ES2514318T3 - Compuestos insecticidas - Google Patents

Compuestos insecticidas Download PDF

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Publication number
ES2514318T3
ES2514318T3 ES10724791.8T ES10724791T ES2514318T3 ES 2514318 T3 ES2514318 T3 ES 2514318T3 ES 10724791 T ES10724791 T ES 10724791T ES 2514318 T3 ES2514318 T3 ES 2514318T3
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pyrid
chloro
fluoro
dichloro
difluoro
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Jérôme Yves CASSAYRE
Thomas Pitterna
Camilla Corsi
Peter Maienfisch
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Syngenta Participations AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • 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
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings

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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)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Un compuesto de fórmula (I):**Fórmula** en la que A es CR2 o N; p es 0 ó 1; R1 es pirid-4-ilo opcionalmente sustituido con uno o dos sustituyentes seleccionados cada uno independientemente de halógeno, alquilo de C1-C3, haloalquilo de C1-C3, o alcoxi de C1-C3; R2 es hidrógeno, halógeno, haloalquilo de C1-C3 o haloalcoxi de C1-C3; R3 y R4 son independientemente hidrógeno, halógeno, ciano, alquilo de C1-C8, haloalquilo de C1-C8, alquenilo de C2- C8, haloalquenilo de C2-C8, cicloalquilo de C3-C8, halocicloalquilo de C3-C8, alcoxi de C1-C8, haloalcoxi de C1-C8, alquil C1-C8-tio o haloalquil C1-C8-tio; R5 es hidrógeno o halógeno; y R8 es hidrógeno, halógeno, ciano, alquilo de C1-C8, haloalquilo de C1-C8, cicloalquilo de C3-C8, alquenilo de C2-C8, haloalquenilo de C2-C8, alquinilo de C2-C8, alcoxi de C1-C8 o haloalcoxi de C1-C8; o sales del mismo.

