UA77546C2 - Pyrazolepyrimidines and using thereof to control harmful organisms - Google Patents
Pyrazolepyrimidines and using thereof to control harmful organisms Download PDFInfo
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- UA77546C2 UA77546C2 UA20041210941A UA20041210941A UA77546C2 UA 77546 C2 UA77546 C2 UA 77546C2 UA 20041210941 A UA20041210941 A UA 20041210941A UA 20041210941 A UA20041210941 A UA 20041210941A UA 77546 C2 UA77546 C2 UA 77546C2
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- UA
- Ukraine
- Prior art keywords
- formula
- carbon atoms
- methyl
- plants
- cycloalkyl
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- APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 claims abstract description 17
- -1 amino, hydroxy Chemical group 0.000 claims description 271
- 239000013543 active substance Substances 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 239000003085 diluting agent Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- XMBHGEAQFMUJMX-UHFFFAOYSA-N 2,4-dihydro-1h-pyrazolo[4,3-d]pyrimidine-3,5-dione Chemical class N1=C(O)N=C2C(O)=NNC2=C1 XMBHGEAQFMUJMX-UHFFFAOYSA-N 0.000 claims description 5
- 125000004666 alkoxyiminoalkyl group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 2
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 90
- 239000000126 substance Substances 0.000 abstract description 22
- 239000000543 intermediate Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 241000196324 Embryophyta Species 0.000 description 84
- 125000004432 carbon atom Chemical group C* 0.000 description 80
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- 239000000203 mixture Substances 0.000 description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 241000894007 species Species 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 21
- 229910052801 chlorine Inorganic materials 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 230000009471 action Effects 0.000 description 16
- 239000011737 fluorine Substances 0.000 description 16
- 229910052731 fluorine Inorganic materials 0.000 description 16
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 125000004494 ethyl ester group Chemical group 0.000 description 15
- 238000007796 conventional method Methods 0.000 description 14
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- 239000012074 organic phase Substances 0.000 description 14
- 238000012545 processing Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 13
- 239000003995 emulsifying agent Substances 0.000 description 13
- 230000003993 interaction Effects 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
- 229910052794 bromium Inorganic materials 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 12
- 235000011167 hydrochloric acid Nutrition 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 241000700605 Viruses Species 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 230000001681 protective effect Effects 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 241000607479 Yersinia pestis Species 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 241000233866 Fungi Species 0.000 description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 240000008042 Zea mays Species 0.000 description 9
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 235000005822 corn Nutrition 0.000 description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 235000011118 potassium hydroxide Nutrition 0.000 description 9
- 108090000623 proteins and genes Proteins 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 8
- 244000299507 Gossypium hirsutum Species 0.000 description 8
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
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- 150000002148 esters Chemical class 0.000 description 7
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 7
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
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- 241000894006 Bacteria Species 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
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- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
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- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 6
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- ZKSRIPVNRIUEOM-UHFFFAOYSA-N 1,2-dihydropyrazolo[4,3-d]pyrimidin-3-one Chemical class N1=CN=C2C(O)=NNC2=C1 ZKSRIPVNRIUEOM-UHFFFAOYSA-N 0.000 description 4
- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 description 4
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- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-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
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229940074152 thuringiensin Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 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
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10223917A DE10223917A1 (de) | 2002-05-29 | 2002-05-29 | Pyrazolopyrimidine |
PCT/EP2003/005159 WO2004000844A1 (de) | 2002-05-29 | 2003-05-16 | Pyrazolopyrimidine und ihre verwendung zur bekämpfung von schädlichen organismen |
Publications (1)
Publication Number | Publication Date |
---|---|
UA77546C2 true UA77546C2 (en) | 2006-12-15 |
Family
ID=29432434
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA20041210941A UA77546C2 (en) | 2002-05-29 | 2003-05-16 | Pyrazolepyrimidines and using thereof to control harmful organisms |
Country Status (20)
Country | Link |
---|---|
US (1) | US20060089499A1 (xx) |
EP (1) | EP1513843B1 (xx) |
JP (1) | JP2005533070A (xx) |
KR (1) | KR20050004234A (xx) |
CN (1) | CN1671709A (xx) |
AT (1) | ATE366253T1 (xx) |
AU (1) | AU2003240258A1 (xx) |
BR (1) | BR0311538A (xx) |
CA (1) | CA2487544A1 (xx) |
DE (2) | DE10223917A1 (xx) |
DK (1) | DK1513843T3 (xx) |
ES (1) | ES2289300T3 (xx) |
IL (1) | IL165348A0 (xx) |
MX (1) | MXPA04011824A (xx) |
PL (1) | PL373467A1 (xx) |
PT (1) | PT1513843E (xx) |
RU (1) | RU2331643C2 (xx) |
UA (1) | UA77546C2 (xx) |
WO (1) | WO2004000844A1 (xx) |
ZA (1) | ZA200409618B (xx) |
Families Citing this family (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7205308B2 (en) | 2002-09-04 | 2007-04-17 | Schering Corporation | Trisubstituted 7-aminopyrazolopyrimidines as cyclin dependent kinase inhibitors |
CA2497450C (en) | 2002-09-04 | 2011-05-31 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
US8673924B2 (en) | 2002-09-04 | 2014-03-18 | Merck Sharp & Dohme Corp. | Substituted pyrazolo[1,5-a]pyrimidines as cyclin dependent kinase inhibitors |
US7161003B1 (en) | 2002-09-04 | 2007-01-09 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
KR20050057072A (ko) | 2002-09-04 | 2005-06-16 | 쉐링 코포레이션 | 사이클린 의존성 키나제 억제제로서의 피라졸로피리미딘 |
US7119200B2 (en) | 2002-09-04 | 2006-10-10 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
US7196078B2 (en) | 2002-09-04 | 2007-03-27 | Schering Corpoartion | Trisubstituted and tetrasubstituted pyrazolopyrimidines as cyclin dependent kinase inhibitors |
WO2004026229A2 (en) | 2002-09-04 | 2004-04-01 | Schering Corporation | Pyrazolo[1,5-a]pyrimidines compounds as cyclin dependent kinase inhibitors |
CA2497444C (en) | 2002-09-04 | 2010-11-30 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
US8580782B2 (en) | 2002-09-04 | 2013-11-12 | Merck Sharp & Dohme Corp. | Substituted pyrazolo[1,5-a]pyrimidines as cyclin dependent kinase inhibitors |
JP4564485B2 (ja) * | 2003-02-28 | 2010-10-20 | 帝人ファーマ株式会社 | ピラゾロ[1,5−a]ピリミジン誘導体 |
EP1608652A1 (en) * | 2003-03-31 | 2005-12-28 | Vernalis (Cambridge) Limited | Pyrazolopyrimidine compounds and their use in medicine |
JP2006526583A (ja) * | 2003-06-03 | 2006-11-24 | ビーエーエスエフ アクチェンゲゼルシャフト | 置換ピラゾロピリミジン、それらの製造方法及び有害菌の防除のためのそれらの使用、並びにそれらを含む組成物 |
MXPA05013902A (es) * | 2003-06-27 | 2006-02-24 | Bayer Cropscience Ag | Pirazolopirimidinas. |
DE10357565A1 (de) * | 2003-12-10 | 2005-07-07 | Bayer Cropscience Ag | Pyrazolopyrimidine |
DE10357568A1 (de) * | 2003-12-10 | 2005-07-07 | Bayer Cropscience Ag | Pyrazolopyrimidine |
DE10357567A1 (de) * | 2003-12-10 | 2005-07-07 | Bayer Cropscience Ag | Pyrazolopyrimidine |
DE102004008807A1 (de) | 2004-02-20 | 2005-09-08 | Bayer Cropscience Ag | Pyrazolopyrimidine |
EP1720879A2 (de) * | 2004-02-25 | 2006-11-15 | Basf Aktiengesellschaft | Azolopyrimidin-verbindungen und ihre verwendung zur bekämpfung von schadpilzen |
DE102005007534A1 (de) | 2005-02-17 | 2006-08-31 | Bayer Cropscience Ag | Pyrazolopyrimidine |
CN101287695A (zh) * | 2005-03-18 | 2008-10-15 | 巴斯福股份公司 | 制备5-卤代-2,4,6-三氟间苯二甲酸的方法 |
JP2007008864A (ja) * | 2005-06-30 | 2007-01-18 | Bayer Cropscience Ag | ピラゾロピリミジン誘導体及び農園芸用殺菌剤 |
MX2008000708A (es) * | 2005-07-27 | 2008-03-18 | Basf Ag | 5-metil-6-fenilpirazololpirimidin-2-ilaminas fungicidas. |
BRPI0613941A2 (pt) * | 2005-07-27 | 2016-11-22 | Basf Ag | compostos, processo para preparar compostos, agente fungicida, semente, e, processo para combater fungos nocivos fitopatogênicos |
