CN1192651A - 杀体外寄生虫组合物 - Google Patents
杀体外寄生虫组合物 Download PDFInfo
- Publication number
- CN1192651A CN1192651A CN96196168A CN96196168A CN1192651A CN 1192651 A CN1192651 A CN 1192651A CN 96196168 A CN96196168 A CN 96196168A CN 96196168 A CN96196168 A CN 96196168A CN 1192651 A CN1192651 A CN 1192651A
- Authority
- CN
- China
- Prior art keywords
- group
- gram
- spp
- formula
- optional
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims description 50
- 244000078703 ectoparasite Species 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 241001465754 Metazoa Species 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 claims abstract description 5
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 241001414987 Strepsiptera Species 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 125000004122 cyclic group Chemical class 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 abstract description 5
- 241000238876 Acari Species 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- -1 acetenyl Chemical group 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000002585 base Substances 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000460 chlorine Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 229910052799 carbon Inorganic materials 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 229910052731 fluorine Inorganic materials 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
- 229910052801 chlorine Inorganic materials 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
- 239000011737 fluorine Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 14
- 150000001721 carbon Chemical group 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229940093499 ethyl acetate Drugs 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 11
- 150000002367 halogens Chemical class 0.000 description 11
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 10
- 208000035126 Facies Diseases 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 125000004414 alkyl thio group Chemical group 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 8
- 239000012024 dehydrating agents Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 7
- NHZLLKNRTDIFAD-UHFFFAOYSA-N 2,5-dihydro-1,3-oxazole Chemical compound C1OCN=C1 NHZLLKNRTDIFAD-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000002671 adjuvant Substances 0.000 description 7
- 239000003513 alkali Substances 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 239000002562 thickening agent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 241000790917 Dioxys <bee> Species 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 238000004040 coloring Methods 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229940102223 injectable solution Drugs 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 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 5
- 238000009826 distribution Methods 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 150000002191 fatty alcohols Chemical class 0.000 description 5
- 230000000977 initiatory effect Effects 0.000 description 5
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 230000002335 preservative effect Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 235000010980 cellulose Nutrition 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 241000272525 Anas platyrhynchos Species 0.000 description 3
- 241000359266 Chorioptes Species 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 241001674048 Phthiraptera Species 0.000 description 3
- 241001481703 Rhipicephalus <genus> Species 0.000 description 3
- 241000509427 Sarcoptes scabiei Species 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 210000003323 beak Anatomy 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 230000008676 import Effects 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 244000144972 livestock Species 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 150000002918 oxazolines Chemical class 0.000 description 3
- 230000035479 physiological effects, processes and functions Effects 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 238000012805 post-processing Methods 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000013049 sediment Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 150000007984 tetrahydrofuranes Chemical class 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-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
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- TXUFIGBVDCUITR-UHFFFAOYSA-N 2-amino-2-(4-tert-butylphenyl)ethanol Chemical compound CC(C)(C)C1=CC=C(C(N)CO)C=C1 TXUFIGBVDCUITR-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 2
- VPMAWSAODAKKSI-UHFFFAOYSA-N 3-chloroprop-2-enoyl chloride Chemical compound ClC=CC(Cl)=O VPMAWSAODAKKSI-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000304153 Auchmeromyia Species 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000257160 Calliphora Species 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 241001124179 Chrysops Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 241001128004 Demodex Species 0.000 description 2
- 241001480824 Dermacentor Species 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 241000371383 Fannia Species 0.000 description 2
- 241001660203 Gasterophilus Species 0.000 description 2
- 241000257324 Glossina <genus> Species 0.000 description 2
- 241000790933 Haematopinus Species 0.000 description 2
- 241000771999 Hippobosca Species 0.000 description 2
- 241000257176 Hypoderma <fly> Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001467800 Knemidokoptes Species 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 229920000881 Modified starch Polymers 0.000 description 2
- 241000581988 Muscina Species 0.000 description 2
- 241001373727 Myobia Species 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical class CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 241001084186 Neotrombicula Species 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 241000932963 Philopteridae Species 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000517309 Pthirus Species 0.000 description 2
- 241000257190 Sarcophaga <genus> Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241001259047 Trichodectes Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- VSQUZVLNMULDCY-UHFFFAOYSA-N [O].C1=CC=NC=C1 Chemical compound [O].C1=CC=NC=C1 VSQUZVLNMULDCY-UHFFFAOYSA-N 0.000 description 2
- DWDAZFJBSZTCCM-UHFFFAOYSA-N [O]C1CCCCC1 Chemical compound [O]C1CCCCC1 DWDAZFJBSZTCCM-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 230000009514 concussion Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 239000012973 diazabicyclooctane Substances 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
- 230000029087 digestion Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000012173 estrus Effects 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 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 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 235000019426 modified starch Nutrition 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- OXGBCSQEKCRCHN-UHFFFAOYSA-N octadecan-2-ol Chemical compound CCCCCCCCCCCCCCCCC(C)O OXGBCSQEKCRCHN-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000003182 parenteral nutrition solution Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000004550 soluble concentrate Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 230000007480 spreading Effects 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- 239000000080 wetting agent Substances 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
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- JFPCQBWUOJIHLS-UHFFFAOYSA-N 1,1,3,3,3-pentachloro-2-fluoroprop-1-ene Chemical group ClC(Cl)=C(F)C(Cl)(Cl)Cl JFPCQBWUOJIHLS-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- WGYZMNBUZFHYRX-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-ol Chemical compound COCC(C)OCC(C)O WGYZMNBUZFHYRX-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(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
- LZILFXHGPBJADI-UHFFFAOYSA-N 2-(2-hydroxypropoxy)propan-1-ol;nonanoic acid Chemical compound CC(O)COC(C)CO.CCCCCCCCC(O)=O LZILFXHGPBJADI-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
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000934067 Acarus Species 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000238679 Amblyomma Species 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241001427556 Anoplura Species 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- 241001480748 Argas Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- UIBGMVGOKJXTGD-UHFFFAOYSA-N C1(=CC=CC=C1)S.C(C)(C)(C)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)S.C(C)(C)(C)C1=CC=CC=C1 UIBGMVGOKJXTGD-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
- 241000282836 Camelus dromedarius Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241001098608 Ceratophyllus Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 241000258922 Ctenocephalides Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 241000268912 Damalinia Species 0.000 description 1
- 241001481694 Dermanyssus 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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241001549210 Echidnophaga Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000322646 Felicola Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000257224 Haematobia Species 0.000 description 1
- 241000562485 Haematobosca Species 0.000 description 1
- CMBYOWLFQAFZCP-UHFFFAOYSA-N Hexyl dodecanoate Chemical group CCCCCCCCCCCC(=O)OCCCCCC CMBYOWLFQAFZCP-UHFFFAOYSA-N 0.000 description 1
- 241001480803 Hyalomma Species 0.000 description 1
- 241000238729 Hydrotaea Species 0.000 description 1
- 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 1
- 241001495069 Ischnocera Species 0.000 description 1
- AXISYYRBXTVTFY-UHFFFAOYSA-N Isopropyl tetradecanoate Chemical class CCCCCCCCCCCCCC(=O)OC(C)C AXISYYRBXTVTFY-UHFFFAOYSA-N 0.000 description 1
- 241000238681 Ixodes Species 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 241000692237 Lipoptena Species 0.000 description 1
- 241000257162 Lucilia <blowfly> Species 0.000 description 1
- 241000771995 Melophagus Species 0.000 description 1
- 241000322738 Menacanthus Species 0.000 description 1
- 241000699673 Mesocricetus auratus Species 0.000 description 1
- 241001481698 Mesostigmata Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000257229 Musca <genus> Species 0.000 description 1
- 241001535851 Myocoptes 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
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 241000772415 Neovison vison Species 0.000 description 1
- 241000562097 Notoedres Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000238887 Ornithodoros Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000790250 Otodectes Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 241000517325 Pediculus Species 0.000 description 1
- 241000009328 Perro Species 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241001649229 Psoroptes Species 0.000 description 1
- 241001675082 Pulex Species 0.000 description 1
- 241001194723 Rhinoestrus Species 0.000 description 1
- 241000304160 Sarcophaga carnaria Species 0.000 description 1
- 241000509416 Sarcoptes Species 0.000 description 1
- 241000555745 Sciuridae Species 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241000044136 Solenopotes Species 0.000 description 1
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241001494139 Stomoxys Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- 241000255626 Tabanus <genus> Species 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 241000790999 Trinoton Species 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 241000061203 Werneckiella Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000005108 alkenylthio group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004176 ammonification Methods 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- YAVVGPBYBUYPSR-UHFFFAOYSA-N benzene;oxygen Chemical compound [O].C1=CC=CC=C1 YAVVGPBYBUYPSR-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- SMLHHBQGIJMAIM-UHFFFAOYSA-N calcium;2-dodecylbenzenesulfonic acid Chemical compound [Ca].CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O SMLHHBQGIJMAIM-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229940082500 cetostearyl alcohol Drugs 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- DAKOBUIKDCTJEB-UHFFFAOYSA-L disodium;propanoate Chemical compound [Na+].[Na+].CCC([O-])=O.CCC([O-])=O DAKOBUIKDCTJEB-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 description 1
- 229960000655 ensulizole Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005368 heteroarylthio group Chemical group 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 229940089456 isopropyl stearate Drugs 0.000 description 1
- 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 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 230000024241 parasitism Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000001944 prunus armeniaca kernel oil Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- WQQPDTLGLVLNOH-UHFFFAOYSA-M sodium;4-hydroxy-4-oxo-3-sulfobutanoate Chemical class [Na+].OC(=O)CC(C([O-])=O)S(O)(=O)=O WQQPDTLGLVLNOH-UHFFFAOYSA-M 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical group [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
-
- 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
- A01N43/74—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 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/424—Oxazoles condensed with heterocyclic ring systems, e.g. clavulanic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
本发明涉及式(Ⅰ)化合物防治人和动物上的昆虫和单食蜱的应用,其中B代表任选取代的烷基、链烯基、环烷基、环烯基、芳基,A代表芳基、芳氧基、杂芳基、杂芳氧基,它们均任选被取代且任选经二价基团Z键合于噁唑啉环,R代表氢或与A和相邻的C原子一起代表螺环状的3-至6-元环,所述的环可以任选含有一或多个来自于O、S、N组的杂原子且它任选稠合上另一个环,该环系任选被取代。
Description
本发明涉及防治体外寄生虫的噁唑啉类的应用和包含噁唑啉类的杀体外寄生虫组合物。
噁唑啉类及其制备和在植物保护上作为杀虫剂和杀螨剂以及防治某些动物上的螨虫的应用业已公开。但尚未公开它们防除体外寄生虫,特别是防除昆虫和单食性蜱的应用。
本发明涉及式(I)化合物防治人和动物体上的寄生昆虫和单食性蜱的应用其中B 代表任选取代的烷基、链烯基、环烷基、环烯基、芳基,A 代表芳基、芳氧基、杂芳基、杂芳氧基,它们均任选被取代且任选经二价基团Z键合于噁唑啉环,R 代表氢或与A和相邻的C原子一起代表螺环状的3-至6-元环,所述的环可以任选含有一或多个来自于O、S、N组的杂原子且它任选稠合上另一个环,该环系任选被取代。
式(I)化合物是例如下列专利申请的主题物质:
WO 93/21 165,WO 93/24470,JP-OS H4 89 484,JP-OS H6 145 155,
JP-OS H6 145 169,JP-OS H6 100 546;JP-OS H6 100 560,JP-OS H6 73 030,
EP-OS 345 775,EP-OS 432 661,EP-OS 553 623,WO 93/22 297,WO 93/25 079.
