ES2542409T3 - Derivados de isoxazol - Google Patents
Derivados de isoxazol Download PDFInfo
- Publication number
- ES2542409T3 ES2542409T3 ES12707629.7T ES12707629T ES2542409T3 ES 2542409 T3 ES2542409 T3 ES 2542409T3 ES 12707629 T ES12707629 T ES 12707629T ES 2542409 T3 ES2542409 T3 ES 2542409T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- haloalkyl
- substituted
- cyano
- halogen
- 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.)
- Active
Links
- 150000002545 isoxazoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 128
- -1 C1-alkylsulfinyl -C6 Chemical group 0.000 claims abstract description 114
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 105
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 74
- 150000002367 halogens Chemical class 0.000 claims abstract description 73
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 56
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 51
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 34
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 31
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 31
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 28
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 24
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 19
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 18
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 17
- 125000001424 substituent group Chemical group 0.000 claims abstract description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 15
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 12
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract description 12
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 10
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 10
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 10
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims abstract description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims abstract description 6
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims abstract description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims abstract description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 4
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims abstract description 4
- 125000005347 halocycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 3
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims abstract description 3
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims abstract description 3
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000006773 (C2-C7) alkylcarbonyl group Chemical group 0.000 claims abstract description 3
- 125000006774 (C2-C7) haloalkylcarbonyl group Chemical group 0.000 claims abstract description 3
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims abstract description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 65
- 241001465754 Metazoa Species 0.000 claims description 44
- 150000003254 radicals Chemical class 0.000 claims description 29
- 239000004480 active ingredient Substances 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 244000045947 parasite Species 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 241000251468 Actinopterygii Species 0.000 claims description 7
- 241000251539 Vertebrata <Metazoa> Species 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 6
- 125000005458 thianyl group Chemical group 0.000 claims description 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 5
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- WUXYMHDSFCIQMA-UHFFFAOYSA-N n-[[5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-2-methylthiophen-3-yl]methyl]propanamide Chemical compound S1C(C)=C(CNC(=O)CC)C=C1C1=NOC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)C1 WUXYMHDSFCIQMA-UHFFFAOYSA-N 0.000 claims description 4
- ZQZFJPCIFQYLBC-UHFFFAOYSA-N [2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]furan-3-yl]methanamine Chemical compound NCC1=C(C)OC(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)=C1 ZQZFJPCIFQYLBC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000532 dioxanyl group Chemical group 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- BOTREHHXSQGWTR-UHFFFAOYSA-N oxolane-3-carboxylic acid Chemical compound OC(=O)C1CCOC1 BOTREHHXSQGWTR-UHFFFAOYSA-N 0.000 claims description 3
- YJEMQUPUTXKLMX-UHFFFAOYSA-N N-[[2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]thiophen-3-yl]methyl]cyclopropanecarboxamide Chemical compound CC=1SC(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)=CC=1CNC(=O)C1CC1 YJEMQUPUTXKLMX-UHFFFAOYSA-N 0.000 claims description 2
