ES2574414T3 - Compuestos de pirazol pesticidas novedosos - Google Patents

Compuestos de pirazol pesticidas novedosos Download PDF

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ES2574414T3
ES2574414T3 ES12713758.6T ES12713758T ES2574414T3 ES 2574414 T3 ES2574414 T3 ES 2574414T3 ES 12713758 T ES12713758 T ES 12713758T ES 2574414 T3 ES2574414 T3 ES 2574414T3
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ch2ch3
ch2och3
chfch3
ch2s
ch2ch2
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ES2574414T7 (es
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Christian Defieber
Sebastian SÖRGEL
Daniel SÄLINGER
Ronan Le Vezouet
Karsten KÖRBER
Steffen Gross
Deborah L. Culbertson
Koshi Gunjima
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BASF SE
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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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-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
    • A01N43/72—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
    • A01N43/74—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 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07D417/14—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 three or more hetero rings

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Health & Medical Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pretreatment Of Seeds And Plants (AREA)
  • Catching Or Destruction (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Compuestos de pirazol novedosos de fórmula I**Fórmula** en la que U es N o CH; T es O o S; R1 es H, alquilo C1-C2 o (alcoxi C1-C2)-alquilo C1-C2; R2 es CH3 o halometilo; R3 es alquilo C2-C6, haloalquilo C1-C6, (alcoxi C1-C2)-alquilo C1-C2, alquenilo C2-C6 y alquinilo C2-C6, cicloalquilo C3- C6, cicloalquenilo C5-C6, alcoxilo C1-C6, CN, NO2, S(O)nRb, en los que los átomos de C pueden no estar sustituidos o estar parcial o completamente sustituidos con Ra; Ra es halógeno, CN, NO2, alquilo C1-C2, haloalquilo C1-C2, alcoxilo C1-C4, halo-alcoxilo C1-C2 o S(O)nRb; n es 0, 1, o 2; Rb es hidrógeno, alquilo C1-C2, haloalquilo C1-C2, cicloalquilo C3-C6 o alcoxilo C1-C4, R4 es alquilo C1-C4 o un grupo mencionado para R3; R5 es H o un grupo mencionado para R4; R3 y R4 pueden formar juntos un carbo o heterociclo de tres a seis miembros, que puede contener 1 ó 2 heteroátomos seleccionados de N-Rc, O y S, en los que S puede estar oxidado, carbo o heterociclo que puede estar sustituido con Ra; Rc es hidrógeno, alquilo C1-C2, haloalquilo C1-C2, alquilcarbonilo C1-C2 o (alcoxi C1-C2)-carbonilo; y los estereoisómeros, sales, tautómeros y N-óxidos de los mismos.

Description

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F.VI-2) Inhibidores de proteínas G: quinolinas: quinoxifeno;
F.VII) Inhibidores de la síntesis de lípidos y membranas
F.VIII-1) Principios activos inorgánicos: Mezcla de Bordeaux, acetato de cobre, hidróxido de cobre, oxicloruro de cobre, sulfato básico de cobre, azufre;
F.VIII-2) Tio-y ditiocarbamato: ferbam, mancozeb, maneb, metam, metasulfocarb, metiram, propineb, thiram, zineb, ziram;
F.VIII-3) Compuestos de organocloro (por ejemplo ftalimidas, sulfamidas, cloronitrilos):
anilazina, clorotalonilo, captafol, captán, folpet, diclofluanida, diclorofeno, flusulfamida, hexaclorobenceno, pentaclorfenol y sus sales, ftalida, tolilfluanida, N-(4-cloro-2-nitro-fenil)-N-etil-4-metil-bencenosulfonamida;
F.VIII-4) Guanidinas: guanidina, dodina, base libre de dodina, guazatina, acetato de guazatina, iminoctadina, triacetato de iminoctadina, tris(albesilato) de iminoctadina;
F.VIII-5) Antraquinonas: ditianona;
F.IX) Inhibidores de la síntesis de la pared celular
F.IX-1) Inhibidores de la síntesis de glucano: validamicina, polioxina B;
F.IX-2) Inhibidores de la síntesis de melanina: piroquilón, tricoclazol, carpropamida, diciclomet, fenoxanilo;
F.X) Inductores de la defensa de plantas
F.X-1) Ruta del ácido salicílico: acibenzolar-S-metilo;
F.X-2) Otros: probenazol, isotianilo, tiadinilo, prohexadiona de calcio;
fosfonatos: fosetilo, fosetilo de aluminio, ácido fosforoso y sus sales;
F.XI) Modo de acción desconocido: bronopol, quinometionat, ciflufenamida, cimoxanilo, dazomet, debacarb, diclomezina, difenzoquat, metilsulfato de difenzoquat, difenilamina, flumetover, flusulfamida, flutianilo, metasulfocarb, oxina de cobre, proquinazid, tebufloquina, tecloftalam, triazoxida, 2-butoxi-6-yodo-3-propil-cromen-4-ona, N(ciclopropilmetoxiimino-(6-difluoro-metoxi-2,3-difluoro-fenil)-metil)-2-fenilacetamida, N’-(4-(4-cloro-3trifluorometilfenoxi)-2,5-dimetil-fenil)-N-etil-N-metil-formamidina, N’-(4-(4-fluoro-3-trifluorometil-fenoxi)-2,5-dimetilfenil)-N-etil-N-metil-formamidina, N’-(2-metil-5-trifluorometil-4-(3-trimetilsilanil-propoxi)-fenil)-N-etil-N-metilformamidina, N’-(5-difluorometil-2-metil-4-(3-trimetilsilanil-propoxi)-fenil)-N-etil-N-metil-formamidina, metil-(1,2,3,4tetrahidro-naftalen-1-il)-amida del ácido 2-{1-[2-(5-metil-3-trifluorometil-pirazol-1-il)-acetil]-piperidin-4-il}-tiazol-4carboxílico, metil-(R)-1,2,3,4-tetrahidro-naftalen-1-il-amida del ácido 2-{1-[2-(5-metil-3-trifluorometil-pirazol-1-il)acetil]-piperidin-4-il}-tiazol-4-carboxílico, éster de 6-terc-butil-8-fluoro-2,3-dimetilquinolin-4-ilo del ácido metoxi-acético y N-metil-2-{1-[(5-metil-3-trifluorometil-1H-pirazol-1-il)-acetil]-piperidin-4-il}-N-[(1R)-1,2,3,4-tetrahidronaftalen-1-il]-4tiazolcarboxamida, 3-[5-(4-cloro-fenil)-2,3-dimetil-isoxazolidin-3-il]-piridina, pirisoxazol, éster S-alílico del ácido 5amino-2-isopropil-3-oxo-4-orto-tolil-2,3-dihidropirazol-1-carbotioico, amida del ácido N-(6-metoxi-piridin-3il)ciclopropanocarboxílico, 5-cloro-1(4,6-dimetoxi-pirimidin-2-il)-2-metil-1H-benzoimidazol, 2-(4-cloro-fenil)-N-[4-(3,4dimetoxi-fenil)-isoxazol-5-il]-2-prop-2-iniloxi-acetamida;
F.XI) Reguladores del crecimiento: ácido abscísico, amidocloro, ancimidol, 6-bencilaminopurina, brasinolida, butralina, clormequat (cloruro de clormequat), cloruro de colina, ciclanilida, daminozida, dikegulac, dimetipina, 2,6dimetilpuridina, etefón, flumetralina, flurprimidol, flutiacet, forclorfenurón, ácido giberélico, inabenfida, ácido indol-3acético, hidrazida maleica, mefluidida, mepiquat (cloruro de mepiquat), ácido naftalenoacético, N-6-benciladenina, paclobutrazol, prohexadiona (prohexadiona de calcio), prohidrojasmon, tidiazuron, triapentenol, fosforotritioato de tributilo, ácido 2,3,5-triyodobenzoico, trinexapac-etilo y uniconazol;
F.XII) Agentes de control biológico: antes de biocontrol antifúngico:
cepa de Bacillus substilis con NRRL n.º B-21661 (por ejemplo RHAP-SODY®, SERENADE® MAX y SERENADE® ASO de AgraQuest, Inc., EE.UU.), cepa de Bacillus pumilus con NRRL n.º B-30087 (por ejemplo SONATA® y BALLAD® Plus de AgraQuest, Inc., EE.UU.), Ulocladium oudemansii (por ejemplo el producto BOTRY-ZEN de BotriZen Ltd., Nueva Zelanda), quitosano (por ejemplo ARMOUR-ZEN de BotriZen Ltd., Nueva Zelanda).
