AU2012356947A1 - Isothiazoline compounds for combating invertebrate pests - Google Patents
Isothiazoline compounds for combating invertebrate pests Download PDFInfo
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- AU2012356947A1 AU2012356947A1 AU2012356947A AU2012356947A AU2012356947A1 AU 2012356947 A1 AU2012356947 A1 AU 2012356947A1 AU 2012356947 A AU2012356947 A AU 2012356947A AU 2012356947 A AU2012356947 A AU 2012356947A AU 2012356947 A1 AU2012356947 A1 AU 2012356947A1
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- Australia
- Prior art keywords
- alkyl
- ring
- group
- cycloalkyl
- 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.)
- Abandoned
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- 241000607479 Yersinia pestis Species 0.000 title claims abstract description 30
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical class C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 1040
- 238000000034 method Methods 0.000 claims abstract description 42
- 239000000463 material Substances 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 15
- -1 aliphatic radicals Chemical class 0.000 claims description 717
- 235000013350 formula milk Nutrition 0.000 claims description 517
- 125000005842 heteroatom Chemical group 0.000 claims description 259
- 125000001424 substituent group Chemical group 0.000 claims description 242
- 150000003254 radicals Chemical class 0.000 claims description 205
- 125000000623 heterocyclic group Chemical group 0.000 claims description 191
- 229910052739 hydrogen Inorganic materials 0.000 claims description 186
- 239000001257 hydrogen Substances 0.000 claims description 186
- 150000002431 hydrogen Chemical class 0.000 claims description 137
- 229910052736 halogen Inorganic materials 0.000 claims description 135
- 150000002367 halogens Chemical class 0.000 claims description 135
- 229910052717 sulfur Inorganic materials 0.000 claims description 135
- 229920006395 saturated elastomer Polymers 0.000 claims description 112
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 105
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 99
- 229910052799 carbon Inorganic materials 0.000 claims description 94
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 82
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 78
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 75
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 67
- 229910052757 nitrogen Inorganic materials 0.000 claims description 67
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 65
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 64
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 63
- 125000001931 aliphatic group Chemical group 0.000 claims description 48
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 46
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 28
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 28
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 16
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000002243 precursor Substances 0.000 claims description 14
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 13
- 241001465754 Metazoa Species 0.000 claims description 12
- 238000005576 amination reaction Methods 0.000 claims description 12
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 11
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 10
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 206010061217 Infestation Diseases 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 238000009395 breeding Methods 0.000 claims description 6
