CA2558848C - Isoxazoline-substituted benzamide compound and pesticide - Google Patents
Isoxazoline-substituted benzamide compound and pesticide Download PDFInfo
- Publication number
- CA2558848C CA2558848C CA2558848A CA2558848A CA2558848C CA 2558848 C CA2558848 C CA 2558848C CA 2558848 A CA2558848 A CA 2558848A CA 2558848 A CA2558848 A CA 2558848A CA 2558848 C CA2558848 C CA 2558848C
- Authority
- CA
- Canada
- Prior art keywords
- c4alkyl
- c6alkyl
- phenyl
- substituted
- atom
- 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.)
- Expired - Lifetime
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- -1 Isoxazoline-substituted benzamide compound Chemical class 0.000 title claims abstract description 355
- 239000000575 pesticide Substances 0.000 title claims abstract description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 361
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 361
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 207
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 188
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 183
- 125000005843 halogen group Chemical group 0.000 claims abstract description 156
- 150000001875 compounds Chemical class 0.000 claims abstract description 155
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 144
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 99
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 78
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 73
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 68
- 229910052717 sulfur Chemical group 0.000 claims abstract description 64
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 50
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 18
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 400
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 179
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 153
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 87
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 87
- 125000002947 alkylene group Chemical group 0.000 claims description 78
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 45
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 39
- 101100294104 Caenorhabditis elegans nhr-34 gene Proteins 0.000 claims description 39
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 38
- JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical group C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 claims description 36
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 31
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 30
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 29
- RBIIKVXVYVANCQ-CUWPLCDZSA-N (2s,4s,5s)-5-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-6-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-4-hydroxy-2-propan-2-ylhexanamide Chemical group C1C(C)(C)N(C[C@H](N)[C@@H](O)C[C@@H](C(C)C)C(=O)NCC(C)(C)C(N)=O)CC(=O)N1C1=CC=CC=C1Cl RBIIKVXVYVANCQ-CUWPLCDZSA-N 0.000 claims description 28
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 28
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 28
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 27
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 101100365011 Arabidopsis thaliana SCL33 gene Proteins 0.000 claims description 24
- 101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
- 101100451196 Caenorhabditis elegans hizr-1 gene Proteins 0.000 claims description 16
- 241000124008 Mammalia Species 0.000 claims description 15
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 14
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 14
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 14
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 13
- 239000013057 ectoparasiticide Substances 0.000 claims description 13
- 125000004043 oxo group Chemical group O=* 0.000 claims description 13
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 13
- RFEJUZJILGIRHQ-XRIOVQLTSA-N 2,3-dihydroxybutanedioic acid;3-[(2s)-1-methylpyrrolidin-2-yl]pyridine Chemical compound OC(=O)C(O)C(O)C(O)=O.OC(=O)C(O)C(O)C(O)=O.CN1CCC[C@H]1C1=CC=CN=C1 RFEJUZJILGIRHQ-XRIOVQLTSA-N 0.000 claims description 12
- YCAGGFXSFQFVQL-UHFFFAOYSA-N Endothion Chemical compound COC1=COC(CSP(=O)(OC)OC)=CC1=O YCAGGFXSFQFVQL-UHFFFAOYSA-N 0.000 claims description 12
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims description 12
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 12
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 11
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 11
- 101150065749 Churc1 gene Proteins 0.000 claims description 11
- 102100038239 Protein Churchill Human genes 0.000 claims description 11
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 8
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 8
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 8
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical group C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- KYMQCBPHCXAPDE-UHFFFAOYSA-N 90594-15-3 Chemical compound N1=C2C=CC=CN2C2=C1C(C)=C(NO)C=N2 KYMQCBPHCXAPDE-UHFFFAOYSA-N 0.000 claims description 7
- 101100478290 Arabidopsis thaliana SR30 gene Proteins 0.000 claims description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000002917 insecticide Substances 0.000 claims description 7
- 125000001863 phosphorothioyl group Chemical group *P(*)(*)=S 0.000 claims description 7
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
- RFEBDZANCVHDLP-UHFFFAOYSA-N 3-[(4-cyanophenyl)methylamino]-6-(trifluoromethyl)quinoxaline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(C(F)(F)F)C=C2N=C1NCC1=CC=C(C#N)C=C1 RFEBDZANCVHDLP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 5
- 230000000895 acaricidal effect Effects 0.000 claims description 5
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 4
- 125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 claims description 4
- 239000000642 acaricide Substances 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 3
- 125000006772 (C1-C6) haloalkylsulfonyloxy group Chemical group 0.000 claims description 3
- 239000003905 agrochemical Substances 0.000 claims description 3
- 108700039708 galantide Proteins 0.000 claims description 3
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 3
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- XPHBRTNHVJSEQD-UHFFFAOYSA-N anidoxime Chemical compound C=1C=CC=CC=1C(CCN(CC)CC)=NOC(=O)NC1=CC=C(OC)C=C1 XPHBRTNHVJSEQD-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 241000258242 Siphonaptera Species 0.000 claims 2
- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical group C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims 2
- 241000238679 Amblyomma Species 0.000 claims 1
- 241000490513 Ctenocephalides canis Species 0.000 claims 1
- 241001480824 Dermacentor Species 0.000 claims 1
- 241001549209 Echidnophaga gallinacea Species 0.000 claims 1
- 241000282324 Felis Species 0.000 claims 1
- 235000018958 Gardenia augusta Nutrition 0.000 claims 1
- 244000111489 Gardenia augusta Species 0.000 claims 1
- 241000179420 Haemaphysalis longicornis Species 0.000 claims 1
- 241000610560 Ixodes ovatus Species 0.000 claims 1
- 241001480847 Ixodes persulcatus Species 0.000 claims 1
- 241000718000 Pulex irritans Species 0.000 claims 1
- 241000238680 Rhipicephalus microplus Species 0.000 claims 1
- 241001481696 Rhipicephalus sanguineus Species 0.000 claims 1
- 241000353223 Xenopsylla cheopis Species 0.000 claims 1
- 238000003287 bathing Methods 0.000 claims 1
- 238000007598 dipping method Methods 0.000 claims 1
- 238000010410 dusting Methods 0.000 claims 1
- 238000007918 intramuscular administration Methods 0.000 claims 1
- 239000007928 intraperitoneal injection Substances 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 466
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 81
- 238000006243 chemical reaction Methods 0.000 description 67
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 67
- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 description 46
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 43
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 43
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 43
- 239000002904 solvent Substances 0.000 description 35
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 27
- 238000004519 manufacturing process Methods 0.000 description 26
- 125000000217 alkyl group Chemical group 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 23
- 229910052739 hydrogen Inorganic materials 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000002585 base Substances 0.000 description 21
- 125000006344 nonafluoro n-butyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 20
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
- 125000006342 heptafluoro i-propyl group Chemical group FC(F)(F)C(F)(*)C(F)(F)F 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 10
- 150000002430 hydrocarbons Chemical group 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 9
- 229910052727 yttrium Inorganic materials 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- 125000001188 haloalkyl group Chemical group 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 235000011181 potassium carbonates Nutrition 0.000 description 8
- 229940086542 triethylamine Drugs 0.000 description 8
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 241000607479 Yersinia pestis Species 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
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- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 238000009304 pastoral farming Methods 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229940093956 potassium carbonate Drugs 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 229940093932 potassium hydroxide Drugs 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
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- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
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- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
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- C07C255/29—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton containing cyano groups and acylated amino groups bound to the carbon skeleton
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- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
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- C07C323/09—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
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- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
- C07D261/16—Benzene-sulfonamido isoxazoles
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004061749 | 2004-03-05 | ||
JP2004-061749 | 2004-03-05 | ||
JP2004-200119 | 2004-07-07 | ||
JP2004200119 | 2004-07-07 | ||
PCT/JP2005/004268 WO2005085216A1 (ja) | 2004-03-05 | 2005-03-04 | イソキサゾリン置換ベンズアミド化合物及び有害生物防除剤 |
Publications (2)
Publication Number | Publication Date |
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CA2558848A1 CA2558848A1 (en) | 2005-09-15 |
CA2558848C true CA2558848C (en) | 2013-11-19 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA2558848A Expired - Lifetime CA2558848C (en) | 2004-03-05 | 2005-03-04 | Isoxazoline-substituted benzamide compound and pesticide |
Country Status (28)
Country | Link |
---|---|
US (11) | US7662972B2 (en, 2012) |
EP (1) | EP1731512B9 (en, 2012) |
JP (2) | JP4883296B2 (en, 2012) |
KR (2) | KR101197482B1 (en, 2012) |
CN (4) | CN102558082B (en, 2012) |
AU (2) | AU2005219788B2 (en, 2012) |
BE (1) | BE2015C014I2 (en, 2012) |
BR (1) | BRPI0508140B1 (en, 2012) |
CA (1) | CA2558848C (en, 2012) |
CY (2) | CY1115818T1 (en, 2012) |
DK (1) | DK1731512T3 (en, 2012) |
EA (2) | EA011764B1 (en, 2012) |
ES (1) | ES2526614T3 (en, 2012) |
FI (1) | FIC20150014I1 (en, 2012) |
FR (1) | FR15C0023I2 (en, 2012) |
HR (1) | HRP20141241T1 (en, 2012) |
HU (1) | HUS1500009I1 (en, 2012) |
IL (1) | IL177949A (en, 2012) |
LT (1) | LTC1731512I2 (en, 2012) |
LU (1) | LU92672I2 (en, 2012) |
NL (1) | NL300721I1 (en, 2012) |
PL (1) | PL1731512T3 (en, 2012) |
PT (1) | PT1731512E (en, 2012) |
RS (1) | RS53639B1 (en, 2012) |
SI (1) | SI1731512T1 (en, 2012) |
TW (1) | TW200536479A (en, 2012) |
WO (1) | WO2005085216A1 (en, 2012) |
ZA (1) | ZA200607637B (en, 2012) |
Families Citing this family (560)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102558082B (zh) | 2004-03-05 | 2015-09-30 | 日产化学工业株式会社 | 异噁唑啉取代苯甲酰胺化合物的制备中间体 |
TW200613272A (en) | 2004-08-13 | 2006-05-01 | Astrazeneca Ab | Isoindolone compounds and their use as metabotropic glutamate receptor potentiators |
WO2007037898A2 (en) * | 2005-08-29 | 2007-04-05 | Housey Pharmaceuticals Inc | Theramutein modulators |
JP5031745B2 (ja) * | 2005-08-12 | 2012-09-26 | アストラゼネカ アクチボラグ | 代謝型グルタミン酸受容体増強性イソインドロン |
US7807706B2 (en) | 2005-08-12 | 2010-10-05 | Astrazeneca Ab | Metabotropic glutamate-receptor-potentiating isoindolones |
US7868008B2 (en) | 2005-08-12 | 2011-01-11 | Astrazeneca Ab | Substituted isoindolones and their use as metabotropic glutamate receptor potentiators |
WO2007026965A1 (ja) | 2005-09-02 | 2007-03-08 | Nissan Chemical Industries, Ltd. | イソキサゾリン置換ベンズアミド化合物及び有害生物防除剤 |
JP5186751B2 (ja) * | 2005-10-14 | 2013-04-24 | 住友化学株式会社 | ヒドラジド化合物およびその有害生物防除用途 |
EP1940849B1 (en) * | 2005-10-21 | 2010-01-27 | Basf Se | Isothiazolopyridin-3-ylenamines for combating animal pests |
EP1965645A2 (en) * | 2005-12-14 | 2008-09-10 | E.I. Du Pont De Nemours And Company | Isoxazolines for controlling invertebrate pests |
TW200803740A (en) | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
ZA200804080B (en) * | 2005-12-16 | 2009-10-28 | Du Pont | 5-Aryl isoxazolines for controlling invertebrate pests |
FR2895605A1 (fr) * | 2005-12-22 | 2007-06-29 | Thomson Licensing Sas | Procede de reception d'un signal a porteuses multiples, procede d'emission, recepteur et emetteur correspondants |
CN101346336B (zh) | 2005-12-26 | 2013-02-27 | 日产化学工业株式会社 | 1,3-二(取代苯基)-3-取代-2-丙烯-1-酮化合物和其盐 |
TWI412322B (zh) * | 2005-12-30 | 2013-10-21 | Du Pont | 控制無脊椎害蟲之異唑啉 |
US7964758B2 (en) * | 2006-02-13 | 2011-06-21 | Nissan Chemical Industries, Ltd. | Process for production of 2-(substituted phenyl)-3,3,3-trifluoropropene compound |
PL1997813T3 (pl) | 2006-03-10 | 2010-10-29 | Nissan Chemical Ind Ltd | Podstawiony związek izoksazolinowy i środek zwalczający szkodniki |
US20070238700A1 (en) * | 2006-04-10 | 2007-10-11 | Winzenberg Kevin N | N-phenyl-1,1,1-trifluoromethanesulfonamide hydrazone derivative compounds and their usage in controlling parasites |
WO2007123855A2 (en) * | 2006-04-20 | 2007-11-01 | E. I. Du Pont De Nemours And Company | Pyrazolines for controlling invertebrate pests |
JPWO2007125984A1 (ja) * | 2006-04-28 | 2009-09-10 | 日本農薬株式会社 | イソキサゾリン誘導体及び有害生物防除剤並びにその使用方法 |
JP2008044880A (ja) | 2006-08-15 | 2008-02-28 | Bayer Cropscience Ag | 殺虫性イソオキサゾリン類 |
JP5164510B2 (ja) * | 2006-10-06 | 2013-03-21 | 日本曹達株式会社 | 含窒素複素環化合物および有害生物防除剤 |
JP2009062352A (ja) * | 2006-10-12 | 2009-03-26 | Nippon Soda Co Ltd | 含窒素複素環化合物および有害生物防除剤 |
JP5164525B2 (ja) * | 2006-11-01 | 2013-03-21 | 日本曹達株式会社 | 含窒素へテロ環化合物および有害生物防除剤 |
EP2151437A4 (en) * | 2007-03-07 | 2012-05-02 | Nissan Chemical Ind Ltd | ISOXAZOLINE SUBSTITUTED BENZAMIDE COMPOUND AND PEST CONTROL AGENT |
JP5256753B2 (ja) * | 2007-03-29 | 2013-08-07 | 住友化学株式会社 | イソオキサゾリン化合物とその有害生物防除用途 |
JP2008260691A (ja) * | 2007-04-10 | 2008-10-30 | Bayer Cropscience Ag | 殺虫性アリールイソオキサゾリン誘導体 |
US8372867B2 (en) * | 2007-04-10 | 2013-02-12 | Bayer Cropscience Ag | Insecticidal aryl isoxazoline derivatives |
US20080262057A1 (en) * | 2007-04-20 | 2008-10-23 | Dow Agrosciences Llc | Diarylisoxazolines |
US9266830B2 (en) | 2007-04-23 | 2016-02-23 | Bayer Intellectual Property Gmbh | Pesticidal arylpyrrolidines |
JP2010116389A (ja) | 2008-10-17 | 2010-05-27 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
JP2008266230A (ja) | 2007-04-23 | 2008-11-06 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
TWI417100B (zh) | 2007-06-07 | 2013-12-01 | Astrazeneca Ab | 二唑衍生物及其作為代謝型麩胺酸受體增效劑-842之用途 |
AU2014277839B2 (en) * | 2007-06-13 | 2017-02-02 | Corteva Agriscience Llc | Isoxazoline insecticides |
JP5473906B2 (ja) * | 2007-06-13 | 2014-04-16 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | イソキサゾリン殺虫剤 |
TWI430995B (zh) | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
AU2013273726B2 (en) * | 2007-06-26 | 2016-04-28 | Corteva Agriscience Llc | Naphthalene isoxazoline invertebrate pest control agents |
AU2016208330A1 (en) * | 2007-06-26 | 2016-08-11 | E. I. Du Pont De Nemours And Company | Naphthalene isoxazoline invertebrate pest control agents |
AU2014259503C1 (en) * | 2007-06-27 | 2019-06-13 | E. I. Du Pont De Nemours And Company | Animal pest control method |
US8952175B2 (en) * | 2007-06-27 | 2015-02-10 | Nissan Chemical Industries, Ltd. | Method for production of 3-hydroxypropan-1-one compound, method for production of 2-propen-1-one compound and method for production of isoxazoline compound |
CN101743000A (zh) * | 2007-06-27 | 2010-06-16 | 杜邦公司 | 动物虫害控制方法 |
JP5316808B2 (ja) * | 2007-06-29 | 2013-10-16 | 日産化学工業株式会社 | 置換イソキサゾリン又はエノンオキシム化合物および有害生物防除剤 |
CN101778833A (zh) | 2007-08-10 | 2010-07-14 | 日本曹达株式会社 | 含氮杂环化合物和有害生物防除剂 |
JP5184057B2 (ja) * | 2007-08-10 | 2013-04-17 | 日本曹達株式会社 | 含窒素複素環化合物および有害生物防除剤 |
TWI461411B (zh) | 2007-08-17 | 2014-11-21 | Du Pont | 製備5-鹵烷基-4,5-二氫異唑衍生物之方法 |
AU2020230282B2 (en) * | 2007-08-17 | 2022-04-07 | Intervet International B.V. | Isoxazoline compositions and their use as antiparasitics |
TWI556741B (zh) | 2007-08-17 | 2016-11-11 | 英特威特國際股份有限公司 | 異唑啉組成物及其作為抗寄生蟲藥上的應用 |
EP2182809B1 (en) * | 2007-08-27 | 2018-01-17 | Dart Neuroscience (Cayman) Ltd | Therapeutic isoxazole compounds |
EP2199287A4 (en) | 2007-09-10 | 2011-04-27 | Nissan Chemical Ind Ltd | SUBSTITUTED ISOXAZOLINE COMPOUND AND AGENT FOR CONTROLLING PESTS |
JP5173335B2 (ja) * | 2007-09-13 | 2013-04-03 | 東ソ−・エフテック株式会社 | (1−パーフルオロアルキル)ビニルアリール類の製造方法 |
US8367584B2 (en) | 2007-10-03 | 2013-02-05 | E.I. Du Pont De Nemours And Company | Naphthalene isoxazoline compounds for control of invertebrate pests |
GB0720232D0 (en) * | 2007-10-16 | 2007-11-28 | Syngenta Participations Ag | Insecticidal compounds |
WO2009063910A1 (ja) * | 2007-11-12 | 2009-05-22 | Nissan Chemical Industries, Ltd. | 光学活性イソキサゾリン化合物の触媒的不斉合成方法 |
TWI356094B (en) * | 2007-11-14 | 2012-01-11 | Ind Tech Res Inst | Liquid crystal compound and liquid crystal display |
WO2009072621A1 (ja) * | 2007-12-07 | 2009-06-11 | Nissan Chemical Industries, Ltd. | 置換ジヒドロアゾール化合物及び有害生物防除剤 |
NZ585883A (en) * | 2007-12-19 | 2011-11-25 | Syngenta Participations Ag | Oxazoline derivatives as insecticidal compounds |
JP5324082B2 (ja) * | 2007-12-20 | 2013-10-23 | 大阪瓦斯株式会社 | 9,9−ビス(カルボキシアリール)フルオレン類およびそのエステルの製造方法 |
TWI411395B (zh) | 2007-12-24 | 2013-10-11 | Syngenta Participations Ag | 殺蟲化合物 |
BRPI0907751A2 (pt) | 2008-02-07 | 2015-07-21 | Bayer Cropscience Ag | Arilpirrolinas inseticidas |
JP2009286773A (ja) * | 2008-03-14 | 2009-12-10 | Bayer Cropscience Ag | 殺虫性縮環式アリール類 |
TWI518076B (zh) | 2008-04-09 | 2016-01-21 | 杜邦股份有限公司 | 製備雜環化合物之方法 |
US7790760B2 (en) | 2008-06-06 | 2010-09-07 | Astrazeneca Ab | Metabotropic glutamate receptor isoxazole ligands and their use as potentiators 286 |
AU2014200736B2 (en) * | 2008-07-09 | 2015-08-20 | Nissan Chemical Corporation | Process for production of isoxazoline-substituted benzoic acid amide compound |
KR20110028538A (ko) * | 2008-07-09 | 2011-03-18 | 바스프 에스이 | 이속사졸린 화합물 ⅱ를 포함하는 살충 혼합물 |
WO2010005048A1 (ja) | 2008-07-09 | 2010-01-14 | 日産化学工業株式会社 | イソキサゾリン置換安息香酸アミド化合物の製造方法 |
US8563474B2 (en) | 2008-07-09 | 2013-10-22 | Basf Se | Pestcidal active mixtures comprising isoxazoline compounds I |
EP2331536B1 (en) | 2008-08-22 | 2013-08-21 | Syngenta Participations AG | Insecticidal compounds |
MX2011001851A (es) | 2008-08-22 | 2011-03-21 | Syngenta Participations Ag | Compuestos insecticidas. |
JP5488835B2 (ja) * | 2008-09-04 | 2014-05-14 | 日産化学工業株式会社 | 置換アセトフェノン化合物、その製造方法及び用途 |
US8686014B2 (en) | 2008-09-04 | 2014-04-01 | Syngenta Limited | Insecticidal compounds |
BRPI0918731A2 (pt) | 2008-09-18 | 2019-09-24 | Nippon Soda Co | composto heterocíclico contendo nitrogênio e agente de controle de pragas |
LT3050874T (lt) | 2008-11-14 | 2019-04-10 | Merial Inc. | Enantiomeriškai praturtinti arilazol-2-ilo cianetilamino paraziticidiniai junginiai |
KR101660068B1 (ko) | 2008-11-19 | 2016-09-26 | 메리얼 인코포레이티드 | 기생충 감염 치료를 위한 1-아릴피라졸 단독 또는 포름아미딘과의 조합을 포함하는 조성물 |
EP2376513B1 (en) | 2008-12-04 | 2015-02-25 | Merial Limited | Dimeric avermectin and milbemycin derivatives |
KR20110098848A (ko) * | 2008-12-23 | 2011-09-01 | 바스프 에스이 | 무척추동물 해충을 퇴치하기 위한 이민 화합물 |
AU2009331664A1 (en) * | 2008-12-23 | 2011-07-14 | Basf Se | Substituted amidine compounds for combating animal pests |
CN102292331A (zh) | 2009-01-22 | 2011-12-21 | 先正达参股股份有限公司 | 杀虫化合物 |
CN102300864A (zh) * | 2009-01-29 | 2011-12-28 | 先正达参股股份有限公司 | 杀虫化合物 |
JP5747440B2 (ja) | 2009-02-06 | 2015-07-15 | 住友化学株式会社 | ヒドラジド化合物及びその有害生物防除用途 |
US8980892B2 (en) | 2009-03-26 | 2015-03-17 | Syngenta Crop Protection Llc | Insecticidal compounds |
BRPI1006543A2 (pt) | 2009-04-01 | 2015-08-25 | Basf Se | "compostos de isoxazolina, composição agrícola, composição veterinária, uso de composto, método para o controle de pragas invertebradas, material de propagação de plantas e método para o tratamento, controle, prevenção ou proteção de animais contra infestação ou infecção por parasitas" |
JP5683569B2 (ja) | 2009-04-28 | 2015-03-11 | ビーエーエスエフ コーポレーション | 発泡性駆除薬組成物 |
MX2011011079A (es) | 2009-04-30 | 2011-11-04 | Basf Se | Procedimiento para preparar compuestos de isoxazolina sustituidos y sus precursores. |
CN102438984A (zh) | 2009-05-19 | 2012-05-02 | 拜耳作物科学公司 | 杀虫用芳基吡咯啉 |
MX2011013448A (es) | 2009-06-22 | 2012-02-13 | Syngenta Participations Ag | Compuestos insecticidas. |
EP2456308A2 (en) | 2009-07-24 | 2012-05-30 | Basf Se | Pyridine derivatives for controlling invertrebate pests |
CN102596968B (zh) | 2009-07-30 | 2015-05-06 | 梅里亚有限公司 | 杀虫的4-氨基-噻吩并[2,3-d]-嘧啶化合物及其使用方法 |
JP5679102B2 (ja) * | 2009-08-03 | 2015-03-04 | 日産化学工業株式会社 | ジヒドロイソキサゾール置換安息香酸化合物の光学活性体とジアステレオマー塩及びその製造方法 |
NZ597597A (en) * | 2009-08-07 | 2014-01-31 | Dow Agrosciences Llc | Pesticidal compositions containing heteroaryl-n-aryl carbamate compounds |
UA108619C2 (xx) * | 2009-08-07 | 2015-05-25 | Пестицидні композиції | |
JP2011057661A (ja) * | 2009-08-14 | 2011-03-24 | Bayer Cropscience Ag | 殺虫性カルボキサミド類 |
CA2771752A1 (en) | 2009-08-28 | 2011-03-03 | Basf Corporation | Foamable pesticide compositions and methods of application |
BR112012006615A2 (pt) | 2009-09-24 | 2019-09-24 | Basf Se | compostos de amnoquinazolina da fórmula i, composição agrícola, composição veterinária, método material de propagação da planta, sementes e uso |
JP2011093855A (ja) | 2009-10-30 | 2011-05-12 | Bayer Cropscience Ag | 殺虫性オキサゾリジノン誘導体 |
WO2011057942A1 (en) | 2009-11-12 | 2011-05-19 | Basf Se | Insecticidal methods using pyridine compounds |
BR112012011808B1 (pt) | 2009-11-17 | 2020-02-04 | Merial Ltd | derivados heteroarilalquilsulfeto oxa tio fluorados para combater pragas invertebradas. |
WO2011064188A1 (en) | 2009-11-27 | 2011-06-03 | Basf Se | Insecticidal methods using nitrogen-containing heteroaromatic compounds |
TWI487486B (zh) | 2009-12-01 | 2015-06-11 | Syngenta Participations Ag | 以異唑啉衍生物為主之殺蟲化合物 |
CA2782902C (en) | 2009-12-04 | 2017-10-17 | Merial Limited | Pesticidal bis-organosulfur compounds |
WO2011069955A1 (en) | 2009-12-07 | 2011-06-16 | Basf Se | Sulfonimidamide compounds for combating animal pests |
PT2513104E (pt) | 2009-12-17 | 2016-06-03 | Merial Inc | Compostos de di-hidroazole antiparasitários e composições que compreendem os mesmos |
US20120291159A1 (en) | 2009-12-18 | 2012-11-15 | Basf Se | Azoline Compounds for Combating Invertebrate Pests |
JP2011136928A (ja) | 2009-12-28 | 2011-07-14 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
ES2546417T3 (es) | 2010-02-01 | 2015-09-23 | Basf Se | Compuestos de isoxazolina cetónica sustituidos y derivados para combatir plagas animales |
US20120295931A1 (en) | 2010-02-05 | 2012-11-22 | Lutz Juergen | Spiroindoline compounds for use as anthelminthics |
EP2536698B1 (en) * | 2010-02-17 | 2015-06-10 | Syngenta Participations AG | Isoxazoline derivatives as insecticides |
MX2012009706A (es) | 2010-02-22 | 2012-09-12 | Syngenta Participations Ag | Derivados de dihidrofurano como compuestos insecticidas. |
WO2011107504A1 (de) | 2010-03-04 | 2011-09-09 | Bayer Cropscience Ag | Fluoralkyl- substituierte 2 -amidobenzimidazole und deren verwendung zur steigerung der stresstoleranz in pflanzen |
WO2011117804A1 (en) | 2010-03-23 | 2011-09-29 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
WO2011117806A2 (en) | 2010-03-23 | 2011-09-29 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
UA108641C2 (uk) | 2010-04-02 | 2015-05-25 | Паразитицидна композиція, яка містить чотири активних агенти, та спосіб її застосування | |
EP2556060A1 (en) | 2010-04-08 | 2013-02-13 | Ah Usa 42 Llc | Substituted 3,5- diphenyl-isoxazoline derivatives as insecticides and acaricides |
ES2494716T3 (es) | 2010-05-05 | 2014-09-16 | Bayer Intellectual Property Gmbh | Derivados de Tiazol como pesticidas |
WO2011148886A1 (ja) | 2010-05-24 | 2011-12-01 | Meiji Seikaファルマ株式会社 | 有害生物防除剤 |
UA108881C2 (xx) | 2010-05-27 | 2015-06-25 | Кристалічна форма 4-$5-$3-хлор-5-(трифторметил)феніл]-4,5-дигідро-5-(трифторметил)-3-ізоксазоліл]-n-$2-оксо-2-$(2,2,2-трифторетил)аміно]етил]-1-нафталінкарбоксаміду | |
TWI584734B (zh) | 2010-05-28 | 2017-06-01 | 巴地斯顏料化工廠 | 農藥混合物 |
US20130210623A1 (en) | 2010-06-09 | 2013-08-15 | Syngenta Crop Protection Llc | Pesticidal mixtures including isoxazoline derivatives |
AR081843A1 (es) | 2010-06-09 | 2012-10-24 | Syngenta Participations Ag | Mezclas pesticidas incluyendo derivados isoxazolina |
UY33403A (es) * | 2010-06-17 | 2011-12-30 | Novartis Ag | Compuestos orgánicos con novedosas isoxazolinas, sus n-óxidos, s-óxidos y sales |
WO2011157778A1 (de) | 2010-06-18 | 2011-12-22 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden eigenschaften |
DK178277B1 (da) | 2010-06-18 | 2015-10-26 | Novartis Tiergesundheit Ag | Diaryloxazolinforbindelser til bekæmpelse af fiskelus |
MX2012014439A (es) | 2010-06-23 | 2013-02-07 | Basf Se | Proceso para producir compuestos aromaticos de carbonilo e imina. |
WO2012000896A2 (de) | 2010-06-28 | 2012-01-05 | Bayer Cropscience Ag | Heterocyclische verbindungen als schädlingsbekämpfungsmittel |
JP2012017289A (ja) | 2010-07-08 | 2012-01-26 | Bayer Cropscience Ag | 殺虫性ピロリン誘導体 |
WO2012004293A2 (de) | 2010-07-08 | 2012-01-12 | Bayer Cropscience Ag | Insektizide und fungizide wirkstoffkombinationen |
WO2012007426A1 (en) | 2010-07-13 | 2012-01-19 | Basf Se | Azoline substituted isoxazoline benzamide compounds for combating animal pests |
US9247745B2 (en) | 2010-07-22 | 2016-02-02 | Basf Se | Substituted pyridazines for controlling invertebrate pests |
CN103097376A (zh) | 2010-09-13 | 2013-05-08 | 巴斯夫欧洲公司 | 用于防治无脊椎动物害虫的吡啶化合物ii |
BR112013005382B1 (pt) | 2010-09-13 | 2020-02-18 | Basf Se | Uso de um composto 3-piridila, método para controlar pragas invertebradas, método para proteger o material de propagação vegetal e/ou plantas e composição agrícola |
JP2013537178A (ja) | 2010-09-13 | 2013-09-30 | ビーエーエスエフ ソシエタス・ヨーロピア | 無脊椎有害生物iiiを防除するためのピリジン化合物 |
JP2012062267A (ja) | 2010-09-15 | 2012-03-29 | Bayer Cropscience Ag | 殺虫性ピロリンn−オキサイド誘導体 |
JP2012082186A (ja) | 2010-09-15 | 2012-04-26 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
BR112013006686A2 (pt) | 2010-09-24 | 2017-11-14 | Zoetis Llc | isoxazolina oximas como agentes antiparasitários |
PL2621923T3 (pl) | 2010-09-29 | 2017-08-31 | Intervet International B.V. | Związki n-heteroarylu z mostkami cyklicznymi do leczenia chorób pasożytniczych |
CN103189356B (zh) | 2010-09-29 | 2015-11-25 | 英特维特国际股份有限公司 | N-杂芳基化合物 |
WO2012042006A1 (en) | 2010-10-01 | 2012-04-05 | Basf Se | Imine compounds |
EP2621900A1 (en) | 2010-10-01 | 2013-08-07 | Basf Se | Imine substituted 2, 4 - diaryl - pyrroline derivatives as pesticides |
WO2012045680A2 (de) | 2010-10-04 | 2012-04-12 | Bayer Cropscience Ag | Insektizide und fungizide wirkstoffkombinationen |
RU2013123057A (ru) | 2010-10-21 | 2014-11-27 | Байер Интеллекчуал Проперти Гмбх | N-бензил гетероциклические карбоксамиды |
BR112013010683B1 (pt) | 2010-11-02 | 2018-06-26 | Bayer Intellectual Property Gmbh | Composto, composição fungicida e método para controlar fungos fitopatogênicos de safras |
CN103282345A (zh) | 2010-11-03 | 2013-09-04 | 巴斯夫欧洲公司 | 制备取代的异噁唑啉化合物及其前体4-氯-、4-溴-或4-碘苯甲醛肟的方法 |
JP2014015397A (ja) * | 2010-11-04 | 2014-01-30 | Nippon Soda Co Ltd | 動物用外部寄生虫防除剤 |
CN103313971B (zh) | 2010-11-15 | 2015-12-02 | 拜耳知识产权有限责任公司 | N-芳基吡唑(硫代)甲酰胺 |
JP2014028758A (ja) * | 2010-11-19 | 2014-02-13 | Nissan Chem Ind Ltd | 寄生虫及び衛生害虫防除剤 |
PH12013501087A1 (en) | 2010-11-29 | 2022-05-18 | Bayer Ip Gmbh | Alpha, beta-unsaturated imines |
JP6412311B2 (ja) | 2010-12-01 | 2018-10-24 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH | 作物において線虫類を防除するための、及び、収量を増加させるための、フルオピラムの使用 |
US20130253012A1 (en) | 2010-12-10 | 2013-09-26 | Basf Se | Pyrazole Compounds for Controlling Invertebrate Pests |
TWI667347B (zh) | 2010-12-15 | 2019-08-01 | 瑞士商先正達合夥公司 | 大豆品種syht0h2及偵測其之組合物及方法 |
WO2012084670A1 (en) | 2010-12-20 | 2012-06-28 | Basf Se | Pesticidal active mixtures comprising pyrazole compounds |
DE102010063691A1 (de) | 2010-12-21 | 2012-06-21 | Bayer Animal Health Gmbh | Ektoparasitizide Wirkstoffkombinationen |
WO2012085081A1 (en) | 2010-12-22 | 2012-06-28 | Basf Se | Sulfoximinamide compounds for combating invertebrate pests ii |
PT2658542T (pt) | 2010-12-27 | 2022-03-10 | Intervet Int Bv | Formulação de isoxazolina localizada tópica |
KR101920476B1 (ko) | 2010-12-27 | 2018-11-21 | 인터벳 인터내셔널 비.브이. | 글리코푸롤을 포함하는 국소 적용 이속사졸린 제제 |
EP2471363A1 (de) | 2010-12-30 | 2012-07-04 | Bayer CropScience AG | Verwendung von Aryl-, Heteroaryl- und Benzylsulfonamidocarbonsäuren, -carbonsäureestern, -carbonsäureamiden und -carbonitrilen oder deren Salze zur Steigerung der Stresstoleranz in Pflanzen |
UY33887A (es) * | 2011-02-03 | 2012-09-28 | Syngenta Ltd | Métodos de control de plagas en la soja |
WO2012110519A1 (de) | 2011-02-17 | 2012-08-23 | Bayer Cropscience Ag | Substituierte 3-(biphenyl-3-yl)-8,8-difluor-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one zur therapie und halogensubstituierte spirocyclische ketoenole |
MX347939B (es) | 2011-02-17 | 2017-05-19 | Bayer Ip Gmbh | Uso de funguicidas sdhi en variedades de soja de cultivo selectivo convencional, tolerantes a asr, resistentes a la cancrosis del tallo y/o resistentes a la mancha de hoja "ojo de rana". |
US9510594B2 (en) | 2011-02-17 | 2016-12-06 | Bayer Intellectual Property Gmbh | Use of SDHI fungicides on conventionally bred ASR-tolerant, stem canker resistant and/or frog-eye leaf spot resistant soybean varieties |
CA2828639C (en) | 2011-03-01 | 2019-02-12 | Bayer Intellectual Property Gmbh | 2-acyloxypyrrolin-4-ones |
AR085509A1 (es) | 2011-03-09 | 2013-10-09 | Bayer Cropscience Ag | Indol- y bencimidazolcarboxamidas como insecticidas y acaricidas |
CA2823999C (en) | 2011-03-10 | 2020-03-24 | Bayer Intellectual Property Gmbh | Use of lipochito-oligosaccharide compounds for safeguarding seed safety of treated seeds |
ES2585555T3 (es) * | 2011-03-10 | 2016-10-06 | Zoetis Services Llc | Derivados espirocíclicos de isoxazolina como agentes antiparasitarios |
BR112013023924A2 (pt) | 2011-03-18 | 2016-08-09 | Bayer Ip Gmbh | novos compostos substituídos com halogênio |
CN103582639A (zh) | 2011-04-06 | 2014-02-12 | 巴斯夫欧洲公司 | 用于防治动物害虫的取代嘧啶鎓化合物 |
AR085872A1 (es) | 2011-04-08 | 2013-10-30 | Basf Se | Derivados heterobiciclicos n-sustituidos utiles para combatir parasitos en plantas y/o animales, composiciones que los contienen y metodos para combatir dichas plagas |
AR090010A1 (es) | 2011-04-15 | 2014-10-15 | Bayer Cropscience Ag | 5-(ciclohex-2-en-1-il)-penta-2,4-dienos y 5-(ciclohex-2-en-1-il)-pent-2-en-4-inos sustituidos como principios activos contra el estres abiotico de las plantas, usos y metodos de tratamiento |
AR085585A1 (es) | 2011-04-15 | 2013-10-09 | Bayer Cropscience Ag | Vinil- y alquinilciclohexanoles sustituidos como principios activos contra estres abiotico de plantas |
AR085568A1 (es) | 2011-04-15 | 2013-10-09 | Bayer Cropscience Ag | 5-(biciclo[4.1.0]hept-3-en-2-il)-penta-2,4-dienos y 5-(biciclo[4.1.0]hept-3-en-2-il)-pent-2-en-4-inos sustituidos como principios activos contra el estres abiotico de las plantas |
HRP20160639T4 (hr) | 2011-04-21 | 2024-09-27 | Basf Se | Novi pesticidni spojevi na bazi pirazola |
AR086113A1 (es) * | 2011-04-30 | 2013-11-20 | Abbott Lab | Isoxazolinas como agentes terapeuticos |
CA2834164A1 (en) | 2011-05-10 | 2012-11-15 | Gilead Sciences, Inc. | Fused benzoxazinones as ion channel modulators |
KR20140034798A (ko) * | 2011-05-18 | 2014-03-20 | 신젠타 파티서페이션즈 아게 | 아릴티오아세트아미드 유도체에 기반한 살곤충 화합물 |
WO2012155352A1 (en) * | 2011-05-19 | 2012-11-22 | Eli Lilly And Company | Dihydroisoxazole compounds, parasiticidal uses and formulations thereof |
TWI555471B (zh) | 2011-05-31 | 2016-11-01 | 先正達合夥公司 | 包含異唑啉衍生物之殺有害生物混合物 |
BR112013030572A2 (pt) * | 2011-05-31 | 2016-08-16 | Syngenta Participations Ag | misturas pesticidas compreendendo derivados de isoxazolina |
US9339505B2 (en) | 2011-05-31 | 2016-05-17 | Syngenta Participations Ag | Pesticidal mixtures including isoxazoline derivatives |
UY34104A (es) | 2011-05-31 | 2013-01-03 | Syngenta Participations Ag | ?compuestos derivados benzamídicos heterocíclicos, procesos e intermedios para su preparación, composiciones y métodos para su uso?. |
EP2535334A1 (de) | 2011-06-17 | 2012-12-19 | Bayer CropScience AG | Kristalline Modifikationen von Penflufen |
CN106165684B (zh) * | 2011-06-24 | 2019-06-14 | 陶氏益农公司 | 杀虫组合物及其相关方法 |
WO2013003505A1 (en) | 2011-06-27 | 2013-01-03 | Merial Limited | Amido-pyridyl ether compounds and compositions and their use against parasites |
EP2540163A1 (en) | 2011-06-30 | 2013-01-02 | Bayer CropScience AG | Nematocide N-cyclopropyl-sulfonylamide derivatives |
TW201837023A (zh) | 2011-07-01 | 2018-10-16 | 美商基利科學股份有限公司 | 作為離子通道調節劑之稠合雜環化合物 |
NO3175985T3 (en, 2012) | 2011-07-01 | 2018-04-28 | ||
JP2014520776A (ja) | 2011-07-04 | 2014-08-25 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | 植物における非生物的ストレスに対する活性薬剤としての置換されているイソキノリノン類、イソキノリンジオン類、イソキノリントリオン類およびジヒドロイソキノリノン類または各場合でのそれらの塩の使用 |
KR20140045542A (ko) * | 2011-07-12 | 2014-04-16 | 다우 아그로사이언시즈 엘엘씨 | 살충 조성물 및 그에 관한 방법 |
KR20140048257A (ko) | 2011-07-15 | 2014-04-23 | 바스프 에스이 | 동물 해충을 퇴치하기 위해 치환된 3-피리딜 티아졸 화합물 및 유도체 i을 사용하는 살충 방법 |
DK2736327T3 (en) | 2011-07-26 | 2018-04-23 | Clariant Int Ltd | Etherized lactate esters, processes for their preparation and their use in improving the action of plant protection products |
AU2012288866B2 (en) | 2011-07-27 | 2016-06-16 | Bayer Cropscience Aktiengesellschaft | Seed dressing for controlling phytopathogenic fungi |
WO2013017678A1 (en) | 2011-08-04 | 2013-02-07 | Intervet International B.V. | Novel spiroindoline compounds |
EP2742036A1 (en) | 2011-08-12 | 2014-06-18 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
CN103842336B (zh) | 2011-08-12 | 2017-05-31 | 巴斯夫欧洲公司 | 苯胺类型化合物 |
WO2013024006A1 (en) | 2011-08-12 | 2013-02-21 | Basf Se | Anthranilamide compounds and their use as pesticides |
CN103857666B (zh) | 2011-08-12 | 2016-12-14 | 巴斯夫欧洲公司 | N-硫代邻氨基苯甲酰胺化合物及其作为农药的用途 |
WO2013024004A1 (en) | 2011-08-12 | 2013-02-21 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
CN103842342A (zh) | 2011-08-12 | 2014-06-04 | 巴斯夫欧洲公司 | 邻氨基苯甲酰胺化合物及其作为农药的用途 |
EP2742023A1 (en) | 2011-08-12 | 2014-06-18 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
WO2013024171A1 (en) | 2011-08-18 | 2013-02-21 | Basf Se | Carbamoylmethoxy- and carbamoylmethylthio- and carbamoylmethylamino benzamides for combating invertebrate pests |
WO2013024170A1 (en) | 2011-08-18 | 2013-02-21 | Basf Se | Carbamoylmethoxy- and carbamoylmethylthio- and carbamoylmethylamino benzamides for combating invertebrate pests |
WO2013024169A1 (en) | 2011-08-18 | 2013-02-21 | Basf Se | Carbamoylmethoxy- and carbamoylmethylthio- and carbamoylmethylamino benzamides for combating invertebrate pests |
US20140343049A1 (en) | 2011-08-22 | 2014-11-20 | Syngenta Participations Ag | Dihydrofuran derivatives as insecticidal compounds |
EP2748137A1 (en) | 2011-08-22 | 2014-07-02 | Syngenta Participations AG | Dihydrofuran derivatives as insecticidal compounds |
WO2013026695A1 (en) | 2011-08-25 | 2013-02-28 | Syngenta Participations Ag | Isoxazoline derivatives as insecticidal compounds |
JP2014524459A (ja) | 2011-08-25 | 2014-09-22 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | シロアリおよびアリの防除方法 |
CN103764644A (zh) * | 2011-08-25 | 2014-04-30 | 先正达参股股份有限公司 | 作为杀虫化合物的异噁唑啉衍生物 |
EP2561759A1 (en) | 2011-08-26 | 2013-02-27 | Bayer Cropscience AG | Fluoroalkyl-substituted 2-amidobenzimidazoles and their effect on plant growth |
WO2013030262A1 (en) | 2011-09-02 | 2013-03-07 | Basf Se | Insecticidal active mixtures comprising arylquinazolinone compounds |
BR112014004567A2 (pt) | 2011-09-02 | 2017-04-04 | Basf Se | uso de composto, método de proteção de plantas contra o ataque ou infestação por insetos, araquinídeos ou nemátodos, método para o controle ou combate de insetos, araquinídeos ou nemátodos, método para proteção de material de propagação de planta e sementes |
CN103957701B (zh) | 2011-09-12 | 2017-05-03 | 梅里亚有限公司 | 包含异噁唑啉活性剂的杀寄生物组合物,其方法和用途 |
EP3190110B1 (en) | 2011-09-13 | 2020-01-08 | Syngenta Participations AG | Isothiazoline derivatives as insecticidal compounds |
UA114093C2 (xx) | 2011-09-16 | 2017-04-25 | Спосіб збільшення врожаю корисних рослин | |
CN103929956B (zh) | 2011-09-16 | 2017-02-22 | 拜耳知识产权有限责任公司 | 酰基磺酰胺用于改善植物产量的用途 |
MX357718B (es) | 2011-09-16 | 2018-07-20 | Bayer Ip Gmbh | Uso de 5-fenil- o 5-bencil-2-isoxazolin-3-carboxilatos para mejorar el rendimiento de las plantas. |
JP2013082632A (ja) | 2011-10-05 | 2013-05-09 | Bayer Cropscience Ag | 農薬製剤及びその製造方法 |
WO2013057624A1 (en) | 2011-10-19 | 2013-04-25 | Ah Usa 42 Llc | Use of aminoacetonitrile derivatives against endoparasites |
US9126995B2 (en) | 2011-11-08 | 2015-09-08 | Nissan Chemical Industries, Ltd. | Method for catalytic asymmetric synthesis of optically active isoxazoline compound and optically active isoxazoline compound |
ES2642715T3 (es) | 2011-11-17 | 2017-11-17 | Merial, Inc. | Composiciones que comprenden un aril pirazol y un imidazol sustituido, procedimientos y utilizaciones de las mismas |
AR088669A1 (es) * | 2011-11-21 | 2014-06-25 | Lilly Co Eli | Derivados de dihidrodibenzo[c][1,2]oxaborol y dihidroisoxazol utiles para el control de ectoparasitos |
CA2856476A1 (en) * | 2011-11-29 | 2013-06-06 | Novartis Ag | Use of aryl derivatives for controlling ectoparasites |
WO2013079601A1 (en) | 2011-12-02 | 2013-06-06 | Basf Se | Method and system for monitoring crops and/or infestation of crops with harmful organismus during storage |
WO2013079600A1 (en) | 2011-12-02 | 2013-06-06 | Basf Se | Method and system for monitoring crops during storage |
ES2659159T3 (es) | 2011-12-02 | 2018-03-14 | Merial, Inc. | Formulaciones de moxidectina inyectable de acción prolongada y nuevas formas cristalinas de moxidectina |
EP2604118A1 (en) | 2011-12-15 | 2013-06-19 | Bayer CropScience AG | Active ingredient combinations having insecticidal and acaricidal properties |
IN2014CN04325A (en, 2012) | 2011-12-19 | 2015-09-04 | Bayer Cropscience Ag | |
WO2013092522A1 (de) | 2011-12-20 | 2013-06-27 | Bayer Intellectual Property Gmbh | Neue insektizide aromatische amide |
CN104023724A (zh) | 2011-12-21 | 2014-09-03 | 巴斯夫欧洲公司 | N-硫代邻氨基苯甲酰胺化合物及其作为农药的用途 |
EP2606726A1 (de) | 2011-12-21 | 2013-06-26 | Bayer CropScience AG | N-Arylamidine-substituierte trifluoroethylsulfid-Derivate als Akarizide und Insektizide |
JP6415983B2 (ja) | 2011-12-23 | 2018-10-31 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 無脊椎有害生物を駆除するためのイソチアゾリン化合物 |
EP2804480A1 (en) | 2012-01-21 | 2014-11-26 | Bayer Intellectual Property GmbH | Use of host defense inducers for controlling bacterial harmful organisms in useful plants |
WO2013113789A1 (en) | 2012-02-02 | 2013-08-08 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
RS58771B1 (sr) | 2012-02-06 | 2019-06-28 | Boehringer Ingelheim Animal Health Usa Inc | Paraziticidne oralne veterinarske kompozicije koje sadrže sistemski-delujuća aktivna sredstva, metodi i primene istih |
JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
WO2013135674A1 (en) | 2012-03-12 | 2013-09-19 | Syngenta Participations Ag | Insecticidal 2-aryl-acetamide compounds |
EP2825532A1 (en) | 2012-03-14 | 2015-01-21 | Bayer Intellectual Property GmbH | Pesticidal arylpyrrolidines |
US9487523B2 (en) | 2012-03-14 | 2016-11-08 | Merck Sharp & Dohme Corp. | Process for making CGRP receptor antagonists |
AU2013241853B2 (en) | 2012-03-28 | 2017-11-09 | Intervet International B.V. | Heteroaryl compounds with A-cyclic bridging unit |
WO2013144180A1 (en) | 2012-03-28 | 2013-10-03 | Intervet International B.V. | Heteroaryl compounds with cyclic bridging unit for use in the treatment helminth infection |
WO2013144228A1 (en) | 2012-03-29 | 2013-10-03 | Basf Se | Pesticidal methods using heterocyclic compounds and derivatives for combating animal pests |
WO2013144223A1 (en) | 2012-03-30 | 2013-10-03 | Basf Se | N-substituted pyrimidinylidene compounds and derivatives for combating animal pests |
ES2626360T3 (es) | 2012-03-30 | 2017-07-24 | Basf Se | Compuestos de piridinilideno tiocarbonilo N-sustituidos y su uso para combatir plagas de animales |
WO2013149940A1 (en) | 2012-04-02 | 2013-10-10 | Basf Se | Acrylamide compounds for combating invertebrate pests |
US20150065501A1 (en) | 2012-04-03 | 2015-03-05 | Basf Se | N-substituted hetero-bicyclic furanone derivatives for combating animal |
JP6148724B2 (ja) | 2012-04-04 | 2017-06-14 | インターベット インターナショナル ベー. フェー. | ソフトなチュアブル医薬製品 |
WO2013150115A1 (en) | 2012-04-05 | 2013-10-10 | Basf Se | N- substituted hetero - bicyclic compounds and derivatives for combating animal pests |
PT2895465T (pt) | 2012-04-20 | 2019-01-16 | Boehringer Ingelheim Animal Health Usa Inc | Composições parasiticidas compreendendo derivados de benzimidazoles, os seus métodos e as suas utilizações |
US9174967B2 (en) | 2012-05-04 | 2015-11-03 | Basf Se | Substituted pyrazole-containing compounds and their use as pesticides |
WO2013167633A1 (en) | 2012-05-09 | 2013-11-14 | Basf Se | Acrylamide compounds for combating invertebrate pests |
WO2013171199A1 (de) | 2012-05-16 | 2013-11-21 | Bayer Cropscience Ag | Insektizide wasser-in-öl (w/o) formulierung |
EP2849562B1 (de) | 2012-05-16 | 2019-03-06 | Bayer CropScience AG | Insektizide öl-in-wasser (o/w) formulierung |
AR091104A1 (es) | 2012-05-22 | 2015-01-14 | Bayer Cropscience Ag | Combinaciones de compuestos activos que comprenden un derivado lipo-quitooligosacarido y un compuesto nematicida, insecticida o fungicida |
ES2656543T3 (es) | 2012-05-24 | 2018-02-27 | Basf Se | Compuestos de N-tio-antranilamida y su uso como pesticidas |
BR112014029759A2 (pt) | 2012-05-30 | 2017-06-27 | Clariant Finance Bvi Ltd | uso de n-metil-n-acilglucaminas como solubilizadores |
BR112014029906A2 (pt) | 2012-05-30 | 2018-04-17 | Bayer Cropscience Ag | composições compreendendo um agente de controle biológico e um inseticida. |
MX362859B (es) | 2012-05-30 | 2019-02-20 | Bayer Cropscience Ag | Composiciones que comprenden un agente de control biologico y un insecticida. |
IN2014DN09937A (en, 2012) | 2012-05-30 | 2015-08-14 | Clariant Int Ltd | |
US20150166528A1 (en) | 2012-06-14 | 2015-06-18 | Basf Se | Pesticidal methods using substituted 3-pyridyl thiazole compounds and derivatives for combating animal pests |
PT3300602T (pt) | 2012-06-20 | 2020-06-17 | Basf Se | Misturas pesticidas que compreendem um composto de pirazol |
WO2014001120A1 (en) | 2012-06-25 | 2014-01-03 | Syngenta Participations Ag | Isothiazole derivatives as insecticidal compounds |
WO2014001121A1 (en) | 2012-06-25 | 2014-01-03 | Syngenta Participations Ag | Isothiazole derivatives as insecticidal compounds |
WO2014005982A1 (de) | 2012-07-05 | 2014-01-09 | Bayer Cropscience Ag | Insektizide und fungizide wirkstoffkombinationen |
EP2684879A1 (en) | 2012-07-09 | 2014-01-15 | Basf Se | Substituted mesoionic compounds for combating animal pests |
MX372801B (es) | 2012-07-31 | 2020-07-03 | Bayer Cropscience Ag | Composicion que comprende una mezcla de terpenos plaguicida y un insecticida. |
US9867375B2 (en) | 2012-07-31 | 2018-01-16 | Syngenta Participations Ag | Methods of pest control in soybean |
BR112015001931A2 (pt) * | 2012-08-03 | 2017-07-04 | Syngenta Participations Ag | métodos de controle de pragas em soja |
WO2014019957A2 (en) | 2012-08-03 | 2014-02-06 | Syngenta Participations Ag | Methods of pest control in soybean |
BR112015002375A2 (pt) | 2012-08-03 | 2017-07-04 | Syngenta Participations Ag | métodos de controle de insetos |
CA2881995A1 (en) | 2012-08-17 | 2014-02-20 | Bayer Cropscience Ag | Azaindole carboxylic acid amides and azaindole thiocarboxylic acid amides for use as insecticides and acaricides |
US9474279B2 (en) * | 2012-08-24 | 2016-10-25 | Syngenta Participations Ag | Methods of controlling insects |
AU2013305089B2 (en) | 2012-08-24 | 2016-11-10 | Syngenta Participations Ag | Methods of controlling insects |
WO2014029639A1 (en) | 2012-08-24 | 2014-02-27 | Syngenta Participations Ag | Methods of soil pest control |
JP2015532650A (ja) | 2012-09-05 | 2015-11-12 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 非生物的植物ストレスに対する活性物質としての置換された2−アミドベンズイミダゾール類、2−アミドベンゾオキサゾール類および2−アミドベンゾチアゾール類またはそれらの塩の使用 |
HK1210472A1 (en) * | 2012-09-07 | 2016-04-22 | Zoetis Services Llc | Spirocyclic derivatives as antiparasitic agents |
CA2882546A1 (en) * | 2012-09-07 | 2014-03-13 | Zoetis Llc | Spirocyclic isoxazolines as antiparasitic agents |
BR112015006299A2 (pt) | 2012-09-21 | 2017-07-04 | Basf Se | ''composto, composição agrícola, método para a proteção dos vegetais de cultura, método para a proteção do material de propagação dos vegetais e material de propagação'' |
US10104892B2 (en) * | 2012-09-25 | 2018-10-23 | Bayer Cropscience Ag | Herbicidally and fungicidally active 3-heteroaryl-isoxazoline-5-carboxamides and 3-heteroaryl-isoxazoline-5-thioamides |
WO2014053407A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
EP2903434A1 (en) | 2012-10-01 | 2015-08-12 | Basf Se | Pesticidal mixtures comprising jasmonic acid or a derivative thereof |
AR093772A1 (es) | 2012-10-01 | 2015-06-24 | Basf Se | Metodo para controlar insectos resistentes a insecticidas moduladores de rianodina |
AR093771A1 (es) | 2012-10-01 | 2015-06-24 | Basf Se | Metodo para controlar insectos resistentes a insecticidas |
BR112015004074A2 (pt) | 2012-10-01 | 2017-07-04 | Basf Se | método para controlar pragas, uso e semente de uma planta cultivada. |
WO2014053404A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Pesticidally active mixtures comprising anthranilamide compounds |
AR093828A1 (es) | 2012-10-01 | 2015-06-24 | Basf Se | Mezclas activas como plaguicidas, que comprenden compuestos de antranilamida |
WO2014053401A2 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of improving plant health |
CN108477173B (zh) | 2012-10-02 | 2021-07-02 | 拜耳农作物科学股份公司 | 作为杀虫剂的杂环化合物 |
WO2014060381A1 (de) | 2012-10-18 | 2014-04-24 | Bayer Cropscience Ag | Heterocyclische verbindungen als schädlingsbekämpfungsmittel |
CN102911131B (zh) * | 2012-10-24 | 2014-10-29 | 中化蓝天集团有限公司 | 一种双键桥三氟甲基异噁唑类化合物、其制备方法及应用 |
EP2914587A1 (de) | 2012-10-31 | 2015-09-09 | Bayer CropScience AG | Neue heterocylische verbindungen als schädlingsbekämpfungsmittel |
AU2013245478A1 (en) | 2012-11-01 | 2014-05-15 | Sumitomo Chemical Company, Limited | Method for administering agent for controlling ectoparasite to dog |
DE102012021647A1 (de) | 2012-11-03 | 2014-05-08 | Clariant International Ltd. | Wässrige Adjuvant-Zusammensetzungen |
UA117816C2 (uk) | 2012-11-06 | 2018-10-10 | Байєр Кропсайєнс Акцієнгезелльшафт | Гербіцидна комбінація для толерантних соєвих культур |
AR093396A1 (es) * | 2012-11-09 | 2015-06-03 | Syngenta Participations Ag | Derivados de dihidrotiofeno como compuestos insecticidas |
ES2893777T3 (es) | 2012-11-20 | 2022-02-10 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos y composiciones antihelmínticas y procedimiento de utilización de los mismos |
US9532946B2 (en) * | 2012-11-20 | 2017-01-03 | Intervet Inc. | Manufacturing of semi-plastic pharmaceutical dosage units |
WO2014079935A1 (en) * | 2012-11-21 | 2014-05-30 | Syngenta Participations Ag | Insecticidal compounds based on arylthioacetamide derivatives |
ES2785070T3 (es) | 2012-11-22 | 2020-10-05 | Basf Corp | Mezclas de pesticidas |
WO2014079841A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079728A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079772A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
EP2922395B1 (en) | 2012-11-22 | 2019-06-05 | BASF Corporation | Pesticidal mixtures |
WO2014079804A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079774A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
AU2013349881B2 (en) | 2012-11-22 | 2017-04-06 | Basf Corporation | Pesticidal mixtures |
WO2014079820A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Use of anthranilamide compounds for reducing insect-vectored viral infections |
WO2014079766A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079770A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079813A1 (en) | 2012-11-23 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079752A1 (en) | 2012-11-23 | 2014-05-30 | Basf Se | Pesticidal mixtures |
EP2925136A2 (en) | 2012-11-30 | 2015-10-07 | Bayer CropScience AG | Binary fungicidal mixtures |
WO2014083033A1 (en) | 2012-11-30 | 2014-06-05 | Bayer Cropsience Ag | Binary fungicidal or pesticidal mixture |
EP2925142B1 (en) | 2012-12-03 | 2018-01-31 | Bayer CropScience AG | Composition comprising a biological control agent and an insecticide |
MX2015006946A (es) | 2012-12-03 | 2015-09-08 | Bayer Cropscience Ag | Composicion que comprende agentes de control biologico. |
WO2014086753A2 (en) | 2012-12-03 | 2014-06-12 | Bayer Cropscience Ag | Composition comprising biological control agents |
WO2014086758A2 (en) | 2012-12-03 | 2014-06-12 | Bayer Cropscience Ag | Composition comprising a biological control agent and an insecticide |
CN105025721A (zh) | 2012-12-03 | 2015-11-04 | 拜耳作物科学股份公司 | 包含生物防治剂和杀虫剂的组合物 |
CN105072903A (zh) | 2012-12-05 | 2015-11-18 | 拜耳作物科学股份公司 | 取代的1-(芳基乙炔基)-环己醇、1-(杂芳基乙炔基)-环己醇、1-(杂环基乙炔基)-环己醇和1-(环烯基乙炔基)-环己醇用作抵抗非生物植物胁迫的活性剂的用途 |
WO2014090765A1 (en) | 2012-12-12 | 2014-06-19 | Bayer Cropscience Ag | Use of 1-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-5-amino-3-trifluoromethyl)-1 h-1,2,4 tfia zole for controlling nematodes in nematode-resistant crops |
WO2014090918A1 (en) | 2012-12-13 | 2014-06-19 | Novartis Ag | Process for the enantiomeric enrichment of diaryloxazoline derivatives |
US10117430B2 (en) | 2012-12-14 | 2018-11-06 | Basf Se | Malononitrile compounds for controlling animal pests |
AR093996A1 (es) | 2012-12-18 | 2015-07-01 | Bayer Cropscience Ag | Combinaciones bactericidas y fungicidas binarias |
CN105007739A (zh) | 2012-12-21 | 2015-10-28 | 巴斯夫欧洲公司 | 用于防治无脊椎动物害虫的环棒麦角素及其衍生物 |
EP2938611A1 (en) | 2012-12-27 | 2015-11-04 | Basf Se | 2-(pyridin-3-yl)-5-hetaryl-thiazole compounds carrying an imine or imine-derived substituent for combating invertebrate pests |
EP2948439B1 (en) | 2013-01-23 | 2020-06-03 | Syngenta Participations AG | Pyrazoline derivatives as insecticidal compounds |
AU2014214140B2 (en) | 2013-02-06 | 2017-08-31 | Vetoquinol Sa | Halogen-substituted pyrazol derivatives as pest-control agents |
MX2015010313A (es) | 2013-02-11 | 2015-11-18 | Bayer Cropscience Lp | Composiciones que comprenden gougerotina y por lo menos un agente de control biologico. |
WO2014124373A1 (en) | 2013-02-11 | 2014-08-14 | Bayer Cropscience Lp | Compositions comprising gougerotin and an insecticide |
WO2014128136A1 (en) | 2013-02-20 | 2014-08-28 | Basf Se | Anthranilamide compounds and their use as pesticides |
WO2014131837A1 (en) | 2013-02-28 | 2014-09-04 | Syngenta Participations Ag | Isoxaline derivatives for use in cotton plants |
WO2014135095A1 (en) * | 2013-03-06 | 2014-09-12 | Syngenta Participations Ag | Dihydrobenzofuran derivatives as insecticidal compounds |
WO2014139897A1 (en) | 2013-03-12 | 2014-09-18 | Bayer Cropscience Ag | Use of dithiine-tetracarboximides for controlling bacterial harmful organisms in useful plants |
KR20150144779A (ko) | 2013-04-19 | 2015-12-28 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 살충성 또는 농약성 2성분 혼합물 |
CN105324031B (zh) | 2013-04-19 | 2018-11-13 | 拜耳作物科学股份公司 | 具有杀虫特性的活性化合物结合物 |
BR112015026357A2 (pt) | 2013-04-19 | 2017-07-25 | Basf Se | compostos, composição agrícola ou veterinária, métodos para o combate ou controle das pragas, para a proteção de vegetais, para a proteção do material de propagação e para o tratamento de animais e utilização de um composto |
CN104163791B (zh) * | 2013-05-20 | 2017-05-03 | 湖南化工研究院 | N‑吡啶(杂)芳酰胺类化合物及其制备方法与应用 |
EP3010893B1 (de) | 2013-06-20 | 2019-10-02 | Bayer CropScience Aktiengesellschaft | Arylsulfid- und arylsulfoxid-derivate als akarizide und insektizide |
ES2712211T3 (es) | 2013-06-20 | 2019-05-09 | Bayer Cropscience Ag | Derivados de arilsulfuro y arilsulfóxido acaricidas e insecticidas |
WO2014202751A1 (en) | 2013-06-21 | 2014-12-24 | Basf Se | Methods for controlling pests in soybean |
CA2916766C (en) * | 2013-06-24 | 2021-05-04 | Basf Se | Isothiazoline compounds for combating invertebrate pests |
EP3013820A1 (en) * | 2013-06-24 | 2016-05-04 | Basf Se | Bicyclyl-substituted isothiazoline compounds |
JP2015028006A (ja) | 2013-06-27 | 2015-02-12 | 日産化学工業株式会社 | イソキサゾリン化合物の結晶性多形体およびその製造方法 |
TW201542532A (zh) | 2013-07-08 | 2015-11-16 | Bayer Cropscience Ag | 作為殺蟲劑的六員c-n-鍵結之芳基硫化物及芳基亞碸衍生物 |
CN105531265B (zh) | 2013-07-15 | 2018-07-20 | 巴斯夫欧洲公司 | 杀害虫化合物 |
EP3046919B1 (en) | 2013-09-19 | 2019-08-07 | Basf Se | N-acylimino heterocyclic compounds |
WO2015055554A1 (de) | 2013-10-14 | 2015-04-23 | Bayer Cropscience Ag | Wirkstoff für die saatgut- und bodenbehandlung |
UY35772A (es) | 2013-10-14 | 2015-05-29 | Bayer Cropscience Ag | Nuevos compuestos plaguicidas |
WO2015055497A1 (en) | 2013-10-16 | 2015-04-23 | Basf Se | Substituted pesticidal pyrazole compounds |
JP6644681B2 (ja) | 2013-10-18 | 2020-02-12 | ビーエーエスエフ アグロケミカル プロダクツ ビー.ブイ. | 土壌及び種子施用における殺有害生物活性カルボキサミド誘導体の使用、並びに処理方法 |
JP6472444B2 (ja) | 2013-10-23 | 2019-02-20 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 有害生物防除剤としての置換されているキノキサリン誘導体 |
US9371293B2 (en) | 2013-10-25 | 2016-06-21 | Sumitomo Chemical Company, Limited | Isoxazoline compound composition |
EA030935B1 (ru) * | 2013-11-01 | 2018-10-31 | Мериал, Инк. | Антипаразитарные и пестицидные изоксазолиновые соединения |
RU2673723C1 (ru) | 2013-12-10 | 2018-11-29 | Интервет Интернэшнл Б.В. | Применение содержащих изоксазолин соединений в качестве противопаразитарных средств |
WO2015091649A1 (en) | 2013-12-18 | 2015-06-25 | Basf Se | N-substituted imino heterocyclic compounds |
EP3083596A1 (en) | 2013-12-18 | 2016-10-26 | Basf Se | Azole compounds carrying an imine-derived substituent |
HUE055444T2 (hu) | 2013-12-20 | 2021-11-29 | Intervet Int Bv | Izoxazolinszármazákok felhasználása baromfiak arthropodafertõzéseinek kezelésére vagy megelõzésére |
HUE066811T2 (hu) | 2013-12-20 | 2024-09-28 | Intervet Int Bv | Izoxazolin kompozíciók és azok felhasználása parazitafertõzések megelõzésében és kezelésében állatokban |
EP3089972B1 (de) | 2014-01-03 | 2018-05-16 | Bayer Animal Health GmbH | Neue pyrazolyl-heteroarylamide als schädlingsbekämpfungsmittel |
WO2015104422A1 (en) | 2014-01-13 | 2015-07-16 | Basf Se | Dihydrothiophene compounds for controlling invertebrate pests |
WO2015107133A1 (de) | 2014-01-20 | 2015-07-23 | Bayer Cropscience Ag | Chinolinderivate als insektizide und akarizide |
DE202014008415U1 (de) | 2014-02-19 | 2014-11-25 | Clariant International Ltd. | Wässrige Adjuvant-Zusammensetzung zur Wirkungssteigerung von Elektrolyt-Wirkstoffen |
DE202014008418U1 (de) | 2014-02-19 | 2014-11-14 | Clariant International Ltd. | Schaumarme agrochemische Zusammensetzungen |
PE20161068A1 (es) * | 2014-02-26 | 2016-10-21 | Basf Se | Compuestos de azolina |
BR112016022688B1 (pt) | 2014-04-02 | 2021-09-08 | Bayer Cropscience Aktiengesellschaft | Derivados de n-(1-(hetero)aril-1h-pirazol-4-il)-(hetero)arilamida e composições contendo os mesmos |
WO2015160620A1 (en) | 2014-04-16 | 2015-10-22 | Bayer Cropscience Lp | Compositions comprising ningnanmycin and an insecticide |
WO2015160618A1 (en) | 2014-04-16 | 2015-10-22 | Bayer Cropscience Lp | Compositions comprising ningnanmycin and a biological control agent |
MX378055B (es) | 2014-04-17 | 2025-03-10 | Boehringer Ingelheim Animal Health Usa Inc | Uso de compuestos de malononitrilo para proteger animales de parásitos. |
DE102014005771A1 (de) | 2014-04-23 | 2015-10-29 | Clariant International Ltd. | Verwendung von wässrigen driftreduzierenden Zusammensetzungen |
EP3139743B1 (en) | 2014-05-08 | 2018-03-14 | Bayer CropScience Aktiengesellschaft | Pyrazolopyridine sulfonamides as nematicides |
JP6616786B2 (ja) | 2014-05-19 | 2019-12-04 | メリアル インコーポレイテッド | 駆虫性化合物 |
JP6615791B2 (ja) | 2014-06-05 | 2019-12-04 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺虫剤としての二環式化合物 |
AU2015276941B2 (en) | 2014-06-19 | 2018-07-19 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal compositions comprising indole derivatives, methods and uses thereof |
JP6628048B2 (ja) * | 2014-06-30 | 2020-01-08 | 日産化学株式会社 | 殺虫、殺ダニ、殺線虫、殺軟体動物、殺菌又は殺バクテリア組成物及び病害虫の防除方法 |
WO2016001119A1 (de) | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Insektizide und fungizide wirkstoffkombinationen |
JP2017521441A (ja) | 2014-07-15 | 2017-08-03 | バイエル・アニマル・ヘルス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Animal Health Gmbh | 有害生物防除剤としてのアリール−トリアゾリルピリジン類 |
US20170232024A1 (en) | 2014-08-04 | 2017-08-17 | Jerry Tan Eye Surgery Pte Ltd | Pharmaceutical compositions for demodex related blepharitis and eyelid crusting |
DE102014012022A1 (de) | 2014-08-13 | 2016-02-18 | Clariant International Ltd. | Organische Ammoniumsalze von anionischen Pestiziden |
SI3203840T1 (sl) | 2014-10-06 | 2020-10-30 | Vertex Pharmaceuticals Incorporated | Modulatorji regulatorja transmembranske prevodnosti pri cistični fibrozi |
WO2016055096A1 (en) | 2014-10-07 | 2016-04-14 | Bayer Cropscience Ag | Method for treating rice seed |
US10864193B2 (en) | 2014-10-31 | 2020-12-15 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal compositions comprising fipronil at high concentrations |
AR102942A1 (es) | 2014-12-11 | 2017-04-05 | Bayer Cropscience Ag | Derivados de arilsulfuro y arilsulfóxido de cinco miembros c-n-conectados, como plaguicidas |
DE102014018274A1 (de) | 2014-12-12 | 2015-07-30 | Clariant International Ltd. | Zuckertenside und deren Verwendung in agrochemischen Zusammensetzungen |
AU2015367344A1 (en) | 2014-12-19 | 2017-07-13 | Clariant International Ltd | Aqueous electrolyte-containing adjuvant compositions, active ingredient-containing compositions and the use thereof |
EP3240423B1 (en) | 2014-12-22 | 2020-10-21 | Bayer CropScience LP | Method for using a bacillus subtilis or bacillus pumilus strain to treat or prevent pineapple disease |
PT4008329T (pt) | 2014-12-22 | 2025-07-30 | Intervet Int Bv | Compostos de isoxazolina para utilização no tratamento da demodicose |
PE20171182A1 (es) * | 2014-12-22 | 2017-08-22 | Basf Se | Compuestos ciclicos sustituidos con un sistema de anillos condensado |
DK3237410T3 (da) | 2014-12-22 | 2021-03-15 | Basf Se | Azolinforbindelser, der er substitueret med et kondenseret ringsystem |
US10085448B2 (en) | 2014-12-22 | 2018-10-02 | Basf Se | Azoline compounds substituted by a carbocyclic condensed ring system |
EP3081085A1 (en) | 2015-04-14 | 2016-10-19 | Bayer CropScience AG | Method for improving earliness in cotton |
UY36547A (es) | 2015-02-05 | 2016-06-01 | Bayer Cropscience Ag | Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas |
UY36548A (es) | 2015-02-05 | 2016-06-01 | Bayer Cropscience Ag | Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas |
TWI702212B (zh) | 2015-02-09 | 2020-08-21 | 德商拜耳作物科學股份有限公司 | 作為除害劑之經取代的2-硫基咪唑基羧醯胺類 |
UY36570A (es) | 2015-02-26 | 2016-10-31 | Merial Inc | Formulaciones inyectables de acción prolongada que comprenden un agente activo isoxazolina, métodos y usos de las mismas |
AU2016231174B2 (en) | 2015-03-10 | 2020-09-10 | Bayer Animal Health Gmbh | Pyrazolyl-derivatives as pest control agents |
WO2016155831A1 (en) | 2015-04-02 | 2016-10-06 | Syngenta Participations Ag | Isoxazoline-styrene derivatives as insecticidal compounds |
WO2016162318A1 (de) | 2015-04-08 | 2016-10-13 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel und deren zwischenprodukte |
EP3280413A1 (en) | 2015-04-08 | 2018-02-14 | Merial, Inc. | Extended release injectable formulations comprising an isoxazoline active agent, methods and uses thereof |
WO2016174049A1 (en) | 2015-04-30 | 2016-11-03 | Bayer Animal Health Gmbh | Anti-parasitic combinations including halogen-substituted compounds |
EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
WO2016180802A1 (de) | 2015-05-13 | 2016-11-17 | Bayer Cropscience Aktiengesellschaft | Insektizide arylpyrrolidine, verfahren zu ihrer herstellung und ihre verwendung als wirkstoffe zur bekämpfung tierischer schädlinge |
SI3298027T1 (sl) | 2015-05-20 | 2021-08-31 | Boehringer Ingelheim Animal Health USA Inc. | Antihelmintične depsipeptidne spojine |
PL3313400T3 (pl) | 2015-06-23 | 2022-07-25 | Intervet International B.V. | Roztwór izoksazoliny zawierający witaminę e do stosowania z odkażoną wodą pitną |
MX2018000292A (es) | 2015-07-06 | 2018-04-20 | Bayer Cropscience Ag | Compuestos heterociclicos como pesticidas. |
CN105123298B (zh) * | 2015-07-08 | 2017-07-11 | 吉林省农业科学院 | 一种非选择性鉴定大豆抗大豆食心虫的室内生物测定方法 |
US10667517B2 (en) | 2015-08-07 | 2020-06-02 | Bayer Cropscience Aktiengesellschaft | 2-(Het)aryl-substituted fused heterocycle derivatives as pesticides |
AR106070A1 (es) * | 2015-09-23 | 2017-12-06 | Syngenta Participations Ag | Benzamidas sustituidas con isoxazolina como insecticidas |
UY36910A (es) | 2015-09-23 | 2017-04-28 | Syngenta Participations Ag | Benzamidas de bis isoxazolinas como compuestos insecticidas |
DE102015219651A1 (de) | 2015-10-09 | 2017-04-13 | Clariant International Ltd. | Zusammensetzungen enthaltend Zuckeramin und Fettsäure |
DE102015219608B4 (de) | 2015-10-09 | 2018-05-03 | Clariant International Ltd | Universelle Pigmentdispersionen auf Basis von N-Alkylglukaminen |
KR20180109076A (ko) * | 2016-01-25 | 2018-10-05 | 다우 아그로사이언시즈 엘엘씨 | 살충 유용성을 갖는 분자, 및 그와 관련된 중간체, 조성물 및 방법 |
WO2017132023A1 (en) * | 2016-01-25 | 2017-08-03 | Dow Agrosciences Llc | Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto |
EP3407716B9 (en) | 2016-01-25 | 2021-07-14 | Corteva Agriscience LLC | Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto |
US20190059381A1 (en) | 2016-02-19 | 2019-02-28 | Basf Se | Method for controlling pests of soybean, corn, and cotton plants |
UY37137A (es) | 2016-02-24 | 2017-09-29 | Merial Inc | Compuestos antiparasitarios de isoxazolina, formulaciones inyectables de acción prolongada que los comprenden, métodos y usos de los mismos |
EP3210468A1 (de) | 2016-02-26 | 2017-08-30 | Bayer CropScience Aktiengesellschaft | Lösungsmittelfreie formulierungen von niedrig schmelzenden wirkstoffen |
PL3436446T3 (pl) | 2016-03-31 | 2023-09-11 | Vertex Pharmaceuticals Incorporated | Modulatory mukowiscydozowego przezbłonowego regulatora przewodnictwa |
HUE056909T2 (hu) | 2016-04-06 | 2022-04-28 | Boehringer Ingelheim Animal Health Usa Inc | Eljárás enantiomerben dúsított izoxazolinvegyületek elõállítására -(S)-afoxolaner kristályos toluolszolvátja |
BR122021026787B1 (pt) | 2016-04-24 | 2023-05-16 | Bayer Cropscience Aktiengesellschaft | Uso de cepa qst 713 de bacillus subtilis, e método para controle de murcha de fusarium em plantas da família musaceae |
TWI696615B (zh) * | 2016-05-05 | 2020-06-21 | 瑞士商伊蘭科動物健康公司 | 雜芳基-1,2,4-三唑及雜芳基-三唑化合物 |
DE102016207877A1 (de) | 2016-05-09 | 2017-11-09 | Clariant International Ltd | Stabilisatoren für Silikatfarben |
US10653135B2 (en) | 2016-07-11 | 2020-05-19 | Covestro Llc | Methods for treating seeds with an aqueous composition and seeds treated therewith |
US10653136B2 (en) | 2016-07-11 | 2020-05-19 | Covestro Llc | Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds |
US10750750B2 (en) | 2016-07-11 | 2020-08-25 | Covestro Llc | Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds |
US20190297887A1 (en) | 2016-07-12 | 2019-10-03 | Bayer Cropscience Aktiengesellschaft | Bicyclic compounds as pesticides |
US20190159451A1 (en) | 2016-07-29 | 2019-05-30 | Bayer Cropscience Aktiengesellschaft | Active compound combinations and methods to protect the propagation material of plants |
WO2018039508A1 (en) | 2016-08-25 | 2018-03-01 | Merial, Inc. | Method for reducing unwanted effects in parasiticidal treatments |
CN109640663A (zh) | 2016-08-30 | 2019-04-16 | 巴斯夫欧洲公司 | 防治修饰植物中的害虫的方法 |
PT3519401T (pt) | 2016-09-30 | 2021-12-27 | Vertex Pharma | Modulador de regulador de condutância transmembranar de fibrose quística, composições farmacêuticas, métodos de tratamento e processo para fazer o modulador |
WO2018071535A1 (en) | 2016-10-14 | 2018-04-19 | Merial, Inc. | Pesticidal and parasiticidal vinyl isoxazoline compounds |
WO2018069841A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-substituted phenylamine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
CN109890206A (zh) | 2016-10-14 | 2019-06-14 | 印度商皮埃企业有限公司 | 4-经取代之苯胺衍生物及其在对抗不欲之植物病原微生物以保护作物上之用途 |
WO2018093920A1 (en) | 2016-11-16 | 2018-05-24 | Merial, Inc. | Anthelmintic depsipeptide compounds |
EP3400801A1 (en) | 2017-05-10 | 2018-11-14 | Bayer CropScience Aktiengesellschaft | Plant health effect of purpureocillium lilacinum |
KR102269492B1 (ko) | 2016-12-09 | 2021-06-24 | 버텍스 파마슈티칼스 인코포레이티드 | 낭포성 섬유증 막관통 전도성 조절인자의 조절제, 약제학적 조성물, 치료 방법, 및 상기 조절제를 제조하는 방법 |
WO2018116072A1 (en) | 2016-12-20 | 2018-06-28 | Pi Industries Ltd. | Heterocyclic compounds |
WO2018116073A1 (en) | 2016-12-21 | 2018-06-28 | Pi Industries Ltd. | 1, 2, 3-thiadiazole compounds and their use as crop protecting agent |
TW201840542A (zh) * | 2017-03-22 | 2018-11-16 | 瑞士商先正達合夥公司 | 殺有害生物活性環丙基甲基醯胺衍生物 |
EP3601280A1 (en) * | 2017-03-23 | 2020-02-05 | Syngenta Participations AG | Insecticidal compounds |
AR111260A1 (es) | 2017-03-31 | 2019-06-19 | Intervet Int Bv | Formulación farmacéutica de la sal de crotonil amino piridina |
JP7334118B2 (ja) | 2017-03-31 | 2023-08-28 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 節足動物を防除するための三環式カルボキサミド類 |
WO2018177993A1 (de) | 2017-03-31 | 2018-10-04 | Bayer Cropscience Aktiengesellschaft | Pyrazole zur bekämpfung von arthropoden |
TWI780112B (zh) | 2017-03-31 | 2022-10-11 | 美商科迪華農業科技有限責任公司 | 具有殺蟲效用之分子,及其相關之中間物、組成物暨方法 |
AU2018254010B2 (en) | 2017-04-20 | 2022-05-12 | Pi Industries Ltd. | Novel phenylamine compounds |
RU2019136972A (ru) * | 2017-04-26 | 2021-05-26 | Басф Се | Замещенные сукцинимидные производные в качестве пестицидов |
WO2018227049A1 (en) | 2017-06-08 | 2018-12-13 | Vertex Pharmaceuticals Incorporated | Methods of treatment for cystic fibrosis |
WO2018228986A1 (de) * | 2017-06-13 | 2018-12-20 | Bayer Aktiengesellschaft | Herbizid wirksame 3-phenylisoxazolin-5-carboxamide von tetrahydro- und dihydrofurancarbonsäureamiden |
WO2019007891A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide wirkstoffkombinationen |
WO2019007888A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide wirkstoffkombinationen |
WO2019007887A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide und fungizide wirkstoffkombinationen |
BR112020000941A2 (pt) | 2017-07-17 | 2020-07-21 | Vertex Pharmaceuticals Incorporated | métodos de tratamento para fibrose cística |
CN111051280B (zh) | 2017-08-02 | 2023-12-22 | 弗特克斯药品有限公司 | 制备吡咯烷化合物的方法 |
EP3668866B1 (en) * | 2017-08-14 | 2023-01-18 | Boehringer Ingelheim Animal Health USA Inc. | Pesticidal and parasiticidal pyrazole-isoxazoline compounds |
MY202302A (en) | 2017-09-06 | 2024-04-23 | Bayer Animal Health Gmbh | Topically administrable formulation for the control and prevention of animal parasites |
EP3473103A1 (de) | 2017-10-17 | 2019-04-24 | Bayer AG | Wässrige suspensionskonzentrate auf basis von 2-[(2,4-dichlorphenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinon |
TWI719349B (zh) | 2017-10-19 | 2021-02-21 | 美商維泰克斯製藥公司 | Cftr調節劑之結晶形式及組合物 |
JP7446222B2 (ja) | 2017-11-07 | 2024-03-08 | インターベット インターナショナル ベー. フェー. | 大きいサイズのイソキサゾリン粒子の調製方法 |
CA3081646C (en) | 2017-11-07 | 2024-03-19 | Intervet International B.V. | Injectable isoxazoline pharmaceutical compositions and uses thereof |
KR102094916B1 (ko) * | 2017-12-04 | 2020-03-30 | 조명행 | 닭진드기 살충제 조성물 및 이의 제조방법 |
US11465985B2 (en) | 2017-12-08 | 2022-10-11 | Vertex Pharmaceuticals Incorporated | Processes for making modulators of cystic fibrosis transmembrane conductance regulator |
MX2020006055A (es) | 2017-12-12 | 2020-08-20 | Intervet Int Bv | Composiciones farmaceuticas implantables de isoxazolina y usos de las mismas. |
EP4397375A3 (en) | 2017-12-15 | 2024-09-25 | Tarsus Pharmaceuticals, Inc. | Isoxazoline parasiticide formulations and methods for treating blepharitis |
US20200337311A1 (en) | 2017-12-20 | 2020-10-29 | Pi Industries Ltd. | Fluoralkenyl compounds, process for preparation and use thereof |
AR113997A1 (es) | 2017-12-21 | 2020-07-08 | Intervet Int Bv | Composiciones antiparasitarias para unción dorsal continua |
CN108191784B (zh) * | 2018-01-12 | 2020-03-06 | 洛阳师范学院 | 一种5-二氟乙基[4,5]二氢异恶唑衍生物及其制备方法 |
WO2019150311A1 (en) | 2018-02-02 | 2019-08-08 | Pi Industries Ltd. | 1-3 dithiol compounds and their use for the protection of crops from phytopathogenic microorganisms |
TWI810243B (zh) | 2018-02-05 | 2023-08-01 | 美商維泰克斯製藥公司 | 用於治療囊腫纖化症之醫藥組合物 |
WO2019157241A1 (en) | 2018-02-08 | 2019-08-15 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal compositions comprising eprinomectin and praziquantel, methods and uses thereof |
WO2019200246A1 (en) | 2018-04-13 | 2019-10-17 | Alexander Russell Abela | Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
WO2020002189A1 (de) | 2018-06-27 | 2020-01-02 | Bayer Aktiengesellschaft | Wirkstoffkombinationen |
WO2020002593A1 (en) | 2018-06-29 | 2020-01-02 | Intervet International B.V. | Compound for use against helminthic infection |
WO2020014068A1 (en) | 2018-07-09 | 2020-01-16 | Boehringer Ingelheim Animal Health USA Inc. | Anthelminthic heterocyclic compounds |
KR20210038617A (ko) | 2018-07-27 | 2021-04-07 | 바이엘 악티엔게젤샤프트 | 농약용 제어 방출 제제 |
WO2020025650A1 (en) | 2018-07-31 | 2020-02-06 | Bayer Aktiengesellschaft | Controlled release formulations with lignin for agrochemicals |
WO2020035826A1 (en) | 2018-08-17 | 2020-02-20 | Pi Industries Ltd. | 1,2-dithiolone compounds and use thereof |
US20220048876A1 (en) * | 2018-09-26 | 2022-02-17 | Syngenta Participations Ag | Insecticidal compounds |
AU2019348400A1 (en) * | 2018-09-26 | 2021-04-01 | Syngenta Crop Protection Ag | Pesticidally active cyclopropyl methyl amide derivatives |
CA3113874A1 (en) | 2018-10-29 | 2020-05-07 | Basf Se | Process for preparation of optically enriched aldol compounds |
BR112021007784A2 (pt) | 2018-11-06 | 2021-07-27 | Basf Se | processo para preparar compostos de isoxazolina opticamente enriquecidos |
CN113260419A (zh) | 2018-11-20 | 2021-08-13 | 勃林格殷格翰动物保健美国公司 | 吲唑基氰基乙基氨基化合物、其组合物、其制备方法和其使用方法 |
CA3120221A1 (en) | 2018-12-04 | 2020-06-11 | Basf Se | Process for preparation of 5-bromo-1,3-dichloro-2-fluoro-benzene |
AU2019400839B2 (en) | 2018-12-21 | 2025-01-02 | Intervet International B.V. | Method for producing (5S)-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4Hisoxazol-3-yl]-2-methyl-benzonic acid |
TW202039450A (zh) | 2018-12-21 | 2020-11-01 | 荷蘭商英特威國際公司 | 生產(5s)-4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4h-異㗁唑-3-基]-2-甲基-苯甲酸之方法 |
TW202039449A (zh) | 2018-12-21 | 2020-11-01 | 荷蘭商英特威國際公司 | (5r)-4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4h-異㗁唑-3-基]-2-甲基-苯甲酸之消旋化的方法 |
NZ776819A (en) | 2019-01-16 | 2023-04-28 | Boehringer Ingelheim Animal Health Usa Inc | Topical compositions comprising a neonicotinoid and a macrocyclic lactone, methods and uses thereof |
EP3696177A1 (en) | 2019-02-12 | 2020-08-19 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
AR118215A1 (es) | 2019-03-01 | 2021-09-22 | Boehringer Ingelheim Animal Health Usa Inc | Composiciones inyectables de clorsulón, sus métodos y usos |
CN109879826B (zh) * | 2019-03-18 | 2021-04-13 | 丽珠集团新北江制药股份有限公司 | 一种异噁唑啉类杀虫剂的制备方法 |
KR20250112307A (ko) | 2019-03-19 | 2025-07-23 | 베링거잉겔하임베트메디카게엠베하 | 구충성 아자-벤조티오펜 및 아자-벤조푸란 화합물 |
AU2020268618A1 (en) | 2019-05-03 | 2021-11-04 | Intervet International B.V. | Injectable pharmaceutical compositions and uses thereof |
CN110199999A (zh) * | 2019-06-19 | 2019-09-06 | 江西正邦作物保护有限公司 | 一种含有氟噁唑酰胺和唑虫酰胺的农药组合物 |
EP3988548A4 (en) * | 2019-06-21 | 2023-02-22 | Nihon Nohyaku Co., Ltd. | Oxadiazole compound or salts thereof, and agricultural/horticultural bactericide containing said compound, and method for using same |
BR112021026509A2 (pt) * | 2019-07-01 | 2022-02-15 | Univ Shenyang Chemical Tech | Composto de isoxazolina, seu método de preparação e sua aplicação |
EP4003292A1 (en) | 2019-07-22 | 2022-06-01 | Intervet International B.V. | Soft chewable veterinary dosage form |
US20220304305A1 (en) | 2019-09-11 | 2022-09-29 | Bayer Aktiengesellschaft | Highly effective formulations on the basis of 2-[(2,4-dichlorphenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinones and preemergence herbicides |
WO2021122521A1 (en) | 2019-12-16 | 2021-06-24 | Intervet International B.V. | Composition for lice control in poultry |
WO2021122513A1 (en) | 2019-12-16 | 2021-06-24 | Intervet International B.V. | Composition for lice control |
US20230095926A1 (en) | 2019-12-16 | 2023-03-30 | Intervet Inc. | Parasite control in ruminants |
WO2021122356A1 (en) * | 2019-12-17 | 2021-06-24 | Krka, D.D., Novo Mesto | Process for preparing fluralaner |
WO2021127188A1 (en) * | 2019-12-18 | 2021-06-24 | Elanco Tiergesundheit Ag | Isoxazoline derivatives as pesticides |
TW202136238A (zh) * | 2020-01-06 | 2021-10-01 | 大陸商廣東東陽光藥業有限公司 | RORγt抑制劑及其製備方法和用途 |
CN113354551B (zh) * | 2020-03-04 | 2024-08-23 | 东莞市东阳光动物保健药品有限公司 | 一种酰胺化合物的制备方法 |
CN113461653B (zh) * | 2020-03-30 | 2022-09-02 | 洛阳惠中兽药有限公司 | 一种制备氟雷拉纳中间体的方法以及其制备中间体和应用 |
JP2023077429A (ja) * | 2020-04-22 | 2023-06-06 | 日本曹達株式会社 | ベンズアミド化合物および有害生物防除剤 |
CA3182659A1 (en) | 2020-05-20 | 2021-11-25 | Intervet International B.V. | Injectable pharmaceutical compositions comprising isoxazoline compounds and physiologically active macrocyclic lactone compounds and uses thereof |
AU2021278871A1 (en) | 2020-05-28 | 2023-01-19 | Boehringer Ingelheim Animal Health USA Inc. | Bi-modal release intra-ruminal capsule device and methods of use thereof |
EP4185589A1 (en) | 2020-05-29 | 2023-05-31 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic heterocyclic compounds |
CN113773269A (zh) * | 2020-06-09 | 2021-12-10 | 海门慧聚药业有限公司 | 氟雷拉纳的晶型及其制备方法 |
CN111689919A (zh) * | 2020-07-22 | 2020-09-22 | 天津市中升挑战生物科技有限公司 | 一种异噁唑啉类驱虫药的合成方法 |
CN111909143B (zh) * | 2020-07-30 | 2021-10-29 | 山东省联合农药工业有限公司 | 一种异噁唑啉取代的苯甲酰胺类衍生物及其制备方法与用途 |
CN111955469A (zh) * | 2020-08-28 | 2020-11-20 | 武汉麦世吉科技有限公司 | 一种用于黄瓜的杀虫剂以及黄瓜害虫的防除方法 |
US12108762B2 (en) * | 2020-09-08 | 2024-10-08 | Santanu Maitra | Methods of controlling crop pests using aromatic amide insect repellents, methods of making aromatic amide insect repellents, and novel aromatic amide insect repellents |
MX2023006809A (es) | 2020-12-11 | 2023-06-21 | Pi Industries Ltd | Compuestos de isoxazolina y su uso como agentes de control de plagas. |
CN116897044A (zh) | 2020-12-21 | 2023-10-17 | 勃林格殷格翰动物保健有限公司 | 包含异噁唑啉化合物的杀寄生虫环 |
CN114736168B (zh) * | 2021-01-07 | 2024-08-09 | 沈阳中化农药化工研发有限公司 | 一种含有氨甲环酸片段的异噁唑啉类衍生物及其制备和应用 |
EP4284175A1 (en) | 2021-01-27 | 2023-12-06 | Intervet International B.V. | Cyclopropylamide compounds against parasites in fish |
US20240116854A1 (en) | 2021-01-27 | 2024-04-11 | Intervet Inc. | Cyclopropylamide compounds against parasites in fish |
JP2024504816A (ja) | 2021-01-28 | 2024-02-01 | スペシャルティ オペレーションズ フランス | 農薬、微量栄養素及び着色剤の保持が改善されたイネ種子を処理するための方法 |
CN112939728A (zh) * | 2021-02-03 | 2021-06-11 | 石家庄手性化学有限公司 | 一种弗雷拉纳中间体1,3-二氯-α-(三氟甲基)苯乙烯的制备方法 |
JP2024508249A (ja) | 2021-02-11 | 2024-02-26 | ビーエーエスエフ ソシエタス・ヨーロピア | 置換イソオキサゾリン誘導体 |
EP4043444A1 (en) | 2021-02-11 | 2022-08-17 | Basf Se | Substituted isoxazoline derivatives |
CN115246795B (zh) * | 2021-04-26 | 2024-01-02 | 瑞普(天津)生物药业有限公司 | 4-苯基对位含有醚结构的异噁唑啉类化合物及其制备和作为杀虫、杀菌剂的应用 |
EP4337015A1 (en) | 2021-05-14 | 2024-03-20 | Syngenta Crop Protection AG | Insect, acarina and nematode pest control |
IL309139A (en) | 2021-06-11 | 2024-02-01 | Intervet Int Bv | Tick control methods |
MX2023014965A (es) * | 2021-06-16 | 2024-02-13 | Elanco Tiergesundheit Ag | Plaguicidas de (thi)oxazolina. |
WO2022266244A1 (en) * | 2021-06-16 | 2022-12-22 | ELANCO US, Inc. | Crystalline forms of isoxazoline compound |
AU2022292908A1 (en) * | 2021-06-16 | 2024-01-04 | Bayer Animal Health Gmbh | Isoxazoline pesticides |
US20250248976A1 (en) | 2021-06-25 | 2025-08-07 | Intervet Inc. | Palatable veterinary compositions |
CN113563322B (zh) * | 2021-07-26 | 2023-07-07 | 海利尔药业集团股份有限公司 | 一种取代的苯甲酰胺类异噁唑啉衍生物或其作为农药可接受的盐、组合物及其用途 |
CN114907236B (zh) * | 2021-08-26 | 2024-02-09 | 四川青木制药有限公司 | 一种醛肟类化合物及其制备方法和应用 |
CN113582987B (zh) * | 2021-09-02 | 2023-06-30 | 海利尔药业集团股份有限公司 | 一种取代的苯甲酰胺异噁唑啉衍生物或其作为农药可接受的盐、组合物及其用途 |
EP4426677A1 (en) | 2021-11-03 | 2024-09-11 | Bayer Aktiengesellschaft | Bis(hetero)aryl thioether (thio)amides as fungicidal compounds |
WO2023092050A1 (en) | 2021-11-20 | 2023-05-25 | Bayer Cropscience Lp | Beneficial combinations with recombinant bacillus cells expressing a serine protease |
CN113896690B (zh) * | 2021-11-22 | 2023-04-21 | 常州齐晖药业有限公司 | 一种异噁唑啉类驱虫药氟雷拉纳的制备方法 |
JP2024543953A (ja) | 2021-11-30 | 2024-11-26 | バイエル、アクチエンゲゼルシャフト | 抗真菌化合物としてのビス(ヘテロ)アリールチオエーテルオキサジアジン |
US20250052673A1 (en) | 2021-12-15 | 2025-02-13 | Bayer Aktiengesellschaft | Spectroscopic solution for non-destructive quantification of one or more chemical substances in a matrix comprising coating and bulk material in a sample, such as coated seeds, using multivariate data analysis |
KR102660238B1 (ko) * | 2021-12-20 | 2024-04-25 | 주식회사경농 | 다이하이드로아이소옥사졸 유도체 화합물 및 이를 포함하는 살충제 조성물 |
WO2023118434A1 (en) * | 2021-12-22 | 2023-06-29 | Globachem Nv | Pesticidally active amide compounds |
CN114539180B (zh) * | 2021-12-24 | 2025-02-07 | 贵州大学 | 一种含异噁唑啉的双酰胺类化合物及其制备方法和用途 |
CN114394963B (zh) * | 2022-01-12 | 2023-05-23 | 西北农林科技大学 | 一种异噁唑啉类化合物、制备方法及应用 |
CN114380762A (zh) * | 2022-01-23 | 2022-04-22 | 贵州大学 | 异恶唑啉酰肼衍生物及其制备方法和用途 |
WO2023156938A1 (en) | 2022-02-17 | 2023-08-24 | Boehringer Ingelheim Vetmedica Gmbh | Method and system for providing a fluid product mailer |
CN116784339A (zh) * | 2022-03-14 | 2023-09-22 | 山东省联合农药工业有限公司 | 一种农药组合物及其应用 |
CN114605324A (zh) * | 2022-03-28 | 2022-06-10 | 山东省联合农药工业有限公司 | 异噁唑啉取代的苯甲酰胺类衍生物及其制备方法与用途 |
WO2023203038A1 (en) | 2022-04-19 | 2023-10-26 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
CN114853748A (zh) * | 2022-05-06 | 2022-08-05 | 武汉工程大学 | 一种含三氟甲烷异噁唑啉类衍生物、其制备方法和应用 |
CN117126116A (zh) * | 2022-05-20 | 2023-11-28 | 天津瑞普生物技术股份有限公司 | 一种异噁唑啉类化合物的衍生物及其应用 |
KR20240002746A (ko) * | 2022-06-30 | 2024-01-08 | 주식회사경농 | 이속사졸린 유도체 화합물 및 이를 포함하는 살충제 조성물 |
EP4530287A1 (en) * | 2022-07-13 | 2025-04-02 | Anhui Shengfeng Biochemical Co., Ltd | Compound containing pyrazole structure, application, and insecticide |
CN115057799B (zh) * | 2022-07-21 | 2023-11-24 | 湖南海利常德农药化工有限公司 | 一种防止仲丁威原药变色的方法 |
WO2024047241A1 (en) | 2022-09-02 | 2024-03-07 | Intervet International B.V. | Treatment of fasciolosis |
CN117886806A (zh) * | 2022-09-21 | 2024-04-16 | 青岛康乔药业集团有限公司 | 含砜的五元杂环的化合物及其制备方法和应用 |
WO2024066128A1 (zh) * | 2022-10-01 | 2024-04-04 | 青岛清原化合物有限公司 | 异噁唑啉取代苯甲酰胺化合物及其应用 |
CN116375660A (zh) * | 2023-03-03 | 2023-07-04 | 广东千祺生物科技有限公司 | 一种异噁唑啉宠物用杀虫剂氟雷拉纳中间体的制备方法 |
DK182016B1 (en) | 2023-03-13 | 2025-05-28 | Zoetis Services Llc | Degradation of isoxazolines in ozonated sea water |
WO2024201231A1 (en) * | 2023-03-24 | 2024-10-03 | Hikal Limited | A process for the preparation of isoxazoline-substituted amide compounds and its intermediates thereof |
WO2025027117A1 (en) | 2023-08-02 | 2025-02-06 | Intervet International B.V. | Carboxamide-4-quinoline compounds with anthelmintic activity |
WO2025034192A1 (en) | 2023-08-07 | 2025-02-13 | Yuriy Synytsya | A water-soluble afoxolaner complex, a method for producing thereof and veterinary antiparasitic drugs comprising the same |
CN119409654A (zh) * | 2023-08-18 | 2025-02-11 | 天津瑞普生物技术股份有限公司 | 一种异噁唑啉衍生物及其制备方法与应用 |
EP4512398A1 (en) | 2023-08-25 | 2025-02-26 | Bimeda Animal Health Limited | Fluralaner for use in methods of treatment and prevention of sea lice infestation in fish |
NO20240925A1 (en) | 2023-09-15 | 2025-03-17 | Evah Atlantic Inc | Dihydroisoxazole compound for use in reducing ectoparasite infestations on fish |
CN120136803A (zh) * | 2023-12-13 | 2025-06-13 | 青岛清原化合物有限公司 | 一种异噁唑啉取代苯甲酰胺化合物及其应用 |
CN119999690A (zh) * | 2024-01-16 | 2025-05-16 | 安徽圣丰生化有限公司 | 杀虫组合物及其应用和杀虫剂 |
CN119285566A (zh) * | 2024-09-23 | 2025-01-10 | 深圳大学 | 一种异噁唑啉类化合物及其应用 |
