ES2255766T3 - Plaguicidas. - Google Patents
Plaguicidas.Info
- Publication number
- ES2255766T3 ES2255766T3 ES99958038T ES99958038T ES2255766T3 ES 2255766 T3 ES2255766 T3 ES 2255766T3 ES 99958038 T ES99958038 T ES 99958038T ES 99958038 T ES99958038 T ES 99958038T ES 2255766 T3 ES2255766 T3 ES 2255766T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- compound
- alkyl
- methyl
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000575 pesticide Substances 0.000 title description 78
- 150000001875 compounds Chemical class 0.000 claims abstract description 147
- -1 nitro, hydroxy Chemical group 0.000 claims abstract description 70
- 125000001424 substituent group Chemical group 0.000 claims abstract description 37
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 26
- 150000002367 halogens Chemical class 0.000 claims abstract description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 7
- 239000000203 mixture Substances 0.000 claims description 62
- 241001465754 Metazoa Species 0.000 claims description 61
- 238000002360 preparation method Methods 0.000 claims description 38
- 239000004480 active ingredient Substances 0.000 claims description 34
- 230000009471 action Effects 0.000 claims description 29
- 238000009472 formulation Methods 0.000 claims description 28
- 239000000460 chlorine Substances 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 244000045947 parasite Species 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 239000011630 iodine Substances 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 230000000590 parasiticidal effect Effects 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- 239000002270 dispersing agent Substances 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims 2
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims 1
- ZRYCZAWRXHAAPZ-UHFFFAOYSA-N alpha,alpha-dimethyl valeric acid Chemical compound CCCC(C)(C)C(O)=O ZRYCZAWRXHAAPZ-UHFFFAOYSA-N 0.000 claims 1
- 231100000614 poison Toxicity 0.000 claims 1
- 230000007096 poisonous effect Effects 0.000 claims 1
- 239000000273 veterinary drug Substances 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 241000258242 Siphonaptera Species 0.000 description 38
- 239000000243 solution Substances 0.000 description 38
- 239000000126 substance Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 241000282472 Canis lupus familiaris Species 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 241000238631 Hexapoda Species 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 241000282326 Felis catus Species 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 230000007774 longterm Effects 0.000 description 12
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000008280 blood Substances 0.000 description 9
- 210000004369 blood Anatomy 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
- 229920002472 Starch Polymers 0.000 description 8
- FYZBOYWSHKHDMT-UHFFFAOYSA-N benfuracarb Chemical compound CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 FYZBOYWSHKHDMT-UHFFFAOYSA-N 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 8
- 239000007943 implant Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 230000000699 topical effect Effects 0.000 description 7
- 241000258924 Ctenocephalides felis Species 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 239000000470 constituent Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 description 5
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 5
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 5
