO; Norway
Prior art keywords: oxa; ethyl; homo; cholestan; dihydroxy
Prior art date: 1982-09-15

Application number

NO833296A

Other languages

English (en)

Norwegian (no)

Inventor

Ulrich Kerb

Ulrich Eder

Hansjoerg Kraehmer

Original Assignee

Schering Ag

Priority date (The priority date 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 date listed.)

1982-09-15

Filing date

1983-09-14

Publication date

1984-03-16

1983-09-14 Application filed by Schering Ag filed Critical Schering Ag

1984-03-16 Publication of NO833296L publication Critical patent/NO833296L/no

Links

150000001875 compounds Chemical class 0.000 title claims description 24
230000001105 regulatory effect Effects 0.000 title 1
-1 triethyl orthoacetic acid ester Chemical class 0.000 claims description 22
241000196324 Embryophyta Species 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
125000002252 acyl group Chemical group 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 10
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 6
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 6
230000012010 growth Effects 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 2
235000010469 Glycine max Nutrition 0.000 claims description 2
244000068988 Glycine max Species 0.000 claims description 2
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
235000021374 legumes Nutrition 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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
239000000047 product Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
239000013543 active substance Substances 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
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000004094 surface-active agent Substances 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000000969 carrier Substances 0.000 description 4
OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 4
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000000243 solution 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
239000004927 clay Substances 0.000 description 3
235000013399 edible fruits Nutrition 0.000 description 3
238000010828 elution Methods 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
239000004009 herbicide Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
244000045561 useful plants Species 0.000 description 3
239000008096 xylene Substances 0.000 description 3
239000005995 Aluminium silicate Substances 0.000 description 2
240000008067 Cucumis sativus Species 0.000 description 2
241001300479 Macroptilium Species 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-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
159000000007 calcium salts Chemical class 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000002734 clay mineral Substances 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
150000002170 ethers Chemical class 0.000 description 2
229940052303 ethers for general anesthesia Drugs 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
239000005648 plant growth regulator Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
150000003431 steroids Chemical class 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
230000009105 vegetative growth Effects 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
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 1
125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 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
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 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
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
235000009849 Cucumis sativus Nutrition 0.000 description 1
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
244000286663 Ficus elastica Species 0.000 description 1
206010053759 Growth retardation Diseases 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
229920003171 Poly (ethylene oxide) Polymers 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
NLDBCFRIELDMRO-UHFFFAOYSA-N Stigmasterin Natural products CCCC(CC)C=CC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C NLDBCFRIELDMRO-UHFFFAOYSA-N 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
235000013832 Valeriana officinalis Nutrition 0.000 description 1
244000126014 Valeriana officinalis Species 0.000 description 1
239000000654 additive Substances 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
150000008064 anhydrides Chemical class 0.000 description 1
230000002180 anti-stress Effects 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
239000011230 binding agent Substances 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
150000001647 brassinosteroids Chemical class 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 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
HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000035613 defoliation Effects 0.000 description 1
229960004132 diethyl ether Drugs 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
230000005089 fruit drop Effects 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
230000035784 germination Effects 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000009422 growth inhibiting effect Effects 0.000 description 1
230000009036 growth inhibition Effects 0.000 description 1
231100000001 growth retardation Toxicity 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000003306 harvesting Methods 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
230000005764 inhibitory process Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 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
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
239000012528 membrane Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 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 class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
231100001184 nonphytotoxic Toxicity 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 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
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
230000035699 permeability Effects 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011814 protection agent Substances 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
239000002689 soil Substances 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
HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 1
BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000016788 valerian Nutrition 0.000 description 1
238000010626 work up procedure Methods 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
Wood Science & Technology (AREA)
Insects & Arthropods (AREA)
Environmental Sciences (AREA)
Steroid Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pyrane Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (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)

NO833296A 1982-09-15 1983-09-14 28-methyl-brassinosteroidderivater og midler med vekstregulerende virkning paa planter inneholdende disse forbindelser NO833296L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19823234606 DE3234606A1 (de)	1982-09-15	1982-09-15	28-methyl-brassinosteroid-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit wachstumsregulatorischer wirkung fuer pflanzen

Publications (1)

Publication Number	Publication Date
NO833296L true NO833296L (no)	1984-03-16

Family

ID=6173537

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO833296A NO833296L (no)	1982-09-15	1983-09-14	28-methyl-brassinosteroidderivater og midler med vekstregulerende virkning paa planter inneholdende disse forbindelser

Country Status (27)

