DE3537884A1 - Pyrazolin-verbindungen, verfahren zu ihrer herstellung und ihre verwendung bei der bekaempfung von schadinsekten - Google Patents
Pyrazolin-verbindungen, verfahren zu ihrer herstellung und ihre verwendung bei der bekaempfung von schadinsektenInfo
- Publication number
- DE3537884A1 DE3537884A1 DE19853537884 DE3537884A DE3537884A1 DE 3537884 A1 DE3537884 A1 DE 3537884A1 DE 19853537884 DE19853537884 DE 19853537884 DE 3537884 A DE3537884 A DE 3537884A DE 3537884 A1 DE3537884 A1 DE 3537884A1
- Authority
- DE
- Germany
- Prior art keywords
- carboxamide
- pyrazoline
- formula
- hydrogen
- group
- Prior art date
- 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.)
- Ceased
Links
- 150000003219 pyrazolines Chemical class 0.000 title claims description 24
- 241000238631 Hexapoda Species 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 7
- -1 2,3-dihydro-2,2-dimethylbenzofuran-5-yl-- Chemical class 0.000 claims description 186
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 51
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 21
- PPVUWDCETZMPLT-UHFFFAOYSA-N 1,3-dihydropyrazole-2-carboxamide Chemical compound NC(=O)N1CC=CN1 PPVUWDCETZMPLT-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 241000607479 Yersinia pestis Species 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052736 halogen Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- IFMDMFBBMTXOED-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-(2,2-dimethyl-3h-1-benzofuran-5-yl)-5-phenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C=1C=C2OC(C)(C)CC2=CC=1NC(=O)N(N1)CC(C=2C=CC(Cl)=CC=2)=C1C1=CC=CC=C1 IFMDMFBBMTXOED-UHFFFAOYSA-N 0.000 claims 1
- QJVDWVHKUPPHNY-UHFFFAOYSA-N 5,5,6,6-tetrafluorocyclohexa-1,3-diene Chemical compound FC1(F)C=CC=CC1(F)F QJVDWVHKUPPHNY-UHFFFAOYSA-N 0.000 claims 1
- ARKLDSUYDZUISS-UHFFFAOYSA-N 5-[4-(difluoromethoxy)phenyl]-4-(4-fluorophenyl)-n-(2,2,3,3-tetrafluoro-1-benzofuran-5-yl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC(F)F)=CC=C1C1=C(C=2C=CC(F)=CC=2)CN(C(=O)NC=2C=C3C(F)(F)C(F)(F)OC3=CC=2)N1 ARKLDSUYDZUISS-UHFFFAOYSA-N 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 235000008504 concentrate Nutrition 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 239000000969 carrier Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- GFDJEJFDDZSGCB-UHFFFAOYSA-N 1-phenyl-3H-pyrazole-2-carboxamide Chemical compound C1(=CC=CC=C1)N1N(CC=C1)C(N)=O GFDJEJFDDZSGCB-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000012259 ether extract Substances 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 125000000068 chlorophenyl group Chemical group 0.000 description 6
- 210000003608 fece Anatomy 0.000 description 6
- 239000002917 insecticide Substances 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000010871 livestock manure Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- FWPHQUJGZVELBK-UHFFFAOYSA-N 2,3-dihydropyrrole-1-carboxamide Chemical compound NC(=O)N1CCC=C1 FWPHQUJGZVELBK-UHFFFAOYSA-N 0.000 description 4
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 206010026749 Mania Diseases 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000003857 carboxamides Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- 241000462639 Epilachna varivestis Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001521235 Spodoptera eridania Species 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229960000892 attapulgite Drugs 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001207 fluorophenyl group Chemical group 0.000 description 3