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Nº.
T U R1 R2 R3 R4 R5 Datos físicos (HPLC / MS)
RT [min]
Método m/z [MH]+
I-14
O N CH2CH3 CH3 -(CH2)5- H 2,459 1 314,2
I-15
O N CH2CH3 CH3 -(CH2)3- H 2,105 1 286,2
I-16
O N CH3 CH3 -(CH2)3- H 1,876 1 272,1
I-17
O N CH3 CH3 CH2C(CH3)2OCH3 CH3 H 2,098 1 332,2
I-18
O N CH2CH3 CH3 CH2C(CH3)2OCH3 CH3 H 2,229 1 346,2
I-19
O N H CH3 -(CH2)3- H 1,984 1 258,1
I-20
O N H CH3 CH2C(CH3)2OCH3 CH3 H 2,118 1 318,2
I-21
O N H CH3 -CH2CH2OCH2CH2- H 1,643 1 288,1
I-22
O N CH2CH3 CH3 -CH2CH2OCH2CH2- H 1,634 1 316,1
I-23
O N CH3 CH3 -CH2CH2OCH2CH2- H 1,562 1 302,2
I-24
O N CH2OCH2CH3 CH3 c-C3H5 CH3 H 2,416 1 330,2
I-25
O N H CH3 CH2OCH3 CH3 CH3 1,965 1 290,2
I-26
O N CH3 CH3 CH2OCH3 CH3 CH3 1,908 1 304,2
I-27
O N CH2OCH2CH3 CH3 CF3 CH3 H 2,463 1 358,1
I-28
O N CH3 CH3 CF2CHFCF3 CH3 H 2,562 1 396,1
I-29
O N CH3 CH3 CF2CHF2 CH3 H 2,106 1 346,1
I-30
O N H CH3 CF2CHFCF3 CH3 H 2,552 1 382,1
I-31
O N H CH3 CF2CHF2 CH3 H 2,144 1 332,1
I-32
O N H CH3 CN CH3 CH3 1,817 1 271,1
I-33
O N CH3 CH3 CN CH3 CH3 1,762 1 285,0
I-34
O N H CH3 CF3 CF3 H 2,278 1 354,1
I-35
O N H CH3 CN CH3 H 1,423 1 257,1
I-36
O N CH3 CH3 CN CH3 H 1,401 1 271,1
I-37
O N CH2CH3 CH3 CF3 CF3 H 2,519 1 382,1
I-38
O N CH3 CH3 CF3 CF3 H 2,271 1 368,1
I-39
O N H CH3 1-F-c-C3H4 CH3 H 1,910 1 290,1
I-40
O N CH3 CH3 1-F-c-C3H4 CH3 H 1,838 1 304,1
I-41
O N H CH3 C(CH3)3 CH3 H 2,436 1 288,2
I-42
O N CH3 CH3 C(CH3)3 CH3 H 2,398 1 302,2
I-43
O N CH2OCH3 CH3 C(CH3)3 CH3 H 2,509 1 332,2
I-44
O C H CH3 C(CH3)3 CH3 H 2,282 1 287,2
I-45
O C CH3 CH3 C(CH3)3 CH3 H 2,139 1 301,2
I-46
O N CH2CH3 CH3 C(CH3)3 CH3 H 2,532 1 316,2
I-47
O N H CH3 CH2CH3 CH2CH3 H 2,129 1 274,2
I-48
O N CH3 CH3 CH2CH3 CH2CH3 H 2,071 1 288,2
I-49
O N CH2OCH3 CH3 CH2CH3 CH2CH3 H 2,231 1 318,2
I-50
O C H CH3 CH2CH3 CH2CH3 H 2,110 1 273,2
I-51
O C CH3 CH3 CH2CH3 CH2CH3 H 1,946 1 287,2
I-52
O N H CF3 CH2CH3 CH2CH3 H 2,734 1 328,1
I-53
O N CH3 CF3 CH2CH3 CH2CH3 H 2,788 1 342,1
I-54
O N CH2OCH3 CF3 CH2CH3 CH2CH3 H 2,955 1 372,2
I-55
O C H CF3 CH2CH3 CH2CH3 H 2,523 1 327,1
I-56
O N H CF3 C(CH3)3 CH3 H 2,936 1 342,1
I-57
O N CH3 CF3 C(CH3)3 CH3 H 3,049 1 356,2
I-58
O N CH2OCH3 CF3 C(CH3)3 CH3 H 3,278 1 386,2
I-59
O C H CF3 C(CH3)3 CH3 H 2,781 1 341,2
I-60
O C CH2OCH2CH3 CH3 c-C3H5 CH3 H 2,134 1 329,1
I-61
S C CH3 CH3 CF3 CH3 H 2,351 1 329,0
I-62
S C CH2CH3 CH3 c-C3H5 CH3 H 2,569 1 315,2
I-63
S C H CH3 CF3 CH3 H 2,246 1 315,1
I-64
S C CH2CH3 CH3 CF3 CH3 H 2,524 1 343,0
I-65
O N H CH3 -CCl2CH2- H 2,143 1 312,0
I-66
O N CH3 CH3 -CCl2CH2- H 2,073 1 326,0
I-67
O C CH2OCH2CH3 CH3 CF3 CH3 H 0,868 2 357,2
I-68
O N H CH3 CH=CH2 CH3 H 0,716 2 258,0
I-69
O N CH3 CH3 CH=CH2 CH3 H 0,708 2 272,0
I-70
O N CH2CH3 CH3 CH=CH2 CH3 H 0,761 2 286,1
I-71
O N CH2OCH3 CH3 CH=CH2 CH3 H 0,776 2 302,1
I-72
O C CH3 CF3 CH2CH3 CH2CH3 H 2,597 1 341,1
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Nº.
