DD289523A5 - Verfahren zur herstellung von azolderivaten - Google Patents

Verfahren zur herstellung von azolderivaten Download PDF

Info

Publication number: DD289523A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; hydrogen; formula; derivative; type
Prior art date: 1987-06-30

Application number

DD88313525A

Other languages

German (de)

English (en)

Inventor

Satoru Kumazawa

Susumu Shimizu

Hiroyuki Enari

Atsushi Ito

Susumu Ikeda

Nobuo Sato

Toshihide Saishoji

Original Assignee

Kureha Kagaku Kogyo Kabushiki Kaisha,Jp

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.)

1987-06-30

Filing date

1988-03-09

Publication date

1991-05-02

1988-03-09 Application filed by Kureha Kagaku Kogyo Kabushiki Kaisha,Jp filed Critical Kureha Kagaku Kogyo Kabushiki Kaisha,Jp

1991-05-02 Publication of DD289523A5 publication Critical patent/DD289523A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 34
230000008569 process Effects 0.000 title claims abstract description 12
238000002360 preparation method Methods 0.000 title abstract description 37
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 99
239000000203 mixture Substances 0.000 claims abstract description 93
150000007980 azole derivatives Chemical class 0.000 claims abstract description 55
238000006243 chemical reaction Methods 0.000 claims abstract description 26
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 25
150000002924 oxiranes Chemical class 0.000 claims abstract description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 75
239000001257 hydrogen Substances 0.000 claims description 74
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
-1 benzyl halide Chemical class 0.000 claims description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
229910052736 halogen Inorganic materials 0.000 claims description 25
150000002367 halogens Chemical group 0.000 claims description 25
BGTOWKSIORTVQH-HOSYLAQJSA-N cyclopentanone Chemical class O=[13C]1CCCC1 BGTOWKSIORTVQH-HOSYLAQJSA-N 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 20
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical class OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims description 19
239000000543 intermediate Substances 0.000 claims description 18
230000000855 fungicidal effect Effects 0.000 claims description 17
125000005907 alkyl ester group Chemical group 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 13
239000013543 active substance Substances 0.000 claims description 13
230000008635 plant growth Effects 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 12
NFJPEKRRHIYYES-UHFFFAOYSA-N methylidenecyclopentane Chemical class C=C1CCCC1 NFJPEKRRHIYYES-UHFFFAOYSA-N 0.000 claims description 10
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 8
238000006114 decarboxylation reaction Methods 0.000 claims description 8
229910052783 alkali metal Chemical group 0.000 claims description 7
230000001105 regulatory effect Effects 0.000 claims description 7
238000007239 Wittig reaction Methods 0.000 claims description 6
150000001340 alkali metals Chemical group 0.000 claims description 6
238000006735 epoxidation reaction Methods 0.000 claims description 6
FXBPINRBSNMESY-UHFFFAOYSA-N 2-oxocyclopentane-1-carboxylic acid Chemical compound OC(=O)C1CCCC1=O FXBPINRBSNMESY-UHFFFAOYSA-N 0.000 claims description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
230000003301 hydrolyzing effect Effects 0.000 claims description 4
150000001350 alkyl halides Chemical class 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
RHQQHZQUAMFINJ-GKWSUJDHSA-N 1-[(3s,5s,8s,9s,10s,11s,13s,14s,17s)-3,11-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethanone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CC[C@H]21 RHQQHZQUAMFINJ-GKWSUJDHSA-N 0.000 claims 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 4
239000000126 substance Substances 0.000 description 115
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
241000196324 Embryophyta Species 0.000 description 40
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 22
239000012074 organic phase Substances 0.000 description 22
239000012312 sodium hydride Substances 0.000 description 22
229910000104 sodium hydride Inorganic materials 0.000 description 22
201000010099 disease Diseases 0.000 description 21
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 21
230000000694 effects Effects 0.000 description 21
239000000243 solution Substances 0.000 description 21
239000002904 solvent Substances 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 20
238000005406 washing Methods 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
206010061217 Infestation Diseases 0.000 description 16
240000007594 Oryza sativa Species 0.000 description 16
150000002148 esters Chemical class 0.000 description 15
150000003254 radicals Chemical class 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000003085 diluting agent Substances 0.000 description 14
239000005457 ice water Substances 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 13
235000007164 Oryza sativa Nutrition 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
235000009566 rice Nutrition 0.000 description 13
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
241000209140 Triticum Species 0.000 description 11
235000021307 Triticum Nutrition 0.000 description 11