- 235000014666 liquid concentrate Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- 229910052625 palygorskite Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 2
- GDEZSMXXDMVYHT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-4-nitrobenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1 GDEZSMXXDMVYHT-UHFFFAOYSA-N 0.000 description 2
- KCIGEQYJXFMPQV-UHFFFAOYSA-N 1-(4-fluorophenyl)-3H-pyrazole-2-carboxamide Chemical compound FC1=CC=C(C=C1)N1N(CC=C1)C(=O)N KCIGEQYJXFMPQV-UHFFFAOYSA-N 0.000 description 2
- WYUJZLSRJRHRSK-UHFFFAOYSA-N 2,2,3,3-tetrafluoro-1-benzofuran-5-amine Chemical compound NC1=CC=C2OC(F)(F)C(F)(F)C2=C1 WYUJZLSRJRHRSK-UHFFFAOYSA-N 0.000 description 2
- LWDIQKVNWBXIMP-UHFFFAOYSA-N 2,2-dimethyl-3h-1-benzofuran-5-amine Chemical compound NC1=CC=C2OC(C)(C)CC2=C1 LWDIQKVNWBXIMP-UHFFFAOYSA-N 0.000 description 2
- YTISFYMPVILQRL-UHFFFAOYSA-N 4-(4-chlorophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(Cl)C=C1 YTISFYMPVILQRL-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- FBWKCZBSQZCRPW-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-phenyl-2,3-dihydro-1h-pyrazole Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C=CC=CC=2)CNN1 FBWKCZBSQZCRPW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000021537 Beetroot Nutrition 0.000 description 2
- 241000489976 Diabrotica undecimpunctata howardi Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241001477931 Mythimna unipuncta Species 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 241000255969 Pieris brassicae Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 2
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- 238000002474 experimental method Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
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- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- CYDMKXAKBXMPHN-UHFFFAOYSA-N n,5-bis(2,2-difluoro-1,3-benzodioxol-5-yl)-4-(4-fluorophenyl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=C3OC(F)(F)OC3=CC=2)NN(C(=O)NC=2C=C3OC(F)(F)OC3=CC=2)C1 CYDMKXAKBXMPHN-UHFFFAOYSA-N 0.000 description 1
- QSHVRMBMYMRGKV-UHFFFAOYSA-N n-(2,2-difluoro-1,3-benzodioxol-5-yl)-4,5-bis(4-fluorophenyl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC(F)=CC=2)NN(C(=O)NC=2C=C3OC(F)(F)OC3=CC=2)C1 QSHVRMBMYMRGKV-UHFFFAOYSA-N 0.000 description 1
- ITYUTJNGXYYIKZ-UHFFFAOYSA-N n-(2,2-difluoro-1,3-benzodioxol-5-yl)-4-(4-fluorophenyl)-5-(4-methylphenyl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC(F)=CC=2)CN(C(=O)NC=2C=C3OC(F)(F)OC3=CC=2)N1 ITYUTJNGXYYIKZ-UHFFFAOYSA-N 0.000 description 1
- CGBIMKCPCSHZPK-UHFFFAOYSA-N n-(2,2-dimethyl-3h-1-benzofuran-5-yl)-5-(2-fluorophenyl)-4-(4-fluorophenyl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C=1C=C2OC(C)(C)CC2=CC=1NC(=O)N(N1)CC(C=2C=CC(F)=CC=2)=C1C1=CC=CC=C1F CGBIMKCPCSHZPK-UHFFFAOYSA-N 0.000 description 1
- SNZJZAGEFRLCLO-UHFFFAOYSA-N n-(2,2-dimethyl-3h-1-benzofuran-5-yl)-5-(4-methoxyphenyl)-4-phenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC=CC=2)CN(C(=O)NC=2C=C3CC(C)(C)OC3=CC=2)N1 SNZJZAGEFRLCLO-UHFFFAOYSA-N 0.000 description 1
- LZYORLQZBLMYLV-UHFFFAOYSA-N n-(2,2-dimethyl-3h-1-benzofuran-5-yl)-5-(7-methoxy-2,2-dimethyl-1,3-benzodioxol-5-yl)-4-phenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C=1C=2OC(C)(C)OC=2C(OC)=CC=1C(NN(C1)C(=O)NC=2C=C3CC(C)(C)OC3=CC=2)=C1C1=CC=CC=C1 LZYORLQZBLMYLV-UHFFFAOYSA-N 0.000 description 1
- FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
