IT201800004120A1 - Esteri di composti eterociclici ad attività nematocida, loro composizioni agronomiche e relativo uso - Google Patents
Esteri di composti eterociclici ad attività nematocida, loro composizioni agronomiche e relativo uso Download PDFInfo
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- IT201800004120A1 IT201800004120A1 IT102018000004120A IT201800004120A IT201800004120A1 IT 201800004120 A1 IT201800004120 A1 IT 201800004120A1 IT 102018000004120 A IT102018000004120 A IT 102018000004120A IT 201800004120 A IT201800004120 A IT 201800004120A IT 201800004120 A1 IT201800004120 A1 IT 201800004120A1
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- 239000000203 mixture Substances 0.000 title claims description 49
- 230000009418 agronomic effect Effects 0.000 title claims description 14
- 239000005645 nematicide Substances 0.000 title claims description 13
- 150000002148 esters Chemical class 0.000 title claims description 11
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 6
- 230000000694 effects Effects 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 64
- -1 pyrrolyl-2-yl group Chemical group 0.000 claims description 49
- 239000002904 solvent Substances 0.000 claims description 14
- 241000244206 Nematoda Species 0.000 claims description 10
- 230000001069 nematicidal effect Effects 0.000 claims description 10
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
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- 238000000034 method Methods 0.000 claims description 7
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- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052760 oxygen Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 239000001301 oxygen Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
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- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
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- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
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- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000008511 vegetative development Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—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
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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
- A01N43/64—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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—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 three ring hetero atoms
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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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
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- C—CHEMISTRY; METALLURGY
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Description
“Esteri di composti eterociclici ad attività nematocida, loro composizioni agronomiche e relativo uso”
La presente invenzione riguarda nuovi composti eterociclici fluoroalchenilici di Formula (I)
La presente invenzione riguarda inoltre composizioni agronomiche che contengono detti composti di formula (I) e il loro uso per il controllo di nematodi nelle colture agricole.
STATO DELL’ARTE
Esteri di composti eterociclici fluoroalchenilici sono stati descritti in letteratura per uso come pesticidi e, in particolare, come nematocidi.
Tali composti sono costituiti da tre residui caratteristici: un eterociclo aromatico, un residuo –(CH2)n-COO- in cui n è un intero da 0 a 2 ed una catena fluoroalchenilica di formula generale –(CH2)m-CX=CF2 in cui m può variare da 1 a 6 e X è un atomo di idrogeno oppure un alogeno.
La domanda di brevetto JP2000/038379 descrive composti esteri di piridina sostituita in posizione 2, 3 o 4 con una catena fluoroalchenilica ed opportuni sostituenti sull’anello.
La domanda di brevetto JP2000/086636 riporta derivati pirazolici recanti la suddetta catena fluoroalchenilica.
Altri gruppi eterociclici quali il tiofen-2-il, il furan-2-il, la pirazin-2-il, la chinol-4-il oppure il pirrol-2-il sono descritti nella domanda JP2000/186073, sostituiti con la medesima catena fluoroalchenilica.
Tuttavia, tutti questi composti sono risultati poco soddisfacenti sotto il profilo dell’attività nematocida, in quanto non riescono a contenere in modo efficace l'attacco del parassita ed a ridurre la formazione di galle sull’apparato radicale della pianta.
Inoltre, in diversi casi, tali prodotti risultano fitotossici nei confronti di importanti colture agricole alle dosi che permettono di ottenere una buona attività nematocida, manifestando una significativa necrosi delle foglie e dello stelo.
DESCRIZIONE
La Richiedente ha ora sorprendentemente trovato nuovi esteri di composti eterociclici fluoroalchenilici che superano gli inconvenienti sopra evidenziati, essendo caratterizzati da una elevata attività nematocida anche a basse dosi e che, nel contempo, sono ben tollerati dalle colture agrarie.
Costituiscono pertanto oggetto della presente invenzione esteri di composti eterociclici aventi formula generale (I):
in cui:
- Het rappresenta un eterociclo aromatico da 5 a 10 termini, eventualmente benzocondensato, o eterobiciclico contenente eteroatomi scelti tra azoto, zolfo ed ossigeno; detto eterociclo essendo opzionalmente sostituito da uno o più gruppi Y scelti tra alogeno, C1-C6-alchile, C1-C6-aloalchile, C3-C6-cicloalchile, C4-C7-cicloalchilalchile, C1-C6-alcossile, C1-C6-aloalcossile, C1-C6-tioalcossile, C1-C6-tioaloalcossili, C1-C6-alchilsulfinile, C1-C6-alchilsulfonile, C1-C6-alcossicarbonile, C3-C6-cicloalcossicarbonile, ammino, N-C1-C6-alchilammino, N,N-C2-C12-dialchilammino, N-C1-C6-alcossicarbonilammino, N-C3-C6-cicloalchilammino, N,N-C6-C12-dicicloalchilammino, N-C3-C6-cicloalcossicarbonilammino, C1-C6-alchilamminocarbonile, C3-C6-cicloalchilamminocarbonile, un gruppo NR1R2CONR1-formile, C1-C6-alchilcarbonile, carbossile, ciano, un arile opzionalmente sostituito, un benzile, un eterociclico aromatico opzionalmente sostituito, penta- oppure esa-atomico, opzionalmente benzocondensato od eterobiciclico, contenente almeno un eteroatomo scelto tra ossigeno, zolfo, azoto, eventualmente ossidato a N-ossido; - n rappresenta un numero intero compreso tra 0 e 4;
- m rappresenta un numero intero compreso tra 1 e 6;
- X rappresenta un atomo di H o di fluoro;
- R1, R2 uguali o diversi tra loro rappresentano un atomo di idrogeno, un gruppo C1-C4 alchilico oppure un gruppo C3-C6- cicloalchilico,
con la condizione che:
se n assume il valore 1, X rappresenta un atomo di F per qualsiasi significato di Het e di m;
se Het rappresenta un gruppo tiofen-2-ile o un gruppo furan-2-ile o un gruppo pirazin-2-ile o un gruppo chinol-4-ile o pirrolil-2-ile sostituiti o non sostituiti da uno o più gruppi Y oppure Het rappresenta un gruppo pirazol-5-ile o un gruppo piridil-2-ile o piridil-3-ile o piridil-4-ile non sostituito o sostituito da uno o più gruppi Y scelti tra alogeno, C1-C6-alchile, C1-C6-alcossile, C1-C6-tioalcossile, C1-C6-tioaloalcossili, arile, oppure Het rappresenta un gruppo 1,2,3-tiadiazol-4-ile o un gruppo 1,2,3-tiadiazol-5-ile sostituiti o non sostituiti da uno o più gruppi Y, allora, contemporaneamente, n deve essere diverso da 0 e X diverso da H;
se Het rappresenta un gruppo pirazol-4-ile sostituito o non sostituito da uno o più gruppi Y, allora, contemporaneamente, n deve essere diverso da 1, m diverso da 1 e X diverso da F.
