ITMI20101564A1 - Fenilammidine ad elevata attivita' fungicida e relativo uso - Google Patents
Fenilammidine ad elevata attivita' fungicida e relativo uso Download PDFInfo
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- ITMI20101564A1 ITMI20101564A1 IT001564A ITMI20101564A ITMI20101564A1 IT MI20101564 A1 ITMI20101564 A1 IT MI20101564A1 IT 001564 A IT001564 A IT 001564A IT MI20101564 A ITMI20101564 A IT MI20101564A IT MI20101564 A1 ITMI20101564 A1 IT MI20101564A1
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- 230000000855 fungicidal effect Effects 0.000 title claims description 21
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 title 1
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- 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
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- 125000004429 atom Chemical group 0.000 claims description 5
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- 238000000034 method Methods 0.000 claims description 5
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
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- 238000006243 chemical reaction Methods 0.000 description 15
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- 231100000674 Phytotoxicity Toxicity 0.000 description 4
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- 229960003811 pyrithione disulfide Drugs 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
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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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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
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- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-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
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
- C07C323/41—Y being a hydrogen or an acyclic carbon atom
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- 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
- A01N37/52—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 groups, e.g. carboxylic acid amidines
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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
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A—HUMAN NECESSITIES
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- 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
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- 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
- A01N43/84—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
- C07D237/18—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
- C07D241/18—Oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Description
"Fenilammidine ad elevata attività fungicida e relativo
US O rr
La presente invenzione riguarda fenilammidine ad elevata attività fungicida e il relativo uso, in particolare fenilammidine sostituite dotate di elevata attività fungicida ed il loro uso per il controllo di funghi fitopatogeni di importanti colture agricole.
Fenilammidine ad attività fungicida sono descritte nelle domande di brevetto internazionale WO 2000/46184, WO 2003/093224, WO 2007/031508, WO 2007/031512, WO 2007/031513, WO 2007/031523, WO 2007/031524, WO 2008/110279.
Fenilammidine ad attività erbicida sono descritte in WO 2008/110278.
I prodotti descritti in questi documenti risultano però spesso insoddisfacenti sia sotto il profilo del livello di attività nei confronti dei funghi fitopatogeni sia, o in alternativa, sotto il profilo della fitotossicità nei confronti di importanti colture agricole.
In particolar modo, ad esempio, i composti N-etil-N-metil-N'- [4-(3-trifluorometilfenossi)-2,5-xilil]-formammidina e N,N-dimetil-N '-[4-(3-trifluorometilfenossi)-2,5-xilil]formammidina, descritti nella domanda internazionale WO 00/46184, alle dosi che permettono di ottenere una buona attività fungicida, manifestano una spiccata necrosi fogliare su cereali, cetriolo, pomodoro ed altre importanti colture: tale effetto ne rende in pratica non proponibile l'utilizzo come fungicidi. D'altra parte, il composto N,N-dimetil-N'-[4-(3-trifluorometilfenil-tio )2,5-xilil] formammidina, anch'esso descritto nella domanda internazionale WO 00/46184, risulta insufficiente sotto il profilo dell'attività fungicida, che si esplica in maniera soddisfacente a dosi eccessivamente elevate.
La Richiedente ha ora sorprendentemente trovato che nuove fenilammidine caratterizzate da un gruppo tioetereo in posizione 4 del fenile e da particolari combinazioni di sostituenti sull'atomo di azoto, oltre ad esibire un'eccellente attività fungicida a basse dosi, risultano molto ben tollerate da molte specie vegetali, consentendo quindi l'utilizzo pratico di questi composti per il controllo di microorganismi fitopatogeni di importanti colture agricole.
Costituiscono pertanto oggetto della presente invenzione nuove fenilammidine di formula generale (I):
m cui :
- R rappresenta un gruppo fenile, piridile, pirimidile, pirazile o piridazile, tutti gruppi opzionalmente sostituiti da uno a tre sostituenti, uguali o diversi tra loro, scelti tra: un atomo di alogeno, un alchile Ci-C6, un aloalchile Ci-C6, un alcossile Ci-C6, un aloalcossile Ci-C6, un cicloalchile C3-C6, un alocicloalchile C3-C6, un cicloalcossile C3-C6, un alocicloalcossile C3-C6;
- Ri rappresenta un alchile C2-C6;
- R2rappresenta un alchile 0ι-06;
oppure Ri ed R2, congiuntamente all'atomo di N cui sono legati, formano un anello eterociclico contenente da 4 a 7 atomi, eventualmente sostituito da atomi di alogeno ;
- R3ed R4, uguali o diversi tra loro, rappresentano un atomo di idrogeno, un atomo di alogeno, un alchile Ci-Ce, un alcossile Ci-C6, un aloalcossile Ci-C6, un gruppo CF3, un gruppo CF2H, un gruppo CFH2, un gruppo ciano.
Esempi di alogeno sono fluoro, cloro, bromo, iodio .
Esempi di alchile C1-C6sono metile, etile, npropile, isopropile, n-butile, isobutile, sec-butile, tert-butile, n-pentile, 3-metilbutile, n-esile, 3,3-dimet ilbutile .