- KOMRMEPVCOGZIF-UHFFFAOYSA-N n-(4-phenoxyphenyl)-4,5-diphenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)NN1C(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 KOMRMEPVCOGZIF-UHFFFAOYSA-N 0.000 description 1
- TWDXGCVWGPCNOM-UHFFFAOYSA-N n-(7-ethyl-2,2,3,3-tetrafluoro-1-benzofuran-5-yl)-4,5-bis(4-fluorophenyl)-1,3-dihydropyrazole-2-carboxamide Chemical compound C=1C(C(C(F)(F)O2)(F)F)=C2C(CC)=CC=1NC(=O)N(N1)CC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 TWDXGCVWGPCNOM-UHFFFAOYSA-N 0.000 description 1
- CRVPHYKUTPKPQL-UHFFFAOYSA-N n-[7-(chloromethyl)-2,2-dimethyl-1,3-benzodioxol-5-yl]-4,5-diphenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C=1C(CCl)=C2OC(C)(C)OC2=CC=1NC(=O)N(N1)CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CRVPHYKUTPKPQL-UHFFFAOYSA-N 0.000 description 1
- DXZRKYVIICPPOM-UHFFFAOYSA-N n-[7-(difluoromethoxy)-2,2-dimethyl-3h-1-benzofuran-5-yl]-4,5-diphenyl-1,3-dihydropyrazole-2-carboxamide Chemical compound C=1C(OC(F)F)=C2OC(C)(C)CC2=CC=1NC(=O)N(N1)CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 DXZRKYVIICPPOM-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 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
- 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 1
- 239000002002 slurry Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000012360 testing method Methods 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
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66467484A | 1984-10-25 | 1984-10-25 | |
| US70962685A | 1985-03-08 | 1985-03-08 | |
| US77972185A | 1985-09-24 | 1985-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3537884A1 true DE3537884A1 (de) | 1986-04-30 |
Family
ID=27418114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853537884 Ceased DE3537884A1 (de) | 1984-10-25 | 1985-10-24 | Pyrazolin-verbindungen, verfahren zu ihrer herstellung und ihre verwendung bei der bekaempfung von schadinsekten |
Country Status (30)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997028143A1 (en) * | 1996-02-01 | 1997-08-07 | The Procter & Gamble Company | Dihydrobenzofuran and related compounds useful as anti-inflammatory agents |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3545786A1 (de) * | 1985-12-21 | 1987-06-25 | Schering Ag | Pyrazolinderivate, ihre herstellung und ihre verwendung als mittel mit insektizider wirkung |
| AU1993988A (en) * | 1987-07-17 | 1989-02-13 | E.I. Du Pont De Nemours And Company | Insecticidal pyrazolines |
| IL87131A0 (en) * | 1987-07-17 | 1988-12-30 | Du Pont | Pyrazoline derivatives and their use as insecticides |
| AU4316189A (en) * | 1988-09-22 | 1990-04-18 | E.I. Du Pont De Nemours And Company | Substituted indazole arthropodicides |
| JPH05112556A (ja) * | 1991-10-18 | 1993-05-07 | Nippon Bayeragrochem Kk | 殺虫性ピラゾリン類 |
| CN116265457B (zh) * | 2021-12-17 | 2024-09-03 | 湖南化工研究院有限公司 | N-氧杂稠环酰胺类化合物及其制备方法与应用 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2529689A1 (de) * | 1974-07-12 | 1976-01-29 | Philips Nv | Neue pyrazolinverbindungen |
| US4174393A (en) * | 1975-07-09 | 1979-11-13 | Duphar International Research B.V. | 1,3,4-Substituted pyrazoline derivatives |
| EP0058424A2 (en) * | 1981-02-17 | 1982-08-25 | Nissan Chemical Industries Ltd. | Pyrazoline derivatives |
| EP0113213A2 (en) * | 1982-12-30 | 1984-07-11 | Schering Agrochemicals Limited | Pyrazoline insecticides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795264A (fr) * | 1972-02-09 | 1973-08-09 | Philips Nv | Nouveaux composes de pyrazoline a activite insecticide |
