AR094723A1 - Compuestos de malononitrilo para controlar plagas de animales - Google Patents
Compuestos de malononitrilo para controlar plagas de animalesInfo
- Publication number
- AR094723A1 AR094723A1 ARP130103877A ARP130103877A AR094723A1 AR 094723 A1 AR094723 A1 AR 094723A1 AR P130103877 A ARP130103877 A AR P130103877A AR P130103877 A ARP130103877 A AR P130103877A AR 094723 A1 AR094723 A1 AR 094723A1
- Authority
- AR
- Argentina
- Prior art keywords
- substituted
- alkyl
- cycloalkyl
- alkenyl
- carbon atoms
- Prior art date
Links
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical class N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 15
- 229910052736 halogen Inorganic materials 0.000 abstract 12
- 150000002367 halogens Chemical group 0.000 abstract 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 11
- 229910052799 carbon Inorganic materials 0.000 abstract 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 8
- 125000001424 substituent group Chemical group 0.000 abstract 8
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 229920006395 saturated elastomer Polymers 0.000 abstract 6
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 5
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 229910052717 sulfur Inorganic materials 0.000 abstract 4
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 abstract 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 3
- -1 cyano, hydroxy Chemical group 0.000 abstract 3
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 3
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 3
- 125000005347 halocycloalkyl group Chemical group 0.000 abstract 3
- 125000005842 heteroatom Chemical group 0.000 abstract 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 125000002837 carbocyclic group Chemical group 0.000 abstract 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 abstract 1
- 241000607479 Yersinia pestis Species 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000004970 halomethyl group Chemical group 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 abstract 1
Classifications
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
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- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
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- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
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- 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
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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- 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
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- 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
- A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/35—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/45—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms doubly-bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/083—Syntheses without formation of a Si-C bond
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
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- C07C2601/14—The ring being saturated
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- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
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- Pest Control & Pesticides (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
Reivindicación 1: El uso de un compuesto de la fórmula (1) o una de sus sales para combatir plagas animales, en donde Y es fenilo no sustituido o sustituido con 1, 2, 3, 4 ó 5 sustituyentes R⁵; o naftilo no sustituido o sustituido con 1, 2, 3, 4, 5, 6 ó 7 sustituyentes R⁵; Q es fenilo no sustituido o sustituido con 1, 2, 3, 4 ó 5 sustituyentes R⁶; cicloalquilo C₃₋₈ no sustituido o sustituido con uno o varios sustituyentes R⁶; o cicloalquenilo C₃₋₈ no sustituido o sustituido con uno o varios sustituyentes R⁶; R¹ es hidrógeno, halógeno, ciano, hidroxi, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, cicloalquenilo C₃₋₈, alcoxi C₁₋₆, alquenil C₂₋₆-oxi, alquil C₁₋₆-tio, (alcoxi C₁₋₆)carbonilo, en donde los átomos de carbono de los radicales alifáticos o cicloalifáticos antes mencionados no están sustituidos o están sustituidos con 1, 2 ó 3 sustituyentes R⁷; R² es hidrógeno o halógeno; o R¹ y R² forman, junto