DD272298A5 - Verfahren zur herstellung von 4-nitro-n-phenylpyrazolderivaten und diese enthaltende zusammensetzungen - Google Patents
Verfahren zur herstellung von 4-nitro-n-phenylpyrazolderivaten und diese enthaltende zusammensetzungen Download PDFInfo
- Publication number
- DD272298A5 DD272298A5 DD88316724A DD31672488A DD272298A5 DD 272298 A5 DD272298 A5 DD 272298A5 DD 88316724 A DD88316724 A DD 88316724A DD 31672488 A DD31672488 A DD 31672488A DD 272298 A5 DD272298 A5 DD 272298A5
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- DD
- German Democratic Republic
- Prior art keywords
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- general formula
- compounds
- spp
- dichloro
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 68
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- IATFOGDERDNVMS-UHFFFAOYSA-N 4-nitro-1-phenylpyrazole Chemical class C1=C([N+](=O)[O-])C=NN1C1=CC=CC=C1 IATFOGDERDNVMS-UHFFFAOYSA-N 0.000 title abstract 2
- -1 chloro, bromo, iodo Chemical group 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 31
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 25
- 125000003277 amino group Chemical group 0.000 claims abstract description 23
- 239000000460 chlorine Chemical group 0.000 claims abstract description 21
- 125000005843 halogen group Chemical group 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 20
- 229910052794 bromium Chemical group 0.000 claims abstract description 18
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 15
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 239000011737 fluorine Substances 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical class 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 125000002252 acyl group Chemical class 0.000 claims abstract 3
- 150000003949 imides Chemical class 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 160
- 241000238421 Arthropoda Species 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 241001465754 Metazoa Species 0.000 claims description 26
- 244000000013 helminth Species 0.000 claims description 18
- 241000244206 Nematoda Species 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 14
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
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- 208000015181 infectious disease Diseases 0.000 claims description 6
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- 238000006467 substitution reaction Methods 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 238000006193 diazotization reaction Methods 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- SOKAMWBADQJOEJ-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-nitropyrazole Chemical compound C1=C([N+](=O)[O-])C=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl SOKAMWBADQJOEJ-UHFFFAOYSA-N 0.000 claims 1
- XORHNJQEWQGXCN-UHFFFAOYSA-N 4-nitro-1h-pyrazole Chemical compound [O-][N+](=O)C=1C=NNC=1 XORHNJQEWQGXCN-UHFFFAOYSA-N 0.000 claims 1
- IXYGWJMLYMKSPD-UHFFFAOYSA-N 5-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-nitro-1h-pyrazole Chemical compound C1=NNC(C=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)=C1[N+](=O)[O-] IXYGWJMLYMKSPD-UHFFFAOYSA-N 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- NAFOIZPSUNESOU-UHFFFAOYSA-N [B].[I] Chemical compound [B].[I] NAFOIZPSUNESOU-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- VIXSOWQURDXXGQ-UHFFFAOYSA-N n-[5-bromo-2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-nitropyrazol-3-yl]acetamide Chemical compound CC(=O)NC1=C([N+]([O-])=O)C(Br)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl VIXSOWQURDXXGQ-UHFFFAOYSA-N 0.000 claims 1
- 238000006396 nitration reaction Methods 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 7
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- 239000000243 solution Substances 0.000 description 25
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- JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N hydrofluoric acid Substances F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229960002358 iodine Drugs 0.000 description 1