- 230000001488 breeding effect Effects 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 6
- 238000005580 one pot reaction Methods 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 6
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 5
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
- 230000002633 protecting effect Effects 0.000 claims description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 230000036961 partial effect Effects 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 3
- HCUOEKSZWPGJIM-IYNMRSRQSA-N (e,2z)-2-hydroxyimino-6-methoxy-4-methyl-5-nitrohex-3-enamide Chemical compound COCC([N+]([O-])=O)\C(C)=C\C(=N\O)\C(N)=O HCUOEKSZWPGJIM-IYNMRSRQSA-N 0.000 claims description 3
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 235000013305 food Nutrition 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 230000000361 pesticidal effect Effects 0.000 claims description 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 125000004766 (C3-C6) cyclohaloalkyl group Chemical group 0.000 claims description 2
- 101100489581 Caenorhabditis elegans par-5 gene Proteins 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 2
- 241000251539 Vertebrata <Metazoa> Species 0.000 claims 2
- FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 claims 1
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 1
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 1
- 102220511609 Kappa-casein_R16E_mutation Human genes 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000012025 fluorinating agent Substances 0.000 claims 1
- 238000003682 fluorination reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 claims 1
- 241000244206 Nematoda Species 0.000 abstract description 9
- 241000238421 Arthropoda Species 0.000 abstract description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 102000004169 proteins and genes Human genes 0.000 description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
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- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
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| US201161579676P | 2011-12-23 | 2011-12-23 | |
| US61/579,676 | 2011-12-23 | ||
| PCT/EP2012/076539 WO2013092943A1 (en) | 2011-12-23 | 2012-12-21 | Isothiazoline compounds for combating invertebrate pests |
Publications (1)
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| AU2012356947A1 true AU2012356947A1 (en) | 2014-07-10 |
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Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103842358A (zh) * | 2011-09-13 | 2014-06-04 | 先正达参股股份有限公司 | 作为杀虫化合物的异噻唑啉衍生物 |
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| CN105472987B (zh) * | 2013-06-21 | 2017-08-04 | 巴斯夫欧洲公司 | 包含异噻唑啉杀虫剂和活性炭的悬浮液浓缩物组合物 |
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| JP2016527208A (ja) * | 2013-06-24 | 2016-09-08 | メリアル インコーポレイテッド | 無脊椎有害生物を駆除するためのイソチアゾリン化合物 |
| US10093634B2 (en) | 2013-12-18 | 2018-10-09 | BASF Agro B.V. | Process for the preparation of substituted phenoxyphenyl ketones |
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| LT3303330T (lt) | 2015-06-03 | 2019-08-12 | Bristol-Myers Squibb Company | 4-hidroksi-3-(heteroaril)piridin-2-ono apj agonistai, skirti panaudoti širdies ir kraujagyslių sutrikimų gydymui |
| WO2017016883A1 (en) | 2015-07-24 | 2017-02-02 | Basf Se | Process for preparation of cyclopentene compounds |
