ES2660132T3 - Compuestos de pirazol plaguicidas - Google Patents

Compuestos de pirazol plaguicidas Download PDF

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ES2660132T3
ES2660132T3 ES13728196.0T ES13728196T ES2660132T3 ES 2660132 T3 ES2660132 T3 ES 2660132T3 ES 13728196 T ES13728196 T ES 13728196T ES 2660132 T3 ES2660132 T3 ES 2660132T3
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alkyl
species
haloalkyl
spiro
pentyl
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Sebastian SÖRGEL
Daniel SÄLINGER
Christian Defieber
Jürgen LANGEWALD
Birgit GOCKEL
Egon Haden
Deborah L. Culbertson
Koshi Gunjima
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BASF SE
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    • 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
    • A—HUMAN NECESSITIES
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    • 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
    • A01N37/18—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 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—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 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • A—HUMAN NECESSITIES
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    • 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
    • A01N37/44—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 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • 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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    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/88—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 three ring hetero 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
    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring

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

Abstract

Un compuesto de pirazol de fórmula I, **(Ver fórmula)** en la que R1 es H, alquilo C1-C2, o alcoximetilo C1-C2; R2 es CH3, CH2F, CHF2, o CF3; R3 es un carbo- o heterociclo monoespiro o diespiro de 5 a 10 miembros, que puede contener 1 o 2 unidades estructurales de heteroátomo seleccionadas entre N-Rc, O, y S(O)k, siendo k 0, 1, o 2, cuyo carbo- o heterociclo está no sustituido o puede estar sustituido con 1, 2, 3, o 4 radicales Ra3; Ra1 es CN, NO2, C(O)NH2, C(S)NH2, alquilcarboniloxi C1-C2, alcoxi C1-C4, haloalcoxi C1-C2, alquiloxicarbonilo C1-C2, o S(O)nRb; Ra2 es halógeno o un grupo mencionado para Ra1; Ra3 es halógeno, alquilo C1-C2, haloalquilo C1-C2, alcoxi C1-C2-alquilo C1-C2, alquilideno C1-C2, >=O, >=S, >=NRb, >=NORb, >=NSRb, o un grupo mencionado para Ra1; n es 0, 1, o 2; Rb es H, alquilo C1-C2, haloalquilo C1-C2, cicloalquilo C3-C6, o alcoxi C1-C4, Rc es H, alquilo C1-C2, haloalquilo C1-C2, alquilcarbonilo C1-C2, o alcoxicarbonilo C1-C2; R4 es alquilo C1-C4 o haloalquilo C1-C4; o R3 y R4 junto con el átomo de carbono, al cual están unidos, forman un carbo- o heterociclo monoespiro o diespiro de 5 a 10 miembros, que puede contener 1 o 2 unidades estructurales de heteroátomo seleccionadas entre N-Rc, O, y S(O)k, siendo k 0 1 o 2, cuyo carbo- o heterociclo está no sustituido o puede estar sustituido con 1, 2, 3 o 4 radicales Ra3*; Ra3* es CN, haloalquilo C1-C2, alcoxi C1-C2-alquilo C1-C2, o alquilideno C1-C2; R5 es H, CH3, CN, F, OCH3, SCH3, CF3, OCF3, o SCF3; y los estereoisómeros, sales, tautómeros y N-óxidos de estos.

Description

imagen1
imagen2
imagen3
imagen4
R5 es preferiblemente H, o CN, especialmente H.
Los ejemplos de los compuestos de fórmula I de la tabla I incluyen sus tautómeros, mezclas racémicas, enantiómeros y diasteroésteres puros individuales y sus mezclas ópticamente activas.
En los compuestos I, R1 es en particular CH3 o C2H5. R2 es preferiblemente CH3, CHF2 o CF3.