- 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 1
- 230000006651 lactation Effects 0.000 description 1
- 229960002809 lindane Drugs 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- NUEUVZKABOBTKF-UHFFFAOYSA-N n-[5-cyano-2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-nitropyrazol-3-yl]acetamide Chemical compound CC(=O)NC1=C([N+]([O-])=O)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl NUEUVZKABOBTKF-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 238000009304 pastoral farming Methods 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 238000009372 pisciculture Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 210000001938 protoplast Anatomy 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- ZZIZZTHXZRDOFM-XFULWGLBSA-N tamsulosin hydrochloride Chemical compound [H+].[Cl-].CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 ZZIZZTHXZRDOFM-XFULWGLBSA-N 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- C07D231/16—Halogen atoms or nitro radicals
-
- 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
- C07D231/40—Acylated on said nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Epidemiology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878713769A GB8713769D0 (en) | 1987-06-12 | 1987-06-12 | Compositions of matter |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD272298A5 true DD272298A5 (de) | 1989-10-04 |
Family
ID=10618809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD88316724A DD272298A5 (de) | 1987-06-12 | 1988-06-13 | Verfahren zur herstellung von 4-nitro-n-phenylpyrazolderivaten und diese enthaltende zusammensetzungen |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0295118A1 (cs) |
| JP (1) | JP2746916B2 (cs) |
| KR (1) | KR960012171B1 (cs) |
| CN (1) | CN1018733B (cs) |
| AU (1) | AU619469B2 (cs) |
| BG (1) | BG49373A3 (cs) |
| BR (1) | BR8802937A (cs) |
| CA (1) | CA1330088C (cs) |
| CZ (1) | CZ282273B6 (cs) |
| DD (1) | DD272298A5 (cs) |
| DK (1) | DK314188A (cs) |
| EG (1) | EG19184A (cs) |
| FI (1) | FI882736A7 (cs) |
| GB (1) | GB8713769D0 (cs) |
| HU (1) | HU199426B (cs) |
| MA (1) | MA21293A1 (cs) |
| MY (1) | MY104850A (cs) |
| NO (1) | NO882552L (cs) |
| NZ (1) | NZ224978A (cs) |
| OA (1) | OA08741A (cs) |
| PH (1) | PH24138A (cs) |
| PL (1) | PL153477B1 (cs) |
| PT (1) | PT87698B (cs) |
| RO (2) | RO105758B1 (cs) |
| TR (1) | TR24894A (cs) |
| ZA (1) | ZA884180B (cs) |
| ZW (1) | ZW7488A1 (cs) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3355736B2 (ja) * | 1993-12-20 | 2002-12-09 | 住友化学工業株式会社 | 殺虫、殺ダニ剤組成物 |
| GB8713768D0 (en) * | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| AU655014B2 (en) * | 1991-04-30 | 1994-12-01 | Merial Limited | Pesticidal 1-aryl-5-(substituted alkylideneimino)-pyrazoles |
| US5236938A (en) * | 1991-04-30 | 1993-08-17 | Rhone-Poulenc Inc. | Pesticidal 1-aryl-5-(substituted alkylideneimino)pyrazoles |
| US5360910A (en) * | 1991-04-30 | 1994-11-01 | Rhone-Poulenc Ag Company | Pesticidal 1-aryl-5-(substituted alkylideneimino)pyrazoles |
| DE4234885A1 (de) * | 1992-10-16 | 1994-04-21 | Wella Ag | Verfahren zur Herstellung von 4,5-Diaminopyrazol-Derivaten, deren Verwendung zum Färben von Haaren sowie neue Pyrazol-Derivate |
| US5556873A (en) * | 1993-02-24 | 1996-09-17 | Rhone-Poulenc Inc. | Pesticidal 1-aryl-5-(substituted alkyl (thio) amido)pyrazoles |
| JP3715994B2 (ja) * | 1993-12-21 | 2005-11-16 | 住友化学株式会社 | 害虫防除剤 |
| US5814652A (en) * | 1995-12-20 | 1998-09-29 | Rhone-Poulenc Inc. | Pesticidal 5-amino-4-ethylsulfinyl-1-arylpyrazoles |
| TW524667B (en) * | 1996-12-05 | 2003-03-21 | Pfizer | Parasiticidal pyrazoles |
| EP1264823A1 (en) * | 2001-06-08 | 2002-12-11 | Novartis AG | Process for the preparation of 2,3-dicyanopropionates |
| US7514464B2 (en) | 2003-12-18 | 2009-04-07 | Pfizer Limited | Substituted arylpyrazoles |
| GB0329314D0 (en) | 2003-12-18 | 2004-01-21 | Pfizer Ltd | Substituted arylpyrazoles |