- HRVNBQRGLQRTMT-UHFFFAOYSA-N N-[[2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]thiophen-3-yl]methyl]propanamide Chemical compound S1C(C)=C(CNC(=O)CC)C=C1C1=NOC(C(F)(F)F)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C1 HRVNBQRGLQRTMT-UHFFFAOYSA-N 0.000 claims description 2
- RHRVWNITRNKWCH-UHFFFAOYSA-N N-[[5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylfuran-3-yl]methyl]cyclopropanecarboxamide Chemical compound CC=1OC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=CC=1CNC(=O)C1CC1 RHRVWNITRNKWCH-UHFFFAOYSA-N 0.000 claims description 2
- PSBMFJPWLMRSHY-UHFFFAOYSA-N N-[[5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylfuran-3-yl]methyl]propanamide Chemical compound O1C(C)=C(CNC(=O)CC)C=C1C1=NOC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)C1 PSBMFJPWLMRSHY-UHFFFAOYSA-N 0.000 claims description 2
- KFMNGJUVJJROFF-UHFFFAOYSA-N [5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-2-methylthiophen-3-yl]methanamine Chemical compound NCC1=C(C)SC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=C1 KFMNGJUVJJROFF-UHFFFAOYSA-N 0.000 claims description 2
- WFBFJMNWFUCZMJ-UHFFFAOYSA-N n-[[2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]furan-3-yl]methyl]cyclopropanecarboxamide Chemical compound CC=1OC(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)=CC=1CNC(=O)C1CC1 WFBFJMNWFUCZMJ-UHFFFAOYSA-N 0.000 claims description 2
- SLUWJSVOOWRWBS-UHFFFAOYSA-N n-[[2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]furan-3-yl]methyl]propanamide Chemical compound O1C(C)=C(CNC(=O)CC)C=C1C1=NOC(C(F)(F)F)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C1 SLUWJSVOOWRWBS-UHFFFAOYSA-N 0.000 claims description 2
- LTOSPMAKMXIYDK-UHFFFAOYSA-N N-[[5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylfuran-3-yl]methyl]oxolane-3-carboxamide Chemical compound CC=1OC(=CC1CNC(=O)C1COCC1)C1=NOC(C1)(C(F)(F)F)C1=CC(=CC(=C1)Cl)Cl LTOSPMAKMXIYDK-UHFFFAOYSA-N 0.000 claims 1
- IZXSNIIJCNUTPF-UHFFFAOYSA-N NCC1=C(C)SC(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)=C1 Chemical compound NCC1=C(C)SC(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)=C1 IZXSNIIJCNUTPF-UHFFFAOYSA-N 0.000 claims 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000460 chlorine Substances 0.000 description 49
- 239000000243 solution Substances 0.000 description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- 238000000034 method Methods 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000013543 active substance Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000012043 crude product Substances 0.000 description 21
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 238000009472 formulation Methods 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 18
- 241000607479 Yersinia pestis Species 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- 229920006395 saturated elastomer Polymers 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 241000238876 Acari Species 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
- 241000238631 Hexapoda Species 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 241000255925 Diptera Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- 244000078703 ectoparasite Species 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 241000258924 Ctenocephalides felis Species 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 241000258242 Siphonaptera Species 0.000 description 7
- 230000000895 acaricidal effect Effects 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000006260 foam Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 230000014759 maintenance of location Effects 0.000 description 7
- 238000011894 semi-preparative HPLC Methods 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 241000699684 Meriones unguiculatus Species 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 235000019688 fish Nutrition 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 235000013772 propylene glycol Nutrition 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
- 241000283690 Bos taurus Species 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 241001494479 Pecora Species 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 241000283086 Equidae Species 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- 241000699694 Gerbillinae Species 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 241000257303 Hymenoptera Species 0.000 description 4
- 241001674048 Phthiraptera Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000282887 Suidae Species 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 235000019445 benzyl alcohol Nutrition 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
- 239000008158 vegetable oil Substances 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- RUEKFMOVHFECGL-UHFFFAOYSA-N 2-methyl-5-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]furan-3-carbaldehyde Chemical compound O=CC1=C(C)OC(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)=C1 RUEKFMOVHFECGL-UHFFFAOYSA-N 0.000 description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 241000271566 Aves Species 0.000 description 3