| US10660333B2 (en) | 2016-08-10 | 2020-05-26 | Bayer Cropscience Aktiengesellschaft | Substituted 2-heterocyclylimidazolylcarboxamides as pesticides |
| CN110234645A (zh) | 2017-01-25 | 2019-09-13 | 巴斯夫欧洲公司 | 制备卞型酰胺的方法 |
| WO2018177880A1 (en) | 2017-03-31 | 2018-10-04 | Syngenta Participations Ag | Fungicidal compositions |
| CA3055680A1 (en) | 2017-03-31 | 2018-10-04 | Syngenta Participations Ag | Fungicidal compositions |
| BR112019020735B1 (pt) | 2017-04-05 | 2023-12-05 | Syngenta Participations Ag | Compostos derivados de oxadiazol microbiocidas e seu uso, composição agroquímica e método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos |
| BR112019021019B1 (pt) | 2017-04-05 | 2023-12-05 | Syngenta Participations Ag | Compostos derivados de oxadiazol microbiocidas, composição agrícola, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos e uso de um composto derivado de oxadiazol |
| BR112019020739B1 (pt) | 2017-04-05 | 2023-12-19 | Syngenta Participations Ag | Compostos derivados de oxadiazol microbiocidas e seu uso, composição agroquímica, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos |
| BR112019020756B1 (pt) | 2017-04-05 | 2023-11-28 | Syngenta Participations Ag | Compostos derivados de oxadiazol microbicidas, composição agroquímica compreendendo os mesmos, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos e uso desses compostos |
| BR112019020819B1 (pt) | 2017-04-05 | 2023-12-05 | Syngenta Participations Ag | Composto de fórmula (i), composição agroquímica, método para controlar ou prevenir a infestação de plantas úteis por micro-organismos fitopatogênicos e uso de um composto de fórmula (i) |
| BR112019020734B1 (pt) | 2017-04-05 | 2023-12-05 | Syngenta Participations Ag | Compostos derivados de oxadiazol, composição agroquímica, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos e uso dos referidos compostos |
| MX2019012813A (es) * | 2017-04-26 | 2020-01-14 | Basf Se | Derivados de succinimida sustituida como plaguicidas. |
| WO2019243263A1 (en) * | 2018-06-19 | 2019-12-26 | Syngenta Participations Ag | Insecticidal compounds |
| CN112351981A (zh) | 2018-06-29 | 2021-02-09 | 先正达农作物保护股份公司 | 杀微生物的噁二唑衍生物 |
| US12030875B2 (en) | 2018-09-07 | 2024-07-09 | PIC Therapeutics, Inc. | EIF4E inhibitors and uses thereof |
| EP3856715A1 (en) * | 2018-09-26 | 2021-08-04 | Syngenta Participations Ag | Insecticidal compounds |
| PE20220171A1 (es) * | 2019-04-05 | 2022-01-28 | Syngenta Crop Protection Ag | Compuestos de diazina-amida activos como pesticidas |
| US20220169629A1 (en) * | 2019-04-11 | 2022-06-02 | Syngenta Crop Protection Ag | Pesticidally active diazine-amide compounds |
| AU2020408351A1 (en) * | 2019-12-18 | 2022-08-11 | Elanco Tiergesundheit Ag | Isoxazoline derivatives as pesticides |
| IL296139A (en) | 2020-03-03 | 2022-11-01 | Pic Therapeutics Inc | Eif4e inhibitors and uses thereof |
| US12108762B2 (en) * | 2020-09-08 | 2024-10-08 | Santanu Maitra | Methods of controlling crop pests using aromatic amide insect repellents, methods of making aromatic amide insect repellents, and novel aromatic amide insect repellents |
| WO2022239798A1 (ja) * | 2021-05-14 | 2022-11-17 | 日本曹達株式会社 | （ヘテロ）アリールアミド化合物および有害生物防除剤 |
| CN113563322B (zh) * | 2021-07-26 | 2023-07-07 | 海利尔药业集团股份有限公司 | 一种取代的苯甲酰胺类异噁唑啉衍生物或其作为农药可接受的盐、组合物及其用途 |
| CN115710195B (zh) * | 2021-08-22 | 2025-02-14 | 华东理工大学 | 具有杀线虫活性的三氟烯烃类化合物及其制备方法和用途 |