因此,详细的资料参见在这些申请中的优选化合物组和单独的化合物以及制备方法。
可以优选提到的通式(I)化合物是那些其中取代基具有如下含意的化合物:通式中的任选取代的烷基,单独或作为基团的组成,是具有优选1至20个,特别是1至18个碳原子的直链或支链烷基。下列是可以举例且是优选提到的:任选取代的甲基、乙基、正-或异丙基、正-、异-和叔丁基、新戊基、十一烷基、十二烷基、十五烷基、十八烷基。通式中的任选取代的链烯基和基团例如任选取代的链烯氧基和链烯硫基的链烯基部分,是具有优选2至6个,特别是2至4个碳原子的直链或支链链烯基。下列是可以举例且是优选提到的:乙烯基、丙烯-1-基、丙烯-2-基和丁烯-3-基。通式中的任选取代的炔基和基团例如任选取代的炔氧基和炔硫基的炔基部分,是具有优选2至6个,特别是2至4个碳原子的直链或支链炔基。下列是可以举例且是优选提到的:乙炔基、丙炔-1-基、丙炔-2-基和丁炔-3-基。通式中的任选取代的环烷基,单独或作为基团的组成,是具有优选3至10个,特别是3、5或6个碳原子的单-、二-和三环状环烷基。下列是可以举例且是优选提到的:任选取代的环丙基、环丁基、环戊基、环己基。通式中的任选取代的烷氧基,单独或作为基团的组成,是具有优选1至6个,特别是1至4个碳原子的直链或支链烷氧基。下列是可以举例且是优选提到的:甲氧基、乙氧基、正-和异丙氧基和正-、异-和叔丁氧基。通式中的任选取代的烷硫基,单独或作为基团的组成,是具有优选1至6个,特别是1至4个碳原子的直链或支链烷硫基。下列是可以举例且是优选提到的:甲硫基、乙硫基、正-和异丙硫基和正-、异-和叔丁硫基。通式中的任选取代的烷氧羰基,单独或作为基团的组成,是具有优选2至7个,特别是2至5个碳原子的直链或支链烷氧羰基。下列是可以举例且是优选提到的:甲氧羰基、乙氧羰基、正-和异丙氧羰基和正-、异-和叔丁氧羰基。通式中的卤代烷基,单独或作为基团例如卤代烷氧基或卤代烷硫基的组成,含有1至4个,特别是1或2个碳原子且优选1至5个,特别是1至3个相同或不同的卤原子,优选的卤原子是氟、氯和溴,特别是氟和氯。可以提到的实例是三氟甲基、氯二氟甲基、溴甲基、2,2,2-三氟乙基和五氟乙基。通式中的任选取代的芳基,单独或作为基团例如芳氧基、芳硫基、芳烷基的组成,优选的是任选取代的苯基或萘基,特别是苯基。通式中的任选取代的芳烷基是这样的芳烷基,它在芳基部分(优选苯基或萘基,特别是苯基部分)具有优选6或10个,特别是6个碳原子和在烷基部分具有优选1至4个,特别是1或2个碳原子,烷基部分可以是直链或支链的,该芳烷基可以任选取代在芳基部分和/或烷基上。下列是可以举例且是优选提到的:任选取代的苄基和苯乙基。通式中的任选取代的杂芳基,单独或作为基团如杂芳氧基、杂芳硫基或杂芳烷基是符合休克尔定律芳族原则的5-至7-元环,该环具有优选1至3个,特别是1或2个相同或不同的杂原子。杂原子是氧、硫或氮。下列是可以举例且是优选提到的:任选取代的噻吩基。
通式(I)的任选取代的基团可以具有一或多个,优选1至3个,特别是1或2个相同或不同的取代基。下列取代基是可以举例且是优选提到的:具有优选1至20个,特别是1至18个碳原子的烷基,如甲基、乙基、正-或异丙基和正-、异-和叔丁基、新戊基、十六烷基、十八烷基;具有优选1至14个,特别是1至4个碳原子的烷氧基,如甲氧基、乙氧基、正-和异丙氧基和正-、异-和叔丁氧基;具有优选1至4个,特别是1或2个碳原子的烷硫基,如甲硫基、乙硫基、正-或异丙硫基和正-、异-和叔硫基;具有优选1至4个,特别是1或2个碳原子和优选1至5个相同或不同,特别是1至3个卤原子(卤原子相同或不同且优选是氟、氯或溴,特别是氟)的卤代烷基,如二氟甲基或三氟甲基;羟基;卤素,优选氟、氯、溴,特别是氟、氯;氰基;硝基;氨基;每个烷基基团具有优选1至4个,特别是1或2个碳原子的单烷基-和二烷基氨基,如甲基氨基、甲基乙基氨基,正-和异丙基氨基和甲基正丁基氨基;酰基基团,如甲酰基,烷基羰基,如乙酰基,芳基羰基,如苯甲酰基;羧基;具有优选2至4个,特别是2或3个碳原子的羧基,如甲氧羰基和乙氧羰基;具有1至4个,特别是1至2个碳原子的烷基亚磺酰基,具有1至4个,特别是1或2个碳原子和1至5个卤原子的卤代烷基亚磺酰基,如三氟甲基亚磺酰基;磺酰基(-SO3H);具有优选1至4个,特别是1或2个碳原子的烷基磺酰基,如甲磺酰基和乙磺酰基;具有1至4个,特别是1至2个碳原子和1至5个卤原子的卤代烷基磺酰基,如三氟甲基磺酰基、全氟-叔-、正、仲-丁基磺酰基;具有优选6或10个芳基碳原子的芳基磺酰基,如苯磺酰基;酰基;芳基;芳氧基;杂芳基;杂芳氧基;它本身可以具有上述取代基之一;和亚胺甲基基团
可以优选提到的式(I)化合物是那些其中取代基具有下列含意的化合物:
B 代表C1-C8-烷基,它任选单或多取代:由选自由卤素、氰基、
C1-C4-烷氧基组成的系列的相同或不同的取代基和由苯基、苯氧
基、苄氧基、苯硫基和苄硫基,芳族基团各任选由选自由下列组成
的系列的相同或不同的取代基单至三取代:卤素、C1-C4-烷基、
C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷
硫基和/或C1-C4-卤代烷硫基;
或代表C2-C8-链烯基,它任选由相同或不同的卤素取代基单或多取
代;
或代表C3-C8-环烷基,它任选由来自于由下列组成的系列的相同或
不同的取代基单或多取代:卤素、C1-C4-烷基、C2-C4-链烯基、
C1-C4-卤代烷基或C2-C4-卤代链烯基;
或代表C5-C7-环烯基,它任选由来自于由下列组成的系列的相同或
不同的取代基单或多取代:卤素、C1-C4-烷基或C1-C4-卤代烷基;
或代表苯基,它任选由相同或不同的取代基单至四取代,可以提到
的取代基是卤素,
C1-C4-烷基,
C1-C4-烷氧基-C1-C4-烷基,
C1-C4-卤代烷氧基,
C1-C4-卤代烷基,
C1-C4-烷氧基,它任选间入另1-3个氧原子,
C1-C4-烷硫基,
C1-C4-卤代烷硫基。A 代表苯基、苄基、苯乙-1-基、苯乙-2-基、苯氧基甲基、苯硫基甲基、
苯氧基乙-1-基、苯硫基乙-1-基、苯氧基乙-2-基和苯乙烯基,它们各
任选由相同或不同的取代基单至四取代,就每种情况下可以提到的
适合的苯基取代基是:
C1-C18-烷基,
C1-C8-烷氧基-C1-C8-烷基,
C1-C8-卤代烷氧基,
C1-C4-卤代烷基,
C1-C18-烷氧基,它任选间入另1-3个氧原子,
C1-C18-烷硫基,
C1-C8-卤代烷硫基,
3,4-二氟亚甲基二氧基,
3,4-四氟亚乙基二氧基,
苄基亚氨基氧基甲基,它任选由C1-C4-烷基、C3-C6-环烷基和/或
卤素取代,
环己基和环己基氧基,它们各任选由C1-C6-烷基、C1-C6-烷氧基、
环己基或苯基取代;
吡啶氧基,它任选由来自于由下列组成的系列的相同或不同的取代
基单或二取代:卤素、C1-C4-烷基或C1-C4-卤代烷基;
苯基、苄基、苯氧基、苯硫基、苄氧基和苄硫基,它们各任选由来
自于由下列组成的系列的相同或不同的取代基单至三取代:C1-
C12-烷基、卤素、C1-C4-卤代烷基、C1-C6-烷氧基、C1-C6-卤代
烷氧基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷氧基-亚乙基氧
基、C1-C6-烷硫基和/或C1-C6-卤代烷硫基。R 优选代表氢。
可以特别优选提到的式(I)化合物是那些取代基具有下列含意的化合物:B 代表C1-C6-烷基,它任选单或多取代:由来自于由氟、氯、溴、氰基、C1-C2-烷氧基组成的系列的相同或不同的取代基和由苯基、苯氧基、苄氧基、苯硫基和苄硫基,芳族基团各任选由来自于由下列组成的系列的相同或不同的取代基单或二取代:氟、氯、C1-C4-烷基、C1-C2-卤代烷基、C1-C2-烷氧基、C1-C2-卤代烷氧基、C1-C2-烷硫基和/或C1-C2-卤代烷硫基;或代表C2-C6-链烯基,它任选由来自于由氟、氯和/或溴组成的系列的相同或不同的取代基单或多取代;或代表C3-C8-环烷基,它任选由来自于由下列组成的系列的相同或不同的取代基单或多取代:氟、氯、C1-C4-烷基、C2-C4-链烯基、带有氟和/或氯作为卤原子的C1-C2-卤代烷基和带有氟和/或氯作为卤原子的C2-C4-卤代链烯基;或代表C5-C7-环烯基,它任选由来自于由下列组成的系列的相同或不同的取代基单或多取代:氟、氯、C1-C4-烷基和带有氟和/或氯作为卤原子的C1-C2-卤代烷基;或代表苯基,它任选由相同或不同的取代基单至四取代,可以提到的取代基是氟、氯、溴,C1-C4-烷基,C1-C4-烷氧基,它由相同或不同的F和/或Cl取代基单至六取代,C1-C2-烷基,它由相同或不同的F和/或Cl取代基单至五取代。A 特别优选代表苯基、苄基、苯乙-1-基、苯乙-2-基、苯氧基甲基、苯硫基甲基、苯氧基乙-1-基、苯氧基乙-2-基、苯硫基乙-1-基和苯乙烯基,它们各任选由相同或不同的取代基单至四取代,就每种情况下可以提到的适合的苯基取代基是:F、Cl、Br,C1-C18-烷基,C1-C6-烷氧基-C1-C8-烷基,
C1-C8-烷氧基,它由相同或不同的F和/或Cl取代基单至六取代,
C1-C2-烷基,它由相同或不同的F和/或Cl取代基单至五取代,
C1-C18-烷氧基和-(OC2H4)1-3-O-C1-C6-烷基,
C1-C12-烷硫基,
C1-C8-烷硫基,它由相同或不同的F和/或Cl取代基单至六取代,
3,4-二氟亚甲基二氧基,
3,4-四氟亚乙基二氧基,
环己基和环己基氧基,它们各任选由C1-C4-烷基、C1-C4-烷氧基,
环己基或苯基取代;
吡啶氧基,它任选由相同或不同的F、Cl或CF3取代基单或二取
代;
苯基、苄基、苯氧基、苯硫基、苄氧基和苄硫基,它们各任选由来
自于由下列组成的系列的相同或不同的取代基单至三取代:C1-
C12-烷基、F、Cl、Br、CF3、C1-C4-烷氧基、由相同或不同
的F和/或Cl取代基单至六取代的C1-C4-烷氧基、C1-C4-烷氧基-
C1-C4-烷基、C1-C4-烷氧基-亚乙基氧基、C1-C4-烷硫基、或由相
同或不同的F和/或Cl取代基单至六取代的C1-C6-烷硫基。R 特别优选代表氢。
表2
(R2)m | (R2)m |
H | 2-CH3 |
2-Cl | 2-OCH3 |
2-F | 2,3-Cl2 |
3-Cl | 2,6(-OC2H5)2 |
2,6-Cl2 | 3-CH3 |
3,5-Cl2 | 3,5(-OCH3)2 |
3,5-F2 | 3-OC6H5 |
2,5-Cl2 | |
3,5-Cl2;2-F | 与R1一起代表 |
2,3-F2 | 3,4(-OCF2O-) |
2,5-F2 | 3,4(-OCF2CF2O-) |
2,3,5,6-Cl4 | 2-Cl;3-CF3 |
3-CF3 | 2-Cl;5-CF3 |
(表1a,续)
(表1a,续)
再则,A可以代表下述式a197其中E 代表任选取代的烷二基,且X 代表氢或卤素。
可以优选提到下列烷二基基团E:
E1 -CF2- E2 -CF(CCl2CF3)-
E3 -CFCl- E4 -CF2-CF2-
E5 -CF(CH3)- E6 -CF2-CFCl-
E7 -C(CH3)(CH2F)- E8 -CF2-CF(CH3)-
E9 -C(CH3)(CH2Cl)- E10 -CF2-C(CH3)2-
E11 -C(CF3)(CHClCF3) E12 -CFCl-CFCl-
E13 -CH(CH2CF3)- E14 -CF2-CH(CH3)-
E15 -CH(CHClCF3)- E16 -CF2-CH(CF3)-
下列基团是可以举例提到的取代基B下列基团是可以举例提到的取代基B下列含意是可以举例提到的二价基团Z:-CH2-,-CH(CH3)-,-CH2CH2-,-CH=CH-,-CH2O-,-CH2S-,-CH(CH3)S-,-CH(CH3)O-,-CH2CH2O-,-CH2S(O)-,-CH2-SO2-.