Esempi di Het sono: tiazolile, 1,3,4-tiazolile, pirimidile, imidazolile, indolile, benzotiazolile, benzofuranile, [1,2,4]-triazolo-[3,2-b]-tiazolile.
Esempi di alogeno sono: fluoro, cloro, bromo, iodio.
Esempi di alchile C1-C6, lineari o ramificati, sono metile, etile, n-propile, isopropile, n-butile, isobutile, sec-butile, tert-butile, n-pentile, 3-metilbutile, nesile, 3,3-dimetilbutile.
Esempi di aloalchile C1-C6 sono fluorometile, difluorometile, trifluorometile, clorometile, diclorometile, 2,2,2-trifluoroetile, 1,1,2,2-tetrafluoroetile, pentafluoroetile, eptafluoropropile, 4,4,4-tricloro-butile, 4,4-difluoropentile, 5,5-difluoroesile.
Esempi di alcossile C1-C6, lineari o ramificati, sono metossi, etossi, n-propossi, isopropossi, n-butossi, isobutossi, sec-butossi, tert-butossi, n-pentossi, 3-metilbutossi, esilossi, 3,3-dimetilbutossi.
Esempi di aloalcossile C1-C6 sono fluorometossi, difluorometossi, trifluorometossi, clorometossi, diclorometossi, 2,2,2-trifluoroetossi, 1,1,2,2-tetrafluoroetossi, 1,1,2,3,3,3-esafluoropropossi, 4,4,4-triclorobutossi, 4,4-difluoropentossi, 5,5-difluoroesilossi.
Esempi di cicloalchile C3-C6 sono ciclopropile, ciclobutile, ciclopentile, cicloesile. Esempi di alocicloalchile C3-C8 sono 2,2-dicloro-ciclopropile, 2,2-difluorociclopropile, 2,2,3,3-tetrafluorociclobutile, 3,3-difluorociclopentile, 2-fluorocicloesile.
Esempi di cicloalchilalchile C4-C7 sono metilciclopropile, metilciclopentile, etilciclopropile, metilcicloesile.
Per arile opzionalmente sostituito si intende un gruppo arilico che può avere uno o più sostituenti, uguali o diversi tra loro, scelti preferibilmente tra i seguenti gruppi: atomi di alogeno, C1-C6 alchili, C1-C6 aloalchili, C1-C6 alcossili, C1-C6 aloalcossili, C3-C6 cicloalcossili, C4-C7 cicloalchilalcossili, fenossili, C1-C6 alchiltio, C1-C6 aloalchiltio, C1-C6 alchilsulfinili, C1-C6 alchilsulfonili, C1-C6 alchilammino, C2-C12 dialchilammino, ciano, C2-C7 alcossicarbonili, benzilossicarbonili, fenossicarbonili.
Per eterociclo aromatico opzionalmente sostituito si intende un anello eterociclico penta- oppure esa-atomico, opzionalmente benzocondensato od eterobiciclico, contenente almeno un eteroatomo scelto tra azoto, ossigeno, zolfo e che può avere uno o più sostituenti, uguali o diversi tra loro, scelti preferibilmente tra i seguenti gruppi: atomi di alogeno, C1-C6 alchili, C1-C6 aloalchili, C1-C6 alcossili, C1-C6 aloalcossili, C3-C6 cicloalcossili, C4-C7 cicloalchilalcossili,, fenossili, C1-C6 tioalcossili, C1-C6 tioaloalcossili, C1-C6, alchilsulfinili, C1-C6 alchilsulfonili, ammino eventualmente sostituito da uno o due gruppi alchilici C1-C6, ciano, nitro, carbossile, C2-C5 alcossicarbonili, benzilossicarbonili, fenossicarbonili.
Esempi di gruppi eteroarilici sono: piridina, piridina N-ossido, pirimidina, piridazina, pirazina, furano, tiofene, pirrolo, ossazolo, tiazolo, isossazolo, isotiazolo, ossadiazolo, tiadiazolo, pirazolo, imidazolo, triazolo, indolo, benzofurano, benzotiofene, benzossazolo, benzotiazolo, benzossadiazolo, benzotiadiazolo, benzopirazolo, benzimidazolo, benzotriazolo, triazolopiridina, triazolopirimidina, tiazolo.
Si intendono rientrare nello spirito della presente invenzione anche:
a) tutti gli eventuali isomeri geometrici dei composti di formula generale (I); b) i sali dei composti di formula (I) ottenuti per addizione di acidi inorganici od organici;
c) eventuali forme idrate dei composti di formula (I).
Esempi specifici di composti di formula generale (I) preferiti per la loro attività nematocida sono i composti in cui Het, n, m, e X assumono i significati riportati in Tabella 1:
Tabella 1
Particolarmente preferiti sono i composti di formula generale (I) in cui Het, n, m e X assumono i significati riportati in Tabella 2.
Tabella 2
I composti di formula generale (I) possono essere preparati a partire dal corrispondente acido eterociclico di formula generale (II) per reazione di esterificazione con un opportuno alcool di formula generale (III) come riportato nello schema di reazione 1, secondo metodi ben noti in chimica organica.
Schema 1
Le condizioni di reazione prevedono l’impiego di un condensante quale ad esempio N,N-dicicloesilcarbodimmide, in presenza o assenza di un’ammina quale N,N-dimetilamminopiridina, in un solvente appropriato quale diclorometano, cloroformio, tetraidrofurano o diossano, ad una temperatura compresa tra 0°C e la temperatura di ebollizione del solvente, per un tempo compreso tra 1 e 72 ore. I composti di formula (I) possono anche essere ottenuti per reazione dell’acido di formula (II) con l’alcool di formula (III) in presenza di una catalisi acida, utilizzando ad esempio acido cloridrico o acido solforico come descritto in R.C. Larock “Comprehensive Organic Transformations” o ad esempio in F. T. Schevenels, M. Shen. A. Scott “J. American Chemical Society”, 2017, vol.139 pag. 6329-6337.
I composti di formula (I) possono ancora essere ottenuti per reazione di Mitsunobu tra l’acido di formula (II) e l’alcol di formula generale (III) in presenza di trifenilfosfina e dietilazodicarbossilato, in un solvente quale ad esempio tetraidrofurano, dietiletere o diossano, ad una temperatura compresa tra la temperatura ambiente e quella di riflusso del solvente, come descritto ad esempio in US 7601849 (2009).
Alternativamente i composti di formula (I) possono essere ottenuti mediante attivazione dell’acido carbossilico o via cloruro acilico o via anidride mista e successiva addizione dell’opportuno alcool di formula generale (III), secondo lo schema di reazione 2.