- 241000322475 Bovicola Species 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 241000283707 Capra Species 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 241000699800 Cricetinae Species 0.000 description 3
- 241000709823 Dictyoptera <beetle genus> Species 0.000 description 3
- 241000287828 Gallus gallus Species 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- 241000282339 Mustela Species 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 241000238814 Orthoptera Species 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 241000286209 Phasianidae Species 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 241001481696 Rhipicephalus sanguineus Species 0.000 description 3
- 239000000642 acaricide Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 235000010980 cellulose Nutrition 0.000 description 3
- 235000013330 chicken meat Nutrition 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 229940099112 cornstarch Drugs 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 244000000013 helminth Species 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 150000002547 isoxazolines Chemical class 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 235000010981 methylcellulose Nutrition 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- BARWIPMJPCRCTP-UHFFFAOYSA-N oleic acid oleyl ester Natural products CCCCCCCCC=CCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC BARWIPMJPCRCTP-UHFFFAOYSA-N 0.000 description 3
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 230000003071 parasitic effect Effects 0.000 description 3
- 229940068196 placebo Drugs 0.000 description 3
- 239000000902 placebo Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 244000144977 poultry Species 0.000 description 3
- 235000013594 poultry meat Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- 230000002940 repellent Effects 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- WYRSGXAIHNMKOL-UHFFFAOYSA-N $l^{1}-sulfanylethane Chemical compound CC[S] WYRSGXAIHNMKOL-UHFFFAOYSA-N 0.000 description 2
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 2
- BOHGAOWOIJMTPZ-UHFFFAOYSA-N 1,3-dioxolan-4-ylmethanol Chemical compound OCC1COCO1 BOHGAOWOIJMTPZ-UHFFFAOYSA-N 0.000 description 2
- NFSSDAHKODWNNL-UHFFFAOYSA-N 1-(4-bromo-5-methylthiophen-2-yl)ethanone Chemical compound CC(=O)C1=CC(Br)=C(C)S1 NFSSDAHKODWNNL-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- NVMZCQYOSPFJLE-UHFFFAOYSA-N 2,2,2-trifluoro-1-(3,4,5-trichlorophenyl)ethanone Chemical compound FC(F)(F)C(=O)C1=CC(Cl)=C(Cl)C(Cl)=C1 NVMZCQYOSPFJLE-UHFFFAOYSA-N 0.000 description 2
- YOSDTJYMDAEEAZ-UHFFFAOYSA-N 2-acetyl-5-methylthiophene Chemical compound CC(=O)C1=CC=C(C)S1 YOSDTJYMDAEEAZ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- DVCNHGLGMDYGRK-UHFFFAOYSA-N 3-(4-bromo-5-methylthiophen-2-yl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound BrC1=C(C)SC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=C1 DVCNHGLGMDYGRK-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- 241001427556 Anoplura Species 0.000 description 2
- 241000272517 Anseriformes Species 0.000 description 2
- 241000238660 Blattidae Species 0.000 description 2
- 241000282421 Canidae Species 0.000 description 2
- 241000700114 Chinchillidae Species 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 241000490513 Ctenocephalides canis Species 0.000 description 2
- 241000256113 Culicidae Species 0.000 description 2
- 241000268912 Damalinia Species 0.000 description 2
- 241001480824 Dermacentor Species 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 241001507629 Formicidae Species 0.000 description 2
- 241001466007 Heteroptera Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241001495069 Ischnocera Species 0.000 description 2
- 241000255777 Lepidoptera Species 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 241001481703 Rhipicephalus <genus> Species 0.000 description 2
- 240000003516 Rumex sanguineus Species 0.000 description 2
- 241000257185 Sarcophagidae Species 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 241001414989 Thysanoptera Species 0.000 description 2
- 241000256856 Vespidae Species 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000002506 adulticidal effect Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000000507 anthelmentic effect Effects 0.000 description 2
- 239000000921 anthelmintic agent Substances 0.000 description 2
- 229940124339 anthelmintic agent Drugs 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 2