Esempi di aloalchile C1-C6sono fluorometile, difluorometile, trif luorometile, clorometile, diclorometile, 2,2,2-trif luoroetile, 1, 1,2,2-tetraf luoroetile, pentaf luoroetile, eptafluoropropile, 4 ,4,4-triclorobutile, 4,4-dif luoropentile, 5,5-dif luoroesile .
Esempi di alcossile C1-C6sono metossi, etossi, npropossi, isopropossi, n-butossi, isobutossi, secbutossi, tert-butossi , n-pentossi, 3-met ilbutossi , esilossi, 3,3-dimet ilbutossi .
Esempi di aloalcossile Ci-C6sono fluorometossi , difluorometossi, trifluorometossi, clorometossi , diclorometossi , 2,2,2-trif luoroetossi, 1,1,2,2-tetrafluoroetossi, 1,1,2,3, 3,3-esaf luoropropossi, 4,4,4-triclorobutossi , 4,4-difluoropentossi, 5,5-difluoroesilossi.
Esempi di cicloalchile C3-C6 sono ciclopropile, ciclobutile, ciclopentile, cicloesile.
Esempi di alocicloalchile C3-C6 sono 2,2-diclorociclopropile, 2,2-difluorociclopropile, 2,2,3,3-tetrafluorociclobutile, 3,3-difluorociclopentile, 2-fluorocicloesile.
Esempi di cicloalcossile C3-C6 sono ciclopropossi, ciclobutossi, ciclopentossi, cicloesilossi.
Esempi di alocicloalcossile C3-C6 sono 2,2-dicloro-ciclopropossi, 2,2-difluorociclopropossi, 2.2.3.3-tetrafluorociclobutossi, 3,3-difluorociclopentossi, 2-fluorocicloesilossi.
Esempi di anelli eterociclici da 4 a 7 atomi eventualmente alogenati sono: aziridina, azetidina, 3.3-difluoroazetidina, pirrolidina, piperidina, 4-fluoropiperidina.
Esempi di composti di formula generale (I) preferiti sono i composti in cui R, Ri, R2, R3 e R4assumono i significati riportati in tabella 1.
Tabella 1
Particolarmente preferiti sono i composti in cui R, Ri, R2, R3e R3⁄4assumono i significati riportati in Tabella 2:
Tabella 2
I composti di formula generale (I) vengono preparati dalla corrispondente anilina di formula (II), secondo lo schema di reazione 1.
Schema 1
Sono noti dalla letteratura vari metodi per effettuare questa trasformazione; i più utilizzati sono i seguenti:
a) trattamento dell'anilina di formula (II) con un acefale di formula RIR2NC(OR5), dove R5 rappresenta un alchile, secondo quanto descritto in "Synthetic Communications", 24 (1994), pagg.1617-1624;
b) trattamento dell'anilina di formula (II) con un'ammide di formula HCONR1R2 in presenza di POCI3 o SOCI2,secondo quanto descritto in "Tetrahedron", 46 (1990), pagg.6058-6112;
c) trattamento dell'anilina di formula (II) con un ortoestere di formula HC(OR5), dove R5rappresenta un alchile, per formare il corrispondente imminoetere seguito dal riscaldamento dello stesso in presenza di un'ammina di formula HNRIR2,secondo quanto descritto in US4209319;
d) trattamento dell'anilina di formula (II) con fosgene per formare 1'isocianato corrispondente seguito dalla reazione con un'ammide di formula HCONR1R2, secondo quanto descritto in WO 00/46184;
e) trattamento dell'anilina di formula (II) con C2H5OCH=NCN per formare una N-cianoammidina seguita da reazione con un'ammina di formula HNR1R2,secondo quanto descritto in WO 00/46184;
f) trattamento dell'anilina di formula (II) con N,N-dimetilformammide in presenza di un solfonilcloruro, quale ad esempio 2-piridilsolfonilcloruro o fenilsolfonilcloruro, per formare la corrispondente dimetilammidina (Ri=R2=Me) seguita da reazione con un'ammina di formula HNR1R2,secondo quanto descritto in "Tetrahedron", 56 (2000), pagg.8253-8262 ed in "Journal Combinatorial Chemistry" 11 (2009), pagg.126-130.
Il composto di formula (II) può essere preparato per riduzione del corrispondente nitroderivato di formula (III), come riportato nello schema di reazione 2, secondo metodi ben noti in chimica organica, come descritto ad esempio in "Advanced Organic Chemistry", Jerry March, 4<a>Edizione, 1992, John Wiley & Sons Pub., pagg. 1216-1217 e referenze ivi citate.
Schema 2
Le condizioni di reazione preferite per questi substrati prevedono l'utilizzo dello stagno cloruro in acido cloridrico concentrato, secondo quanto descritto in dettaglio nella domanda internazionale WO 00/46184.