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 5
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 5
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 5
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 5
- 239000002798 polar solvent Substances 0.000 description 5
- 239000005871 repellent Substances 0.000 description 5
- 230000002940 repellent Effects 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 5
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 description 4
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 4
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000490513 Ctenocephalides canis Species 0.000 description 4
- 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 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- GBAWQJNHVWMTLU-RQJHMYQMSA-N [(1R,5S)-7-chloro-6-bicyclo[3.2.0]hepta-2,6-dienyl] dimethyl phosphate Chemical compound C1=CC[C@@H]2C(OP(=O)(OC)OC)=C(Cl)[C@@H]21 GBAWQJNHVWMTLU-RQJHMYQMSA-N 0.000 description 4
- 230000000895 acaricidal effect Effects 0.000 description 4
- 239000000642 acaricide Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- CJJOSEISRRTUQB-UHFFFAOYSA-N azinphos-methyl Chemical group C1=CC=C2C(=O)N(CSP(=S)(OC)OC)N=NC2=C1 CJJOSEISRRTUQB-UHFFFAOYSA-N 0.000 description 4
- KXRPCFINVWWFHQ-UHFFFAOYSA-N cadusafos Chemical compound CCC(C)SP(=O)(OCC)SC(C)CC KXRPCFINVWWFHQ-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000002274 desiccant Substances 0.000 description 4
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 description 4
- DMYHGDXADUDKCQ-UHFFFAOYSA-N fenazaquin Chemical compound C1=CC(C(C)(C)C)=CC=C1CCOC1=NC=NC2=CC=CC=C12 DMYHGDXADUDKCQ-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
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- 229960000323 triclabendazole Drugs 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Tropical Medicine & Parasitology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2298/98 | 1998-11-17 | ||
| CH229898 | 1998-11-17 | ||
| CH797/99 | 1999-04-29 | ||
| CH79799 | 1999-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2255766T3 true ES2255766T3 (es) | 2006-07-01 |
Family
ID=25685711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99958038T Expired - Lifetime ES2255766T3 (es) | 1998-11-17 | 1999-11-15 | Plaguicidas. |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US6538013B2 (enExample) |
| EP (1) | EP1131292B1 (enExample) |
| JP (1) | JP2002529532A (enExample) |
| KR (1) | KR100620470B1 (enExample) |
| CN (1) | CN1177823C (enExample) |
| AR (1) | AR023703A1 (enExample) |
| AT (1) | ATE317385T1 (enExample) |
| AU (1) | AU762529B2 (enExample) |
| BR (1) | BR9915430A (enExample) |
| CA (1) | CA2350742A1 (enExample) |
| CO (1) | CO5210925A1 (enExample) |
| CY (1) | CY1106083T1 (enExample) |
| DE (1) | DE69929820T2 (enExample) |
| DK (1) | DK1131292T3 (enExample) |
| ES (1) | ES2255766T3 (enExample) |
| HK (1) | HK1038563B (enExample) |
| IL (2) | IL142687A0 (enExample) |
| NZ (1) | NZ511380A (enExample) |
| PT (1) | PT1131292E (enExample) |
| RU (1) | RU2245877C2 (enExample) |
| TW (1) | TW561149B (enExample) |
| WO (1) | WO2000029378A2 (enExample) |
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|---|---|---|---|---|
| US6406705B1 (en) | 1997-03-10 | 2002-06-18 | University Of Iowa Research Foundation | Use of nucleic acids containing unmethylated CpG dinucleotide as an adjuvant |
| US6933318B1 (en) | 1999-08-12 | 2005-08-23 | Eli Lilly And Company | Topical organic ectoparasiticidal formulations |
