KR100232484B1 - 에폭시 시클로헥산 유도체 및 식물성장조절제 - Google Patents
에폭시 시클로헥산 유도체 및 식물성장조절제 Download PDFInfo
- Publication number
- KR100232484B1 KR100232484B1 KR1019970701685A KR19970701685A KR100232484B1 KR 100232484 B1 KR100232484 B1 KR 100232484B1 KR 1019970701685 A KR1019970701685 A KR 1019970701685A KR 19970701685 A KR19970701685 A KR 19970701685A KR 100232484 B1 KR100232484 B1 KR 100232484B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- plant growth
- alkyl group
- growth regulator
- compound
- Prior art date
Links
- 239000005648 plant growth regulator Substances 0.000 title claims abstract description 27
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical class C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 31
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 19
- 230000008635 plant growth Effects 0.000 claims abstract description 11
- -1 polymethylene group Polymers 0.000 claims abstract description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 6
- 239000004480 active ingredient Substances 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 230000012010 growth Effects 0.000 claims description 16
- 235000013399 edible fruits Nutrition 0.000 claims description 11
- 239000007952 growth promoter Substances 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 230000035784 germination Effects 0.000 claims description 8
- 230000005068 transpiration Effects 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 5
- 239000003623 enhancer Substances 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 abstract description 18
- IXVMHGVQKLDRKH-YEJCTVDLSA-N (22s,23s)-epibrassinolide 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-YEJCTVDLSA-N 0.000 abstract description 8
- 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 abstract description 8
- 230000002195 synergetic effect Effects 0.000 abstract description 7
- 230000035800 maturation Effects 0.000 abstract description 6
- 230000003389 potentiating effect Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 64
- 238000012360 testing method Methods 0.000 description 25
- 239000000203 mixture Substances 0.000 description 22
- 241000196324 Embryophyta Species 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 101000993347 Gallus gallus Ciliary neurotrophic factor Proteins 0.000 description 8
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 210000004209 hair Anatomy 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 230000033228 biological regulation Effects 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- FCRACOPGPMPSHN-UHFFFAOYSA-N desoxyabscisic acid Natural products OC(=O)C=C(C)C=CC1C(C)=CC(=O)CC1(C)C FCRACOPGPMPSHN-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 230000001766 physiological effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000001647 brassinosteroids Chemical class 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000001737 promoting effect Effects 0.000 description 4
- 230000007226 seed germination Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 244000088415 Raphanus sativus Species 0.000 description 3
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 3
- 241000219094 Vitaceae Species 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 235000021021 grapes Nutrition 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 3
- 239000010455 vermiculite Substances 0.000 description 3
- 235000019354 vermiculite Nutrition 0.000 description 3
- 229910052902 vermiculite Inorganic materials 0.000 description 3
- 235000005254 Allium ampeloprasum Nutrition 0.000 description 2
- 240000006108 Allium ampeloprasum Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- 244000000626 Daucus carota Species 0.000 description 2