Country	Link
JP (1)	JPS5955880A (ro)
KR (1)	KR840005737A (ro)
AU (1)	AU1865583A (ro)
BE (1)	BE897759A (ro)
CH (1)	CH655730A5 (ro)
DD (1)	DD213346A5 (ro)
DE (1)	DE3234606A1 (ro)
DK (1)	DK420383A (ro)
ES (1)	ES525034A0 (ro)
FI (1)	FI833253A (ro)
FR (1)	FR2532942B1 (ro)
GB (1)	GB2127022B (ro)
GR (1)	GR78758B (ro)
HU (1)	HU189336B (ro)
IL (1)	IL69700A (ro)
IT (1)	IT1164378B (ro)
LU (1)	LU85001A1 (ro)
NL (1)	NL8302426A (ro)
NO (1)	NO833296L (ro)
PL (1)	PL136535B1 (ro)
PT (1)	PT77259B (ro)
RO (1)	RO88035A (ro)
SE (1)	SE8304944L (ro)
TR (1)	TR21879A (ro)
YU (1)	YU169783A (ro)
ZA (1)	ZA836870B (ro)
ZW (1)	ZW19583A1 (ro)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3871355D1 (de) *	1987-12-24	1992-06-25	Fujisawa Pharmaceutical Co	(22r,23r,24s)-22,23-epoxy-2-alpha, 3-alpha-isopropylidendioxy-b-homo-7-oxa 5-alpha-stigmastan-6-on, verfahren zu dessen herstellung und pflanzenwachstumsregulierende zusammensetzungen, die sie enthalten.
WO1994028011A1 (fr) *	1993-06-01	1994-12-08	Tama Biochemical Co., Ltd.	Derives brassinosteroidiens et regulateur de la croissance vegetale contenant ces derives
US6239073B1 (en) *	1999-03-30	2001-05-29	Exelixis Plant Sciences, Inc.	Brassinosteroid analogs useful as plant growth regulators
JP2001335406A (ja) *	2000-05-25	2001-12-04	Inst Of Physical & Chemical Res	植物成長調節剤

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6017794B2 (ja) *	1980-05-16	1985-05-07	ア−ス製薬株式会社	新規ステロイド類
JPS5890578A (ja) *	1981-11-24	1983-05-30	Sumitomo Chem Co Ltd	新規ステロイド類の製造法

1982
- 1982-09-15 DE DE19823234606 patent/DE3234606A1/de not_active Withdrawn
1983
- 1983-07-07 NL NL8302426A patent/NL8302426A/nl not_active Application Discontinuation
- 1983-07-19 JP JP58130372A patent/JPS5955880A/ja active Granted
- 1983-08-05 IT IT22439/83A patent/IT1164378B/it active
- 1983-08-15 YU YU01697/83A patent/YU169783A/xx unknown
- 1983-08-19 ES ES525034A patent/ES525034A0/es active Granted
- 1983-08-26 PT PT77259A patent/PT77259B/pt unknown
- 1983-09-02 AU AU18655/83A patent/AU1865583A/en not_active Abandoned
- 1983-09-09 TR TR21879A patent/TR21879A/xx unknown
- 1983-09-12 IL IL69700A patent/IL69700A/xx unknown
- 1983-09-12 PL PL1983243720A patent/PL136535B1/pl unknown
- 1983-09-12 RO RO83112036A patent/RO88035A/ro unknown
- 1983-09-12 GB GB08324348A patent/GB2127022B/en not_active Expired
- 1983-09-12 FI FI833253A patent/FI833253A/fi not_active Application Discontinuation
- 1983-09-13 CH CH4992/83A patent/CH655730A5/de not_active IP Right Cessation
- 1983-09-13 GR GR72434A patent/GR78758B/el unknown
- 1983-09-13 DD DD83254774A patent/DD213346A5/de unknown
- 1983-09-14 SE SE8304944A patent/SE8304944L/ not_active Application Discontinuation
- 1983-09-14 BE BE0/211537A patent/BE897759A/fr not_active IP Right Cessation
- 1983-09-14 HU HU833190A patent/HU189336B/hu unknown
- 1983-09-14 LU LU85001A patent/LU85001A1/de unknown
- 1983-09-14 KR KR1019830004316A patent/KR840005737A/ko not_active Application Discontinuation
- 1983-09-14 NO NO833296A patent/NO833296L/no unknown
- 1983-09-15 ZA ZA836870A patent/ZA836870B/xx unknown
- 1983-09-15 ZW ZW195/83A patent/ZW19583A1/xx unknown
- 1983-09-15 DK DK420383A patent/DK420383A/da not_active Application Discontinuation
- 1983-09-15 FR FR8314672A patent/FR2532942B1/fr not_active Expired