238000011835 investigation Methods 0.000 description 11
150000003839 salts Chemical class 0.000 description 10
238000003756 stirring Methods 0.000 description 10
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
238000001816 cooling Methods 0.000 description 9
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
239000012071 phase Substances 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 8
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical class O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 8
230000012010 growth Effects 0.000 description 8
238000011081 inoculation Methods 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000004563 wettable powder Substances 0.000 description 8
241000233866 Fungi Species 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
239000012298 atmosphere Substances 0.000 description 7
239000002585 base Substances 0.000 description 7
239000001307 helium Substances 0.000 description 7
229910052734 helium Inorganic materials 0.000 description 7
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 7
239000000843 powder Substances 0.000 description 7
238000001228 spectrum Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
238000011282 treatment Methods 0.000 description 7
240000008067 Cucumis sativus Species 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
238000000862 absorption spectrum Methods 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000002609 medium Substances 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
229920001817 Agar Polymers 0.000 description 5
240000005979 Hordeum vulgare Species 0.000 description 5
235000007340 Hordeum vulgare Nutrition 0.000 description 5
244000046052 Phaseolus vulgaris Species 0.000 description 5
235000014443 Pyrus communis Nutrition 0.000 description 5
239000008272 agar Substances 0.000 description 5
125000003710 aryl alkyl group Chemical group 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
125000000753 cycloalkyl group Chemical group 0.000 description 5
210000003298 dental enamel Anatomy 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
239000005648 plant growth regulator Substances 0.000 description 5
241000123650 Botrytis cinerea Species 0.000 description 4
244000068988 Glycine max Species 0.000 description 4
235000010469 Glycine max Nutrition 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
235000009754 Vitis X bourquina Nutrition 0.000 description 4
235000012333 Vitis X labruscana Nutrition 0.000 description 4
240000006365 Vitis vinifera Species 0.000 description 4
235000014787 Vitis vinifera Nutrition 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
230000033228 biological regulation Effects 0.000 description 4
238000013375 chromatographic separation Methods 0.000 description 4
230000001276 controlling effect Effects 0.000 description 4
235000013399 edible fruits Nutrition 0.000 description 4
230000002538 fungal effect Effects 0.000 description 4
239000011521 glass Substances 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
230000000704 physical effect Effects 0.000 description 4
230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
241001450781 Bipolaris oryzae Species 0.000 description 3
241000895502 Blumeria graminis f. sp. tritici Species 0.000 description 3
241000219112 Cucumis Species 0.000 description 3
235000015510 Cucumis melo subsp melo Nutrition 0.000 description 3
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
241000896246 Golovinomyces cichoracearum Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
244000061176 Nicotiana tabacum Species 0.000 description 3
235000002637 Nicotiana tabacum Nutrition 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
241001123569 Puccinia recondita Species 0.000 description 3
235000021536 Sugar beet Nutrition 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
239000004927 clay Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
GZRYBYIBLHMWCD-UHFFFAOYSA-N dimethyl(methylidene)-$l^{4}-sulfane Chemical compound CS(C)=C GZRYBYIBLHMWCD-UHFFFAOYSA-N 0.000 description 3
DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 description 3
235000021186 dishes Nutrition 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
238000005755 formation reaction Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
125000001188 haloalkyl group Chemical group 0.000 description 3
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
150000002460 imidazoles Chemical class 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 3
239000000463 material Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
238000000746 purification Methods 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
125000003107 substituted aryl group Chemical group 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
150000003852 triazoles Chemical class 0.000 description 3
239000008096 xylene Substances 0.000 description 3
125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
AZHWYUGUSFZXJD-UHFFFAOYSA-N 1-(1h-pyrrol-2-yl)cyclopentan-1-ol Chemical class C=1C=CNC=1C1(O)CCCC1 AZHWYUGUSFZXJD-UHFFFAOYSA-N 0.000 description 2
OPVGROQKULZZGE-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-5-methylcyclopentan-1-one Chemical compound O=C1C(C)CCC1CC1=CC=C(Cl)C=C1 OPVGROQKULZZGE-UHFFFAOYSA-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 compound 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