T U R1 R2 R3 R4 R5 Datos físicos (HPLC / MS)
RT [min]
Método m/z [MH]+
I-73
O N CH3 CH3 -CH2CH2N(CH3)CH2CH2- H 0,727 2 315,1
I-74
O N H CH3 CH2CN CH3 H 1,525 1 271,1
I-75
O N CH3 CH3 CH2CN CH3 H 1,466 1 285,1
I-76
O N CH2CH3 CH3 CH2CN CH3 H 1,647 1 299,2
I-77
O N CH2OCH3 CH3 CH2CN CH3 H 1,669 1 315,1
I-78
O C CH2CH3 CH3 CH2CN CH3 H 0,613 2 298,2
I-79
O N CH2CH3 CH3 CF3 CH3 CH3 0,866 2 342,2
I-80
O N H CH3 CF3 CH3 CH3 0,797 2 314
I-81
O C CH3 CH3 CF3 CH3 CH3 0,767 2 327,2
I-82
O N H CH3 -(CH2)5- CN 0,831 2 311,1
I-83
O C H CH3 CF3 CH3 CH3 0,783 2 313,2
I-84
O C CH3 CH3 -(CH2)5- CN 0,809 2 324,1
I-85
O N CH3 CH3 CF3 CH3 CH3 0,806 2 328,1
I-86
O C CH2CH3 CH3 CF3 CH3 CH3 0,833 2 341,1
I-87
O N CH2OCH2CH3 CH3 CF3 CH3 CH3 0,944 2 372,2
I-88
O N CH2OCH3 CH3 CF3 CH3 CH3 0,884 2 358,2
1-89
O N H CH3 -CH2CH2N(CH3)CH2CH2- H 0,502 2 301,2
I-90
O C H CH3 -CH2CH2N(CH3)CH2CH2- H 0,497 2 300,1
I-91
O C CH2OCH3 CH3 CF3 CH3 CH3 0,848 2 357,2
I-92
O N CH3 CH3 1-CN-c-C3H4 CH3 H 1,584 1 311,1
I-93
O N H CH3 1-CN-c-C3H4 CH3 H 1,739 1 297,1
I-94
O C H CH3 CH2CN CH3 H 1,504 1 270,1
I-95
O N H CH3 CH(CH3)2 CH3 H 2,108 1 274,1
I-96
O N CH3 CH3 CH(CH3)2 CH3 H 2,063 1 288,1
I-97
O N CH2OCH3 CH3 CH(CH3)2 CH3 H 0,946 2 318,1
I-98
O N CH2CH3 CH3 CH(CH3)2 CH3 H 0,838 2 302,4
I-99
O C H CH3 CH(CH3)2 CH3 H 2,030 1 273,1
I-100
O C CH3 CH3 CH(CH3)2 CH3 H 1,859 1 287,1
I-101
O C CH2CH3 CH3 CH(CH3)2 CH3 H 2,000 1 301,1
I-102
O N H CH3 CF3 CH2CH3 H 0,795 2 314,2
I-103
O N CH3 CH3 CF3 CH2CH3 H 2,011 1 328,1
I-104
O N CH2CH3 CH3 CF3 CH2CH3 H 2,172 1 342,1
I-105
O N CH2OCH3 CH3 CF3 CH2CH3 H 2,210 1 358,1
I-106
O C H CH3 CF3 CH2CH3 H 2,128 1 313,1
I-107
O C CH3 CH3 CF3 CH2CH3 H 1,956 1 327,1
I-108
O C CH2CH2OCH3 CH3 CF3 CH2CH3 H 2,146 1 357,0
I-109
O C CH3 CH3 CH2CN CH3 H 1,307 1 284,0
I-110
O N CH3 CH3 -(CH2)5- CF3 2,596 1 368,1
I-111
O N CH2CH3 CH3 -(CH2)5- CF3 2,719 1 382,1
I-112
O N CH2OCH2CH3 CH3 -(CH2)5- CF3 1,075 2 412,2
I-113
O N CH2OCH3 CH3 -(CH2)5- CF3 2,775 1 398,1
I-114
O N H CH3 -(CH2)5- CF3 0,948 2 354,2
I-115
O C CH2OCH2CH3 CH3 CF3 CH3 CH3 0,812 2 371,4
I-116
O C H CH3 -(CH2)5- CF3 0,917 2 353,2
I-117
O C CH3 CH3 -(CH2)5- CF3 0,917 2 367,1
I-118
O C CH2CH3 CH3 -(CH2)5- CF3 0,975 2 381,1
I-119
O N CH2CH3 CH3 -CH2CH20CH2CH2- CF3 0,841 2 384,1
I-120
O N CH3 CH3 -CH2CH2OCH2CH2- CF3 0,791 2 370,1
I-121
O N H CH3 -CH2CH2OCH2CH2- CF3 0,778 2 356,1
I-122
O C CH3 CH3 -CH2CH2OCH2CH2- CF3 1,865 1 369,1
I-123
O C H CH3 -CH2CH2OCH2CH2- CF3 0,761 2 355,1
I-124
O N H CH3 CH2CH2OCH3 CH3 H 1,717 1 290,1
I-125
O N CH3 CH3 CH2CH2OCH3 CH3 H 1,667 1 304,1
I-126
O C H CH3 CH2CH2OCH3 CH3 H 0,666 2 289,5
I-127
O C CH3 CH3 CH2CH2OCH3 CH3 H 1,538 1 303,1
I-128
O C CH2CH3 CH3 CH2CH2OCH3 CH3 H 0,717 2 317,6
I-129
O N CH2CH3 CH3 CH2CH2OCH3 CH3 H 0,747 2 318,5
I-130
O N CH3 CH3 -(CH2)5- CN 2,226 1 325,1
I-131
O C CH2CH3 CH3 -(CH2)5- CN 2,343 1 338,2
31
Nº.
T U R1 R2 R3 R4 R5 Datos físicos (HPLC / MS)
RT [min]
Método m/z [MH]+
I-132
O N H CH3 CH2F CH3 H 0,654 2 264,0
I-133
O N CH3 CH3 CH2F CH3 H 0,645 2 278,3
I-134
O N CH2CH3 CH3 CH2F CH3 H 0,719 2 292,3
I-135
O C CH2CH3 CH3 CH2F CH3 H 0,684 2 291,2
I-136
O C H CH3 CH2F CH3 H 1,443 1 263,1
I-137
O C CH3 CH3 CH2F CH3 H 1,008 1 277,1
I-138
O C H CH3 -(CH2)5- CN 2,275 1 310,1
I-139
O N CH2CH3 CH3 -(CH2)5- CN 0,906 2 339,5
I-140
O N H CH3 CHFCH3 CH3 H 0,708 (A) 2 278,2
I-141
O N CH3 CH3 CHFCH3 CH3 H 0,708 (A) 2 292,5
I-142
O N CH2CH3 CH3 CHFCH3 CH3 H 0,765 (A) 2 306,1
I-143
O C H CH3 CHFCH3 CH3 H 0,686 (A) 2 277,3
I-144
O C CH3 CH3 CHFCH3 CH3 H 0,677 (A) 2 291,2
I-145
O C CH2CH3 CH3 CHFCH3 CH3 H 0,731 (A) 2 305,5
I-146
O N H CH3 CHFCH3 CH3 H 0,698 (B) 2 278,1
I-147
O N CH3 CH3 CHFCH3 CH3 H 0,692 (B) 2 292,3
I-148
O N CH2CH3 CH3 CHFCH3 CH3 H 0,743 (B) 2 306,1
I-149
O C H CH3 CHFCH3 CH3 H 0,675 (B) 2 277,1
I-150
O C CH3 CH3 -CH2CH2OCH2CH2- CF3 0,756 (S) 2 369,1
I-151
O C CH2CH3 CH3 -CH2CH2OCH2CH2- CF3 2,010 (S) 1 383,1
I-152
O N CH2CH3 CH3 CN CH3 CH3 0,747 2 299,3
I-153
O N CH3 CH3 -CH2CH2- CN 0,625 2 283,0
I-154
O N H CH3 -CH2CH2- CN 0,634 2 269,1
I-155
O N CH2CH3 CH3 -CH2CH2- CN 0,679 2 297,0
I-156
O C CH2CH3 CH3 CHFCH3 CH3 H 0,656 (B) 2 305,4
I-157
O C CH3 CH3 CHFCH3 CH3 H 0,656 (B) 2 291,3
I-158
O C CH2CH3 CH3 CN CH3 CH3 0,720 2 298,0
I-159
O N CH2CH3 CH3 1-CN-c-C3H4 CH3 H 0,717 2 325,1
I-160
O N H CH3 CHF2 CH3 H 0,687 2 282,2
I-161
O N CH3 CH3 CHF2 CH3 H 0,680 2 296,3
I-162
O N CH2CH3 CH3 CHF2 CH3 H 0,737 2 310,4
I-163
O C H CH3 CHF2 CH3 H 0,666 2 281,3
I-164
O C CH2CH3 CH3 CHF2 CH3 H 0,706 2 309,3
I-165
O C CH3 CH3 CHF2 CH3 H 0,639 2 295,3
I-166
O C CH3 CH3 -CH2S(O)2CH2- H 0,488 2 321,2
I-167
O C CH2CH3 CH3 -CH2S(O)2CH2- H 0,545 2 335,2
I-168
O N CH3 CH3 -CH2CH2N[C(O)CH3]CH2CH2- H 0,605 2 343,2
I-169
O N CH2CH3 CH3 -CH2S(O)2CH2- H 0,603 2 336,2
I-170
O C H CH3 -CH2S(O)2CH2- H 0,511 2 307,2
I-171
O N H CH3 -CH2S(O)2CH2- H 0,523 2 308,2
I-172
O N CH3 CH3 -CH2S(O)2CH2- H 0,511 2 322,2
I-173
O N CH3 CH3 -CH2SCH2- H 0,686 2 290,1
I-174
O N H CH3 -CH2SCH2- H 0,693 2 276,1
I-175
O C H CH3 -CH2SCH2- H 0,677 2 275,1
I-176
O C CH3 CH3 -CH2SCH2- H 0,666 2 289,1
32
Nº.