5 En los compuestos I, la variable R3 es preferiblemente un carbociclo monoespiro o diespiro de 5, 6, 7, 8, 9 o 10 miembros que está no sustituido o sustituido por 1 o 2 radicales Ra3. Ra3, si está presente, preferiblemente está seleccionado entre ciano, haloalquilo C1-C2, alquilideno C1-C2 y alcoxi C1-C2-alquilo C1-C2. Los sustituyentes Ra3 están preferiblemente en la posición 1-o 4-, si el carbociclo es monosustituido y en la posición 4,4, si el carbociclo es disustituido. Más preferiblemente, R3 es espiro[2.2]pentilo, que está no sustituido o porta uno o dos radicales Ra3
Ra3
10 o 7-diespiro[2.0.1.2]-heptilo que está no sustituido o porta un radical . R3 incluso se selecciona más preferiblemente entre el grupo que consiste en espiro[2.2]pentilo (R3.1), 2-metileno-espiro[2.2]pentilo (R3.2), 1-CNespiro[2.2]pentilo (R3.3), 1-(CF3)-espiro[2.2]pentilo (R3.4), 4,4-(CH3)2-espiro[2.2]pentilo (R3.5), 4-CH3espiro[2.2]pentilo (R3.6), 4-(CF3)-espiro[2.2]pentilo (R3.7), 4-(CH2OCH3)-espiro[2.2]pentilo (R3.8), y 7diespiro[2.0.2.1]-heptilo (R3.9).
15 En los compuestos I, la variable R4 es preferiblemente CH3, C2H5, CHF2 o CF3.
Los compuestos específicos de esta realización se compilan en la tabla V a continuación.
Tabla V
No.
R1 R2 R3 R4 R5
V-1
H CH3 espiro [2.2] pentilo CH3 H
V-2
CH3 CH3 espiro [2.2] pentilo CH3 H
V-3
CH2 CH3 CH3 espiro [2.2] pentilo CH3 H
V-4
H CH3 1-CN-espiro [2.2] pentilo CH3 H
V-5
CH3 CH3 1-CN-espiro [2.2] pentilo CH3 H
V-6
CH2CH3 CH3 1-CN-espiro [2.2] pentilo CH3 H
V-7
H CH3 4,4-(CH3) 2-espiro [2.2] pentilo CH3 H
V-8
CH3 CH3 4,4-(CH3) 2-espiro [2.2] pentilo CH3 H
V-9
CH2CH3 CH3 4,4-(CH3) 2-espiro [2.2] pentilo CH3 H
V-10
H CH3 4-(CH2OCH3) -espiro [2.2] pentilo CH3 H
V-11
CH3 CH3 4-(CH2OCH3)-espiro [2.2] pentilo CH3 H
V-12
CH2CH3 CH3 4-(CH2OCH3)-espiro [2.2] pentilo CH3 H
V-13
H CH3 1-[C (= O) NH2] -espiro [2.2] pentilo CH3 H
V-14
CH3 CH3 1-[C (= O) NH2] -espiro [2.2] pentilo CH3 H
V-15
CH2CH3 CH3 1-[C(=O)NH2]-espiro[2.2]pentilo CH3 H
Los compuestos según la invención se pueden preparar análogamente a las rutas de síntesis descritas en los 20 documentos WO 2009/027393 y WO 2010/034737 según procedimientos estándar de química orgánica, por ejemplo, según la siguiente ruta de síntesis:
6
imagen5
imagen6
5
10
15
20
25
30
35
40
45
50
termitas (Isoptera), por ejemplo, Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes grassei, Termes natalensis, y Coptotermes formosanus;
cucarachas (Blattaria -Blattodea), por ejemplo, Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, y Blatta orientalis;
chinches, pulgones, saltahojas, moscas blancas, insectos de escala, cigarras (Hemiptera), por ejemplo, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Bre vicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzus persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasono via ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion a venae, Trialeurodes vaporariorum, Toxoptera aurantiiand, Viteus vitifolii, Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., y Arilus critatus;
hormigas, abejas, avispas, moscas de sierra (Hymenoptera), por ejemplo, Athalia rosae, Atta cephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Lasius niger, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus, Pheidole megacephala, Dasymutilla occidentalis, Bombus spp., Vespula squamosa, Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus,y Linepithema humile;
grillos, saltamontes, langostas (Orthoptera), por ejemplo, Acheta domestica, Gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Chortoicetes terminifera, y Locustana pardalina;