- 235000002767 Daucus carota Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 235000013405 beer Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000035040 seed growth Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- UYONLYLBVJEYMU-UHFFFAOYSA-N 3-bromobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC(Br)=C1 UYONLYLBVJEYMU-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 241000332371 Abutilon x hybridum Species 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 229930192334 Auxin Natural products 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- IFTRQJLVEBNKJK-UHFFFAOYSA-N CCC1CCCC1 Chemical compound CCC1CCCC1 IFTRQJLVEBNKJK-UHFFFAOYSA-N 0.000 description 1
- 0 C[C@]1(CC2(CC3(C)C)OCCO2)O[C@]13C=CC(C)=C* Chemical compound C[C@]1(CC2(CC3(C)C)OCCO2)O[C@]13C=CC(C)=C* 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- 241000675108 Citrus tangerina Species 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 241000219112 Cucumis Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 240000006497 Dianthus caryophyllus Species 0.000 description 1
- 235000009355 Dianthus caryophyllus Nutrition 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 235000011511 Diospyros Nutrition 0.000 description 1
- 241000723267 Diospyros Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 229930191978 Gibberellin Natural products 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
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 241000234435 Lilium Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 244000070406 Malus silvestris Species 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- 235000004348 Perilla frutescens Nutrition 0.000 description 1
- 235000006089 Phaseolus angularis Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000233805 Phoenix Species 0.000 description 1
- 240000005809 Prunus persica Species 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 206010040844 Skin exfoliation Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000009337 Spinacia oleracea Nutrition 0.000 description 1
- 244000300264 Spinacia oleracea Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241000722921 Tulipa gesneriana Species 0.000 description 1
- 240000007098 Vigna angularis Species 0.000 description 1
- 235000010711 Vigna angularis Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000002363 auxin Substances 0.000 description 1
- 235000021015 bananas Nutrition 0.000 description 1
- 150000001646 brassinolides Chemical class 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexane-carboxaldehyde Natural products O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000004062 cytokinin Substances 0.000 description 1
- UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 238000000280 densification Methods 0.000 description 1
- 230000035618 desquamation Effects 0.000 description 1
- 238000005906 dihydroxylation reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 230000005059 dormancy Effects 0.000 description 1
- 230000000003 effect on germination Effects 0.000 description 1
- 230000000459 effect on growth Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000004720 fertilization Effects 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 230000004345 fruit ripening Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 1
- 239000003448 gibberellin Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 229930195732 phytohormone Natural products 0.000 description 1
- 230000009596 postnatal growth Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-membered rings
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/22—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom rings with more than six members
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (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)
Abstract
Description
Claims (9)