| EP1207851A1 (en) * | 1999-08-12 | 2002-05-29 | Eli Lilly And Company | Topical organic ectoparasiticidal formulations |
| US6376548B1 (en) | 2000-01-28 | 2002-04-23 | Rohm And Haas Company | Enhanced propertied pesticides |
| US7186855B2 (en) * | 2001-06-11 | 2007-03-06 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US7232924B2 (en) | 2001-06-11 | 2007-06-19 | Xenoport, Inc. | Methods for synthesis of acyloxyalkyl derivatives of GABA analogs |
| PT1404324E (pt) * | 2001-06-11 | 2008-03-05 | Xenoport Inc | Formas de dosagem administradas oralmente de pró-fármacos análogas de gaba tendo toxicidade reduzida |
| US6818787B2 (en) | 2001-06-11 | 2004-11-16 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US8048917B2 (en) | 2005-04-06 | 2011-11-01 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| JP2003026603A (ja) * | 2001-07-17 | 2003-01-29 | Sumika Life Tech Co Ltd | コンパニオンアニマルの外部寄生虫駆除用水性滴下剤 |
| US7011837B2 (en) * | 2001-08-29 | 2006-03-14 | Rutgers, The State University Of New Jersey | Isolated species of steinernematid nematode and methods of white grub control therewith |
| EP2347654B1 (en) | 2001-09-17 | 2019-02-27 | Elanco US Inc. | Formulation for controlling lice or ticks in catlle |
| CN101597262A (zh) * | 2002-03-05 | 2009-12-09 | 特兰斯泰克制药公司 | 抑制配体与高级糖化终产物受体相互作用的单和双环吡咯衍生物 |
| MXPA05012350A (es) * | 2003-05-20 | 2006-05-25 | Transtech Pharma Inc | Antagonistas rage como agentes para la amiloidosis inversa y enfermedades asociadas con la misma. |
| US7396819B2 (en) * | 2003-08-08 | 2008-07-08 | Virbac Corporation | Anthelmintic formulations |
| US7531186B2 (en) * | 2003-12-17 | 2009-05-12 | Merial Limited | Topical formulations comprising 1-N-arylpyrazole derivatives and amitraz |
| WO2005094210A2 (en) * | 2004-03-12 | 2005-10-13 | The Hartz Mountain Corporation | Multi-action anthelmintic formulations |
| GT200500317A (es) * | 2004-11-05 | 2006-10-27 | Proceso para preparar compuestos de quinolina y productos obtenidos de los mismos | |
| AR054849A1 (es) * | 2005-07-26 | 2007-07-18 | Wyeth Corp | Diazepinoquinolinas, sintesis de las mismas, e intermediarios para obtenerlas |
| JP5053289B2 (ja) * | 2005-12-22 | 2012-10-17 | エフ エム シー コーポレーション | ビフェントリンおよび強力シペルメトリンの新規な処方物 |
| TW200734334A (en) * | 2006-01-13 | 2007-09-16 | Wyeth Corp | Treatment of substance abuse |
| KR20080110759A (ko) * | 2006-03-24 | 2008-12-19 | 와이어쓰 | 통증 치료 |
| PE20080125A1 (es) * | 2006-03-24 | 2008-04-07 | Wyeth Corp | Metodo para modular la funcion de la vejiga |
| TW200806300A (en) * | 2006-03-24 | 2008-02-01 | Wyeth Corp | New therapeutic combinations for the treatment of depression |
| US20070225278A1 (en) * | 2006-03-24 | 2007-09-27 | Wyeth | Methods for treating cognitive and other disorders |
| RU2340181C1 (ru) * | 2007-03-06 | 2008-12-10 | Александр Анатольевич Хахалин | Инсектоакарицидное средство "инсектал-плюс" |
| CL2008002777A1 (es) * | 2007-09-21 | 2010-01-22 | Wyeth Corp | Metodo de preparacion de compuestos diazepinoquinolinicos quirales por recristalizacion en un sistema de solvente ternario. |
| FR2922108A1 (fr) | 2007-10-11 | 2009-04-17 | Virbac Sa | Utilisation d'un derive de 1-n-(halo-3-pyridylmethyle)-n-methylamino-1-alkylamino -2- nitroethylene pour la preparation d'une composition pharmaceutique veterinaire pour lutter contre les puces |
| CN101854928A (zh) * | 2007-11-08 | 2010-10-06 | 希普洛有限公司 | 包含燕麦蒽酰胺的组合物 |
| US9173728B2 (en) | 2008-11-19 | 2015-11-03 | Merial Inc. | Multi-cavity container having offset indentures for dispensing fluids |