arachnoidea, tales como los arácnidos (Acarina), por ejemplo, de las familias Argasidae, Ixodidae y Sarcoptidae, tales como Amblyomma americanum, Amblyomma variegatum, Ambryomma maculatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Dermacentor andersoni, Dermacentor variabilis, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Ornithodorus moubata, Ornithodorus hermsi, Ornithodorus turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes o vis, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, y Eriophyidae spp. tales como Aculus schlechtendali, Phyllocoptrata oleivora y Eriophyes sheldoni; Tarsonemidae spp. Such as Phytonemus pallidus y Polyphagotarsonemus latus; Tenuipalpidae spp. tales como Brevipalpus phoenicis; Tetranychidae spp. tales como Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius y Tetranychus urticae, Panonychus ulmi, Panonychus citri, y Oligonychus pratensis; Araneida, por ejemplo, Latrodectus mactans, y Loxosceles reclusa;
pulgas (Siphonaptera), por ejemplo, Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans,y Nosopsyllus fasciatus,
pececito de plata, firebrat (Thysanura), por ejemplo, Lepisma saccharina y Thermobia domestica,
ciempiés (Chilopoda), por ejemplo, Scutigera coleoptrata,
milpiés (Diplopoda), por ejemplo, Narceus spp.,
tijeretas (Dermaptera), por ejemplo, forficula auricularia,
piojos (Phthiraptera), por ejemplo, Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus y Solenopotes capillatus.
Colémbolos (springtails), por ejemplo, Onychiurus ssp.
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También son apropiados para controlar nematodos: nemátodos parásitos de plantas tales como nemátodos del nudo de la raíz, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, y otras especies de Meloidogyne; nematodos formadores de quistes, Globodera rostochiensis y otras especies de Globodera; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, y otras especies de Heterodera; Nematodos de la agalla de la semilla especies de Anguina; nematodos foliares y del tallo, especies de Aphelenchoides; nematodos de aguijón, Belonolaimus longicaudatus y otras especies de Belonolaimus; nematodos del pino, Bursaphelenchus xylophilus y otras especies de Bursaphelenchus; nematodos de anillo, especies de Criconema, especies de Criconemella, especies de Criconemoides, especies de Mesocriconema; nematodos del tallo y del bulbo, Ditylenchus destructor, Ditylenchus dipsaci y otras especies de Ditylenchus; nematodos de punzón, especies de Dolichodorus; nematodos de espiral, Heliocotylenchus multicinctus y otras especies de Helicotylenchus; nematodos envolventes y de envoltura, especies de Hemicycliophora y especies de Hemicriconemoides; especies de Hirshmanniella; nematodos lanza, especies de Hoploaimus; nematodos falsos del nudo de la raíz, especies de Nacobbus; nematodos de aguja, Longidorus elongatus y
otras especies de Longidorus; nematodos de lesiones, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi y otras especies de Pratylenchus; nematodos excavadores, Radopholus similis y otras especies de Radopholus; nematodos reniformes, Rotylenchus robustus y otras especies de Rotylenchus; especies de Scutellonema; nematodos de raíz corta y gruesa, Trichodorus primitivus y otras especies de Trichodorus, especies de Paratrichodorus; nematodos atroáfidos, Tylenchorhynchus claytoni, Tylenchorhynchus dubius y otras especies de Tylenchorhynchus; nematodos de cítricos, especies de Tylenchulus; nematodos puñal, especies de Xiphinema; y otras especies de nematodos parásitos de las plantas;
También son útiles para controlar arácnidos (Arachnoidea), tales como ácaros (Acarina), por ejemplo de las familias Argasidae, Ixodidae y Sarcoptidae, tales como Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, y Eriophyidae spp. tales como Aculus schlechtendali, Phyllocoptrata oleivora y Eriophyes sheldoni; Tarsonemidae spp. tales como Phytonemus pallidus y Polyphagotarsonemus latus; Tenuipalpidae spp. tales como Brevipalpus phoenicis; Tetranychidae spp. tales como Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius y Tetranychus urticae, Panonychus ulmi, Panonychus citri, y oligonychus pratensis.