B-COOH (III)其中B 具有上述含意;或b)如果适宜在稀释剂存在下,使式(IV)的酰氨基醇与脱水剂反应,其中A、B和R具有上述含意;或c)如果适宜在稀释剂存在下,使式(V)的酰胺衍生物与碱反应,其中A、B和R具有上述含意;且X 代表离去基团如卤素、烷基磺酰基氧基或芳基磺酰基氧基。
在制备式(I)化合物的方法(a)中用作起始原料的氨基醇是已知的和/或可以通过本身已知的方法,用还原相应的氨基酸的方式来制备(参见,《杂环》[Heterocycles]9(1978),1277-1285;《有机化学杂志》[J.Org.Chem.] 43(1978),2539-2541;Liebigs Ann.Chem.1980,122-139;《四面体通讯》[Tetrahedron Lett.],26(1985),4971-4974)。
同样在制备式(I)化合物的方法(a)中用作起始原料的式(III)羧酸是用于有机合成的已知化学品,或可以用本身已知的方法制备。
方法(a)和(b)是使用脱水剂进行的。可以采用的物质是有机化学中的常见脱水剂。下列是可以优选的:硫酸、多磷酸(PPA)、氧化磷(V)、二环己基碳化二亚胺(DCC)、硫化磷(V)和三苯基膦/三乙胺/四氯化碳体系。
进行本发明方法(a)至(c)的稀释剂是常规有机溶剂。下列是可以优选使用的:脂族、脂环族或芳族的任选卤代的烃如汽油、苯、甲苯、二甲苯、氯苯、二氯苯、石油醚、己烷、环己烷、二氯甲烷、氯仿、四氯化碳;醚类如乙醚、二异丙醚、二噁烷、四氢呋喃或乙二醇二甲醚或乙二醇二乙醚;醚类,如丙酮、丁酮或甲基异丁基酮;腈类,如乙腈、丙腈或苯甲腈;酰胺类,如N,N-二甲基甲酰胺和N,N-二甲基乙酰胺、N-甲基-吡咯烷酮或六甲基磷酰三胺;酯类,如乙酸甲酯或乙酸乙酯,和亚矾类,如二甲基,也任选醇类,如甲醇或乙醇。
进行本发明方法(a)时,反应温度可以在大范围内变化。通常,该方法是在0℃至150℃间的温度,优选在10℃和100℃间的温度下进行。
本发明方法(a)通常在常压下进行。然而,也可以在增压或减压下,通常在0.1巴至10巴下进行。
进行本发明方法(a)时,在每一种情况下所需的起始原料通常采用大致等摩尔。然而,在每一种情况下,也可以相对大量过量地使用二种组份之一。通常,反应可以在适合的稀释剂和在脱水剂存在下进行,且反应混合物是在各自所需的温度下搅拌几小时。后处理是通过常规方法进行的。
在本发明方法(a)的具体实施方案中,也可以采用相应的腈来代替式(III)的羧酸,在这种情况下,优选使用催化剂例如氯化锌(II)来代替脱水剂。
在制备式(I)化合物的方法(b)中用作起始原料的酰氨基醇是已知的和/或可以通过本身已知的方法来制备。
式(IV)的酰氨基醇是如下获得的:例如,在酸结合剂和在稀释剂存在下,在0℃至100℃下,使由式(III)羧酸衍生的酰基氯与式(II)的氨基醇反应。酸结合剂是例如三乙胺、吡啶、碳酸钾、氢氧化钠或叔丁醇钾,稀释剂是例如甲苯、氯苯、丙酮或乙腈。
大多数由式(III)羧酸衍生的酰基氯是已知的和/或可以通过本身已知的方法来制备,例如,如果适宜在稀释剂存在下,使式(III)的羧酸与卤化剂如亚硫酰氯反应。
例如,式(VI)的α-氟-β,β-二氯-丙烯酰氯可以通过如果适宜在催化剂存在下,水解2-氟-1,1,3,3,3-五氯丙烯而获得。适合的催化剂是路易斯酸、无机酸及其酸盐,例如三氯化铁、三氟化硼、硫酸、盐酸、硫酸氢钾、硫酸氢钠及其它。
取决于反应的条件(例如,在反应混合物中酰基氯的存留时间)和加入的水量,主要形成的α-氟-β,β-二氯-丙烯酰氯中的一部分任选水解成相应的丙烯酸,该丙烯酸可以随后再转化成酰基氯,例如通过与亚硫酰氯反应。
进行方法(b)时,反应温度可以在大范围内变化。通常,该方法是在-20℃至+150℃间的温度,优选在0℃和100℃间的温度下进行。
本发明方法(b)通常在常压下进行。然而,也可以在增压或减压下,通常在0.1巴至10巴下进行。
进行制备式(I)化合物的本发明方法(b)时,每摩尔的式(IV)酰氨基醇通常采用1至20摩尔,优选1至5摩尔的脱水剂。
在本发明方法(b)的优选实施方案中,将式(IV)的酰氨基醇导入稀释剂中,且之后计量入脱水剂。将反应混合物在所需的温度下搅拌,直到反应结束,随后用常规的方式后处理。
在制备式(I)化合物的方法(c)中用作起始原料的酰胺衍生物是已知的和/或可以通过本身已知的方法来制备。
式(V)的酰胺衍生物如下获得:如果适宜在碱存在下,且如果适宜在稀释剂存在下,用常规的方法,使式(IV)的酰氨基醇与氯化剂如亚硫酰氯或氯化磷(V)反应,或与磺酰化试剂如甲磺酰氯或对甲苯磺酰氯反应。
方法(c)是在碱存在下进行的。适合的碱是所有常规的无机或有机碱。下列是可以优选使用的:碱金属或碱土金属的氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐,例如氢化钠、氨化钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、氢氧化铵、乙酸钠、乙酸钾、乙酸钙、乙酸铵、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠或碳酸铵,以及叔胺,如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、吡啶、N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)或二氮杂二环十一碳烯(DBU)。
进行方法(c)时,反应温度可以在大范围内变化。通常,该方法是在-20℃至+150℃间的温度,优选在0℃和100℃间的温度下进行。
本发明方法(c)通常在常压下进行。然而,也可以在增压或减压下,通常在0.1巴至10巴下进行。
进行制备式(I)化合物的本发明方法(c)时,每摩尔的式(V)酰胺衍生物通常采用1至3摩尔,优选1.0至1.5摩尔的碱。
在方法(c)的优选实施方案中,将式(V)的酰胺衍生物与碱在稀释剂中混合中;将反应混合物在所需的温度下搅拌,直到反应结束,随后用常规的方式后处理。
本发明活性化合物对温血动物毒性低,可用于防治动物害虫,如出现在动物饲养和牲畜繁育中、在生产性牲畜、繁育动物、动物园动物、实验室动物、试验动物和宠物上的昆虫、单食性蜱。本发明活性化合物对害虫发育的所有或各个阶段都有活性,对抗性品系及正常敏感品系具有活性。
防治动物害虫的目的是为了防止疾病和疾病的传染、死亡和降低产量(例如在产肉、产奶、产毛、产皮、产蛋等中),以便达到活性化合物的使用使得更经济和更简单的动物饲养成为可能。
这些害虫包括:虱目,例如,血虱属(Haematopinus spp.)、颚虱属(Linognathusspp.)、盲虱属(Solenopotes spp.)、虱属(Pediculus spp.)、阴虱属(Pthirus spp.)。食毛目,例如,毛鸟虱属(Trimenopon spp.)、短角鸟虱属(Menoponspp.)、Eomenacanthus spp.、Menacanthus app.、啮毛虱属(Trichodectes spp.)、felicola spp.、畜虱属(Damalinea spp.)、Bobiola spp.、Trinoton spp.、Werneckiella spp.、Lepikeutronspp.。双翅目,例如,斑虻属(Chrysops spp.)、虻属(Tabanus spp.)、蝇属(Musca spp.)、Hydrotaea spp.、腐蝇属(Muscina spp.)、Haematobosca spp.、血蝇属(Haematobia spp.)、螫蝇属(Stomoxysspp.)、厕蝇属(Fannia spp.)、舌蝇属(Glossina spp.)、绿蝇属(Luciliaspp.)、丽蝇属(Calliphora spp.)、火蝇属(Auchmeromyia spp.)、Cardylobia spp.、Cochiomyia spp.、金蝇属(Chrysomyia spp.)、麻蝇属(Sarcophaga spp.)、肉蝇属(Wohlfartia spp.)、胃蝇属(Gastrophilus spp.)、Oesteromyia spp.、Oedemagena spp.、皮蝇属(Hypoderma spp.)、狂蝇属(Oestrus spp.)、鼻狂蝇属(Rhinoestursspp.)、羊虱蝇属(Melophagus spp.)、虱蝇属(Hippobosca spp.)。蚤目,例如,栉头蚤属(Ctenocephalides spp.)、Echidnophaga spp.、毛列蚤属(Ceratophyllus spp.)、蚤属(Pulex spp.)。寄生性蜱,下列属和种类:眼玻蜱属(Hyalomma spp.)、扇头蜱属(Rhipicephalus spp.)、牛蜱属(Boophilus spp.)、花蜱属(Amblyommaspp.)、革蜱属(Dermacentor spp.)、硬蜱属(Ixodes spp.)、隐喙蜱属(Argas spp.)、钝喙蜱属(Ornithodorus spp.)、残喙蜱属(Otabiusspp.);中气门亚目,刺皮螨属(Dermanyssus spp.)、肺刺螨属(Pneumonyssusspp.)。前气门亚目,姬螯螨属(Cheyletiella spp.)、绵羊疥螨属(Psorergatesspp.)、肉螨属(Myobia spp.)、脂螨属(Demodex spp.)、新恙螨属(Neotrombicula spp.);无气孔亚目,例如,粉螨属(Acarus spp.)、Myocoptes spp.、瘙螨属(Psoroptes spp.)、皮螨属(Chorioptes spp.)、Otodectes spp.、疥螨属(Sarcoptes spp.)、Notoedres spp.、鸟疥螨属(Knemidocoptesspp.)、新鸟疥螨属(Neoknemidodoptex spp.)、Lytodites spp.、鸡雏螨属(Laminosioptes spp.)
