DD259124A5 - Pflanzenwachstumsregulierende mittel - Google Patents

Pflanzenwachstumsregulierende mittel Download PDF

Info

Publication number: DD259124A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; phenyl; alkoxy; halogen; substituted
Prior art date: 1985-10-19

Application number

DD86295354A

Other languages

German (de)

English (en)

Inventor

Roland Schmierer

Hilmar Mildenberger

Reinhard Handte

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.)

1985-10-19

Filing date

1986-10-17

Publication date

1988-08-17

1986-10-17 Application filed by ��@��k�� filed Critical ��@��k��

1988-08-17 Publication of DD259124A5 publication Critical patent/DD259124A5/de

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-1 compound compounds Chemical class 0.000 claims abstract description 55
229910052736 halogen Inorganic materials 0.000 claims abstract description 29
150000002367 halogens Chemical class 0.000 claims abstract description 29
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 18
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
239000001257 hydrogen Substances 0.000 claims abstract description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 12
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 11
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 10
239000003795 chemical substances by application Substances 0.000 claims abstract description 10
230000001105 regulatory effect Effects 0.000 claims abstract description 6
230000008635 plant growth Effects 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 50
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 19
150000001768 cations Chemical class 0.000 claims description 16
125000003342 alkenyl group Chemical group 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
150000007942 carboxylates Chemical class 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 3
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000003944 tolyl group Chemical group 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000000466 oxiranyl group Chemical group 0.000 claims description 2
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
150000003555 thioacetals Chemical class 0.000 claims description 2
125000001425 triazolyl group Chemical group 0.000 claims description 2
125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims 1
125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 21
150000002460 imidazoles Chemical class 0.000 abstract description 2
125000005115 alkyl carbamoyl group Chemical group 0.000 abstract 1
125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
241000196324 Embryophyta Species 0.000 description 20
150000003839 salts Chemical class 0.000 description 16
239000011347 resin Substances 0.000 description 14
229920005989 resin Polymers 0.000 description 14
230000012010 growth Effects 0.000 description 13
239000000203 mixture Substances 0.000 description 13
230000015572 biosynthetic process Effects 0.000 description 12
230000009036 growth inhibition Effects 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
229910052757 nitrogen Inorganic materials 0.000 description 10
150000003254 radicals Chemical class 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
238000009472 formulation Methods 0.000 description 9
238000005956 quaternization reaction Methods 0.000 description 9
230000000694 effects Effects 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
239000011734 sodium Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
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 7
239000013543 active substance Substances 0.000 description 7
125000005843 halogen group Chemical group 0.000 description 7
238000002156 mixing Methods 0.000 description 7
125000004433 nitrogen atom Chemical group N* 0.000 description 7
239000000047 product Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
238000000034 method Methods 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
230000000885 phytotoxic effect Effects 0.000 description 5
229920000151 polyglycol Polymers 0.000 description 5
239000010695 polyglycol Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical group OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
229910052801 chlorine Inorganic materials 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
125000006277 halobenzyl group Chemical group 0.000 description 4
239000000843 powder Substances 0.000 description 4
UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
KXHMJRLJEDQQRU-UHFFFAOYSA-N 2-benzylsulfanyl-3-(2,6-diethylphenyl)imidazole-4-carboxylic acid Chemical compound CCC1=CC=CC(CC)=C1N1C(C(O)=O)=CN=C1SCC1=CC=CC=C1 KXHMJRLJEDQQRU-UHFFFAOYSA-N 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
240000007594 Oryza sativa Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
239000003337 fertilizer Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
238000000227 grinding Methods 0.000 description 3
239000003630 growth substance Substances 0.000 description 3
125000006331 halo benzoyl group Chemical group 0.000 description 3
230000005764 inhibitory process Effects 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
239000003921 oil Substances 0.000 description 3
230000009105 vegetative growth Effects 0.000 description 3
125000006313 (C5-C8) alkyl group Chemical group 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
UHBOZMOZPQJQNZ-UHFFFAOYSA-N 3-(2,6-diethylphenyl)-2-sulfanylidene-1h-imidazole-4-carboxylic acid Chemical compound CCC1=CC=CC(CC)=C1N1C(=S)NC=C1C(O)=O UHBOZMOZPQJQNZ-UHFFFAOYSA-N 0.000 description 2
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
235000007238 Secale cereale Nutrition 0.000 description 2
229910004298 SiO 2 Inorganic materials 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
239000003513 alkali Substances 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000000969 carrier Substances 0.000 description 2
JUZXDNPBRPUIOR-UHFFFAOYSA-N chlormequat Chemical compound C[N+](C)(C)CCCl JUZXDNPBRPUIOR-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
125000004802 cyanophenyl group Chemical group 0.000 description 2
238000001212 derivatisation Methods 0.000 description 2
GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 2
SKDSTARRNIDRMN-UHFFFAOYSA-N ethyl 2-benzylsulfanyl-3-(2,6-diethylphenyl)imidazole-4-carboxylate Chemical compound CCC=1C=CC=C(CC)C=1N1C(C(=O)OCC)=CN=C1SCC1=CC=CC=C1 SKDSTARRNIDRMN-UHFFFAOYSA-N 0.000 description 2
LPIISIFXUVGJSY-UHFFFAOYSA-N ethyl 2-benzylsulfinyl-3-(2,6-diethylphenyl)imidazole-4-carboxylate Chemical compound CCOC(=O)C1=CN=C(S(=O)CC=2C=CC=CC=2)N1C1=C(CC)C=CC=C1CC LPIISIFXUVGJSY-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000006260 foam Substances 0.000 description 2
125000005059 halophenyl group Chemical group 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
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 2
239000007788 liquid Substances 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
238000006263 metalation reaction Methods 0.000 description 2
MLHQMCSOHUSFRV-UHFFFAOYSA-N methyl 3-(2,6-dimethylcyclohexyl)-2-sulfanylidene-1h-imidazole-4-carboxylate Chemical compound COC(=O)C1=CNC(=S)N1C1C(C)CCCC1C MLHQMCSOHUSFRV-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
125000006501 nitrophenyl group Chemical group 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
150000004714 phosphonium salts Chemical class 0.000 description 2
231100000208 phytotoxic Toxicity 0.000 description 2
239000005648 plant growth regulator Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
235000009566 rice Nutrition 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical class [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 2
125000005537 sulfoxonium group Chemical class 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
238000009736 wetting Methods 0.000 description 2
125000006526 (C1-C2) alkyl group Chemical group 0.000 description 1
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 1
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 1
125000004916 (C1-C6) alkylcarbonyl 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
CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical compound SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical compound ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 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
WNAZIEJFNAFGAW-UHFFFAOYSA-N 2-benzylsulfonyl-3-(2,6-diethylphenyl)imidazole-4-carboxylate;piperidin-1-ium Chemical compound C1CC[NH2+]CC1.CCC1=CC=CC(CC)=C1N1C(S(=O)(=O)CC=2C=CC=CC=2)=NC=C1C([O-])=O WNAZIEJFNAFGAW-UHFFFAOYSA-N 0.000 description 1
MGZLOSVXJYEMPG-UHFFFAOYSA-N 2-benzylsulfonyl-3-(2,6-diethylphenyl)imidazole-4-carboxylic acid Chemical compound CCC1=CC=CC(CC)=C1N1C(S(=O)(=O)CC=2C=CC=CC=2)=NC=C1C(O)=O MGZLOSVXJYEMPG-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
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-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
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
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
229930192334 Auxin Natural products 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
240000002791 Brassica napus Species 0.000 description 1
235000004977 Brassica sinapistrum Nutrition 0.000 description 1
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239000011230 binding agent Substances 0.000 description 1
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238000011097 chromatography purification Methods 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
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238000007796 conventional method Methods 0.000 description 1
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ZKULHOWDJPQDNJ-UHFFFAOYSA-N ethyl 3-(2,6-diethylphenyl)imidazole-4-carboxylate Chemical compound CCOC(=O)C1=CN=CN1C1=C(CC)C=CC=C1CC ZKULHOWDJPQDNJ-UHFFFAOYSA-N 0.000 description 1
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238000001704 evaporation Methods 0.000 description 1
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238000002474 experimental method Methods 0.000 description 1
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208000037824 growth disorder Diseases 0.000 description 1
239000003966 growth inhibitor Substances 0.000 description 1
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238000003306 harvesting Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
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239000012456 homogeneous solution Substances 0.000 description 1
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150000002430 hydrocarbons Chemical class 0.000 description 1
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239000002917 insecticide Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
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125000000468 ketone group Chemical group 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical class [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
229910052749 magnesium Inorganic materials 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
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
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230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002892 organic cations Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
238000006146 oximation reaction Methods 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000004841 phenylimidazoles Chemical class 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
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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
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
229940116357 potassium thiocyanate Drugs 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000026267 regulation of growth Effects 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
230000036435 stunted growth Effects 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003463 sulfur Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000002195 synergetic effect Effects 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
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
- 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
- C07D233/84—Sulfur atoms
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Agronomy & Crop Science (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