Schema 2
La reazione viene condotta facendo reagire un composto di formula (IV), dove Z rappresenta un atomo di cloro o un residuo OCOR1, con R1 che assume il significato di C1-C4 alchile, ottenuto dal composto di formula generale (II) mediante metodi noti in letteratura con un alcool di formula generale (III) in presenza di una base quale trietilammina o N-metil-morfolina o piridina, in un opportuno solvente quale cloruro di metilene o cloroformio o tetraidrofurano, ad una temperatura compresa tra 0°C e la temperatura di ebollizione del solvente, per un tempo compreso tra 1 e 72 ore, come ampiamente descritto in R.C. Larock “Comprehensive Organic Transformations” o ad esempio in US 2003/109563 (2003) o in US 2004/198702 (2004).
I composti di formula generale (I) possono ancora essere ottenuti da un opportuno sale dell’acido carbossilico di formula generale (V), sale di un metallo alcalino, quale sodio, litio o potassio o di ammonio, quale trimetilammonio o trietilammonio, in presenza di un derivato di formula (VI) dove K rappresenta un gruppo uscente quale un atomo di alogeno, scelto tra cloro, bromo o iodio o un gruppo trifluorometansolfonato o p-toluensolfonato, o metansolfonato secondo lo schema di reazione 3.
Schema 3
La reazione prevede la salificazione dell’acido carbossilico con una base quale bicarbonato di sodio, bicarbonato di potassio, carbonato di potassio, carbonato di sodio, idrossido di sodio, idrossido di potassio, idrossido di litio o sodio idruro o tbutilato di potassio in un solvente quale tetraidrofurano, N,N-dimetilformammide, N-metilpirrolidone, toluene o acetone e successiva addizione di un composto di formula (VI), ad una temperatura compresa tra la temperatura ambiente e quella di riflusso del solvente scelto, come ad esempio decritto in US 5519015 (1996).
I composti di formula (II), quando non sono commerciali, possono essere facilmente preparati secondo metodi noti in chimica organica, come descritto in R.C. Larock “Comprehensive Organic Transformations”.
I composti di formula (VI), per K che rappresenta un atomo di alogeno, sono prodotti commerciali.
In alternativa i composti di formula (VI), per K che rappresenta un gruppo trifluorometansolfonato, p-toluensolfonato o metansolfonato, possono essere ottenuti dai corrispondenti alcoli (III) secondo quanto descritto in Theodora W: Greene “Protective Groups in Organic Synthesis” Third Edition pag. 198-199 ed indicato nello schema 4.
Schema 4
(III) (VI)
I composti aventi formula generale (I), per particolari significati di Het, possono essere ottenuti sotto forma racemica o quali isomeri otticamente attivi.
Rientrano pertanto nello spirito della presente invenzione sia i composti aventi formula generale (I) isomericamente puri, sia miscele degli stessi, eventualmente ottenute durante la preparazione dei composti aventi formula generale (I) oppure derivati da una incompleta separazione degli isomeri stessi, in qualsivoglia proporzione.
Come detto, i composti di formula generale (I) sono dotati di una elevata attività nematocida e non manifestano alcuna fitotossicità nei confronti delle colture di applicazione rendendoli adatti all’impiego in campo agrario nella difesa dai nematodi.
E’ quindi ulteriore oggetto della presente invenzione l’uso dei composti di Formula (I) per il controllo di nematodi.
In particolare, i composti oggetto della presente invenzione sono efficaci nel controllo di numerosi nematodi quali ad esempio: Pratylenchus spp, Globodera spp, Heterodera spp, Meloidogyne spp, Aphelenchoides spp, Radopholus Similis, Ditylenchus Dipsaci, Tylenchulus Semipenetrans, Longidorus spp, Xiphinema spp, Trichodorus spp, Bursaphelenchus spp, Belonolaimus spp., ecc.
Più in particolare i composti di Formula (I) possono essere applicati in diversi momenti dello sviluppo vegetativo, ad esempio prima del trapianto/semina oppure durante la crescita della pianta, per via fogliare, oppure al suolo mediante fertirrigazione, oppure incorporazione al terreno, oppure tramite concia del seme.
I composti di Formula (I) sono in grado di esplicare un’azione nematocida a carattere sia curativo sia preventivo ed esibiscono una fitotossicità molto bassa o nulla sulle colture trattate.
Per gli impieghi pratici in agricoltura, è spesso vantaggioso utilizzare i composti della presente invenzione opportunamente formulati in composizioni agronomiche ad attività nematocida comprendenti uno o più composti di Formula (I), eventualmente anche come miscela di isomeri e coformulanti agronomicamente accettabili.
Sono quindi un ulteriore oggetto della presente invenzione composizioni agronomiche nematocide comprendenti uno o più composti di Formula (I), un solvente e/o diluente solido, liquido o liquefatto, eventualmente uno o più tensioattivi e altri coformulanti agronomicamente accettabili.
Si possono impiegare composizioni che si presentano sotto forma di polveri secche, polveri bagnabili, concentrati emulsionabili, microemulsioni, paste, granulati, soluzioni, sospensioni, fumiganti ecc.: la scelta del tipo di composizione dipenderà dall’impiego specifico.
Le composizioni sono preparate secondo metodologie note, per esempio diluendo o sciogliendo la sostanza attiva con un mezzo solvente e/o diluente solido, eventualmente in presenza di tensioattivi.
Come diluenti inerti solidi, o supporti, possono essere utilizzati caolino, allumina, silice, talco, bentonite, gesso, quarzo, dolomite, attapulgite, montmorillonite, terra di diatomee, cellulosa, amido, ecc.
Come diluenti inerti liquidi possono essere usati acqua, oppure solventi organici quali idrocarburi aromatici (xiloli, miscele di alchilbenzoli, ecc.), idrocarburi alifatici (esano, cicloesano, ecc.), idrocarburi aromatici alogenati (clorobenzolo, ecc.), alcoli (metanolo, propanolo, butanolo, ottanolo, ecc.), esteri (acetato di isobutile, ecc.), chetoni (acetone, cicloesanone, acetofenone, isoforone, etilamilchetone, ecc.), oppure oli vegetali o minerali o loro miscele, ecc.
Come diluenti liquefatti o sostanze liquefatte che gassificano a temperatura e pressione ambiente possono essere impiegati gas propellenti quali butano, propano, idrocarburi alogenati, azoto o biossido di carbonio.
Come tensioattivi possono essere utilizzati agenti bagnanti ed emulsionanti di tipo non-ionico (alchilfenoli polietossilati, alcoli grassi polietossilati, ecc.), anionico (alchilbenzen-solfonati, alchilsolfonati, ecc.), cationico (sali quaternari di alchilammonio, ecc.).
Possono inoltre essere aggiunti disperdenti (ad esempio lignina e suoi sali, derivati di cellulosa, alginati, ecc.), stabilizzanti (ad esempio antiossidanti, assorbenti dei raggi ultravioletti, ecc.).