家养动物和生产性牲畜包括例如牛、绵羊、山羊、马、猪、狗、猫、骆驼、水牛、猴、兔、黄占鹿、驯鹿,皮毛饲养动物诸如水貂、灰鼠、浣熊,鸟类诸如鸡、火鸡、雉、鹅、鸭。
实验室动物和试验用动物包括小鼠、大鼠、豚鼠、金色仓鼠、狗和猫。
宠物包括狗和猫。
可以作预防和治疗方式给药。
活性化合物可以直接或以适当的制剂形式经肠道、非肠道、经皮、经鼻、通过环境处理给药,或借助于包含活性化合物的成形物件如条带、板、箍带、颈圈、耳标、肢箍、标牌物给药。
活性化合物的经肠道例如经口给药,是通过粉剂、栓剂、片剂、胶囊、糊剂、饮剂、粒剂、顿服剂或大丸剂、混药喂食或饮用水等形式。皮肤给药是通过点滴、喷雾、沐浴、冲洗、浇泼和涂药斑和撒药粉形式来实施的。非肠道给药是通过(肌肉、皮下、静脉、腹膜)注射形式或通过输液来实施的。
合适的制剂是:
溶液,如可注射溶液、口服溶液、稀释后可口服的浓缩液,用于皮肤或体腔的溶液,浇泼和点涂制剂,凝胶;
用于口服或皮肤给药和用于注射的乳状液和悬浮液;半固体制剂;
活性化合物掺入软膏基剂或水包油或油包水乳状液基剂的制剂;
固体制剂,如粉剂、预混物或浓缩物、粒剂、丸剂、片剂、大丸剂、胶囊剂;气雾剂和吸入剂,含有活性组份的成形物件。
可注射溶液是经静脉、肌肉和皮下给药。
可注射溶液是通过将活性化合物溶解于适当的溶剂和(如果适宜)加入添加剂(如增溶剂、酸、碱、缓冲盐溶液、抗氧化剂和防腐剂)而制备。溶液过滤消毒并抽出。
下列是可以提到的溶剂:生理可接受的溶剂,如水、醇类(如乙醇、丁醇、苄醇、甘油)、烃、丙二醇、聚乙二醇、N-甲基吡咯烷酮及其混合物。
如果适宜,活性化合物也以溶解于生理可接受的适合于注射的植物油或合成油。
下列是可以提到的增溶剂:能够提高活性组份在主要溶剂中溶解性,或阻止活性组份沉淀的溶剂。实例是聚乙烯吡咯烷酮、聚乙氧基化蓖麻油、聚乙氧基化失水山梨醇酯。
防腐剂包括:苄醇、三氯丁醇、对羟基苯甲酸酯、正丁酯。
口服溶液直接给药。浓缩物在预先稀释到给药浓度后口服。口服溶液和浓缩物按照前面描述的可注射溶液的方法制备,也可能在无菌操作下进行分装处理。
用于皮肤的溶液可以通过点滴、涂刷、用力擦、泼撒、喷雾或通过浸渍(浸醮、沐浴或淋洗)涂用。这些溶液按照前述描述的可注射溶液的方法制备。
制备过程中加入增稠剂或许会是有利的。增稠剂是无机增稠剂(如膨润土、胶态二氧化硅、单硬脂酸铝)、有机增稠剂(如纤维素衍生物,聚乙烯醇及其共聚体,丙烯酸酯及甲基丙烯酸酯)。
将凝胶涂在或刷在皮肤上或导入体腔里。通过向业已按照可注射溶液的方法制备的溶液中加入足够的增稠剂,形成具有霜样粘度的透明物质而制备凝胶。使用的增稠剂是上文提到的增稠剂。
浇泼和点涂制剂浇泼或浇撒到皮肤的限定区域,在这种情况下,活性化合物或是通过皮肤和系统作用渗透或是在身体的表面分散。
浇泼和点涂制剂是通过将活性成分溶解、悬浮和乳化于合适的皮肤可耐受的溶剂或溶剂混合物中来制备。如果适宜的话,也可以加入其它助剂(如着色剂、吸收促进物、抗氧化物、光稳定剂和粘结剂)。
可以提到的溶剂是:水、链烷醇、甘醇类、聚乙二醇、聚丙二醇、甘油、芳族醇(如苯甲醇、苯乙醇、苯氧基乙醇)、酯类(如乙酸乙酯、乙酸丁酯、苯甲酸苄基酯)、醚类(如链烷二醇烷基醚、二丙二醇单甲基醚、二乙二醇单丁基醚)、酮类(如丙酮、甲乙酮)、芳香族和/或脂肪族烃、植物油或合成油、DMF、二甲基乙酰胺、N-二甲基-吡咯烷酮、2,2-二甲基-4-氧基亚甲基-1,3-二氧戊环。
着色剂是所有允许用于家畜且能够溶解或悬浮的着色剂。
吸收促进剂的实施例是DMSO、扩散油(如肉豆蔻酸异丙基酯、二丙二醇壬酸酯、硅氧烷油、脂肪酸酯、甘油三酯、脂肪醇)。
抗氧化剂是亚硫酸盐或偏亚硫酸氢盐如偏亚硫酸氢钾、抗坏血酸、丁基羟基甲苯、丁基羟基苯甲醚、维生素E。
光稳定剂的实例是属于二苯甲酮或苯基苯并咪唑磺酸(navantisolicacid)类的物质。
粘结剂的实例是纤维素衍生物、淀粉衍生物、聚丙烯酸酯、天然聚合物(如藻酸盐、明胶)。
乳液可以经口、经皮肤或以注射液形式给药。
乳液可以是油包水型或水包油型。
它们可按照以下方法制备:通过将活性化合物溶于疏水相或亲水相,借助于乳化剂和(如合适的话)其它辅助剂(如着色剂、吸收促进剂、防腐剂、抗氧化物、光稳定剂、粘度增加物质),将上述相与另一相的溶剂均化。
下列是可以提到的疏水相(油):石蜡油、硅氧烷油、天然植物油(如芝麻油、杏仁油、蓖麻油)、合成甘油三酯如辛酸/癸酸二甘油酯、带有链长C8-12的植物脂肪酸或其它具体选用的天然脂肪酸的三甘油混合物、饱和的或不饱和的部分三甘油脂肪酸混合物(它可以是含羟基的脂肪酸)、C8/C10脂肪酸的单或双甘油酯。
脂肪酸酯(如硬脂酸乙酯、己二酸二正丁酰基酯、月桂酸己基酯、壬酸二丙二醇酯、中等链长的支链脂肪酸与链长C16-C18的饱和脂肪醇的酯、肉豆蔻酸异丙酯、棕榈酸异丙酯、链长C12-C18的饱和脂肪醇的辛酸/癸酸酯、硬脂酸异丙酯、油基油酸酯、癸基油酸酯、乳酸乙酯,蜡质脂肪酸酯如合成的鸭油脂(duck preen fat)、邻苯二甲酸二丁基酯及己二酸二异丙基酯,涉及后者的酯混合物等。
脂肪醇如异三癸醇、2-十八烷醇、鲸蜡基硬脂基醇、油醇。
脂肪酸如油酸及其混合物。
下面是可以提到的亲水相:水、醇类如丙二醇、甘油、山梨醇及其混合物。
可以提到的乳化剂包括:非离子型表面活性剂,例如聚氧乙烯化的蓖麻油、聚氧乙烯化的脱水山梨醇单油酸酯、脱水山梨醇单硬酯酸酯、甘油单硬脂酸酯、聚氧乙基硬脂酸酯、烷基苯酚聚乙二醇醚;
两性表面活性剂如N-月桂基-β-亚氨基二丙酸二钠盐或卵磷酯;
阴离子型表面活性剂,如月桂基硫酸钠、脂肪醇醚硫酸盐、单/二烷基聚乙二醇醚正磷酸酯单乙醇胺盐;
阳离子型表面活性剂如鲸蜡基三甲基氯化铵。
下列是可以提到的其他的辅助剂:
增粘物质和稳定乳液的物质:如羧甲基纤维素、甲基纤维素及其它纤维素和淀粉衍生物、聚丙烯酸酯、藻酸盐、明胶、阿拉伯树胶、聚乙烯吡咯烷酮、聚乙烯醇、甲基乙烯醚与顺式丁烯二酐的共聚物、聚乙二醇、蜂蜡、胶态二氧化硅或提到的物质的混合物。
悬浮液可以经口、经皮或以注射液形式给药。悬浮液可通过在赋形剂液体中悬浮活性物质来制备,如果适宜,可添加其它辅助剂(如润湿剂、着色剂、吸收促进剂、防腐剂、抗氧化剂和光稳定剂)。
可以提到的赋形剂液体是所有的均质溶剂和溶剂混合物。
可以提到的润湿剂(分散剂)是上文指明的表面活性剂。
可以提到的其他辅助剂是上文提到的那些。
半固体制剂可以经口或经皮给药。它们不同于上文提及的悬浮液和乳液仅在于它们有更高的粘度。
制备固体制剂时,将活性化合物与合适的赋形剂混合,如果适宜,加入辅助剂,并将混合物按照需要加工。
可以提到的赋形剂是所有生理可接受的固体惰性物质。这类适合的物质是无机和有机物质。无机物质的实例是氯化钠、碳酸盐(如碳酸钙)、碳酸氢盐、氧化铝、硅石、矾土、沉淀的或胶状的二氧化硅和磷酸盐。
有机物质的实例是糖、纤维素、食物和动物饲料(如奶粉、动物粉、谷物粉和粗谷粉和淀粉)。
辅助剂是上文已经列出的防腐剂、抗氧化剂和着色剂。
其它合适的辅助剂是润滑剂和glidants,例如硬脂酸镁、硬脂酸、滑石、膨润土,崩解促进剂如淀粉或交联聚乙烯吡咯烷酮,粘合剂例如淀粉、明胶或直链聚乙烯吡咯烷酮,和干粘合剂如微晶纤维素。
在制剂中,活性化合物也可作为与增效剂或其它活性物的混合物形式存在。
直接可用的制剂包含浓度为10ppm到按重量计20%,优选按重量计0.1到10%的活性化合物。
使用前稀释的制剂包含浓度为按重量计0.5-90%,优选按重量计1-50%的活性化合物。
通常每天每公斤体重施用大约1-100mg活性化合物对达到有效的结果明显会是有利的。
采用于下列实施例中的活性化合物(I)是下式的化合物:2-(2,6-二氟苯基)-4-[4-(4-三氟甲氧基苯基)-苯基]-2-噁唑啉。实施例1SC(悬浮剂)制剂:368克 活性化合物135克 乳化剂环氧乙烷和环氧丙烷的嵌段共聚物12克 二甲苯基醚磺酸酯/甲醛缩合物(乳化剂)3.5克 水溶性聚乙烯醇58.0克 氯化铵116.0克 尿素1.2克 浓度37%的盐酸4.6克 黄原胶560.5克 蒸馏水实施例2WP(可分散粉剂)制剂:25.0克 活性化合物11.0克 二异丁基-萘磺酸钠10.0克 正十二烷基苯磺酸钙12.0克 含高分散二氧化硅的烷基芳基聚乙二醇醚3.0克 二甲苯基醚磺酸酯/甲醛缩合物(乳化剂)2.0克 Baysilon-E——一种Bayer AG生产的含聚硅氧烷消泡剂,和2.0克 细分散二氧化硅45.0克 高岭土实施例3SL(水溶性浓缩物)制剂:18.3克 活性化合物12.5克 以烷基芳基聚乙二醇醚为基础的天然乳化剂3.5克 二异辛基磺基琥珀酸钠38.4克 二甲基亚砜,和37.5克 2-丙醇实施例4SL(水溶性浓缩物)制剂:185克 活性化合物15.0克 二异丁基-磺基琥珀酸钠,和76.5克 二甲基亚砜与100克由下列组成的香波制剂混合按重量计44.4% Marlon AT50—一种由Hüls AG生产的烷基苯
磺酸的三乙醇胺盐按重量计11.1% Marlon A350 一种由Hüls AG生产的烷基苯
磺酸的钠盐按重量计3.0% 由Hüls AG生产的油酸与二乙醇胺的缩合物按重量计41.5% 聚乙二醇实施例5
由下列组成的喷雾制剂:2.0克 活性化合物110.0克 二甲基亚砜35.0克 2-丙醇,和53.0克 丙酮制备实施例实施例1
伴随搅拌(微放热),将0.3克(6毫摩尔)甲醇钠加入到于50毫升甲醇中的1克(6毫摩尔)4-叔丁基苯硫酚中。将于30毫升甲醇中的2.1克(6毫摩尔)2-(2,6-二氟苯基)-4-(对甲苯磺酰氧基甲基)-1,3-噁唑啉在40℃下滴加入到此溶液中。反应混合物在40℃下搅拌2小时,之后于回流下搅拌16小时。之后蒸馏掉溶剂,残留物用100毫升乙酸乙酯处理,并用每次各50毫升水洗涤三次。汽提掉溶剂,使用甲苯/甲苯、乙酸乙酯10∶1作洗脱液,将残留物经硅胶柱色谱色谱纯化。
获得0.9克(理论值的41.6%)2-(2,6-二氟苯基)-4-(4-叔丁基苯硫基甲基)-1,3-噁唑啉,其log P分配系数(辛醇/水)为~4.64,折射指数为nD 20=1.5660。起始化合物的制备实施例1a
将5.6毫升(0.069摩尔)吡啶加入到于100毫升乙酸乙酯中的5.3克(0.023摩尔)2-(2,6-二氟苯基)-4-羟基甲基-1,3-噁唑啉中,随后滴加入于50毫升乙酸乙酯中的4.4克(0.023摩尔)对甲苯磺酰氯。在此期间,温度上升至50℃。在50℃下继续搅拌2.5小时,随后在回流下搅拌8小时。有机相用每次各50毫升水洗涤四次,蒸馏掉溶剂。使用洗脱液甲苯与洗脱液乙酸乙酯的梯度液,将残留物经硅胶柱色谱色谱纯化。
将6.5克(0.0168摩尔)N-[1-氯-3-(4-叔丁基苯甲酰氧基)-2-丙基]-2,6-二氟苯甲酰胺溶解于100毫升甲醇中。加入2毫升(0.033摩尔)浓度45%的氢氧化钠溶液,将混合物回流搅拌4小时。在蒸馏掉溶剂后,将残留物用100毫升乙酸乙酯处理,并用每次各50毫升水洗涤三次,并蒸馏掉溶剂。
获得2.8克(理论值的72%)2-(2,6-二氟苯基)-4-羟基甲基-1,3-噁唑啉,熔点82℃。实施例1c
将9克(0.023摩尔)N-[1-羟基-3-(4-叔丁基苯甲酰氧基)-2-丙基]-2,6-二氟苯甲酰胺悬浮于60毫升四氯化碳中。加入1.7毫升(0.023摩尔)亚硫酰氯,并将混合物回流1.5小时。蒸馏掉溶剂。
获得9.3克N-[1-氯-3-(4-叔丁基苯甲酰氧基)-2-丙基]-2,6-二氟苯甲酰胺,其log P分配系数(辛醇/水)为~3.86。实施例1d
先将21.9ml(0.158摩尔)三乙胺加入到于400毫升乙酸乙酯中的21克2-氨基-3-(4-叔丁基苯甲酰氧基)-1-丙醇盐酸盐中,随后在0℃下,滴加入于20毫升乙酸乙酯中的13.9克2,6-二氟苯甲酰氯。在20℃继续搅拌1小时;用抽吸滤出沉淀物,有机相用每次各100毫升水洗涤三次,蒸馏掉溶剂,并将残留物用二异丙醚搅拌。
将于5毫升水中的1.6毫升(0.026摩尔)浓度45%的氢氧化钠滴加入到于100毫升甲醇中的4.3克(0.013摩尔)N-[2-氯-1-(4-叔丁基苯基)-乙基]-2,2-双(氟甲基)-丙酰胺中。将反应混合物于回流下继续搅拌1小时,并随后将混合物通过蒸馏掉溶剂来浓缩。残留物用水搅拌,抽吸滤出沉淀物,并干燥。
获得3.8克(理论值的99%)2-(1,3-二氟-2-甲基-丙-2-基)-4-(4-叔丁基苯基)-1,3-噁唑啉,熔点62-63℃。实施例2的起始化合物的制备实施例2a(步骤1)
将3.3毫升(0.024摩尔)三乙胺加入到于150毫升乙酸乙酯中的3.9克(0.02摩尔)2-氨基-2-(4-叔丁基苯基)-1-乙醇中,随后于0℃下滴加入3.7克(0.024摩尔)2,2-双(氟甲基)-丙酰氯。之后让混合物升至室温,并继续搅拌过夜。随后抽吸滤出沉淀物,滤液用水反复洗涤,并分离出有机相,经硫酸钠干燥,过滤并浓缩。
获得4.5克(理论值的71.9%)N-[2-羟基-1-(4-叔丁基苯基)-乙基]-2,2-双(氟甲基)-丙酰胺,熔点141℃。实施例2b(步骤2)
将1.05克(0.0144摩尔)亚硫酰氯加入到于100毫升四氯化碳中的4.5克(0.0144摩尔)N-[2-羟基-1-(4-叔丁基苯基)-乙基]-2,2-双(氟甲基)-丙酰胺(参见步骤1)中。让反应混合物在反应后回流1小时。在蒸馏掉溶剂后,获得4.3克(理论值的90%)N-[2-氯-1-(4-叔丁基苯基)-乙基]-2,2-双(氟甲基)-丙酰胺,熔点98℃。实施例3
将0.75克(6.7毫摩尔)叔丁醇钾加入到2.0克(5.2毫摩尔)N-[1-(4-叔丁基苯基)-2-氯乙基]-2,3,5,6-四氟苯甲酰胺的30毫升四氯化碳溶液中,并将混合物于50℃下搅拌。3小时后,将反应混合物倒入水中,并用二氯甲烷萃取。有机相用水洗涤,经硫酸镁干燥,随后真空浓缩。残留物通过柱色谱的方式(洗脱液氯仿)纯化。
获得0.8克(理论值的44.7%)4-(4-叔丁基苯基)-2-(2,3,5,6-四氟苯基)-1,3-噁唑啉,其log P分配系数(辛醇/水)为4.70(pH:7.4)。实施例3的起始化合物的制备实施例3a
将2.1克(5.7毫摩尔)N-[1-(4-叔丁基苯基)-2-羟乙基]-2,3,5,6-四氟苯甲酰胺和5毫升亚硫酰氯于50毫升甲苯中回流18小时。随后真空去除过量的亚硫酰氯和溶剂。
获得2.2克(理论值的100%)N-[1-(4-叔丁基苯基)-2-氯乙基]-2,3,5,6-四氟苯甲酰胺,直接进一步反应。实施例3b
将溶解于10毫升二氯甲烷中的1.6克(7.5毫摩尔)2,3,5,6-四氟苯甲酰氯,伴随搅拌,于20℃下,滴加入到1.45克(7.5毫摩尔)2-氨基-2-(4-叔丁基苯基)-乙醇和0.75克(7.5毫摩尔)三乙胺的20毫升二氯甲烷溶液中。在混合物沸腾过夜后,将之用二氯甲烷稀释,用水洗涤,且将有机相真空浓缩。残留物用少量的正戊烷搅拌,并用抽吸滤出。
将3.4克(8.7毫摩尔)2-苯基-5-(2,6-二氯苯甲酰基氨基)-5-羟基甲基-1,3-二噁烷悬浮于50毫升甲苯中,并将悬浮液与2克亚硫酰氯一起在80℃下搅拌24小时。之后在水泵真空下蒸馏掉过量的亚硫酰氯和甲苯。
残留物用50毫升甲苯处理,用0.9克叔丁醇钾处理。之后将反应混合物于50℃下搅拌,并进行薄层色谱检查。当反应完毕时,获得的溶液用水洗涤,且随后将有机相在水泵真空下浓缩。残留物使用环己烷/乙酸乙酯(体积2∶1)作洗脱液在硅胶上色谱。
获得1克(理论值的31%)8-苯基-2-(2,6-二氯苯基)-1-氮杂-3,7,9-三氧杂-螺[4.5]癸-1-烯,熔点158-160℃。实施例4的起始化合物的制备实施例4a
将10毫升三乙胺和10克钯/活性炭加入到于1升乙醇中的104克(0.35摩尔)2-(4-叔丁基苯基)-5-羟基甲基-5-硝基-1,3-二噁烷中,并将混合物在20℃和30巴下氢化3天。之后将之过滤,滤液在水泵真空下浓缩,残留物用正己烷处理,且用此方法获得的晶体产物通过抽吸过滤而分离。