T U R1 R2 R3 R4 R5 Datos físicos (HPLC / MS)
RT [min]
Método m/z [MH]+
I-177
O C CH2CH3 CH3 -CH2SCH2- H 0,676 2 303,1
I-178
O N CH3 CH3 CH(CH3)2 CH(CH3)2 H 0,914 2 316,4
I-179
O N H CH3 CH(CH3)2 CH(CH3)2 H 0,909 2 302,3
I-180
O C H CH3 CH(CH3)2 CH(CH3)2 H 0,873 2 301,5
I-181
O C CH3 CH3 CH(CH3)2 CH(CH3)2 H 0,881 2 315,5
I-182
O C CH2CH3 CH3 CH(CH3)2 CH(CH3)2 H 0,953 2 329,4
I-183
O N CH2CH3 CH3 CH(CH3)2 CH(CH3)2 H 0,962 2 330,5
I-184
O N CH2CH3 CH3 -CH2SCH2- H 0,741 2 304,1
I-185
O N H CH3 -CH2S(O)CH2- H 0,507 2 292,2
I-186
O N CH3 CH3 -CH2S(O)CH2- H 0,487 2 306,2
I-187
O C CH3 CH3 CN CH3 CH3 0,668 2 284,0
I-188
O C H CH3 CN CH3 CH3 0,663 2 270,3
I-189
O N CH2CH3 CH3 -CH2S(O)CH2- H 0,573 2 320,2
I-190
O C H CH3 -CH2S(O)CH2- H 0,488 2 291,2
I-191
O N H CH3 CH(CH2CH3)CH (CH3)2 CH3 H 0,987 2 316,5
I-192
O N CH3 CH3 CH(CH2CH3)CH (CH3)2 CH3 H 0,987 2 330,4
I-193
O N CH2CH3 CH3 CH(CH2CH3)CH (CH3)2 CH3 H 1,035 2 344,6
I-194
O C H CH3 CH(CH2CH3)CH (CH3)2 CH3 H 0,946 2 315,4
I-195
O C CH3 CH3 CH(CH2CH3)CH (CH3)2 CH3 H 0,959 2 329,5
I-196
O C CH2CH3 CH3 CH(CH2CH3)CH (CH3)2 CH3 H 1,024 2 343,6
I-197
O N H CH3 CH2CH(CH3)2 CH3 H 0,875 2 288,3
I-198
O N CH3 CH3 CH2CH(CH3)2 CH3 H 0,868 2 302,3
I-199
O N CH2CH3 CH3 CH2CH(CH3)2 CH3 H 0,915 2 316,2
I-200
O C H CH3 CH2CH(CH3)2 CH3 H 0,841 2 287,4
I-201
O C CH3 CH3 CH2CH(CH3)2 CH3 H 0,835 2 301,4
I-202
O C CH2CH3 CH3 CH2CH(CH3)2 CH3 H 0,899 2 315,4
I-203
O N H CH3 CF3 CH(CH3)2 H 0,850 2 328,1
I-204
O N CH3 CH3 CF3 CH(CH3)2 H 0,859 2 342,0
I-205
O N CH2CH3 CH3 CF3 CH(CH3)2 H 0,917 2 356,1
I-206
O C H CH3 CF3 CH(CH3)2 H 0,834 2 327,3
I-207
O C CH3 CH3 CF3 CH(CH3)2 H 0,842 2 341,2
I-208
O C CH2CH3 CH3 CF3 CH(CH3)2 H 0,903 2 355,3
I-209
O C CH2CH3 CH3 CF3 c-C3H5 H 0,838 2 353,4
I-210
O N H CH3 CF3 c-C3H5 H 0,826 2 326,2
I-211
O N CH3 CH3 CF3 c-C3H5 H 0,827 2 340,3
I-212
O N CH2CH3 CH3 CF3 c-C3H5 H 0,873 2 354,3
I-213
O C H CH3 CF3 c-C3H5 H 0,796 2 325,2
I-214
O C CH3 CH3 CF3 c-C3H5 H 0,781 2 339,0
I-215
O N H CH3 1-S(O)2CH3-c-C3H4 CH3 H 0,661 2 350,1
I-216
O N CH3 CH3 1-S(O)2CH3-c-C3H4 CH3 H 0,665 2 364,1
I-217
O N CH2CH3 CH3 1-S(O)2CH3-c-C3H4 CH3 H 0,719 2 378,1
I-218
O C H CH3 1-S(O)2CH3-c-C3H4I CH3 H 0,653 2 349,1
I-219
O C CH3 CH3 1-S(O)2CH3-c-C3H4I CH3 H 0,651 2 363,0
I-220
O C CH2CH3 CH3 1-S(O)2CH3-c-C3H4 CH3 H 0,706 2 377,2
I-221
O C CH3 CF3 C(CH3)3 CH3 H 2,877 1 355,1
I-222
O N H CH3 1-CH3-c-C3H4 CH3 H 0,816 2 286,2
I-223
O N CH2CH3 CH3 1-CH3-c-C3H4 CH3 H 0,870 2 314,2
33
Nº.