Description

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17
Tabla A:
Compuestos de fórmula (Ia)
imagen16
Comp. nº
R1 R2 R3 R4 R5 R8 p. f. HPLC (RT) MS (ES+)
A1
2-cloro-pirid-4-ilo- H -CF3 H H Cl 202-203ºC 1,37 min 586/588
A2
2-cloro-pirid-4-ilo- H -CF3 H H F 89-90ºC 1,29 min 570/572
A3
2-cloro-5-fluoro-pirid-4-ilo- H -CF3 H H Cl 156-158ºC 1,38 min 604/606
A4
2,6-dicloro-pirid-4-ilo- H -CF3 H H Cl 169-170ºC 1,47 min 620/622
A5
2,5-dicloro-pirid-4-ilo- H -CF3 H H Cl 147-148ºC 1,43 min 620/622
A6
2-fluoro-pirid-4-ilo- H -CF3 H H Cl 199-200ºC 1,35 min 570/572
A7
2-cloro-pirid-4-ilo- H -CF3 H H H - 1,27 min 552/554
A8
2-cloro-pirid-4-ilo- H -CF3 F H Cl 200-205ºC 1,43 min 604/606
A9
2-cloro-pirid-4-ilo- F F H H Cl 100-105ºC 1,30 min 554/556
A10
2-cloro-pirid-4-ilo- H F H H Cl 176ºC 1,27 min 536/538
A11
2-cloro-pirid-4-ilo- F -CF3 H H Cl 105-110ºC 1,41 min 604/606
A12
2-cloro-pirid-4-ilo- H H -OCF3 H Cl 211-212ºC 1,39 min 602/604
A13
2-metoxi-pirid-4-ilo- H CF3 H H Cl 199-200ºC 1,42 min 582/584
A14
2-metoxi-pirid-4-ilo- H CF3 F H Cl 205-208ºC 1,41 min 600/602
A15
2-fluoro-pirid-4-ilo- H CF3 F H Cl 173-176ºC 1,24 min 588/590
A16
2-cloro-pirid-4-ilo- H CF3 H H CF3 206-206ºC 1,42 min 620/622
Comp. nº
R1 R2 R3 R4 R5 R8 p. f. HPLC (RT) MS (ES+)
A17
2-cloro-pirid-4-ilo- H CF3 H H ciclo-propilo - 1,32 min 592/594
A18
2-cloro-pirid-4-ilo- H CF3 H H Br 199-199ºC 1,36 min 630/632
A19
2-cloro-pirid-4-ilo- CF3 H H H Cl 168-168ºC 1,33 min 586/588
A20
2-cloro-pirid-4-ilo- H CF3 H H CN 200-200ºC 1,29 min 577/579
A21
2-cloro-pirid-4-ilo- H CF3 H H etinilo 188-188ºC 1,31 min 576/578
A22
2-cloro-pirid-4-ilo- H CF3 H H CH3 - 1,26 min 566/568
A23
2,6-dicloro-pirid-4-ilo- H CF3 F H Cl 198-202ºC 1,48 min 638/640
A24
2,5-dicloro-pirid-4-ilo- H CF3 F H Cl 178-181ºC 1,44 min 638/640
A25
2-cloro-5-fluoro-pirid-4-ilo- H CF3 F H Cl 192-194ºC 1,44 min 622/624
A26
2-cloro-pirid-4-ilo- H H CF3 H Cl - 1,36 min 586/588
A27
2-cloro-pirid-4-ilo- H O-CF3 H H Cl - 1,39 min 602/604
A28
2-cloro-pirid-4-ilo- H F F F Cl 205-207ºC 1,34 min 572/574
A29
2,5-difluoro-pirid-4-ilo- H CF3 H H Cl 182-183ºC 1,33 min 588/590
A30
2,6-dicloro-pirid-4-ilo- F Cl H H Cl 121-125ºC 1,42 min 604/606
A31
2-fluoro-pirid-4-ilo- F Cl H H Cl 136-180ºC 1,28 min 554/556
A32
2-cloro-5-fluoro-pirid-4-ilo- F Cl H H Cl 124-126ºC 1,33 min 588/590
A33
2-metoxi-pirid-4-ilo- F Cl H H Cl 208-212ºC 1,30 min 566/568
A34
2,5-dicloro-pirid-4-ilo- F Cl H H Cl 188-191ºC - -
A35
2-cloro-pirid-4-ilo- F Cl H H Cl 119-123ºC - -
A36
2-cloro-pirid-4-ilo- H F F H Cl - 1,27 min 554/556
A37
2-cloro-pirid-4-ilo O-CF3 H H H Cl 74-74ºC 1,38 min 602/604
A38
2-cloro-5-fluoro-pirid-4-ilo- H CF3 F H F 195-198ºC 1,38 min 606/608
A39
2-cloro-5-fluoro-pirid-4-ilo- H F Cl H Cl 208-212ºC 1,38 min 588/590
18 19
Comp. nº
R1 R2 R3 R4 R5 R8 p. f. HPLC (RT) MS (ES+)
A40
2-cloro-5-fluoro-pirid-4-ilo- H F Cl H F 191-194ºC 1,31 min 572/574
