ES2436746T3 - Derivados pesticidas de 5-(acilamino)pirazol - Google Patents
Derivados pesticidas de 5-(acilamino)pirazol Download PDFInfo
- Publication number
- ES2436746T3 ES2436746T3 ES03779895.6T ES03779895T ES2436746T3 ES 2436746 T3 ES2436746 T3 ES 2436746T3 ES 03779895 T ES03779895 T ES 03779895T ES 2436746 T3 ES2436746 T3 ES 2436746T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- halo
- compound
- group
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000575 pesticide Substances 0.000 title claims description 14
- 125000004442 acylamino group Chemical group 0.000 title description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 170
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 64
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 48
- 150000002367 halogens Chemical class 0.000 claims abstract description 47
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 19
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
- 125000001424 substituent group Chemical group 0.000 claims abstract description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims abstract description 5
- 229910006069 SO3H Inorganic materials 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 5
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 4
- 125000001118 alkylidene group Chemical group 0.000 claims abstract 2
- -1 halo (C1-C6) alkyl Chemical group 0.000 claims description 106
- 239000000203 mixture Substances 0.000 claims description 93
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 74
- 150000003839 salts Chemical class 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 39
- 241000607479 Yersinia pestis Species 0.000 claims description 38
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 229910052721 tungsten Inorganic materials 0.000 claims description 12
- 239000004094 surface-active agent Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 9
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 230000010933 acylation Effects 0.000 claims description 5
- 238000005917 acylation reaction Methods 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 5
- 125000006413 ring segment Chemical group 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 230000007717 exclusion Effects 0.000 claims description 3
- 101100134929 Gallus gallus COR9 gene Proteins 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 abstract description 6
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 118
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 90
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 83
- 239000000460 chlorine Substances 0.000 description 33
- 241000196324 Embryophyta Species 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 150000003254 radicals Chemical class 0.000 description 29
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- 239000000843 powder Substances 0.000 description 23
- 239000004480 active ingredient Substances 0.000 description 20
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 241000238876 Acari Species 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
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- 239000008187 granular material Substances 0.000 description 15
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
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- 239000013543 active substance Substances 0.000 description 12
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 12
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 12
- 125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 description 12
- 239000003981 vehicle Substances 0.000 description 12
- 241000255925 Diptera Species 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 241000209149 Zea Species 0.000 description 10
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- 238000009472 formulation Methods 0.000 description 10
- 238000010626 work up procedure Methods 0.000 description 10
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 9
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- 241000254173 Coleoptera Species 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 244000000013 helminth Species 0.000 description 8
- 238000005507 spraying Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- QFMDFTQOJHFVNR-UHFFFAOYSA-N 1-[2,2-dichloro-1-(4-ethylphenyl)ethyl]-4-ethylbenzene Chemical compound C1=CC(CC)=CC=C1C(C(Cl)Cl)C1=CC=C(CC)C=C1 QFMDFTQOJHFVNR-UHFFFAOYSA-N 0.000 description 7
- 206010061217 Infestation Diseases 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000012216 screening Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 6
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- 239000000975 dye Substances 0.000 description 6
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- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
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- 230000000361 pesticidal effect Effects 0.000 description 6