T U R1 R2 R3 R4 R5 Datos físicos (HPLC / MS)
RT [min]
Método m/z [MH]+
I-224
O C H CH3 1-CH3-c-C3H4 CH3 H 0,790 2 285,2
I-225
O C CH3 CH3 1-CH3-c-C3H4 CH3 H 0,768 2 299,2
I-226
O N CH3 CH3 2,2-Cl2-C-C3H3 CH3 H 0,827 2 354,1
I-227
O N H CH3 -CH2CH2N[C(O)CH3]CH2CH2- H 0,624 2 329,1
I-228
O N H CH3 C(CH3)2CN CH3 H 0,695 2 299,0
I-229
O N CH3 CH3 C(CH3)2CN CH3 H 0,698 2 313,1
I-230
O N CH2CH3 CH3 C(CH3)2CN CH3 H 0,754 2 327,2
I-231
O N CH2CH3 CH3 CH2CF3 CH3 H 0,808 2 342,1
I-232
O N H CH3 CH2CF3 CH3 H 0,760 2 314,1
I-233
O N CH3 CH3 1-CH3-c-C3H4 CH3 H 0,817 2 300,2
I-234
O C CH3 CH3 2,2-Cl2-C-C3H3 CH3 H 0,795 (S) 2 353,1
I-235
O N CH2CH3 CH3 2,2-Cl2-C-C3H3 CH3 H 0,883 (S) 2 368,1
I-236
O C CH2CH3 CH3 2,2-Cl2-C-C3H3 CH3 H 0,848 (S) 2 367,1
I-237
O N H CH3 2,2-Cl2-C-C3H3 CH3 H 0,831 2 340,1
I-238
O N CH3 CH3 CH2CF3 CH3 H 0,752 2 328,1
I-239
O N H CH3 1-SCH3-c-C3H4 CH3 H 0,820 2 318,0
I-240
O N CH3 CH3 1-SCH3-c-C3H4 CH3 H 0,816 2 332,0
I-241
O N CH2CH3 CH3 1-SCH3-c-C3H4 CH3 H 0,873 2 346,0
I-242
O C H CH3 1-SCH3-c-C3H4 CH3 H 0,785 2 317,0
I-243
O C CH3 CH3 1-SCH3-c-C3H4 CH3 H 0,793 2 331,0
I-244
O C CH2CH3 CH3 1-SCH3-c-C3H4 CH3 H 0,849 2 345,2
I-245
O C H CH3 2,2-Cl2-C-C3H3 CH3 H 0,801 2 339,1
I-246
O C CH2CH3 CH3 1-CH3-c-C3H4 CH3 H 0,828 (S) 2 313,2
I-247
O N CH2CH3 CH3 CF3 C (CH3)3 H 0,986 2 370,3
I-248
O N CH3 CH3 CF3 C (CH3)3 H 0,926 2 356,5
I-249
O N H CH3 CF3 C (CH3)3 H 0,909 2 342,4
I-250
O N H CH3 1-CF3-c-C3H4 CH3 H 2,417 1 340,1
I-251
O N CH2CH3 CH3 1-CF3-c-C3H4 CH3 H 2,535 1 368,2
I-252
O N CH3 CH3 1-CF3-c-C3H4 CH3 H 0,865 2 354,1
I-253
O N H CH3 c-C3H5 CH3 H 2,047 1 272,1
I-254
O N CH3 CH3 c-C3H5 CH3 H 2,028 1 286,2
I-255
O N CH3 CH3 CF3 CH3 H 0,728 2 314,1
I-256
O N H CH3 CF3 CH3 H 2,025 1 300,1
I-257
O N CH2CH3 CH3 CF3 CH3 H 0,798 2 328,1
I-258
O N CH2OCH3 CH3 c-C3H5 CH3 H 2,133 1 316,2
I-259
O N CH2OCH3 CH3 CF3 CH3 H 2,483 1 344,1
I-260
O C CH3 CH3 c-C3H5 CH3 H 1,801 1 285,1
I-261
O C H CH3 c-C3H5 CH3 H 1,965 1 271,1
I-262
O C CH2OCH3 CH3 c-C3H5 CH3 H 1,954 1 315,1
I-263
O C H CH3 CF3 CH3 H 1,889 1 299,0
I-264
O C CH3 CH3 CF3 CH3 H 1,768 1 313,1
I-265
O C CH2CH3 CH3 c-C3H5 CH3 H 1,976 1 299,2
I-266
O C CH2CH3 CH3 CF3 CH3 H 1,927 1 327,1
I-267
O C CH2OCH3 CH3 CF3 CH3 H 0,776 2 343,0
I-268
O N CH3 CH3 CF3 CH3 H 9,0 (E+) 3
I-269
O N CH3 CH3 CF3 CH3 H 10,7 (E-) 3
I-270
O N CH3 CH3 c-C3H5 CH3 H 12,1 (E-) 4
I-271
O N CH3 CH3 c-C3H5 CH3 H 13,5 (E+) 4
Abreviaturas:
34
imagen28
imagen29
imagen30
B.10 Polilla de dorso de diamante (Plutella xilostella)
Se formularon los compuestos activos en agua:acetona 1:1 (vol:vol) y tensioactivo Alkamuls EL 620 al 0,1% (vol/vol). Se sumergió un disco de hoja de 6 cm de hojas de repollo en la disolución de prueba durante 3 segundos y se dejó secar al aire en una placa Petri revestida con papel de filtro húmedo. Se inocularon los discos de hoja con 10 larvas en el tercer estadio y se mantuvieron a 25-27ºC y una humedad relativa del 50-60% durante 3 días. Se evaluó la mortalidad tras 72 h de tratamiento.
Se demostró la actividad beneficiosa de los compuestos según la invención con respecto a compuestos cercanos estructuralmente conocidos de la técnica anterior mediante los siguientes experimentos comparativos:
Las tablas muestran el % de mortalidad en comparación con controles no tratados.
Compuestos
N.º I-32 N.º 7 de la tabla 14 en el documento WO10/034737
Pruebas / conc.
B.1 / 0,3 ppm
100% 0%
B.2 / 3 ppm
90% 25%
Compuestos
N.º I-32 N.º 5 de la tabla 14 en el documento WO10/034737
Pruebas / conc.
B.1 / 1 ppm
100% 0%
B.2 / 500 ppm
75% 0%
Compuestos
N.º I-98 N.º 175 de la tabla 14 en el documento WO10/034737
Pruebas / conc.
B.1 / 0,3 ppm
75% 0%
B.2 / 0,1 ppm
95% 0%
B.5 / 0,1 ppm
95% 0%
Pruebas / conc.
N.º I-98 N.º 5 de la tabla 98 en el documento WO10/034737
B.3 / 3 ppm
75% 0%
B.10 / 500 ppm
25% de FD*) 100% FD*)
Pruebas / conc.
N.º I-159 N.º 5 de la tabla 98 en el documento WO10/034737
B.3 / 1 ppm
100% 0%
B.8 / 500 ppm
75% 0%
Pruebas / conc.
N.º I-162 N.º 5 de la tabla 98 en el documento WO10/034737
B.3 / 1 ppm
100% 0%
B.8 / 500 ppm
63% 0%
Pruebas / conc.
N.º I-264 N.º 173 en el documento WO09/027393
B.3 / 10 ppm
75% 25%
38
imagen31

Claims (282)

  1. imagen1
  2. 10. Compuestos de fórmula I según la reivindicación 1, que se seleccionan de la siguiente lista:
    N.º
    T U R1 R2 R3 R4 R5
    1.
    O N H CH3 -CH2CH2- H
  3. 2.
    O N H CH3 CH2S(O)2CH3 CH3 CH3
  4. 3.
    O N CH3 CH3 CH2S(O)2CH3 CH3 CH3
  5. 4.
    O N H CH3 CH2OCH3 CH3 H
  6. 5.
    O N CH3 CH3 CH2OCH3 CH3 H
  7. 6.
    O N CH2CH3 CH3 -(CH2)4- H
  8. 7.
    O N CH3 CH3 -(CH2)4- H
  9. 8.
    O N H CH3 -(CH2)4- H
  10. 9.
    O N H CH3 CH2CH3 CH3 H
  11. 10.
    O N CH2CH3 CH3 CH2CH3 CH3 H
  12. 11.
    O N CH3 CH3 CH2CH3 CH3 H
  13. 12.
    O N H CH3 -(CH2)5- H
  14. 13.
    O N CH3 CH3 -(CH2)5- H
  15. 14.
    O N CH2CH3 CH3 -(CH2)5- H
  16. 15.
    O N CH2CH3 CH3 -(CH2)3- H
  17. 16.
    O N CH3 CH3 -(CH2)3- H
  18. 17.
    O N CH3 CH3 CH2C(CH3)2OCH3 CH3 H
  19. 18.
    O N CH2CH3 CH3 CH2C(CH3)2OCH3 CH3 H
  20. 19.
    O N H CH3 -(CH2)3- H
  21. 20.
    O N H CH3 CH2C(CH3)2OCH3 CH3 H
  22. 21.
    O N H CH3 -CH2CH2OCH2CH2- H
  23. 22.
    O N CH2CH3 CH3 -CH2CH2OCH2CH2- H
  24. 23.
    O N CH3 CH3 -CH2CH2OCH2CH2- H
  25. 24.
    O N CH2OCH2CH3 CH3 c-C3H5 CH3 H
  26. 25.
    O N H CH3 CH2OCH3 CH3 CH3
  27. 26.
    O N CH3 CH3 CH2OCH3 CH3 CH3
  28. 27.
    O N CH2OCH2CH3 CH3 CF3 CH3 H
  29. 28.
    O N CH3 CH3 CF2CHFCF3 CH3 H
  30. 29.
    O N CH3 CH3 CF2CHF2 CH3 H
  31. 30.
    O N H CH3 CF2CHFCF3 CH3 H
  32. 31.
