ES2593116T3 - Pesticidas - Google Patents

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ES2593116T3
ES2593116T3 ES09717433.8T ES09717433T ES2593116T3 ES 2593116 T3 ES2593116 T3 ES 2593116T3 ES 09717433 T ES09717433 T ES 09717433T ES 2593116 T3 ES2593116 T3 ES 2593116T3
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esims
methyl
solid
oxide
sulfanylidene
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Inventor
Nneka Breaux
Michael Loso
Timothy Johnson
Jonathan Babcock
Benjamin Nugent
Timothy Martin
Annette Brown
Ronald Ross
William Lo
Matthias Ober
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Corteva Agriscience LLC
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Dow AgroSciences LLC
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms
    • 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • 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
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

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

Abstract

Un compuesto seleccionado del grupo que consiste en **Fórmula**

Description

imagen1
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63
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y 64
imagen24
Adicionalmente en la presente se divulgan compuestos (que no son parte de la invención) que tienen la siguiente fórmula general
6
imagen25
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imagen27
imagen28
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imagen34
imagen35
Paso B. Preparación de N-(metil(óxido){1-[6-(trifluorometil)piridin-3-il]etil}-λ4-sulfanilideno)-N'-piridin-3-iltiourea (4).
imagen36
En un matraz de fondo redondo de 50 mL cargado con una barra de agitación magnética se disolvió 5-[1(metilsulfonimidoil)etil]-2-(trifluorometil)piridina (0,200 g, 0,793 mmol) en THF (4,17 mL) y DMF (0,83 mL) a 25ºC. A 5 continuación, se agregó 3-isotiocianatopiridina (0,132 mL, 1,11 mmol) al matraz de reacción. Luego de la adición, la reacción se entibió hasta alcanzar 80ºC durante 12 h. Al completarse la reacción, la mezcla se diluyó con acetato de etilo y salmuera. Las capas se separaron y la capa acuosa se extrajo con acetato de etilo. Los extractos orgánicos se combinaron y se lavaron con salmuera, se secaron (Na2SO4), se filtraron y se concentraron al vacío. El material bruto se purificó utilizando HPLC en fase inversa eluyendo con mezclas de acetonitrilo-agua para proporcionar N
10 (metil(óxido){1-[6-(tufluorometil)piridin-3-il]etil}-λ4-sulfanilideno)-N'-piridin-3-iltiourea (4) como un sólido blanco (0,191 g, 62%): pf 92-94ºC; 1H NMR (400 MHz, CDCl3) δ (mezcla de diastereómeros) 8,82 y 8,76 (s, 1H), 8,5 (m, 2H), 8,07 (m, 2H), 7,74 (m, 1H), 7,30 (m, 1H), 5,89 y 5,61 (m, 1H), 3,55 y 3,35 (s, 3H), 1,94 y 1,85 (m, 3H); ESIMS m/z 389 ([M+H]+).
Tabla 1: Compuestosinsecticidas (ejemplos comparativos)
Nº comp
