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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- 229910052700 potassium Inorganic materials 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
- 125000004290 pyrazolidin-3-yl group Chemical group [H]N1N([H])C([H])(*)C([H])([H])C1([H])[H] 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)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361838370P | 2013-06-24 | 2013-06-24 | |
| US201361838370P | 2013-06-24 | ||
| US201361896137P | 2013-10-28 | 2013-10-28 | |
| US201361896137P | 2013-10-28 | ||
| PCT/EP2014/063106 WO2014206911A1 (en) | 2013-06-24 | 2014-06-23 | Isothiazoline compounds for combating invertebrate pests |
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| ES2688893T3 true ES2688893T3 (es) | 2018-11-07 |
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| WO (1) | WO2014206911A1 (https=) |
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| US9744542B2 (en) | 2013-07-29 | 2017-08-29 | Apeel Technology, Inc. | Agricultural skin grafting |
| JP2018509463A (ja) | 2015-01-16 | 2018-04-05 | 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 | 抗寄生生物化合物 |
| EP3673738B1 (en) | 2015-05-20 | 2024-02-28 | Apeel Technology, Inc. | Plant extract compositions and methods of preparation thereof |
| CN108135188B (zh) | 2015-09-16 | 2022-08-05 | 阿比尔技术公司 | 用于分子涂层的前体化合物 |
| WO2017100636A1 (en) | 2015-12-10 | 2017-06-15 | Apeel Technology, Inc. | Plant extract compositions for forming protective coatings |
| WO2017132281A1 (en) | 2016-01-26 | 2017-08-03 | Apeel Technology, Inc. | Method for preparing and preserving sanitized products |
| WO2018094269A1 (en) | 2016-11-17 | 2018-05-24 | Apeel Technology, Inc. | Compositions formed from plant extracts and methods of preparation thereof |
| WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
| US10807992B2 (en) | 2017-11-16 | 2020-10-20 | Avista Pharma Solutions, Inc. | Single enantiomer antiparasitic compounds |
| 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 |
| MX2023004343A (es) | 2020-10-30 | 2023-05-08 | Apeel Tech Inc | Composiciones y metodos de preparacion de las mismas. |
| EP4398731A1 (en) | 2021-09-08 | 2024-07-17 | Apeel Technology, Inc. | Compounds and formulations for protective coatings |
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| CN101768129B (zh) * | 2004-03-05 | 2012-05-23 | 日产化学工业株式会社 | 异*唑啉取代苯甲酰胺化合物的制备中间体 |
| US8999889B2 (en) * | 2010-02-01 | 2015-04-07 | Basf Se | Substituted ketonic isoxazoline compounds and derivatives for combating animal pests |
| BR122018069466B1 (pt) * | 2011-09-13 | 2019-04-02 | Syngenta Participations Ag | Derivados isotiazolina como compostos inseticidas |
| CA2858766A1 (en) * | 2011-12-23 | 2013-06-27 | Basf Se | Isothiazoline compounds for combating invertebrate pests |
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| WO2014206911A1 (en) | 2014-12-31 |
| BR112015032346A2 (pt) | 2017-07-25 |
| MX2015018015A (es) | 2016-07-13 |
| MX368592B (es) | 2019-10-08 |
| JP2016527208A (ja) | 2016-09-08 |
| CA2916766C (en) | 2021-05-04 |
| EP3013819A1 (en) | 2016-05-04 |
| CN105473582A (zh) | 2016-04-06 |
| CA2916766A1 (en) | 2014-12-31 |
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