| CN102271672B (zh) | 2008-11-19 | 2015-02-04 | 梅里亚有限公司 | 用于治疗寄生物感染的包含单独的或与甲脒组合的1-芳基吡唑的组合物 |
| EP2470510B1 (en) | 2009-09-30 | 2014-05-14 | TransTech Pharma, LLC | Substituted imidazole derivatives for treatment of alzheimers disease. |
| UA115967C2 (uk) | 2011-01-04 | 2018-01-25 | Зе Клаймат Корпорейшн | Способи генерування карт ґрунтів і приписів щодо посіву насіння |
| WO2012138320A1 (en) * | 2011-04-04 | 2012-10-11 | Carro, A | Ingestible insect repellent composition and system |
| NZ722096A (en) | 2011-12-15 | 2016-11-25 | Alkermes Pharma Ireland Ltd | Prodrugs of secondary amine compounds |
| US10743535B2 (en) | 2017-08-18 | 2020-08-18 | H&K Solutions Llc | Insecticide for flight-capable pests |
| CN111978243B (zh) * | 2019-05-24 | 2022-09-06 | 南开大学 | 草酸单酯类衍生物的合成及其应用 |
| CN111978244B (zh) * | 2019-05-24 | 2022-09-06 | 南开大学 | 一类烯啶虫胺酰基衍生物的合成及其应用 |
| US11895941B2 (en) | 2019-09-23 | 2024-02-13 | Cnh Industrial America Llc | Tillage system with variable fertilizer application |
| TWI893037B (zh) * | 2019-12-23 | 2025-08-11 | 美商欣爍克斯公司 | 製備n6-((2-疊氮基乙氧基)羰基)離胺酸的方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZW5085A1 (en) | 1984-04-13 | 1985-09-18 | Nihon Tokushu Noyaku Seizo Kk | Nitromethylene derivatives,intermediates thereof,processes for production thereof,and insecticides |
| ATE67493T1 (de) * | 1985-02-04 | 1991-10-15 | Bayer Agrochem Kk | Heterocyclische verbindungen. |
| JPH07121909B2 (ja) | 1986-09-10 | 1995-12-25 | 日本バイエルアグロケム株式会社 | 新規複素環式化合物及び殺虫剤 |
| DE3712307A1 (de) | 1987-04-10 | 1988-10-20 | Bayer Ag | 3-substituierte 1-(2-chlor-thiazol-5-yl-methyl)-2- nitroimino-1,3-diazacycloalkane |
| ATE166051T1 (de) | 1987-08-01 | 1998-05-15 | Takeda Chemical Industries Ltd | Zwischenprodukte, ihre herstellung und verwendung zur herstellung alpha-ungesättigter amine |
| DE3887800D1 (de) | 1987-08-04 | 1994-03-24 | Ciba Geigy | Substituierte Guanidine. |
| US4918086A (en) | 1987-08-07 | 1990-04-17 | Ciba-Geigy Corporation | 1-nitro-2,2-diaminoethylene derivatives |
| JP2884412B2 (ja) | 1988-10-21 | 1999-04-19 | 日本バイエルアグロケム株式会社 | 殺虫性シアノ化合物 |
| JP2779403B2 (ja) | 1988-11-29 | 1998-07-23 | 日本バイエルアグロケム株式会社 | 殺虫性ニトロ化合物 |
| IE71183B1 (en) | 1988-12-27 | 1997-01-29 | Takeda Chemical Industries Ltd | Guanidine derivatives their production and insecticides |
| IL93159A (en) | 1989-01-31 | 1996-11-14 | Takeda Chemical Industries Ltd | Process for the production of 1,1,1-trihalogen-2-nitroethanes |
| GB2228003A (en) | 1989-02-13 | 1990-08-15 | Shell Int Research | Pesticidal nitroethene compounds |
| ES2059841T3 (es) | 1989-02-13 | 1994-11-16 | Bayer Agrochem Kk | Nitro compuestos con actividad insecticida. |
| JP2610988B2 (ja) | 1989-03-09 | 1997-05-14 | 日本バイエルアグロケム 株式会社 | 新規ヘテロ環式化合物及び殺虫剤 |
| IL99161A (en) * | 1990-08-17 | 1996-11-14 | Takeda Chemical Industries Ltd | History of guanidine A process for their preparation and preparations from pesticides that contain them |
| IL99445A (en) | 1990-09-18 | 1996-06-18 | Ciba Geigy Ag | Picoline oxides process for their preparation and insecticidal and acaricidal compositions containing them |
| DE4207604A1 (de) | 1991-03-13 | 1992-09-17 | Ciba Geigy Ag | Schaedlingsbekaempfungsmittel |
| JPH05112521A (ja) * | 1991-03-22 | 1993-05-07 | Takeda Chem Ind Ltd | ニトログアニジン誘導体の製造方法、その中間体及びその製造方法 |
| JPH0511251A (ja) | 1991-07-01 | 1993-01-19 | Canon Inc | 高分子液晶の配向方法および高分子液晶素子 |
| JP2783912B2 (ja) | 1992-05-23 | 1998-08-06 | ノバルティス アクチェンゲゼルシャフト | 家畜内の蚤を駆除するための1−〔n−(ハロ−3−ピリジルメチル)〕−n−メチルアミノ−1−アルキルアミノ−2−ニトロエチレン誘導体 |