La concentrazione di sostanza attiva nelle suddette composizioni può variare entro un ampio intervallo, a seconda del composto attivo, delle applicazioni a cui sono destinate, delle condizioni ambientali e del tipo di formulazione adottato. In generale, la concentrazione di sostanza attiva è preferibilmente compresa tra 0,1 e 90%, particolarmente preferita è quella compresa tra 0,5 e 90%.
I composti della presente invenzione, tal quali o formulati possono essere usati in miscela con altri principi attivi quali, ad esempio, erbicidi, fungicidi, battericidi, insetticidi, acaricidi, nematocidi, fertilizzanti, biostimolanti ecc. per ampliarne lo spettro o prevenire la resistenza.
In alcuni casi, le miscele così ottenute presentano un effetto sinergico tra i componenti, effetto che porta la miscela, ad esempio, ad esplicare una attività superiore rispetto a quella dei singoli elementi che la compongono.
Esempi di insetticidi, acaricidi, nematocidi che possono essere aggiunti alle composizioni contenenti uno o più composti di formula generale (I) sono i seguenti:
abamectin, acetamiprid, acrinathrin, alphacypermethrin, alphamethrin, azadirachtin, Bacillus subtilis, Bacillus thuringiensis, Beauveria bassiana, betacyfluthrin, bifenazate, bifenthrin, buprofezin, chlorpyrifos, chlorpyrifos M, clofentezine, cyhalothrin, cyhexatin, cypermethrin, cyromazine, chloropicrin, clorantranilipide, clotianidin, deltamethrin, diflubenzuron, dimethoat, dazonet, difluoruro di solforile, dimethyldisulfide, emamectin, esfenvalerate, ethoprophos, etofenprox, etoxazole, fenamiphos, fenazaquin, fenoxycarb, fenpyroximate, fipronil, fluazinam, fluensulfone, flufenoxuron, fluvalinate, fosthiazate, formentanate, flonicamid, formet, viruses, hexythiazox, imidaclopridi, indoxacarb, lambda-cyhalothrin, lufenuron malathion, metaldehyde, methamidophos, Metharhizium spp, methiocarb, methomyl, methoxyfenozide, milbemectin, metaflumizone, metam sodium, metam potassium, oxamyl, Paecilomyces fumosoroseus, phosmet, pirimicarb, pirimiphos M, pyrethrum, pyridaben, pyriproxyfen, piperonyl butoxide, spinosad, spironesifen, spirotetramat, spinetoran, spirodiclofen, tau-fluvalinate, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, thiacloprid, triflumuron, zeta-cypermethrin, (1R-cis)-[5-(fenilmetil)-3-furanil]-metil-3-[(diidro-2-osso-3(2H)-furanilidene) metil]-2,2-dimetilciclopropancarbossilato, (3-fenossifenil)-metil-2,2,3,3-tetrametil-ciclopropancarbossilato, 1-[(2-cloro-5-tiazolil)metil]-5-triazina 2-(1H)-immina, 2-(2-cloro-6-fluorofenil)-4-[4-(l,1-dimetiletil)fenil]-4,5-diidro-ossazolo, 2-(acetilossi)-3-dodecil-1,4-naftalenedione, 2-cloro-N-[[[4-(l-feniletossi)-fenil]-ammino]-carbonil]-benzammide, 2-cloro-N-[[[4-(2,2-dicloro-1,1-difluoroetossi)-fenil]-ammino]-carbonil]-benzammide, 3metilfenil-propilcarbammato, 4-[4-(4-etossifenil)-4-metilpentil]-l-fluoro-2-fenossibenzene, 4-cloro-2-(1,1-dimetiletil)-5-[[2-(2,6-dimetil-4-fenossifenossi) etil]tio]-3-(2H)-piridazinone, 4-cloro-2-(2-cloro-2-metilpropil)-5-[(6-iodo-3-piridinil)(2-cloro-2-metilpropil)-5-[(6-iodo-3-piridinil)-metossi]-3-(2H)piridazinone, 4-cloro-5-[(6-cloro-3-piridinil)metossi]-2-(3,4-diclorofenil)-3(2H)piridazinone, Bacillus thuringiensis strain EG-2348, acido [2-benzoil-1-(1,1-dimetiletil)-idrazino] benzoico, 2,2-dimetil-3-(2,4-diclorofenil)-2-osso-1-ossaspiro [4.5]-dec-3-en-4-il butanoato, [3-[(6-cloro-3-piridinil)-metil]-2-tiazolidinili-dene]-cianammide, diidro-2-(nitrometilene)-2H-1,3-tiazina-3(4H)-carbossaldeide, etil[2-[[1,6-diidro-6-osso-1-(fenilmetil)-4-piridazinil]ossi]etil]-carbammato, N-(3,4,4-trifluoro-1-osso-3-butenil)-glicina, N-(4-clorofenil)-3-[4-(difluorometossi)-fenil]-4,5-diidro-4-fenil-1H-pirazolo-1-carbossammide, N-[(2-cloro-5-tiazolil)metil]-N'-metil-N"-nitro-guanidina, N-metil-N'-(1-metil-2-propenil)-1,2-idrazinadicarbotioammide, N-metil-N'-2-propenil-1,2-idrazinadicarbotioammide, O,O-dietil[2-(dipropilammino)-2-ossoetil]-etilfosforoammidotioato.