A41
2-cloro-5-fluoro-pirid-4-ilo- H CF3 H H F 128-130ºC 1,30 min 588/590
A42
2-cloro-5-fluoro-pirid-4-ilo- F CF3 H H F 71-74ºC 1,39 min 606/608
A43
2-cloro-5-fluoro-pirid-4-ilo- F CF3 H H Cl 128-132ºC 1,42 min 622/624
A44
2,5-dicloro-pirid-4-ilo- H F Cl H F 197-199ºC 1,34 min 588/590
A45
2,5-dicloro-pirid-4-ilo- H CF3 F H F 198-200ºC 1,42 min 622/624
A46
2,5-dicloro-pirid-4-ilo- F CF3 H H F 74-76ºC 1,39 min 622/624
A47
2,5-dicloro-pirid-4-ilo- H F Cl H Cl 179-200ºC 1,41 min 604/606
A48
2,5-dicloro-pirid-4-ilo- F CF3 H H Cl 98-103ºC 1,43 min 638/640
A49
2,5-dicloro-pirid-4-ilo- H CF3 H H F 179-183ºC 1,33 min 604/606
A50
2,5-difluoro-pirid-4-ilo- H F Cl H F 177-178ºC 1,29 min 556/558
A51
2,5-difluoro-pirid-4-ilo- H F Cl H Cl 188-189ºC 1,33 min 572/574
A52
2,5-difluoro-pirid-4-ilo- H CF3 F H F 178-179ºC 1,35 min 590
A53
2,5-difluoro-pirid-4-ilo- H CF3 F H Cl 181-182ºC 1,41 min 606/608
A54
2,5-difluoro-pirid-4-ilo- F CF3 H H F 144-145ºC 1,32 min 590
A55
2,5-difluoro-pirid-4-ilo- F CF3 H H Cl 151-152ºC 1,38 min 606/608
A56
2,5-difluoro-pirid-4-ilo- H CF3 H H F 193-194ºC 1,29 min 572
A57
2-cloro-pirid-4-ilo- H F Cl H F 176-177ºC 1,28 min 554/556
A58
2-cloro-pirid-4-ilo- H F Cl H Cl 189-190ºC 1,33 min 570/572
A59
2-cloro-pirid-4-ilo- H CF3 F H F 163-166ºC 1,35 min 588/590
A60
2-cloro-pirid-4-ilo- F CF3 H H F 94-96ºC 1,33 min 588/590
imagen17
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E10724791
09-10-2014
Comp. nº
R1 R3 R4 R5 R8 p.f. HPLC (RT) MS (ES+)
B4
2-cloro-5-fluoro-pirid-4-ilo -CF3 H H Cl 214-216ºC 1,38 min 605/607
B5
2-cloro-pirid-4-ilo -CF3 H H H - 1,27 min 553/555
B6
2-cloro-pirid-4-ilo -OCHF2 H H Cl 182-188ºC 1,34 min 585/587
B7
2-cloro-pirid-4-ilo -CF3 H F Cl - 1,39 min 605/607
B8
2-cloro-pirid-4-ilo- Cl Cl H Cl 197ºC 1,35 min 589/591
B9
2-cloro-pirid-4-ilo- CF3 H H ciclopropilo - 1,33 min 593/595
B10
2-cloro-pirid-4-ilo- CF3 H H Br 180-180ºC 1,36 min 631/633
B11
2-cloro-pirid-4-ilo- CF3 H H CH3 1,25 min 567/569
B12
2,5-difluoro-pirid-4-ilo- CF3 H H Cl 188-189ºC 1,34 min 589/591
B13
2-cloro-5-fluoropirid-4-ilo- CF3 H H F 197-201ºC 1,38 min 589/591
B14
2-cloro-5-fluoropirid-4-ilo O-CHF2 H H Cl 169-172ºC 1,36 min 603/605
B15
2-cloro-5-fluoro-pirid-4-ilo O-CHF2 H H F 165-168ºC 1,30 min 587/589
B16
2,5-difluoropirid-4-ilo- CF3 H H F 197-198ºC 1,31 min 573
B17
2,5-dicloropirid-4-ilo- CF3 H H F 160-163ºC 1,35 min 605/607
B18
2,5-dicloropirid-4-ilo- CF3 H H Cl 93-96ºC 1,41 min 621/623
B19
2,5-difluoropirid-4-ilo- Cl Cl H F 222-223ºC 1,34 min 573/575
B20
2,5-difluoro-pirid-4-ilo O-CHF2 H H F 173-174ºC 1,25 min 571
B21
2,5-difluoro-pirid-4-ilo O-CHF2 H H Cl 170-171ºC 1,31 min 587/589
B22
2,5-difluoro-pirid-4-ilo- Cl Cl H Cl 232-237ºC 1,38 min 589/591
B23
2-cloro-5-fluoro-pirid-4-ilo- Cl Cl H F 225-229ºC 1,36 min 589/591
B24
2,5-dicloro-pirid-4-ilo O-CHF2 H H Cl 79-83ºC 1,36 min 619/621
B25