| DE4232561A1 (de) | 1992-09-29 | 1994-03-31 | Bayer Ag | Bekämpfung von Fischparasiten |
| AU4297197A (en) * | 1996-08-08 | 1998-03-06 | Novartis Ag | Substituted 4-nitroimino-perhydro-1,3,5-oxadiazine derivatives, their use as pesticides and intermediates for their preparation |
-
1999
- 1999-11-12 CO CO99071586A patent/CO5210925A1/es not_active Application Discontinuation
- 1999-11-15 NZ NZ511380A patent/NZ511380A/en unknown
- 1999-11-15 TW TW088119841A patent/TW561149B/zh not_active IP Right Cessation
- 1999-11-15 IL IL14268799A patent/IL142687A0/xx active IP Right Grant
- 1999-11-15 AU AU15531/00A patent/AU762529B2/en not_active Ceased
- 1999-11-15 EP EP99958038A patent/EP1131292B1/en not_active Expired - Lifetime
- 1999-11-15 RU RU2001116594/04A patent/RU2245877C2/ru not_active IP Right Cessation
- 1999-11-15 BR BR9915430-7A patent/BR9915430A/pt not_active Application Discontinuation
- 1999-11-15 WO PCT/EP1999/008765 patent/WO2000029378A2/en not_active Ceased
- 1999-11-15 ES ES99958038T patent/ES2255766T3/es not_active Expired - Lifetime
- 1999-11-15 KR KR1020017006159A patent/KR100620470B1/ko not_active Expired - Fee Related
- 1999-11-15 AR ARP990105795A patent/AR023703A1/es unknown
- 1999-11-15 DK DK99958038T patent/DK1131292T3/da active
- 1999-11-15 HK HK02100209.5A patent/HK1038563B/en not_active IP Right Cessation
- 1999-11-15 JP JP2000582365A patent/JP2002529532A/ja not_active Withdrawn
- 1999-11-15 PT PT99958038T patent/PT1131292E/pt unknown
- 1999-11-15 DE DE69929820T patent/DE69929820T2/de not_active Expired - Fee Related
- 1999-11-15 CA CA002350742A patent/CA2350742A1/en not_active Abandoned
- 1999-11-15 CN CNB998133175A patent/CN1177823C/zh not_active Expired - Fee Related
- 1999-11-15 AT AT99958038T patent/ATE317385T1/de not_active IP Right Cessation
-
2001
- 2001-04-19 IL IL142687A patent/IL142687A/en not_active IP Right Cessation
- 2001-05-07 US US09/850,378 patent/US6538013B2/en not_active Expired - Fee Related
-
2003
- 2003-01-21 US US10/348,574 patent/US6759407B2/en not_active Expired - Fee Related
-
2004
- 2004-02-17 US US10/779,932 patent/US7271184B2/en not_active Expired - Fee Related
-
2006
- 2006-05-04 CY CY20061100580T patent/CY1106083T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20020028806A1 (en) | 2002-03-07 |
| NZ511380A (en) | 2003-10-31 |
| US20030203891A1 (en) | 2003-10-30 |
| AU762529B2 (en) | 2003-06-26 |
| EP1131292A2 (en) | 2001-09-12 |
| JP2002529532A (ja) | 2002-09-10 |
| DK1131292T3 (da) | 2006-04-18 |
| CN1326442A (zh) | 2001-12-12 |
| CO5210925A1 (es) | 2002-10-30 |
| EP1131292B1 (en) | 2006-02-08 |
| RU2245877C2 (ru) | 2005-02-10 |
| IL142687A (en) | 2006-10-05 |
| IL142687A0 (en) | 2002-03-10 |
| WO2000029378A3 (en) | 2000-12-14 |
| KR20010086445A (ko) | 2001-09-12 |
| BR9915430A (pt) | 2001-08-07 |
| WO2000029378A2 (en) | 2000-05-25 |
| KR100620470B1 (ko) | 2006-09-13 |
| CA2350742A1 (en) | 2000-05-25 |
| AR023703A1 (es) | 2002-09-04 |
| TW561149B (en) | 2003-11-11 |
| PT1131292E (pt) | 2006-06-30 |
| CN1177823C (zh) | 2004-12-01 |
| HK1038563B (en) | 2006-11-24 |
| US20040162283A1 (en) | 2004-08-19 |
| DE69929820D1 (de) | 2006-04-20 |
| US7271184B2 (en) | 2007-09-18 |
| HK1038563A1 (en) | 2002-03-22 |
| ATE317385T1 (de) | 2006-02-15 |
| AU1553100A (en) | 2000-06-05 |
| US6759407B2 (en) | 2004-07-06 |
| DE69929820T2 (de) | 2006-07-27 |
| CY1106083T1 (el) | 2011-06-08 |
| US6538013B2 (en) | 2003-03-25 |
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