- 제1항에 있어서, R1이 프로필기 또는 이소프로필기이고, R2및 R3은 함께 에틸렌기를 형성하는 식물성장조절제.
- 제1항에 있어서, 식물성장촉진제인 식물성장조절제.
- 제1항에 있어서, 발아성장촉진제인 식물성장조절제.
- 제1항에 있어서, 증산작용 및 시들음 억제제인 식물성장조절제.
- 제1항에 있어서, 내한성증진제인 식물성장조절제.
- 제1항에 있어서, 과실, 뿌리, 줄기 또는 구근의 성장, 굵기 또는 성장촉진제인 식물성장조절제.
- 제8항에 있어서, R1′가 프로필기 또는 이소프로필기인 에폭시 시클로핵산 유도체.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019997004942A KR100245550B1 (ko) | 1995-09-13 | 1999-05-31 | 에폭시 시클로헥산 유도체와 브라시노스테로이드를 포함하는 식물성장조절제 |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6244937A JPH0881310A (ja) | 1994-09-14 | 1994-09-14 | 植物生長調節剤 |
JP94-244863 | 1994-09-14 | ||
JP94-244937 | 1994-09-14 | ||
JP6244863A JPH0881453A (ja) | 1994-09-14 | 1994-09-14 | エポキシシクロヘキサン誘導体及び植物生長調節剤 |
PCT/JP1995/001816 WO1996008481A1 (fr) | 1994-09-14 | 1995-09-13 | Derive d'epoxycyclohexane et regulateur de croissance vegetale |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019997004942A Division KR100245550B1 (ko) | 1995-09-13 | 1999-05-31 | 에폭시 시클로헥산 유도체와 브라시노스테로이드를 포함하는 식물성장조절제 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR970706268A KR970706268A (ko) | 1997-11-03 |
KR100232484B1 true KR100232484B1 (ko) | 1999-12-01 |
Family
ID=26536940
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019970701685A KR100232484B1 (ko) | 1994-09-14 | 1995-09-13 | 에폭시 시클로헥산 유도체 및 식물성장조절제 |
Country Status (7)
Country | Link |
---|---|
US (2) | US5801123A (ko) |
KR (1) | KR100232484B1 (ko) |
CN (1) | CN1174552A (ko) |
AU (1) | AU3484595A (ko) |
CA (1) | CA2199959A1 (ko) |
RU (1) | RU2126396C1 (ko) |
WO (1) | WO1996008481A1 (ko) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4407464A1 (de) * | 1994-03-07 | 1995-09-28 | Basf Ag | Verfahren zur Herstellung von (1R,4S)-4-Hydroxy-1,2,2-trimethyl-cyclopentyl-methylketon sowie Derivaten und Stereoisomeren dieser Verbindung |
JPH09208407A (ja) * | 1996-02-08 | 1997-08-12 | Sagami Chem Res Center | 植物成長促進剤 |
KR100684939B1 (ko) | 1998-12-18 | 2007-02-22 | 솔베이(소시에떼아노님) | 최소한 하나의 하이드로플루오로알칸과 플루오르화 수소를함유하는 혼합물의 분리방법, 하이드로플루오로알칸의제조방법과 공비조성물 |
US6492174B1 (en) | 2000-06-19 | 2002-12-10 | Institute Of Paper Science & Technology | Methods of initiating embryogenic cultures in plants |
GB0111186D0 (en) * | 2001-05-08 | 2001-06-27 | Smithkline Beecham Plc | Novel compounds |
US7135435B2 (en) * | 2002-12-27 | 2006-11-14 | Sepro Corporation | Plant growth regulation compositions and methods using gibberellin biosynthesis inhibitor combinations |
JP2006028046A (ja) * | 2004-07-13 | 2006-02-02 | Hokkaido Univ | 植物の抽だい誘導抑制及び/又は花芽分化抑制剤 |
EP2098510A1 (en) * | 2008-03-03 | 2009-09-09 | GMI - Gregor-Mendel-Institut für Molekulare Pflanzenbiologie GmbH | Inhibitors for brassinosteroid signalling |
JP2014507130A (ja) | 2010-12-21 | 2014-03-27 | バイエル クロップサイエンス エルピー | バチルスのサンドペーパー突然変異体、及び植物の成長増進、植物の健康促進、並びに植物の病害及び害虫の防除に対するその使用法 |
BR112014005654A2 (pt) | 2011-09-12 | 2017-03-28 | Bayer Cropscience Lp | métodos para melhorar a saúde e promover o crescimento de uma planta e/ou de melhorar o amadurecimento da fruta |
GB2555866B (en) * | 2016-11-15 | 2021-10-27 | Rotam Agrochem Int Co Ltd | A novel crystalline form of epocholeone, a process for its preparation and use the same |
CN116636533B (zh) * | 2023-07-27 | 2023-10-20 | 海南大学三亚南繁研究院 | 一种提高橡胶树苗抗寒性的方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5254694A (en) * | 1989-08-18 | 1993-10-19 | Sagami Chemical Research Center | Optically active epoxycyclohexane derivative and epoxycyclohexanone derivative, and process for the preparation thereof |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2564576B2 (ja) * | 1987-11-10 | 1996-12-18 | タマ生化学株式会社 | ブラシノステロイド誘導体およびそれを用いる植物生育調節剤 |
-
1995
- 1995-09-13 RU RU97105767A patent/RU2126396C1/ru active
- 1995-09-13 US US08/809,051 patent/US5801123A/en not_active Expired - Fee Related