    O N H CH3 CF2CHF2 CH3 H
  33. 32.
    O N H CH3 CN CH3 CH3
  34. 33.
    O N CH3 CH3 CN CH3 CH3
  35. 34.
    O N H CH3 CF3 CF3 H
  36. 35.
    O N H CH3 CN CH3 H
  37. 36.
    O N CH3 CH3 CN CH3 H
  38. 37.
    O N CH2CH3 CH3 CF3 CF3 H
  39. 38.
    O N CH3 CH3 CF3 CF3 H
  40. 39.
    O N H CH3 1-F-c-C3H4 CH3 H
  41. 40.
    O N CH3 CH3 1-F-c-C3H4 CH3 H
  42. 41.
    O N H CH3 C(CH3)3 CH3 H
  43. 42.
    O N CH3 CH3 C(CH3)3 CH3 H
  44. 43.
    O N CH2OCH3 CH3 C(CH3)3 CH3 H
  45. 44.
    O C H CH3 C(CH3)3 CH3 H
  46. 45.
    O C CH3 CH3 C(CH3)3 CH3 H
  47. 46.
    O N CH2CH3 CH3 C(CH3)3 CH3 H
  48. 47.
    O N H CH3 CH2CH3 CH2CH3 H
  49. 48.
    O N CH3 CH3 CH2CH3 CH2CH3 H
  50. 49.
    O N CH2OCH3 CH3 CH2CH3 CH2CH3 H
  51. 50.
    O C H CH3 CH2CH3 CH2CH3 H
  52. 51.
    O C CH3 CH3 CH2CH3 CH2CH3 H
  53. 52.
    O N H CF3 CH2CH3 CH2CH3 H
  54. 53.
    O N CH3 CF3 CH2CH3 CH2CH3 H
  55. 54.
    O N CH2OCH3 CF3 CH2CH3 CH2CH3 H
  56. 55.
    O C H CF3 CH2CH3 CH2CH3 H
  57. 56.
    O N H CF3 C(CH3)3 CH3 H
  58. 57.
    O N CH3 CF3 C(CH3)3 CH3 H
  59. 58.
    O N CH2OCH3 CF3 C(CH3)3 CH3 H
  60. 59.
    O C H CF3 C(CH3)3 CH3 H
  61. 60.
    O C CH2OCH2CH3 CH3 c-C3H5 CH3 H
    N.º
    T U R1 R2 R3 R4 R5
  62. 61.
    S C CH3 CH3 CF3 CH3 H
  63. 62.
    S C CH2CH3 CH3 c-C3H5 CH3 H
  64. 63.
    S C H CH3 CF3 CH3 H
  65. 64.
    S C CH2CH3 CH3 CF3 CH3 H
  66. 65.
    O N H CH3 -CCl2CH2- H
  67. 66.
    O N CH3 CH3 -CCl2CH2- H
  68. 67.
    O C CH2OCH2CH3 CH3 CF3 CH3 H
  69. 68.
    O N H CH3 CH=CH2 CH3 H
  70. 69.
    O N CH3 CH3 CH=CH2 CH3 H
  71. 70.
    O N CH2CH3 CH3 CH=CH2 CH3 H
  72. 71.
    O N CH2OCH3 CH3 CH=CH2 CH3 H
  73. 72.
    O C CH3 CF3 CH2CH3 CH2CH3 H
  74. 73.
    O N CH3 CH3 -CH2CH2N(CH3)CH2CH2- H
  75. 74.
    O N H CH3 CH2CN CH3 H
  76. 75.
    O N CH3 CH3 CH2CN CH3 H
  77. 76.
    O N CH2CH3 CH3 CH2CN CH3 H
  78. 77.
    O N CH2OCH3 CH3 CH2CN CH3 H
  79. 78.
    O C CH2CH3 CH3 CH2CN CH3 H
  80. 79.
    O N CH2CH3 CH3 CF3 CH3 CH3
  81. 80.
    O N H CH3 CF3 CH3 CH3
  82. 81.
    O C CH3 CH3 CF3 CH3 CH3
  83. 82.
    O N H CH3 -(CH2)5- CN
  84. 83.
    O C H CH3 CF3 CH3 CH3
  85. 84.
    O C CH3 CH3 -(CH2)5- CN
  86. 85.
    O N CH3 CH3 CF3 CH3 CH3
  87. 86.
    O C CH2CH3 CH3 CF3 CH3 CH3
  88. 87.
    O N CH2OCH2CH3 CH3 CF3 CH3 CH3
  89. 88.
    O N CH2OCH3 CH3 CF3 CH3 CH3
  90. 89.
    O N H CH3 -CH2CH2N(CH3)CH2CH2- H
  91. 90.
    O C H CH3 -CH2CH2N(CH3)CH2CH2- H
  92. 91.
    O C CH2OCH3 CH3 CF3 CH3 CH3
  93. 92.
    O N CH3 CH3 1-CN-c-C3H4 CH3 H
  94. 93.
    O N H CH3 1-CN-c-C3H4 CH3 H
  95. 94.
    O C H CH3 CH2CN CH3 H
  96. 95.
    O N H CH3 CH(CH3)2 CH3 H
  97. 96.
    O N CH3 CH3 CH(CH3)2 CH3 H
  98. 97.
    O N CH2OCH3 CH3 CH(CH3)2 CH3 H
  99. 98.
    O N CH2CH3 CH3 CH(CH3)2 CH3 H
  100. 99.
    O C H CH3 CH(CH3)2 CH3 H
  101. 100.
    O C CH3 CH3 CH(CH3)2 CH3 H
  102. 101.
    O C CH2CH3 CH3 CH(CH3)2 CH3 H
  103. 102.
    O N H CH3 CF3 CH2CH3 H
  104. 103.
    O N CH3 CH3 CF3 CH2CH3 H
  105. 104.
    O N CH2CH3 CH3 CF3 CH2CH3 H
  106. 105.
    O N CH2OCH3 CH3 CF3 CH2CH3 H
  107. 106.
    O C H CH3 CF3 CH2CH3 H
  108. 107.
    O C CH3 CH3 CF3 CH2CH3 H
  109. 108.
    O C CH2CH2OCH3 CH3 CF3 CH2CH3 H
  110. 109.
    O C CH3 CH3 CH2CN CH3 H
  111. 110.
    O N CH3 CH3 -(CH2)5- CF3
  112. 111.
    O N CH2CH3 CH3 -(CH2)5- CF3
  113. 112.
    O N H2OCH2CH3 CH3 -(CH2)5- CF3
  114. 113.
    O N CH2OCH3 CH3 -(CH2)5- CF3
  115. 114.
    O N H CH3 -(CH2)5- CF3
  116. 115.
    O C CH2OCH2CH3 CH3 CF3 CH3 CH3
  117. 116.
    O C H CH3 -(CH2)5- CF3
  118. 117.
    O C CH3 CH3 -(CH2)5- CF3
  119. 118.
    O C CH2CH3 CH3 -(CH2)5- CF3
  120. 119.
    O N CH2CH3 CH3 -CH2CH2OCH2CH2- CF3
  121. 120.
    O N CH3 CH3 -CH2CH2OCH2CH2- CF3
  122. 121.
    O N H CH3 -CH2CH2OCH2CH2- CF3
  123. 122.
    O C CH3 CH3 -CH2CH2OCH2CH2- CF3
    N.º
    T U R1 R2 R3 R4 R5
  124. 123.
    O C H CH3 -CH2CH2OCH2CH2- CF3
  125. 124.
    O N H CH3 CH2CH2OCH3 CH3 H
  126. 125.
    O N CH3 CH3 CH2CH2OCH3 CH3 H
  127. 126.
    O C H CH3 CH2CH2OCH3 CH3 H
  128. 127.
    O C CH3 CH3 CH2CH2OCH3 CH3 H
  129. 128.
    O C CH2CH3 CH3 CH2CH2OCH3 CH3 H
  130. 129.