DD86295354A 1985-10-19 1986-10-17 Pflanzenwachstumsregulierende mittel DD259124A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853537290 DE3537290A1 (de)	1985-10-19	1985-10-19	1,2,5-substituierte imidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren

Publications (1)

Publication Number	Publication Date
DD259124A5 true DD259124A5 (de)	1988-08-17

Family

ID=6283990

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86295354A DD259124A5 (de)	1985-10-19	1986-10-17	Pflanzenwachstumsregulierende mittel

Country Status (10)

Country	Link
US (1)	US4764624A (da)
EP (1)	EP0219798A1 (da)
JP (1)	JPS6299362A (da)
AU (1)	AU6414286A (da)
DD (1)	DD259124A5 (da)
DE (1)	DE3537290A1 (da)
DK (1)	DK498086A (da)
HU (1)	HUT44766A (da)
IL (1)	IL80360A0 (da)
ZA (1)	ZA867883B (da)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3614364A1 (de) *	1986-04-28	1987-10-29	Hoechst Ag	1-phenyl-imidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren
EP0277384A3 (en) *	1986-12-24	1990-05-23	Janssen Pharmaceutica N.V.	1h-imidazole-5-carboxylic acid derivatives
GB8631091D0 (en) *	1986-12-31	1987-02-04	Janssen Pharmaceutica Nv	1-cyclyl/polycyclyl substituted-1h-imidazone-5-carboxylic acids
US4878940A (en) *	1987-04-02	1989-11-07	Janssen Pharmaceutica N.V.	Herbicidal 1,5-substituted 1H-imidazoles
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.
TWI702212B (zh)	2015-02-09	2020-08-21	德商拜耳作物科學股份有限公司	作為除害劑之經取代的２－硫基咪唑基羧醯胺類
EP3448845B1 (de)	2016-04-25	2020-11-04	Bayer CropScience Aktiengesellschaft	Substituierte 2-alkylimidazolyl-carboxamide als schädlingsbekämpfungsmittel
ES2858093T3 (es)	2016-08-10	2021-09-29	Bayer Cropscience Ag	2-Heterociclil-imidazolil-carboxamidas sustituidas como pesticidas

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2541924A (en) *	1948-09-17	1951-02-13	Lilly Co Eli	Synthesis of substituted imidazoles
DE2732531A1 (de) *	1977-07-19	1979-02-01	Hoechst Ag	Imidazolcarbonsaeuren und deren derivate
DE3217094A1 (de) *	1982-05-07	1983-11-10	Hoechst Ag, 6230 Frankfurt	1-substituierte imidazol-5-carbonsaeurederivate, ihre herstellung sowie ihre verwendung als biozide

1985
- 1985-10-19 DE DE19853537290 patent/DE3537290A1/de not_active Withdrawn
1986
- 1986-10-14 EP EP86114184A patent/EP0219798A1/de not_active Withdrawn
- 1986-10-16 HU HU864317A patent/HUT44766A/hu unknown
- 1986-10-16 US US06/919,881 patent/US4764624A/en not_active Expired - Fee Related
- 1986-10-17 ZA ZA867883A patent/ZA867883B/xx unknown
- 1986-10-17 JP JP61245627A patent/JPS6299362A/ja active Pending
- 1986-10-17 AU AU64142/86A patent/AU6414286A/en not_active Abandoned
- 1986-10-17 DD DD86295354A patent/DD259124A5/de unknown
- 1986-10-17 DK DK498086A patent/DK498086A/da not_active Application Discontinuation
- 1986-10-17 IL IL80360A patent/IL80360A0/xx unknown