将5毫升三乙胺加入到于80毫升二氯甲烷中的5克(20毫摩尔)2-(4-叔丁基苯基)-5-氨基-5-羟基甲基-1,3-二噁烷中。之后于0℃下滴加入4.5克(20毫摩尔)2,6-二氯苯甲酰氯的5毫升二氯甲烷溶液,并将混合物于20℃下搅拌15小时。随后使用0.5N氢氧化钠溶液洗涤,有机相用硫酸钠干燥,并过滤。滤液用水泵真空浓缩,残留物用正己烷消化而结晶,产物通过抽吸过滤而分离。
将0.67克(2毫摩尔)N-(2-羟基-1-(3,4-二氟亚甲基二氧基-苯基)-乙基)-2,6-二氟苯甲酰胺导入15毫升甲苯中,并在20℃下,加入0.27毫升(4毫摩尔)亚硫酰氯。之后将反应混合物回流3小时。冷却后,将混合物浓缩,残留物用15毫升四氢呋喃处理,在加入0.23克(2毫摩尔)叔丁醇钾后,将混合物在50℃下搅拌1小时。将之浓缩后,残留物用二氯甲烷/水震荡,有机相经硫酸镁干燥,并过滤。将滤液浓缩,残留物由二氯甲烷/石油醚重结晶。
于0℃下,将2.31克(10毫摩尔)α-氨基-α-(3,4-二氟亚甲基二氧基-苯基)-乙酸和0.91克(24毫摩尔)硼氢化钠导入30毫升四氢呋喃中,之后滴加入于10毫升四氢呋喃中的3.05克(24毫摩尔)碘。当气体产生停止后,将混合物回流16小时。在混合物冷却后,将之用甲醇稀释,直到形成清澈溶液。将之浓缩,残留物用20毫升浓度为20%的2N氢氧化钠消化,用每次各50毫升二氯甲烷萃取三次。合并的有机相经硫酸镁干燥,并过滤。在滤液挥发后,以残留物获得的粗产物无需纯化,便可进一步反应。收率:1.52克(理论值的70%),熔点:70℃。实施例5b
将1.0克(2毫摩尔)N-[2-(2,6-二氟苯甲酰基氧基)-1-(3,4-二氟亚甲基二氧基-苯基)-乙基]-2,6-二氟苯甲酰胺导入2毫升甲醇中,在20℃下加入2毫升1N氢氧化钠溶液,并在搅拌下将混合物回流一小时。冷却后,将之与每次各50毫升二氯甲烷震荡三次。合并的有机相经硫酸镁干燥,并过滤。将滤液浓缩,以残留物获得的粗产物无需纯化,便可进一步反应。收率:0.67克(理论值的93%),熔点:158℃。
Claims (4)
2.防治人和动物上的寄生性昆虫和单食性蜱的组合物,其特征在于,它含有至少一种根据权利要求1的式(I)化合物。
3.制备防治人和动物上的寄生性昆虫和单食性蜱的组合物的方法,其特征在于,将根据权利要求1的式(I)化合物与填充剂和/或表面活性剂混合。
4.根据权利要求1的式(I)化合物用于制备防治人和动物上的寄生性昆虫和单食性蜱的组合物的应用。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19520936.2 | 1995-06-08 | ||
DE19520936A DE19520936A1 (de) | 1995-06-08 | 1995-06-08 | Ektoparasitizide Mittel |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1192651A true CN1192651A (zh) | 1998-09-09 |
Family
ID=7763930
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96196168A Pending CN1192651A (zh) | 1995-06-08 | 1996-05-28 | 杀体外寄生虫组合物 |
Country Status (16)
Country | Link |
---|---|
EP (1) | EP0831704A1 (zh) |
JP (1) | JP2000501695A (zh) |
KR (1) | KR19990022300A (zh) |
CN (1) | CN1192651A (zh) |
AR (1) | AR003433A1 (zh) |
AU (1) | AU5902096A (zh) |
BR (1) | BR9609252A (zh) |
CA (1) | CA2223147A1 (zh) |
CZ (1) | CZ395597A3 (zh) |
DE (1) | DE19520936A1 (zh) |
HU (1) | HUP9900369A2 (zh) |
PL (1) | PL323861A1 (zh) |
SK (1) | SK166297A3 (zh) |
TR (1) | TR199701531T1 (zh) |
WO (1) | WO1996041534A1 (zh) |
ZA (1) | ZA964831B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101252840B (zh) * | 2005-08-29 | 2012-02-08 | 诺瓦提斯公司 | 噁唑衍生物用于控制鱼寄生虫的用途 |
US8411618B2 (en) | 2008-09-05 | 2013-04-02 | Lg Electronics Inc. | Method of transmitting and receiving frame in a wireless communication system |
US9049636B2 (en) | 2008-09-23 | 2015-06-02 | Lg Electronics Inc. | Apparatus and method of transmitting and receiving data in soft handoff of a wireless communication system |
Families Citing this family (161)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19632126A1 (de) * | 1996-08-09 | 1998-02-12 | Bayer Ag | Phenylsubstituierte cyclische Ketoenole |
CO5031296A1 (es) | 1997-11-04 | 2001-04-27 | Novartis Ag | Derivados de azolina, compuestos que la contienen y metodo para la preparacion y aplicacion de dicho compuesto |
US6136838A (en) * | 1998-03-19 | 2000-10-24 | Merck & Co., Inc. | Sulfurpentafluorophenylpyrazoles for controlling ectoparasitic infestations |
US7687533B2 (en) | 2004-03-18 | 2010-03-30 | Pfizer Inc. | N-(1-arylpyrazol-4l) sulfonamides and their use as parasiticides |
JP4948830B2 (ja) * | 2005-12-05 | 2012-06-06 | 住化ライフテク株式会社 | 外部寄生虫駆除剤組成物および外部寄生虫駆除方法 |
US8110589B2 (en) | 2008-06-17 | 2012-02-07 | Kyoyu Agri Co., Ltd. | Ectoparasiticide composition and a method for exterminating extoparasites |
TWI487486B (zh) | 2009-12-01 | 2015-06-11 | Syngenta Participations Ag | 以異唑啉衍生物為主之殺蟲化合物 |
WO2011101402A1 (en) | 2010-02-17 | 2011-08-25 | Syngenta Participations Ag | Isoxazoline derivatives as insecticides |
JP2013520403A (ja) | 2010-02-22 | 2013-06-06 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 殺虫化合物としてのジヒドロフラン誘導体 |
JP2013520456A (ja) | 2010-02-25 | 2013-06-06 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | イソオキサゾリン誘導体の製造方法 |
EP2625165B1 (en) | 2010-10-05 | 2018-07-04 | Syngenta Participations AG | Insecticidal pyrrolidin-yl-aryl-carboxamides |
WO2012049327A2 (en) | 2010-10-15 | 2012-04-19 | Syngenta Participations Ag | Pesticidal mixtures |
EP2643302A1 (en) | 2010-11-23 | 2013-10-02 | Syngenta Participations AG | Insecticidal compounds |
EP2651921A1 (en) | 2010-12-17 | 2013-10-23 | Syngenta Participations AG | Insecticidal compounds |
CN103354811A (zh) | 2011-02-09 | 2013-10-16 | 先正达参股股份有限公司 | 杀虫化合物 |
US20140005235A1 (en) | 2011-03-22 | 2014-01-02 | Syngenta Participations Ag | Insecticidal compounds |
JP6030640B2 (ja) | 2011-05-18 | 2016-11-24 | シンジェンタ パーティシペーションズ アーゲー | アリールチオアセトアミド誘導体をベースとする殺虫化合物 |
US9339505B2 (en) | 2011-05-31 | 2016-05-17 | Syngenta Participations Ag | Pesticidal mixtures including isoxazoline derivatives |
AR086587A1 (es) | 2011-05-31 | 2014-01-08 | Syngenta Participations Ag | Compuestos insecticidas |
WO2012175474A1 (en) | 2011-06-20 | 2012-12-27 | Syngenta Participations Ag | 1,2,3 triazole pesticides |
CN103732567A (zh) | 2011-08-22 | 2014-04-16 | 先正达参股股份有限公司 | 作为杀虫化合物的二氢呋喃衍生物 |
US20140343049A1 (en) | 2011-08-22 | 2014-11-20 | Syngenta Participations Ag | Dihydrofuran derivatives as insecticidal compounds |
US9307766B2 (en) | 2011-08-25 | 2016-04-12 | Syngenta Participations Ag | Isoxazoline derivatives as insecticidal compounds |
WO2013026695A1 (en) | 2011-08-25 | 2013-02-28 | Syngenta Participations Ag | Isoxazoline derivatives as insecticidal compounds |
CN103764644A (zh) | 2011-08-25 | 2014-04-30 | 先正达参股股份有限公司 | 作为杀虫化合物的异噁唑啉衍生物 |
BR112014003730A2 (pt) | 2011-08-25 | 2017-03-14 | Syngenta Participations Ag | processo para a preparação de derivados de tietano |
WO2013026929A1 (en) | 2011-08-25 | 2013-02-28 | Syngenta Participations Ag | Dihydropyrrole derivatives as insecticidal compounds |
WO2013037626A1 (en) | 2011-09-13 | 2013-03-21 | Syngenta Participations Ag | Isothiazoline derivatives as insecticidal compounds |
JP2014534182A (ja) | 2011-10-03 | 2014-12-18 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 殺虫化合物としてのイソオキサゾリン誘導体 |
AU2012320779B8 (en) | 2011-10-03 | 2015-10-29 | Syngenta Participations Ag | Insecticidal 2-methoxybenzamide derivatives |
WO2013135674A1 (en) | 2012-03-12 | 2013-09-19 | Syngenta Participations Ag | Insecticidal 2-aryl-acetamide compounds |
WO2014001121A1 (en) | 2012-06-25 | 2014-01-03 | Syngenta Participations Ag | Isothiazole derivatives as insecticidal compounds |
WO2014001120A1 (en) | 2012-06-25 | 2014-01-03 | Syngenta Participations Ag | Isothiazole derivatives as insecticidal compounds |
BR112015009475A2 (pt) | 2012-10-31 | 2017-07-04 | Syngenta Participations Ag | compostos inseticidas |
WO2014079935A1 (en) | 2012-11-21 | 2014-05-30 | Syngenta Participations Ag | Insecticidal compounds based on arylthioacetamide derivatives |
US9402395B2 (en) | 2013-04-02 | 2016-08-02 | Syngenta Participations Ag | Insecticidal compounds |
BR112015025203B1 (pt) | 2013-04-02 | 2020-11-24 | Syngenta Participations Ag | compostos, processo para a produção de compostos, método de uso de compostos, métodos para controle de insetos, ácaros, nematódeos ou moluscos e para a proteção de plantas úteis e composição |
