DD253755A5 - Cyclohexyl-und cyclohexenylimidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel - Google Patents

Cyclohexyl-und cyclohexenylimidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel Download PDF

Info

Publication number: DD253755A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; phenyl; alkoxy; halogen; substituted
Prior art date: 1985-04-19

Application number

DD86289308A

Other languages

German (de)

English (en)

Inventor

Roland Schmierer

Hilmar Mildenberger

Reinhard Handte

Helmut Buerstell

Burkhard Sachse

Klaus Bauer

Hermann Bieringer

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.)

1985-04-19

Filing date

1986-04-17

Publication date

1988-02-03

1986-04-17 Application filed by ��@��k�� filed Critical ��@��k��

1988-02-03 Publication of DD253755A5 publication Critical patent/DD253755A5/de

Links

-1 CYCLOHEXYL Chemical class 0.000 title claims abstract description 41
238000000034 method Methods 0.000 title claims description 11
239000011814 protection agent Substances 0.000 title claims description 4
238000004519 manufacturing process Methods 0.000 title description 2
QPJZLVKOIFKVDP-UHFFFAOYSA-N 2-(cyclohexen-1-yl)-1h-imidazole Chemical class C1CCCC(C=2NC=CN=2)=C1 QPJZLVKOIFKVDP-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 68
150000003839 salts Chemical class 0.000 claims abstract description 14
241000233866 Fungi Species 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims description 63
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
229910052736 halogen Inorganic materials 0.000 claims description 30
150000002367 halogens Chemical class 0.000 claims description 25
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 24
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
125000003342 alkenyl group Chemical group 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 15
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 11
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
238000005956 quaternization reaction Methods 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 8
150000001768 cations Chemical class 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 7
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
229910052799 carbon Inorganic materials 0.000 claims description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
125000006331 halo benzoyl group Chemical group 0.000 claims description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000002883 imidazolyl group Chemical group 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
125000001425 triazolyl group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
150000007942 carboxylates Chemical class 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000006277 halobenzyl group Chemical group 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 2
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
125000004802 cyanophenyl group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
125000000466 oxiranyl group Chemical group 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
239000004476 plant protection product Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
125000004432 carbon atom Chemical group C* 0.000 claims 2
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
125000006529 (C3-C6) alkyl group Chemical group 0.000 claims 1
229910016467 AlCl 4 Inorganic materials 0.000 claims 1
125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 17
230000002363 herbicidal effect Effects 0.000 abstract description 14
239000000126 substance Substances 0.000 abstract description 7
230000000855 fungicidal effect Effects 0.000 abstract description 5
230000001105 regulatory effect Effects 0.000 abstract description 3
239000000575 pesticide Substances 0.000 abstract description 2
SWSQLWCPSIPFQT-UHFFFAOYSA-N 3-(cyclohexen-1-yl)imidazole-4-carboxylic acid Chemical class OC(=O)C1=CN=CN1C1=CCCCC1 SWSQLWCPSIPFQT-UHFFFAOYSA-N 0.000 abstract 1
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
239000000700 radioactive tracer Substances 0.000 abstract 1
241000196324 Embryophyta Species 0.000 description 54
239000004480 active ingredient Substances 0.000 description 20
230000012010 growth Effects 0.000 description 18
240000007594 Oryza sativa Species 0.000 description 17
239000003921 oil Substances 0.000 description 17
230000000694 effects Effects 0.000 description 16
235000007164 Oryza sativa Nutrition 0.000 description 12
235000009566 rice Nutrition 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000013543 active substance Substances 0.000 description 11
230000006378 damage Effects 0.000 description 11
150000003254 radicals Chemical class 0.000 description 11
206010061217 Infestation Diseases 0.000 description 10
241000209140 Triticum Species 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
241000221785 Erysiphales Species 0.000 description 9
240000005979 Hordeum vulgare Species 0.000 description 8
235000021307 Triticum Nutrition 0.000 description 8
238000009472 formulation Methods 0.000 description 8
235000007340 Hordeum vulgare Nutrition 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
239000008187 granular material Substances 0.000 description 7
238000002156 mixing Methods 0.000 description 7
239000011347 resin Substances 0.000 description 7
229920005989 resin Polymers 0.000 description 7
239000002253 acid Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000003814 drug Substances 0.000 description 6
229940079593 drug Drugs 0.000 description 6
239000004495 emulsifiable concentrate Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
235000010469 Glycine max Nutrition 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
230000009036 growth inhibition Effects 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229920001817 Agar Polymers 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
241000123650 Botrytis cinerea Species 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
229910002651 NO3 Inorganic materials 0.000 description 4
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
244000082988 Secale cereale Species 0.000 description 4
235000007238 Secale cereale Nutrition 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000008272 agar Substances 0.000 description 4
239000003795 chemical substances by application Substances 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
239000006185 dispersion Substances 0.000 description 4
238000011081 inoculation Methods 0.000 description 4
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007921 spray Substances 0.000 description 4
240000008067 Cucumis sativus Species 0.000 description 3
241000234653 Cyperus Species 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000839 emulsion 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
150000002191 fatty alcohols Chemical class 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000000463 material Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
230000000885 phytotoxic effect Effects 0.000 description 3
239000005648 plant growth regulator Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
239000000047 product Substances 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
239000002689 soil Substances 0.000 description 3
241000894007 species Species 0.000 description 3
239000000725 suspension 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
230000009105 vegetative growth Effects 0.000 description 3
UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
241001480061 Blumeria graminis Species 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
229920000742 Cotton Polymers 0.000 description 2
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
244000299507 Gossypium hirsutum Species 0.000 description 2
239000005867 Iprodione Substances 0.000 description 2
BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
235000011999 Panicum crusgalli Nutrition 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
229910004298 SiO 2 Inorganic materials 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000000853 adhesive Substances 0.000 description 2
230000001070 adhesive effect Effects 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
JUZXDNPBRPUIOR-UHFFFAOYSA-N chlormequat Chemical compound C[N+](C)(C)CCCl JUZXDNPBRPUIOR-UHFFFAOYSA-N 0.000 description 2
244000038559 crop plants Species 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
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239000000945 filler Substances 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
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239000003630 growth substance Substances 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
238000011534 incubation Methods 0.000 description 2
ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 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
230000007774 longterm Effects 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
150000004714 phosphonium salts Chemical class 0.000 description 2
230000008635 plant growth Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 2
229940116357 potassium thiocyanate Drugs 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 1
125000006545 (C1-C9) alkyl group Chemical group 0.000 description 1
125000006313 (C5-C8) alkyl group Chemical group 0.000 description 1
OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical class SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 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
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 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
UDPGUMQDCGORJQ-UHFFFAOYSA-M 2-chloroethyl(hydroxy)phosphinate Chemical compound OP([O-])(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-M 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
229930192334 Auxin Natural products 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical class OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
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CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
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ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
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239000005976 Ethephon Substances 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241000223218 Fusarium Species 0.000 description 1
241000896246 Golovinomyces cichoracearum Species 0.000 description 1
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235000011152 sodium sulphate Nutrition 0.000 description 1
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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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon 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
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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
- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DD86289308A 1985-04-19 1986-04-17 Cyclohexyl-und cyclohexenylimidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel DD253755A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853514116 DE3514116A1 (de)	1985-04-19	1985-04-19	Neue cyclohexyl- und cyclohexenylimidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatoren

Publications (1)

Publication Number	Publication Date
DD253755A5 true DD253755A5 (de)	1988-02-03

Family

ID=6268545

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86289308A DD253755A5 (de)	1985-04-19	1986-04-17	Cyclohexyl-und cyclohexenylimidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel

Country Status (13)

Country	Link
US (1)	US4747868A (fr)
EP (1)	EP0199206A3 (fr)
JP (1)	JPS61249971A (fr)
KR (1)	KR860008149A (fr)
CN (1)	CN86102703A (fr)
AU (1)	AU5638686A (fr)
BR (1)	BR8601749A (fr)
DD (1)	DD253755A5 (fr)
DE (1)	DE3514116A1 (fr)
ES (1)	ES8704152A1 (fr)
HU (1)	HUT43046A (fr)
IL (1)	IL78530A0 (fr)
ZA (1)	ZA862924B (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8523255D0 (en) *	1985-09-20	1985-10-23	Shell Int Research	Imidazoles
DE3608143A1 (de) *	1986-03-12	1987-09-17	Hoechst Ag	1-phenylimidazolcarbonsaeureamide, ihre herstellung sowie ihre verwendung als wachstumsregulatoren
DE3627155A1 (de) *	1986-08-11	1988-02-18	Schering Ag	Imidazol-derivate
GB8629169D0 (en) *	1986-12-05	1987-01-14	Ici Plc	Chemical compounds
DE3751686T2 (de) *	1986-12-16	1996-06-13	Zeneca Ltd	Pyrrol-Derivate und ihre Verwendung in der Landwirtschaft
EP0277384A3 (fr) *	1986-12-24	1990-05-23	Janssen Pharmaceutica N.V.	Dérivés d'acide imidazole-5-carbonique
GB8631091D0 (en) *	1986-12-31	1987-02-04	Janssen Pharmaceutica Nv	1-cyclyl/polycyclyl substituted-1h-imidazone-5-carboxylic acids
IL84809A (en) *	1987-11-06	1992-12-01	Ciba Geigy	Process for the synthesis of 1-substituted imidazole- 5-carboxylic acids and derivatives thereof
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US6319156B1 (en) *	1999-12-13	2001-11-20	John Marshall	Biodegradable golf tee
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1985
- 1985-04-19 DE DE19853514116 patent/DE3514116A1/de not_active Withdrawn
1986
- 1986-04-10 EP EP86104952A patent/EP0199206A3/fr not_active Withdrawn
- 1986-04-17 US US06/853,018 patent/US4747868A/en not_active Expired - Fee Related
- 1986-04-17 ES ES554112A patent/ES8704152A1/es not_active Expired
- 1986-04-17 HU HU861612A patent/HUT43046A/hu unknown
- 1986-04-17 IL IL78530A patent/IL78530A0/xx unknown
- 1986-04-17 DD DD86289308A patent/DD253755A5/de unknown
- 1986-04-18 JP JP61088439A patent/JPS61249971A/ja active Pending
- 1986-04-18 CN CN198686102703A patent/CN86102703A/zh active Pending
- 1986-04-18 AU AU56386/86A patent/AU5638686A/en not_active Abandoned
- 1986-04-18 BR BR8601749A patent/BR8601749A/pt unknown
- 1986-04-18 ZA ZA862924A patent/ZA862924B/xx unknown
- 1986-04-19 KR KR1019860003041A patent/KR860008149A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
ES554112A0 (es)	1987-04-01
DE3514116A1 (de)	1986-10-23
CN86102703A (zh)	1987-02-04
EP0199206A2 (fr)	1986-10-29
ZA862924B (en)	1986-12-30
HUT43046A (en)	1987-09-28
US4747868A (en)	1988-05-31
JPS61249971A (ja)	1986-11-07
AU5638686A (en)	1986-10-23
IL78530A0 (en)	1986-08-31
KR860008149A (ko)	1986-11-12
EP0199206A3 (fr)	1987-04-08
ES8704152A1 (es)	1987-04-01
BR8601749A (pt)	1986-12-23