con el átomo de carbono al que están unidos, un grupo metileno o un grupo ciclopropilo; R³ es hidrógeno, halógeno, ciano, hidroxi, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, cicloalquenilo C₃₋₈, alcoxi C₁₋₆, alquenil C₂₋₆-oxi, alquil C₁₋₆-tio, (alcoxi C₁₋₆)carbonilo, en donde los átomos de carbono de los radicales alifáticos o cicloalifáticos antes mencionados no están sustituidos o están sustituidos con 1, 2 ó 3 sustituyentes R⁷; R⁴ es hidrógeno o halógeno; o R³ y R⁴ forman, junto con el átomo de carbono al que están unidos, un grupo metileno o un grupo ciclopropilo; cada R⁵, R⁶ es, de modo independiente, halógeno, ciano, azido, nitro, -SCN, SF₅, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, en donde los átomos de carbono de los radicales alifáticos antes mencionados no están sustituidos o están sustituidos con uno o varios Rᵃ; cicloalquilo C₃₋₈ o cicloalquenilo C₃₋₈, en donde los átomos de carbono de los radicales cicloalifáticos antes mencionados no están sustituidos o están sustituidos con uno o varios Rᵇ; fenilo no sustituido o sustituido con hasta 5 Rᶜ; un anillo heterocíclico saturado, parcialmente insaturado o aromático de 3, 4, 5, 6 ó 7 miembros que contiene 1, 2 ó 3 heteroátomos o grupos heteroatómicos seleccionados de N, O, S, NO, SO, SO₂, en donde el anillo antes mencionado no está sustituido o está sustituido con hasta 5 Rᵈ; Si(Rᵉ)₃, ORᶠ, SRᶠ, OS(O)ˣRʰ, S(O)ˣRʰ, N(Rⁱ)₂, N(Rⁱ)C(=O)Rᵐ, OC(=O)Rᵐ, C(=O)Rᵐ, C(=O)ORᶠ, C(=NRⁱ)Rᵐ, C(S)Rᵐ; o dos R⁵ en dos átomos de carbono adyacentes presentes en un anillo fenilo son juntos un puente seleccionado de CH₂CH₂CH₂CH₂, N=CH-CH=CH, CH=N-CH=CH, N=CH-N=CH, N=CH-CH=N, OCH₂CH₂CH₂, OCH=CHCH₂, CH₂OCH₂CH₂, OCH₂CH₂O, OCH₂OCH₂, CH₂CH₂CH₂, CH=CHCH₂, CH₂CH₂O, CH=CHO, CH₂OCH₂, CH₂C(=O)O, C(=O)OCH₂, O(CH₂)O, SCH₂CH₂CH₂, SCH=CHCH₂, CH₂SCH₂CH₂, SCH₂CH₂S, SCH₂SCH₂, CH₂CH₂S, CH=CHS, CH₂SCH₂, CH₂C(=S)S, C(=S)SCH₂, S(CH₂)S, CH₂CH₂NRK, CH₂CH=N, CH=CHNRK, OCH=N, SCH=N y forman, junto con los átomos de carbono a los que están unidos dos R⁵, un anillo carbocíclico o heterocíclico parcialmente insaturado o aromático de 5 ó 6 miembros, en donde el anillo no está sustituido o está sustituido con 1 ó 2 sustituyentes seleccionados de =O, OH, CH₃, OCH₃, halógeno, halometilo y halometoxi; cada R⁷ es, de modo independiente, halógeno, ciano, hidroxi, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, cicloalquenilo C₃₋₈, alcoxi C₁₋₆, alquenil C₂₋₆-oxi, alquil C₁₋₆-tio, (alcoxi C₁₋₆)carbonilo, OSi(Rᵉ)₃, en donde los átomos de carbono de los radicales alifáticos o cicloalifáticos antes mencionados no están sustituidos, están parcial o completamente halogenados y/u oxigenados; cada Rᵃ es, de modo independiente, halógeno, ciano, azido, nitro, -SCN, SF₅, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆-tio, alquil C₁₋₆-sulfinilo, alquil C₁₋₆-sulfonilo, haloalquil C₁₋₆-tio, cicloalquilo C₃₋₈, halocicloalquilo C₃₋₈, alquenilo C₂₋₆, haloalquenilo C₂₋₆, alquinilo C₂₋₆, haloalquinilo C₂₋₆, alquil C₁₋₆-cicloalquilo C₃₋₈, Si(Rᵉ)₃, ORA, SRA, OSO₂RB, S(O)ˣRB, S(O)ˣN(RD)₂, N(RD)₂, C(=O)N(RD)₂, C(=S)N(RD)₂, C(=O)ORA, fenilo no sustituido o sustituido con hasta 5 RE; un anillo heterocíclico saturado, parcialmente insaturado o aromático de 3, 4, 5, 6 ó 7 miembros que contiene 1, 2 ó 3 heteroátomos o grupos heteroatómicos seleccionados de N, O, S, NO, SO, SO₂, en donde el anillo antes mencionado no está sustituido o está sustituido con hasta 5 RE, o dos Rᵃ presentes en un átomo de carbono son juntos =O, =C(RF)₂, =NRD, =NORA, =NNRD, o dos Rᵃ forman un anillo carbocíclico o heterocíclico saturado o parcialmente insaturado de 3, 4, 5, 6, 7 u 8 miembros junto con los átomos de carbono a los que dos Rᵃ están unidos; cada Rᵇ es, de modo independiente, halógeno, ciano, azido, nitro, -SCN, SF₅, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆-tio, alquil C₁₋₆-sulfinilo, alquil C₁₋₆-sulfonilo, haloalquil C₁₋₆-tio, cicloalquilo C₃₋₈, halocicloalquilo C₃₋₈, alquenilo C₂₋₆, haloalquenilo C₂₋₆, alquinilo C₂₋₆, haloalquinilo C₂₋₆, alquil C₁₋₆-cicloalquilo C₃₋₈, Si(RG)₃, ORH, SRH, OSO₂RJ, S(O)ˣRJ, -S(O)ˣN(RK)₂, N(RK)₂, C(=O)N(RK)₂, C(=S)N(RK)₂, C(=O)ORH, o dos Rᵇ presentes en un átomo de carbono son juntos =O, =C(RL)₂, =NRK, =NORH, =NNRK, o dos Rᵇ forman un anillo carbocíclico o heterocíclico saturado o parcialmente insaturado de 3, 4, 5, 6, 7 u 8 miembros junto con los átomos de carbono a los que dos Rᵇ están unidos; cada Rᶜ es, de modo independiente, halógeno, ciano, azido, nitro, -SCN, SF₅, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, en donde los átomos de carbono de los radicales alifáticos o cicloalifáticos antes mencionados no están sustituidos o están sustituidos con uno o varios RM; Si(RG)₃, ORH, SRH, OS(O)ˣRJ, S(O)ˣRJ, -S(O)ˣN(RK)₂, N(RK)₂, C(=O)RN, C(=O)ORH, C(=NRK)RN, C(=O)N(RK)₂, C(=S)N(RK)₂; cada Rᵈ es, de modo independiente, halógeno, ciano, azido, nitro, -SCN, SF₅, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, en donde los átomos de carbono de los radicales alifáticos o cicloalifáticos antes mencionados no están sustituidos o están sustituidos con uno o varios RM; Si(RG)₃, ORH, SRH, OS(O)ˣRJ, S(O)ˣRJ, S(O)ˣN(RK)₂, N(RK)₂, C(=O)RN, C(=O)ORH, C(=NRK)RN, C(=O)N(RK)₂, C(=S)N(RK)₂, o dos Rᵈ presentes en un átomo de un anillo heterocíclico saturado o parcialmente insaturado son juntos =O, =C(RL)₂, =NRK, =NORH o =NNRK; cada Rᵉ es, de modo independiente, halógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxialquilo C₁₋₆, alquenilo C₂₋₆, haloalquenilo C₂₋₆, alquinilo C₂₋₆, haloalquinilo C₂₋₆, cicloalquilo C₃₋₈, halocicloalquilo C₃₋₈, haloalcoxialquilo C₁₋₆, fenilo, un anillo heterocíclico saturado, parcialmente insaturado o aromático de 3, 4, 5, 6 ó 7 miembros que contiene 1, 2 ó 3 heteroátomos o grupos heteroatómicos seleccionados de N, O, S, NO, SO, SO₂; cada Rᶠ es, de modo independiente, hidrógeno, ciano, alquilo C₁₋₆, alquil C₁₋₆-sulfinilo, alquil C₁₋₆-sulfonilo, cicloalquilo C₃₋₈, alquenilo C₂₋₆, alquinilo C₂₋₆, en donde los átomos de carbono de los radicales alifáticos o cicloalifáticos antes mencionados no están sustituidos o están sustituidos con uno
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| EP (1) | EP2911509B1 (es) |
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| AU2015247463B2 (en) * | 2014-04-17 | 2018-03-29 | Basf, Se | Use of malononitrile compounds for protecting animals from parasites |
| CN109096146B (zh) * | 2018-09-03 | 2020-11-10 | 杭州中美华东制药有限公司 | 阿那曲唑关键中间体的合成方法 |
| 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 |
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| DE335994C (de) * | 1916-06-28 | 1921-04-22 | Chem Fab Von Heyden Aktien Ges | Verfahren zur Herstellung von Hydantoinen |
| US3558671A (en) * | 1967-08-30 | 1971-01-26 | Du Pont | Fluoro- and cyano-substituted 7,7,8,8-tetracyanoquinodimethans and intermediates thereto |
| GB9002830D0 (en) * | 1990-02-08 | 1990-04-04 | Secr Defence | L.c.cyanoalkenes & alkenes |
| JPH1029966A (ja) * | 1996-07-17 | 1998-02-03 | Mitsubishi Chem Corp | マロノニトリル誘導体およびこれを有効成分とする除草剤 |
| EP1140784A2 (en) * | 1998-12-22 | 2001-10-10 | Neurosearch A/S | Ion channel modulating agents |
| JP2003026510A (ja) * | 2001-05-09 | 2003-01-29 | Sumitomo Chem Co Ltd | マロノニトリル化合物およびその有害生物防除用途 |
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| DE60309874T2 (de) | 2002-07-17 | 2007-03-15 | Sumitomo Chemical Co., Ltd. | Malonsäuerenitril-verbindungen und ihre verwendung als pestizide |
| EP1916895A1 (en) | 2005-08-01 | 2008-05-07 | Basf Se | Dicyano alkanoic acid amides for combating animal pests |
| EP1912958A1 (en) * | 2005-08-05 | 2008-04-23 | Basf Se | Substituted malononitrile compounds for combating animal pests |
| AU2006328521A1 (en) * | 2005-12-22 | 2007-06-28 | Basf Se | Malononitrile compounds |
| CN101506150B (zh) * | 2006-06-22 | 2013-08-28 | 巴斯夫欧洲公司 | 丙二腈化合物 |
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| AU2013336754A1 (en) | 2015-05-14 |
| ZA201503573B (en) | 2017-08-30 |
| JP6647865B2 (ja) | 2020-02-14 |
| US20150282481A1 (en) | 2015-10-08 |
| ES2644339T3 (es) | 2017-11-28 |
| WO2014064093A1 (en) | 2014-05-01 |
| CA2888390A1 (en) | 2014-05-01 |
| MX2015005314A (es) | 2015-10-29 |
| JP2018158923A (ja) | 2018-10-11 |
| EP2911509B1 (en) | 2017-07-19 |
| BR112015009174A8 (pt) | 2019-09-10 |
| EP2911509A1 (en) | 2015-09-02 |
| AU2013336754B2 (en) | 2017-04-13 |
| NZ707308A (en) | 2018-09-28 |
| CN104869826B (zh) | 2017-08-29 |
| CN104869826A (zh) | 2015-08-26 |
| US10292388B2 (en) | 2019-05-21 |
| MX366818B (es) | 2019-07-25 |
| CA2888390C (en) | 2021-07-20 |
| JP2015533844A (ja) | 2015-11-26 |
| BR112015009174A2 (pt) | 2017-07-04 |
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