DD239108A5 - Das pflanzenwachstum regulierende mittel - Google Patents

Das pflanzenwachstum regulierende mittel Download PDF

Info

Publication number: DD239108A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; phenyl; damages; halogen; alkoxy
Prior art date: 1984-11-23

Application number

DD85283096A

Other languages

German (de)

English (en)

Inventor

Roland Schmierer

Ernst-Friedrich Schulze

Helmut Buerstell

Erwin Hacker

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.)

1984-11-23

Filing date

1985-11-21

Publication date

1986-09-17

1985-11-21 Application filed by ��@��k�� filed Critical ��@��k��

1986-09-17 Publication of DD239108A5 publication Critical patent/DD239108A5/de

Links

230000001105 regulatory effect Effects 0.000 title abstract description 7
230000008635 plant growth Effects 0.000 title abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 60
-1 organic compound cation Chemical class 0.000 claims abstract description 27
239000002904 solvent Substances 0.000 claims abstract description 17
239000003630 growth substance Substances 0.000 claims abstract description 13
238000009736 wetting Methods 0.000 claims abstract description 6
239000000853 adhesive Substances 0.000 claims abstract description 5
230000001070 adhesive effect Effects 0.000 claims abstract description 5
230000001804 emulsifying effect Effects 0.000 claims abstract description 5
230000035515 penetration Effects 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
150000002367 halogens Chemical class 0.000 claims description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000003282 alkyl amino group Chemical group 0.000 claims description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000003944 tolyl group Chemical group 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
125000005059 halophenyl group Chemical group 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
239000000945 filler Substances 0.000 claims description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
125000006277 halobenzyl group Chemical group 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000006178 methyl benzyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 2
125000005499 phosphonyl group Chemical group 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
125000001425 triazolyl group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 2
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
125000006313 (C5-C8) alkyl group Chemical group 0.000 claims 1
230000026267 regulation of growth Effects 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 23
150000003839 salts Chemical class 0.000 abstract description 19
239000003795 chemical substances by application Substances 0.000 abstract description 14
239000013543 active substance Substances 0.000 abstract description 9
239000005648 plant growth regulator Substances 0.000 abstract description 4
238000011049 filling Methods 0.000 abstract description 2
230000000149 penetrating effect Effects 0.000 abstract description 2
FSVMTMFHLLEQAS-UHFFFAOYSA-N 3-phenylimidazole-4-carboxylic acid Chemical class OC(=O)C1=CN=CN1C1=CC=CC=C1 FSVMTMFHLLEQAS-UHFFFAOYSA-N 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
241000196324 Embryophyta Species 0.000 description 14
230000000694 effects Effects 0.000 description 14
230000012010 growth Effects 0.000 description 14
230000009036 growth inhibition Effects 0.000 description 14
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
150000001768 cations Chemical class 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
238000009472 formulation Methods 0.000 description 9
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
239000011347 resin Substances 0.000 description 8
229920005989 resin Polymers 0.000 description 8
239000002253 acid Substances 0.000 description 7
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
NIOYEINNWHTIIM-UHFFFAOYSA-N 3-(2,6-diethylphenyl)imidazole-4-carboxylic acid Chemical compound CCC1=CC=CC(CC)=C1N1C(C(O)=O)=CN=C1 NIOYEINNWHTIIM-UHFFFAOYSA-N 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
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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
230000015572 biosynthetic process Effects 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
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JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
230000002195 synergetic effect Effects 0.000 description 4
239000005995 Aluminium silicate Substances 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
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
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
241000209140 Triticum Species 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
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238000009835 boiling Methods 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
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239000003337 fertilizer Substances 0.000 description 3
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230000005764 inhibitory process 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
239000000463 material Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
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
KUTKVAQQQHGYGN-UHFFFAOYSA-M 2-chloroethyl(trimethyl)azanium;3-(2,6-diethylphenyl)imidazole-4-carboxylate Chemical compound C[N+](C)(C)CCCl.CCC1=CC=CC(CC)=C1N1C(C([O-])=O)=CN=C1 KUTKVAQQQHGYGN-UHFFFAOYSA-M 0.000 description 2