EP1931676B1 (en) | 2005-10-06 | 2011-11-16 | Schering Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
WO2007101859A1 (de) * | 2006-03-07 | 2007-09-13 | Basf Se | Substituierte pyrazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
WO2007101804A1 (de) * | 2006-03-07 | 2007-09-13 | Basf Se | Substituierte pyrazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
DE102006039255A1 (de) * | 2006-08-17 | 2008-02-21 | Bayer Cropscience Ag | Insektizide heterocyclische Carbonsäurederivate |
WO2008046856A2 (de) * | 2006-10-18 | 2008-04-24 | Basf Se | Fungizide zusammensetzungen |
JP2010515706A (ja) * | 2007-01-11 | 2010-05-13 | ビーエーエスエフ ソシエタス・ヨーロピア | アリール置換縮合ピリミジンの製造方法 |
JP7179161B2 (ja) | 2018-09-10 | 2022-11-28 | イーライ リリー アンド カンパニー | 乾癬および全身性エリテマトーデスの処置に有用なピラゾロ[1,5-a]ピリミジン-3-カルボキサミド誘導体 |
CN110016036B (zh) * | 2019-05-16 | 2022-06-03 | 辽宁大学 | 吡唑并[1,5-a]嘧啶类化合物及其制备方法和应用 |
AR121251A1 (es) | 2020-02-12 | 2022-05-04 | Lilly Co Eli | Compuestos de 7-(metilamino)pirazolo[1,5-a]pirimidina-3-carboxamida |
CN115734965A (zh) * | 2020-06-26 | 2023-03-03 | 日本农药株式会社 | 芳基四氢哒嗪衍生物或其盐类、和含有该化合物的杀虫剂及其使用方法 |
CN113287620B (zh) * | 2021-06-18 | 2021-11-19 | 浙江大学 | 1H-吡唑并[3,4-d]嘧啶类化合物在制备禾谷镰刀菌杀菌剂中的应用 |
AR128103A1 (es) * | 2021-12-28 | 2024-03-27 | Nihon Nohyaku Co Ltd | Derivado de ariltetrahidropiridazina o sal de este y agente insecticida que contiene el compuesto y método para utilizarlo |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3130633A1 (de) * | 1981-08-01 | 1983-02-17 | Basf Ag, 6700 Ludwigshafen | 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide |
US5817663A (en) * | 1996-10-07 | 1998-10-06 | American Cyanamid Company | Pentafluorophenylazolopyrimidines |
US6156925A (en) * | 1998-09-25 | 2000-12-05 | American Cyanamid Company | Process for the preparation of halogenated phenylmaloates |
US6552026B2 (en) * | 1999-06-14 | 2003-04-22 | Basf Aktiengesellschaft | 6-phenyl-pyrazolopyrimidines |
JP2001019693A (ja) * | 1999-06-14 | 2001-01-23 | American Cyanamid Co | 殺菌・殺カビ性6−フェニル−ピラゾロピリミジン |
-
2002
- 2002-05-29 DE DE10223917A patent/DE10223917A1/de not_active Withdrawn
-
2003
- 2003-05-16 PL PL03373467A patent/PL373467A1/xx not_active Application Discontinuation
- 2003-05-16 BR BR0311538-0A patent/BR0311538A/pt not_active IP Right Cessation
- 2003-05-16 US US10/515,484 patent/US20060089499A1/en not_active Abandoned
- 2003-05-16 AT AT03732394T patent/ATE366253T1/de not_active IP Right Cessation
- 2003-05-16 RU RU2004139028/04A patent/RU2331643C2/ru not_active IP Right Cessation
- 2003-05-16 DE DE50307615T patent/DE50307615D1/de not_active Expired - Fee Related
- 2003-05-16 WO PCT/EP2003/005159 patent/WO2004000844A1/de active IP Right Grant
- 2003-05-16 CA CA002487544A patent/CA2487544A1/en not_active Abandoned
- 2003-05-16 PT PT03732394T patent/PT1513843E/pt unknown
- 2003-05-16 CN CNA038183765A patent/CN1671709A/zh active Pending
- 2003-05-16 MX MXPA04011824A patent/MXPA04011824A/es active IP Right Grant
- 2003-05-16 EP EP03732394A patent/EP1513843B1/de not_active Expired - Lifetime
- 2003-05-16 ES ES03732394T patent/ES2289300T3/es not_active Expired - Lifetime
- 2003-05-16 IL IL16534803A patent/IL165348A0/xx unknown
- 2003-05-16 JP JP2004514640A patent/JP2005533070A/ja active Pending
- 2003-05-16 KR KR10-2004-7019134A patent/KR20050004234A/ko not_active Application Discontinuation
- 2003-05-16 AU AU2003240258A patent/AU2003240258A1/en not_active Abandoned
- 2003-05-16 DK DK03732394T patent/DK1513843T3/da active
- 2003-05-16 UA UA20041210941A patent/UA77546C2/uk unknown
-
2004
- 2004-11-29 ZA ZA200409618A patent/ZA200409618B/xx unknown
Also Published As
Publication number | Publication date |
---|---|
DK1513843T3 (da) | 2007-11-05 |
MXPA04011824A (es) | 2005-03-31 |
PL373467A1 (en) | 2005-09-05 |
EP1513843A1 (de) | 2005-03-16 |
WO2004000844A1 (de) | 2003-12-31 |
RU2331643C2 (ru) | 2008-08-20 |
DE10223917A1 (de) | 2003-12-11 |
PT1513843E (pt) | 2007-09-26 |
ZA200409618B (en) | 2006-03-29 |
RU2004139028A (ru) | 2005-07-10 |
BR0311538A (pt) | 2005-03-01 |
KR20050004234A (ko) | 2005-01-12 |
US20060089499A1 (en) | 2006-04-27 |
ATE366253T1 (de) | 2007-07-15 |
AU2003240258A1 (en) | 2004-01-06 |
IL165348A0 (en) | 2006-01-15 |
CA2487544A1 (en) | 2003-12-31 |
CN1671709A (zh) | 2005-09-21 |
ES2289300T3 (es) | 2008-02-01 |
EP1513843B1 (de) | 2007-07-04 |
JP2005533070A (ja) | 2005-11-04 |
DE50307615D1 (de) | 2007-08-16 |
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