DD261951A5 - Pflanzenwachstumsregulierende mittel - Google Patents

Pflanzenwachstumsregulierende mittel Download PDF

Info

Publication number: DD261951A5
Authority: DD; German Democratic Republic
Prior art keywords: oil; compounds; cooch; growth; coo
Prior art date: 1986-08-27

Application number

DD87306324A

Other languages

German (de)

English (en)

Inventor

Roland Schmierer

Hilmar Mildenberger

Helmut Buerstell

Original Assignee

��@��k��

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.)

1986-08-27

Filing date

1987-08-25

Publication date

1988-11-16

1987-08-25 Application filed by ��@��k�� filed Critical ��@��k��

1988-11-16 Publication of DD261951A5 publication Critical patent/DD261951A5/de

Links

150000001875 compounds Chemical class 0.000 claims abstract description 32
150000003839 salts Chemical class 0.000 claims abstract description 16
229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
229910052794 bromium Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
230000008635 plant growth Effects 0.000 claims abstract description 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 3
150000002431 hydrogen Chemical class 0.000 claims abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
239000003795 chemical substances by application Substances 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
238000005956 quaternization reaction Methods 0.000 claims description 6
239000003630 growth substance Substances 0.000 claims description 4
230000001105 regulatory effect Effects 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims 1
230000026267 regulation of growth Effects 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 4
125000006698 (C1-C3) dialkylamino group Chemical group 0.000 abstract 1
239000000460 chlorine Substances 0.000 description 137
239000003921 oil Substances 0.000 description 29
239000004480 active ingredient Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
239000002253 acid Substances 0.000 description 11
-1 2,2,3,3-tetrafluoropropyl Chemical group 0.000 description 9
241000196324 Embryophyta Species 0.000 description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
238000009472 formulation Methods 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
230000012010 growth Effects 0.000 description 7
230000009036 growth inhibition Effects 0.000 description 7
239000000126 substance Substances 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000013543 active substance Substances 0.000 description 6
125000000896 monocarboxylic acid group Chemical group 0.000 description 6
230000000694 effects Effects 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
229920000151 polyglycol Polymers 0.000 description 5
239000010695 polyglycol Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
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 4
150000001768 cations Chemical class 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
238000000227 grinding Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
239000005648 plant growth regulator Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000002904 solvent Substances 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
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CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
240000007594 Oryza sativa Species 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
150000002460 imidazoles Chemical class 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
239000003960 organic solvent Substances 0.000 description 3
150000004841 phenylimidazoles Chemical class 0.000 description 3
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 3
239000011347 resin Substances 0.000 description 3
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239000007787 solid Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
239000008096 xylene Substances 0.000 description 3
UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 2
CMJUNAQINNWKAU-KTKRTIGZSA-N 2-[[(z)-2-oxononadec-10-enyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)CNCCS(O)(=O)=O CMJUNAQINNWKAU-KTKRTIGZSA-N 0.000 description 2
KWIPUXXIFQQMKN-UHFFFAOYSA-N 2-azaniumyl-3-(4-cyanophenyl)propanoate Chemical compound OC(=O)C(N)CC1=CC=C(C#N)C=C1 KWIPUXXIFQQMKN-UHFFFAOYSA-N 0.000 description 2
AREQLMOKABEPTN-UHFFFAOYSA-N 3-(3-bromo-2,6-diethylphenyl)imidazole-4-carboxylic acid Chemical compound CCC1=CC=C(Br)C(CC)=C1N1C(C(O)=O)=CN=C1 AREQLMOKABEPTN-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare 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
235000007164 Oryza sativa Nutrition 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
238000000297 Sandmeyer reaction Methods 0.000 description 2
235000007238 Secale cereale Nutrition 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
241000209140 Triticum Species 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
229940090948 ammonium benzoate Drugs 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
PILZBMKKCUWTHM-UHFFFAOYSA-N ethyl 3-(3-bromo-2,6-diethylphenyl)imidazole-4-carboxylate Chemical compound CCOC(=O)C1=CN=CN1C1=C(CC)C=CC(Br)=C1CC PILZBMKKCUWTHM-UHFFFAOYSA-N 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
239000003337 fertilizer Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
125000002883 imidazolyl group Chemical group 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000002892 organic cations Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