UEJNGUGKOFUMJK-UHFFFAOYSA-N 3-(2,6-diethylphenyl)imidazole-4-carboxylate;(2-ethoxy-2-oxoethyl)azanium Chemical compound CCOC(=O)C[NH3+].CCC1=CC=CC(CC)=C1N1C(C([O-])=O)=CN=C1 UEJNGUGKOFUMJK-UHFFFAOYSA-N 0.000 description 2
MHIVXHQGMNOIHI-UHFFFAOYSA-N 3-(2,6-diethylphenyl)imidazole-4-carboxylate;methylazanium Chemical compound [NH3+]C.CCC1=CC=CC(CC)=C1N1C(C([O-])=O)=CN=C1 MHIVXHQGMNOIHI-UHFFFAOYSA-N 0.000 description 2
QBJGAIPRMVHTBG-UHFFFAOYSA-M 3-(2,6-diethylphenyl)imidazole-4-carboxylate;tetraethylazanium Chemical compound CC[N+](CC)(CC)CC.CCC1=CC=CC(CC)=C1N1C(C([O-])=O)=CN=C1 QBJGAIPRMVHTBG-UHFFFAOYSA-M 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
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235000007164 Oryza sativa Nutrition 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
235000007238 Secale cereale Nutrition 0.000 description 2
229910004298 SiO 2 Inorganic materials 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
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150000002430 hydrocarbons Chemical class 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
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150000005309 metal halides Chemical class 0.000 description 2
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230000000885 phytotoxic effect Effects 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
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RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
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RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
230000009105 vegetative growth Effects 0.000 description 2
UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 1
125000006536 (C1-C2)alkoxy group Chemical group 0.000 description 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
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
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-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
ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 description 1
HBGZHBLJOQMVFE-UHFFFAOYSA-M 3-(2,6-diethylphenyl)imidazole-4-carboxylate;2-hydroxyethyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCO.CCC1=CC=CC(CC)=C1N1C(C([O-])=O)=CN=C1 HBGZHBLJOQMVFE-UHFFFAOYSA-M 0.000 description 1
SVVOIUFGZCHNTC-UHFFFAOYSA-N 3-(2,6-dimethylphenyl)imidazole-4-carboxylic acid Chemical compound CC1=CC=CC(C)=C1N1C(C(O)=O)=CN=C1 SVVOIUFGZCHNTC-UHFFFAOYSA-N 0.000 description 1
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 1
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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150000001298 alcohols Chemical class 0.000 description 1
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229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000002877 alkyl aryl group Chemical group 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
239000008346 aqueous phase Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-O argininium(1+) Chemical compound NC(=[NH2+])NCCCC([NH3+])C([O-])=O ODKSFYDXXFIFQN-UHFFFAOYSA-O 0.000 description 1
239000002363 auxin Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
239000002585 base 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
239000011230 binding agent Substances 0.000 description 1
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BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
JUZXDNPBRPUIOR-UHFFFAOYSA-N chlormequat Chemical compound C[N+](C)(C)CCCl JUZXDNPBRPUIOR-UHFFFAOYSA-N 0.000 description 1
UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
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239000004062 cytokinin Substances 0.000 description 1
UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004090 dissolution 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
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
CBYZIWCZNMOEAV-UHFFFAOYSA-N formaldehyde;naphthalene Chemical class O=C.C1=CC=CC2=CC=CC=C21 CBYZIWCZNMOEAV-UHFFFAOYSA-N 0.000 description 1
230000028245 fruit abscission Effects 0.000 description 1
239000000417 fungicide 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
ISNICOKBNZOJQG-UHFFFAOYSA-O guanidinium ion Chemical compound C[NH+]=C(N(C)C)N(C)C ISNICOKBNZOJQG-UHFFFAOYSA-O 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000003944 halohydrins Chemical class 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WTDHULULXKLSOZ-UHFFFAOYSA-N hydroxylamine hydrochloride Substances Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
WCYJQVALWQMJGE-UHFFFAOYSA-M hydroxylammonium chloride Chemical compound [Cl-].O[NH3+] WCYJQVALWQMJGE-UHFFFAOYSA-M 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
229920002113 octoxynol Polymers 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000008121 plant development Effects 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
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
239000010453 quartz Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
230000036435 stunted growth Effects 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
DPOWHSMECVNHAT-YERPJTIDSA-N tetcyclacis Chemical compound C1=CC(Cl)=CC=C1N1[C@H]2[C@H]([C@@H]3[C@H]4N=N3)C[C@H]4[C@H]2N=N1 DPOWHSMECVNHAT-YERPJTIDSA-N 0.000 description 1
HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 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
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Wood Science & Technology (AREA)
Agronomy & Crop Science (AREA)
Biochemistry (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Molecular Biology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Hydrogenated Pyridines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

