CA1053231A - Amides et thioamides a groupe pyrazole - Google Patents

Amides et thioamides a groupe pyrazole

Info

Publication number: CA1053231A
Authority: CA; Canada
Prior art keywords: alpha; acetamide; compound according; phenylpyrazole; methyl
Prior art date: 1974-11-15
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.): Expired

Application number

CA240,263A

Other languages

English (en)

Other versions

CA240263S (en

Inventor

Malcolm W. Moon

Gabriel Kornis

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.)

Pharmacia and Upjohn Co

Original Assignee

Upjohn Co

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.)

1974-11-15

Filing date

1975-11-24

Publication date

1979-04-24

1975-11-24 Application filed by Upjohn Co filed Critical Upjohn Co

1976-05-14 Priority claimed from US05/686,548 external-priority patent/US4072498A/en

1979-04-24 Application granted granted Critical

1979-04-24 Publication of CA1053231A publication Critical patent/CA1053231A/fr

Status Expired legal-status Critical Current

Links

-1 Pyrazole amides Chemical class 0.000 title claims abstract description 51
150000003556 thioamides Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 213
238000000034 method Methods 0.000 claims abstract description 176
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 38
125000000217 alkyl group Chemical group 0.000 claims abstract description 29
229910052736 halogen Inorganic materials 0.000 claims abstract description 24
150000002367 halogens Chemical class 0.000 claims abstract description 24
239000002253 acid Substances 0.000 claims abstract description 21
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 18
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
150000002431 hydrogen Chemical group 0.000 claims abstract description 12
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
239000011593 sulfur Substances 0.000 claims abstract description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
239000001301 oxygen Substances 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 6
229910052757 nitrogen Inorganic materials 0.000 claims description 118
229940080818 propionamide Drugs 0.000 claims description 43
241000196324 Embryophyta Species 0.000 claims description 19
SQTLUXJWUCHKMT-UHFFFAOYSA-N 4-bromo-n,n-diphenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 SQTLUXJWUCHKMT-UHFFFAOYSA-N 0.000 claims description 12
229960001413 acetanilide Drugs 0.000 claims description 10
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
QUQMINHLKOJCAX-UHFFFAOYSA-N n,n-dimethyl-1-(4-methyl-3-phenylpyrazol-1-yl)cyclopentane-1-carboxamide Chemical compound C1=C(C)C(C=2C=CC=CC=2)=NN1C1(C(=O)N(C)C)CCCC1 QUQMINHLKOJCAX-UHFFFAOYSA-N 0.000 claims description 2
GFHJEPAAHDPDSO-UHFFFAOYSA-N n,n-dimethyl-1-(4-methyl-3-phenylpyrazol-1-yl)cyclopropane-1-carboxamide Chemical compound C1=C(C)C(C=2C=CC=CC=2)=NN1C1(C(=O)N(C)C)CC1 GFHJEPAAHDPDSO-UHFFFAOYSA-N 0.000 claims description 2
REWWXQMGMLLOEX-UHFFFAOYSA-N n,n-dimethyl-3-(3-phenylpyrazol-1-yl)propanamide Chemical compound CN(C)C(=O)CCN1C=CC(C=2C=CC=CC=2)=N1 REWWXQMGMLLOEX-UHFFFAOYSA-N 0.000 claims description 2
DGNAEGZUMWWIFZ-UHFFFAOYSA-N 2-(4-methyl-3-phenylpyrazol-1-yl)-1-morpholin-4-ylpropan-1-one Chemical compound C1=C(C)C(C=2C=CC=CC=2)=NN1C(C)C(=O)N1CCOCC1 DGNAEGZUMWWIFZ-UHFFFAOYSA-N 0.000 claims 1
WLQASZIGULYJIN-UHFFFAOYSA-N 2-(4-methyl-3-phenylpyrazol-1-yl)-1-pyrrolidin-1-ylpropan-1-one Chemical compound C1=C(C)C(C=2C=CC=CC=2)=NN1C(C)C(=O)N1CCCC1 WLQASZIGULYJIN-UHFFFAOYSA-N 0.000 claims 1
LSDCNPNLIOHJIN-UHFFFAOYSA-N n,n-dimethyl-1-(3-phenylpyrazol-1-yl)cyclobutane-1-carboxamide Chemical compound C1=CC(C=2C=CC=CC=2)=NN1C1(C(=O)N(C)C)CCC1 LSDCNPNLIOHJIN-UHFFFAOYSA-N 0.000 claims 1
CKJAPFZGEUEQKK-UHFFFAOYSA-N n,n-dimethyl-1-(3-phenylpyrazol-1-yl)cyclopropane-1-carboxamide Chemical compound C1=CC(C=2C=CC=CC=2)=NN1C1(C(=O)N(C)C)CC1 CKJAPFZGEUEQKK-UHFFFAOYSA-N 0.000 claims 1