| NL183400C (nl) * | 1976-01-09 | 1988-10-17 | Duphar Int Res | Werkwijze ter bereiding van een insecticide preparaat dat een pyrazoline-verbinding bevat en werkwijze ter bereiding van een pyrazoline-verbinding met insecticide werking. |
| EP0021506B1 (en) * | 1979-07-03 | 1983-09-07 | Duphar International Research B.V | New pyrazoline derivatives, method of preparing the new compounds, as well as insecticidal composition on the basis of these new compounds |
| US4407813A (en) * | 1981-02-17 | 1983-10-04 | Nissan Chemical Industries Ltd. | Insecticidal pyrazoline derivatives and composition |
-
1985
- 1985-10-15 AU AU48598/85A patent/AU556949B2/en not_active Ceased
- 1985-10-16 CA CA000493018A patent/CA1265145A/en not_active Expired - Lifetime
- 1985-10-16 IN IN864/DEL/85A patent/IN166473B/en unknown
- 1985-10-21 IL IL76771A patent/IL76771A0/xx not_active IP Right Cessation
- 1985-10-23 AP APAP/P/1985/000014A patent/AP36A/en active
- 1985-10-23 AT AT0306085A patent/ATA306085A/de not_active Application Discontinuation
- 1985-10-23 LU LU86134A patent/LU86134A1/fr unknown
- 1985-10-23 GB GB08526175A patent/GB2166137B/en not_active Expired
- 1985-10-24 KR KR1019850007838A patent/KR880001568B1/ko not_active Expired
- 1985-10-24 DE DE19853537884 patent/DE3537884A1/de not_active Ceased
- 1985-10-24 CN CN85107882.6A patent/CN1004272B/zh not_active Expired
- 1985-10-24 HU HU854103A patent/HU199808B/hu unknown
- 1985-10-24 YU YU1686/85A patent/YU45287B/xx unknown
- 1985-10-24 NL NL8502913A patent/NL8502913A/nl not_active Application Discontinuation
- 1985-10-24 IT IT22601/85A patent/IT1203596B/it active
- 1985-10-24 SE SE8505026A patent/SE8505026L/xx not_active Application Discontinuation
- 1985-10-24 NZ NZ213953A patent/NZ213953A/xx unknown
- 1985-10-24 ES ES548170A patent/ES8701757A1/es not_active Expired
- 1985-10-24 CS CS857615A patent/CS252497B2/cs unknown
- 1985-10-24 CH CH4582/85A patent/CH666029A5/de not_active IP Right Cessation
- 1985-10-24 BR BR8505326A patent/BR8505326A/pt unknown
- 1985-10-24 DK DK487885A patent/DK487885A/da not_active Application Discontinuation
- 1985-10-25 BE BE0/215778A patent/BE903521A/fr not_active IP Right Cessation
- 1985-10-25 PL PL1985255938A patent/PL150265B1/pl unknown
- 1985-10-25 OA OA58712A patent/OA08127A/xx unknown
- 1985-10-25 RO RO120544A patent/RO92966B/ro unknown
- 1985-10-25 GR GR852585A patent/GR852585B/el unknown
- 1985-10-25 FR FR8515890A patent/FR2572400A1/fr not_active Withdrawn
- 1985-10-27 EG EG680/85A patent/EG17848A/xx active
-
1987
- 1987-09-29 MY MYPI87002197A patent/MY102602A/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2529689A1 (de) * | 1974-07-12 | 1976-01-29 | Philips Nv | Neue pyrazolinverbindungen |
| US4174393A (en) * | 1975-07-09 | 1979-11-13 | Duphar International Research B.V. | 1,3,4-Substituted pyrazoline derivatives |
| EP0058424A2 (en) * | 1981-02-17 | 1982-08-25 | Nissan Chemical Industries Ltd. | Pyrazoline derivatives |
| EP0113213A2 (en) * | 1982-12-30 | 1984-07-11 | Schering Agrochemicals Limited | Pyrazoline insecticides |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997028143A1 (en) * | 1996-02-01 | 1997-08-07 | The Procter & Gamble Company | Dihydrobenzofuran and related compounds useful as anti-inflammatory agents |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8128 | New person/name/address of the agent |
Representative=s name: VOSSIUS, V., DIPL.-CHEM. DR.RER.NAT. TAUCHNER, P., |
|
| 8131 | Rejection |