DD85283096A 1984-11-23 1985-11-21 Das pflanzenwachstum regulierende mittel DD239108A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19843442690 DE3442690A1 (de)	1984-11-23	1984-11-23	Salze von 1-phenyl-imidazol-5-carbonsaeuren, ein verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren

Publications (1)

Publication Number	Publication Date
DD239108A5 true DD239108A5 (de)	1986-09-17

Family

ID=6250940

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD85283096A DD239108A5 (de)	1984-11-23	1985-11-21	Das pflanzenwachstum regulierende mittel

Country Status (14)

Country	Link
US (1)	US4775406A (da)
EP (1)	EP0182246A1 (da)
JP (1)	JPS61137867A (da)
AU (1)	AU5035685A (da)
BR (1)	BR8505885A (da)
DD (1)	DD239108A5 (da)
DE (1)	DE3442690A1 (da)
DK (1)	DK542685A (da)
ES (1)	ES8605490A1 (da)
HU (1)	HUT39958A (da)
IL (1)	IL77112A0 (da)
PH (1)	PH22244A (da)
SU (1)	SU1450727A3 (da)
ZA (1)	ZA858979B (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3808896A1 (de) *	1988-03-17	1989-09-28	Hoechst Ag	Pflanzenschuetzende mittel auf basis von pyrazolcarbonsaeurederivaten
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
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.

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2732531A1 (de) *	1977-07-19	1979-02-01	Hoechst Ag	Imidazolcarbonsaeuren und deren derivate
US4437875A (en) *	1980-04-14	1984-03-20	Monsanto Company	2,4-Disubstituted-5-thiazole-carboxylic acids and derivatives
KR810000359B1 (ko) *	1980-03-31	1981-04-22	한국과학기술원	히드록시메틸이미다졸 화합물의 제조방법
US4525202A (en) *	1981-08-24	1985-06-25	Stauffer Chemical Co.	Phosphonium salts of N-phosphonomethylglycine and their use as herbicides and plant growth regulants
DE3217094A1 (de) *	1982-05-07	1983-11-10	Hoechst Ag, 6230 Frankfurt	1-substituierte imidazol-5-carbonsaeurederivate, ihre herstellung sowie ihre verwendung als biozide
US4554013A (en) *	1983-08-02	1985-11-19	American Cyanamid Company	Herbicidal imidazolinyl naphthoic acids