    O N CH2CH3 CH3 CH2CH2OCH3 CH3 H
  131. 130.
    O N CH3 CH3 -(CH2)5- CN
  132. 131.
    O C CH2CH3 CH3 -(CH2)5- CN
  133. 132.
    O N H CH3 CH2F CH3 H
  134. 133.
    O N CH3 CH3 CH2F CH3 H
  135. 134.
    O N CH2CH3 CH3 CH2F CH3 H
  136. 135.
    O C CH2CH3 CH3 CH2F CH3 H
  137. 136.
    O C H CH3 CH2F CH3 H
  138. 137.
    O C CH3 CH3 CH2F CH3 H
  139. 138.
    O C H CH3 -(CH2)5- CN
  140. 139.
    O N CH2CH3 CH3 -(CH2)5- CN
  141. 140.
    O N H CH3 CHFCH3 CH3 H
  142. 141.
    O N CH3 CH3 CHFCH3 CH3 H
  143. 142.
    O N CH2CH3 CH3 CHFCH3 CH3 H
  144. 143.
    O C H CH3 CHFCH3 CH3 H
  145. 144.
    O C CH3 CH3 CHFCH3 CH3 H
  146. 145.
    O C CH2CH3 CH3 CHFCH3 CH3 H
  147. 146.
    O N H CH3 CHFCH3 CH3 H
  148. 147.
    O N CH3 CH3 CHFCH3 CH3 H
  149. 148.
    O N CH2CH3 CH3 CHFCH3 CH3 H
  150. 149.
    O C H CH3 CHFCH3 CH3 H
  151. 150.
    O C CH3 CH3 -CH2CH2OCH2CH2- CF3
  152. 151.
    O C CH2CH3 CH3 -CH2CH2OCH2CH2- CF3
  153. 152.
    O N CH2CH3 CH3 CN CH3 CH3
  154. 153.
    O N CH3 CH3 -CH2CH2- CN
  155. 154.
    O N H CH3 -CH2CH2- CN
  156. 155.
    O N CH2CH3 CH3 -CH2CH2- CN
  157. 156.
    O C CH2CH3 CH3 CHFCH3 CH3 H
  158. 157.
    O C CH3 CH3 CHFCH3 CH3 H
  159. 158.
    O C CH2CH3 CH3 CN CH3 CH3
  160. 159.
    O N CH2CH3 CH3 1-CN-c-C3H4 CH3 H
  161. 160.
    O N H CH3 CHF2 CH3 H
  162. 161.
    O N CH3 CH3 CHF2 CH3 H
  163. 162.
    O N CH2CH3 CH3 CHF2 CH3 H
  164. 163.
    O C H CH3 CHF2 CH3 H
  165. 164.
    O C CH2CH3 CH3 CHF2 CH3 H
  166. 165.
    O C CH3 CH3 CHF2 CH3 H
  167. 166.
    O C CH3 CH3 -CH2S(O)2CH2- H
  168. 167.
    O C CH2CH3 CH3 -CH2S(O)2CH2- H
  169. 168.
    O N CH3 CH3 -CH2CH2N[C(O)CH3]CH2CH2- H
  170. 169.
    O N CH2CH3 CH3 -CH2S(O)2CH2- H
  171. 170.
    O C H CH3 -CH2S(O)2CH2- H
  172. 171.
    O N H CH3 -CH2S(O)2CH2- H
  173. 172.
    O N CH3 CH3 -CH2S(O)2CH2- H
  174. 173.
    O N CH3 CH3 -CH2SCH2- H
  175. 174.
    O N H CH3 -CH2SCH2- H
  176. 175.
    O C H CH3 -CH2SCH2- H
  177. 176.
    O C CH3 CH3 -CH2SCH2- H
  178. 177.
    O C CH2CH3 CH3 -CH2SCH2- H
  179. 178.
    O N CH3 CH3 CH(CH3)2 CH(CH3)2 H
  180. 179.
    O N H CH3 CH(CH3)2 CH(CH3)2 H
  181. 180.
    O C H CH3 CH(CH3)2 CH(CH3)2 H
  182. 181.
    O C CH3 CH3 CH(CH3)2 CH(CH3)2 H
  183. 182.
    O C CH2CH3 CH3 CH(CH3)2 CH(CH3)2 H
  184. 183.
    O N CH2CH3 CH3 CH(CH3)2 CH(CH3)2 H
  185. 184.
    O N CH2CH3 CH3 -CH2SCH2- H
    N.º
    T U R1 R2 R3 R4 R5
  186. 185.
    O N H CH3 -CH2S(O)CH2- H
  187. 186.
    O N CH3 CH3 -CH2S(O)CH2- H
  188. 187.
    O C CH3 CH3 CN CH3 CH3
  189. 188.
    O C H CH3 CN CH3 CH3
  190. 189.
    O N CH2CH3 CH3 -CH2S(O)CH2- H
  191. 190.
    O C H CH3 -CH2S(O)CH2- H
  192. 191.
    O N H CH3 CH(CH2CH3)CH(CH3)2 CH3 H
  193. 192.
    O N CH3 CH3 CH(CH2CH3)CH(CH3)2 CH3 H
  194. 193.
    O N CH2CH3 CH3 CH(CH2CH3)CH(CH3)2 CH3 H
  195. 194.
    O C H CH3 CH(CH2CH3)CH(CH3)2 CH3 H
  196. 195.
    O C CH3 CH3 CH(CH2CH3)CH(CH3)2 CH3 H
  197. 196.
    O C CH2CH3 CH3 CH(CH2CH3)CH(CH3)2 CH3 H
  198. 197.
    O N H CH3 CH2CH(CH3)2 CH3 H
  199. 198.
    O N CH3 CH3 CH2CH(CH3)2 CH3 H
  200. 199.
    O N CH2CH3 CH3 CH2CH(CH3)2 CH3 H
  201. 200.
    O C H CH3 CH2CH(CH3)2 CH3 H
  202. 201.
    O C CH3 CH3 CH2CH(CH3)2 CH3 H
  203. 202.
    O C CH2CH3 CH3 CH2CH(CH3)2 CH3 H
  204. 203.
    O N H CH3 CF3 CH(CH3)2 H
  205. 204.
    O N CH3 CH3 CF3 CH(CH3)2 H
  206. 205.
    O N CH2CH3 CH3 CF3 CH(CH3)2 H
  207. 206.
    O C H CH3 CF3 CH(CH3)2 H
  208. 207.
    O C CH3 CH3 CF3 CH(CH3)2 H
  209. 208.
    O C CH2CH3 CH3 CF3 CH(CH3)2 H
  210. 209.
    O C CH2CH3 CH3 CF3 c-C3H5 H
  211. 210.
    O N H CH3 CF3 c-C3H5 H
  212. 211.
    O N CH3 CH3 CF3 c-C3H5 H
  213. 212.
    O N CH2CH3 CH3 CF3 c-C3H5 H
  214. 213.
    O C H CH3 CF3 c-C3H5 H
  215. 214.
    O C CH3 CH3 CF3 c-C3H5 H
  216. 215.
    O N H CH3 1-S(O)2CH3-c-C3H4 CH3 H
  217. 216.
    O N CH3 CH3 1-S(O)2CH3-c-C3H4 CH3 H
  218. 217.
    O N CH2CH3 CH3 1-S(O)2CH3-c-C3H4 CH3 H
  219. 218.
    O C H CH3 1-S(O)2CH3-c-C3H4I CH3 H
  220. 219.
    O C CH3 CH3 1-S(O)2CH3-c-C3H4I CH3 H
  221. 220.
    O C CH2CH3 CH3 1-S(O)2CH3-c-C3H4 CH3 H
  222. 221.
    O C CH3 CF3 C(CH3)3 CH3 H
  223. 222.
    O N H CH3 1-CH3-c-C3H4 CH3 H
  224. 223.
    O N CH2CH3 CH3 1-CH3-c-C3H4 CH3 H
  225. 224.