| CN100364979C (zh) * | 2006-02-28 | 2008-01-30 | 浙江大学 | 一种芳基吡唑菊酰胺类化合物及其用途 |
| CN102250008A (zh) * | 2010-05-17 | 2011-11-23 | 温州大学 | 5-氨基-3-氰基-4-乙硫基-1-(2,6-二氯-4-三氟甲基苯基)吡唑的制备方法 |
| CN106417329B (zh) * | 2016-09-27 | 2019-08-27 | 辽宁省蚕业科学研究所 | 一类柞蚕饰腹寄蝇病防治化合物及使用方法 |
| CN110452175A (zh) * | 2019-07-16 | 2019-11-15 | 河南衡谱分析检测技术有限公司 | 一种乙虫腈杂质的制备方法 |
| EP3766879A1 (en) * | 2019-07-19 | 2021-01-20 | Basf Se | Pesticidal pyrazole derivatives |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB580838A (en) * | 1944-08-15 | 1946-09-20 | Us Rubber Co | Improvements in method of making pneumatic tyres |
| US2608503A (en) * | 1950-09-16 | 1952-08-26 | Frank J Meyer | Method of making adhesive tapes and adhesive units |
| SE380196B (sv) * | 1974-08-15 | 1975-11-03 | Ziristor Ab | Sett att tillverka laminatbanor med fast kantremsa |
| FR2285990A1 (fr) * | 1974-09-24 | 1976-04-23 | Kleber Colombes | Procede de controle du calandrage d'un tissu metallique |
| JPS5827820B2 (ja) * | 1980-05-28 | 1983-06-11 | 横浜ゴム株式会社 | ゴム組成物 |
| DE3501323A1 (de) * | 1985-01-17 | 1986-07-17 | Bayer Ag, 5090 Leverkusen | 1-aryl-4-nitropyrazole |
| JPH0676387B2 (ja) * | 1985-10-01 | 1994-09-28 | 北興化学工業株式会社 | ピラゾ−ル誘導体および除草剤 |
| DE3540839A1 (de) * | 1985-11-18 | 1987-05-27 | Bayer Ag | 1-aryl-pyrazole |
| DE3543035A1 (de) * | 1985-12-05 | 1987-06-11 | Bayer Ag | 5-fluoracylamino-4-nitro-1-aryl-pyrazole |
| DE3617977A1 (de) * | 1985-12-05 | 1987-06-11 | Bayer Ag | 5-dichloracetamido-4-nitro-1-aryl-pyrazole |
| GB8531485D0 (en) * | 1985-12-20 | 1986-02-05 | May & Baker Ltd | Compositions of matter |
| GB8713768D0 (en) * | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| GB8816096D0 (en) * | 1988-07-06 | 1988-08-10 | May & Baker Ltd | New method & compositions of matter |
| JP2951699B2 (ja) * | 1990-07-18 | 1999-09-20 | 株式会社ブリヂストン | コード入りゴムシートの成形方法および装置 |
| JPH0720654B2 (ja) * | 1990-09-25 | 1995-03-08 | 住友ゴム工業株式会社 | ゴム付スチールコード材の製造方法およびその装置 |
| DE4205249C2 (de) * | 1992-02-21 | 1993-11-25 | Hans Hagner | Herstellungsverfahren für eine Verbundfolie |
| JPH0762000A (ja) * | 1993-08-24 | 1995-03-07 | Mitsui Toatsu Chem Inc | モノクローナル抗体 |
-
1987
- 1987-06-12 GB GB878713769A patent/GB8713769D0/en active Pending
-
1988
- 1988-06-03 MA MA21535A patent/MA21293A1/fr unknown
- 1988-06-09 PT PT87698A patent/PT87698B/pt not_active IP Right Cessation
- 1988-06-09 FI FI882736A patent/FI882736A7/fi not_active Application Discontinuation
- 1988-06-09 NO NO882552A patent/NO882552L/no unknown
- 1988-06-09 RO RO144039A patent/RO105758B1/ro unknown
- 1988-06-09 EG EG32388A patent/EG19184A/xx active
- 1988-06-09 RO RO1988133911A patent/RO100613B1/ro unknown
- 1988-06-09 ZW ZW74/88A patent/ZW7488A1/xx unknown
- 1988-06-09 MY MYPI88000633A patent/MY104850A/en unknown
- 1988-06-09 AU AU17553/88A patent/AU619469B2/en not_active Expired
- 1988-06-09 DK DK314188A patent/DK314188A/da unknown
- 1988-06-10 TR TR88/0408A patent/TR24894A/xx unknown
- 1988-06-10 PH PH37038A patent/PH24138A/en unknown
- 1988-06-10 PL PL1988272999A patent/PL153477B1/pl unknown
- 1988-06-10 NZ NZ224978A patent/NZ224978A/xx unknown
- 1988-06-10 EP EP88305307A patent/EP0295118A1/en not_active Withdrawn
- 1988-06-10 CA CA000569270A patent/CA1330088C/en not_active Expired - Lifetime
- 1988-06-10 HU HU883010A patent/HU199426B/hu unknown
- 1988-06-10 JP JP63143452A patent/JP2746916B2/ja not_active Expired - Lifetime
- 1988-06-10 ZA ZA884180A patent/ZA884180B/xx unknown
- 1988-06-10 BG BG084439A patent/BG49373A3/xx unknown
- 1988-06-10 OA OA59373A patent/OA08741A/xx unknown
- 1988-06-10 CZ CS884053A patent/CZ282273B6/cs not_active IP Right Cessation
- 1988-06-11 KR KR1019880007046A patent/KR960012171B1/ko not_active Expired - Lifetime
- 1988-06-11 CN CN88103589A patent/CN1018733B/zh not_active Expired
- 1988-06-13 DD DD88316724A patent/DD272298A5/de not_active IP Right Cessation
- 1988-06-13 BR BR8802937A patent/BR8802937A/pt not_active IP Right Cessation
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