230000000885 phytotoxic effect Effects 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
235000009566 rice Nutrition 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 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
230000009105 vegetative growth Effects 0.000 description 2
238000009736 wetting Methods 0.000 description 2
DARPYRSDRJYGIF-PTNGSMBKSA-N (Z)-3-ethoxy-2-naphthalen-2-ylsulfonylprop-2-enenitrile Chemical compound C1=CC=CC2=CC(S(=O)(=O)C(\C#N)=C/OCC)=CC=C21 DARPYRSDRJYGIF-PTNGSMBKSA-N 0.000 description 1
MARCAKLHFUYDJE-UHFFFAOYSA-N 1,2-xylene;hydrate Chemical compound O.CC1=CC=CC=C1C MARCAKLHFUYDJE-UHFFFAOYSA-N 0.000 description 1
SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical class C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 1
SVOAUHHKPGKPQK-UHFFFAOYSA-N 2-chloro-9-hydroxyfluorene-9-carboxylic acid Chemical compound C1=C(Cl)C=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 SVOAUHHKPGKPQK-UHFFFAOYSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 1
FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
229930192334 Auxin Natural products 0.000 description 1
240000002791 Brassica napus Species 0.000 description 1
235000006008 Brassica napus var napus Nutrition 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
102000004127 Cytokines Human genes 0.000 description 1
108090000695 Cytokines Proteins 0.000 description 1
206010013883 Dwarfism Diseases 0.000 description 1
239000005976 Ethephon Substances 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
244000020551 Helianthus annuus Species 0.000 description 1
235000003222 Helianthus annuus Nutrition 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 1
OKIBNKKYNPBDRS-UHFFFAOYSA-N Mefluidide Chemical compound CC(=O)NC1=CC(NS(=O)(=O)C(F)(F)F)=C(C)C=C1C OKIBNKKYNPBDRS-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
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RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 description 1
240000000111 Saccharum officinarum Species 0.000 description 1
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229920002125 Sokalan® Polymers 0.000 description 1
244000062793 Sorghum vulgare Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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239000000853 adhesive Substances 0.000 description 1
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238000007112 amidation reaction Methods 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
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HUTDUHSNJYTCAR-UHFFFAOYSA-N ancymidol Chemical compound C1=CC(OC)=CC=C1C(O)(C=1C=NC=NC=1)C1CC1 HUTDUHSNJYTCAR-UHFFFAOYSA-N 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
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239000002363 auxin Substances 0.000 description 1
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239000000440 bentonite Substances 0.000 description 1
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SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-O butylazanium Chemical compound CCCC[NH3+] HQABUPZFAYXKJW-UHFFFAOYSA-O 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
JUZXDNPBRPUIOR-UHFFFAOYSA-N chlormequat Chemical compound C[N+](C)(C)CCCl JUZXDNPBRPUIOR-UHFFFAOYSA-N 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
PAFZNILMFXTMIY-UHFFFAOYSA-O cyclohexylammonium Chemical compound [NH3+]C1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-O 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010410 dusting Methods 0.000 description 1
244000013123 dwarf bean Species 0.000 description 1
235000005489 dwarf bean Nutrition 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
PNNGMIOQIDGQDS-UHFFFAOYSA-N ethyl 3-(3-amino-2,6-diethylphenyl)imidazole-4-carboxylate Chemical compound CCOC(=O)C1=CN=CN1C1=C(CC)C=CC(N)=C1CC PNNGMIOQIDGQDS-UHFFFAOYSA-N 0.000 description 1
SEQOXRAWPSAZDO-UHFFFAOYSA-N ethyl 3-(3-chloro-6-ethyl-2-methylphenyl)imidazole-4-carboxylate Chemical compound CCOC(=O)C1=CN=CN1C1=C(CC)C=CC(Cl)=C1C SEQOXRAWPSAZDO-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
208000037824 growth disorder Diseases 0.000 description 1
239000003966 growth inhibitor Substances 0.000 description 1
ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
GLUUGHFHXGJENI-UHFFFAOYSA-O hydron piperazine Chemical compound [H+].C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-O 0.000 description 1
RBLWMQWAHONKNC-UHFFFAOYSA-N hydroxyazanium Chemical compound O[NH3+] RBLWMQWAHONKNC-UHFFFAOYSA-N 0.000 description 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
VHOVSQVSAAQANU-UHFFFAOYSA-M mepiquat chloride Chemical compound [Cl-].C[N+]1(C)CCCCC1 VHOVSQVSAAQANU-UHFFFAOYSA-M 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229920000847 nonoxynol Polymers 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
229920002113 octoxynol Polymers 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical class [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
239000003375 plant hormone Substances 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920001522 polyglycol ester Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
230000036435 stunted growth Effects 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical class [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

DD87306324A 1986-08-27 1987-08-25 Pflanzenwachstumsregulierende mittel DD261951A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19863629064 DE3629064A1 (de)	1986-08-27	1986-08-27	2,3,6-substituierte phenylimidazolderivate, verfahren zu ihrer herstellung und ihre verwendung als wachstumgsregulatoren

Publications (1)

Publication Number	Publication Date
DD261951A5 true DD261951A5 (de)	1988-11-16

Family

ID=6308255

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87306324A DD261951A5 (de)	1986-08-27	1987-08-25	Pflanzenwachstumsregulierende mittel

Country Status (11)

Country	Link
US (1)	US4808213A (fr)
EP (1)	EP0264577A1 (fr)
JP (1)	JPS6368570A (fr)
CN (1)	CN87105807A (fr)
AU (1)	AU7744087A (fr)
DD (1)	DD261951A5 (fr)
DE (1)	DE3629064A1 (fr)
DK (1)	DK445787A (fr)
HU (1)	HUT44903A (fr)
IL (1)	IL83645A0 (fr)
ZA (1)	ZA876351B (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1217900B (it) *	1988-06-23	1990-03-30	Mini Ricerca Scient Tecnolog	Composti eterociclici azotati ad azione antifungina
DE3902439A1 (de) *	1989-01-27	1990-08-02	Basf Ag	Pflanzenschuetzende mittel auf basis von 1-aryl- bzw. 1-hetarylimidazolcarbonsaeureestern
US5211737A (en) *	1989-01-31	1993-05-18	Basf Aktiengesellschaft	4-arryl-2-haloimidazole-5-carboxylic esters, the preparation and use thereof
DE3902772A1 (de) *	1989-01-31	1990-08-02	Basf Ag	4-aryl-2-halogenimidazol-5-carbonsaeureester, ihre herstellung und verwendung
CA2032289A1 (fr) *	1989-12-29	1991-06-30	Joseph A. Finkelstein	5-(alkyl)carboxamideimidazoles substitues
US5627134A (en) *	1995-06-05	1997-05-06	Basf Corporation	Plant growth regulating compositions and methods
BR9813092A (pt) *	1997-10-20	2000-08-22	Basf Ag	Formulação, uso da mesma, e, processo para regular o crescimento das plantas
US8937184B2 (en) *	2005-02-16	2015-01-20	Abbvie B.V.	1H-imidazole derivatives as cannabinoid CB2 receptor modulators
WO2011010695A1 (fr) *	2009-07-24	2011-01-27	国立大学法人静岡大学	Procédé permettant d'augmenter le rendement des cultures vivrières de base
PE20141468A1 (es)	2010-12-21	2014-11-05	Bayer Cropscience Lp	Mutantes tipo papel de lija de bacillus y metodos de uso de los mismo para mejorar el crecimiento vegetal, promover la salud de plantas y controlar enfermedades y plagas
US8809328B2 (en)	2011-04-27	2014-08-19	National University Corporation Shizuoka University	Imidazole derivative
MX2014002890A (es)	2011-09-12	2015-01-19	Bayer Cropscience Lp	Metodo para mejorar la salud y/o promover el crecimiento de una planta y/o mejorar la maduracion de frutos.
EP3960244B8 (fr)	2019-06-06	2025-05-14	Mitsubishi Corporation Life Sciences Limited	Activateur cellulaire de cellule animale

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3217094A1 (de) *	1982-05-07	1983-11-10	Hoechst Ag, 6230 Frankfurt	1-substituierte imidazol-5-carbonsaeurederivate, ihre herstellung sowie ihre verwendung als biozide
DE3444918A1 (de) *	1984-12-08	1986-06-12	Hoechst Ag, 6230 Frankfurt	1-phenyl-imidazol-5-carbonsaeure-derivate, ein verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren

1986
- 1986-08-27 DE DE19863629064 patent/DE3629064A1/de not_active Withdrawn
1987
- 1987-08-25 EP EP87112287A patent/EP0264577A1/fr not_active Withdrawn
- 1987-08-25 US US07/089,476 patent/US4808213A/en not_active Expired - Fee Related
- 1987-08-25 IL IL83645A patent/IL83645A0/xx unknown
- 1987-08-25 DD DD87306324A patent/DD261951A5/de not_active IP Right Cessation
- 1987-08-25 CN CN198787105807A patent/CN87105807A/zh active Pending
- 1987-08-26 DK DK445787A patent/DK445787A/da not_active Application Discontinuation
- 1987-08-26 HU HU873767A patent/HUT44903A/hu unknown
- 1987-08-26 ZA ZA876351A patent/ZA876351B/xx unknown
- 1987-08-26 JP JP62210369A patent/JPS6368570A/ja active Pending
- 1987-08-26 AU AU77440/87A patent/AU7744087A/en not_active Abandoned

Also Published As

Publication number	Publication date
DE3629064A1 (de)	1988-03-03
DK445787D0 (da)	1987-08-26
AU7744087A (en)	1988-03-03
EP0264577A1 (fr)	1988-04-27
DK445787A (da)	1988-02-28
US4808213A (en)	1989-02-28
HUT44903A (en)	1988-05-30
IL83645A0 (en)	1988-01-31
CN87105807A (zh)	1988-04-06
JPS6368570A (ja)	1988-03-28
ZA876351B (en)	1988-03-01

Legal Events

Date	Code	Title	Description
2000-08-03	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE2632581C2 (de)	1982-07-15	Substituierte Nitrodiphenylether, Verfahren zu ihrer Herstellung und diese enthaltende herbizide Mittel
DD261951A5 (de)	1988-11-16	Pflanzenwachstumsregulierende mittel
EP0014684A2 (fr)	1980-08-20	Dérivés substitués en position 2 d'acides phénoxy-5 phénylphosphoniques, procédé pour leur préparation et leur utilisation comme herbicides
EP0137868B1 (fr)	1987-08-12	Dérivés d'acides imidazole-5-carboxyliques substitués en position 1, leur préparation et leur utilisation comme biocides
EP0011693A1 (fr)	1980-06-11	N-hétérocycles N-substitués par trifluorométhane-sulfonylaminophényle, leur préparation, compositions les contenant et leur utilisation pour la régulation de la croissance des plantes
EP0008804B1 (fr)	1983-11-16	Imidazolylvinyléthers, procédé pour leur préparation, leur utilisation en tant que matières actives dans des produits pharmaceutiques et biocides
DE3514116A1 (de)	1986-10-23	Neue cyclohexyl- und cyclohexenylimidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatoren
EP0243615B1 (fr)	1991-03-20	Amides de phényl-1-imidazole-acide carbonique, leur procédé de préparation et leur application comme régulateurs de croissance
EP0167776B1 (fr)	1989-04-05	Agent régulateur de la croissance des plantes
DE2018969A1 (de)	1970-11-05	Selektive Herbizide
EP0170842B1 (fr)	1989-09-13	Dérivés de N-benzylcyclopropanecarboxamide, procédé pour leur preperation et fongicides pour l'agriculture et l'horticulture
EP0075840B1 (fr)	1987-11-11	Phényléthers hétérocycliques, procédé pour leur préparation et herbicides les contenant
DD259124A5 (de)	1988-08-17	Pflanzenwachstumsregulierende mittel
DD259560A5 (de)	1988-08-31	Pflanzenwachstumsregulierende mittel
EP0185961A2 (fr)	1986-07-02	Dérivés d'acide 1-phényl-imidazole-5-carboxylique, procédé pour leur préparation et leur application comme régulateurs de croissance
EP0163236A2 (fr)	1985-12-04	Benzoxazolyl et benzothiazolyl aminoacides, leur préparation et leur utilisation comme agents protecteurs de plantes
DE3210009C2 (fr)	1989-09-14
EP0048997A1 (fr)	1982-04-07	Agents fongicides contenant des composés hétérocycliques et la préparation et l'utilisation de ces agents
DD218828A5 (de)	1985-02-20	Herbizide zusammensetzung
DD262992A5 (de)	1988-12-21	Nematizide und insektizide zusammensetzung
EP0013873A1 (fr)	1980-08-06	Anilides de l'acide N-azolyl acétique, procédé pour leur préparation et leur utilisation comme herbicides
DD218268A5 (de)	1985-02-06	Herbizide zusammensetzung
DD234603A5 (de)	1986-04-09	Antifungische zusammensetzung
DE2832890A1 (de)	1980-02-14	Herbizide mittel
DD239108A5 (de)	1986-09-17	Das pflanzenwachstum regulierende mittel