WO2003106427A2 - Pyrazolecarboxamide insecticides - Google Patents
Pyrazolecarboxamide insecticides Download PDFInfo
- Publication number
- WO2003106427A2 WO2003106427A2 PCT/US2003/018609 US0318609W WO03106427A2 WO 2003106427 A2 WO2003106427 A2 WO 2003106427A2 US 0318609 W US0318609 W US 0318609W WO 03106427 A2 WO03106427 A2 WO 03106427A2
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- 239000002917 insecticide Substances 0.000 title description 9
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 176
- 239000000203 mixture Substances 0.000 claims abstract description 85
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 56
- 238000000034 method Methods 0.000 claims abstract description 38
- 239000007787 solid Substances 0.000 claims abstract description 26
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 21
- 125000001424 substituent group Chemical group 0.000 claims abstract description 21
- 239000003085 diluting agent Substances 0.000 claims abstract description 20
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 14
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 14
- 239000004094 surface-active agent Substances 0.000 claims abstract description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 11
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims abstract description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 9
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 502
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 483
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 296
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 170
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 150000002367 halogens Chemical group 0.000 claims description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 11
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 11
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 7
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 7
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 2
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1157
- 239000000460 chlorine Substances 0.000 description 318
- -1 heterocyclic amides Chemical class 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 238000012360 testing method Methods 0.000 description 33
- 125000006414 CCl Chemical group ClC* 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
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- 239000000047 product Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000008187 granular material Substances 0.000 description 12
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 12
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
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- 239000002253 acid Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 230000006378 damage Effects 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
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- 241000256247 Spodoptera exigua Species 0.000 description 6
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
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- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-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
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered 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
- A01N43/48—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
-
- 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
- C07D401/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP03739103A EP1511733A2 (en) | 2002-06-13 | 2003-06-10 | Pyrazole and pyrrole carboxamide insecticides |
JP2004513260A JP4287816B2 (en) | 2002-06-13 | 2003-06-10 | Pyrazole carboxamide insecticide |
MXPA04012214A MXPA04012214A (en) | 2002-06-13 | 2003-06-10 | Pyrazolecarboxamide insecticides. |
BR0311707-3A BR0311707A (en) | 2002-06-13 | 2003-06-10 | Compound, composition and method of control of at least one invertebrate pest |
US10/514,183 US7754738B2 (en) | 2002-06-13 | 2003-06-10 | Pyrazole and pyrrole carboxamide insecticides |
AU2003245464A AU2003245464A1 (en) | 2002-06-13 | 2003-06-10 | Pyrazole and pyrrole carboxamide insecticides |
KR10-2004-7020187A KR20050009747A (en) | 2002-06-13 | 2003-06-10 | Pyrazolecarboxamide insecticides |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US38824402P | 2002-06-13 | 2002-06-13 | |
US60/388,244 | 2002-06-13 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2003106427A2 true WO2003106427A2 (en) | 2003-12-24 |
WO2003106427A3 WO2003106427A3 (en) | 2004-06-24 |
Family
ID=29736447