Esempi di erbicidi che possono essere aggiunti alle composizioni contenenti uno o più composti di formula generale (I) sono i seguenti:
acetochlor, acifluorfen, aclonifen, AKH-7088 ({metil (E,Z)-[[[1-[2-cloro-4-(trifluorometil)fenossi]-2-nitrofenil]-2-metossietilidene]ammino]acetato}), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, amitrole, anilofos, asulam, atrazine, azafenidin, azimsulfuron, aziprotryne, BAY MKH 6561 (metil 2-({[(4-metil-5-osso-3-propossi-4,5-diidro-1H-1,2,4-triazol-1-il)carbonil] ammino}sulfonil)benzoato sale sodico), beflubutamid, benazolin, benfluralin, benfuresate, bensulfuron, bensulide, bentazone, benzfendizone, benzobicyclon, benzofenap, benzthiazuron, bifenox, bilanafos, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorbromuron, chlorbufam, chlorflurenol, chloridazon, chlorimuron, chlornitrofen, chlorotoluron, chloroxuron, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon ethyl, cinmethylin, cinosulfuron, clethodim, clodinafop, clomazone, clomeprop, clopyralid, cloransulam-methyl, cumyluron (JC-940), cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D, 2,4-DB, daimuron, dalapon, desmedipham, desmetryn, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclosulam, diethatyl, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dinitramine, dinoseb, dinoseb acetate, dinoterb, diphenamid, dipropetryn, diquat, dithiopyr, 1-diuron, eglinazine, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethidimuron, ethiozin (SMY 1500), ethofumesate, ethoxyfen-ethyl (HC-252), ethoxysulfuron, etobenzanid (HW 52), fenoxaprop, fenoxaprop-P, fentrazamide, fenuron, flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazolate (JV 485), flucarbazone-sodium, fluchloralin, flufenacet, flufenpyr ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, flumipropin, fluometuron, fluoroglycofen, fluoronitrofen, flupoxam, flupropanate, flupyrsulfuron, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine, furyloxyfen, glufosinate, glyphosate, halosulfuronmethyl, haloxyfop, haloxyfop-P-methyl, hexazinone, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, indanofan, iodosulfuron, ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, KPP-421, lactofen, lenacil, linuron, LS830556 (acido[[[2-metil(metilsulfonil)ammino]-2-ossoetil]ammino]metilfosfonico), MCPA (acido 2-metil-4-clorofenossiacetico), MCPA-tioetile, MCPB (acido 4-(4-cloro-2-metilfenossi)butanoico), mecoprop, mecoprop-P, mefenacet, mesosulfuron, mesotrione, metamitron, metazachlor, methabenzthiazuron, methazole, methoprotryne, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, molinate, monalide, monolinuron, naproanilide, napropamide, naptalam, NC-330 (metil 5-[(4,6-dimetilpirimidin-2-il)carbamoilsulfamoil]1-piridin-2-il pirazol-4-carbossilato), neburon, nicosulfuron, nipyraclofen, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pebulate, pendimethalin, penoxsulam, pentanochlor, pentoxazone, pethoxamid, phenmedipham, picloram, picolinafen, piperophos, pretilachlor, primisulfuron, prodiamine, profluazol, proglinazine, prometon, prometryne, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrazogyl (HSA-961), pyrazolynate, pyrazosulfuron, pyrazoxyfen, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac-methyl, pyrithiobacsodium, pyroxasulfone quinclorac, quinmerac, quizalofop, quizalofop-P, rimsulfuron, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA-sodium, tebutam, tebuthiuron, tepraloxydim, terbacil, terbumeton, terbuthyl-azine, terbutryn, thenylchlor, thiazafluron, thiazopyr, thidiazimin, thifensulfuron-methyl, thiobencarb, tiocarbazil, tioclorim, tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron, triclopyr, trietazine, trifloxysulfuron, trifluralin, triflusulfuron-methyl, tritosulfuron, UBI-C4874 (quizalofop-P), vernolate.
Esempi di fungicidi che possono essere aggiunti alle composizioni contenenti uno o più composti di formula generale (I) sono i seguenti:
acibenzolar, ametoctradin, amisulbrom, ampropylfos, anilazine, azaconazole, azoxystrobin, benalaxyl, benalaxyl-M, benomyl, benthiavalicarb, bitertanol, bixafen, blasticidin-S, boscalid, bromuconazole, bupirimate, buthiobate, captafol, captan, carbendazim, carboxin, carpropamid, chinomethionat, chloroneb, chlorothalonil, chlozolinate, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, debacarb, dichlofluanid, dichlone, diclobutrazol, diclomezine, dicloran, diclocymet, diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, dinocap, dipyrithione, ditalimfos, dithianon, dodemorph, dodine, edifenphos, epoxiconazole, etaconazole, ethaboxam, ethirimol, ethoxyquin, etridiazole, famoxadone, fenamidone, fenaminosulf, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fenpyrazamine, fentin, ferbam, ferimzone, fluazinam, fludioxonil, fluindapyr, flumetover, flumorph, fluopicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, furconazole, furconazole-cis, guazatine, hexaconazole, hymexazol, idrossichinolina solfato, imazalil, imibenconazole, iminoctadine, ipconazole, iprobenfos, iprodione, isoprothiolane, iprovalicarb, isopyrazam, isotianil, kasugamycin, kresoxim-methyl, mancopper, mancozeb, mandipropamid, maneb, mebenil, mepanipyrim, mepronil, meptyldinocap, metalaxyl, metalaxyl-M, metconazole, methfuroxam, metiram, metominostrobin, metrafenone, metsulfovax, myclobutanil, natamycin, nicobifen, nitrothal-isopropyl, nuarimol, ofurace, orysastrobin, oxadixyl, oxpoconazole, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorofenol e suoi sali, penthiopyrad, phthalide, picoxystrobin, piperalin, poltiglia bordolese, polyoxins, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, proquinazid, prothiocarb, prothioconazole, pyracarbolid, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyrifenox, pyrimethanil, pyriofenone, pyroquilon, pyroxyfur, quinacetol, quinazamid, quinconazole, quinoxyfen, quintozene, rabenzazole, rame idrossido, rame ossicloruro, rame (I) ossido, rame solfato, sedaxane, silthiofam, simeconazole, spiroxamine, streptomycin, tebuconazole, tebufloquin, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, thiophanate, thiophanate-methyl, thiram, tiadinil, tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triarimol, triazbutil, triazoxide, tricyclazole, tridemorf, trifloxystrobin, triflumizole, triforine, triticonazole, uniconazole, uniconazole-P, validamycin, valifenalate, vinclozolin, zineb, ziram, zolfo, zoxamide.
Esempi di battericidi che possono essere aggiunti alle composizioni contenenti uno o più composti di formula generale (I) sono i seguenti:
bronopol, dichlorophen, nitrapyrina, nickel dimetilditiocarbammato, kasugamycin, octhilinone, acido furancarbossilico, probenazole, streptomicina, tecloftalam, rame idrossido, rame ossicloruro, rame (I) ossido, rame solfato, rame salicilato.
Esempi di fertilizzanti e biostimolanti che possono essere aggiunti alle composizioni contenenti uno o più composti di formula generale (I) sono i seguenti:
miscele di amminoacidi e/o oligopeptidi di origine animale e/o vegetale, acido 4-tiazolidincarbossilico, acido 4- acetiltiazolidin-carbossilico, ectoina, fitosteroli.
Costituiscono pertanto un ulteriore oggetto della presente invenzione composizioni agronomiche comprendenti almeno un composto di Formula (I) e almeno un secondo principio attivo scelto tra insetticidi, acaricidi, nematocidi diversi da quelli di Formula (I), erbicidi, fungicidi, battericidi, fertilizzanti e biostimolanti.
Le composizioni oggetto della presente invenzione sono in grado di esplicare un’azione nematocida che può essere a carattere curativo e/o preventivo e, in generale, esibiscono una fitotossicità molto bassa o nulla sulle colture trattate. E’ quindi ulteriore oggetto della presente invenzione l’uso delle composizioni comprendenti almeno un composto di Formula (I) per il controllo dei nematodi. Nel caso in cui le composizioni comprendano un composto di Formula (I) e almeno un ulteriore principio attivo noto, i rapporti in peso nelle suddette composizioni, tra composto di Formula (I) e gli ulteriori principi attivi noti, variano a seconda dei composti prescelti e possono essere di norma compresi nell'intervallo da 1:100 a 100:1, preferibilmente da 1:10 a 10:1.