    O C H CH3 1-CH3-c-C3H4 CH3 H
  226. 225.
    O C CH3 CH3 1-CH3-c-C3H4 CH3 H
  227. 226.
    O N CH3 CH3 2,2-Cl2-c-C3H3 CH3 H
  228. 227.
    O N H CH3 -CH2CH2N[C(O)CH3]CH2CH2- H
  229. 228.
    O N H CH3 C(CH3)2CN CH3 H
  230. 229.
    O N CH3 CH3 C(CH3)2CN CH3 H
  231. 230.
    O N CH2CH3 CH3 C(CH3)2CN CH3 H
  232. 231.
    O N CH2CH3 CH3 CH2CF3 CH3 H
  233. 232.
    O N H CH3 CH2CF3 CH3 H
  234. 233.
    O N CH3 CH3 1-CH3-c-C3H4 CH3 H
  235. 234.
    O C CH3 CH3 2,2-Cl2-c-C3H3 CH3 H
  236. 235.
    O N CH2CH3 CH3 2,2-Cl2-c-C3H3 CH3 H
  237. 236.
    O C CH2CH3 CH3 2,2-Cl2-c-C3H3 CH3 H
  238. 237.
    O N H CH3 2,2-Cl2-c-C3H3 CH3 H
  239. 238.
    O N CH3 CH3 CH2CF3 CH3 H
  240. 239.
    O N H CH3 1-SCH3-c-C3H4 CH3 H
  241. 240.
    O N CH3 CH3 1-SCH3-c-C3H4 CH3 H
  242. 241.
    O N CH2CH3 CH3 1-SCH3-c-C3H4 CH3 H
  243. 242.
    O C H CH3 1-SCH3-c-C3H4 CH3 H
  244. 243.
    O C CH3 CH3 1-SCH3-c-C3H4 CH3 H
  245. 244.
    O C CH2CH3 CH3 1-SCH3-c-C3H4 CH3 H
  246. 245.
    O C H CH3 2,2-Cl2-c-C3H3 CH3 H
  247. 246.
    O C CH2CH3 CH3 1-CH3-c-C3H4 CH3 H
    N.º
    T U R1 R2 R3 R4 R5
  248. 247.
    O N CH2CH3 CH3 CF3 C(CH3)3 H
  249. 248.
    O N CH3 CH3 CF3 C(CH3)3 H
  250. 249.
    O N H CH3 CF3 C(CH3)3 H
  251. 250.
    O N H CH3 1-CF3-c-C3H4 CH3 H
  252. 251.
    O N CH2CH3 CH3 1-CF3-c-C3H4 CH3 H
  253. 252.
    O N CH3 CH3 1-CF3-c-C3H4 CH3 H
  254. 253.
    O N H CH3 c-C3H5 CH3 H
  255. 254.
    O N CH3 CH3 c-C3H5 CH3 H
  256. 255.
    O N CH3 CH3 CF3 CH3 H
  257. 256.
    O N H CH3 CF3 CH3 H
  258. 257.
    O N CH2CH3 CH3 CF3 CH3 H
  259. 258.
    O N CH2OCH3 CH3 c-C3H5 CH3 H
  260. 259.
    O N CH2OCH3 CH3 CF3 CH3 H
  261. 260.
    O C CH3 CH3 c-C3H5 CH3 H
  262. 261.
    O C H CH3 c-C3H5 CH3 H
  263. 262.
    O C CH2OCH3 CH3 c-C3H5 CH3 H
  264. 263.
    O C H CH3 CF3 CH3 H
  265. 264.
    O C CH3 CH3 CF3 CH3 H
  266. 265.
    O C CH2CH3 CH3 c-C3H5 CH3 H
  267. 266.
    O C CH2CH3 CH3 CF3 CH3 H
  268. 267.
    O C CH2OCH3 CH3 CF3 CH3 H
  269. 268.
    O N CH3 CH3 CF3 CH3 H
  270. 269.
    O N CH3 CH3 CF3 CH3 H
  271. 270.
    O N CH3 CH3 c-C3H5 CH3 H
  272. 271.
    O N CH3 CH3 c-C3H5 CH3 H
  273. 11.
    Compuestos de fórmula I según la reivindicación 1. que se seleccionan de la siguiente lista:
  274. 12.
    Composición que comprende al menos un compuesto según una cualquiera de las reivindicaciones 1 a 11 y al menos un portador líquido y/o sólido inerte.
  275. 13.
    Composición agrícola para combatir plagas animales que comprende al menos un compuesto según cualquiera
    N.º
    T U R1 R2 R3 R4 R5
  276. 32.
    O N H CH3 CN CH3 CH3
  277. 98.
    O N CH2CH3 CH3 CH(CH3)2 CH3 H
  278. 159.
    O N CH2CH3 CH3 1-CN-c-C3H4 CH3 H
  279. 162.
    O C CH3 CH3 CHF2 CH3 H
  280. 264.
    O C CH3 CH3 CF3 CH3 H
    5 de las reivindicaciones 1 a 11 y al menos un portador aceptable líquido y/o sólido inerte y, si se desea, al menos un tensioactivo.
  281. 14. Método no terapéutico para combatir o controlar plagas de invertebrados, método que comprende poner en contacto dicha plaga o su fuente de alimentos, hábitat o lugar de incubación con una cantidad eficaz desde el punto de vista pesticida de al menos un compuesto según una cualquiera de las reivindicaciones 1 a 11.
    10 15. Método para proteger plantas en crecimiento frente al ataque o infestación por plagas de invertebrados, método que comprende poner en contacto una planta, o terreno o agua en el que está creciendo la planta, con una cantidad eficaz desde el punto de vista pesticida de al menos un compuesto según cualquiera de las reivindicaciones 1 a 11.
  282. 16. Semilla que comprende un compuesto según cualquiera de las reivindicaciones 1 a 11, o los enantiómeros, diastereómeros o sales del mismo, en una cantidad de desde 0,1 g hasta 10 kg por 100 kg de semilla.
    15 17. Uso de los compuestos según cualquiera de las reivindicaciones 1 a 11, para proteger plantas en crecimiento frente al ataque o infestación por plagas de invertebrados.
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KR101911974B1 (ko) 2018-10-25
MX2013010493A (es) 2013-10-01
US9439427B2 (en) 2016-09-13
CA2830138C (en) 2019-02-26
ES2574414T7 (es) 2024-11-15
BR112013024708A2 (pt) 2016-07-19
DK2699563T6 (da) 2024-08-19
BR112013024708B1 (pt) 2018-10-09
EP2699563A1 (en) 2014-02-26
ME02449B (me) 2016-09-20
TWI600651B (zh) 2017-10-01
JP5937199B2 (ja) 2016-06-22
HRP20160639T4 (hr) 2024-09-27
CA2830138A1 (en) 2012-10-26
PT2699563T (pt) 2016-07-14
PL2699563T6 (pl) 2024-07-29
MX354349B (es) 2018-02-27
US20140045690A1 (en) 2014-02-13
AR086474A1 (es) 2013-12-18
WO2012143317A1 (en) 2012-10-26
HRP20160639T1 (hr) 2016-07-01
ZA201308600B (en) 2015-08-26
DK2699563T3 (en) 2016-07-25
EP2699563B1 (en) 2016-04-06
RS54848B2 (sr) 2024-09-30
IL228345A (en) 2016-04-21
CN103492378A (zh) 2014-01-01
EA201301185A1 (ru) 2014-03-31
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RS54848B1 (sr) 2016-10-31
US20160050927A1 (en) 2016-02-25
JP2014517822A (ja) 2014-07-24
US9198422B2 (en) 2015-12-01
IL228345A0 (en) 2013-12-31
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AU2012244846A1 (en) 2013-11-07
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AU2012244846B2 (en) 2016-07-07
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UA110825C2 (uk) 2016-02-25
CN103492378B (zh) 2016-09-28

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