Estructura Ruta Caracterización
5
imagen37 A sólido blanco; pf 167-169ºC; ESIMS m/z 418 ([M+H]+)
6
imagen38 A espuma amarilla clara; ESIMS m/z 340 ([M+H]+)
7
imagen39 A sólido blanco; pf 170-172ºC; ESIMS m/z 394 ([M+H]+)
8
imagen40 A aceite marrón claro; ESIMS mlz 392 ([M+H]+)
9
imagen41 A sólido amarillo; pf 105-107ºC; ESIMS m/z 534 ([M+H]+)
10
imagen42 A semi-sólido marrón claro; ESIMS m/z 398 ([M+H]+)
18
Nº comp
Estructura Ruta Caracterización
11
imagen43 A aceite amarillo dorado; ESIMS m/z 425 ([M+H]+)
12
imagen44 A semi-sólido naranja; ESIMS m/z 398 ([M+H]+)
13
imagen45 A semi-sólido blanco; ESIMS m/z 326 ([M+H]+)
14
imagen46 A sólido blanco; pf 153-155ºC; ESIMS m/z 354 ([M+H]+)
15
imagen47 A sólido blancuzco; pf 154-156ºC; ESIMS m/z 352 ([M+H]+)
16
imagen48 A semi-sólido amarillo claro; ESIMS m/z 450 ([M+H]+)
17
imagen49 A semi-sólido amarillo claro; ESIMS m/z 446 ([M+H]+)
18
imagen50 A semi-sólido amarillo claro; ESIMS mlz 406 ([M+H]+)
19
imagen51 A sólido blanco; ESIMS m/z 384 [M+H]+)
19
imagen52
Paso B. Preparación de N,N-dimetil-N'-(metil(óxido){1-[6-(trifluorometil)piridin-3-il]etil}-λ4-sulfanilideno)tiourea (23).
imagen53
Se disolvió N-(metil(óxido){1-[6-(trifluorometil)piridin-3-il]etil}-λ4-sulfanilideno)-1H-imidazol-1-carbotioamida (0,088 g,
0,243 mmol) en acetonitrilo (0,486 mL) con agitación a temperatura ambiente. La mezcla luego se enfrió en un baño
5 de hielo. A esta solución enfriada se agregó 40% dimetilamina en agua (0,031 mL, 0,243 mmol). Al completarse la
reacción, se retiraron todos los sólidos de la mezcla por filtración y el filtrado se concentró al vacío. El material bruto
remanente se disolvió nuevamente en acetato de etilo y se lavó con HCl 1 N y salmuera. La capa orgánica luego se
secó (Na2SO4), se filtró y se concentró al vacío para proporcionar N,N-dimetil-N'-(metil(óxido){1-[6
(trifluorometil)piridin-3-il]etil}-λ4-sulfanilideno)tiourea (23) como un aceite amarillo (0,044 g, 54%): 1H NMR (400 MHz, 10 CDCl3) δ (mezcla de diastereómeros) 8,83 (s, 1H), 8,08 (m, 1H), 7,74 (m, 1H), 5,97 y 5,73 (m, 1H), 3,52 y 3,41 (s,
3H), 3,34 y 3,25 (s, 3H), 3,26 y 3,03 (s, 3H), 1,92 y 1,81 (d, J = 7,3Hz, 3H); ESIMS mlz 340 ([M+H]+).
Tabla 2: Compuestosinsecticidas (ejemplos comparativos)
Nº comp
Estructura Ruta Caracterización
24
imagen54 B aceite marrón; ESIMS mlz 368 ([M+H]+)
25
imagen55 B aceite amarillo; ESIMS m/z 366 ([M+H]+)
26
imagen56 B aceite amarillo; ESIMS mlz 379 ([M+H]+)
27
imagen57 B aceite amarillo; ESIMS m/z 381 ([M+H]+)
B = Ruta utilizada en el Ejemplo 6
Ejemplo 7: Preparación de 9H-fluoren-9-ilmetil[(metil(óxido){[6-(trifluorometil)piridin-3-il]metil-λ415 sulfanilideno)amino]carbonotioilcarbamato (28) (ejemplo comparativo).
imagen58