1984
- 1984-11-23 DE DE19843442690 patent/DE3442690A1/de not_active Withdrawn
1985
- 1985-11-12 EP EP85114339A patent/EP0182246A1/de not_active Withdrawn
- 1985-11-21 HU HU854443A patent/HUT39958A/hu unknown
- 1985-11-21 DD DD85283096A patent/DD239108A5/de unknown
- 1985-11-21 IL IL77112A patent/IL77112A0/xx unknown
- 1985-11-21 PH PH33078A patent/PH22244A/en unknown
- 1985-11-21 ES ES549146A patent/ES8605490A1/es not_active Expired
- 1985-11-21 US US06/800,608 patent/US4775406A/en not_active Expired - Fee Related
- 1985-11-22 SU SU853982433A patent/SU1450727A3/ru active
- 1985-11-22 AU AU50356/85A patent/AU5035685A/en not_active Abandoned
- 1985-11-22 ZA ZA858979A patent/ZA858979B/xx unknown
- 1985-11-22 JP JP60261591A patent/JPS61137867A/ja active Pending
- 1985-11-22 BR BR8505885A patent/BR8505885A/pt unknown
- 1985-11-22 DK DK542685A patent/DK542685A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
EP0182246A1 (de)	1986-05-28
HUT39958A (en)	1986-11-28
DK542685A (da)	1986-05-24
US4775406A (en)	1988-10-04
DE3442690A1 (de)	1986-05-28
BR8505885A (pt)	1986-08-12
SU1450727A3 (ru)	1989-01-07
ES549146A0 (es)	1986-04-01
DK542685D0 (da)	1985-11-22
ES8605490A1 (es)	1986-04-01
PH22244A (en)	1988-07-01
IL77112A0 (en)	1986-04-29
AU5035685A (en)	1986-05-29
ZA858979B (en)	1986-07-30
JPS61137867A (ja)	1986-06-25

Publication	Publication Date	Title
DE2429523C2 (da)	1988-07-21
EP0004317B1 (de)	1982-01-06	Neue Phenoxy-alkancarbonsäurederivate, deren Herstellung, sie enthaltende herbizide Mittel und deren Verwendung
DD201640A5 (de)	1983-08-03	Herbizide mittel
DD219104A5 (de)	1985-02-27	Zusammensetzung fuer den einsatz als pflanzenwachstumsregulator
EP0137868B1 (de)	1987-08-12	1-Substituierte Imidazol-5-carbonsäurederivate, ihre Herstellung sowie ihre Verwendung als Biozide
EP0360181A2 (de)	1990-03-28	Salze von Herbizid-Säuren mit langkettigen Stickstoffbasen
DD261951A5 (de)	1988-11-16	Pflanzenwachstumsregulierende mittel
DD253755A5 (de)	1988-02-03	Cyclohexyl-und cyclohexenylimidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel
EP0484279B1 (de)	1996-02-28	Fungizide Mittel
DE3605551A1 (de)	1987-09-10	Fungizide mittel
EP0024259B1 (de)	1985-07-31	Derivate der 5-(Pyridyl-2-oxy)-2-nitrobenzoesäure, deren Herstellung und sie enthaltende herbizide Mittel
EP0185961A2 (de)	1986-07-02	1-Phenyl-imidazol-5-carbonsäure-Derivate, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Wachstumsregulatoren
EP0075840B1 (de)	1987-11-11	Heterocyclische Phenyläther, Verfahren zu deren Herstellung und diese enthaltende herbizide Mittel
EP0243615B1 (de)	1991-03-20	1-Phenylimidazolcarbonsäureamide, ihre Herstellung sowie ihre Verwendung als Wachstumsregulatoren
EP0013660B1 (de)	1983-05-18	Aminoalkylester der 2-Nitro-5-(ortho-chlor-para-trifluor-methylphenoxy)-benzoesäure, deren Herstellung, sie als Wirkstoff enthaltende herbizide Mittel und deren Verwendung
EP0167776A1 (de)	1986-01-15	Pflanzenwachstumsregulierende Mittel
DD239108A5 (de)	1986-09-17	Das pflanzenwachstum regulierende mittel
DD271447A5 (de)	1989-09-06	Verfahren zur regulierung des wachstums von pflanzen
DD259124A5 (de)	1988-08-17	Pflanzenwachstumsregulierende mittel
DE3309765A1 (de)	1984-09-20	Fungizide mittel
DE3736651C2 (de)	1995-11-23	Fungizide Wirkstoffkombinationen
DD218268A5 (de)	1985-02-06	Herbizide zusammensetzung
EP1202627B1 (de)	2003-06-18	Fungizide wirkstoffkombinationen
EP0029001B1 (de)	1984-03-21	Alpha-Phenoxy-propionyl-Azole, deren Herstellung, sie enthaltende herbizide Mittel und deren Verwendung
DE3333449A1 (de)	1985-04-11	Fungizide mittel