Also Published As

Publication number	Publication date
ZA867883B (en)	1987-05-27
JPS6299362A (ja)	1987-05-08
IL80360A0 (en)	1987-01-30
HUT44766A (en)	1988-04-28
DK498086A (da)	1987-04-20
DK498086D0 (da)	1986-10-17
EP0219798A1 (de)	1987-04-29
AU6414286A (en)	1987-05-07
DE3537290A1 (de)	1987-04-23
US4764624A (en)	1988-08-16

Publication	Publication Date	Title
EP0269806B1 (de)	1991-02-27	Phenylpyrazolcarbonsäurederivate, ihre Herstellung und Verwendung als Pflanzenwachstumsregulatoren und Safener
EP0137868B1 (de)	1987-08-12	1-Substituierte Imidazol-5-carbonsäurederivate, ihre Herstellung sowie ihre Verwendung als Biozide
EP0011693A1 (de)	1980-06-11	Neue N-(trifluormethansulfonylaminophenyl)-substituierte N-Heterocyclen, ihre Herstellung, sie enthaltende Mittel und ihre Verwendung zur Beeinflussung des Pflanzenwachstums
DD231481A5 (de)	1986-01-02	Herbizide und wachstumsregulierende mittel
EP0007479B1 (de)	1982-12-29	N-Arylpropyl-substituierte cyclische Amine, Fungizide, die diese Verbindungen enthalten und Verfahren zu ihrer Herstellung
EP0000333B1 (de)	1982-07-28	Derivate cyclischer Amine und diese enthaltende Fungizide
DE3514116A1 (de)	1986-10-23	Neue cyclohexyl- und cyclohexenylimidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatoren
DD259124A5 (de)	1988-08-17	Pflanzenwachstumsregulierende mittel
DD261951A5 (de)	1988-11-16	Pflanzenwachstumsregulierende mittel
DE3841432A1 (de)	1990-06-21	Pyridinderivate und ihre verwendung als herbizide
DD259560A5 (de)	1988-08-31	Pflanzenwachstumsregulierende mittel
EP0185961A2 (de)	1986-07-02	1-Phenyl-imidazol-5-carbonsäure-Derivate, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Wachstumsregulatoren
EP0243615B1 (de)	1991-03-20	1-Phenylimidazolcarbonsäureamide, ihre Herstellung sowie ihre Verwendung als Wachstumsregulatoren
DD215931A5 (de)	1984-11-28	Fungizide mittel
DE3210009A1 (de)	1982-10-14	Imidazolderivate und diese enthaltende fungizide zusammensetzung
EP0151744A1 (de)	1985-08-21	1-Acylimidazolinone, Verfahren zu ihrer Herstellung und ihre Verwendung in der Landwirtschaft
EP0208281B1 (de)	1991-01-30	Chinolin-8-carbonsäureazolide, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
DE3313499A1 (de)	1984-10-18	1,2,4-triazol-1-yl-vinylether, ihre herstellung und ihre verwendung als pflanzenbehandlungsmittel
EP0182246A1 (de)	1986-05-28	Salze von 1-Phenyl-imidazol-5-carbonsäuren, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Wachstumsregulatoren
EP0009555A1 (de)	1980-04-16	Herbizide Mittel auf der Basis eines Thiolcarbamats, die Halogenacylamide als Antagonisten enthalten, und ihre Verwendung in einem Verfahren zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs
EP0275417A2 (de)	1988-07-27	Trifluormethylsubstituierte Azole, Verfahren zu ihrer Herstellung und ihre Verwendung als Mittel mit herbizider Wirkung
DE3101233A1 (de)	1982-08-26	N-3'-(p-tertiaer-butylphenyl)-2'-methyl-propyl-1'-piperidin-derivate, diese enthaltende fungizide und verfahren zur bekaempfung von pilzen mit diesen verbindungen
DD212884A5 (de)	1984-08-29	Pflanzenschutz- und wachstumsregulierende mittel
EP0456125A1 (de)	1991-11-13	N-Aryltetrahydrophthalimide und ihre Verwendung als Herbizide
EP0150499A2 (de)	1985-08-07	3-Substituierte Azolyl-butan-Derivate, Verfahren zu ihrer Herstellung und Fungizide für Landwirtschaft und Gartenbau