La concentrazione totale dei componenti attivi nelle suddette composizioni può variare entro un ampio intervallo; in generale, essa varia dall’1% al 99% in peso rispetto al peso totale della composizione, preferibilmente dal 5% al 90% in peso rispetto al peso totale della composizione.
I composti di Formula (I) o le composizioni che le contengono possono essere applicati alla coltura per via fogliare, oppure al suolo mediante fertirrigazione, oppure incorporazione al terreno, oppure tramite concia al seme.
Ulteriore oggetto della presente invenzione è quindi un metodo per il controllo dei nematodi in aree coltivate, che consiste nell’applicare dosi efficaci e non fitotossiche di composizioni comprendenti almeno un composto di Formula (I) e, opzionalmente, uno o più principi attivi noti con esso compatibili, su una parte qualsiasi della pianta da proteggere.
La quantità di composto da applicare per ottenere l’effetto desiderato può variare in funzione di diversi fattori quali, ad esempio, il composto utilizzato, la coltura da proteggere, il grado di infestazione, le condizioni climatiche, le caratteristiche del suolo, il metodo di applicazione, ecc.
Dosi di composto di Formula (I) che variano da 100g a 10000g per ettaro di coltura agricola o, nel caso di composizioni comprendenti altri principi attivi noti, dosi complessive di principi attivi che variano da 100g a 20000g per ettaro di coltura agricola forniscono, in genere, un sufficiente controllo.
Preferibilmente, si impiegano dosi di composto di Formula (I) che variano da 500g a 800g per ettaro di coltura agricola.
Allo scopo di meglio illustrare l’invenzione, vengono ora forniti i seguenti esempi che sono da ritenersi illustrativi e non limitativi della stessa.
ESEMPIO 1
Preparazione di 5-metil-1,3,4-tiadiazol-2-carbossilato di 3,4,4-trifluoro-3-butenile [Composto N°4]
a) Preparazione del sale di litio dell’acido 5-metil-1,3,4-tiadiazol-2-carbossilico di formula generale (II)]
A una soluzione di 0,340g (1,97 mmol) di 5-metil-1,3,4-tiadiazol-2-carbossilato di etile in 4 ml di tetraidrofurano sono stati aggiunti, sotto agitazione, 4 ml di una soluzione acquosa contenente 0,047 g (1,97 mmol) di idrossido di litio a 0°C. La miscela di reazione è stata poi portata a temperatura ambiente e lasciata in agitazione per una notte.
Il giorno seguente il solvente è stato evaporato e il sale di litio dell’acido 5-metil-1,3,4-tiadiazol-2-carbossilico è stato utilizzato tal quale per la reazione successiva.
b) Preparazione di 5-metil-1,3,4-tiadiazol-2-carbossilato di 3,4,4-trifluoro-3-butenile [Composto N°4].
A una soluzione di 0,28 g (1,94 mmol) di sale di litio dell’acido 5-metil-1,3,4-tiadiazol-2-carbossilico, ottenuto dalla reazione precedente, sciolti in 6 ml di N,N-dimetilformammide, sono stati aggiunti, 0.84 g (4,46 mmol) di 1-bromo-3,4,4-trifluoro-3-butene. La miscela è stata lasciata sotto agitazione magnetica a temperatura ambiente per tre ore.
Dopo controllo in LC-MS la miscela è stata diluita con acqua e sono state quindi separate le fasi; la fase acquosa è stata riestratta due volte con acetato di etile. Le fasi organiche riunite sono state abbondantemente lavate con una soluzione satura di cloruro di sodio e successivamente con acqua. Dopo anidrificazione su solfato di sodio, filtrazione ed evaporazione del solvente a pressione ridotta sono stati ottenuti 0,31g di olio arancione (1,3 mmol). Il grezzo così ottenuto è stato purificato per cromatografia su gel di silice eluendo con una miscela eptano:acetato di etile 3:2, ottenendo 0,29g (1,15 mmol) di prodotto desiderato. Resa 60%
LC-MS [M+H] = 253
ESEMPIO 2
Preparazione di 2-metil-4-difluorometil-tiazol-5-carbossilato di 3,4,4-trifluoro-3-butenile [Composto N°2]
In atmosfera di azoto, 1 g (5,17 mmol) di acido 2-metil-4-difluorometil-tiazol-5-carbossilico è stato sciolto in 20 ml di N,N-dimetilformammide. Poi, sotto agitazione e mantenendo la miscela di reazione a temperatura ambiente, sono stati addizionati 1,1 g (7,75 mmol) di carbonato di potassio e 2,25 g di 1-bromo-3,4,4-trifluoro-3-butene. Terminata l’aggiunta, la miscela è stata scaldata a 70°C per 3 ore e lasciata a temperatura ambiente per una notte.
Dopo controllo in LC-MS la miscela è stata diluita con acqua e quindi sono state
separate le fasi; la fase acquosa è stata riestratta due volte con acetato di etile. Le
fasi organiche riunite sono state lavate abbondantemente con una soluzione satura
di cloruro di sodio e successivamente con acqua. Dopo anidrificazione su solfato
di sodio, filtrazione ed evaporazione del solvente a pressione ridotta sono stati
ottenuti 1,42 g di olio giallo (4,7 mmol). Resa 92%
LC-MS [M+H] = 302.
Operando analogamente a quanto indicato negli Esempi 1 e 2, sono stati preparati
i Composti 1, 3, 12, 13, 14, 15, 16, 17, 118, riportati in Tabella 3.
Tabella 3
In Tabella 4 sono stati riportati i risultati delle analisi LC-MS condotte sui
Composti 1, 3, 12, 13, 14, 15, 16, 17, 118.
Tabella 4
Comp. N° LC-MS: M+
1 272
3 320
12 300
13 285
14 253
15 281
16 263
17 373
118 303
ESEMPIO 4
Determinazione dell’attività nematocida contro Meloidogyne sp.
I test volti a saggiare l’attività nematocida del prodotto in esame sono stati
effettuati utilizzando inoculi prelevati da un allevamento di Meloidogyne sp.
mantenuto su piante di pomodoro e cetriolo in vaso e allevati in serra.
Per effettuare le sperimentazioni, dai vasi infestati sono state prelevate porzioni di
radici che presentano un buon numero di galle, e terreno, nel quale sono presenti
larve a partire dal secondo stadio di età.
Nuovi vasi aventi diametro di 15 cm sono stati riempiti a metà con terra sterile. Su
di essa sono state posate le porzioni di radici infestate, preventivamente ripulite,
per poterne valutare correttamente il grado di infestazione e per assicurare che
ogni vaso contenga la stessa carica nematica. Sono stati quindi aggiunti 200-300 g
di terreno infestato, ricoperti poi con un sottile strato di terra sterile.