Il composto di formula (III) può essere preparato per reazione del composto di formula (IV) con un composto di formula RX, dove X è un gruppo uscente quale, ad esempio, un atomo di alogeno, in presenza di una base, preferibilmente carbonato di potassio o sodio idruro, secondo lo schema di reazione 3.
Schema 3
Alternativamente il composto di formula (III) può essere anche ottenuto per reazione del composto di formula (V), dove Y rappresenta un atomo di bromo o cloro, con un composto di formula RSH, in presenza di una base, preferibilmente carbonato di potassio o sodio idruro, secondo lo schema di reazione 4.
Schema 4
I composti di formula (IV) vengono preparati facendo reagire, in presenza di un catalizzatore di palladio, un composto di formula (V) con tioacetato di potassio e successivamente saponificando il tioestere così ottenuto, secondo quanto descritto in "Tetrahedron Letters", 48 (2007), pagg.3033-303 7.
Come detto, i composti di formula generale (I) sono dotati di un'attività fungicida molto elevata che si esplica nei confronti di numerosi funghi fitopatogeni che attaccano importanti colture agricole.
Esempi di funghi fitopatogeni che possono essere efficacemente trattati e combattuti con i composti di formula generale (I) sono quelli appartenenti alle classi dei Basidiomiceti, Ascomiceti, Deuteromiceti o funghi imperfetti, Oomiceti: Puccinia spp., Ustilago spp., Tilletia spp., Uromyces spp., Phakopsora spp., Rhizoctonia spp., Erysiphe spp., Sphaerotheca spp., Podosphaera spp., Uncinula spp., Helminthosporium spp., Rhynchosporium spp., Pyrenophora spp., Monilinia spp., Sclerotinia spp., Septoria spp. (Mycosphaerella spp.), Venturia spp., Botrytis spp., Aiternaria spp., Fusarium spp., Cercospora spp., Cercosporella herpotrichoides, Colletotrichum spp., Pyricularia oryzae, Sclerotium spp., Phytophtora spp., Pythium spp., Plasmopara viticola, Peronospora spp., Pseudoperonospora cubensis, Bremia lactucae.
Le principali colture che possono essere protette con i composti secondo la presente invenzione comprendono cereali (grano, orzo, segale, avena, riso, mais, sorgo, ecc.), fruttiferi (melo, pero, susino, pesco, mandorlo, ciliegio, banano, vite, fragola, lampone, mora, ecc.), agrumi (arancio, limone, mandarino, pompeimo, ecc.), leguminose (fagiolo, pisello, lenticchia, soia, ecc.), orticole (spinacio, lattuga, asparago, cavolo, carota, cipolla, pomodoro, patata, melanzana, peperone, ecc.), cucurbitacee (zucca, zucchina, cetriolo, melone, anguria, ecc.), piante oleoginose (girasole, colza, arachide, ricino, cocco, ecc.), tabacco, caffè, tè, cacao, barbabietola da zucchero, canna da zucchero, cotone.
In particolare, i composti di formula (I) si sono dimostrati notevolmente efficaci nel controllo di Plasmopara viticola su vite, Phytophtora infestans e Botrytis Cinerea su pomodoro, Puccinia recondita, Erisiphae graminis, Helminthosporium teres, Septoria nodorum e Fusarium spp. su cereali, nel controllo di Phakopsora pachyrhizi su soia, nel controllo di Uromyces Appendiculatus su fagiolo, nel controllo di Venturia inaequalis su melo, nel controllo di Sphaerotheca fuliginea su cetriolo.
Inoltre, i composti di formula generale (I) sono efficaci anche nel controllo di batteri e virus fitopatogeni, quali ad esempio Xanthomonas spp., Pseudomonas spp., Erwinia amylovora, il virus del mosaico del tabacco.
I composti di formula (I) sono in grado di esplicare un'azione fungicida a carattere sia curativo sia preventivo ed esibiscono una fitotossicità molto bassa o nulla sulle colture trattate.
E' quindi ulteriore oggetto della presente invenzione l'uso dei composti di formula (I) per il controllo di funghi fitopatogeni di colture agricole.
Per gli impieghi pratici in agricoltura è spesso preferibile utilizzare composizioni fungicide contenenti i composti secondo la presente invenzione opportunamente formulati.
Sono un ulteriore oggetto della presente invenzione composizioni fungicide comprendenti uno o più composti di formula (I), un solvente e/o diluente solido o liquido, eventualmente un tensioattivo.
Le suddette composizioni fungicide possono presentarsi sotto forma di polveri secche, polveri bagnabili, concentrati emulsionabili, emulsioni, microemulsioni, paste, granuli, granuli disperdibili in acqua, soluzioni, sospensioni, ecc.: la scelta del tipo di composizione dipenderà dall'impiego specifico.
Le composizioni fungicide vengono preparate in maniera nota, per esempio diluendo o sciogliendo la sostanza attiva con un mezzo solvente e/o un diluente solido o liquido, eventualmente in presenza di tensioattivi.
Come diluenti solidi, o supporti, possono essere ad esempio utilizzati: silice, caolino, bentonite, talco, farina fossile, dolomite, carbonato di calcio, magnesia, gesso, argille, silicati sintetici, attapulgite, seppiolite.