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2003/018609 WO2003106427A2 (en) | 2002-06-13 | 2003-06-10 | Pyrazolecarboxamide insecticides |
Country Status (9)
Country | Link |
---|---|
US (1) | US7754738B2 (en) |
EP (1) | EP1511733A2 (en) |
JP (1) | JP4287816B2 (en) |
KR (1) | KR20050009747A (en) |
CN (1) | CN100335477C (en) |
AU (1) | AU2003245464A1 (en) |
BR (1) | BR0311707A (en) |
MX (1) | MXPA04012214A (en) |
WO (1) | WO2003106427A2 (en) |
Cited By (36)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2004046129A2 (en) * | 2002-11-15 | 2004-06-03 | E.I. Du Pont De Nemours And Company | Novel anthranilamide insecticides |
WO2007024833A1 (en) * | 2005-08-24 | 2007-03-01 | E. I. Du Pont De Nemours And Company | Anthranilamides for controlling invertebrate pests |
US7199138B2 (en) | 2001-08-16 | 2007-04-03 | E. I. Du Pont De Nemours And Company | Substituted anthranilamides for controlling invertebrate pests |
US7232836B2 (en) | 2001-08-13 | 2007-06-19 | E. I. Du Pont De Nemours And Company | Arthropodicidal anthranilamides |
EP1803709A1 (en) * | 2004-09-30 | 2007-07-04 | Takeda Pharmaceutical Company Limited | Proton pump inhibitors |
US7247647B2 (en) | 2003-01-28 | 2007-07-24 | E. I. Du Pont De Nemours And Company | Cyano anthranilamide insecticides |
US7276601B2 (en) | 2003-06-12 | 2007-10-02 | E.I. Du Pont De Nemours And Company | Method and preparing fused oxazinones |
US7288554B2 (en) | 2001-08-15 | 2007-10-30 | E.I. Du Pont De Nemours And Company | Ortho-substituted aryl amides for controlling invertebrate pests |
WO2008149382A1 (en) * | 2007-06-08 | 2008-12-11 | Advinus Therapeutics Private Limited | Pyrrole-2-carboxamide derivatives as glucokinase activators, their process and pharmaceutical application |
WO2009018065A2 (en) * | 2007-07-27 | 2009-02-05 | Bristol-Myers Squibb Company | Novel glucokinase activators and methods of using same |
US7696232B2 (en) | 2001-09-21 | 2010-04-13 | E. I. Du Pont De Nemours And Company | Anthranilamide arthropodicide treatment |
US7696233B2 (en) | 2001-08-13 | 2010-04-13 | E. I. Du Pont De Nemours And Company | Method for controlling particular insect pests by applying anthranilamide compounds |
WO2010034738A3 (en) * | 2008-09-24 | 2010-10-07 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
WO2011003796A1 (en) | 2009-07-06 | 2011-01-13 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
US7977488B2 (en) | 2005-08-30 | 2011-07-12 | Takeda Pharmaceutical Company Limited | 1-heterocyclylsulfonyl, 2-aminomethyl, 5-(hetero-) aryl substituted 1-H-pyrrole derivatives as acid secretion inhibitors |
WO2011117804A1 (en) | 2010-03-23 | 2011-09-29 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
WO2011117286A1 (en) | 2010-03-23 | 2011-09-29 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
WO2011157663A1 (en) * | 2010-06-15 | 2011-12-22 | Bayer Cropscience Ag | Novel ortho-substituted aryl amide derivatives |
WO2013024007A1 (en) | 2011-08-12 | 2013-02-21 | Basf Se | Process for preparing n-substituted 1h-pyrazole-5-carbonylchloride compounds |
WO2013024008A1 (en) | 2011-08-12 | 2013-02-21 | Basf Se | Aniline type compounds |
WO2013024170A1 (en) | 2011-08-18 | 2013-02-21 | Basf Se | Carbamoylmethoxy- and carbamoylmethylthio- and carbamoylmethylamino benzamides for combating invertebrate pests |
WO2013024010A1 (en) | 2011-08-12 | 2013-02-21 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
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US8389552B2 (en) | 2008-09-11 | 2013-03-05 | Pfizer Inc. | (S)-6-(2-(4-(cyclobutylsulfonyl)-1H-imidazol-1-yl)-3-cyclopentylpropanamido)nicotinic acid useful as a glucokinase activator |
WO2013076092A1 (en) | 2011-11-21 | 2013-05-30 | Basf Se | Process for preparing n-substituted 1h-pyrazole-5-carboxylate compounds and derivatives thereof |
US8455496B2 (en) | 2009-03-11 | 2013-06-04 | Pfizer Inc. | Benzofuranyl derivatives |
WO2013117601A1 (en) | 2012-02-07 | 2013-08-15 | Bayer Intellectual Property Gmbh | Method for producing substituted anthranilic acid derivatives |
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US8642597B2 (en) | 2007-08-27 | 2014-02-04 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
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WO2003016304A1 (en) * | 2001-08-15 | 2003-02-27 | E. I. Du Pont De Nemours And Company | Ortho-heterocyclic substituted aryl amides for controlling invertebrate pests |
WO2003016300A1 (en) * | 2001-08-15 | 2003-02-27 | E. I. Du Pont De Nemours And Company | Ortho-substituted aryl amides for controlling invertebrate pests |
WO2003027099A1 (en) * | 2001-09-21 | 2003-04-03 | E. I. Du Pont De Nemours And Company | Arthropodicidal anthranilamides |