WO2015007451A1 (en) | 2013-07-15 | 2015-01-22 | Syngenta Participations Ag | Microbiocidal heterobicyclic derivatives |
EP3556744B1 (en) | 2013-12-23 | 2022-06-01 | Syngenta Participations AG | Insecticidal compounds |
TW201603707A (zh) * | 2014-06-24 | 2016-02-01 | 陶氏農業科學公司 | 具有特定殺蟲效用之分子及與其相關之中間物、組成物和製程 |
WO2016087593A1 (en) | 2014-12-05 | 2016-06-09 | Syngenta Participations Ag | Novel fungicidal quinolinylamidines |
GEP20197032B (en) | 2015-03-27 | 2019-10-25 | Participations Ag Syngenta | Microbiocidal heterobicyclic derivatives |
WO2016155831A1 (en) | 2015-04-02 | 2016-10-06 | Syngenta Participations Ag | Isoxazoline-styrene derivatives as insecticidal compounds |
HUE050030T2 (hu) | 2015-10-02 | 2020-11-30 | Syngenta Participations Ag | Mikrobiocid oxadiazol-származékok |
EP3367798A1 (en) | 2015-10-28 | 2018-09-05 | Syngenta Participations AG | Microbiocidal oxadiazole derivatives |
EP3371153A1 (en) | 2015-11-04 | 2018-09-12 | Syngenta Participations AG | Microbiocidal anilide derivatives |
UY36999A (es) | 2015-12-02 | 2017-06-30 | Syngenta Participations Ag | Derivados de aryl oxadiazol fungicidas |
EP3390399A1 (en) | 2015-12-17 | 2018-10-24 | Syngenta Participations AG | Microbiocidal oxadiazole derivatives |
JP2019514845A (ja) | 2016-03-15 | 2019-06-06 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物オキサジアゾール誘導体 |
EP3433252B1 (en) | 2016-03-24 | 2021-10-27 | Syngenta Participations AG | Microbicidal oxadiazole derivatives |
PL3439477T3 (pl) | 2016-04-08 | 2020-11-16 | Syngenta Participations Ag | Mikrobiocydowe pochodne oksadiazolowe |
CN109071522B (zh) | 2016-04-12 | 2022-04-12 | 先正达参股股份有限公司 | 杀微生物的噁二唑衍生物 |
WO2017178408A1 (en) | 2016-04-15 | 2017-10-19 | Syngenta Participations Ag | Microbiocidal silicon containing aryl derivatives |
CA3024528A1 (en) | 2016-05-30 | 2017-12-07 | Syngenta Participations Ag | Microbiocidal thiazole derivatives |
CN109195956A (zh) | 2016-06-03 | 2019-01-11 | 先正达参股股份有限公司 | 杀微生物的噁二唑衍生物 |
AR108745A1 (es) | 2016-06-21 | 2018-09-19 | Syngenta Participations Ag | Derivados de oxadiazol microbiocidas |
BR112019001229B1 (pt) | 2016-07-22 | 2022-11-16 | Syngenta Participations Ag | Composto derivado de oxadiazol, composição agroquímica compreendendo o mesmo, método para controlar ou impedir infestação de plantas úteis por microrganismos fitopatogênicos e uso do referido composto como fungicida |
BR112019000942B1 (pt) | 2016-07-22 | 2022-11-08 | Syngenta Participations Ag | Composto compreendendo derivados de oxadiazol e seu uso, composição agroquímica e método para controlar ou prevenir a infestação de plantas úteis por micro-organismos fitopatogênicos |
JP2019526535A (ja) | 2016-07-22 | 2019-09-19 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物オキサジアゾール誘導体 |
WO2018029242A1 (en) | 2016-08-11 | 2018-02-15 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
WO2018055133A1 (en) | 2016-09-23 | 2018-03-29 | Syngenta Participations Ag | Microbiocidal tetrazolone derivatives |
EP3515908A1 (en) | 2016-09-23 | 2019-07-31 | Syngenta Participations AG | Microbiocidal oxadiazole derivatives |
DK3522715T3 (da) | 2016-10-06 | 2021-04-12 | Syngenta Participations Ag | Mikrobiocide oxadiazolderivativer |
UY37623A (es) | 2017-03-03 | 2018-09-28 | Syngenta Participations Ag | Derivados de oxadiazol tiofeno fungicidas |
CN110392683A (zh) | 2017-03-10 | 2019-10-29 | 先正达参股股份有限公司 | 杀微生物的噁二唑衍生物 |
WO2018185013A1 (en) | 2017-04-03 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
BR112019021019B1 (pt) | 2017-04-05 | 2023-12-05 | Syngenta Participations Ag | Compostos derivados de oxadiazol microbiocidas, composição agrícola, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos e uso de um composto derivado de oxadiazol |
WO2018184984A1 (en) | 2017-04-05 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
WO2018184985A1 (en) | 2017-04-05 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
BR112019020819B1 (pt) | 2017-04-05 | 2023-12-05 | Syngenta Participations Ag | Composto de fórmula (i), composição agroquímica, método para controlar ou prevenir a infestação de plantas úteis por micro-organismos fitopatogênicos e uso de um composto de fórmula (i) |
WO2018184986A1 (en) | 2017-04-05 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
WO2018184982A1 (en) | 2017-04-05 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
WO2018185211A1 (en) | 2017-04-06 | 2018-10-11 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
WO2018206419A1 (en) | 2017-05-12 | 2018-11-15 | Syngenta Participations Ag | Microbiocidal heterobicyclic derivatives |
US11447481B2 (en) | 2017-06-02 | 2022-09-20 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
WO2019011929A1 (en) | 2017-07-11 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
WO2019011926A1 (en) | 2017-07-11 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
BR112020000465B1 (pt) | 2017-07-11 | 2024-02-20 | Syngenta Participations Ag | Derivados oxadiazol microbiocidas |
WO2019011928A1 (en) | 2017-07-11 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
BR112020000414A2 (pt) | 2017-07-12 | 2020-07-21 | Syngenta Participations Ag | derivados de oxadiazol microbicidas |
BR112020000371A2 (pt) | 2017-07-12 | 2020-07-14 | Syngenta Participations Ag | derivados de oxadiazol microbiocidas |
BR112020000463A2 (pt) | 2017-07-13 | 2020-07-21 | Syngenta Participations Ag | derivados oxadiazol microbiocidas |
CN111051286A (zh) | 2017-09-13 | 2020-04-21 | 先正达参股股份有限公司 | 杀微生物的喹啉(硫代)甲酰胺衍生物 |
ES2896598T3 (es) | 2017-09-13 | 2022-02-24 | Syngenta Participations Ag | Derivados de quinolina (tio)carboxamida microbiocidas |
ES2894762T3 (es) | 2017-09-13 | 2022-02-15 | Syngenta Participations Ag | Derivados de quinolina (tio)carboxamida microbiocidas |
JP7150009B2 (ja) | 2017-09-13 | 2022-10-07 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物性キノリン(チオ)カルボキサミド誘導体 |
US20200267978A1 (en) | 2017-09-13 | 2020-08-27 | Syngenta Participations Ag | Microbiocidal quinoline (thio)carboxamide derivatives |
JP7330949B2 (ja) | 2017-09-13 | 2023-08-22 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物性キノリン(チオ)カルボキサミド誘導体 |
BR112020004692A2 (pt) | 2017-09-13 | 2020-09-15 | Syngenta Participations Ag | derivados microbiocidas de (tio)carboxamida de quinolina |
UY37913A (es) | 2017-10-05 | 2019-05-31 | Syngenta Participations Ag | Derivados de picolinamida fungicidas que portan un grupo terminal cuaternario |
UY37912A (es) | 2017-10-05 | 2019-05-31 | Syngenta Participations Ag | Derivados de picolinamida fungicidas que portan grupos terminales heteroarilo o heteroariloxi |
BR112020009659A2 (pt) | 2017-11-15 | 2020-11-10 | Syngenta Participations Ag | derivados picolinamida microbiocidas |
