UA113513C2

UA113513C2 - N-(3-карбамоїлфеніл)-1h-піразол-5-карбоксамідні похідні і їх застосування для боротьби з тваринами-шкідниками

N-(3-карбамоїлфеніл)-1h-піразол-5-карбоксамідні похідні і їх застосування для боротьби з тваринами-шкідниками Download PDF

Info

Publication number: UA113513C2
Authority: UA; Ukraine
Prior art keywords: methyl; propyl; plants; alkyl; compounds
Prior art date: 2011-03-18

Application number

UAA201312076A

Other languages

English (en)

Ukrainian (uk)

Priority date

2011-03-18

Filing date

2012-03-12

Publication date

2017-02-10

2012-03-12 Application filed filed Critical

2012-03-12 Priority claimed from PCT/EP2012/054299 external-priority patent/WO2012126766A1/de

2017-02-10 Publication of UA113513C2 publication Critical patent/UA113513C2/uk

Links

241000607479 Yersinia pestis Species 0.000 title claims abstract description 37
241001465754 Metazoa Species 0.000 title claims description 34
OYCLGXBIXZFRJH-UHFFFAOYSA-N N-(3-carbamoylphenyl)-1H-pyrazole-5-carboxamide Chemical class NC(=O)c1cccc(NC(=O)c2ccn[nH]2)c1 OYCLGXBIXZFRJH-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 265
238000000034 method Methods 0.000 claims abstract description 66
-1 isopropylcarbonyl Chemical group 0.000 claims description 340
239000000203 mixture Substances 0.000 claims description 78
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 69
229910052739 hydrogen Inorganic materials 0.000 claims description 45
239000001257 hydrogen Substances 0.000 claims description 45
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
150000002431 hydrogen Chemical class 0.000 claims description 31
229910052736 halogen Inorganic materials 0.000 claims description 29
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
239000000460 chlorine Substances 0.000 claims description 26
229910052801 chlorine Inorganic materials 0.000 claims description 26
150000002367 halogens Chemical class 0.000 claims description 26
241000238631 Hexapoda Species 0.000 claims description 25
230000000694 effects Effects 0.000 claims description 25
125000004093 cyano group Chemical group *C#N 0.000 claims description 23
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
229910052731 fluorine Inorganic materials 0.000 claims description 20
239000011737 fluorine Substances 0.000 claims description 20
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
229910052794 bromium Inorganic materials 0.000 claims description 19
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
125000003636 chemical group Chemical group 0.000 claims description 12
239000000463 material Substances 0.000 claims description 10
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 10
125000006420 1-fluorocyclopropyl group Chemical group [H]C1([H])C([H])([H])C1(F)* 0.000 claims description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
244000045947 parasite Species 0.000 claims description 9
125000006426 1-chlorocyclopropyl group Chemical group [H]C1([H])C([H])([H])C1(Cl)* 0.000 claims description 8
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 7
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 7
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 7
125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims description 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
241000244206 Nematoda Species 0.000 claims description 6
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 6
125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
241000239223 Arachnida Species 0.000 claims description 4
239000011630 iodine Substances 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 claims description 3
238000009826 distribution Methods 0.000 claims description 3
239000013543 active substance Substances 0.000 claims description 2
239000000945 filler Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
229910052789 astatine Inorganic materials 0.000 claims 1
229940126601 medicinal product Drugs 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 84
239000000543 intermediate Substances 0.000 abstract description 2
241000196324 Embryophyta Species 0.000 description 217
239000002904 solvent Substances 0.000 description 148
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 103
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 101
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 73
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 68
238000012360 testing method Methods 0.000 description 62
238000006243 chemical reaction Methods 0.000 description 61
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 59
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
108090000623 proteins and genes Proteins 0.000 description 57
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 53
150000003254 radicals Chemical class 0.000 description 52
239000003995 emulsifying agent Substances 0.000 description 48
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
125000004432 carbon atom Chemical group C* 0.000 description 44
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 41
230000002829 reductive effect Effects 0.000 description 36
239000011541 reaction mixture Substances 0.000 description 31
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
235000018102 proteins Nutrition 0.000 description 28
102000004169 proteins and genes Human genes 0.000 description 28
150000003839 salts Chemical class 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000003112 inhibitor Substances 0.000 description 27
241000238876 Acari Species 0.000 description 26
230000015572 biosynthetic process Effects 0.000 description 26
239000012141 concentrate Substances 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
230000000749 insecticidal effect Effects 0.000 description 24