KAFYPRSELFFKFX-UHFFFAOYSA-N n,n-dimethyl-1-(4-methyl-3-phenylpyrazol-1-yl)cyclobutane-1-carboxamide Chemical compound C1=C(C)C(C=2C=CC=CC=2)=NN1C1(C(=O)N(C)C)CCC1 KAFYPRSELFFKFX-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 45
239000002689 soil Substances 0.000 abstract description 5
239000000969 carrier Substances 0.000 abstract description 3
238000002844 melting Methods 0.000 description 122
230000008018 melting Effects 0.000 description 122
239000000460 chlorine Substances 0.000 description 87
238000004458 analytical method Methods 0.000 description 75
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 74
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 47
LANBPXHLIUYXOT-UHFFFAOYSA-N 4-methyl-5-phenyl-1h-pyrazole Chemical compound C1=NNC(C=2C=CC=CC=2)=C1C LANBPXHLIUYXOT-UHFFFAOYSA-N 0.000 description 46
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 45
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 33
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 28
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 25
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical group [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 22
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 21
239000002904 solvent Substances 0.000 description 21
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 20
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 20
229910052794 bromium Inorganic materials 0.000 description 20
238000009835 boiling Methods 0.000 description 19
238000009472 formulation Methods 0.000 description 19
239000003921 oil Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000007792 addition Methods 0.000 description 18
235000019198 oils Nutrition 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
WDOAUKIEENWZNC-UHFFFAOYSA-N 2-chloro-n,n-dimethylpropanamide Chemical compound CC(Cl)C(=O)N(C)C WDOAUKIEENWZNC-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
239000004480 active ingredient Substances 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 15
150000001408 amides Chemical class 0.000 description 14
239000007788 liquid Substances 0.000 description 14
239000007921 spray Substances 0.000 description 14
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 9
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 9
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000002363 herbicidal effect Effects 0.000 description 8
239000002245 particle Substances 0.000 description 8
239000004094 surface-active agent Substances 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
239000008096 xylene Substances 0.000 description 8
NNWWOIPEHSLORU-UHFFFAOYSA-N 2-bromo-n,n-dimethylbutanamide Chemical compound CCC(Br)C(=O)N(C)C NNWWOIPEHSLORU-UHFFFAOYSA-N 0.000 description 7
PTGHHGHHFPDNBR-UHFFFAOYSA-N 2-pyrazol-1-ylacetamide Chemical compound NC(=O)CN1C=CC=N1 PTGHHGHHFPDNBR-UHFFFAOYSA-N 0.000 description 7
OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
229950005499 carbon tetrachloride Drugs 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
239000000839 emulsion Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
238000002156 mixing Methods 0.000 description 7
239000000843 powder Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000011734 sodium Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
239000007787 solid Substances 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000002877 alkyl aryl group Chemical group 0.000 description 6
239000000538 analytical sample Substances 0.000 description 6
239000011575 calcium Substances 0.000 description 6
239000007810 chemical reaction solvent Substances 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
235000008504 concentrate Nutrition 0.000 description 6
238000007796 conventional method Methods 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000000428 dust Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
229910052791 calcium Inorganic materials 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 5