- 229940093471 ethyl oleate Drugs 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- RMECIRPHWNKMGM-UHFFFAOYSA-N methyl 5-(1-hydroxyethyl)-2-methylfuran-3-carboxylate Chemical compound COC(=O)C=1C=C(C(C)O)OC=1C RMECIRPHWNKMGM-UHFFFAOYSA-N 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- OQILCOQZDHPEAZ-UHFFFAOYSA-N octyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCCCCCCC OQILCOQZDHPEAZ-UHFFFAOYSA-N 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229940068917 polyethylene glycols Drugs 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 230000036962 time dependent Effects 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Polymers OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 description 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N (R)-alpha-Tocopherol Natural products 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
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DZDSQRPDUCSOQV-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-2,2,2-trifluoroethanone Chemical compound FC(F)(F)C(=O)C1=CC(Cl)=CC(Cl)=C1 DZDSQRPDUCSOQV-UHFFFAOYSA-N 0.000 description 1
- LKMBYGREMRLUCY-UHFFFAOYSA-N 1-(4-bromo-5-methylthiophen-2-yl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutan-1-one Chemical compound BrC1=C(C)SC(C(=O)CC(O)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=C1 LKMBYGREMRLUCY-UHFFFAOYSA-N 0.000 description 1
- PAWUKJOGUBVMEV-UHFFFAOYSA-N 1-(4-bromo-5-methylthiophen-2-yl)-3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-2-en-1-one Chemical compound BrC1=C(C)SC(C(=O)C=C(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=C1 PAWUKJOGUBVMEV-UHFFFAOYSA-N 0.000 description 1
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- JNYAEWCLZODPBN-UHFFFAOYSA-N 2-(1,2-dihydroxyethyl)oxolane-3,4-diol Polymers OCC(O)C1OCC(O)C1O JNYAEWCLZODPBN-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- BXYQHDXDCJQOFD-UHFFFAOYSA-N 3-cyanopropanoic acid Chemical compound OC(=O)CCC#N BXYQHDXDCJQOFD-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- XLQHYIYDFFLLRQ-UHFFFAOYSA-N 5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-2-methylthiophene-3-carbonitrile Chemical compound N#CC1=C(C)SC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=C1 XLQHYIYDFFLLRQ-UHFFFAOYSA-N 0.000 description 1
- VZUMVBQMJFFYRM-UHFFFAOYSA-N 5-bromo-1,2,3-trichlorobenzene Chemical compound ClC1=CC(Br)=CC(Cl)=C1Cl VZUMVBQMJFFYRM-UHFFFAOYSA-N 0.000 description 1
- FSEZQVUZNUMBDP-UHFFFAOYSA-N 5-formyl-2-methylfuran-3-carboxylic acid Chemical compound CC=1OC(C=O)=CC=1C(O)=O FSEZQVUZNUMBDP-UHFFFAOYSA-N 0.000 description 1
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241000238679 Amblyomma Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241001480748 Argas Species 0.000 description 1
- 241000204727 Ascaridia Species 0.000 description 1
- 241000244186 Ascaris Species 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- 241000238659 Blatta Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- SSUFDOMYCBCHML-UHFFFAOYSA-N CCCCC[S](=O)=O Chemical class CCCCC[S](=O)=O SSUFDOMYCBCHML-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282832 Camelidae Species 0.000 description 1
- 241000253350 Capillaria Species 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241001609899 Ceratophyllus gallinae Species 0.000 description 1
- 241000134426 Ceratopogonidae Species 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001307956 Chorioptes bovis Species 0.000 description 1
- 241001124179 Chrysops Species 0.000 description 1
- 241001574870 Chrysops caecutiens Species 0.000 description 1
- 241000159647 Chrysopsinae Species 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 241000202814 Cochliomyia hominivorax Species 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 241000694440 Colpidium aqueous Species 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- 241000239250 Copepoda Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000938605 Crocodylia Species 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241001128002 Demodex canis Species 0.000 description 1
- 241001481694 Dermanyssus Species 0.000 description 1
- 241000202828 Dermatobia hominis Species 0.000 description 1
- 241001414830 Diaspididae Species 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- 241001147667 Dictyocaulus Species 0.000 description 1
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 1
- 241000399934 Ditylenchus Species 0.000 description 1
- 241000283074 Equus asinus Species 0.000 description 1
- 229920000896 Ethulose Polymers 0.000 description 1
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 1
- 241000953886 Fannia canicularis Species 0.000 description 1
- 241000242711 Fasciola hepatica Species 0.000 description 1