2,5-dicloro-pirid-4-ilo O-CHF2 H H F 204-206ºC 1,31 min 603/605
B26
2-cloro-pirid-4-ilo- Cl Cl H F 128-131ºC 1,30 min 571/573
Ejemplo 10
Este ejemplo ilustra la preparación de 2-cloro-N-(2-{1-[4-(5-cloro-pirimidin-2-il)-bencil]-1-oxi-piperidin-4-il}-4trifluorometil-fenil)-isonicotinamida (Compuesto C1 de la Tabla C)
imagen21
24
E10724791
09-10-2014
Una disolución de 2-cloro-N-(2-{1-[4-(5-cloro-pirimidin-2-il)-bencil]-1-oxi-piperidin-4-il}-4-trifluorometil-fenil)isonicotinamida (270 mg, Ejemplo 1) en diclorometano (12 ml) se trató con ácido 3-cloro-peroxibenzoico (92 mg) a temperatura ambiente. La disolución se agitó a temperatura ambiente durante 16 horas, y el precipitado se recogió mediante filtración. El sólido obtenido se aclaró con éter dietílico y se secó a alto vacío, para producir el compuesto del título como un polvo blanco. P.f. 193-194ºC. MS (ES+) 603/605 (MH+).
Los siguientes compuestos se prepararon según procedimientos análogos al descrito en el Ejemplo 10:
Tabla C:
Compuestos de fórmula (Ic)
imagen22
Comp. nº
R1 R2 R3 R4 R5 R8 p.f.
C1
2-cloro-pirid-4-ilo- H -CF3 H H Cl 193-194ºC
C2
2-cloro-pirid-4-ilo- H -CF3 H H F 178-179ºC
C3
2-cloro-5-fluoro-pirid-4-ilo- H -CF3 H H Cl 198-199ºC
C4
2-cloro-pirid-4-ilo- H -CF3 F H Cl 196-197ºC
C5
2-cloro-pirid-4-ilo- F -F H H Cl 183-184ºC
C6
2-cloro-pirid-4-ilo- F -CF3 H H Cl 207-209ºC
C7
2-fluoro-pirid-4-ilo- H CF3 F H Cl 193-196ºC
C8
2-metoxi-pirid-4-ilo- H CF3 F H Cl 183-186ºC
C9
2,6-dicloro-pirid-4-ilo- H CF3 F H Cl 193-196ºC
C10
2,5-dicloro-pirid-4-ilo- H CF3 F H Cl 188-192ºC
C11
2-cloro-5-fluoro-pirid-4-ilo- H CF3 F H Cl 184-187ºC
C12
2,6-dicloro-pirid-4-ilo- F Cl H H Cl 194-197ºC
C13
2-fluoro-pirid-4-ilo- F Cl H H Cl >220ºC
C14
2-cloro-5-fluoro-pirid-4-ilo- F Cl H H Cl 191-195ºC
C15
2-metoxi-pirid-4-ilo- F Cl H H Cl 183-187ºC
C16
2-cloro-pirid-4-ilo- F Cl H H Cl 199-205ºC
C17
2,5-dicloro-pirid-4-ilo- F Cl H H Cl 208-211ºC
Ejemplo 11
Este ejemplo ilustra la preparación de 2-cloro-N-{1’-[4-(5-cloro-pirimidin-2-il)-bencil]-6-metil-1’,2’,3’,4’,5’,6’-hexahidro[2,4’]bipiridinil-3-il}-isonicotinamida (Compuesto D1 de la Tabla D)
25
imagen23
imagen24
Tabla E:
Compuestos de fórmula (Ie)
28
imagen25
Comp. nº
R1 R2 R3 R4 R5 R8 HX p.f.
E1
2-cloro-pirid-4-ilo- H -CF3 H H Cl CH3 CO2 H 222-223ºC
E2
2-cloro-pirid-4-ilo- H -CF3 H H F CH3 CO2 H 154ºC
E3
2-cloro-pirid-4-ilo- H -CF3 H H Cl HCl 282-283ºC
E4
2-cloro-pirid-4-ilo- H CF3 H H Cl Ácido 2-hidroxi-benzoico 225ºC
E5
2-cloro-pirid-4-ilo- H CF3 H H Cl Ácido 2,3,4,5-tetrahidroxi-6-oxohexanoico 165ºC
E6
2-cloro-pirid-4-ilo- H CF3 H H Cl Ácido 2-clorobenzoico 166ºC
E7
2-cloro-pirid-4-ilo- H CF3 H H Cl Ácido fosfórico 125ºC
E8
2-cloro-pirid-4-ilo- H CF3 H H Cl Ácido 3-hidroxi-propano-1-sulfónico 183ºC
E9
2-cloro-pirid-4-ilo- H CF3 H H Cl Ácido etanosulfónico 260ºC
E10
2-cloro-pirid-4-ilo- H CF3 H H Cl Ácido tolueno-4-sulfónico 242ºC
imagen26
imagen27

Claims (1)

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ES10724791.8T 2009-07-06 2010-06-07 Compuestos insecticidas Active ES2514318T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP09164662 2009-07-06
EP09164662 2009-07-06
PCT/EP2010/057907 WO2011003684A1 (en) 2009-07-06 2010-06-07 Insecticidal compounds

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ES2514318T3 true ES2514318T3 (es) 2014-10-28

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AR (1) AR077380A1 (es)
AU (1) AU2010270464B2 (es)
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CA (1) CA2765012A1 (es)
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CR (1) CR20110702A (es)
EA (1) EA019857B1 (es)
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MA (1) MA33416B1 (es)
MX (1) MX2011013446A (es)
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UA (1) UA103540C2 (es)
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GB0414438D0 (en) 2004-06-28 2004-07-28 Syngenta Participations Ag Chemical compounds
CN105517993B (zh) 2013-07-08 2018-07-13 百时美施贵宝公司 芳基酰胺激酶抑制剂
GB201604970D0 (en) * 2016-03-23 2016-05-04 Syngenta Participations Ag Improvements in or relating to organic compounds

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EA005934B1 (ru) * 2001-07-05 2005-08-25 Х. Лундбекк А/С Замещённые анилиновые пиперидины в качестве селективных антагонистов мсн
US6727264B1 (en) * 2001-07-05 2004-04-27 Synaptic Pharmaceutical Corporation Substituted anilinic piperidines as MCH selective antagonists
CN102229605B (zh) * 2001-10-26 2015-01-14 Msd意大利有限公司 关于hiv整合酶的n-取代的羟基嘧啶酮甲酰胺抑制剂
US7381721B2 (en) * 2003-03-17 2008-06-03 Adolor Corporation Substituted piperidine compounds
GB0414438D0 (en) * 2004-06-28 2004-07-28 Syngenta Participations Ag Chemical compounds
GB0813436D0 (en) * 2008-07-22 2008-08-27 Syngenta Participations Ag Insecticidal compounds

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EP2451801B1 (en) 2014-08-13
AU2010270464A1 (en) 2012-01-12
EP2451801A1 (en) 2012-05-16
JP2012532172A (ja) 2012-12-13
CN102471316A (zh) 2012-05-23
US20120115884A1 (en) 2012-05-10
CR20110702A (es) 2012-02-09
CN102471316B (zh) 2013-12-11
CA2765012A1 (en) 2011-01-13
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