239000012071 phase Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
159000000000 sodium salts Chemical class 0.000 description 5
239000010455 vermiculite Substances 0.000 description 5
229910052902 vermiculite Inorganic materials 0.000 description 5
235000019354 vermiculite Nutrition 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000004927 clay Substances 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
238000010828 elution Methods 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
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 4
238000003786 synthesis reaction Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 4
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 4
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 3
HPGOCRQDLWEAOQ-UHFFFAOYSA-N 2-(3-methylpyrazol-1-yl)acetamide Chemical compound CC=1C=CN(CC(N)=O)N=1 HPGOCRQDLWEAOQ-UHFFFAOYSA-N 0.000 description 3
GXSNDPGJEZZSAK-UHFFFAOYSA-N 2-(3-phenylpyrazol-1-yl)acetamide Chemical compound NC(=O)CN1C=CC(C=2C=CC=CC=2)=N1 GXSNDPGJEZZSAK-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CNUHUXQSZVLAGL-UHFFFAOYSA-N 2-bromo-n,n,2-trimethylpropanamide Chemical compound CN(C)C(=O)C(C)(C)Br CNUHUXQSZVLAGL-UHFFFAOYSA-N 0.000 description 3
GFMLTSYQNSICHT-UHFFFAOYSA-N 4-methyl-5-(2-methylphenyl)-1h-pyrazole Chemical group C1=NNC(C=2C(=CC=CC=2)C)=C1C GFMLTSYQNSICHT-UHFFFAOYSA-N 0.000 description 3
GRKIAPNDYIKCBO-UHFFFAOYSA-N 5-(2-chlorophenyl)-4-methyl-1h-pyrazole Chemical compound C1=NNC(C=2C(=CC=CC=2)Cl)=C1C GRKIAPNDYIKCBO-UHFFFAOYSA-N 0.000 description 3
QQYICHGCQZYYOQ-UHFFFAOYSA-N 5-(furan-2-yl)-4-methyl-1h-pyrazole Chemical group C1=NNC(C=2OC=CC=2)=C1C QQYICHGCQZYYOQ-UHFFFAOYSA-N 0.000 description 3
QHRSESMSOJZMCO-UHFFFAOYSA-N 5-methyl-3-phenyl-1h-pyrazole Chemical group N1C(C)=CC(C=2C=CC=CC=2)=N1 QHRSESMSOJZMCO-UHFFFAOYSA-N 0.000 description 3
101150041968 CDC13 gene Proteins 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000000068 chlorophenyl group Chemical group 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 3
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ASCCMGGNOJXQPO-UHFFFAOYSA-N n,n-dimethyl-2-(4-methylpyrazol-1-yl)acetamide Chemical compound CN(C)C(=O)CN1C=C(C)C=N1 ASCCMGGNOJXQPO-UHFFFAOYSA-N 0.000 description 1
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SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
SEGJNMCIMOLEDM-UHFFFAOYSA-N n-methyloctan-1-amine Chemical group CCCCCCCCNC SEGJNMCIMOLEDM-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
231100001184 nonphytotoxic Toxicity 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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 description 1
229940099990 ogen Drugs 0.000 description 1
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125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
230000008121 plant development Effects 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
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239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229940088417 precipitated calcium carbonate Drugs 0.000 description 1
125000006308 propyl amino group Chemical group 0.000 description 1
238000010298 pulverizing process Methods 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
239000010453 quartz Substances 0.000 description 1
230000036647 reaction Effects 0.000 description 1
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239000011435 rock Substances 0.000 description 1
102220044643 rs587781450 Human genes 0.000 description 1
XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
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BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA240,263A 1974-11-15 1975-11-24 Amides et thioamides a groupe pyrazole Expired CA1053231A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US52423174A	1974-11-15	1974-11-15
US05/686,548 US4072498A (en)	1974-11-15	1976-05-14	Pyrazole amides