- 241001660201 Gasterophilus intestinalis Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000257324 Glossina <genus> Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241001480796 Haemaphysalis Species 0.000 description 1
- 241001481667 Haematobia irritans exigua Species 0.000 description 1
- 241001276563 Haematobia irritans irritans Species 0.000 description 1
- 241000790933 Haematopinus Species 0.000 description 1
- 241000775881 Haematopota pluvialis Species 0.000 description 1
- 241000243976 Haemonchus Species 0.000 description 1
- 241000920462 Heterakis Species 0.000 description 1
- 241001480224 Heterodera Species 0.000 description 1
- CMBYOWLFQAFZCP-UHFFFAOYSA-N Hexyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCCCC CMBYOWLFQAFZCP-UHFFFAOYSA-N 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 244000025221 Humulus lupulus Species 0.000 description 1
- 241001480803 Hyalomma Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 241000543830 Hypoderma bovis Species 0.000 description 1
- 241000257174 Hypoderma lineatum Species 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 241000238681 Ixodes Species 0.000 description 1
- 241000545319 Ixodes canisuga Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 241001113970 Linognathus Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000257166 Lucilia cuprina Species 0.000 description 1
- 241000736227 Lucilia sericata Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 241001143352 Meloidogyne Species 0.000 description 1
- 241000771994 Melophagus ovinus Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 241000238745 Musca autumnalis Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241001124166 Musca vetustissima Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- OXIPEMXHAXUIDL-UHFFFAOYSA-N N-[[5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-2-methylthiophen-3-yl]methyl]cyclopropanecarboxamide Chemical compound CC=1SC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=CC=1CNC(=O)C1CC1 OXIPEMXHAXUIDL-UHFFFAOYSA-N 0.000 description 1
- 241001137882 Nematodirus Species 0.000 description 1
- 241000772415 Neovison vison Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241000543819 Oestrus ovis Species 0.000 description 1
- 241000238887 Ornithodoros Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 241001480755 Otobius Species 0.000 description 1
- 241000283898 Ovis Species 0.000 description 1
- 241000488585 Panonychus Species 0.000 description 1
- 241000517325 Pediculus Species 0.000 description 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 1
- 241000238675 Periplaneta americana Species 0.000 description 1
- 244000025272 Persea americana Species 0.000 description 1
- 235000008673 Persea americana Nutrition 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 241000255129 Phlebotominae Species 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000193943 Pratylenchus Species 0.000 description 1
- 241001415024 Psocoptera Species 0.000 description 1
- 241001016411 Psorergates Species 0.000 description 1
- 241001649230 Psoroptes ovis Species 0.000 description 1
- 241000255131 Psychodidae Species 0.000 description 1
- 241001414857 Psyllidae Species 0.000 description 1
- 241000718000 Pulex irritans Species 0.000 description 1
- 241000201377 Radopholus Species 0.000 description 1
- 241001480809 Rhipicentor Species 0.000 description 1
- 241000304160 Sarcophaga carnaria Species 0.000 description 1
- 241000509427 Sarcoptes scabiei Species 0.000 description 1
- 241000256103 Simuliidae Species 0.000 description 1
- 241001247231 Siphonostomatoida Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000044136 Solenopotes Species 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 241001494115 Stomoxys calcitrans Species 0.000 description 1
- 241000122932 Strongylus Species 0.000 description 1
- HVWGGPRWKSHASF-UHFFFAOYSA-N Sulfuric acid, monooctadecyl ester Chemical compound CCCCCCCCCCCCCCCCCCOS(O)(=O)=O HVWGGPRWKSHASF-UHFFFAOYSA-N 0.000 description 1
- STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 1
- 241000255626 Tabanus <genus> Species 0.000 description 1
- 241001669733 Tabanus nigrovittatus Species 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 241000244031 Toxocara Species 0.000 description 1
- 241000869417 Trematodes Species 0.000 description 1
- 241000243797 Trichostrongylus Species 0.000 description 1
- 241001489151 Trichuris Species 0.000 description 1
- 241001584775 Tunga penetrans Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 229920002494 Zein Polymers 0.000 description 1
- 108010055615 Zein Proteins 0.000 description 1
- 241001414985 Zygentoma Species 0.000 description 1