Las formulaciones se preparan de manera conocida (véanse, por ejemplo, los documentos de referencia US 3,060,084, EP-A 707 445 (para concentrados líquidos), Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, 147-48, Perry’s Chemical Engineer’s Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 y siguientes. WO 91/13546, US 4,172,714, US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701, US 5,208,030, GB 2,095,558, US 3,299,566, Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H., Grubemann, A., Formulation tech-nology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001, 2. D. A. Knowles, Chemistry and Technology of Agrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998 (ISBN 07514-0443-8), por ejemplo, extendiendo el compuesto activo con auxiliares apropiados para la formulación de agroquímicos, tales como solventes y/o portadores, si se desea, emulsionantes, surfactantes y dispersantes, conservantes, agentes antiespumantes, agentes anticongelantes, para formulación de tratamiento de semillas, también opcionalmente agentes gelificantes.
Ejemplos de solventes apropiados son agua, solventes aromáticos (por ejemplo, productos de Solvesso, xileno), parafinas (por ejemplo, fracciones de aceite mineral), alcoholes (por ejemplo, metanol, butanol, pentanol, alcohol bencílico), cetonas (por ejemplo, ciclohexanona, gamma-butirolactona), pirrolidonas (NMP (N-metil-pirrolidona), NOP (N-octil-pirrolidona), acetatos (diacetato de glicol), glicoles, dimetilamidas de ácidos grasos, ácidos grasos y ésteres de ácidos grasos. En principio, también se pueden utilizar las mezclas de solventes.
Los emulsionantes apropiados son emulsionantes no iónicos y aniónicos (por ejemplo, éteres de alcohol graso de polioxietileno, alquilsulfonatos y arilsulfonatos).
Ejemplos de dispersantes son licores residuales de lignina-sulfito y metilcelulosa.
Los surfactantes apropiados utilizados son sales de metales alcalinos, alcalinotérreos y de amonio de ácido lignosulfónico, ácido naftalenosulfónico, ácido fenolsulfónico, ácido dibutilnaftaleno sulfónico, alquilarilsulfonatos, alquilsulfatos, alquilsulfonatos, sulfatos de alcoholes grasos, ácidos grasos y éteres de glicol alcohol graso sulfatado., además de condensados de naftaleno sulfonado y derivados de naftaleno con formaldehído, condensados de naftaleno o de ácido naftalensulfónico con fenol y formaldehído, polioxietilen octilfenol éter, isooctilfenol etoxilado, octilfenol, nonilfenol, éteres de alquilfenol poliglicol, tributilfenil poliglicol éter, tri-estearilfenil poliglicol éter, alquil aril poliéter alcoholes, alcohol y alcoholes grasos condensados de óxido de etileno, aceite de ricino etoxilado, polioxietileno alquil éteres, polioxipropileno etoxilado, lauril alcohol poliglicol éter acetal, sorbitol ésteres, lignosulfito licores residuales y metilcelulosa.
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C-2
CH3 SP1 0.728 358.3
C-3
CH2CH3 SP1 0.798 372.2
C-4
CH3 SP2 0. 715 330.2
C-5
CH2CH3 SP2 0.747 344.2
C-6
H SP2 0.705 316.1
C-7
H espiro [2.2] pentan-5-ilo CH3 0.839 298.2
C-8
CH3 espiro [2.2] pentan-5-ilo CH3 0.842 312.2
C-9
CH3 5-cianoespiro [2.2] pentan-5-ilo CH3 0.727 337.2
C-10
H 5-cianoespiro [2.2] pentan-5-ilo CH3 0.726 323.2
C-11
CH2CH3 5-cianoespiro [2.2] pentan-5-ilo CH3 0.781 351.2
C-12
CH2CH3 espiro [2.2] pentan-5-ilo CH3 0.924 326.2
C-13
H 2-(metoximetil)espiro[2.2] pentan-5-ilo CH3 0.809 342.4
C-14
CH3 2-(metoximetil)espiro[2.2] pentan-5-ilo CH3 0.819 356.2
C-15
CH2CH3 2-(metoximetil)espiro[2.2] pentan-5-ilo CH3 0.861 370.2
Las siguientes pruebas pueden demostrar la eficacia de control de los compuestos de esta invención sobre plagas específicas. Sin embargo, la protección de control de plagas proporcionada por los compuestos, mezclas o composiciones no está limitada a estas especies. En ciertos casos, se encuentra que las combinaciones de un
5 compuesto de esta invención con otros compuestos o agentes de control de plagas de invertebrados exhiben efectos sinérgicos contra ciertas plagas importantes de invertebrados.
