DE3325488A1 - N-phenylpyrazolderivate und ihre verwendung als herbicide - Google Patents

Info

Publication number

DE3325488A1

DE3325488A1 DE19833325488 DE3325488A DE3325488A1 DE 3325488 A1 DE3325488 A1 DE 3325488A1 DE 19833325488 DE19833325488 DE 19833325488 DE 3325488 A DE3325488 A DE 3325488A DE 3325488 A1 DE3325488 A1 DE 3325488A1

Authority

DE

Germany

Prior art keywords

cyano

branched

straight

chain

group

Prior art date

1982-07-15

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Withdrawn

Links

• Espacenet
• Global Dossier
• DPMA
• Discuss

• WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical class C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 title claims description 47
• 239000004009 herbicide Substances 0.000 title description 14
• 150000001875 compounds Chemical class 0.000 claims description 298
• -1 η-butyl Chemical group 0.000 claims description 240
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 210
• 239000000203 mixture Substances 0.000 claims description 177
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 131
• 229910052799 carbon Inorganic materials 0.000 claims description 120
• 239000007787 solid Substances 0.000 claims description 112
• 238000000034 method Methods 0.000 claims description 97
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 96
• 229910052739 hydrogen Inorganic materials 0.000 claims description 80
• 239000001257 hydrogen Substances 0.000 claims description 80
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 75
• 239000011541 reaction mixture Substances 0.000 claims description 73
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 69
• 241000196324 Embryophyta Species 0.000 claims description 67
• 238000010992 reflux Methods 0.000 claims description 56
• 230000002363 herbicidal effect Effects 0.000 claims description 51
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 50
• 238000006243 chemical reaction Methods 0.000 claims description 50
• 230000012010 growth Effects 0.000 claims description 48
• 239000003960 organic solvent Substances 0.000 claims description 42
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 38
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
• 229910052801 chlorine Inorganic materials 0.000 claims description 34
• 239000007788 liquid Substances 0.000 claims description 34
• 125000000217 alkyl group Chemical group 0.000 claims description 31
• 239000000460 chlorine Substances 0.000 claims description 31
• 239000004563 wettable powder Substances 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 27
• 125000003545 alkoxy group Chemical group 0.000 claims description 26
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 25
• 229910052783 alkali metal Inorganic materials 0.000 claims description 25
• 230000009467 reduction Effects 0.000 claims description 25
• 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 claims description 24
• 239000002585 base Substances 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 23
• 239000004480 active ingredient Substances 0.000 claims description 22
• 239000008187 granular material Substances 0.000 claims description 22
• 230000008569 process Effects 0.000 claims description 22
• 239000004094 surface-active agent Substances 0.000 claims description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
• 239000003085 diluting agent Substances 0.000 claims description 21
• 239000011737 fluorine Substances 0.000 claims description 21
• 229910052731 fluorine Inorganic materials 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 239000000843 powder Substances 0.000 claims description 21
• 239000011734 sodium Substances 0.000 claims description 21
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
• 229910052794 bromium Inorganic materials 0.000 claims description 20
• 125000005843 halogen group Chemical group 0.000 claims description 20
• 238000002360 preparation method Methods 0.000 claims description 20
• 229910052708 sodium Inorganic materials 0.000 claims description 20
• 239000002904 solvent Substances 0.000 claims description 20
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