Publication	Publication Date	Title
EP0269806B1 (fr)	1991-02-27	Dérivés d'acide phénylpyrazolcarbonique, leur préparation et leur utilisation comme agents régulateurs de croissance des plantes et antidote
DE2648008C3 (de)	1980-09-04	Acetanilide
EP0137868B1 (fr)	1987-08-12	Dérivés d'acides imidazole-5-carboxyliques substitués en position 1, leur préparation et leur utilisation comme biocides
DE2815820C2 (fr)	1989-12-28
DD253755A5 (de)	1988-02-03	Cyclohexyl-und cyclohexenylimidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel
DD231481A5 (de)	1986-01-02	Herbizide und wachstumsregulierende mittel
EP0071794A1 (fr)	1983-02-16	Dérivés de l'acide 5-amino-1-phényl-pyrazol-4-carboxylique, leur procédé de préparation et leur application comme herbicides
DE4126937A1 (de)	1993-02-11	Salicyl(thio)etherderivate, verfahren und zwischenprodukte zu ihrer herstellung
DE2600799A1 (de)	1977-07-14	Acylierte triazolyl-0,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide
EP0185961A2 (fr)	1986-07-02	Dérivés d'acide 1-phényl-imidazole-5-carboxylique, procédé pour leur préparation et leur application comme régulateurs de croissance
DE3614364A1 (de)	1987-10-29	1-phenyl-imidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren
DE3537290A1 (de)	1987-04-23	1,2,5-substituierte imidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren
EP0053699A1 (fr)	1982-06-16	Esters de l'acide 2'-phénylhydrazino-2-cyanoacrylique et des herbicides les contenant
DE3145846A1 (de)	1983-05-26	Cycloalkyl-((alpha)-triazolyl-ss-hydroxy)-ketone, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und pflanzenwachstumsregulatoren
EP0013873B1 (fr)	1982-01-20	Anilides de l'acide N-azolyl acétique, procédé pour leur préparation et leur utilisation comme herbicides
DD144501A5 (de)	1980-10-22	Schaedlingsbekaempfungsmittel
DD233923A5 (de)	1986-03-19	Herbizide und wachstumsregulierende mittel
DD272405A5 (de)	1989-10-11	Fungizide mittel
DE3539476A1 (de)	1987-05-14	Neue pyridylverbindungen sowie deren n-oxide, verfahren zu ihrer herstellung und ihre verwendung im pflanzenschutz
DE3129193A1 (de)	1983-02-03	Azolderivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
DE2635967A1 (de)	1977-03-17	2-cyanacetamid-derivate und ihre herstellung und anwendung
EP0160931A2 (fr)	1985-11-13	Azolylvinyl éthers
DE3430005A1 (de)	1986-02-20	Neue alkylsulfonylpropene, verfahren zu ihrer herstellung und ihre verwendung
DE2551983A1 (de)	1976-05-26	Pyrazolidine und verfahren zu ihrer herstellung
DE3442690A1 (de)	1986-05-28	Salze von 1-phenyl-imidazol-5-carbonsaeuren, ein verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren