ES2526614T3 - Compuesto de benzamida sustituida con isoxazolina y agente de control de organismos nocivos - Google Patents
Compuesto de benzamida sustituida con isoxazolina y agente de control de organismos nocivos Download PDFInfo
- Publication number
- ES2526614T3 ES2526614T3 ES05720539.5T ES05720539T ES2526614T3 ES 2526614 T3 ES2526614 T3 ES 2526614T3 ES 05720539 T ES05720539 T ES 05720539T ES 2526614 T3 ES2526614 T3 ES 2526614T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- phenyl
- substituted
- atom
- haloalkyl
- 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 417
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 509
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 341
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 186
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 185
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 155
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 151
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 142
- 125000005843 halogen group Chemical group 0.000 claims abstract description 140
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 94
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 89
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 84
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 80
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 68
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 66
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 65
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 61
- 125000004429 atom Chemical group 0.000 claims abstract description 54
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 47
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 44
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 42
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 34
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims abstract description 33
- 101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims abstract description 30
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims abstract description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 19
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 15
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000003971 isoxazolinyl group Chemical group 0.000 claims abstract description 14
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 101150065749 Churc1 gene Proteins 0.000 claims abstract description 11
- 102100038239 Protein Churchill Human genes 0.000 claims abstract description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011593 sulfur Substances 0.000 claims abstract description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 7
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 199
- 125000000304 alkynyl group Chemical group 0.000 claims description 162
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 99
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 84
- 125000000217 alkyl group Chemical group 0.000 claims description 77
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 72
- 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 66
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 55
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 49
- 101100294104 Caenorhabditis elegans nhr-34 gene Proteins 0.000 claims description 40
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 35
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 34
- 125000001188 haloalkyl group Chemical group 0.000 claims description 34
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 24
- 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 24
- 101100365011 Arabidopsis thaliana SCL33 gene Proteins 0.000 claims description 23
- 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 21
- XPHBRTNHVJSEQD-UHFFFAOYSA-N anidoxime Chemical group C=1C=CC=CC=1C(CCN(CC)CC)=NOC(=O)NC1=CC=C(OC)C=C1 XPHBRTNHVJSEQD-UHFFFAOYSA-N 0.000 claims description 20
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 19
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims description 19
- 241000124008 Mammalia Species 0.000 claims description 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 16
- 101100451196 Caenorhabditis elegans hizr-1 gene Proteins 0.000 claims description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 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 13
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 13
- 239000013057 ectoparasiticide Substances 0.000 claims description 13
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 13
- 239000000575 pesticide Substances 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
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 12
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 12
- 241000238631 Hexapoda Species 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 11
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 11
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 11
- YCAGGFXSFQFVQL-UHFFFAOYSA-N Endothion Chemical compound COC1=COC(CSP(=O)(OC)OC)=CC1=O YCAGGFXSFQFVQL-UHFFFAOYSA-N 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 11
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 11
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 11
- 239000002917 insecticide Substances 0.000 claims description 11
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 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 9
- 101100478290 Arabidopsis thaliana SR30 gene Proteins 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 9
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 8
- 239000003905 agrochemical Substances 0.000 claims description 8
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 8
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 7
- 230000000895 acaricidal effect Effects 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 125000004685 alkoxythiocarbonyl group Chemical group 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000001863 phosphorothioyl group Chemical group *P(*)(*)=S 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 6
- 239000000642 acaricide Substances 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 4
- 125000005277 alkyl imino group Chemical group 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 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
- 238000007654 immersion Methods 0.000 claims description 4
- SDMSCIWHRZJSRN-UHFFFAOYSA-N isoxathion Chemical compound O1N=C(OP(=S)(OCC)OCC)C=C1C1=CC=CC=C1 SDMSCIWHRZJSRN-UHFFFAOYSA-N 0.000 claims description 4
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004844 (C1-C6) alkoxyimino group Chemical group 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 3
- 241000238889 Ixodidae Species 0.000 claims description 3
- 241000258242 Siphonaptera Species 0.000 claims description 3
- 238000003287 bathing Methods 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 3
- 108700039708 galantide Proteins 0.000 claims description 3
- 125000006782 halocycloalkylcarbonyl group Chemical group 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 3
- 238000005507 spraying Methods 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 2
- 125000006772 (C1-C6) haloalkylsulfonyloxy group Chemical group 0.000 claims description 2
- 241000238679 Amblyomma Species 0.000 claims description 2
- 241000490513 Ctenocephalides canis Species 0.000 claims description 2
- 241000258924 Ctenocephalides felis Species 0.000 claims description 2
- 241001480824 Dermacentor Species 0.000 claims description 2
- 241001549209 Echidnophaga gallinacea Species 0.000 claims description 2
- 244000111489 Gardenia augusta Species 0.000 claims description 2
- 235000018958 Gardenia augusta Nutrition 0.000 claims description 2
- 241000179420 Haemaphysalis longicornis Species 0.000 claims description 2
- 241000718000 Pulex irritans Species 0.000 claims description 2
- 241000238680 Rhipicephalus microplus Species 0.000 claims description 2
- 241001481696 Rhipicephalus sanguineus Species 0.000 claims description 2
- 241000353223 Xenopsylla cheopis Species 0.000 claims description 2
- 238000007918 intramuscular administration Methods 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 238000007920 subcutaneous administration Methods 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 claims 5
- 241000238681 Ixodes Species 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 2
- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical compound C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
- 239000007928 intraperitoneal injection Substances 0.000 claims 1
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 1
- 229910014455 Ca-Cb Inorganic materials 0.000 description 105
- 238000006243 chemical reaction Methods 0.000 description 74
- 239000002904 solvent Substances 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- 150000001721 carbon Chemical group 0.000 description 40
- 239000003795 chemical substances by application Substances 0.000 description 40
- 239000000203 mixture Substances 0.000 description 39
- 238000004519 manufacturing process Methods 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- 238000009472 formulation Methods 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 20
- 239000004567 concrete Substances 0.000 description 19
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 18
- 239000012669 liquid formulation Substances 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 239000000243 solution Substances 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 241000607479 Yersinia pestis Species 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000002360 preparation method 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
- 150000001408 amides Chemical class 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 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
- 239000000047 product Substances 0.000 description 10
- 239000003981 vehicle Substances 0.000 description 10
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 9
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- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
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- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 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
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
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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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- C07C255/00—Carboxylic acid nitriles
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- C07C255/24—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
- 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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- 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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- 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
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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JP2004061749 | 2004-03-05 | ||
JP2004061749 | 2004-03-05 | ||
JP2004200119 | 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 |
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ES2526614T3 true ES2526614T3 (es) | 2015-01-13 |
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