DLPBZANLIRTMKU-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentan-1-one Chemical compound O=C1C(C)(C)CCC1CC1=CC=C(Cl)C=C1 DLPBZANLIRTMKU-UHFFFAOYSA-N 0.000 description 2
235000001674 Agaricus brunnescens Nutrition 0.000 description 2
241000213004 Alternaria solani Species 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
244000241235 Citrullus lanatus Species 0.000 description 2
235000012828 Citrullus lanatus var citroides Nutrition 0.000 description 2
241001133184 Colletotrichum agaves Species 0.000 description 2
241000222235 Colletotrichum orbiculare Species 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
241000223221 Fusarium oxysporum Species 0.000 description 2
241000382773 Fusarium oxysporum f. sp. raphani Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
241000862466 Monilinia laxa Species 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
241001626624 Nakataea sigmoidea Species 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
231100000674 Phytotoxicity Toxicity 0.000 description 2
241000317981 Podosphaera fuliginea Species 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
241000221300 Puccinia Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
235000006140 Raphanus sativus var sativus Nutrition 0.000 description 2
241000221662 Sclerotinia Species 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
240000003768 Solanum lycopersicum Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
241001512566 Valsa mali Species 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000009471 action Effects 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
150000001346 alkyl aryl ethers Chemical class 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
239000000440 bentonite Substances 0.000 description 2
229910000278 bentonite Inorganic materials 0.000 description 2
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
239000012267 brine Substances 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
125000004438 haloalkoxy group Chemical group 0.000 description 2
230000006872 improvement Effects 0.000 description 2
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
229920005610 lignin Polymers 0.000 description 2
239000007788 liquid Substances 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000002265 prevention Effects 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
238000005507 spraying Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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125000000623 heterocyclic group Chemical group 0.000 description 1
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229940071870 hydroiodic acid Drugs 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
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HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
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244000144972 livestock Species 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
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229910052987 metal hydride Inorganic materials 0.000 description 1
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
QGUHMUXBDNKLNM-UHFFFAOYSA-N methyl 1-[(4-chlorophenyl)methyl]-3,3-dimethyl-2-oxocyclopentane-1-carboxylate Chemical compound C=1C=C(Cl)C=CC=1CC1(C(=O)OC)CCC(C)(C)C1=O QGUHMUXBDNKLNM-UHFFFAOYSA-N 0.000 description 1
WICVAJZHKHFIAF-UHFFFAOYSA-N methyl 1-[(4-chlorophenyl)methyl]-3-ethyl-3-methyl-2-oxocyclopentane-1-carboxylate Chemical compound O=C1C(CC)(C)CCC1(C(=O)OC)CC1=CC=C(Cl)C=C1 WICVAJZHKHFIAF-UHFFFAOYSA-N 0.000 description 1
DCLNQHDBQDTZAT-UHFFFAOYSA-N methyl 1-[(4-chlorophenyl)methyl]-3-methyl-2-oxocyclopentane-1-carboxylate Chemical compound C=1C=C(Cl)C=CC=1CC1(C(=O)OC)CCC(C)C1=O DCLNQHDBQDTZAT-UHFFFAOYSA-N 0.000 description 1
LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
XYDYWTJEGDZLTH-UHFFFAOYSA-N methylenetriphenylphosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C)C1=CC=CC=C1 XYDYWTJEGDZLTH-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229950004080 oxiramide Drugs 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
125000002071 phenylalkoxy group Chemical group 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
208000007578 phototoxic dermatitis Diseases 0.000 description 1
231100000018 phototoxicity Toxicity 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
239000003375 plant hormone Substances 0.000 description 1
231100000719 pollutant Toxicity 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-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
238000013138 pruning Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000026267 regulation of growth Effects 0.000 description 1
230000005070 ripening Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000004544 sputter deposition Methods 0.000 description 1
235000021012 strawberries Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
YRYSAWZMIRQUBO-UHFFFAOYSA-N trimethylsulfoxonium Chemical compound C[S+](C)(C)=O YRYSAWZMIRQUBO-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
230000009105 vegetative growth Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD88313525A 1987-06-30 1988-03-09 Verfahren zur herstellung von azolderivaten DD289523A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP16112687		1987-06-30