| AU2022334296A1 (en) | 2021-08-25 | 2024-03-07 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| WO2023028238A1 (en) | 2021-08-25 | 2023-03-02 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| CN113582987B (zh) * | 2021-09-02 | 2023-06-30 | 海利尔药业集团股份有限公司 | 一种取代的苯甲酰胺异噁唑啉衍生物或其作为农药可接受的盐、组合物及其用途 |
| CN114380762A (zh) * | 2022-01-23 | 2022-04-22 | 贵州大学 | 异恶唑啉酰肼衍生物及其制备方法和用途 |
| CN114933597B (zh) * | 2022-04-28 | 2023-04-07 | 武汉工程大学 | 一种3-羟基异噻唑啉衍生物、制备方法和应用 |
Family Cites Families (113)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3917698A (en) | 1972-05-05 | 1975-11-04 | Hercules Inc | Polyfunctional quaternary amidoximidinium salts |
| BR8404834A (pt) | 1983-09-26 | 1985-08-13 | Agrigenetics Res Ass | Metodo para modificar geneticamente uma celula vegetal |
| BR8600161A (pt) | 1985-01-18 | 1986-09-23 | Plant Genetic Systems Nv | Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio |
| DE3765449D1 (de) | 1986-03-11 | 1990-11-15 | Plant Genetic Systems Nv | Durch gentechnologie erhaltene und gegen glutaminsynthetase-inhibitoren resistente pflanzenzellen. |
| US5013659A (en) | 1987-07-27 | 1991-05-07 | E. I. Du Pont De Nemours And Company | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
| IL83348A (en) | 1986-08-26 | 1995-12-08 | Du Pont | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
| EP0330678B1 (en) | 1987-01-05 | 1990-10-24 | E.I. Du Pont De Nemours And Company | Insecticidal pyrazolines |
| NZ231804A (en) | 1988-12-19 | 1993-03-26 | Ciba Geigy Ag | Insecticidal toxin from leiurus quinquestriatus hebraeus |
| ATE241699T1 (de) | 1989-03-24 | 2003-06-15 | Syngenta Participations Ag | Krankheitsresistente transgene pflanze |
| DE69018772T2 (de) | 1989-11-07 | 1996-03-14 | Pioneer Hi Bred Int | Larven abtötende Lektine und darauf beruhende Pflanzenresistenz gegen Insekten. |
| EP0472722B1 (en) | 1990-03-16 | 2003-05-21 | Calgene LLC | Dnas encoding plant desaturases and their uses |
| RU2148081C1 (ru) | 1990-06-18 | 2000-04-27 | Монсанто Компани | Способ получения генетически трансформированных растений с повышенным содержанием крахмала и рекомбинантная двухцепочечная днк-молекула |
| DE69132939T2 (de) | 1990-06-25 | 2002-11-14 | Monsanto Technology Llc | Glyphosattolerante pflanzen |
| SE467358B (sv) | 1990-12-21 | 1992-07-06 | Amylogene Hb | Genteknisk foeraendring av potatis foer bildning av staerkelse av amylopektintyp |
| DE4104782B4 (de) | 1991-02-13 | 2006-05-11 | Bayer Cropscience Gmbh | Neue Plasmide, enthaltend DNA-Sequenzen, die Veränderungen der Karbohydratkonzentration und Karbohydratzusammensetzung in Pflanzen hervorrufen, sowie Pflanzen und Pflanzenzellen enthaltend dieses Plasmide |
| UA48104C2 (uk) | 1991-10-04 | 2002-08-15 | Новартіс Аг | Фрагмент днк, який містить послідовність,що кодує інсектицидний протеїн, оптимізовану для кукурудзи,фрагмент днк, який забезпечує направлену бажану для серцевини стебла експресію зв'язаного з нею структурного гена в рослині, фрагмент днк, який забезпечує специфічну для пилку експресію зв`язаного з нею структурного гена в рослині, рекомбінантна молекула днк, спосіб одержання оптимізованої для кукурудзи кодуючої послідовності інсектицидного протеїну, спосіб захисту рослин кукурудзи щонайменше від однієї комахи-шкідника |
| US5215568A (en) | 1991-10-31 | 1993-06-01 | American Cyanamid Company | Oxime derivatives of formylpyridyl imidazolinones, the herbicidal use and methods for the preparation thereof |
| US5530195A (en) | 1994-06-10 | 1996-06-25 | Ciba-Geigy Corporation | Bacillus thuringiensis gene encoding a toxin active against insects |
| JPH08217754A (ja) | 1995-02-15 | 1996-08-27 | Nippon Soda Co Ltd | イミダゾール化合物、殺虫・殺ダニ剤及び農園芸用殺菌剤 |
| IL117513A0 (en) | 1995-04-18 | 1996-07-23 | Du Pont | Oxazoline and thiazoline compounds and their use as arthropodicides |
| CA2240946C (en) | 1995-12-21 | 2002-09-10 | The Dupont Merck Pharmaceutical Company | Isoxazoline, isothiazoline and pyrazoline factor xa inhibitors |
| US6313344B1 (en) | 1998-05-27 | 2001-11-06 | Bayer Aktiengesellschaft | Organic compounds |
| AUPP873799A0 (en) | 1999-02-17 | 1999-03-11 | Fujisawa Pharmaceutical Co., Ltd. | Pyridine compounds |
| FR2792441B1 (fr) | 1999-04-14 | 2002-07-26 | Iodp | Systeme d'imagerie medicale |
| UA75051C2 (en) | 1999-09-03 | 2006-03-15 | Syngenta Participations Ag | Tetrahydropiridines as pesticides, a composition, a method for the preparation thereof and a method of controlling pests |
| CN100353846C (zh) | 2000-08-25 | 2007-12-12 | 辛根塔参与股份公司 | 新的来自苏云金芽孢杆菌杀虫晶体蛋白的杀虫毒素 |
| EP1365648A1 (en) | 2001-01-31 | 2003-12-03 | Bayer CropScience GmbH | Method of safening crops using isoxazoline carboxylates |
| JP2004521130A (ja) | 2001-02-05 | 2004-07-15 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | Ｎ−置換テトラヒドロピリヂン及びそれらの農薬としての使用 |
| US7230167B2 (en) | 2001-08-31 | 2007-06-12 | Syngenta Participations Ag | Modified Cry3A toxins and nucleic acid sequences coding therefor |
| DE10144872A1 (de) | 2001-09-12 | 2003-03-27 | Bayer Cropscience Gmbh | Azetidinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| WO2003052073A2 (en) | 2001-12-17 | 2003-06-26 | Syngenta Participations Ag | Novel corn event |
| JP2003277362A (ja) | 2002-01-21 | 2003-10-02 | Nippon Nohyaku Co Ltd | ピラゾールカルボキサミド類、その中間体およびこれを有効成分とする有害生物防除剤 |
| JP2005517029A (ja) | 2002-02-11 | 2005-06-09 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | （１−ベンジル−ピペリジン−４−イル）−ジフェニル−メタノールの誘導体と、その誘導体を利用した殺虫剤 |
| US6897240B2 (en) | 2002-05-08 | 2005-05-24 | The Regents Of The University Of California | Thio semicarbazone and semicarbazone inhibitors of cysteine proteases and methods of their use |
| EP1538138A4 (en) | 2002-08-26 | 2007-07-25 | Nissan Chemical Ind Ltd | SUBSTITUTED BENZANILIDE COMPOUND AND PROTECTIVE AGENTS |
| CN100384421C (zh) | 2002-12-18 | 2008-04-30 | 拜尔农科股份公司 | N-(取代的芳基甲基)-4-(二取代的甲基)哌啶和吡啶 |
| WO2004056735A1 (en) | 2002-12-23 | 2004-07-08 | Syngenta Participations Ag | 2,6-dihalo-4-(3,3-dichloro-allyloxy)-benzylalcohole derivatives having insecticidal and acaricidal properties |
| US20060167383A1 (en) | 2003-04-01 | 2006-07-27 | Kieturakis Maciej J | Screening methods and kits for gastrointestinal diseases |
| DE102004010086A1 (de) | 2003-05-06 | 2004-09-16 | Syngenta Participations Ag | Substiuierte Piperidinderivate |
| MXPA06003860A (es) | 2003-10-10 | 2006-07-03 | Fmc Corp | Azaciclos n-sustituidos. |
| US20080279917A1 (en) | 2003-11-25 | 2008-11-13 | Walzer Peter D | Bisbenzamidines for the Treatment of Pneumonia |
| BRPI0506477A (pt) | 2004-01-09 | 2007-02-06 | Cadila Healthcare Ltd | compostos farmaceuticamente úteis e inovadores |
| BRPI0508140B1 (pt) | 2004-03-05 | 2015-03-17 | Nissan Chemical Ind Ltd | Composto benzamida substituída por isoxazolina da fórmula (1); da fórmula (2) substituído por 3,5-bis (aril substituído); da fórmula (4) substituída por alquinibenzeno ou um sal do mesmo; "pesticida, agroquímico, inseticida, parasiticida contendo como ingrediente ativo um ou mais composto benzamida substituída por isoxazolina e sal do mesmo" |
| PE20060115A1 (es) | 2004-07-23 | 2006-03-23 | Basf Ag | 2-(piridin-2-il)-pirimidinas como agentes fungicidas |
| BRPI0514051B1 (pt) | 2004-08-04 | 2014-07-22 | Nippon Kayaku Co. , Ltd. | Composto derivado de quinolina que compreende o mesmo como ingrediente ativo, inseticida, método e uso destes no controle de pragas de insetos na agricultura e horticultura |
| CN101039922B (zh) | 2004-10-20 | 2011-04-13 | 组合化学工业株式会社 | 3-三唑基苯基硫醚衍生物及含其作为有效成分的杀虫·杀螨·杀线虫剂 |
| BRPI0519017A2 (pt) | 2004-12-13 | 2008-12-23 | Bayer Cropscience Ag | derivados de bis(fenil substituÍdo)-1-{[4-(heterociclil saturado su-bstituÍdo)fenilmetil]-(4-piperidil)}metano inseticidas |
| DE102005008021A1 (de) | 2005-02-22 | 2006-08-24 | Bayer Cropscience Ag | Spiroketal-substituierte cyclische Ketoenole |
| TWI388282B (zh) | 2005-06-01 | 2013-03-11 | Meiji Seika Pharma Co Ltd | 害蟲控制劑 |
| AU2006202083A1 (en) | 2005-06-03 | 2006-12-21 | Reto Brun | Linear dicationic terphenyls and their aza analogues as antiparasitic agents |
| JP5051340B2 (ja) | 2005-06-06 | 2012-10-17 | 日産化学工業株式会社 | 置換イソキサゾリン化合物及び有害生物防除剤 |
| WO2006135763A2 (en) | 2005-06-09 | 2006-12-21 | The Johns Hopkins University | Inhibitors of dna repair enzymes and methods of use thereof |
| JP4479917B2 (ja) | 2005-09-02 | 2010-06-09 | 日産化学工業株式会社 | イソキサゾリン置換ベンズアミド化合物及び有害生物防除剤 |
| ES2443690T3 (es) | 2005-09-02 | 2014-02-20 | Nissan Chemical Industries, Ltd. | Compuesto de benzamida sustituido con isoxazolina y agente controlador de organismos dañinos |
| CN100556905C (zh) | 2005-09-08 | 2009-11-04 | 国家南方农药创制中心江苏基地 | 吡唑酰胺类化合物及其中间体和以该类化合物为活性成分的有害生物防治剂 |
| JP2007106756A (ja) | 2005-09-14 | 2007-04-26 | Nissan Chem Ind Ltd | 置換イソキサゾリン化合物及び有害生物防除剤 |
| AU2006300182B2 (en) | 2005-10-14 | 2012-01-19 | Sumitomo Chemical Company, Limited | Hydrazide compound and pesticidal use of the same |
| AU2006326449A1 (en) | 2005-12-14 | 2007-06-21 | E. I. Du Pont De Nemours And Company | Isoxazolines for controlling invertebrate pests |
| TW200803740A (en) | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
| CN101346336B (zh) | 2005-12-26 | 2013-02-27 | 日产化学工业株式会社 | 1,3-二(取代苯基)-3-取代-2-丙烯-1-酮化合物和其盐 |
| TWI412322B (zh) | 2005-12-30 | 2013-10-21 | Du Pont | 控制無脊椎害蟲之異唑啉 |
| JP5113531B2 (ja) | 2006-01-16 | 2013-01-09 | 三井化学アグロ株式会社 | （３−硫黄原子置換フェニル）ピラゾール誘導体 |
| JPWO2007094313A1 (ja) | 2006-02-13 | 2009-07-09 | 日産化学工業株式会社 | ２−（置換フェニル）−３，３，３−トリフルオロプロペン化合物の製造方法 |
| EP1987002A1 (en) | 2006-02-14 | 2008-11-05 | Basf Se | Pyridin-4 -ylmethylamides for combating pests |
| DE102006015197A1 (de) | 2006-03-06 | 2007-09-13 | Bayer Cropscience Ag | Wirkstoffkombination mit insektiziden Eigenschaften |
| DE602007006288D1 (de) | 2006-03-10 | 2010-06-17 | Nissan Chemical Ind Ltd | Substituierte isoxazolin-verbindung und schädlingsbekämpfungsmittel |
| DE102006015467A1 (de) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Substituierte Enaminocarbonylverbindungen |
| WO2007123855A2 (en) * | 2006-04-20 | 2007-11-01 | E. I. Du Pont De Nemours And Company | Pyrazolines for controlling invertebrate pests |
| WO2007125984A1 (ja) | 2006-04-28 | 2007-11-08 | Nihon Nohyaku Co., Ltd. | イソキサゾリン誘導体及び有害生物防除剤並びにその使用方法 |
| TWI381811B (zh) | 2006-06-23 | 2013-01-11 | Dow Agrosciences Llc | 用以防治可抵抗一般殺蟲劑之昆蟲的方法 |
| GB0614691D0 (en) | 2006-07-24 | 2006-08-30 | Syngenta Participations Ag | Insecticidal compounds |
| JP2008044880A (ja) | 2006-08-15 | 2008-02-28 | Bayer Cropscience Ag | 殺虫性イソオキサゾリン類 |
| EP2057150A1 (en) | 2006-08-22 | 2009-05-13 | Basf Se | Thiophene-sulfonic acid picolyl amides |
| DE102006057036A1 (de) | 2006-12-04 | 2008-06-05 | Bayer Cropscience Ag | Biphenylsubstituierte spirocyclische Ketoenole |
| US20080139534A1 (en) | 2006-12-07 | 2008-06-12 | Xavier University Of Louisiana | Bisbenzamidines and bisbenzamidoximes for the treatment of human African trypanosomiasis |
| JP2008239611A (ja) | 2007-02-27 | 2008-10-09 | Nissan Chem Ind Ltd | イソキサゾリン置換ベンズアミド化合物及び有害生物防除剤 |
| EP2151437A4 (en) | 2007-03-07 | 2012-05-02 | Nissan Chemical Ind Ltd | ISOXAZOLINE SUBSTITUTED BENZAMIDE COMPOUND AND PEST CONTROL AGENT |
| JP5256753B2 (ja) | 2007-03-29 | 2013-08-07 | 住友化学株式会社 | イソオキサゾリン化合物とその有害生物防除用途 |
| JP2008260691A (ja) | 2007-04-10 | 2008-10-30 | Bayer Cropscience Ag | 殺虫性アリールイソオキサゾリン誘導体 |
| US8372867B2 (en) | 2007-04-10 | 2013-02-12 | Bayer Cropscience Ag | Insecticidal aryl isoxazoline derivatives |
| US20080262057A1 (en) | 2007-04-20 | 2008-10-23 | Dow Agrosciences Llc | Diarylisoxazolines |
| EP2155701B1 (en) | 2007-06-13 | 2013-12-11 | E. I. Du Pont de Nemours and Company | Isoxazoline insecticides |
| TWI430995B (zh) | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
| EP2957284B1 (en) | 2007-06-27 | 2018-01-17 | E. I. du Pont de Nemours and Company | Animal pest control method |
| WO2009001942A1 (ja) | 2007-06-27 | 2008-12-31 | Nissan Chemical Industries, Ltd. | ３－ヒドロキシプロパン－１－オン化合物、２－プロペン－１－オン化合物およびイソキサゾリン化合物の製造方法 |
| US8053452B2 (en) | 2007-06-29 | 2011-11-08 | Nissan Chemical Industries, Ltd. | Substituted isoxazoline or enone oxime compound, and pest control agent |
| CA2700598C (en) | 2007-08-10 | 2012-11-20 | Nippon Soda Co., Ltd. | Nitrogen-containing heterocyclic compound and pest control agent |
| TWI649303B (zh) | 2007-08-17 | 2019-02-01 | 杜邦股份有限公司 | 製備４-乙醯基-ｎ-〔２-側氧基-２-〔（２，２，２-三氟乙基）胺基〕乙基〕-１-萘甲醯胺之化合物及方法 |
| JP5365806B2 (ja) | 2007-09-10 | 2013-12-11 | 日産化学工業株式会社 | 置換イソキサゾリン化合物及び有害生物防除剤 |
| AU2008308907B2 (en) | 2007-10-03 | 2014-08-14 | Corteva Agriscience Llc | Naphthalene isoxazoline compounds for control of invertebrate pests |
| JP2009108046A (ja) | 2007-10-10 | 2009-05-21 | Nissan Chem Ind Ltd | 殺虫、殺ダニ、殺線虫、殺軟体動物、殺菌又は殺バクテリア組成物及び病害虫の防除方法 |
| WO2009051956A2 (en) | 2007-10-16 | 2009-04-23 | E. I. Du Pont De Nemours And Company | Pyrazole-substituted isoxazoline insecticides |
| GB0720232D0 (en) | 2007-10-16 | 2007-11-28 | Syngenta Participations Ag | Insecticidal compounds |
| NZ585883A (en) | 2007-12-19 | 2011-11-25 | Syngenta Participations Ag | Oxazoline derivatives as insecticidal compounds |
| TWI411395B (zh) | 2007-12-24 | 2013-10-11 | Syngenta Participations Ag | 殺蟲化合物 |
| JP2009286773A (ja) | 2008-03-14 | 2009-12-10 | Bayer Cropscience Ag | 殺虫性縮環式アリール類 |
| TW201002208A (en) | 2008-04-07 | 2010-01-16 | Bayer Cropscience Ag | Combinations of biological control agents and insecticides or fungicides |
| TWI583664B (zh) | 2008-04-09 | 2017-05-21 | 杜邦股份有限公司 | 羰基化合物及其製備方法 |
| BRPI0915818A2 (pt) | 2008-07-09 | 2015-08-04 | Basf Se | Mistura pesticida, composição pesticida, método para controlar fungos nocivos fitopatogênicos, para proteger plantas de fungos nocivos fitopatogênicos, para controlar insetos, aracnídeos ou nematódeos, para proteger plantas do ataque ou infestação por insetos, acarídeos ou nematódeos, e para a proteção de semente, semente, e, uso de uma mistura. |
| ES2635120T5 (es) | 2008-07-09 | 2024-06-03 | Basf Se | Mezclas activas de pesticidas que comprenden compuestos I de isoxazolina |
| JP5344862B2 (ja) | 2008-07-23 | 2013-11-20 | 日本エンバイロケミカルズ株式会社 | 工業用防腐防かび剤 |
| CN102131804B (zh) | 2008-08-22 | 2014-12-03 | 先正达参股股份有限公司 | 杀虫化合物 |
| MX2011001851A (es) | 2008-08-22 | 2011-03-21 | Syngenta Participations Ag | Compuestos insecticidas. |
| JP5715065B2 (ja) * | 2008-12-23 | 2015-05-07 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 有害動物を駆除するための置換アミジン化合物 |
| EA020318B1 (ru) * | 2008-12-23 | 2014-10-30 | Басф Се | Иминные соединения для борьбы с беспозвоночными вредителями |
| JP5747440B2 (ja) | 2009-02-06 | 2015-07-15 | 住友化学株式会社 | ヒドラジド化合物及びその有害生物防除用途 |
| BRPI1006543A2 (pt) | 2009-04-01 | 2015-08-25 | Basf Se | "compostos de isoxazolina, composição agrícola, composição veterinária, uso de composto, método para o controle de pragas invertebradas, material de propagação de plantas e método para o tratamento, controle, prevenção ou proteção de animais contra infestação ou infecção por parasitas" |
| JP5335588B2 (ja) | 2009-07-15 | 2013-11-06 | フジ日本精糖株式会社 | 切り花用鮮度保持剤 |
| TWI487486B (zh) * | 2009-12-01 | 2015-06-11 | Syngenta Participations Ag | 以異唑啉衍生物為主之殺蟲化合物 |
| WO2011073444A2 (en) | 2009-12-18 | 2011-06-23 | Basf Se | Azoline compounds for combating invertebrate pests |
| US8999889B2 (en) | 2010-02-01 | 2015-04-07 | Basf Se | Substituted ketonic isoxazoline compounds and derivatives for combating animal pests |
| JP2011212522A (ja) | 2010-03-31 | 2011-10-27 | Aquas Corp | 水系中のイソチアゾリン系化合物の分解抑制方法、及び、水系の微生物制御方法 |
| CN103842358A (zh) * | 2011-09-13 | 2014-06-04 | 先正达参股股份有限公司 | 作为杀虫化合物的异噻唑啉衍生物 |
-
2012
- 2012-12-21 EP EP12810287.8A patent/EP2794601B1/en not_active Not-in-force
- 2012-12-21 MX MX2014006973A patent/MX2014006973A/es unknown
- 2012-12-21 CN CN201280070554.8A patent/CN104169278B/zh not_active Expired - Fee Related
- 2012-12-21 KR KR1020147020594A patent/KR20140115329A/ko not_active Ceased
- 2012-12-21 US US14/366,161 patent/US9732051B2/en not_active Expired - Fee Related
- 2012-12-21 ES ES12810287T patent/ES2727479T3/es active Active
- 2012-12-21 JP JP2014548048A patent/JP6415983B2/ja not_active Expired - Fee Related
- 2012-12-21 AU AU2012356947A patent/AU2012356947A1/en not_active Abandoned
- 2012-12-21 WO PCT/EP2012/076539 patent/WO2013092943A1/en not_active Ceased
- 2012-12-21 IN IN4376CHN2014 patent/IN2014CN04376A/en unknown
- 2012-12-21 CA CA2858766A patent/CA2858766A1/en not_active Abandoned
- 2012-12-21 BR BR112014015553-4A patent/BR112014015553B1/pt not_active IP Right Cessation
- 2012-12-26 AR ARP120104961A patent/AR090045A1/es unknown
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2014
- 2014-06-12 CR CR20140276A patent/CR20140276A/es unknown
- 2014-06-16 CO CO14130271A patent/CO6980665A2/es unknown
- 2014-06-23 IL IL233312A patent/IL233312A0/en unknown
- 2014-06-23 CL CL2014001688A patent/CL2014001688A1/es unknown
- 2014-07-21 ZA ZA2014/05336A patent/ZA201405336B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2794601B1 (en) | 2019-02-20 |
| CL2014001688A1 (es) | 2014-11-07 |
| CO6980665A2 (es) | 2014-06-27 |
| JP2015502967A (ja) | 2015-01-29 |
| IL233312A0 (en) | 2014-08-31 |
| KR20140115329A (ko) | 2014-09-30 |
| JP6415983B2 (ja) | 2018-10-31 |
| ZA201405336B (en) | 2017-11-29 |
| CN104169278B (zh) | 2017-10-24 |
| EP2794601A1 (en) | 2014-10-29 |
| US9732051B2 (en) | 2017-08-15 |
| BR112014015553A2 (pt) | 2017-06-13 |
| AR090045A1 (es) | 2014-10-15 |
| CA2858766A1 (en) | 2013-06-27 |
| CR20140276A (es) | 2014-07-23 |
| ES2727479T3 (es) | 2019-10-16 |
| IN2014CN04376A (enExample) | 2015-09-04 |
| WO2013092943A1 (en) | 2013-06-27 |
| BR112014015553B1 (pt) | 2020-02-27 |
| US20140364466A1 (en) | 2014-12-11 |
| CN104169278A (zh) | 2014-11-26 |
| MX2014006973A (es) | 2014-08-01 |
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