Come solventi o diluenti liquidi possono essere ad esempio utilizzati, oltre all'acqua, solventi organici aromatici (xiloli o miscele di alchilbenzoli, clorobenzene, ecc.), paraffine (frazioni di petrolio), alcooli (metanolo, propanolo, butanolo, ottanolo, glicerina, ecc.), esteri (acetato di etile, di isobutile, alchil carbonati, esteri alchilici dell'acido adipico, esteri alchilici dell'acido glutarico, esteri alchilici dell'acido succinico, esteri alchilici dell'acido lattico, ecc.), olii vegetali (olio di colza, olio di girasole, olio di soia, olio di ricino, olio di mais, olio di arachidi, e loro esteri alchilici), chetoni (cicloesanone, acetone, acetofenone, isoforone, etilamilchetone, ecc.), ammidi (N,N-dimetilformammide, N-metilpirrolidone, ecc.), solfossidi e solfoni (dimetilsolfossido, dimetilsolfone, ecc.), e loro miscele.
Come tensioattivi possono essere utilizzati sali di sodio, di calcio, di potassio, di trietilammina o trietanolammina di alchilnaf talensolfonati, polinaftalensolfonati, alchilsolfonati, arilsolfonati, alchilarilsolfonati, policarbossilati, solfosuccinati, alchilsolfosuccinati, lignin solfonati, alchilsolfati; ed ancora possono essere utilizzati alcoli grassi polietossilati, alchilfenoli polietossilati, esteri del sorbitolo polietossilati, polipropossi polietossilati (block polymers).
Le composizioni fungicide possono anche contenere additivi speciali per particolari scopi, ad esempio anticongelanti quali glicole propilenico, oppure agenti adesivanti quali gomma arabica, alcool polivinilico, polivinilpirrolidone, ecc..
Qualora lo si desideri, è possibile aggiungere alle composizioni fungicide contenenti i composti di formula generale (I), altri principi attivi con essi compatibili, quali ad esempio fungicidi diversi da quelli di formula generale (I), fitoregolatori, antibiotici, erbicidi, insetticidi, fertilizzanti e/o loro miscele.
Esempi di fungicidi diversi da quelli di formula generale (I) che possono essere inclusi nelle composizioni fungicide oggetto della presente invenzione sono: 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, dimethir imol, 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, 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.
La concentrazione dei composti fenilammidinici di formula generale (I) nelle suddette composizioni può variare entro un ampio intervallo; in generale essa è compresa tra 1% e 90% in peso rispetto al peso totale della composizione, preferibilmente tra 5 e 50% in peso rispetto al peso totale della composizione.
L'applicazione di queste composizioni può avvenire su ogni parte della pianta, per esempio su foglie, steli, rami e radici, oppure sui semi stessi prima della semina, oppure sul terreno in cui cresce la pianta.
Ulteriore oggetto della presente invenzione è quindi un metodo per il controllo di funghi fitopatogeni in colture agricole, che consiste nell'applicazione di dosi efficaci dei composti di formula (I), utilizzati come tali o formulati in composizioni fungicide come sopra descritte.
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 preservare, il tipo di patogeno, il grado di infezione, le condizioni climatiche, il metodo di applicazione, la formulazione adottata.
Dosi di composto comprese tra 10 g e 5 kg per ettaro di coltura agricola forniscono, in genere, un controllo sufficiente.
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 2-nitro-5-(3-trifluorometilfeniltio)—p— xilene [nitroderivato di formula generale (III)]
2,5 g di sodio idruro sono stati sospesi in 24 mi di N,N-dimetilformammide, portando poi la temperatura a 0°C mediante bagno di ghiaccio. 9,13 g di 3-(trifluorometil)tiofenolo sciolti in 24 mi di N,N-dimetilformammide sono stati quindi aggiunti per gocciolamento. Una volta terminato lo sviluppo di gas, 9,5 g di 5-cloro-2-nitro-p-xilene disciolti in 24 mi di N,N-dimetilformammide sono stati aggiunti alla miscela di reazione mediante gocciolamento, mantenendo la temperatura a 0 °C.
Terminata l'aggiunta, la temperatura di reazione è stata lasciata salire spontaneamente sino a temperatura ambiente e mantenuta a tali valori per 4h.
La reazione è stata controllata in TLC (eluente esano:acetato di etile 7:3), poi il solvente è stato evaporato e il residuo estratto con acetato di etile. La fase organica è stata anidrificata su solfato di sodio, quindi filtrata ed evaporata.
Il prodotto così ottenuto è stato purificato su gel di silice eluendo con esano: acetato di etile 9:1.
Sono stati ottenuti 18,4 g di prodotto desiderato (GC-MS: 327 (M<+>).
ESEMPIO 2
Preparazione di 4- (3-trifluorometilfeniltio)-2,5— xilidina [anilina di formula generale (II)]
18,4 g di 2-nitro-5-(3-trifluorometilfeniltio)-pxilene e 38,09 g di stagno cloruro sono stati diluiti con 80 mi di metanolo. La miscela è stata raffreddata a 0°C con un bagno di ghiaccio e a questa temperatura sono stati aggiunti, gocciolandoli, 76 mi di HC1 al 37%.