CN120398781A (zh) * | 2025-07-02 | 2025-08-01 | 内蒙古圣雪大成制药有限公司 | 一种连续化反应制备异噁唑啉的方法 |
Family Cites Families (94)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2909509A (en) | 1956-08-16 | 1959-10-20 | Minnesota Mining & Mfg | Fluorine-containing polymers and preparation thereof |
US3391203A (en) * | 1963-10-10 | 1968-07-02 | Dow Chemical Co | Alpha-(2, 2-dichloroethyl) styrene |
GB1314812A (en) | 1969-05-20 | 1973-04-26 | Ici Ltd | Trifluoromethyl heterocyclic derivatives and compositions containing them |
US3968207A (en) | 1973-12-10 | 1976-07-06 | American Cyanamid Company | Method of controlling fleas and ticks on cats and dogs |
US4018801A (en) * | 1973-12-12 | 1977-04-19 | The Dow Chemical Company | Substituted oxirane compounds |
US3879532A (en) | 1974-01-18 | 1975-04-22 | Shell Oil Co | Control by isoxazoles of endoparasitic nematodes |
NL182879C (nl) * | 1974-05-03 | 1988-06-01 | Dow Chemical Co | Werkwijze voor de bereiding van een herbicide-preparaat, alsmede daarvoor geschikte gesubstitueerde 2-fenyl-2-ethyloxiranverbindingen. |
US4129568A (en) | 1977-05-12 | 1978-12-12 | Monsanto Company | 2-[3-Aryl-2-isoxazolin-5-yl]benzoates |
JPS6026119B2 (ja) | 1977-06-09 | 1985-06-21 | 三共株式会社 | 有機リン酸エステル類およびそれを含有する殺虫殺ダニ剤 |
CA1119178A (en) | 1977-06-09 | 1982-03-02 | Keigo Matsumoto | Mono- and di- thiophosphate esters containing an isoxazolinone ring |
EP0074069B1 (en) | 1981-09-03 | 1986-01-08 | Daikin Kogyo Co., Ltd. | Process for preparing chlorotrifluoromethylbenzene |
JPS58194869A (ja) | 1982-05-10 | 1983-11-12 | Sankyo Co Ltd | イソオキサゾリノン誘導体及び殺虫・殺ダニ剤 |
DE3335477A1 (de) * | 1983-09-30 | 1985-04-18 | Bayer Ag, 5090 Leverkusen | 2-aryl-2-halogenalkyl-oxirane |
US4629492A (en) * | 1984-10-26 | 1986-12-16 | The Dow Chemical Company | Substituted oxirane compounds |
GB8523126D0 (en) | 1985-09-19 | 1985-10-23 | Ici Plc | Aryl pyridones |
US5154749A (en) * | 1985-11-04 | 1992-10-13 | Dowelanco | Herbicidal latex dispersion for controlled delivery and release of herbicides and their preparation |
CS265658B1 (cs) * | 1986-01-31 | 1989-11-14 | Paryzkova Jana | Způsob kvantitativního stanovení vedlejších produktů v tetrabromdianu |
US5075320A (en) | 1989-01-04 | 1991-12-24 | Rehmert Chalmer V Jr | Method and composition for treating parasitic infestation of animals |
DE4013723A1 (de) | 1990-04-28 | 1991-10-31 | Basf Ag | 5-(1,2,4-triazol-1-ylmethyl)-isoxazoline |
GB9205007D0 (en) | 1992-03-07 | 1992-04-22 | Pfizer Ltd | Antiparasitic agents |
JP3313152B2 (ja) * | 1992-09-16 | 2002-08-12 | スズキ株式会社 | 自動二輪車のエンジンスタート・ステアリングロック装置 |
WO1995019773A1 (en) | 1992-10-07 | 1995-07-27 | Merck & Co., Inc. | Carbostyril oxytocin receptor antagonists |
US5569655A (en) | 1993-09-14 | 1996-10-29 | Sterling Winthrop Inc. | Substituted heterocyclylisoquinolinium salts and compositions and method of use thereof |
RU2149871C1 (ru) | 1993-11-24 | 2000-05-27 | Дзе Дюпон Мерк Фармасьютикал Компани | Изоксазолины и изоксазолы, способ подавления агрегации тромбоцитов, фармацевтическая композиция, подавляющая агрегацию тромбоцитов |
US5849736A (en) | 1993-11-24 | 1998-12-15 | The Dupont Merck Pharmaceutical Company | Isoxazoline and isoxazole fibrinogen receptor antagonists |
CZ283564B6 (cs) | 1993-11-26 | 1998-05-13 | Pfizer Inc. | 3-Aryl-2-isoxazolin-5-hydroxamové kyseliny a farmaceutické prostředky na jejich bázi |
DK0749428T3 (da) | 1994-03-09 | 1998-11-16 | Pfizer | Isooxazolinforbindelser som inhibitorer af TNF-frigivelse |
DE4408084A1 (de) | 1994-03-10 | 1995-09-14 | Hoechst Ag | 3,5-Disubstituierte und 3,4,5-trisubstituierte 2-Isoxazoline und Isoxazole, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
JPH07324045A (ja) | 1994-05-27 | 1995-12-12 | Seimi Chem Co Ltd | トラン誘導体化合物およびそれを含有する液晶組成物 |
EA000987B1 (ru) | 1995-06-21 | 2000-08-28 | Сионоги Энд Ко., Лтд. | Бициклические аминопроизводные и содержащие их антагонисты pgd2 |
DE69632548T2 (de) | 1995-12-21 | 2005-06-02 | Bristol-Myers Squibb Pharma Co. | ISOXAZOLIN, ISOTHIAZOLIN UND PYRAZOLIN ALS FAKTOR Xa INHIBITOREN |
BR9708828A (pt) | 1996-04-26 | 1999-08-03 | Nippon Soda Co | Composto e composição herbicida |
WO1997048395A1 (en) | 1996-06-19 | 1997-12-24 | Du Pont Pharmaceuticals Company | Iontophoretic delivery of integrin inhibitors |
FR2750861B1 (fr) | 1996-07-11 | 1998-12-24 | Rhone Merieux | Procedes d'elimination des parasites, et notamment des ectoparasites de vertebres, notamment de mammiferes et compositions pour la mise en oeuvre de ce procede |
DE19713626A1 (de) | 1997-04-02 | 1998-10-08 | Bayer Ag | Neue Thiodepsipeptide zur Bekämpfung von Endoparasiten und ein einfaches Verfahren zu ihrer Herstellung |
US5932766A (en) | 1997-05-30 | 1999-08-03 | Abbott Laboratories | Process for the preparation of substituted keto-enamines |
HUP0003906A2 (hu) | 1997-06-19 | 2001-05-28 | Du Pont Pharmaceuticals Co. | Xa faktort gátló hatású heterociklusos vegyületek és ezeket tartalmazó gyógyszerkészítmények |
WO1999014210A1 (en) | 1997-09-15 | 1999-03-25 | Warner-Lambert Company | Process for the preparation of substituted 5,6-dihydro-2h-pyran-2-ones |
CO5031296A1 (es) | 1997-11-04 | 2001-04-27 | Novartis Ag | Derivados de azolina, compuestos que la contienen y metodo para la preparacion y aplicacion de dicho compuesto |
RU2129430C1 (ru) | 1998-03-17 | 1999-04-27 | Общество С Ограниченной Ответственностью "Вик - Здоровье Животных" | Препарат для борьбы с экто- и эндопаразитами животных "сантомектин" |
AU739393B2 (en) | 1998-03-19 | 2001-10-11 | Merck Sharp & Dohme Corp. | Sulfurpenta fluorophenyl pyrazoles for controlling ectoparasitic infestations |
US6136838A (en) | 1998-03-19 | 2000-10-24 | Merck & Co., Inc. | Sulfurpentafluorophenylpyrazoles for controlling ectoparasitic infestations |
US6140350A (en) | 1998-06-08 | 2000-10-31 | Sumitomo Chemical Company, Limited | Method for controlling ectoparasites |
DE69901248T2 (de) | 1998-06-18 | 2002-10-02 | Novartis Ag, Basel | Zusammensetzung zum abschrecken von schädlingen |
BR9914365A (pt) | 1998-10-09 | 2001-06-26 | Novartis Ag | Combinação oral de lufenuron e nitenpiram contra pulgas |
EG22187A (en) | 1999-04-15 | 2002-10-31 | Aventis Cropscience Sa | New composition |
EP1632479B1 (en) | 1999-05-04 | 2011-01-12 | Schering Corporation | Pharmaceutical compositions comprising CCR5 antagonizing piperazine derivatives |
GB2351081A (en) | 1999-06-18 | 2000-12-20 | Lilly Forschung Gmbh | Pharmaceutically active imidazoline compounds and analogues thereof |
ES2261229T3 (es) | 1999-08-12 | 2006-11-16 | Eli Lilly And Company | Uso de spinosad o de una formulacion que comprende spinosad. |
AU2160201A (en) | 1999-11-19 | 2001-05-30 | Novartis Ag | Organic compounds and their use in the control of ectoparasites |
IL149856A0 (en) | 1999-12-02 | 2002-11-10 | Aventis Cropscience Sa | Control of arthropods in animals |
GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
HK1049165A1 (zh) | 2000-03-17 | 2003-05-02 | Bristol-Myers Squibb Pharma Company | 循环β-氨基酸衍生物作为质基金属蛋白酶及TNF-α的抑制剂 |
US6579880B2 (en) * | 2000-06-06 | 2003-06-17 | Ortho-Mcneil Pharmaceutical, Inc. | Isoxazoles and oxadiazoles as anti-inflammatory inhibitors of IL-8 |
WO2002000655A1 (en) | 2000-06-23 | 2002-01-03 | Bristol-Myers Squibb Pharma Company | 1 - (heteroaryl-phenyl) - condensed pyrazol derivatives as factor xa inhibitors |
CA2409762A1 (en) | 2000-06-23 | 2002-01-03 | Donald J.P. Pinto | Heteroaryl-phenyl substituted factor xa inhibitors |
WO2002000651A2 (en) | 2000-06-27 | 2002-01-03 | Bristol-Myers Squibb Pharma Company | Factor xa inhibitors |
DE10042736A1 (de) | 2000-08-31 | 2002-03-14 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10114597A1 (de) | 2001-03-23 | 2002-10-02 | Bayer Cropscience Gmbh | Arylisoxazolin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
CA2450589C (en) | 2001-06-08 | 2011-12-20 | Cytokine Pharmasciences, Inc. | Isoxazoline compounds having mif antagonist activity |
WO2004018410A1 (ja) * | 2002-08-26 | 2004-03-04 | Nissan Chemical Industries, Ltd. | 置換ベンズアニリド化合物及び有害生物防除剤 |
US20040069235A1 (en) | 2002-09-27 | 2004-04-15 | Rasa Cordelia G. | Flea feeding apparatus |
DE10320782A1 (de) | 2003-05-09 | 2004-11-25 | Bayer Cropscience Ag | Substituierte Oxyarene |
EP1682118B1 (en) | 2003-11-04 | 2008-10-22 | Intervet International BV | Ectoparasiticidal formulations of spinosyns and azole pesticides |
GB0402677D0 (en) | 2003-11-06 | 2004-03-10 | Novartis Ag | Organic compounds |
JP2005272452A (ja) | 2004-02-23 | 2005-10-06 | Nissan Chem Ind Ltd | 置換ベンズアニリド化合物及び有害生物防除剤 |
CN102558082B (zh) | 2004-03-05 | 2015-09-30 | 日产化学工业株式会社 | 异噁唑啉取代苯甲酰胺化合物的制备中间体 |
BRPI0507818A (pt) | 2004-03-26 | 2007-07-10 | Cytokine Pharmasciences Inc | composto e métodos de inibição |
ES2353312T3 (es) | 2004-07-28 | 2011-03-01 | Intervet International Bv | Composición veterinaria que comprende un arilpirazol y una nitroenamina con actividad antiparasitaria potenciada. |
US20090299063A1 (en) | 2005-03-29 | 2009-12-03 | Paul Shapiro | Inhibitors for Extracellular Signal-Regulated Kinase Docking Domains and Uses Therefor |
JP5051340B2 (ja) | 2005-06-06 | 2012-10-17 | 日産化学工業株式会社 | 置換イソキサゾリン化合物及び有害生物防除剤 |
MY146795A (en) | 2005-06-09 | 2012-09-28 | Novartis Ag | Process for the synthesis of organic compounds |
WO2007026965A1 (ja) | 2005-09-02 | 2007-03-08 | Nissan Chemical Industries, Ltd. | イソキサゾリン置換ベンズアミド化合物及び有害生物防除剤 |
JP2007106756A (ja) | 2005-09-14 | 2007-04-26 | Nissan Chem Ind Ltd | 置換イソキサゾリン化合物及び有害生物防除剤 |
EP1965645A2 (en) | 2005-12-14 | 2008-09-10 | E.I. Du Pont De Nemours And Company | Isoxazolines for controlling invertebrate pests |
TW200803740A (en) | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
CN101346336B (zh) | 2005-12-26 | 2013-02-27 | 日产化学工业株式会社 | 1,3-二(取代苯基)-3-取代-2-丙烯-1-酮化合物和其盐 |
TWI412322B (zh) | 2005-12-30 | 2013-10-21 | Du Pont | 控制無脊椎害蟲之異唑啉 |
PL1997813T3 (pl) | 2006-03-10 | 2010-10-29 | Nissan Chemical Ind Ltd | Podstawiony związek izoksazolinowy i środek zwalczający szkodniki |
WO2007123855A2 (en) | 2006-04-20 | 2007-11-01 | E. I. Du Pont De Nemours And Company | Pyrazolines for controlling invertebrate pests |
JPWO2007125984A1 (ja) | 2006-04-28 | 2009-09-10 | 日本農薬株式会社 | イソキサゾリン誘導体及び有害生物防除剤並びにその使用方法 |
JP2008044880A (ja) | 2006-08-15 | 2008-02-28 | Bayer Cropscience Ag | 殺虫性イソオキサゾリン類 |
EP2151437A4 (en) | 2007-03-07 | 2012-05-02 | Nissan Chemical Ind Ltd | ISOXAZOLINE SUBSTITUTED BENZAMIDE COMPOUND AND PEST CONTROL AGENT |
US8372867B2 (en) | 2007-04-10 | 2013-02-12 | Bayer Cropscience Ag | Insecticidal aryl isoxazoline derivatives |
JP5473906B2 (ja) | 2007-06-13 | 2014-04-16 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | イソキサゾリン殺虫剤 |
TWI430995B (zh) | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
CN101743000A (zh) | 2007-06-27 | 2010-06-16 | 杜邦公司 | 动物虫害控制方法 |
US8952175B2 (en) | 2007-06-27 | 2015-02-10 | Nissan Chemical Industries, Ltd. | Method for production of 3-hydroxypropan-1-one compound, method for production of 2-propen-1-one compound and method for production of isoxazoline compound |
TWI556741B (zh) | 2007-08-17 | 2016-11-11 | 英特威特國際股份有限公司 | 異唑啉組成物及其作為抗寄生蟲藥上的應用 |
TWI461411B (zh) | 2007-08-17 | 2014-11-21 | Du Pont | 製備5-鹵烷基-4,5-二氫異唑衍生物之方法 |
EP2199287A4 (en) | 2007-09-10 | 2011-04-27 | Nissan Chemical Ind Ltd | SUBSTITUTED ISOXAZOLINE COMPOUND AND AGENT FOR CONTROLLING PESTS |
US8367584B2 (en) | 2007-10-03 | 2013-02-05 | E.I. Du Pont De Nemours And Company | Naphthalene isoxazoline compounds for control of invertebrate pests |
TWI518076B (zh) | 2008-04-09 | 2016-01-21 | 杜邦股份有限公司 | 製備雜環化合物之方法 |
WO2010005048A1 (ja) | 2008-07-09 | 2010-01-14 | 日産化学工業株式会社 | イソキサゾリン置換安息香酸アミド化合物の製造方法 |
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