WO2003026415A2 (en) * | 2001-09-21 | 2003-04-03 | E.I. Du Pont De Nemours And Company | Insecticidal diamides |
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-
2003
- 2003-06-10 KR KR10-2004-7020187A patent/KR20050009747A/en not_active Application Discontinuation
- 2003-06-10 MX MXPA04012214A patent/MXPA04012214A/en not_active Application Discontinuation
- 2003-06-10 AU AU2003245464A patent/AU2003245464A1/en not_active Abandoned
- 2003-06-10 EP EP03739103A patent/EP1511733A2/en not_active Withdrawn
- 2003-06-10 CN CNB038127318A patent/CN100335477C/en not_active Expired - Fee Related
- 2003-06-10 US US10/514,183 patent/US7754738B2/en not_active Expired - Fee Related
- 2003-06-10 JP JP2004513260A patent/JP4287816B2/en not_active Expired - Fee Related
- 2003-06-10 BR BR0311707-3A patent/BR0311707A/en not_active IP Right Cessation
- 2003-06-10 WO PCT/US2003/018609 patent/WO2003106427A2/en active Application Filing
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US7696233B2 (en) | 2001-08-13 | 2010-04-13 | E. I. Du Pont De Nemours And Company | Method for controlling particular insect pests by applying anthranilamide compounds |
US8148521B2 (en) | 2001-08-13 | 2012-04-03 | E.I. Du Pont De Nemours And Company | Arthropodicidal anthranilamides |
US9445593B1 (en) | 2001-08-13 | 2016-09-20 | E I Du Pont De Nemours And Company | Arthropodicidal anthranilamides |
US8158802B2 (en) | 2001-08-13 | 2012-04-17 | E.I. Du Pont De Nemours And Company | Arthropodicidal anthranilamides |
US7232836B2 (en) | 2001-08-13 | 2007-06-19 | E. I. Du Pont De Nemours And Company | Arthropodicidal anthranilamides |
US8697734B2 (en) | 2001-08-13 | 2014-04-15 | E I Du Pont De Nemours And Company | Method for controlling particular insect pests by applying anthranilamide compounds |
US9029365B2 (en) | 2001-08-13 | 2015-05-12 | E I Du Pont De Nemours And Company | Arthropodicidal anthranilamides |
US9049862B2 (en) | 2001-08-13 | 2015-06-09 | E I Du Pont De Nemours And Company | Arthropodicidal anthranilamides |
US9084422B2 (en) | 2001-08-13 | 2015-07-21 | E I Du Pont De Nemours And Company | Anthranilamides compositions |
US9078437B2 (en) | 2001-08-13 | 2015-07-14 | E I Du Pont De Nemours And Company | Arthropodicidal anthranilamides |
US9049861B2 (en) | 2001-08-13 | 2015-06-09 | E I Du Pont De Nemours And Company | Arthropodicidal anthranilamides |
US7288554B2 (en) | 2001-08-15 | 2007-10-30 | E.I. Du Pont De Nemours And Company | Ortho-substituted aryl amides for controlling invertebrate pests |
US7541377B2 (en) | 2001-08-16 | 2009-06-02 | E.I. Du Pont De Nemours And Company | Substituted anthranilamides for controlling invertebrate pests |
US7199138B2 (en) | 2001-08-16 | 2007-04-03 | E. I. Du Pont De Nemours And Company | Substituted anthranilamides for controlling invertebrate pests |
US7696232B2 (en) | 2001-09-21 | 2010-04-13 | E. I. Du Pont De Nemours And Company | Anthranilamide arthropodicide treatment |
US8637552B2 (en) | 2001-09-21 | 2014-01-28 | E I Du Pont De Nemours And Company | Anthranilamide arthropodicide treatment |
US7666882B2 (en) | 2002-11-15 | 2010-02-23 | E.I. Du Pont De Nemours And Company | Anthranilamide insecticides |
WO2004046129A3 (en) * | 2002-11-15 | 2004-07-15 | Du Pont | Novel anthranilamide insecticides |
WO2004046129A2 (en) * | 2002-11-15 | 2004-06-03 | E.I. Du Pont De Nemours And Company | Novel anthranilamide insecticides |
US8475819B2 (en) | 2003-01-28 | 2013-07-02 | E I Du Pont De Nemours And Company | Cyano anthranilamide insecticides |
US7247647B2 (en) | 2003-01-28 | 2007-07-24 | E. I. Du Pont De Nemours And Company | Cyano anthranilamide insecticides |
US7875634B2 (en) | 2003-01-28 | 2011-01-25 | E. I. Du Pont De Nemours And Company | Cyano anthranilamide insecticides |
US7276601B2 (en) | 2003-06-12 | 2007-10-02 | E.I. Du Pont De Nemours And Company | Method and preparing fused oxazinones |
US8048909B2 (en) | 2004-09-30 | 2011-11-01 | Takeda Pharmaceutical Company Limited | Proton pump inhibitors |
EP1803709A1 (en) * | 2004-09-30 | 2007-07-04 | Takeda Pharmaceutical Company Limited | Proton pump inhibitors |
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CN100335477C (en) | 2007-09-05 |
EP1511733A2 (en) | 2005-03-09 |
WO2003106427A3 (en) | 2004-06-24 |
BR0311707A (en) | 2005-03-15 |
KR20050009747A (en) | 2005-01-25 |
AU2003245464A1 (en) | 2003-12-31 |
US7754738B2 (en) | 2010-07-13 |
MXPA04012214A (en) | 2005-02-25 |
US20060167060A1 (en) | 2006-07-27 |
JP2005532367A (en) | 2005-10-27 |
CN1659160A (en) | 2005-08-24 |
JP4287816B2 (en) | 2009-07-01 |
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