Se sintetizó 9H-fluoren-9-ilmetil[(metil(óxido){[6-(trifluorometil)piridin-3-il]metil}-λ4sulfanilideno)amino]carbonotioilcarbamato (28) a partir de la correspondiente sulfoximida de acuerdo con el procedimiento descrito en el Ejemplo 4. El compuesto se aisló como espuma amarilla clara (14,6 g, 100%): pf 9220 97ºC; 1H NMR (300 MHz, DMSO-d6) δ 11,18 (s, 1H), 8,93 (s, 1H), 8,29 (d, J = 7,9 Hz, 1H), 7,98 (d, J = 8,2 Hz, 1H),
21
imagen59
imagen60
imagen61
Se sintetizó N-[[(6-cloropiridin-3-il)metil](metil)óxido-λ4-sulfanilideno]-N"-hidroxiguanidina (39) a partir de la correspondiente N-cianosulfoximina de acuerdo con el procedimiento descrito en el Ejemplo 17. El compuesto se aisló como un sólido blanco (0,184 g, 54%): pf 156-158ºC; 1H NMR (400 MHz, CDCl3) δ (mezcla de diastereómeros) 8,40 (s, 1H), 7,81 (m, 1H), 7,42 (m, 1H), 4,75 (m, 2H), 3,10 y 3,01 (s, 3H); ESIMS m/z 263 ([M+H]+)
5 Ejemplo 19: Preparación de N-[[1-(6-cloropiridin-3-il)-2-ciclopropiletil](metil)óxido-λ4-sulfanilideno]-N"hidroxiguanidina (40).
imagen62
Se sintetizó N-[[1-(6-Cloropiridin-3-il)-2-ciclopropiletil](metil)óxido-λ4-sulfanilideno]-N"-hidroxiguanidina (40) a partir de la correspondiente N-cianosulfoximina de acuerdo con el procedimiento descrito en el Ejemplo 17. El compuesto se
10 aisló como un semi-sólido amarillo claro (0,142 g, 34%): 1H NMR (400 MHz, CDCl3) δ (mezcla de diastereómeros) 8,47 (s, 1H), 7,91 (m, 1H), 7,41 (m, 1H), 3,04 y 2,94 (s, 3H), 2,43 y 2,31 (m, 1H), 2,00 (m, 2H), 0,45 (m, 3H), 0,14 (m, 2H); ESIMS mlz 317 ([M+H]+).
Ejemplo 20: Preparación de N-[[(3E)-4-cloro-1-(6-cloropiridin-3-il)but-3-enil](metil)óxido-λ4-sulfanilideno]-N"hidroxiguanidina (41).
imagen63
Se sintetizó N-[[(3E)-4-cloro-1-(6-cloropiridin-3-il)but-3-enil](metil)óxido-λ4-sulfanilideno]-N"-hidroxiguanidina (41) a partir de la correspondiente N-cianosulfoximina de acuerdo con el procedimiento descrito en el Ejemplo 17. El compuesto se aisló como un semi-sólido amarillo claro (0,182 g, 50%): 1H NMR (400 MHz, CDCl3) δ (mezcla de diastereómeros) 8,42 (m, 1H), 7,83 (m, 1H), 7,43 (m, 1H), 6,07 (m, 1H), 5,64 (m, 1H), 4,58 y 4,49 (m, 2H), 3,22 (m,
20 1H), 3,05 y 2,94 (s, 3H); ESIMS m/z 337 ([M+H]+).
Ejemplo 21: Preparación de N"-hidroxi-N-(metil(óxido){[6-(trifluorometil)piridin-3-il]metil}-λ4-sulfanilideno)guanidina (42).
imagen64
Se sintetizó N"-hidroxi-N-(metil(óxido){[6-(trifluorometil)piridin-3-il]metil}-λ4-sulfanilideno)guanidina (42) a partir de la
25 correspondiente N-cianosulfoximina de acuerdo con el procedimiento descrito en el Ejemplo 17. El compuesto se aisló como un sólido blanco (0,188 g, 56%): pf 118-120ºC; 1H NMR (400 MHz, CDCl3) δ (mezcla de diastereómeros) 8,74 (s, 1H), 8,04 (m, 1H), 7,77 (m, 1H), 4,34 (s, 2H), 3,14 y2,91 (s, 3H); ESIMSm/z 297 ([M+H]+).
Ejemplo 22: Preparación de N-[{2-ciclopropil-1-[6-(trifluorometil)piridin-3-il]etil}(metil)óxido-λ4-sulfanilidenol-N"hidroxiguanidina (43)
imagen65
imagen66
Tabla 3: Compuestosinsecticidas
Nº comp
Estructura Ruta Caracterización
47
imagen67 C aceite marrón; ESIMS m/z 431 ([M+H]+)
