TWI317357B - Pyrazolylcarboxanilides - Google Patents

Info

Publication number

TWI317357B

TWI317357B TW091116416A TW91116416A TWI317357B TW I317357 B TWI317357 B TW I317357B TW 091116416 A TW091116416 A TW 091116416A TW 91116416 A TW91116416 A TW 91116416A TW I317357 B TWI317357 B TW I317357B

Authority

TW

Taiwan

Prior art keywords

formula

patent application

group

alkyl

cns

Prior art date

2001-07-25

Links

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• -1 (1) Pyrazolyl Carboxylaniline Chemical compound 0.000 claims description 121
• 150000001875 compounds Chemical class 0.000 claims description 99
• 238000000034 method Methods 0.000 claims description 87
• 125000001424 substituent group Chemical group 0.000 claims description 70
• 230000008569 process Effects 0.000 claims description 43
• 229910052736 halogen Inorganic materials 0.000 claims description 36
• 150000002367 halogens Chemical class 0.000 claims description 35
• 239000000203 mixture Substances 0.000 claims description 33
• 239000002253 acid Substances 0.000 claims description 32
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 24
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 24
• 239000011737 fluorine Substances 0.000 claims description 24
• 229910052731 fluorine Inorganic materials 0.000 claims description 24
• 239000000123 paper Substances 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 239000003085 diluting agent Substances 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 230000002079 cooperative effect Effects 0.000 claims description 17
• 238000002360 preparation method Methods 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
• 241000233866 Fungi Species 0.000 claims description 14
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
• 229910052794 bromium Inorganic materials 0.000 claims description 14
• 239000003054 catalyst Substances 0.000 claims description 14
• 238000006243 chemical reaction Methods 0.000 claims description 14
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 239000000460 chlorine Substances 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 239000011230 binding agent Substances 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 150000002431 hydrogen Chemical group 0.000 claims description 8
• 150000002576 ketones Chemical class 0.000 claims description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 239000003795 chemical substances by application Substances 0.000 claims description 6
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000004432 carbon atom Chemical group C* 0.000 claims description 5
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 150000001448 anilines Chemical class 0.000 claims description 4
• 230000001276 controlling effect Effects 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 229920002554 vinyl polymer Polymers 0.000 claims description 4
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
• 150000001336 alkenes Chemical class 0.000 claims description 3
• 150000001345 alkine derivatives Chemical class 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
• 229910052740 iodine Inorganic materials 0.000 claims description 3
• 239000011630 iodine Substances 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 229910052698 phosphorus Inorganic materials 0.000 claims description 3
• 239000011574 phosphorus Substances 0.000 claims description 3
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
• 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000006038 hexenyl group Chemical group 0.000 claims description 2
• NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 claims description 2
• 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 claims description 2
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
• 239000004094 surface-active agent Substances 0.000 claims description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
• 150000003931 anilides Chemical class 0.000 claims 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 1
• 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 1
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 1
• 239000004067 bulking agent Substances 0.000 claims 1
• GABQKHQNXWNJJJ-UHFFFAOYSA-N diphenylcarbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)C1=CC=CC=C1 GABQKHQNXWNJJJ-UHFFFAOYSA-N 0.000 claims 1
• 241000196324 Embryophyta Species 0.000 description 68
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 49
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• 239000007789 gas Substances 0.000 description 27
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 26
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 26
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
• 239000007858 starting material Substances 0.000 description 21
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
• 239000002585 base Substances 0.000 description 18
• 235000019439 ethyl acetate Nutrition 0.000 description 17
• 238000012360 testing method Methods 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• 241000894007 species Species 0.000 description 14
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 238000009472 formulation Methods 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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• 244000299507 Gossypium hirsutum Species 0.000 description 8
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
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• NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 8
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