- FOLJTMYCYXSPFQ-CJKAUBRRSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-(octadecanoyloxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl octadecanoate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)CCCCCCCCCCCCCCCCC)O[C@@H]1O[C@@]1(COC(=O)CCCCCCCCCCCCCCCCC)[C@@H](O)[C@H](O)[C@@H](CO)O1 FOLJTMYCYXSPFQ-CJKAUBRRSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 238000007083 alkoxycarbonylation reaction Methods 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 125000004369 butenyl group Chemical class C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- ABSOMGPQFXJESQ-UHFFFAOYSA-M cesium;hydroxide;hydrate Chemical compound O.[OH-].[Cs+] ABSOMGPQFXJESQ-UHFFFAOYSA-M 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000031902 chemoattractant activity Effects 0.000 description 1
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- QQJKLNZDWULQGR-UHFFFAOYSA-N dipropan-2-yl benzene-1,3-dicarboxylate Chemical compound CC(C)OC(=O)C1=CC=CC(C(=O)OC(C)C)=C1 QQJKLNZDWULQGR-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- FLVVJZDJSIUVQK-UHFFFAOYSA-N dodecanoic acid;oxalic acid Chemical compound OC(=O)C(O)=O.CCCCCCCCCCCC(O)=O FLVVJZDJSIUVQK-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 244000079386 endoparasite Species 0.000 description 1
- 125000004050 enoyl group Chemical group 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 125000006437 ethyl cyclopropyl group Chemical group 0.000 description 1
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 229940074076 glycerol formal Drugs 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 244000144980 herd Species 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000006038 hexenyl group Chemical class 0.000 description 1
- 229940100463 hexyl laurate Drugs 0.000 description 1
- 125000003707 hexyloxy group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 125000003971 isoxazolinyl group Chemical group 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 229930014550 juvenile hormone Natural products 0.000 description 1
- 239000002949 juvenile hormone Substances 0.000 description 1
- 150000003633 juvenile hormone derivatives Chemical class 0.000 description 1
- 229930191400 juvenile hormones Natural products 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940099367 lanolin alcohols Drugs 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940057917 medium chain triglycerides Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- SDCYILZLINRKSD-UHFFFAOYSA-N methyl 2-methyl-5-[4,4,4-trifluoro-3-hydroxy-3-(3,4,5-trichlorophenyl)butanoyl]furan-3-carboxylate Chemical compound O1C(C)=C(C(=O)OC)C=C1C(=O)CC(O)(C(F)(F)F)C1=CC(Cl)=C(Cl)C(Cl)=C1 SDCYILZLINRKSD-UHFFFAOYSA-N 0.000 description 1
- UVRRIABXNIGUJZ-UHFFFAOYSA-N methyl 2-methylfuran-3-carboxylate Chemical compound COC(=O)C=1C=COC=1C UVRRIABXNIGUJZ-UHFFFAOYSA-N 0.000 description 1
- ZXGBIKDFARSQKO-UHFFFAOYSA-N methyl 5-acetyl-2-methylfuran-3-carboxylate Chemical compound COC(=O)C=1C=C(C(C)=O)OC=1C ZXGBIKDFARSQKO-UHFFFAOYSA-N 0.000 description 1
- WINMHOHYPKKTEM-UHFFFAOYSA-N methyl 5-formyl-2-methylfuran-3-carboxylate Chemical compound COC(=O)C=1C=C(C=O)OC=1C WINMHOHYPKKTEM-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000002255 pentenyl group Chemical class C(=CCCC)* 0.000 description 1
- 125000006194 pentinyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical class C(CCCC)* 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000010665 pine oil Substances 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
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229940068977 polysorbate 20 Drugs 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000004672 propanoic acids Chemical class 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical class [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 239000001590 sorbitan monolaureate Substances 0.000 description 1
- 235000011067 sorbitan monolaureate Nutrition 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004548 suspo-emulsion Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 229960001479 tosylchloramide sodium Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—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
- C07D417/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
- C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D419/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH407112011 | 2011-03-10 | ||
| CH4072011 | 2011-03-10 | ||
| PCT/EP2012/054161 WO2012120135A1 (en) | 2011-03-10 | 2012-03-09 | Isoxazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2542409T3 true ES2542409T3 (es) | 2015-08-05 |
Family
ID=45809012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12707629.7T Active ES2542409T3 (es) | 2011-03-10 | 2012-03-09 | Derivados de isoxazol |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8822466B2 (enExample) |