48
imagen68 C semi-sólido amarillo; ESIMS m/z 325 ([M+H]+)
49
imagen69 C semi-sólido amarillo claro; ESIMS m/z 339 ([M+H]+)
50
imagen70 C semi-sólido amarillo; ESIMS m/z 353 ([M+H]+)
51
imagen71 C semi-sólido amarillo claro; ESIMS m/z 365 ([M+H]+)
52
imagen72 C semi-sólido amarillo claro; ESIMS m/z 401 ([M+H]+)
53
imagen73 C aceite amarillo claro; ESIMS m/z 351 ([M+H]+)
54
imagen74 C aceite naranja; ESIMS m/z 371 ([M+H]+)
27
Nº comp
Estructura Ruta Caracterización
55
imagen75 C aceite marrón claro; ESIMS m/z 385 ([M+H]+)
56
imagen76 C aceite marrón claro; ESIMS m/z 401 ([M+H]+)
57
imagen77 C semi-sólido blanco; ESIMS m/z 559 ([M+H]+)
58
imagen78 C semi-sólido amarillo claro; ESIMS m/z 551 ([M+H]+)
59
imagen79 C aceite marrón; ESIMS m/z 357 ([M+H]+)
60
imagen80 C aceite naranja; ESIMS m/z 369 ([M+H]+)
61 (ejemplo comparativo)
imagen81 C aceite marrón; ESIMS m/z 367 ([M+H]+)
28
imagen82
imagen83
de los pulgones vivos por planta bajo un microscopio. La actividad insecticida semidió mediante el uso de la fórmula de corrección de Abbott: Control % corregido = 100 * (X – Y) / X donde X = No. de pulgones vivos en plantas de verificación con disolvente 5 Y = No. de pulgones vivos en plantas tratadas Tabla 4: Actividad insecticida
imagen84
Clasificación con respecto al pulgón verde del melocotonero en repollo (pulverización foliar)
Nº de comp.
200 ppm
1
C
2
C
3
A
4
B
5
B
6
A
7
A
8
A
9
A
10
A
11
A
12
A
13
A
14
A
15
A
16
A
17
A
18
A
19
A
20
B
21
B
22
A
31
imagen85
Clasificación con respecto al pulgón verde del melocotonero en repollo (pulverización foliar)
Nº de comp.
200 ppm
23
A
24
A
25
A
26
A
27
A
28
B
29
A
30
B
31
A
32
B
33
A
34
B
35
B
36
A
37
A
38
A
39
A
40
B
41
B
42
A
43
A
44
A
45
B
46
A
47
A
48
A
32
imagen86
Clasificación con respecto al pulgón verde del melocotonero en repollo (pulverización foliar)
Nº de comp.
200 ppm
49
A
50
A
51
A
52
A
53
A
54
A
55
A
56
A
57
B
58
A
59
A
60
A
61
A
62
A
63
A
64
B
65
C
66
A
67
B
Los compuestos N° 1-37, 61 y 65-67 representan ejemplos comparativos. En cada caso de la Tabla 4 la escala de clasificación es la siguiente:
Control % (o mortalidad)
Clasificación
80-100
A
Menos de 80
B
No evaluado
C
33
imagen87
imagen88
imagen89
imagen90
imagen91
imagen92
imagen93
imagen94
imagen95
imagen96
imagen97

Claims (1)

  1. REIVINDICACIONES
    1. Un compuesto seleccionado del grupo que consiste en
    38
    imagen1
    39
    imagen2
    40
    imagen3
    41
    imagen4
    42
    imagen5
    43
    imagen6
    44
    imagen7
    45
    45
    imagen8
    46
    imagen9
    47
    imagen10
    48
    imagen11
    49
    imagen12
    50
    imagen13
    51
    imagen14
    52
    imagen15
    46
    53
    imagen16
    54
    imagen17
    55
    imagen18
    56
    imagen19
    57
    imagen20
    58
    imagen21
    59
    imagen22
    47
    imagen23
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