HU180206B - Compositions controlling growth of plants,containing triasolyl-alkohols as active agents,and process for producing gamma-asolyl-alkoholos - Google Patents

Compositions controlling growth of plants,containing triasolyl-alkohols as active agents,and process for producing gamma-asolyl-alkoholos Download PDF

Info

Publication number: HU180206B
Authority: HU; Hungary
Prior art keywords: alkyl; phenyl; butyl; tert; formula
Prior art date: 1977-08-27

Application number

HU78BA3694A

Other languages

German (de)

English (en)

Hungarian (hu)

Inventor

Costin Rentzea

Johann Jung

Hubert Sauter

Gerd Heilen

Bernd Zeeh

Original Assignee

Basf 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.)

1977-08-27

Filing date

1978-08-25

Publication date

1983-02-28

1977-08-27 Priority claimed from DE19772738725 external-priority patent/DE2738725A1/de

1978-08-25 Application filed by Basf Ag filed Critical Basf Ag

1983-02-28 Publication of HU180206B publication Critical patent/HU180206B/hu

Links

238000000034 method Methods 0.000 title claims description 6
239000000203 mixture Substances 0.000 title description 6
230000008635 plant growth Effects 0.000 title description 4
239000013543 active substance Substances 0.000 title description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
125000002541 furyl group Chemical group 0.000 claims abstract description 9
125000001624 naphthyl group Chemical group 0.000 claims abstract description 8
125000001544 thienyl group Chemical group 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000002883 imidazolyl group Chemical group 0.000 claims abstract description 3
239000007788 liquid Substances 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
239000007787 solid Substances 0.000 claims abstract description 3
-1 triazolyl alcohol Chemical compound 0.000 claims description 62
239000004480 active ingredient Substances 0.000 claims description 14
239000003208 petroleum Substances 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
150000002576 ketones Chemical class 0.000 claims description 5
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 4
239000005648 plant growth regulator Substances 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
239000003995 emulsifying agent Substances 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 2
125000000129 anionic group Chemical group 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
239000002270 dispersing agent Substances 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
239000000654 additive Substances 0.000 claims 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
239000004094 surface-active agent Substances 0.000 claims 1
239000000080 wetting agent Substances 0.000 claims 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
125000003302 alkenyloxy group Chemical group 0.000 abstract 1
125000004429 atom Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
239000003795 chemical substances by application Substances 0.000 description 17
241000196324 Embryophyta Species 0.000 description 13
239000000243 solution Substances 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000006185 dispersion Substances 0.000 description 9
230000000694 effects Effects 0.000 description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
150000001875 compounds Chemical class 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
101100310222 Caenorhabditis briggsae she-1 gene Proteins 0.000 description 5
101100356682 Caenorhabditis elegans rho-1 gene Proteins 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000003630 growth substance Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000005995 Aluminium silicate Substances 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000004359 castor oil Substances 0.000 description 3
235000019438 castor oil Nutrition 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 3
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
230000012010 growth Effects 0.000 description 3
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 3
239000011541 reaction mixture Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 2
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
KJGDQSUREDUWIS-UHFFFAOYSA-N CC(C)(C)C(=O)CC(N1C=NC=N1)C1=CC=C(Cl)C=C1 Chemical compound CC(C)(C)C(=O)CC(N1C=NC=N1)C1=CC=C(Cl)C=C1 KJGDQSUREDUWIS-UHFFFAOYSA-N 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229920001807 Urea-formaldehyde Polymers 0.000 description 2
150000003851 azoles Chemical class 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
230000001276 controlling effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000003306 harvesting Methods 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
239000012535 impurity Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
229920005610 lignin Polymers 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
DYGBNAYFDZEYBA-UHFFFAOYSA-N n-(cyclopropylmethyl)-2-[4-(4-methoxybenzoyl)piperidin-1-yl]-n-[(4-oxo-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-2-yl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(CC(=O)N(CC2CC2)CC=2NC(=O)C=3COCCC=3N=2)CC1 DYGBNAYFDZEYBA-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
229940044654 phenolsulfonic acid Drugs 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
QCBPFELXDMTTOL-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-1-(1,2,4-triazol-1-yl)pentan-3-ol Chemical compound C1=NC=NN1C(CC(O)C(C)(C)C)C1=CC=C(Cl)C=C1 QCBPFELXDMTTOL-UHFFFAOYSA-N 0.000 description 1
125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
235000007319 Avena orientalis Nutrition 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
240000002791 Brassica napus Species 0.000 description 1
235000004977 Brassica sinapistrum Nutrition 0.000 description 1
101100334117 Caenorhabditis elegans fah-1 gene Proteins 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
240000006890 Erythroxylum coca Species 0.000 description 1
244000299507 Gossypium hirsutum Species 0.000 description 1
206010053759 Growth retardation Diseases 0.000 description 1
244000020551 Helianthus annuus Species 0.000 description 1
235000003222 Helianthus annuus Nutrition 0.000 description 1
235000005206 Hibiscus Nutrition 0.000 description 1
235000007185 Hibiscus lunariifolius Nutrition 0.000 description 1
244000284380 Hibiscus rosa sinensis Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
241000785681 Sander vitreus Species 0.000 description 1
241000209056 Secale Species 0.000 description 1
235000007238 Secale cereale Nutrition 0.000 description 1
240000003768 Solanum lycopersicum Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
235000009754 Vitis X bourquina Nutrition 0.000 description 1
235000012333 Vitis X labruscana Nutrition 0.000 description 1
240000006365 Vitis vinifera Species 0.000 description 1
235000014787 Vitis vinifera 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
239000002253 acid Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
125000003943 azolyl group Chemical group 0.000 description 1
KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
PJYGPNGTUCHYIC-UHFFFAOYSA-N bis(1h-pyrazol-5-yl)methanone Chemical class C1=CNN=C1C(=O)C=1C=CNN=1 PJYGPNGTUCHYIC-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000003245 coal Substances 0.000 description 1
235000008957 cocaer Nutrition 0.000 description 1
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
229940126086 compound 21 Drugs 0.000 description 1
229940125833 compound 23 Drugs 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
244000038559 crop plants Species 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
RHKZVMUBMXGOLL-UHFFFAOYSA-N cyclopentolate hydrochloride Chemical compound Cl.C1CCCC1(O)C(C(=O)OCCN(C)C)C1=CC=CC=C1 RHKZVMUBMXGOLL-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
230000035784 germination Effects 0.000 description 1
239000008187 granular material Substances 0.000 description 1
231100000001 growth retardation Toxicity 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
239000003415 peat Substances 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
SNWQKAWITMVCQW-UHFFFAOYSA-N phthalylsulfacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1NC(=O)C1=CC=CC=C1C(O)=O SNWQKAWITMVCQW-UHFFFAOYSA-N 0.000 description 1
PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
230000008121 plant development Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
230000005070 ripening Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Cultivation Of Plants (AREA)