Una volta terminato il gocciolamento, la temperatura è stata portata a 70°C per 1,5 h, la reazione è stata controllata in TLC (eluente esano:acetato di etile 7:3), poi la soluzione è stata basificata con carbonato di potassio fino a pH 9, quindi estratta con acetato di etile.
La fase organica è stata anidrificata su solfato di sodio, poi filtrata ed evaporata.
II prodotto cosi ottenuto, è stato lasciato in agitazione, a temperatura ambiente, con 30 mi di etere etilico fino alla precipitazione di un solido bianco che è stato filtrato.
Sono stati ottenuti 15,5 g di prodotto desiderato (GC-MS: 297 (M<+>).
ESEMPIO 3
Preparazione di N-etil-N-metil-N'-[4-(3-trifluorometilfeniltio) -2,5-xilil] formammidina [Composto N°l] e dei composti N° 2-83 di formula (I).
4,62 g di 4-(3-trifluorometilf eniltio)-2 ,5-xilidina, 25,84 mi di trietilortoformiato e 0,5 g di acido p-toluensolf onico sono stati scaldati a 130°C per 3 ore.
Dopo controllo della reazione in TLC (eluente esano: acetato di etile 7:3), la miscela è stata evaporata, diluita con 35 mi di cloruro di metilene, quindi addizionata con 1,8 g di N-etil-N-met ilammina .
La temperatura è stata portata a 40°C per 1,5 h e la reazione controllata in TLC (eluente esano:etile acetato 7:3), poi il solvente è stato evaporato.
Il prodotto così ottenuto è stato purificato su allumina neutra eluendo con esano:acetato di etile 9:1.
Sono stati ottenuti 3,5 g di prodotto desiderato.
<1>H-NMR (δ-ppm, CDC13) = 1.2 (t, 3H); 2.2 (s, 3H); 2.3 (s,3H); 3.0 (s, 3H); 3.4 (br, 2H); 6.7 (s, IH); 7.1 (m, IH); 7.20-7.40 (m, 4H); 7.5 (s, IH).
Operando analogamente a quanto sopra riportato, a partire dalle corrispondenti aniline e dialchilammine, sono stati ottenuti i composti di formula (I) riportati in Tabella 1.
Tabella 1
ESEMPIO 4
Determinazione dell' attività fungicida in applicazione preventiva (5 giorni) contro Erysiphe gramini s su grano.
Foglie di piante di grano di varietà Salgemma, allevate in vaso in ambiente condizionato a 20° C e al 70% di U.R. (Umidità Relativa), sono state trattate per irrorazione di ambedue le pagine con il composto sotto esame (vedi la seguente tabella 3), disperso in soluzione idroacetonica al 20% in volume di acetone.
Dopo 5 giorni di permanenza in ambiente condizionato, le piante sono state infettate a secco scuotendovi sopra, per spargere l'inoculo, delle piante precedentemente infettate da Erysiphe graminis.
Le piante sono state poi mantenute nella stessa cella, in ambiente saturo di umidità e temperatura compresa tra i 18 e 24°C per 12 giorni.
Trascorso questo periodo di tempo, sono comparsi i sintomi esteriori del patogeno ed è stato quindi possibile procedere alla valutazione dell'intensità dell'infezione, sia sulle parti trattate direttamente con i prodotti (T), sia sulle parti sviluppatesi durante l'esecuzione del test (NT), mediante scala di valutazione visiva della percentuale di area fogliare colpita; la scala prevede come estremi il valore 100 (pianta sana) ed il valore 0 (pianta completamente infetta).
Nel contempo si è proceduto alla valutazione della fitotossicità (percentuale di necrosi fogliare) indotta sulle piantine di grano dall'applicazione dei prodotti: in questo caso la scala di valutazione varia da 0 (pianta completamente sana) a 100 (pianta completamente necrotizzata).
In Tabella 3 sono riportati i risultati ottenuti effettuando il test descritto sul composto N°1 dell'esempio 3, in confronto con la N,N-dimetil-N'-[4-(3-trifluorometilfenossi)-2,5-xilil]formammidina (CR-1: composto N. 1, Tabella 1 di WO 00/46184), con la N,N-dimetil-N'-[4-(3-trifluorometilfeniltio)-2,5-xilil]-formammidina (CR-2: composto N. 4, Tabella 1 di WO 00/46184) e con la N-etil-N-metil-N'-[4-(3-trifluorometilfenossi)-2,5-xilil]formammidina (CR-3: composto N.
45, Tabella 1 di WO 00/46184).
Tabella 3
Il composto N. 1 è risultato meno fitotossico e/o più attivo rispetto ai prodotti di riferimento.
ESEMPIO 5
Determinazione dell' attività fungicida preventiva (5 giorni) contro Puccinia recondita su grano.