WO2019097054A1 (en) | 2017-11-20 | 2019-05-23 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
GEP20227389B (en) | 2017-11-29 | 2022-06-10 | Syngenta Participations Ag | Microbiocidal thiazole derivatives |
GB201721235D0 (en) | 2017-12-19 | 2018-01-31 | Syngenta Participations Ag | Polymorphs |
WO2019121149A1 (en) | 2017-12-19 | 2019-06-27 | Syngenta Participations Ag | Microbiocidal picolinamide derivatives |
BR112020021645A2 (pt) | 2018-04-26 | 2021-01-26 | Syngenta Participations Ag | derivados de oxadiazol microbicidas |
CN112154141A (zh) | 2018-05-25 | 2020-12-29 | 先正达参股股份有限公司 | 杀微生物的吡啶甲酰胺衍生物 |
WO2020002331A1 (en) | 2018-06-29 | 2020-01-02 | Syngenta Crop Protection Ag | Microbiocidal oxadiazole derivatives |
BR112020027003A2 (pt) | 2018-07-02 | 2021-04-06 | Syngenta Crop Protection Ag | Derivados de 3-(2-tienil)-5-(trifluorometil)-1,2,4-oxadiazol como fungicidas agroquímicos |
CN112689631A (zh) | 2018-07-16 | 2021-04-20 | 先正达农作物保护股份公司 | 杀微生物的噁二唑衍生物 |
GB201812692D0 (en) | 2018-08-03 | 2018-09-19 | Syngenta Participations Ag | Microbiocidal compounds |
CN112739685A (zh) | 2018-09-19 | 2021-04-30 | 先正达农作物保护股份公司 | 杀微生物的喹啉甲酰胺衍生物 |
WO2020070132A1 (en) | 2018-10-06 | 2020-04-09 | Syngenta Participations Ag | Microbiocidal quinoline dihydro-(thiazine)oxazine derivatives |
JP2022504304A (ja) | 2018-10-06 | 2022-01-13 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物性キノリンジヒドロ-(チアジン)オキサジン誘導体 |
CN113195462A (zh) | 2018-10-17 | 2021-07-30 | 先正达农作物保护股份公司 | 杀微生物的噁二唑衍生物 |
AR116628A1 (es) | 2018-10-18 | 2021-05-26 | Syngenta Crop Protection Ag | Compuestos microbiocidas |
AR117183A1 (es) | 2018-11-30 | 2021-07-14 | Syngenta Crop Protection Ag | Derivados de tiazol microbiocidas |
AR117200A1 (es) | 2018-11-30 | 2021-07-21 | Syngenta Participations Ag | Derivados de tiazol microbiocidas |
WO2020165403A1 (en) | 2019-02-15 | 2020-08-20 | Syngenta Crop Protection Ag | Phenyl substituted thiazole derivatives as microbiocidal compounds |
GB201903942D0 (en) | 2019-03-22 | 2019-05-08 | Syngenta Crop Protection Ag | Microbiocidal compounds |
EP3947371B1 (en) | 2019-03-27 | 2023-11-22 | Syngenta Crop Protection AG | Microbiocidal thiazole derivatives |
WO2020208095A1 (en) | 2019-04-10 | 2020-10-15 | Syngenta Crop Protection Ag | Microbiocidal picolinamide derivatives |
WO2020239855A1 (en) | 2019-05-29 | 2020-12-03 | Syngenta Crop Protection Ag | Microbiocidal derivatives |
WO2020239853A1 (en) | 2019-05-29 | 2020-12-03 | Syngenta Crop Protection Ag | Microbiocidal derivatives |
AR119009A1 (es) | 2019-05-29 | 2021-11-17 | Syngenta Crop Protection Ag | Derivados de alcoxipiridina y alcoxipirimidina microbicidas |
AR119011A1 (es) | 2019-05-29 | 2021-11-17 | Syngenta Crop Protection Ag | DERIVADOS DE [1,3]DIOXOLO[4,5-c]PIRIDIN-4-CARBOXAMIDA, COMPOSICIONES AGROQUÍMICAS QUE LOS COMPRENDEN Y SU EMPLEO COMO FUNGICIDA PARA CONTROLAR O PREVENIR LA INFESTACIÓN DE PLANTAS ÚTILES |
BR112021026861A2 (pt) | 2019-07-05 | 2022-02-22 | Syngenta Crop Protection Ag | Derivados de picolinamida microbiocidas |
GB201910037D0 (en) | 2019-07-12 | 2019-08-28 | Syngenta Crop Protection Ag | Microbiocidal compounds |
AU2020333829A1 (en) | 2019-08-21 | 2022-03-03 | Syngenta Participations Ag | Precision treatment and sowing or planting method and device |
US20220272892A1 (en) | 2019-08-21 | 2022-09-01 | Syngenta Participations Ag | High precision greenhouse seed and seedling treatment |
BR112022003060A2 (pt) | 2019-08-21 | 2022-05-10 | Syngenta Participations Ag | Aparelho e método para conversão de equipamentos de semeadura existentes |
US20220279703A1 (en) | 2019-08-21 | 2022-09-08 | Syngenta Participations Ag | Apparatus and method for reducing dust development in precision drill sowing |
US20220279702A1 (en) | 2019-08-21 | 2022-09-08 | Syngenta Participations Ag | Sowing device and method for treating seeds during planting |
WO2021204822A1 (en) | 2020-04-08 | 2021-10-14 | Syngenta Crop Protection Ag | Microbiocidal quinoline dihydro-(thiazine)oxazine derivatives |
AR121734A1 (es) | 2020-04-08 | 2022-07-06 | Syngenta Crop Protection Ag | Derivados microbicidas de tipo dihidropirrolopirazina de quinolina |
AR121733A1 (es) | 2020-04-08 | 2022-07-06 | Syngenta Crop Protection Ag | Derivados microbiocidas de tipo dihidro-(tiazina)oxazina de quinolina |
GB202006399D0 (en) | 2020-04-30 | 2020-06-17 | Syngenta Crop Protection Ag | Microbiocidal compounds |
GB202006386D0 (en) | 2020-04-30 | 2020-06-17 | Syngenta Crop Protection Ag | Microbiocidal Compounds |
GB202006480D0 (en) | 2020-05-01 | 2020-06-17 | Syngenta Crop Protection Ag | Microbiocidal compounds |
GB202006606D0 (en) | 2020-05-05 | 2020-06-17 | Syngenta Crop Protection Ag | Microbiocidal compounds |
CA3178975A1 (en) | 2020-06-03 | 2021-12-09 | Syngenta Crop Protection Ag | Microbiocidal derivatives |
GB202014840D0 (en) | 2020-09-21 | 2020-11-04 | Syngenta Crop Protection Ag | Microbiocidal compounds |
WO2022207479A1 (en) | 2021-03-27 | 2022-10-06 | Syngenta Crop Protection Ag | Microbiocidal isonicotinic amide derivatives |
UY39696A (es) | 2021-03-31 | 2022-10-31 | Syngenta Crop Protection Ag | Derivados microbiocidas de quinolin/quinoxalin-benzotiazina como agentes fungicidas, en particular c |
BR112023021626A2 (pt) | 2021-04-20 | 2024-02-20 | Syngenta Crop Protection Ag | Derivados microbiocidas de quinolina/quinoxalina isoquinolina |
AU2022323303A1 (en) | 2021-08-02 | 2024-02-01 | Syngenta Crop Protection Ag | Microbiocidal pyrazole derivatives |
WO2023089049A2 (en) | 2021-11-19 | 2023-05-25 | Syngenta Crop Protection Ag | Microbiocidal isonicotinic amide derivatives |
WO2023094303A1 (en) | 2021-11-25 | 2023-06-01 | Syngenta Crop Protection Ag | Microbiocidal heterobiaryl amide derivatives |
WO2023094304A1 (en) | 2021-11-25 | 2023-06-01 | Syngenta Crop Protection Ag | Microbiocidal heterobiaryl amide derivatives |
AR127922A1 (es) | 2021-12-15 | 2024-03-13 | Syngenta Crop Protection Ag | Derivados heterocíclicos bicíclicos microbiocidas |
WO2023111215A1 (en) | 2021-12-17 | 2023-06-22 | Syngenta Crop Protection Ag | Microbiocidal pyridine-substituted benzothiazine derivatives |
WO2023110871A1 (en) | 2021-12-17 | 2023-06-22 | Syngenta Crop Protection Ag | Microbiocidal pyrazole derivatives |
WO2023118011A1 (en) | 2021-12-22 | 2023-06-29 | Syngenta Crop Protection Ag | Microbiocidal aza-heterobiaryl derivatives |
WO2023139166A1 (en) | 2022-01-19 | 2023-07-27 | Syngenta Crop Protection Ag | Methods for controlling plant pathogens |
WO2023148206A1 (en) | 2022-02-02 | 2023-08-10 | Syngenta Crop Protection Ag | Microbiocidal n-amide derivatives |
WO2023166067A1 (en) | 2022-03-02 | 2023-09-07 | Syngenta Crop Protection Ag | Microbiocidal pyridazinone amide derivatives |
TW202408362A (zh) | 2022-06-21 | 2024-03-01 | 瑞士商先正達農作物保護公司 | 殺微生物的雙環雜環甲醯胺衍生物 |