• 239000012141 concentrate Substances 0.000 claims description 18
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
• 235000021307 Triticum Nutrition 0.000 claims description 17
• 239000002253 acid Substances 0.000 claims description 17
• 150000002431 hydrogen Chemical class 0.000 claims description 17
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
• 125000000304 alkynyl group Chemical group 0.000 claims description 14
• 125000003277 amino group Chemical group 0.000 claims description 13
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
• 125000005265 dialkylamine group Chemical group 0.000 claims description 13
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 11
• 239000000969 carrier Substances 0.000 claims description 11
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
• 150000001340 alkali metals Chemical class 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 239000004550 soluble concentrate Substances 0.000 claims description 10
• 239000004546 suspension concentrate Substances 0.000 claims description 10
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 9
• 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 claims description 9
• 235000011181 potassium carbonates Nutrition 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 8
• 239000007900 aqueous suspension Substances 0.000 claims description 8
• 239000004495 emulsifiable concentrate Substances 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 229910000104 sodium hydride Inorganic materials 0.000 claims description 8
• 239000002562 thickening agent Substances 0.000 claims description 8
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 239000012312 sodium hydride Substances 0.000 claims description 7
• 238000005809 transesterification reaction Methods 0.000 claims description 7
• RSZTXMFLJHICPH-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(propylamino)pyrazole-4-carbonitrile Chemical compound CCCNC1=C(C#N)C=NN1C1=CC=C(Cl)C=C1Cl RSZTXMFLJHICPH-UHFFFAOYSA-N 0.000 claims description 6
• QCSVQOBDDQLEHF-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(2-oxoazetidin-1-yl)pyrazole-4-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(N2C(CC2)=O)=C(C#N)C=N1 QCSVQOBDDQLEHF-UHFFFAOYSA-N 0.000 claims description 6
• NBMYPTDTCKYLCA-UHFFFAOYSA-N 5-(butylamino)-1-[2-chloro-4-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile Chemical compound CCCCNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl NBMYPTDTCKYLCA-UHFFFAOYSA-N 0.000 claims description 6
• 229910021529 ammonia Inorganic materials 0.000 claims description 6
• 235000013339 cereals Nutrition 0.000 claims description 6
• 150000007522 mineralic acids Chemical class 0.000 claims description 6
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 239000012429 reaction media Substances 0.000 claims description 6
• 229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
• 239000012279 sodium borohydride Substances 0.000 claims description 6
• XRMWZSOKBCRUMR-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-5-(propylsulfanylamino)pyrazole-4-carbonitrile Chemical compound CCCSNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl XRMWZSOKBCRUMR-UHFFFAOYSA-N 0.000 claims description 5
• VOQYWIZPERVCCN-UHFFFAOYSA-N 3-amino-1-[2-chloro-4-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile Chemical compound NC1=NN(C=C1C#N)C1=C(C=C(C=C1)C(F)(F)F)Cl VOQYWIZPERVCCN-UHFFFAOYSA-N 0.000 claims description 5
• 125000000033 alkoxyamino group Chemical group 0.000 claims description 5
• 239000003795 chemical substances by application Substances 0.000 claims description 5
• 238000003776 cleavage reaction Methods 0.000 claims description 5
• 150000003983 crown ethers Chemical class 0.000 claims description 5
• 230000007017 scission Effects 0.000 claims description 5
• 239000000126 substance Substances 0.000 claims description 5
• JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims description 4
• JBNRMAHIYIJINZ-UHFFFAOYSA-N 2-[[2-[2-chloro-4-(trifluoromethyl)phenyl]-4-cyanopyrazol-3-yl]amino]acetic acid Chemical compound OC(=O)CNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl JBNRMAHIYIJINZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 240000005979 Hordeum vulgare Species 0.000 claims description 4