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- 230000009261 transgenic effect Effects 0.000 description 6
- 241000239223 Arachnida Species 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
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- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
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- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
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- 229940108410 resmethrin Drugs 0.000 description 1
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- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 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 1
- 239000000377 silicon dioxide Substances 0.000 description 1
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- MFSDELSXOVOZBJ-UHFFFAOYSA-M sodium;dodecyl sulfate;propane-1,2,3-triol Chemical compound [Na+].OCC(O)CO.CCCCCCCCCCCCOS([O-])(=O)=O MFSDELSXOVOZBJ-UHFFFAOYSA-M 0.000 description 1
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- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
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- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- AWYOMXWDGWUJHS-UHFFFAOYSA-N tebupirimfos Chemical compound CCOP(=S)(OC(C)C)OC1=CN=C(C(C)(C)C)N=C1 AWYOMXWDGWUJHS-UHFFFAOYSA-N 0.000 description 1
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- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
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- 239000011573 trace mineral Substances 0.000 description 1
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- JWXZLCFGVKMEEK-UHFFFAOYSA-N triarathene Chemical compound C1=CC(Cl)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 JWXZLCFGVKMEEK-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02027062 | 2002-12-03 | ||
| EP02027062 | 2002-12-03 | ||
| PCT/EP2003/012619 WO2004049803A1 (en) | 2002-12-03 | 2003-11-12 | Pesticidal 5- (acylamino) pyrazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2436746T3 true ES2436746T3 (es) | 2014-01-07 |
Family
ID=32405692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03779895.6T Expired - Lifetime ES2436746T3 (es) | 2002-12-03 | 2003-11-12 | Derivados pesticidas de 5-(acilamino)pirazol |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7514561B2 (https=) |
| EP (1) | EP1569517B1 (https=) |
| JP (1) | JP4759682B2 (https=) |
| KR (1) | KR101288753B1 (https=) |
| CN (2) | CN1944413A (https=) |
| AR (1) | AR042255A1 (https=) |
| AU (1) | AU2003288038B2 (https=) |
| BR (1) | BRPI0316993B1 (https=) |
| CA (1) | CA2508412C (https=) |
| CO (1) | CO5690506A2 (https=) |
| EA (1) | EA011505B1 (https=) |
| ES (1) | ES2436746T3 (https=) |
| MX (1) | MXPA05005899A (https=) |
| NZ (1) | NZ540462A (https=) |
| WO (1) | WO2004049803A1 (https=) |
| ZA (1) | ZA200503743B (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090048258A1 (en) * | 2005-02-01 | 2009-02-19 | Masaki Ogino | Amide Compound |
| US20080176826A1 (en) * | 2005-05-25 | 2008-07-24 | Michael Puhl | Pyridine Compounds For Combating Arthropod Pests and Nematodes |
| MY155497A (en) | 2008-11-19 | 2015-10-30 | Merial Inc | Compositions comprising an aryl pyrazole and/or a formamidine, methods and use thereof |
| UA108641C2 (uk) | 2010-04-02 | 2015-05-25 | Паразитицидна композиція, яка містить чотири активних агенти, та спосіб її застосування | |
| JP6027128B2 (ja) * | 2011-10-26 | 2016-11-16 | ダウ アグロサイエンシィズ エルエルシー | 有害生物防除組成物およびそれに関連した方法 |
| AU2012340351B2 (en) | 2011-11-17 | 2017-06-15 | Boehringer Ingelheim Animal Health USA Inc. | Compositions comprising an aryl pyrazole and a substituted imidazole, methods and uses thereof |
| CA2926095A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| JP2016539092A (ja) | 2013-10-17 | 2016-12-15 | ダウ アグロサイエンシィズ エルエルシー | 有害生物防除性化合物の製造方法 |
| US9029554B1 (en) | 2013-10-17 | 2015-05-12 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| EP3057429A4 (en) | 2013-10-17 | 2017-08-09 | Dow AgroSciences LLC | Processes for the preparation of pesticidal compounds |
| CA2925953C (en) | 2013-10-17 | 2021-11-02 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| CA2925952A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
| MX2016004941A (es) * | 2013-10-17 | 2016-06-28 | Dow Agrosciences Llc | Proceso para la preparacion de compuestos plaguicidas. |
| GB201322334D0 (en) | 2013-12-17 | 2014-01-29 | Agency Science Tech & Res | Maleimide derivatives as modulators of WNT pathway |
| BR112017000293A2 (pt) | 2014-07-31 | 2017-10-31 | Dow Agrosciences Llc | processo para a preparação de 3-(3-cloro-1h-pirazol-1-il)piridina |
| JP2017523168A (ja) | 2014-07-31 | 2017-08-17 | ダウ アグロサイエンシィズ エルエルシー | ３−（３−クロロ−１ｈ−ピラゾール−１−イル）ピリジンの製造方法 |
| US9249122B1 (en) | 2014-07-31 | 2016-02-02 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine |
| JP2017525703A (ja) | 2014-08-19 | 2017-09-07 | ダウ アグロサイエンシィズ エルエルシー | ３−（３−クロロ−１ｈ−ピラゾール−１−イル）ピリジンの調製方法 |
| AR098113A1 (es) | 2014-09-12 | 2016-05-04 | Dow Agrosciences Llc | Proceso para la preparación de 3-(3-cloro-1h-pirazol-1-il)piridina |
| US10864193B2 (en) | 2014-10-31 | 2020-12-15 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal compositions comprising fipronil at high concentrations |
| WO2016163379A1 (ja) * | 2015-04-09 | 2016-10-13 | 住友化学株式会社 | オキサリルアミド化合物及びその有害節足動物防除用途 |
| WO2016163383A1 (ja) * | 2015-04-09 | 2016-10-13 | 住友化学株式会社 | オキサリルアミド化合物及びその有害節足動物防除用途 |
| CN105732505B (zh) * | 2016-01-28 | 2018-10-12 | 中南民族大学 | 丙烯酰胺化芳基吡唑型化合物及其溶剂热一锅合成法与应用 |
| CN105712933B (zh) * | 2016-01-28 | 2019-01-11 | 中南民族大学 | 甲酰化芳基吡唑衍生物及其醚热合成方法和应用 |
| CN106417329B (zh) * | 2016-09-27 | 2019-08-27 | 辽宁省蚕业科学研究所 | 一类柞蚕饰腹寄蝇病防治化合物及使用方法 |
| JP2020503336A (ja) | 2016-12-29 | 2020-01-30 | ダウ アグロサイエンシィズ エルエルシー | 殺有害生物化合物の調製方法 |
| CN110325036B (zh) | 2016-12-29 | 2021-10-26 | 美国陶氏益农公司 | 用于制备杀虫化合物的方法 |
| CN107629005A (zh) * | 2017-08-22 | 2018-01-26 | 王泊理 | 多取代苯基吡唑衍生物及其制备方法和用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3602728A1 (de) | 1985-05-17 | 1986-11-20 | Bayer Ag, 51373 Leverkusen | Schaedlingsbekaempfungsmittel auf basis von pyrazolderivaten |
| GB8713768D0 (en) | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| US5232940A (en) | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
| GB8531485D0 (en) | 1985-12-20 | 1986-02-05 | May & Baker Ltd | Compositions of matter |
| GB9120641D0 (en) | 1991-09-27 | 1991-11-06 | Ici Plc | Heterocyclic compounds |
| US5556873A (en) | 1993-02-24 | 1996-09-17 | Rhone-Poulenc Inc. | Pesticidal 1-aryl-5-(substituted alkyl (thio) amido)pyrazoles |
| GB9306184D0 (en) | 1993-03-25 | 1993-05-19 | Zeneca Ltd | Heteroaromatic compounds |
| DE4343832A1 (de) | 1993-12-22 | 1995-06-29 | Bayer Ag | Substituierte 1-Arylpyrazole |
| DE4414333A1 (de) | 1994-04-25 | 1995-10-26 | Bayer Ag | Substituierte Pyridylpyrazole |
| US6316477B1 (en) | 1996-01-30 | 2001-11-13 | Takeda Chemical Industries, Ltd. | Arylpyrazole insecticides |
| EP0811615A1 (en) * | 1996-06-03 | 1997-12-10 | Rhone-Poulenc Agrochimie | 1-Aryl-5-(substituted alkyl (thio) amido) pyrazoles and their use as pesticides |
| JP3735159B2 (ja) * | 1996-06-17 | 2006-01-18 | ローヌ−プーラン・アグロシミ | 新規な農薬 |
| GB9625045D0 (en) | 1996-11-30 | 1997-01-22 | Pfizer Ltd | Parasiticidal compounds |
| DE19650197A1 (de) | 1996-12-04 | 1998-06-10 | Bayer Ag | 3-Thiocarbamoylpyrazol-Derivate |
| AR021608A1 (es) | 1998-12-11 | 2002-07-31 | Merial Ltd | Represion de artropodos en animales |
-
2003
- 2003-11-12 US US10/537,547 patent/US7514561B2/en not_active Expired - Lifetime
- 2003-11-12 JP JP2004556131A patent/JP4759682B2/ja not_active Expired - Fee Related
- 2003-11-12 WO PCT/EP2003/012619 patent/WO2004049803A1/en not_active Ceased
- 2003-11-12 MX MXPA05005899A patent/MXPA05005899A/es active IP Right Grant
- 2003-11-12 CA CA2508412A patent/CA2508412C/en not_active Expired - Fee Related
- 2003-11-12 CN CNA2006101492437A patent/CN1944413A/zh active Pending
- 2003-11-12 NZ NZ540462A patent/NZ540462A/en not_active IP Right Cessation
- 2003-11-12 BR BRPI0316993A patent/BRPI0316993B1/pt not_active IP Right Cessation
- 2003-11-12 AU AU2003288038A patent/AU2003288038B2/en not_active Ceased
- 2003-11-12 EP EP03779895.6A patent/EP1569517B1/en not_active Expired - Lifetime
- 2003-11-12 CN CNA2003801048559A patent/CN1719974A/zh active Pending
- 2003-11-12 KR KR1020057009951A patent/KR101288753B1/ko not_active Expired - Fee Related
- 2003-11-12 EA EA200500930A patent/EA011505B1/ru not_active IP Right Cessation
- 2003-11-12 ES ES03779895.6T patent/ES2436746T3/es not_active Expired - Lifetime
- 2003-12-01 AR ARP030104421A patent/AR042255A1/es active IP Right Grant
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2005
- 2005-05-10 ZA ZA200503743A patent/ZA200503743B/en unknown
- 2005-05-31 CO CO05052700A patent/CO5690506A2/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| EP1569517A1 (en) | 2005-09-07 |
| JP4759682B2 (ja) | 2011-08-31 |
| EA011505B1 (ru) | 2009-04-28 |
| BRPI0316993B1 (pt) | 2016-07-05 |
| MXPA05005899A (es) | 2005-08-29 |
| KR20050084103A (ko) | 2005-08-26 |
| BR0316993A (pt) | 2005-10-25 |
| CA2508412C (en) | 2011-07-26 |
| EP1569517B1 (en) | 2013-10-02 |
| AU2003288038B2 (en) | 2009-04-23 |
| US20060135778A1 (en) | 2006-06-22 |
| CA2508412A1 (en) | 2004-06-17 |
| AU2003288038A1 (en) | 2004-06-23 |
| US7514561B2 (en) | 2009-04-07 |
| WO2004049803A1 (en) | 2004-06-17 |
| CO5690506A2 (es) | 2006-10-31 |
| EA200500930A1 (ru) | 2006-10-27 |
| AR042255A1 (es) | 2005-06-15 |
| CN1944413A (zh) | 2007-04-11 |
| ZA200503743B (en) | 2006-11-29 |
| KR101288753B1 (ko) | 2013-07-23 |
| NZ540462A (en) | 2008-03-28 |
| CN1719974A (zh) | 2006-01-11 |
| JP2006509004A (ja) | 2006-03-16 |
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