Foglie di piante di grano di varietà Salgemma, allevate in vaso in ambiente condizionato a 20° C e al 70% di U.R. (Umidità Relativa), sono state trattate per irrorazione di ambedue le pagine con il composto sotto esame (vedi la seguente tabella 4), disperso in soluzione idroacetonica al 20% in volume di acetone.
Dopo 5 giorni di permanenza in ambiente condizionato, le piante sono state irrorate su entrambe le pagine fogliari con una sospensione acquosa di conidi di Puccinia recondita (2 mg di inoculo per 1 mi di soluzione per infezione).
Dopo l'irrorazione, le piante sono state mantenute in ambiente saturo di umidità e temperatura compresa tra i 18 e 24°C per il periodo di incubazione del fungo (1 giorno).
Al termine di detto periodo, le piante sono state poste in serra con U.R. 70% e temperatura di 18-24 °C per 14 giorni.
Trascorso questo periodo di tempo, sono comparsi i sintomi esteriori del patogeno ed è stato quindi possibile procedere alla valutazione dell'intensità dell'infezione, sia sulle parti trattate direttamente con i prodotti (T), sia sulle parti sviluppatesi durante l'esecuzione del test (NT), mediante scala di valutazione visiva della percentuale di area fogliare colpita; la scala prevede come estremi il valore 100 (pianta sana) e il valore 0 (pianta completamente infetta) .
Nel contempo si è proceduto alla valutazione della fitotossicità (percentuale di necrosi fogliare) indotta sulle piantine di grano dall'applicazione dei prodotti: in questo caso la scala di valutazione varia da 0 (pianta completamente sana) a 100 (pianta completamente necrotizzata) .
In Tabella 4 sono riportati i risultati ottenuti effettuando il test descritto sul composto N°1 dell'esempio 3, in confronto con la N,N-dimetil-N '- [4-(3-trif luorometilf enossi )-2,5-xilil] formammidina (CR-1 : composto N. 1, Tabella 1 del WO 00/46184), con la N,N-dimet il-N '- [4-(3-trifluorometilfenilt io)-2,5-xilil] -formammidina (CR-2: composto N. 4, Tabella 1 del WO 00/46184) e con la N-etil-N-met il-N '-[4-(3-trifluorometilf enossi)-2 ,5-xilil ]formammidina (CR-3: composto N.
45, Tabella 1 del WO 00/46184).
Tabella 4
Il composto N. 1 è risultato meno fitotossico e/o più attivo rispetto ai prodotti di riferimento.
Claims (14)
- RIVENDICAZIONI 1) Fenilammidine di formula generale (I):
- in cui: - R rappresenta un gruppo fenile, piridile, pirimidile, pirazile o piridazile, tutti gruppi opzionalmente sostituiti da uno a tre sostituenti, uguali o diversi tra loro, scelti tra: un atomo di alogeno, un alchile Ci<—>C6, un aloalchile Ci-Cg, un alcossile Ci-Cg, un aloalcossile Ci-Cg, un cicloalchile C3-C6, un alocicloalchile C3-C6, un cicloalcossile C3-C6, un alocicloalcossile C3-C6,· - Ri rappresenta un alchile C2-Cg; - R2rappresenta un alchile Ci-Cg; oppure Ri ed R2, congiuntamente all'atomo di N cui sono legati, formano un anello eterociclico contenente da 4 a 7 atomi, eventualmente sostituito da atomi di alogeno ; - R3ed R4, uguali o diversi tra loro, rappresentano un atomo di idrogeno, un atomo di alogeno, un alchile Ci-Cg, un alcossile Ci-Cg, un aloalcossile Ci-Cg, un gruppo CF3, un gruppo CF2H, un gruppo CFH2, un gruppo ciano. 2) Fenilammidine secondo la rivendicazione 1 scelte tra i composti di formula generale (I), in cui R, Ri, R2, R3e R3⁄4assumono i seguenti significati:
- 3) Fenilammidine secondo la rivendicazione 1 scelte tra i composti di formula generale (I) in cui R, Ri, R2, R3e R3⁄4assumono i seguenti significati :
- 4) Composizioni fungicide comprendenti uno o più composti di formula (I) secondo una qualsiasi delle rivendicazioni da 1 a 3, un solvente e/o diluente solido o liquido, eventualmente un tensioattivo.
- 5) Composizioni secondo la rivendicazione 4, comprendenti, inoltre, principi attivi compatibili con i composti di formula generale (I), scelti tra fungicidi diversi dai composti di formula generale (I), fitoregolat or i, antibiotici, erbicidi, insetticidi, fertilizzanti e/o loro miscele, anticongelanti, agenti adesivanti.
- 6) Composizioni secondo la rivendicazione 4 o 5 in cui la concentrazione di composti di formula generale (I) è compresa tra 1 e 90% in peso rispetto al peso totale della composizione, preferibilmente tra 5 e 50% in peso rispetto al peso totale della composizione.
