DE19532066A1 - Substituierte 5-Aminopyrazole - Google Patents

Substituierte 5-Aminopyrazole

Info

Publication number: DE19532066A1
Authority: DE; Germany
Prior art keywords: formula; compounds; meaning given; alkyl; optionally substituted
Prior art date: 1995-08-31
Legal status (The legal status 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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

DE1995132066

Other languages

German (de)

English (en)

Inventor

Markus Dipl Chem Dr Heil

Christoph Dr Erdelen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1995-08-31

Filing date

1995-08-31

Publication date

1997-03-06

1995-08-31 Application filed by Bayer AG filed Critical Bayer AG

1995-08-31 Priority to DE1995132066 priority Critical patent/DE19532066A1/de

1996-08-19 Priority to AU68741/96A priority patent/AU6874196A/en

1996-08-19 Priority to PCT/EP1996/003638 priority patent/WO1997008149A1/fr

1997-03-06 Publication of DE19532066A1 publication Critical patent/DE19532066A1/de

Status Withdrawn legal-status Critical Current

Links

JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 title claims abstract description 20
150000001875 compounds Chemical class 0.000 claims abstract description 48
238000000034 method Methods 0.000 claims abstract description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 13
241000607479 Yersinia pestis Species 0.000 claims abstract description 9
125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
125000001424 substituent group Chemical group 0.000 claims abstract description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 28
239000000460 chlorine Substances 0.000 claims description 28
229910052801 chlorine Inorganic materials 0.000 claims description 28
125000004093 cyano group Chemical group *C#N 0.000 claims description 18
239000003085 diluting agent Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical group 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 11
150000002431 hydrogen Chemical group 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 8
229910052717 sulfur Chemical group 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 7
239000011593 sulfur Chemical group 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
239000000575 pesticide Substances 0.000 claims description 4
125000000547 substituted alkyl group Chemical group 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
239000004606 Fillers/Extenders Substances 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000129 anionic group Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
125000001072 heteroaryl group Chemical group 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
241001465754 Metazoa Species 0.000 abstract description 4
-1 C1-C4-alkylthio Chemical group 0.000 description 55
239000002904 solvent Substances 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 24
229910052794 bromium Inorganic materials 0.000 description 24
239000004480 active ingredient Substances 0.000 description 23
229910052731 fluorine Inorganic materials 0.000 description 23
239000011737 fluorine Substances 0.000 description 23
239000000203 mixture Substances 0.000 description 21
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 20
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 20
239000000126 substance Substances 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
238000009472 formulation Methods 0.000 description 11
239000002023 wood Substances 0.000 description 11
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 10
239000011230 binding agent Substances 0.000 description 10
241000238631 Hexapoda Species 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000003995 emulsifying agent Substances 0.000 description 9
239000000463 material Substances 0.000 description 9
239000000243 solution Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
125000005843 halogen group Chemical group 0.000 description 8
239000002917 insecticide Substances 0.000 description 8
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 7
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000012141 concentrate Substances 0.000 description 7
239000011877 solvent mixture Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000000370 acceptor Substances 0.000 description 6
238000009835 boiling Methods 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
239000000417 fungicide Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000843 powder Substances 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
238000012360 testing method Methods 0.000 description 6
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
241001177134 Lyctus Species 0.000 description 5
229920000180 alkyd Polymers 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000000975 dye Substances 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
238000002156 mixing Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000011734 sodium Substances 0.000 description 5
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 4
241000239223 Arachnida Species 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
240000007124 Brassica oleracea Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
241000254173 Coleoptera Species 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
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
241000244206 Nematoda Species 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
125000001246 bromo group Chemical group Br* 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000012545 processing Methods 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000011347 resin Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 3
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 3
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 3
KNCHDRLWPAKSII-UHFFFAOYSA-N 4-ethyl-2-methylpyridine Chemical group CCC1=CC=NC(C)=C1 KNCHDRLWPAKSII-UHFFFAOYSA-N 0.000 description 3
UNNGFPDGTGXOKQ-UHFFFAOYSA-N 5-amino-1-cyclohexylpyrazole-3,4-dicarbonitrile Chemical compound NC1=C(C#N)C(C#N)=NN1C1CCCCC1 UNNGFPDGTGXOKQ-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
241000500437 Plutella xylostella Species 0.000 description 3
238000007792 addition Methods 0.000 description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000010949 copper Substances 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000012973 diazabicyclooctane Substances 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
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239000003960 organic solvent Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011435 rock Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
235000015112 vegetable and seed oil Nutrition 0.000 description 3
239000008158 vegetable oil Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 2
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125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 2
125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 description 2
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125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 2
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125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 description 2
125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
BWQFQKZDLBJZAW-UHFFFAOYSA-N 1,3-dichloro-2-fluoro-5-(trifluoromethyl)benzene Chemical compound FC1=C(Cl)C=C(C(F)(F)F)C=C1Cl BWQFQKZDLBJZAW-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 2
PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 2
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 description 2
UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 2
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AVGVFDSUDIUXEU-UHFFFAOYSA-N 2-octyl-1,2-thiazolidin-3-one Chemical compound CCCCCCCCN1SCCC1=O AVGVFDSUDIUXEU-UHFFFAOYSA-N 0.000 description 2
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240000003291 Armoracia rusticana Species 0.000 description 2
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235000011303 Brassica alboglabra Nutrition 0.000 description 2
235000011302 Brassica oleracea Nutrition 0.000 description 2
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235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
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WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
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FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
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IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
239000005822 Propiconazole Substances 0.000 description 2
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OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- C07D231/14—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 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
- C07D231/38—Nitrogen 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
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