B.1 Pulgón de plantas de caupí (Aphis craccivora)
Los compuestos activos se formularon en 50:50 (vol: vol) de acetona: agua. La solución de prueba se preparó el día del uso. Las plantas de caupí en macetas colonizadas con 100-150 pulgones de diversas etapas se pulverizaron
10 después de que se había registrado la población de plagas. La reducción de la población se evaluó después de 24, 72 y 120 horas.
En esta prueba, los compuestos C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C -11, y C-12 respectivamente a 500 ppm mostraron al menos 75% de mortalidad en comparación con los controles no tratados.
B.2 Pulgón de algodón (Aphis gossypii, etapas de vida mixtas)
15 Los compuestos activos se formularon en ciclohexanona como una solución 10,0000 ppm suministrada en tubos ABgene® de 1.3 ml. Estos tubos se insertaron en un pulverizador electrostático automático equipado con una boquilla atomizadora y sirvieron como soluciones madre para las cuales se hicieron diluciones más bajas en 50% de acetona: 50% de agua (v/v). Se incluyó un surfactante no iónico (Kinetic®) en la solución a un volumen de 0.01% (v/v).
20 Las plantas de algodón en la etapa de cotiledón se infestaron con pulgones antes del tratamiento colocando una hoja fuertemente infestada de la colonia de pulgones principal en la parte superior de cada cotiledón. Se permitió que los pulgones se transfirieran durante la noche para lograr una infestación de 80-100 pulgones por planta y se eliminó la hoja huésped. Las plantas infestadas se pulverizaron a continuación mediante un pulverizador electrostático de plantas automatizado equipado con una boquilla pulverizadora atomizadora. Las plantas se secaron
25 en la campana extractora del pulverizador, se retiraron del pulverizador y luego se mantuvieron en una sala de crecimiento bajo iluminación fluorescente en un fotoperíodo de 24 horas a 25 °C y 20-40% de humedad relativa. La mortalidad de pulgones en las plantas tratadas, en relación con la mortalidad en las plantas de control no tratadas, se determinó después de 5 días.
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PL3300602T3 (pl) 2020-08-24
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IL235893A (en) 2017-08-31
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CN104703982A (zh) 2015-06-10
BR122019015109B1 (pt) 2020-04-07
ES2800288T3 (es) 2020-12-29
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CA2874382A1 (en) 2013-12-27
ZA201500363B (en) 2016-03-30
US20150150257A1 (en) 2015-06-04
MX2014015712A (es) 2015-09-04
EA026929B1 (ru) 2017-05-31
BR122019015104B1 (pt) 2020-04-07
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AU2013279540A1 (en) 2015-01-22
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BR122019015125B1 (pt) 2020-04-07
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EA201500020A1 (ru) 2015-08-31
UA114913C2 (uk) 2017-08-28
BR122019015118B1 (pt) 2020-04-07
AU2017239525A1 (en) 2017-10-26
CL2014003471A1 (es) 2015-05-15
US9474277B2 (en) 2016-10-25
EP3300602B1 (en) 2020-03-25
BR112014032078A2 (pt) 2017-06-27
WO2013189801A1 (en) 2013-12-27
JP6279563B2 (ja) 2018-02-14
JP2015525234A (ja) 2015-09-03
BR122019015105B1 (pt) 2020-04-07
EP3300602A1 (en) 2018-04-04
AR095356A1 (es) 2015-10-14
CA2874382C (en) 2020-08-25
BR122019015138B1 (pt) 2020-04-07
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JP2018070621A (ja) 2018-05-10
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