- 7) Uso di fenilammidine di formula generale (I):m cui : - R rappresenta un gruppo fenile, piridile, pirimidile, pirazile o piridazile, tutti gruppi opzionalmente sostituiti da uno a tre sostituenti, uguali o diversi tra loro, scelti tra: un atomo di alogeno, un alchile Ci<—>C6, un aloalchile C1-C6, un alcossile C1-C6, un aloalcossile C1-C6, un cicloalchile C3-C6, un alocicloalchile C3-C6, un cicloalcossile C3-C6, un alocicloalcossile C3-C6; - Ri rappresenta un alchile C2-C6; - R2rappresenta un alchile C1-C6; oppure Ri ed R2, congiuntamente all'atomo di N cui sono legati, formano un anello eterociclico contenente da 4 a 7 atomi, eventualmente sostituito da atomi di alogeno; - R3ed R4, uguali o diversi tra loro, rappresentano un atomo di idrogeno, un atomo di alogeno, un alchile Ci-C6, un alcossile Ci-C6, un aloalcossile Ci-C6, un gruppo CF3, un gruppo CF2H, un gruppo CFH2, un gruppo ciano per il controllo di funghi fitopatogeni di colture agricole.
- 8) Uso dei composti secondo una qualsiasi delle rivendicazioni 2-3 per il controllo di funghi fitopatogeni di colture agricole.
- 9) Uso di composizioni secondo una qualsiasi delle rivendicazioni 4-6 per il controllo di funghi fitopatogeni di colture agricole.
- 10) Uso secondo una qualsiasi delle rivendicazioni da 7 a 9 per il controllo di funghi fitopatogeni che appartengono alle classi dei Basidiomiceti, Ascomiceti, Deuteromiceti o funghi imperfetti, Oomiceti: Puccinia spp., Ustilago spp., Tilletia spp., Uromyces spp., Phakopsora spp., Rhizoctonia spp., Erysiphe spp., Sphaerotheca spp., Podosphaera spp., Uncinula spp., Helminthosporium spp., Rhynchosporium spp., Pyrenophora spp., Monilinia spp., Sclerotinia spp., Septoria spp. (Mycosphaerella spp.), Venturia spp., Botrytis spp., Aiternaria spp., Fusarium spp., Cercospora spp., Cercosporella herpotrichoides, Colletotrichum spp., Pyricularia oryzae, Sclerotium spp., Phytophtora spp., Pythium spp., Plasmopara viticola, Peronospora spp., Pseudoperonospora cubensis, Bremia lactucae.
- 11) Uso secondo una qualsiasi delle rivendicazioni da 7 a 9 in cui le colture agricole sono cereali, fruttiferi, agrumi, leguminose, orticole, cucurbitacee, piante oleoginose, tabacco, caffè, tè, cacao, barbabietola da zucchero, canna da zucchero, cotone.
- 12) Uso secondo una qualsiasi delle rivendicazioni da 7 a 9 per il controllo di Plasmopara viticola su vite; Phytophtora infestans e Botrytis Cinerea su pomodoro; Puccinia recondita , Erisiphae graminis , Helminthosporium teres, Septoria nodorum e Fusarium spp . su cereali; Phakopsora pachyrhizi su soia; Uromyces Appendiculatus su fagiolo; Venturia inaequalis su melo; Sphaerotheca fuliginea su cetriolo.
- 13) Uso dei composti secondo una qualsiasi delle rivendicazioni 1-3 o di composizioni secondo una qualsiasi delle rivendicazioni da 4 a 6 per il controllo di batteri e virus fitopatogeni .
- 14) Metodo per il controllo di funghi fitopatogeni in colture agricole, che consiste nell'applicazione di dosi efficaci di composti secondo una qualsiasi delle rivendicazioni 1-3, in quantità comprese tra 10 g e 5 kg per ettaro di coltura agricola.