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

DE1995132066 1995-08-31 1995-08-31 Substituierte 5-Aminopyrazole Withdrawn DE19532066A1 (de)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
DE1995132066 DE19532066A1 (de)	1995-08-31	1995-08-31	Substituierte 5-Aminopyrazole
AU68741/96A AU6874196A (en)	1995-08-31	1996-08-19	Substituted 5-aminopyrazols and their use for controlling animal pests
PCT/EP1996/003638 WO1997008149A1 (fr)	1995-08-31	1996-08-19	5-aminopyrazoles substitues et leur utilisation pour combattre des animaux nuisibles

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE1995132066 DE19532066A1 (de)	1995-08-31	1995-08-31	Substituierte 5-Aminopyrazole

Publications (1)

Publication Number	Publication Date
DE19532066A1 true DE19532066A1 (de)	1997-03-06

Family

ID=7770860

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE1995132066 Withdrawn DE19532066A1 (de)	1995-08-31	1995-08-31	Substituierte 5-Aminopyrazole

Country Status (3)

Country	Link
AU (1)	AU6874196A (fr)
DE (1)	DE19532066A1 (fr)
WO (1)	WO1997008149A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR042067A1 (es)	2002-11-27	2005-06-08	Bayer Pharmaceuticals Corp	Derivados de anilinopirazol utiles en el tratamiento de la diabetes

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT649407A (fr) *	1960-04-14
HUT69739A (en) *	1992-03-26	1995-09-28	Dowelanco	Process for producing n-heterocyclic nitroanilines and fungicides containing the compounds
DE4405207A1 (de) *	1994-02-18	1995-08-24	Bayer Ag	N-Pyrazolylaniline und N-Pyrazolylaminopyridine
US5488055A (en) *	1995-03-10	1996-01-30	Sanofi Winthrop Inc.	Substituted N-cycloalkylmethyl-1H-pyrazolo(3,4-b)quinolin-4 amines and compositions and methods of use thereof

1995
- 1995-08-31 DE DE1995132066 patent/DE19532066A1/de not_active Withdrawn
1996
- 1996-08-19 WO PCT/EP1996/003638 patent/WO1997008149A1/fr not_active Ceased
- 1996-08-19 AU AU68741/96A patent/AU6874196A/en not_active Abandoned

Also Published As

Publication number	Publication date
AU6874196A (en)	1997-03-19
WO1997008149A1 (fr)	1997-03-06

Publication	Publication Date	Title
EP0942904B1 (fr)	2004-06-23	Derives de 3-thiocarbamoylpyrazole utilises comme pesticides
DE19603576A1 (de)	1997-08-07	Acylierte 4-Amino und 4-Hydrazinopyrimidine
EP0861241B1 (fr)	2004-04-14	5-aminoisothiazoles acyles avec effet insecticide, produits intermediaires et procede de production correspondant
DE19601139A1 (de)	1997-07-17	Acylierte 5-Amino-1,2,4-thiadiazole
DE19628569A1 (de)	1998-01-22	Substituierte N-(5-Isothiazolyl)-thioamide
DE19548419A1 (de)	1997-06-26	Substituierte Thiazoline
DE19630814A1 (de)	1998-02-05	Substituierte N-Isothiazolyl-(thio)amide
EP0802907A1 (fr)	1997-10-29	5-aminopyrazoles acyles et leur utilisation pour lutter contre les parasites animaux
DE19544799A1 (de)	1997-06-05	Substituierte 5-Aminopyrazole
WO1996018619A1 (fr)	1996-06-20	Derives de m-diphenyloxazoline substitues
DE19529411A1 (de)	1997-02-13	Substituierte Tetrahydro-5-nitro-pyrimidine
EP0885225B1 (fr)	2002-01-23	Derives de tetrahydropyrimidine
DE19605400A1 (de)	1997-08-21	Salze von Imidazolin-Derivaten
EP0854871B1 (fr)	2000-08-16	1,3,4-oxadiazolin-2-ones et leur utilisation comme pesticides
DE19532066A1 (de)	1997-03-06	Substituierte 5-Aminopyrazole
DE19536842A1 (de)	1997-03-13	Uracil-Derivate
EP0991631A1 (fr)	2000-04-12	Aminoheterocyclylamides substitues
DE19625263A1 (de)	1998-01-02	Substituierte N-(4-Pyridyl)-thioamide
EP0944608B1 (fr)	2003-04-16	4-cyclohexylphenyloxazolines et leur utilisation pour combattre les parasites animaux
EP1044188A1 (fr)	2000-10-18	Derives de 4-aminopyridine acyles utilises comme pesticides et fongicides
WO1997006153A1 (fr)	1997-02-20	Derives de 4-alkyl-1,3-oxa(thia)zoline, leur preparation et leur utilisation pour detruire des animaux parasites
DE19651429A1 (de)	1997-09-11	Tetrahydropyrimidin-Derivate
DE19544798A1 (de)	1997-06-05	Substituierte 3-Thiocarbamoyl-5-amino-pyrazole
DE19750402A1 (de)	1999-05-20	Acylierte 4-Amino-pyridine
DE19750401A1 (de)	1999-05-20	Kondensierte Pyridin-Derivate

Legal Events

Date	Code	Title	Description
1999-10-07	8139	Disposal/non-payment of the annual fee