238000005160 1H NMR spectroscopy Methods 0.000 description 23
125000000623 heterocyclic group Chemical group 0.000 description 23
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000003054 catalyst Substances 0.000 description 21
239000000126 substance Substances 0.000 description 21
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
230000009471 action Effects 0.000 description 20
238000003786 synthesis reaction Methods 0.000 description 20
230000009261 transgenic effect Effects 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
229960001760 dimethyl sulfoxide Drugs 0.000 description 19
239000003814 drug Substances 0.000 description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 17
229920000742 Cotton Polymers 0.000 description 17
241000219146 Gossypium Species 0.000 description 17
102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 17
239000002585 base Substances 0.000 description 17
229910052757 nitrogen Inorganic materials 0.000 description 17
239000012074 organic phase Substances 0.000 description 17
239000007921 spray Substances 0.000 description 17
240000008042 Zea mays Species 0.000 description 16
235000002017 Zea mays subsp mays Nutrition 0.000 description 16
125000002877 alkyl aryl group Chemical group 0.000 description 16
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 16
239000004009 herbicide Substances 0.000 description 16
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 16
239000010695 polyglycol Substances 0.000 description 16
229920000151 polyglycol Polymers 0.000 description 16
125000001424 substituent group Chemical group 0.000 description 16
125000004122 cyclic group Chemical group 0.000 description 15
238000004519 manufacturing process Methods 0.000 description 15
239000000047 product Substances 0.000 description 15
102000004190 Enzymes Human genes 0.000 description 14
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229940088598 enzyme Drugs 0.000 description 14
125000005842 heteroatom Chemical group 0.000 description 14
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 13
125000003118 aryl group Chemical group 0.000 description 13
235000005822 corn Nutrition 0.000 description 13
239000012071 phase Substances 0.000 description 13
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 13
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 12
229910052938 sodium sulfate Inorganic materials 0.000 description 12
235000011152 sodium sulphate Nutrition 0.000 description 12
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 11
235000013601 eggs Nutrition 0.000 description 11
235000019253 formic acid Nutrition 0.000 description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 10
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
241000258242 Siphonaptera Species 0.000 description 10
125000000217 alkyl group Chemical group 0.000 description 10
125000003277 amino group Chemical group 0.000 description 10
239000012043 crude product Substances 0.000 description 10
230000002068 genetic effect Effects 0.000 description 10
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 10
229920006395 saturated elastomer Polymers 0.000 description 10
230000009466 transformation Effects 0.000 description 10
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 9
241000239290 Araneae Species 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
150000003863 ammonium salts Chemical class 0.000 description 9
239000008346 aqueous phase Substances 0.000 description 9
238000009395 breeding Methods 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
238000010353 genetic engineering Methods 0.000 description 9
230000002363 herbicidal effect Effects 0.000 description 9
230000001976 improved effect Effects 0.000 description 9
125000004433 nitrogen atom Chemical group N* 0.000 description 9
239000003921 oil Substances 0.000 description 9
238000007254 oxidation reaction Methods 0.000 description 9
238000012545 processing Methods 0.000 description 9
239000000725 suspension Substances 0.000 description 9
206010021929 Infertility male Diseases 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
208000007466 Male Infertility Diseases 0.000 description 8
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
125000000304 alkynyl group Chemical group 0.000 description 8
230000001488 breeding effect Effects 0.000 description 8
235000013339 cereals Nutrition 0.000 description 8
125000000753 cycloalkyl group Chemical group 0.000 description 8
229940079593 drug Drugs 0.000 description 8
238000000105 evaporative light scattering detection Methods 0.000 description 8
125000001072 heteroaryl group Chemical group 0.000 description 8
238000004128 high performance liquid chromatography Methods 0.000 description 8
230000035772 mutation Effects 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 description 7
240000002791 Brassica napus Species 0.000 description 7
101710151559 Crystal protein Proteins 0.000 description 7
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239000005799 Isopyrazam Substances 0.000 description 7
238000005481 NMR spectroscopy Methods 0.000 description 7
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125000003545 alkoxy group Chemical group 0.000 description 7
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150000001412 amines Chemical class 0.000 description 7
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235000013399 edible fruits Nutrition 0.000 description 7
125000001188 haloalkyl group Chemical group 0.000 description 7
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MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
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235000014698 Brassica juncea var multisecta Nutrition 0.000 description 5
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