| EP (1) | EP2683713B1 (enExample) |
| JP (1) | JP2014507459A (enExample) |
| CN (1) | CN103502246A (enExample) |
| AR (1) | AR085657A1 (enExample) |
| AU (1) | AU2012224521B2 (enExample) |
| BR (1) | BR112013022755A2 (enExample) |
| CA (1) | CA2829149A1 (enExample) |
| CL (1) | CL2013002472A1 (enExample) |
| CO (1) | CO6801794A2 (enExample) |
| ES (1) | ES2542409T3 (enExample) |
| MX (1) | MX2013010297A (enExample) |
| RU (1) | RU2013145304A (enExample) |
| WO (1) | WO2012120135A1 (enExample) |
| ZA (1) | ZA201306175B (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY33403A (es) * | 2010-06-17 | 2011-12-30 | Novartis Ag | Compuestos orgánicos con novedosas isoxazolinas, sus n-óxidos, s-óxidos y sales |
| LT2811998T (lt) | 2012-02-06 | 2019-02-25 | Merial, Inc. | Paraziticidinės peroralinės veterinarinės kompozicijos, apimančios sistemiškai veikiančius aktyviuosius agentus, būdai ir jų panaudojimas |
| JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
| PL2953942T3 (pl) | 2013-02-06 | 2018-03-30 | Bayer Cropscience Aktiengesellschaft | Podstawione halogenem pochodne pirazolu jako środki do zwalczania szkodników |
| CN105473584B (zh) | 2013-06-24 | 2020-01-31 | 勃林格殷格翰动物保健美国公司 | 噻吩-或呋喃-取代的异噻唑啉化合物 |
| US9944597B2 (en) | 2013-09-16 | 2018-04-17 | The Board Of Regents Of The University Of Texas System | Polysubstituted pyrroles having microtubule-disrupting, cytotoxic and antitumor activities and methods of use thereof |
| DK3063144T3 (da) | 2013-11-01 | 2021-10-25 | Boehringer Ingelheim Animal Health Usa Inc | Antiparasitære og pesticid-isoxazolinforbindelser |
| MX2016008653A (es) | 2014-01-03 | 2016-09-26 | Bayer Animal Health Gmbh | Nuevas pirazolil-heteroarilamidas como agentes plaguicidas. |
| BR112016023898A8 (pt) | 2014-04-17 | 2021-03-30 | Basf Se | uso de compostos malononitrila para proteger animais de parasitas |
| 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 |
| EP3207008B1 (en) | 2014-10-14 | 2018-07-25 | Syngenta Participations AG | Process for the preparation of 5-bromo-1,2,3-trichlorobenzene |
| EP3207018B1 (en) * | 2014-10-14 | 2018-07-25 | Syngenta Participations AG | Process for the preparation of 1-(3,5-dichloro-4-fluoro-phenyl)-2,2,2-trifluoro-ethanone |
| JP6686012B2 (ja) * | 2014-10-14 | 2020-04-22 | シンジェンタ パーティシペーションズ アーゲー | ハロ置換トリフルオロアセトフェノンを調製する方法 |
| US10040745B2 (en) | 2014-10-14 | 2018-08-07 | Syngenta Participations Ag | Process for the preparation of 1-(3,5-dichlorophenyl)-2,2,2-trifluoroethanone and derivatives thereof |
| EP3018129A1 (en) * | 2014-11-10 | 2016-05-11 | Novartis Tiergesundheit AG | Diaryl isoxazoline compound |
| 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 |
| EA036272B1 (ru) * | 2015-04-08 | 2020-10-21 | БЁРИНГЕР ИНГЕЛЬХАЙМ ЭНИМАЛ ХЕЛТ ЮЭсЭй ИНК. | Инъецируемые препараты замедленного высвобождения, содержащие изоксазолиновое действующее вещество, способы и применение |
| CN107835818B (zh) | 2015-05-20 | 2022-04-29 | 勃林格殷格翰动物保健美国公司 | 驱虫缩酚酸肽化合物 |
| UY40429A (es) | 2016-02-24 | 2023-10-13 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos antiparasitarios de isoxazolina, formulaciones inyectables de acción prolongada que los comprenden, métodos y usos de los mismos |
| WO2018039508A1 (en) | 2016-08-25 | 2018-03-01 | Merial, Inc. | Method for reducing unwanted effects in parasiticidal treatments |
| AU2017344097A1 (en) | 2016-10-14 | 2019-05-02 | Boehringer Ingelheim Animal Health USA Inc. | Pesticidal and parasiticidal vinyl isoxazoline compounds |
| EP3541789A1 (en) | 2016-11-16 | 2019-09-25 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic depsipeptide compounds |
| WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
| MX2020001724A (es) | 2017-08-14 | 2020-07-29 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos de pirazol-isoxazolina plaguicidas y parasiticidas. |
| US12269822B2 (en) | 2018-07-09 | 2025-04-08 | Boehringer Ingelheim Animal Health USA Inc. | Anthelminthic heterocyclic compounds |
| WO2020112374A1 (en) | 2018-11-20 | 2020-06-04 | Boehringer Ingelheim Animal Health USA Inc. | Indazolylcyanoethylamino compound, compositions of same, method of making, and methods of using thereof |
| MX2021011302A (es) | 2019-03-19 | 2022-01-19 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos de aza-benzotiofeno y aza-benzofurano como antihelminticos. |
| AR119790A1 (es) | 2019-08-29 | 2022-01-12 | Pi Industries Ltd | Compuestos de isoxazolina y su uso como agentes para el control de plagas |
| CN115210229A (zh) | 2020-01-03 | 2022-10-18 | 博格有限责任公司 | 多环酰胺作为治疗癌症的ube2k调节剂 |
| WO2021242481A1 (en) | 2020-05-28 | 2021-12-02 | Boehringer Ingelheim Animal Health USA Inc. | Bi-modal release intra-ruminal capsule device and methods of use thereof |