Publications (1)

Publication Number	Publication Date
CA1053231A true CA1053231A (fr)	1979-04-24

Family

ID=27061423

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA240,263A Expired CA1053231A (fr)	1974-11-15	1975-11-24	Amides et thioamides a groupe pyrazole

Country Status (2)

Country	Link
CA (1)	CA1053231A (fr)
PH (1)	PH14320A (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5281571A (en) *	1990-10-18	1994-01-25	Monsanto Company	Herbicidal benzoxazinone- and benzothiazinone-substituted pyrazoles
CN103772283A (zh) *	2014-01-17	2014-05-07	怀化学院	一类含芳环及二卤取代的吡唑化合物及其制备方法和用途
WO2019081485A1 (fr)	2017-10-26	2019-05-02	Bayer Cropscience Aktiengesellschaft	Pyrazoles substitués, leurs sels et leur utilisation comme agents herbicides
WO2019081477A1 (fr)	2017-10-26	2019-05-02	Bayer Cropscience Aktiengesellschaft	Pyrazoles substitués, leurs sels et leur utilisation comme agents herbicides
EP3858811A4 (fr) *	2018-09-28	2022-05-11	Shenzhen EDK Pharmaceutical Technology Co., Ltd.	Composé amide n-aromatique et son procédé de préparation et utilisation associée

1975
- 1975-11-24 CA CA240,263A patent/CA1053231A/fr not_active Expired
1977
- 1977-11-23 PH PH20470A patent/PH14320A/en unknown

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5281571A (en) *	1990-10-18	1994-01-25	Monsanto Company	Herbicidal benzoxazinone- and benzothiazinone-substituted pyrazoles
US5489571A (en) *	1990-10-18	1996-02-06	Monsanto Company	Herbicidal substituted aryl-haloalkylpyrazoles
CN103772283A (zh) *	2014-01-17	2014-05-07	怀化学院	一类含芳环及二卤取代的吡唑化合物及其制备方法和用途
WO2019081485A1 (fr)	2017-10-26	2019-05-02	Bayer Cropscience Aktiengesellschaft	Pyrazoles substitués, leurs sels et leur utilisation comme agents herbicides
WO2019081477A1 (fr)	2017-10-26	2019-05-02	Bayer Cropscience Aktiengesellschaft	Pyrazoles substitués, leurs sels et leur utilisation comme agents herbicides
EP3858811A4 (fr) *	2018-09-28	2022-05-11	Shenzhen EDK Pharmaceutical Technology Co., Ltd.	Composé amide n-aromatique et son procédé de préparation et utilisation associée
US11760727B2 (en)	2018-09-28	2023-09-19	Shenzhen Edk Pharmaceutical Technology Co., Ltd.	N-aromatic amide compounds, preparation methods and uses thereof

Also Published As

Publication number	Publication date
PH14320A (en)	1981-05-27

Publication	Publication Date	Title
US4072498A (en)	1978-02-07	Pyrazole amides
DE69835653T2 (de)	2007-09-20	Phthalsaeurediamidderivate, insektizide für landbau und gartenbau, und deren verwendung
AU729776B2 (en)	2001-02-08	Phthalamide derivatives, or salt thereof agrohorticultural insecticide, and method for using the same
DE60032483T2 (de)	2007-04-19	Diamid-derivate von heterocyclischen dicarbonsäuren, insektizide für acker- und gartenbau und ein verfahren zu ihrer verwendung
US5240951A (en)	1993-08-31	Isothiazolecarboxylic acid derivatives, rice blast control agents containing the same as active ingredients, and rice blast control method applying the control agents
US4182624A (en)	1980-01-08	Imidazole carboxylic acids and derivatives thereof
DE3904931A1 (de)	1990-08-23	Pyridyl-substituierte acrylsaeureester
HU204513B (en)	1992-01-28	Process for producing pyrazol derivatives and herbicide compositions containing them
DE69322118T2 (de)	1999-05-20	Amino-Thiazolderivate und ihre Anwendung als Fungizide
US5104886A (en)	1992-04-14	Amide derivatives, processes for production thereof, and agricultural-horticultural fungicide containing them
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