- 1995-09-13 CA CA002199959A patent/CA2199959A1/en not_active Abandoned
- 1995-09-13 KR KR1019970701685A patent/KR100232484B1/ko not_active IP Right Cessation
- 1995-09-13 CN CN95196087A patent/CN1174552A/zh active Pending
- 1995-09-13 WO PCT/JP1995/001816 patent/WO1996008481A1/ja active IP Right Grant
- 1995-09-13 AU AU34845/95A patent/AU3484595A/en not_active Abandoned
-
1998
- 1998-04-24 US US09/066,805 patent/US5965488A/en not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5254694A (en) * | 1989-08-18 | 1993-10-19 | Sagami Chemical Research Center | Optically active epoxycyclohexane derivative and epoxycyclohexanone derivative, and process for the preparation thereof |
Also Published As
Publication number | Publication date |
---|---|
RU2126396C1 (ru) | 1999-02-20 |
WO1996008481A1 (fr) | 1996-03-21 |
KR970706268A (ko) | 1997-11-03 |
US5801123A (en) | 1998-09-01 |
CN1174552A (zh) | 1998-02-25 |
AU3484595A (en) | 1996-03-29 |
US5965488A (en) | 1999-10-12 |
CA2199959A1 (en) | 1996-03-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5201931A (en) | Abscisic acid-related plant growth regulators - germination promoters | |
RU2145165C1 (ru) | Стимулятор роста растений | |
JP3529095B2 (ja) | 植物成長促進剤 | |
JP5323539B2 (ja) | 農作物の収穫部位の収量向上剤 | |
KR840001772B1 (ko) | 1-하이드록시에틸-아졸 유도체의 제조방법 | |
JPH11255607A (ja) | 植物成長調整剤 | |
KR100232484B1 (ko) | 에폭시 시클로헥산 유도체 및 식물성장조절제 | |
EP0232755B1 (en) | Plant growth regulating composition | |
RU2114116C1 (ru) | Брассиностероидные производные и регулирующее рост растений средство | |
JPS5811422B2 (ja) | 1−アミノ−シクロプロパン−カルボン酸化合物の製造方法 | |
US6100219A (en) | Plant growth accelerator | |
JPS5890559A (ja) | アゾリル−アルケノン類及び−オ−ル類 | |
JPS62132804A (ja) | 植物生長調節剤 | |
JPS58134079A (ja) | トリアゾ−ル又はイミダゾ−ル化合物、それらの製造法及びそれらを活性成分とする殺カビ又は植物生長調節剤 | |
KR100245550B1 (ko) | 에폭시 시클로헥산 유도체와 브라시노스테로이드를 포함하는 식물성장조절제 | |
JPS5846093A (ja) | 1−アミノ−シクロプロパンカルボン酸金属錯化合物、その製造法及び植物成長調節剤としての使用 | |
EP0206028B1 (en) | Plant growth promotion | |
JP6706949B2 (ja) | 不定根発生誘導剤及び根系発達促進剤 | |
JPH0881310A (ja) | 植物生長調節剤 | |
CS201518B2 (en) | Means for regulation of the plants growth | |
CS201519B2 (en) | Means for regulation of the growth of plants and method of making the active component | |
JPS6377801A (ja) | 植物生長調節剤 | |
JPH0881453A (ja) | エポキシシクロヘキサン誘導体及び植物生長調節剤 | |
JPH0859408A (ja) | ブラシノステロイド含有組成物およびその水分散体 | |
US4959093A (en) | (22R,23R,24S)-22,23-epoxy-2α3α-isopropylidenedioxy-B-homo-7-oxa-5α-stigmastan-6-one and plant growth regulating method containing the same |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
PA0105 | International application |
Patent event date: 19970314 Patent event code: PA01051R01D Comment text: International Patent Application |
|
PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19970314 Comment text: Request for Examination of Application |
|
PG1501 | Laying open of application | ||
E902 | Notification of reason for refusal | ||
PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19990331 Patent event code: PE09021S01D |
|
A107 | Divisional application of patent | ||
PA0104 | Divisional application for international application |
Comment text: Divisional Application for International Patent Patent event code: PA01041R01D Patent event date: 19990531 |
|
E701 | Decision to grant or registration of patent right | ||
PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19990623 |
|
GRNT | Written decision to grant | ||
PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 19990906 Patent event code: PR07011E01D |
|
PR1002 | Payment of registration fee |
Payment date: 19990907 End annual number: 3 Start annual number: 1 |
|
PG1601 | Publication of registration | ||
LAPS | Lapse due to unpaid annual fee | ||
PC1903 | Unpaid annual fee |
Termination category: Default of registration fee Termination date: 20030610 |