WO2024018016A1 (en) | 2022-07-21 | 2024-01-25 | Syngenta Crop Protection Ag | Crystalline forms of 1,2,4-oxadiazole fungicides |
WO2024068656A1 (en) | 2022-09-28 | 2024-04-04 | Syngenta Crop Protection Ag | Fungicidal compositions |
WO2024068655A1 (en) | 2022-09-28 | 2024-04-04 | Syngenta Crop Protection Ag | Fungicidal compositions |
WO2024068947A1 (en) | 2022-09-30 | 2024-04-04 | Syngenta Crop Protection Ag | Microbiocidal pyrazole derivatives |
WO2024068950A1 (en) | 2022-09-30 | 2024-04-04 | Syngenta Crop Protection Ag | Microbiocidal pyrazole derivatives |
WO2024089191A1 (en) | 2022-10-27 | 2024-05-02 | Syngenta Crop Protection Ag | Microbiocidal heterobicyclic dihydrooxadiazine derivatives |
WO2024100069A1 (en) | 2022-11-08 | 2024-05-16 | Syngenta Crop Protection Ag | Microbiocidal pyridine derivatives |
WO2024100115A1 (en) | 2022-11-09 | 2024-05-16 | Syngenta Crop Protection Ag | Microbiocidal pyrazole derivatives |
WO2024105104A1 (en) | 2022-11-16 | 2024-05-23 | Syngenta Crop Protection Ag | Microbiocidal tetrahydroisoquinoline derivatives |
WO2024115509A1 (en) | 2022-11-29 | 2024-06-06 | Syngenta Crop Protection Ag | Microbiocidal tetrahydroisoquinoline derivatives |
WO2024115512A1 (en) | 2022-11-30 | 2024-06-06 | Syngenta Crop Protection Ag | Microbiocidal tetrahydroisoquinoline derivatives |
WO2024132895A1 (en) | 2022-12-19 | 2024-06-27 | Syngenta Crop Protection Ag | Microbiocidal dihydrooxadiazinyl pyridazinone compounds |
WO2024132901A1 (en) | 2022-12-19 | 2024-06-27 | Syngenta Crop Protection Ag | Microbiocidal pyridazine dihydrooxadiazine derivatives |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1963192A1 (de) * | 1969-12-17 | 1971-06-24 | Bayer Ag | Ektoparasiticide Mittel |
JP3163545B2 (ja) * | 1991-06-24 | 2001-05-08 | 八洲化学工業株式会社 | 4−チエニル−オキサ(チア)ゾリン誘導体、及びこれを含有する殺虫・殺ダニ剤 |
AU658955B2 (en) * | 1992-01-28 | 1995-05-04 | Sumitomo Chemical Company, Limited | An oxazoline derivative, its production and its use |
EP0637302A1 (en) * | 1992-04-22 | 1995-02-08 | E.I. Du Pont De Nemours And Company | Arthropodicidal oxa- and thia-zolines |
BR9306542A (pt) * | 1992-05-26 | 1998-09-15 | Du Pont | Composto composição artropodicida e método de controle de artrópodes |
JP3209576B2 (ja) * | 1992-06-12 | 2001-09-17 | 八洲化学工業株式会社 | ダニ防除剤 |
JPH06100546A (ja) * | 1992-09-24 | 1994-04-12 | Ube Ind Ltd | 4−ナフチル置換オキサゾリン誘導体、その製法及び殺虫殺ダニ剤 |
ES2105940B1 (es) * | 1993-09-22 | 1998-07-01 | Sumitomo Chemical Co | Una composicion insecticida y acaricida, un metodo para reprimir insectos y acaros y empleo de dicha composicion. |
DE4401098A1 (de) * | 1994-01-17 | 1995-07-20 | Bayer Ag | Diphenyloxazolin-Derivate |
DE4401099A1 (de) * | 1994-01-17 | 1995-07-20 | Bayer Ag | Substituierte Oxazoline |
DE4401101A1 (de) * | 1994-01-17 | 1995-07-20 | Bayer Ag | Phenylthio-oxazolin-Derivate |
TW440429B (en) * | 1994-08-12 | 2001-06-16 | Bayer Ag | Substituted biphenyloxazolines |
-
1995
- 1995-06-08 DE DE19520936A patent/DE19520936A1/de not_active Withdrawn
-
1996
- 1996-05-28 TR TR97/01531T patent/TR199701531T1/xx unknown
- 1996-05-28 AU AU59020/96A patent/AU5902096A/en not_active Abandoned
- 1996-05-28 CN CN96196168A patent/CN1192651A/zh active Pending
- 1996-05-28 WO PCT/EP1996/002284 patent/WO1996041534A1/de not_active Application Discontinuation
- 1996-05-28 SK SK1662-97A patent/SK166297A3/sk unknown
- 1996-05-28 CA CA002223147A patent/CA2223147A1/en not_active Abandoned
- 1996-05-28 EP EP96916163A patent/EP0831704A1/de not_active Withdrawn
- 1996-05-28 HU HU9900369A patent/HUP9900369A2/hu unknown
- 1996-05-28 BR BR9609252A patent/BR9609252A/pt unknown
- 1996-05-28 PL PL96323861A patent/PL323861A1/xx unknown
- 1996-05-28 CZ CZ973955A patent/CZ395597A3/cs unknown
- 1996-05-28 JP JP9502549A patent/JP2000501695A/ja not_active Ceased
- 1996-05-28 KR KR1019970708779A patent/KR19990022300A/ko not_active Application Discontinuation
- 1996-06-07 ZA ZA964831A patent/ZA964831B/xx unknown
- 1996-07-06 AR ARP960103089A patent/AR003433A1/es unknown
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101252840B (zh) * | 2005-08-29 | 2012-02-08 | 诺瓦提斯公司 | 噁唑衍生物用于控制鱼寄生虫的用途 |
US8411618B2 (en) | 2008-09-05 | 2013-04-02 | Lg Electronics Inc. | Method of transmitting and receiving frame in a wireless communication system |
US9049636B2 (en) | 2008-09-23 | 2015-06-02 | Lg Electronics Inc. | Apparatus and method of transmitting and receiving data in soft handoff of a wireless communication system |
US9648532B2 (en) | 2008-09-23 | 2017-05-09 | Lg Electronics Inc. | Apparatus and method of transmitting and receiving data in soft handoff of a wireless communication system |
Also Published As
Publication number | Publication date |
---|---|
AR003433A1 (es) | 1998-08-05 |
CA2223147A1 (en) | 1996-12-27 |
KR19990022300A (ko) | 1999-03-25 |
PL323861A1 (en) | 1998-04-27 |
AU5902096A (en) | 1997-01-09 |
JP2000501695A (ja) | 2000-02-15 |
BR9609252A (pt) | 1999-05-11 |
MX9709648A (es) | 1998-07-31 |
SK166297A3 (en) | 1998-08-05 |
WO1996041534A1 (de) | 1996-12-27 |
EP0831704A1 (de) | 1998-04-01 |
CZ395597A3 (cs) | 1998-05-13 |
ZA964831B (en) | 1997-01-07 |
TR199701531T1 (xx) | 1998-05-21 |
HUP9900369A2 (hu) | 1999-05-28 |
DE19520936A1 (de) | 1996-12-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1192651A (zh) | 杀体外寄生虫组合物 | |
CN1059672C (zh) | 1,2,4-二唑衍生物 | |
CN85109721A (zh) | 制备具有控制无疾病温血动物的外寄生物与内寄生物组合物之方法 | |
CN1930134A (zh) | 嘧啶化合物在制备杀寄生物药中的用途 | |
CN1053233A (zh) | 作为杀虫剂的n-苯基吡唑衍生物 | |
CN1031265C (zh) | 含四氢化嘧啶的控制害虫组合物 | |
CN1274672C (zh) | 氨基乙腈衍生物及其在控制寄生虫中的用途 | |
CN1309715C (zh) | N-酰氨基乙腈衍生物及其用于制备控制寄生虫的药物中的用途 | |
CN1318536A (zh) | 取代联苯基噁唑啉 | |
CN1306394A (zh) | 杀外寄生虫组合物 | |
CN100347153C (zh) | 酰氨基乙腈化合物及其作为杀虫剂的用途 | |
CN1656061A (zh) | 有机化合物 | |
CN1166832A (zh) | 取代的联苯基噁唑啉类化合物 | |
CN1670016A (zh) | 具杀虫、杀螨、杀真菌生物活性的芳基吡咯类化合物及其制备方法 | |
CN1207092A (zh) | 联苯醚-噁唑啉类化合物及其作为害虫防治剂的应用 | |
CN1602296A (zh) | 氨基乙腈衍生物 | |
CN1113238A (zh) | 取代的吡唑啉衍生物 | |
CN1057523C (zh) | 二苯基噁唑啉衍生物、制法、应用和组合物 | |
CN1059671C (zh) | 3-芳基-链烯基-1,2,4-二唑衍生物 | |
CN1688193A (zh) | 用于防治寄生虫的混合组合物 | |
CN1071322C (zh) | 5,6-二氢-1,3-噁嗪类化合物的制备方法 | |
CN1113603C (zh) | 吖嗪衍生物 | |
CN1048725C (zh) | 烟酸衍生物及除草剂 | |
CN1131417A (zh) | 取代的4-氨基甲酰基-吡咯啉-2-酮衍生物和4-氨基甲酰基-二氢呋喃-2-酮衍生物及其作为农药的用途 | |
CN1143957A (zh) | 杀节肢动物的2-噁唑啉和2-噻唑啉 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C53 | Correction of patent of invention or patent application | ||
COR | Change of bibliographic data |
Free format text: CORRECT: APPLICANT; FROM: BAYER AG TO: YASHIMA CHEMICAL INDUSTRY CO., LTD. |
|
CP03 | Change of name, title or address |
Address after: Kanagawa Applicant after: Yashima Chemical Industry Co., Ltd. Address before: Eight Germany Leverkusen delta Chemical Industry Co Ltd Applicant before: Bayer Aktiengesellschaft |
|
C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
WD01 | Invention patent application deemed withdrawn after publication |