Il trattamento è stato condotto versando sulla superficie del terreno 100 ml di
soluzione in cui è stato disciolto il prodotto da testare.
Nei vasi così preparati, a distanza di uno o sette giorni dall’applicazione, sono
state trapiantate piantine di pomodoro o cetriolo allo stadio di due-tre foglie vere.
Sono state impiegate differenti cultivar di pomodoro o cetriolo, aventi differente
sensibilità al parassita e tempi diversi di accrescimento. In particolare, per la stima
della produzione finale, è stata impiegata una varietà di pomodoro ornamentale
(cv Microtom), le cui piantine sono di ridotte dimensioni e sono in grado di raggiungere in vaso ed in condizioni di serra la maturità dei frutti in circa due mesi.
Il prodotto è stato valutato considerando gli eventuali effetti fitotossici che possono compromettere lo sviluppo della pianta (in tal caso è stata impiegata una scala zero-dieci secondo la quale zero = nessun sintomo, 10 = pianta distrutta) e l’efficacia nei confronti del nematode.
La capacità di contenimento del parassita è stata rilevata, a distanza di 30 e 60 giorni dal trapianto, considerando lo sviluppo dell’apparato radicale (dove 100% è lo sviluppo raggiunto dalla radice sana di confronto) e la presenza di galle sulle radici. Questa è stata stimata impiegando la scala di infestazione proposta da Bridge-Page, secondo la quale al valore zero corrisponde lo 0% di radice colpita ed al valore 10 corrisponde il 100% di radice infestata.
In Tabella 5 sono riportati i risultati relativi alla fitotossicità su cetriolo, cv Lungo della Cina, trattando con i Composti N°2, 4, 12, 13, 17 compresi nella formula generale (I) e CR1, decritto in JP 2000038379.al posto del composto di formula generale (I).
Tabella 5
CR1= piridil-3-carbossilato di 3,4,4-trifluoro-3-butenile
In Tabella 6 sono stati riportati i risultati relativi alla efficacia dei Composti N°2, 4, 12, 13, 17 e del Composto CR1, su cetriolo, cv Lungo della Cina, alla dose di 4000 g/ettaro effettuando il rilievo a 30gg dal trapianto.
Tabella 6
CR1= piridil-3-carbossilato di 3,4,4-trifluoro-3-butenile
Claims (13)
- RIVENDICAZIONI 1. Esteri di composti eterociclici aventi formula generale (I):
- in cui: - Het rappresenta un eterociclo aromatico da 5 a 10 termini, eventualmente benzocondensato, o eterobiciclico contenente eteroatomi scelti tra azoto, zolfo ed ossigeno; detto eterociclo essendo opzionalmente sostituito da uno o più gruppi Y scelti tra alogeno, C1-C6-alchile, C1-C6-aloalchile, C3-C6-cicloalchile, C4-C7-cicloalchilalchile, C1-C6-alcossile, C1-C6-aloalcossile, C1-C6-tioalcossile, C1-C6-tioaloalcossili, C1-C6-alchilsulfinile, C1-C6-alchilsulfonile, C1-C6-alcossicarbonile, C3-C6-cicloalcossicarbonile, ammino, N-C1-C6-alchilammino, N,N-C2-C12-dialchilammino, N-C1-C6-alcossicarbonilammino, N-C3-C6-cicloalchilammino, N,N-C6-C12-dicicloalchilammino, N-C3-C6-cicloalcossicarbonilammino, C1-C6-alchilamminocarbonile, C3-C6-cicloalchilamminocarbonile, un gruppo NR1R2CONR1-formile, C1-C6-alchilcarbonile, carbossile, ciano, un arile opzionalmente sostituito, un benzile, un eterociclico aromatico opzionalmente sostituito, penta- oppure esa-atomico anche benzocondensato o eterobiciclico, contenente almeno un eteroatomo scelto tra ossigeno, zolfo, azoto, eventualmente ossidato a N-ossido; - n rappresenta un numero intero compreso tra 0 e 4; - m rappresenta un numero intero compreso tra 1 e 6; - X rappresenta un atomo di H o di fluoro; - R1, R2 uguali o diversi tra loro rappresentano un atomo di idrogeno, un gruppo C1-C4 alchilico oppure un gruppo C3-C6- cicloalchilico, con la condizione che: se n assume il valore 1, X rappresenta un atomo di F per qualsiasi significato di Het e di m; se Het rappresenta un gruppo tiofen-2-ile o un gruppo furan-2-ile o un gruppo pirazin-2-ile o un gruppo chinol-4-ile o pirrolil-2-ile sostituiti o non sostituiti da uno o più gruppi Y oppure Het rappresenta un gruppo pirazol-5-ile o un gruppo piridil-2-ile o piridil-3-ile o piridil-4-ile non sostituito o sostituito da uno o più gruppi Y scelti tra alogeno, C1-C6-alchile, C1-C6-alcossile, C1-C6-tioalcossile, C1-C6-tioaloalcossili, arile, oppure Het rappresenta un gruppo 1,2,3-tiadiazol-4-ile o un gruppo 1,2,3-tiadiazol-5-ile sostituiti o non sostituiti da uno o più gruppi Y, allora, contemporaneamente, n deve essere diverso da 0 e X diverso da H; se Het rappresenta un gruppo pirazol-4-ile sostituito o non sostituito da uno o più gruppi Y, allora contemporaneamente n deve essere diverso da 1, m diverso da 1 e X diverso da F. 2. Esteri secondo la rivendicazione 1, dove Het, n, m, e X nella formula (I) assumono i significati riportati nella seguente Tabella
- 3. Esteri secondo la rivendicazione 1 o 2, dove Het, n, m, e X nella formula (I) assumono i significati riportati nella seguente Tabella
- 4. Uso di esteri di composti eterociclici aventi formula generale (I) secondo una qualsiasi delle rivendicazioni da 1 a 3, per il controllo di nematodi.
- 5. Uso di esteri di composti eterociclici aventi formula generale (I) secondo la rivendicazione 4 per il controllo di Pratylenchus spp, Globodera spp, Heterodera spp, Meloidogyne spp, Aphelenchoides spp, Radopholus Similis, Ditylenchus Dipsaci, Tylenchulus Semipenetrans, Longidorus spp, Xiphinema spp, Trichodorus spp, Bursaphelenchus spp, Belonolaimus spp, a carattere curativo e/o preventivo.
- 6. Composizioni agronomiche comprendenti uno o più composti di Formula (I) secondo una o più delle rivendicazioni da 1 a 3, in combinazione con un solvente e/o diluente solido, liquido o liquefatto, eventualmente uno o più tensioattivi e altri coformulanti agronomicamente accettabili.