HU78BA3694A 1977-08-27 1978-08-25 Compositions controlling growth of plants,containing triasolyl-alkohols as active agents,and process for producing gamma-asolyl-alkoholos HU180206B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772738725 DE2738725A1 (de)	1977-08-27	1977-08-27	Azolylalkohole

Publications (1)

Publication Number	Publication Date
HU180206B true HU180206B (en)	1983-02-28

Family

ID=6017478

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU78BA3694A HU180206B (en)	1977-08-27	1978-08-25	Compositions controlling growth of plants,containing triasolyl-alkohols as active agents,and process for producing gamma-asolyl-alkoholos

Country Status (10)

Country	Link
BR (1)	BR7805534A (cs)
CS (1)	CS199742B2 (cs)
DD (1)	DD136793A5 (cs)
DE (1)	DE2860117D1 (cs)
DK (1)	DK157363C (cs)
FI (1)	FI782595A7 (cs)
HU (1)	HU180206B (cs)
IL (1)	IL55340A (cs)
PL (1)	PL107709B1 (cs)
SU (1)	SU791200A3 (cs)

1978
- 1978-08-11 IL IL55340A patent/IL55340A/xx unknown
- 1978-08-21 DD DD78207393A patent/DD136793A5/xx not_active IP Right Cessation
- 1978-08-22 CS CS785484A patent/CS199742B2/cs unknown
- 1978-08-23 DE DE7878100725T patent/DE2860117D1/de not_active Expired
- 1978-08-23 SU SU782652272A patent/SU791200A3/ru active
- 1978-08-24 FI FI782595A patent/FI782595A7/fi unknown
- 1978-08-25 HU HU78BA3694A patent/HU180206B/hu not_active IP Right Cessation
- 1978-08-25 PL PL1978209219A patent/PL107709B1/xx unknown
- 1978-08-25 DK DK375478A patent/DK157363C/da not_active IP Right Cessation
- 1978-08-25 BR BR7805534A patent/BR7805534A/pt unknown