Publications (1)

Publication Number	Publication Date
DD289523A5 true DD289523A5 (de)	1991-05-02

Family

ID=15729096

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88313525A DD289523A5 (de)	1987-06-30	1988-03-09	Verfahren zur herstellung von azolderivaten

Country Status (6)

Country	Link
DD (1)	DD289523A5 (lt)
GE (1)	GEP19981389B (lt)
LT (1)	LT4014B (lt)
LV (1)	LV10744B (lt)
RU (1)	RU1837767C (lt)
UA (1)	UA18635A (lt)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4863505A (en)	1985-09-12	1989-09-05	Kureha Kagaku Kogyo Kabushiki Kaisha	Novel derivative of azole, and agricultural and horticultural composition containing the same as an active incredient

1988
- 1988-03-09 DD DD88313525A patent/DD289523A5/de not_active IP Right Cessation
- 1988-03-09 UA UA4355807A patent/UA18635A/uk unknown
- 1988-03-09 RU SU884355807A patent/RU1837767C/ru active
1993
- 1993-06-30 LV LVP-93-926A patent/LV10744B/lv unknown
1994
- 1994-01-31 LT LTIP1864A patent/LT4014B/lt not_active IP Right Cessation
- 1994-09-07 GE GEAP19942167A patent/GEP19981389B/en unknown

Also Published As

Publication number	Publication date
LT4014B (en)	1996-08-26
UA18635A (uk)	1997-12-25
LTIP1864A (en)	1995-08-25
LV10744A (lv)	1995-08-20
LV10744B (en)	1995-12-20
RU1837767C (ru)	1993-08-30
GEP19981389B (en)	1998-11-10

Legal Events

Date	Code	Title	Description
1999-09-30	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE3784999T2 (de)	1993-07-01	Azol-derivate verwendbar zur kontrolle von pflanzenkrankheiten und regulierung von pflanzenwachstum.
EP0297345B2 (de)	1993-10-13	Azolylmethyl-cyclopropyl-Derivate
EP0040350B1 (de)	1983-09-21	Neue Azolverbindungen, ihre Herstellung, ihre Verwendung zur Pflanzenbehandlung und Mittel dafür
DE3630840C2 (lt)	1989-02-09
EP0461502B1 (de)	1996-08-28	Azolyl-propanol-Derivate
EP0071568B1 (de)	1987-01-21	Mandelsäure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Mikroorganismen
EP0291797A2 (de)	1988-11-23	Hydroxyalkyl-azolyl-Derivate
EP0298332B1 (de)	1990-11-28	Hydroxyalkyl-azolyl-Derivate
EP0137868A1 (de)	1985-04-24	1-Substituierte Imidazol-5-carbonsäurederivate, ihre Herstellung sowie ihre Verwendung als Biozide
HU206023B (en)	1992-08-28	Compositions with fungicidal and plant growth regulating activity and process for producing new azole derivatives used as active ingredient of the compositions
DE68906551T2 (de)	1993-09-02	Azolsubstituierte cycloalkanol-derivate, verfahren zu deren herstellung und anwendung dieser derivate als fungizide in der landwirtschaft und im gartenbau.
EP0297383B1 (de)	1990-10-10	Hydroxyethyl-azolyl-Derivate
DE3725397A1 (de)	1989-02-09	1,4-disubstituierte 1-azolyl-3,3-dimethylbutan-derivate
EP0180838A2 (de)	1986-05-14	Substituierte Azolylcyclopropyl-azolylmethyl-carbinol-Derivate
EP0291795B1 (de)	1990-12-05	Hydroxyalkyl-triazolyl-Derivate
EP0327913B1 (de)	1994-04-06	Substituierte Azolylmethyloxirane
DE3702301A1 (de)	1987-09-10	2-hydroxyethyl-azol-derivate
DD289523A5 (de)	1991-05-02	Verfahren zur herstellung von azolderivaten
EP0224076B1 (de)	1989-11-08	Azolyletherketone und -alkohole
EP0254797B1 (de)	1990-07-04	2-Hydroxyethyl-azol-Derivate
DE3722133A1 (de)	1989-01-12	Azolyl-tetrahydropyran-derivate
EP0291798B1 (de)	1992-03-18	Hydroxyalkyl-triazolyl-Derivate
EP0296452A1 (de)	1988-12-28	Azolylmethyl-cyclopropyl-carbinol-Derivate
EP0438686A2 (de)	1991-07-31	Triazolylmethyl-cyclopropyl-Derivate
EP0189034B1 (de)	1989-03-01	Azolyl-aroxymethyl-dimethylpentinole