• 235000007340 Hordeum vulgare Nutrition 0.000 claims description 4
• 240000007594 Oryza sativa Species 0.000 claims description 4
• 235000007164 Oryza sativa Nutrition 0.000 claims description 4
• 230000002378 acidificating effect Effects 0.000 claims description 4
• 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
• 125000005091 alkenylcarbonylamino group Chemical group 0.000 claims description 4
• 239000011230 binding agent Substances 0.000 claims description 4
• 230000006378 damage Effects 0.000 claims description 4
• 230000032050 esterification Effects 0.000 claims description 4
• 238000005886 esterification reaction Methods 0.000 claims description 4
• 230000007062 hydrolysis Effects 0.000 claims description 4
• 238000006460 hydrolysis reaction Methods 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
• 239000011736 potassium bicarbonate Substances 0.000 claims description 4
• 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 4
• 235000015497 potassium bicarbonate Nutrition 0.000 claims description 4
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 4
• 229940086066 potassium hydrogencarbonate Drugs 0.000 claims description 4
• 235000009566 rice Nutrition 0.000 claims description 4
• 229920006395 saturated elastomer Polymers 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• IJYFWJVSLANPSK-UHFFFAOYSA-N 1-(2,3,4-trichlorophenyl)pyrazol-3-amine Chemical compound NC1=NN(C=C1)C1=C(C(=C(C=C1)Cl)Cl)Cl IJYFWJVSLANPSK-UHFFFAOYSA-N 0.000 claims description 3
• WXPNQEITSSNOQB-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(ethylamino)pyrazole-4-carbonitrile Chemical compound CCNC1=C(C#N)C=NN1C1=CC=C(Cl)C=C1Cl WXPNQEITSSNOQB-UHFFFAOYSA-N 0.000 claims description 3
• HQUHEMFIVQTAEV-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(methylamino)pyrazole-4-carbonitrile Chemical compound CNC1=C(C#N)C=NN1C1=CC=C(Cl)C=C1Cl HQUHEMFIVQTAEV-UHFFFAOYSA-N 0.000 claims description 3
• QLZISLDKIPTNQK-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(ethylsulfanylamino)pyrazole-4-carbonitrile Chemical compound CCSNC1=C(C#N)C=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl QLZISLDKIPTNQK-UHFFFAOYSA-N 0.000 claims description 3
• ASAHPNAHZONROW-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-5-(ethylsulfanylamino)pyrazole-4-carbonitrile Chemical compound CCSNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl ASAHPNAHZONROW-UHFFFAOYSA-N 0.000 claims description 3
• IZMVYNMGLATHJO-UHFFFAOYSA-N 2-[[2-[2-chloro-4-(trifluoromethyl)phenyl]-4-cyanopyrazol-3-yl]amino]-n-methoxyacetamide Chemical compound CONC(=O)CNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl IZMVYNMGLATHJO-UHFFFAOYSA-N 0.000 claims description 3
• HJKXSWMBWNSDJQ-UHFFFAOYSA-N 2-[[4-cyano-2-(2,4,6-trichlorophenyl)pyrazol-3-yl]amino]acetic acid Chemical compound OC(=O)CNC1=C(C#N)C=NN1C1=C(Cl)C=C(Cl)C=C1Cl HJKXSWMBWNSDJQ-UHFFFAOYSA-N 0.000 claims description 3
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 3
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
• QLMJEVXDRZZGQX-UHFFFAOYSA-N 3-amino-5-(2-hydroxyethyl)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound C(#N)C=1C(=NN(C=1CCO)C1=C(C(=C(C=C1)Cl)Cl)Cl)N QLMJEVXDRZZGQX-UHFFFAOYSA-N 0.000 claims description 3
• ZWQRFSFJEKWYDG-UHFFFAOYSA-N 3-amino-5-prop-2-enyl-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound C(#N)C=1C(=NN(C=1CC=C)C1=C(C(=C(C=C1)Cl)Cl)Cl)N ZWQRFSFJEKWYDG-UHFFFAOYSA-N 0.000 claims description 3
• PLIAITMRGNSLTO-UHFFFAOYSA-N 4-propyl-1h-pyrazol-5-amine Chemical compound CCCC=1C=NNC=1N PLIAITMRGNSLTO-UHFFFAOYSA-N 0.000 claims description 3
• CFWGZEMVPJRPLM-UHFFFAOYSA-N 5-(butylamino)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound CCCCNC1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl CFWGZEMVPJRPLM-UHFFFAOYSA-N 0.000 claims description 3
• WBFOPGXLTOPXOW-UHFFFAOYSA-N 5-amino-2-(2-chloro-4-ethylphenyl)-3-(ethoxymethylidene)-1H-pyrazole-4-carbonitrile Chemical compound ClC1=C(C=CC(=C1)CC)N1NC(=C(C1=COCC)C#N)N WBFOPGXLTOPXOW-UHFFFAOYSA-N 0.000 claims description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