- 7. Composizioni agronomiche secondo la rivendicazione 6, dove la concentrazione di composto attivo di Formula (I) varia dallo 0,1 al 90% in peso rispetto al peso totale della composizione, preferibilmente dallo 0,5 al 90% in peso.
- 8. Composizioni agronomiche secondo una o più delle rivendicazioni da 6 a 7, comprendenti almeno un composto di Formula (I) e almeno un secondo principio attivo scelto tra insetticidi, acaricidi, nematocidi diversi da quelli di Formula (I), erbicidi, fungicidi, battericidi, fertilizzanti e biostimolanti.
- 9. Composizioni agronomiche secondo la rivendicazione 8, dove il rapporto in peso tra composto di Formula (I) e ulteriori principi attivi varia da 1:100 a 100:1, preferibilmente da 1:10 a 10:1.
- 10. Composizioni agronomiche secondo la rivendicazione 9, dove la concentrazione di principio attivo varia dallo 0,5 al 90% in peso rispetto al peso totale della composizione, preferibilmente dal 5 al 90% in peso.
- 11. Uso delle composizioni agronomiche secondo una o più delle rivendicazioni da 6 a 10, per il controllo dei nematodi.
- 12. Uso delle composizioni agronomiche secondo la rivendicazione 11, mediante applicazione della composizione alla coltura per via fogliare, o al suolo mediante fertirrigazione, o mediante incorporazione al terreno, o tramite concia del seme.
- 13. Metodo per il controllo dei nematodi in aree coltivate, che consiste nell’applicare su una parte qualsiasi della pianta da proteggere dosi efficaci e non fitotossiche di un composto avente formula generale (I) secondo una qualsiasi delle rivendicazioni da 1 a 3 o di composizioni agronomiche secondo una qualsiasi delle rivendicazioni da 6 a 10, comprendenti almeno un composto di Formula (I) e, opzionalmente, uno o più ulteriori principi attivi noti con esso compatibili.
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
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IT102018000004120A IT201800004120A1 (it) | 2018-03-30 | 2018-03-30 | Esteri di composti eterociclici ad attività nematocida, loro composizioni agronomiche e relativo uso |
ARP190100825A AR115313A1 (es) | 2018-03-30 | 2019-03-29 | Ésteres de compuestos heterocíclicos con actividad nematicida, sus composiciones agronómicas y su uso |
UY38167A UY38167A (es) | 2018-03-30 | 2019-03-29 | Ésteres de compuestos heterocíclicos con actividad nematicida, sus composiciones agronómicas y su uso |
PCT/IB2019/052617 WO2019186498A1 (en) | 2018-03-30 | 2019-03-29 | Esters of heterocyclic compounds having a nematocidal activity, their agronomic compositions and their use |
BR112020019619-3A BR112020019619A2 (pt) | 2018-03-30 | 2019-03-29 | Ésteres de compostos heterocíclicos, usos de ésteres dos compostos heterocíclicos e das composições agronômicas, composições agronômicas, e, método para o controle de nematódeos. |
US17/041,919 US20210127678A1 (en) | 2018-03-30 | 2019-03-29 | Esters of heterocyclic compounds having a nematocidal activity, their agronomic compositions and their use |
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IT102018000004120A IT201800004120A1 (it) | 2018-03-30 | 2018-03-30 | Esteri di composti eterociclici ad attività nematocida, loro composizioni agronomiche e relativo uso |
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AR (1) | AR115313A1 (it) |
BR (1) | BR112020019619A2 (it) |
IT (1) | IT201800004120A1 (it) |
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1986007590A1 (en) * | 1985-06-20 | 1986-12-31 | Fmc Corporation | Pesticidal polyhaloalkene derivatives |
WO1999052882A1 (fr) * | 1998-04-13 | 1999-10-21 | Nihon Nohyaku Co., Ltd. | Derive de 1,2,3-thiadiazole ou son sel et agent antiparasitaire, et procede d'utilisation |
JP2000038379A (ja) * | 1998-07-24 | 2000-02-08 | Ube Ind Ltd | ピリジンカルボン酸ハロアルケニルエステル誘導体、その製法及び農園芸用の有害生物防除剤 |
JP2000086636A (ja) * | 1998-09-09 | 2000-03-28 | Ube Ind Ltd | ピラゾールカルボン酸ハロアルケニルエステル誘導体、その製法及び農園芸用の有害生物防除剤 |
JP2000186073A (ja) * | 1998-12-22 | 2000-07-04 | Ube Ind Ltd | ヘテロ環カルボン酸ハロアルケニルエステル誘導体、その製法及び農園芸用の有害生物防除剤 |
WO2003042153A1 (fr) * | 2001-11-15 | 2003-05-22 | Kumiai Chemical Industry Co., Ltd. | Derive de difluoroalcene, et pesticide renfermant ce derive |
-
2018
- 2018-03-30 IT IT102018000004120A patent/IT201800004120A1/it unknown
-
2019
- 2019-03-29 AR ARP190100825A patent/AR115313A1/es unknown
- 2019-03-29 UY UY38167A patent/UY38167A/es not_active Application Discontinuation
- 2019-03-29 US US17/041,919 patent/US20210127678A1/en not_active Abandoned
- 2019-03-29 WO PCT/IB2019/052617 patent/WO2019186498A1/en active Application Filing
- 2019-03-29 BR BR112020019619-3A patent/BR112020019619A2/pt active Search and Examination
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1986007590A1 (en) * | 1985-06-20 | 1986-12-31 | Fmc Corporation | Pesticidal polyhaloalkene derivatives |
WO1999052882A1 (fr) * | 1998-04-13 | 1999-10-21 | Nihon Nohyaku Co., Ltd. | Derive de 1,2,3-thiadiazole ou son sel et agent antiparasitaire, et procede d'utilisation |
JP2000038379A (ja) * | 1998-07-24 | 2000-02-08 | Ube Ind Ltd | ピリジンカルボン酸ハロアルケニルエステル誘導体、その製法及び農園芸用の有害生物防除剤 |
JP2000086636A (ja) * | 1998-09-09 | 2000-03-28 | Ube Ind Ltd | ピラゾールカルボン酸ハロアルケニルエステル誘導体、その製法及び農園芸用の有害生物防除剤 |
JP2000186073A (ja) * | 1998-12-22 | 2000-07-04 | Ube Ind Ltd | ヘテロ環カルボン酸ハロアルケニルエステル誘導体、その製法及び農園芸用の有害生物防除剤 |
WO2003042153A1 (fr) * | 2001-11-15 | 2003-05-22 | Kumiai Chemical Industry Co., Ltd. | Derive de difluoroalcene, et pesticide renfermant ce derive |
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WO2019186498A1 (en) | 2019-10-03 |
BR112020019619A2 (pt) | 2021-01-05 |
AR115313A1 (es) | 2020-12-23 |
US20210127678A1 (en) | 2021-05-06 |
UY38167A (es) | 2019-10-31 |
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