Also Published As

Publication number	Publication date
PL107709B1 (pl)	1980-02-29
PL209219A1 (pl)	1979-06-04
BR7805534A (pt)	1979-05-08
CS199742B2 (en)	1980-07-31
DK157363B (da)	1989-12-27
DD136793A5 (de)	1979-08-01
DE2860117D1 (en)	1980-11-27
IL55340A (en)	1982-01-31
IL55340A0 (en)	1978-10-31
DK157363C (da)	1990-05-21
SU791200A3 (ru)	1980-12-23
DK375478A (da)	1979-02-28
FI782595A7 (fi)	1979-02-28

Legal Events

Date	Code	Title	Description
1990-06-28	HU90	Patent valid on 900628
1992-08-28	HMM4	Cancellation of final prot. due to non-payment of fee

Publication	Publication Date	Title
EP0000940B1 (de)	1980-08-06	Gamma-Azolylalkohole, und ihre Verwendung zur Regulierung des Pflanzenwachstums
US4177350A (en)	1979-12-04	Imidazole ethyl oxyalkoxy derivatives and thio analogues thereof
IL45133A (en)	1977-08-31	1-phenoxy-1-imidazolyl-alkanol derivatives and their salts process for their preparation and their use as fungicide
HK60683A (en)	1983-12-02	1-(2-aryl-2-r-ethyl)-1h-1,2,4-triazoles
CA1151181A (en)	1983-08-02	.alpha.-AZOLYL-GLYCOL DERIVATIVES, THEIR PREPARATION, FUNGICIDAL AND PLANT GROWTH-REGULATING AGENTS CONTAINING THESE COMPOUNDS, PROCESSES FOR CONTROLLING FUNGI AND REGULATING PLANT GROWTH, AND USE OF THE COMPOUNDS AS FUNGICIDES AND PLANT GROWTH REGULATORS
DE2652313A1 (de)	1978-05-18	Triazolderivate
DE2350123A1 (de)	1975-04-24	1-propyl-imidazolyl-derivate und deren salze, verfahren zu ihrer herstellung und ihre verwendung als fungizide
CS236885B2 (en)	1985-05-15	Fungicide agent and processing of active components
GB1601877A (en)	1981-11-04	Azolyl-acetophenone-oxime ethers and their use as fungicides
CA1189857A (en)	1985-07-02	Antimicrobial triazole derivatives
CS221276B2 (en)	1983-04-29	Fungicide means
DD151039A5 (de)	1981-09-30	Fungizide mittel
CH635481A5 (de)	1983-04-15	Fungizides mittel.
US4331675A (en)	1982-05-25	Combating fungi with triazolyl-alkenes
DD212408A5 (de)	1984-08-15	Pflanzenschutzmittel
DE2935452A1 (de)	1981-03-19	N-phenylpropylsubstituierte azole, verfahren zu ihrer herstellung und diese enthaltende fungizide
EP0010287A1 (de)	1980-04-30	Gamma-Azolylverbindungen, wachstumsregulierende Mittel, Verfahren zur Herstellung dieser und Verfahren zur Regulierung des Pflanzenwachstums
CH633276A5 (de)	1982-11-30	Fungizides und bakterizides mittel sowie verfahren zur herstellung neuer 1-azolyl-4-hydroxy-butan-derivate.
HU176920B (hu)	1981-06-28	Fungicidnye kompozicii soderzhahhie beta-triazolil-ketony i soli,i sposob poluchenija beta-triazolil-ketonov
DE2556319A1 (de)	1977-06-23	Substituierte triazol-aether
HU180206B (en)	1983-02-28	Compositions controlling growth of plants,containing triasolyl-alkohols as active agents,and process for producing gamma-asolyl-alkoholos
DE2944223A1 (de)	1981-05-27	Fungizide entriazole, ihre herstellung und verwendung
DE2828222A1 (de)	1980-01-10	Gegenmittel zum schutz von kulturpflanzen vor schaedigungen durch herbizide
US4515616A (en)	1985-05-07	Triazolyl ketone-oximes and triazolyl dioximes, their preparation and their use as plant growth regulators
DE2821829A1 (de)	1979-11-22	Mittel zur regulierung des pflanzenwachstums