| KR20230028268A (ko) | 2020-05-29 | 2023-02-28 | 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 | 구충성 헤테로시클릭 화합물 |
| 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 |
| US20240116854A1 (en) | 2021-01-27 | 2024-04-11 | Intervet Inc. | Cyclopropylamide compounds against parasites in fish |
| JP7824305B2 (ja) | 2021-01-27 | 2026-03-04 | コルテバ アグリサイエンス エルエルシー | 魚における寄生生物に対するシクロプロピルアミド化合物 |
| NO20240925A1 (en) | 2023-09-15 | 2025-03-17 | Evah Atlantic Inc | Dihydroisoxazole compound for use in reducing ectoparasite infestations on fish |
| WO2025257633A1 (en) | 2024-06-12 | 2025-12-18 | Boehringer Ingelheim Vetmedica Gmbh | Long-acting castor oil-containing injectable formulations and methods of use thereof |
| WO2026024600A1 (en) | 2024-07-22 | 2026-01-29 | Zoetis Services Llc | Isoxazoline and macrocyclic lactone microspheres |
| WO2026043852A1 (en) | 2024-08-20 | 2026-02-26 | Zoetis Services Llc | Process for preparing optically enriched isoxazolines |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101331127B (zh) * | 2005-12-16 | 2012-05-23 | 杜邦公司 | 用于防治无脊椎害虫的5-芳基异噁唑啉 |
| TW200803740A (en) | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
| TWI412322B (zh) * | 2005-12-30 | 2013-10-21 | Du Pont | 控制無脊椎害蟲之異唑啉 |
| BRPI0707091B8 (pt) * | 2006-03-10 | 2018-02-14 | Nissan Chemical Ind Ltd | composto de isoxalina e benzaldoxima substituído ou um sal do mesmo; pesticida, agroquímico, endo- ou ecto-parasiticidapara mamíferos ou pássaros, inseticida e acaricida contendo como um ou mais ingredientes ativos selecionados a partir do composto de isoxalina substituído e o sal do mesmo |
| US8372867B2 (en) * | 2007-04-10 | 2013-02-12 | Bayer Cropscience Ag | Insecticidal aryl isoxazoline derivatives |
| TWI649303B (zh) | 2007-08-17 | 2019-02-01 | 杜邦股份有限公司 | 製備４-乙醯基-ｎ-〔２-側氧基-２-〔（２，２，２-三氟乙基）胺基〕乙基〕-１-萘甲醯胺之化合物及方法 |
| WO2009071500A2 (en) | 2007-12-03 | 2009-06-11 | Novartis Ag | Organic compounds |
| CA2747354C (en) * | 2008-12-19 | 2016-12-06 | Novartis Ag | Isoxazoline derivatives and their use as pesticide |
| JP2010235590A (ja) * | 2009-03-09 | 2010-10-21 | 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 |
| UY33403A (es) | 2010-06-17 | 2011-12-30 | Novartis Ag | Compuestos orgánicos con novedosas isoxazolinas, sus n-óxidos, s-óxidos y sales |
-
2012
- 2012-03-09 WO PCT/EP2012/054161 patent/WO2012120135A1/en not_active Ceased
- 2012-03-09 AU AU2012224521A patent/AU2012224521B2/en not_active Expired - Fee Related
- 2012-03-09 CA CA2829149A patent/CA2829149A1/en not_active Abandoned
- 2012-03-09 US US14/004,307 patent/US8822466B2/en not_active Expired - Fee Related
- 2012-03-09 JP JP2013557121A patent/JP2014507459A/ja active Pending
- 2012-03-09 CN CN201280012748.2A patent/CN103502246A/zh active Pending
- 2012-03-09 EP EP20120707629 patent/EP2683713B1/en not_active Not-in-force
- 2012-03-09 AR ARP120100793A patent/AR085657A1/es unknown
- 2012-03-09 MX MX2013010297A patent/MX2013010297A/es not_active Application Discontinuation
- 2012-03-09 BR BR112013022755A patent/BR112013022755A2/pt not_active IP Right Cessation
- 2012-03-09 RU RU2013145304/04A patent/RU2013145304A/ru not_active Application Discontinuation
- 2012-03-09 ES ES12707629.7T patent/ES2542409T3/es active Active
-
2013
- 2013-08-16 ZA ZA2013/06175A patent/ZA201306175B/en unknown
- 2013-08-21 CO CO13198103A patent/CO6801794A2/es active IP Right Grant
- 2013-08-27 CL CL2013002472A patent/CL2013002472A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2013010297A (es) | 2013-10-17 |
| RU2013145304A (ru) | 2015-04-20 |
| CL2013002472A1 (es) | 2014-03-07 |
| CO6801794A2 (es) | 2013-11-29 |
| US8822466B2 (en) | 2014-09-02 |
| ZA201306175B (en) | 2014-04-30 |
| CN103502246A (zh) | 2014-01-08 |
| EP2683713B1 (en) | 2015-04-22 |
| BR112013022755A2 (pt) | 2019-09-24 |
| NZ614662A (en) | 2015-06-26 |
| US20130345221A1 (en) | 2013-12-26 |
| EP2683713A1 (en) | 2014-01-15 |
| AU2012224521B2 (en) | 2015-10-29 |
| AU2012224521A1 (en) | 2013-09-05 |
| JP2014507459A (ja) | 2014-03-27 |
| CA2829149A1 (en) | 2012-09-13 |
| AR085657A1 (es) | 2013-10-16 |
| WO2012120135A1 (en) | 2012-09-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2542409T3 (es) | Derivados de isoxazol | |
| ES2395704T3 (es) | Derivados de isoxazolina y su uso como pesticida | |
| ES2442342T3 (es) | Derivados de las isoxazolinas y su uso como pesticida | |
| EP2582696B1 (en) | 5-aryl isoxazolines for controlling pests | |
| AU2012215440B2 (en) | Isoxazoline derivatives for controlling invertebrate pests | |
| ES2528368T3 (es) | 5-aril isoxazolinas para controlar plagas | |
| EP2934133A1 (en) | (hetero) arylacrylamides for the control of ectoparasites | |
| NZ614662B2 (en) | Isoxazole derivatives | |
| NZ613191B2 (en) | Isoxazoline derivatives for controlling invertebrate pests |