Priority Applications (6)
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IT001564A ITMI20101564A1 (it) | 2010-08-23 | 2010-08-23 | Fenilammidine ad elevata attivita' fungicida e relativo uso |
EP11749396.5A EP2608666A1 (en) | 2010-08-23 | 2011-08-18 | Phenylamidines having a high fungicidal activity and use thereof |
BR112013004220A BR112013004220B1 (pt) | 2010-08-23 | 2011-08-18 | fenilamidinas tendo uma atividade fungicida alta e seu uso. |
PCT/EP2011/064210 WO2012025450A1 (en) | 2010-08-23 | 2011-08-18 | Phenylamidines having a high fungicidal activity and use thereof |
US13/818,622 US9040457B2 (en) | 2010-08-23 | 2011-08-18 | Phenylamidines having a high fungicidal activity and use thereof |
ARP110103049A AR082519A1 (es) | 2010-08-23 | 2011-08-23 | Fenilamidinas que tienen alta actividad fungicida, y su utilizacion |
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IT001564A ITMI20101564A1 (it) | 2010-08-23 | 2010-08-23 | Fenilammidine ad elevata attivita' fungicida e relativo uso |
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US (1) | US9040457B2 (it) |
EP (1) | EP2608666A1 (it) |
AR (1) | AR082519A1 (it) |
BR (1) | BR112013004220B1 (it) |
IT (1) | ITMI20101564A1 (it) |
WO (1) | WO2012025450A1 (it) |
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ITMI20120405A1 (it) * | 2012-03-15 | 2013-09-16 | Chemtura Corp | "composizioni sinergiche ad attivita' fungicida e relativo uso" |
WO2014130409A2 (en) | 2013-02-21 | 2014-08-28 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazole mixtures |
WO2015157005A1 (en) | 2014-04-10 | 2015-10-15 | E I Du Pont De Nemours And Company | Substituted tolyl fungicide mixtures |
EP3215491B1 (en) * | 2014-11-06 | 2018-08-29 | Syngenta Participations AG | Novel fungicidal pyridylamidines |
US10252977B2 (en) | 2015-06-15 | 2019-04-09 | Bayer Cropscience Aktiengesellschaft | Halogen-substituted phenoxyphenylamidines and the use thereof as fungicides |
HUE051950T2 (hu) | 2015-06-15 | 2021-04-28 | Bayer Cropscience Ag | Halogén-szubsztituált fenoxifenilamidinok és alkalmazásuk fungicidként |
CA2991436A1 (en) | 2015-07-08 | 2017-01-12 | Bayer Cropscience Aktiengesellschaft | Phenoxyhalogenphenylamidines and the use thereof as fungicides |
JP2019505492A (ja) * | 2015-12-15 | 2019-02-28 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物フェニルアミジン誘導体 |
EP3335559A1 (en) | 2016-12-14 | 2018-06-20 | Bayer CropScience Aktiengesellschaft | Active compound combinations |
WO2018109002A1 (en) | 2016-12-14 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Active compound combinations |
KR20190097125A (ko) | 2016-12-14 | 2019-08-20 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 페녹시페닐아미딘 및 살균제로서의 이들의 용도 |
BR112019012272A2 (pt) | 2016-12-14 | 2019-12-03 | Bayer Ag | fenilamidinas e seu uso como fungicidas |
US11051513B2 (en) | 2017-01-26 | 2021-07-06 | Mitsui Chemicals Agro, Inc. | Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients |
IT201700033543A1 (it) * | 2017-03-27 | 2018-09-27 | Isagro Spa | Piridil-formammidine ad attività fungicida, loro composizioni agronomiche e relativo uso |
WO2018190350A1 (ja) | 2017-04-10 | 2018-10-18 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
TWI793113B (zh) | 2017-04-10 | 2023-02-21 | 日商三井化學Agro股份有限公司 | 吡啶酮化合物及以吡啶酮化合物作為有效成分的農園藝用殺菌劑 |
UA126399C2 (uk) | 2017-04-11 | 2022-09-28 | Міцуі Кемікалз Агро, Інк. | Піридони і сільськогосподарські і садові фунгіциди, які їх містять, як активні інгредієнти |
AU2018254010B2 (en) | 2017-04-20 | 2022-05-12 | Pi Industries Ltd. | Novel phenylamine compounds |
EP3625215B1 (en) | 2017-05-18 | 2023-09-13 | PI Industries Ltd | Formimidamidine compounds useful against phytopathogenic microorganisms |
EP3636636B1 (en) | 2017-06-08 | 2022-07-06 | Mitsui Chemicals Agro, Inc. | Pyridone compound and agricultural and horticultural fungicide |
WO2020022412A1 (ja) | 2018-07-25 | 2020-01-30 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
EP3708565A1 (en) | 2020-03-04 | 2020-09-16 | Bayer AG | Pyrimidinyloxyphenylamidines and the use thereof as fungicides |
EP3915971A1 (en) | 2020-12-16 | 2021-12-01 | Bayer Aktiengesellschaft | Phenyl-s(o)n-phenylamidines and the use thereof as fungicides |
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- 2011-08-18 US US13/818,622 patent/US9040457B2/en not_active Expired - Fee Related
- 2011-08-18 WO PCT/EP2011/064210 patent/WO2012025450A1/en active Application Filing
- 2011-08-18 BR BR112013004220A patent/BR112013004220B1/pt not_active IP Right Cessation
- 2011-08-18 EP EP11749396.5A patent/EP2608666A1/en not_active Withdrawn
- 2011-08-23 AR ARP110103049A patent/AR082519A1/es active IP Right Grant
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WO2007031523A1 (en) * | 2005-09-13 | 2007-03-22 | Bayer Cropscience Ag | Fungicide pyridinyloxy substituted phenylamidine derivatives |
WO2007031524A1 (en) * | 2005-09-13 | 2007-03-22 | Bayer Cropscience Ag | Pesticide pyrimidinyloxy substituted phenylamidine derivatives |
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WO2012025450A1 (en) | 2012-03-01 |
EP2608666A1 (en) | 2013-07-03 |
AR082519A1 (es) | 2012-12-12 |
US20130157851A1 (en) | 2013-06-20 |
BR112013004220A2 (pt) | 2016-05-10 |
BR112013004220B1 (pt) | 2018-08-28 |
US9040457B2 (en) | 2015-05-26 |
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