• 241000209504 Poaceae Species 0.000 claims description 3
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
• 240000008042 Zea mays Species 0.000 claims description 3
• 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 3
• 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 3
• 150000008041 alkali metal carbonates Chemical class 0.000 claims description 3
• 239000007864 aqueous solution Substances 0.000 claims description 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
• 229910052740 iodine Chemical group 0.000 claims description 3
• JOJWQEQWJHWBAG-UHFFFAOYSA-N n-butyl-2-[[2-[2-chloro-4-(trifluoromethyl)phenyl]-4-cyanopyrazol-3-yl]amino]acetamide Chemical compound CCCCNC(=O)CNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl JOJWQEQWJHWBAG-UHFFFAOYSA-N 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• SPOSAXFNVLKYBU-UHFFFAOYSA-N 1-(4-ethyl-2,3,5,6-tetrafluorophenyl)-5-(methylamino)pyrazole-4-carbonitrile Chemical compound FC1=C(F)C(CC)=C(F)C(F)=C1N1C(NC)=C(C#N)C=N1 SPOSAXFNVLKYBU-UHFFFAOYSA-N 0.000 claims description 2
• DOXOIXKPGLKLCB-UHFFFAOYSA-N 1-[2,6-dibromo-4-(trifluoromethyl)phenyl]-5-(methylamino)pyrazole-4-carbonitrile Chemical compound CNC1=C(C#N)C=NN1C1=C(Br)C=C(C(F)(F)F)C=C1Br DOXOIXKPGLKLCB-UHFFFAOYSA-N 0.000 claims description 2
• UUSUPPWMXHZANT-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-5-(2-oxopyrrolidin-1-yl)pyrazole-4-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC=C1N1C(N2C(CCC2)=O)=C(C#N)C=N1 UUSUPPWMXHZANT-UHFFFAOYSA-N 0.000 claims description 2
• YIIGYHZOBUKFHQ-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-5-(methylamino)pyrazole-4-carbonitrile Chemical compound CNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl YIIGYHZOBUKFHQ-UHFFFAOYSA-N 0.000 claims description 2
• OKLLDRLOEWORBR-UHFFFAOYSA-N 2-[[2-[2-chloro-4-(trifluoromethyl)phenyl]-4-cyanopyrazol-3-yl]amino]-n-pentylacetamide Chemical compound CCCCCNC(=O)CNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl OKLLDRLOEWORBR-UHFFFAOYSA-N 0.000 claims description 2
• KZDRRQNIKWNLLC-UHFFFAOYSA-N 2-[[2-[2-chloro-4-(trifluoromethyl)phenyl]-4-cyanopyrazol-3-yl]amino]acetamide Chemical compound NC(=O)CNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl KZDRRQNIKWNLLC-UHFFFAOYSA-N 0.000 claims description 2
• YNNPZDGZXNSWFB-UHFFFAOYSA-N 2-[[4-cyano-2-(4-ethyl-2,3,5,6-tetrafluorophenyl)pyrazol-3-yl]amino]acetic acid Chemical compound FC1=C(F)C(CC)=C(F)C(F)=C1N1C(NCC(O)=O)=C(C#N)C=N1 YNNPZDGZXNSWFB-UHFFFAOYSA-N 0.000 claims description 2
• WAPPRYDZJHBZFW-UHFFFAOYSA-N 3-[5-amino-4-cyano-2-(2,3,4-trichlorophenyl)pyrazol-3-yl]butanoic acid Chemical compound C(=O)(O)CC(C)C1=C(C(=NN1C1=C(C(=C(C=C1)Cl)Cl)Cl)N)C#N WAPPRYDZJHBZFW-UHFFFAOYSA-N 0.000 claims description 2
• VSBDPUVNMPMTBJ-UHFFFAOYSA-N 3-[5-amino-4-cyano-2-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazol-3-yl]propanoic acid Chemical compound C(=O)(O)CCC1=C(C(=NN1C1=C(C=C(C=C1Cl)C(F)(F)F)Cl)N)C#N VSBDPUVNMPMTBJ-UHFFFAOYSA-N 0.000 claims description 2
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
• WRCVYQKZMYWDSR-UHFFFAOYSA-N 5-(2,3,4,6-tetrafluorophenyl)-1H-pyrazole Chemical compound FC1=C(C(=CC(=C1F)F)F)C1=NNC=C1 WRCVYQKZMYWDSR-UHFFFAOYSA-N 0.000 claims description 2
• GEIKPCICYHFYNF-UHFFFAOYSA-N 5-(2-hexyl-4-oxoazetidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound CCCCCCC1CC(=O)N1C1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl GEIKPCICYHFYNF-UHFFFAOYSA-N 0.000 claims description 2
• ACGMOGRCWHSBRQ-UHFFFAOYSA-N 5-(butylsulfanylamino)-1-[2-chloro-4-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile Chemical compound CCCCSNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl ACGMOGRCWHSBRQ-UHFFFAOYSA-N 0.000 claims description 2
• NXVJEFCCCYIMTH-UHFFFAOYSA-N 5-(ethylsulfanylamino)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound CCSNC1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl NXVJEFCCCYIMTH-UHFFFAOYSA-N 0.000 claims description 2
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