Also Published As

Publication number	Publication date
SE8304944L (sv)	1984-03-16
RO88035B (ro)	1985-10-31
BE897759A (fr)	1984-03-14
YU169783A (en)	1986-02-28
PL136535B1 (en)	1986-02-28
PT77259B (de)	1986-02-04
FR2532942B1 (fr)	1986-04-25
ES8404695A1 (es)	1984-05-16
IL69700A0 (en)	1983-12-30
ZW19583A1 (en)	1983-12-21
GB8324348D0 (en)	1983-10-12
CH655730A5 (de)	1986-05-15
IT1164378B (it)	1987-04-08
TR21879A (tr)	1985-10-03
HU189336B (en)	1986-06-30
PL243720A1 (en)	1984-07-30
NL8302426A (nl)	1984-04-02
IT8322439A0 (it)	1983-08-05
KR840005737A (ko)	1984-11-16
FI833253A0 (fi)	1983-09-12
DK420383D0 (da)	1983-09-15
IL69700A (en)	1987-02-27
SE8304944D0 (sv)	1983-09-14
PT77259A (de)	1983-09-01
DK420383A (da)	1984-03-16
JPS5955880A (ja)	1984-03-31
AU1865583A (en)	1984-03-22
DD213346A5 (de)	1984-09-12
FR2532942A1 (fr)	1984-03-16
ZA836870B (en)	1984-05-30
ES525034A0 (es)	1984-05-16
RO88035A (ro)	1985-11-30
JPS627195B2 (ro)	1987-02-16
LU85001A1 (de)	1984-03-16
GB2127022A (en)	1984-04-04
DE3234606A1 (de)	1984-03-15
FI833253A (fi)	1984-03-16
GB2127022B (en)	1986-02-05
GR78758B (ro)	1984-10-02

Publication	Publication Date	Title
HU206595B (en)	1992-12-28	Herbicide composition containing salicylic acid derivatives or sulfur analogue of them as active component and growth controlling composition containing salicylic acid derivatives and process for producing the new active components
JPS59205368A (ja)	1984-11-20	殺微生物剤
NO146910B (no)	1982-09-20	Acetanilider med herbicid virkning
EP0142741B1 (de)	1990-01-24	Cyclohexan-1,3-dionderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
EP0177450B1 (de)	1989-03-29	Verfahren zur Herstellung von Cyclohexandion-carbonsäurederivaten mit herbizider und das Pflanzenwachstum regulierender Wirkung
EP0107156B1 (de)	1986-12-30	Cyclohexan-1,3-dionderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
EP0156773B1 (de)	1989-09-06	Cyclohexenon-carbonsäurederivate mit herbizider und das Pflanzenwachstum regulierender Wirkung
NO833296L (no)	1984-03-16	28-methyl-brassinosteroidderivater og midler med vekstregulerende virkning paa planter inneholdende disse forbindelser
US4961775A (en)	1990-10-09	Brassinosteroid derivatives and plant growth regulators
CA1289560C (en)	1991-09-24	Cyclohexenone derivatives, the preparation and use thereof as herbicides and plant growth regulators
US3503732A (en)	1970-03-31	Combating weeds with o-acyl-3,5-dialkyl-4-hydroxybenzaldoximes
US4591650A (en)	1986-05-27	Hexanor-brassinolid-22-ethers
DE2842801A1 (de)	1980-04-10	Beta-triazolyloxime
NO833295L (no)	1984-03-16	Brassinosteroidderivater og middel for vekstregulerende virkning paa planter inneholdende disse forbindelser
JP2872688B2 (ja)	1999-03-17	テトラヒドロピラン−２，４−ジオン、該化合物を含有する除草剤および望ましからぬ植物成長を防除する方法
NO751355L (ro)	1975-10-21
US3644524A (en)	1972-02-22	Combating weeds with o-acyl-3 5-dialkyl-4-hydroxybenzaldoximes
EP0249858B1 (de)	1990-12-05	Fluoralkylsubstituierte Chinolinderivate. ihre Herstellung sowie Verwendung zur Bekämpfung unerwünschten Pflanzenwachstums
EP0035475A1 (de)	1981-09-09	Herbizid wirkende 2-Nitro-5-phenoxyphenyl-oxazole, -oxazine, -imidazole, -pyrimidine und -thiazole, ihre Herstellung und Verwendung
US3388991A (en)	1968-06-18	Method of controlling undesired vegetation with polychlorophenyl nu-allyl-nu-cyclohexylcarbamates
EP0345637A1 (de)	1989-12-13	N-substituierte 3,4,5,6-Tetrahydrophthalimid-Derivate
SU759046A3 (ru)	1980-08-23	Гербицидна композици
NO147603B (no)	1983-01-31	1,3,3-trimethyl-6-azabicyclo-(3,2,1)-octan-6-thiocarboxylsyre-s-estere med herbicid virkning
JPH0853432A (ja)	1996-02-27	クロトン酸メチル誘導体及び該誘導体を有効成分とする除草剤
DE3502391A1 (de)	1986-02-27	Cyclohexenonderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses