ES2688893T3 - Compuestos de isotiazolina para combatir plagas de invertebrados - Google Patents
Compuestos de isotiazolina para combatir plagas de invertebrados Download PDFInfo
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- ES2688893T3 ES2688893T3 ES14732176.4T ES14732176T ES2688893T3 ES 2688893 T3 ES2688893 T3 ES 2688893T3 ES 14732176 T ES14732176 T ES 14732176T ES 2688893 T3 ES2688893 T3 ES 2688893T3
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- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical class C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 241000607479 Yersinia pestis Species 0.000 title claims description 24
- -1 thiazolidin-3-yl Chemical group 0.000 claims abstract description 514
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 77
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 48
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 125000001424 substituent group Chemical group 0.000 claims abstract description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 38
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 38
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 34
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 33
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 28
- 150000002367 halogens Chemical class 0.000 claims abstract description 28
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims abstract description 24
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 22
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 21
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 20
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- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 17
- 125000000232 haloalkynyl group Chemical group 0.000 claims abstract description 17
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- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 9
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 8
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- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims abstract description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 7
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- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 7
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 7
- 125000004266 aziridin-1-yl group Chemical group [H]C1([H])N(*)C1([H])[H] 0.000 claims abstract description 6
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- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims abstract description 5
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract description 4
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims abstract description 4
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- 150000002431 hydrogen Chemical class 0.000 claims abstract 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 56
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- 125000000217 alkyl group Chemical group 0.000 claims description 39
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- 125000006416 CBr Chemical group BrC* 0.000 claims 2
- 150000002466 imines Chemical class 0.000 claims 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 39
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 23
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- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 19
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
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- 125000004414 alkyl thio group Chemical group 0.000 description 14
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- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 11
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- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 10
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- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 9
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- 125000005843 halogen group Chemical group 0.000 description 8
- 230000000749 insecticidal effect Effects 0.000 description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 7
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 7
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- 125000004429 atom Chemical group 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 7
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 6
- 125000001627 3 membered heterocyclic group Chemical group 0.000 description 6
- 125000001963 4 membered heterocyclic group Chemical group 0.000 description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- 244000061456 Solanum tuberosum Species 0.000 description 6
- 235000002595 Solanum tuberosum Nutrition 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
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- 108020004511 Recombinant DNA Proteins 0.000 description 5
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- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 5
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 5
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- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
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- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
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- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 3
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- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 description 1
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- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
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- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003001 serine protease inhibitor Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000037359 steroid metabolism Effects 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000004300 thiazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])SC1([H])* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004569 thiomorpholin-2-yl group Chemical group N1CC(SCC1)* 0.000 description 1
- 125000004570 thiomorpholin-3-yl group Chemical group N1C(CSCC1)* 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 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
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
Landscapes
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361838370P | 2013-06-24 | 2013-06-24 | |
| US201361838370P | 2013-06-24 | ||
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| PCT/EP2014/063106 WO2014206911A1 (en) | 2013-06-24 | 2014-06-23 | Isothiazoline compounds for combating invertebrate pests |
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| US9744542B2 (en) | 2013-07-29 | 2017-08-29 | Apeel Technology, Inc. | Agricultural skin grafting |
| GB2538028B (en) | 2015-01-16 | 2017-02-08 | Avista Pharma Solutions | Antiparasitic compounds |
| WO2016187581A1 (en) | 2015-05-20 | 2016-11-24 | Apeel Technology, Inc. | Plant extract compositions and methods of preparation thereof |
| WO2017048951A1 (en) | 2015-09-16 | 2017-03-23 | Apeel Technology, Inc. | Precursor compounds for molecular coatings |
| JP6549326B2 (ja) | 2015-12-10 | 2019-07-24 | アピール テクノロジー，インコーポレイテッド | 保護コーティングを形成するための植物抽出物組成物 |
| CN109068627B (zh) | 2016-01-26 | 2022-03-18 | 阿比尔技术公司 | 用于制备和保存消毒产品的方法 |
| EP3541192B1 (en) | 2016-11-17 | 2025-06-25 | Apeel Technology, Inc. | Methods of preparing fatty acid esters from crosslinked polyesters |
| WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
| JP2021503465A (ja) | 2017-11-16 | 2021-02-12 | アビスタ ファーマ ソリューションズ，インコーポレーテッド | 単一エナンチオマーの抗寄生生物化合物 |
| TWI812673B (zh) | 2018-02-12 | 2023-08-21 | 美商富曼西公司 | 用於防治無脊椎害蟲之萘異噁唑啉化合物 |
| US12245605B2 (en) | 2018-09-05 | 2025-03-11 | Apeel Technology, Inc. | Compounds and formulations for protective coatings |
| US11641865B2 (en) | 2020-03-04 | 2023-05-09 | Apeel Technology, Inc. | Compounds and formulations for protective coatings |
| US11827591B2 (en) | 2020-10-30 | 2023-11-28 | Apeel Technology, Inc. | Compositions and methods of preparation thereof |
| CN118159138A (zh) | 2021-09-08 | 2024-06-07 | 阿比尔技术公司 | 用于保护性涂层的化合物和制剂 |
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| AU2005219788B2 (en) * | 2004-03-05 | 2010-06-03 | Nissan Chemical Corporation | Isoxazoline-substituted benzamide compound and noxious organism control agent |
| JP2013518084A (ja) * | 2010-02-01 | 2013-05-20 | ビーエーエスエフ ソシエタス・ヨーロピア | 有害動物を駆除するための置換されたケトン性イソオキサゾリン化合物および誘導体 |
| EP2755969B1 (en) * | 2011-09-13 | 2017-01-18 | Syngenta Participations AG | Isothiazoline derivatives as insecticidal compounds |
| WO2013092943A1 (en) * | 2011-12-23 | 2013-06-27 | Basf Se | Isothiazoline compounds for combating invertebrate pests |
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| EP3013819A1 (en) | 2016-05-04 |
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| MX2015018015A (es) | 2016-07-13 |
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| BR112015032346A2 (pt) | 2017-07-25 |
| MX368592B (es) | 2019-10-08 |
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