ITMI20010446A1 - PHENYLPIRROLS WITH HERBICIDE ACTIVITY - Google Patents

PHENYLPIRROLS WITH HERBICIDE ACTIVITY Download PDF

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ITMI20010446A1
ITMI20010446A1 ITMI20010446A ITMI20010446A1 IT MI20010446 A1 ITMI20010446 A1 IT MI20010446A1 IT MI20010446 A ITMI20010446 A IT MI20010446A IT MI20010446 A1 ITMI20010446 A1 IT MI20010446A1
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chloro
alkyl
dichloro
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Giovanni Meazza
Franco Bettarini
Paolo Castoro
Porta Piero La
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Isagro Ricerca Srl
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Priority to PCT/EP2002/002297 priority patent/WO2002070476A1/en
Publication of ITMI20010446A1 publication Critical patent/ITMI20010446A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/38—2-Pyrrolones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

FENILPIRROLI AD ATTIVITÀ' ERBICIDA PHENYLPYRROLS WITH HERBICIDE ACTIVITY

DESCRIZIONE DESCRIPTION

La presente invenzione riguarda nuovi fenilpirroli. Più in particolare la presente invenzione riguarda nuovi fenilpirroli aventi elevata attività erbicida, i procedimenti per la loro preparazione ed il loro impiego come erbicidi per il controllo di erbe infestanti in colture agricole. The present invention relates to new phenylpyrroles. More particularly, the present invention relates to new phenylpyrroles having a high herbicidal activity, the processes for their preparation and their use as herbicides for the control of weeds in agricultural crops.

Fenilpirroli ad attività erbicida sono descritti nella domanda di brevetto europea EP 1061072. Phenylpyrroles with herbicidal activity are described in European patent application EP 1061072.

La Richiedente ha ora trovato nuovi fenilpirroli che, rispetto ai prodotti descritti nella domanda di brevetto sopracitata, presentano caratteristiche migliorate in termini di attività erbicida nei confronti delle erbe infestanti e/o di minore fitotossicità per le colture di interesse agrario. Costituiscono pertanto l' oggetto della presente invenzione nuovi fenilpirroli aventi formula generale (I): The Applicant has now found new phenylpyrroles which, compared to the products described in the aforementioned patent application, have improved characteristics in terms of herbicidal activity against weeds and / or less phytotoxicity for crops of agricultural interest. Therefore, the object of the present invention is new phenylpyrroles having general formula (I):

( I ) (I)

in cui: in which:

- R ed R1, uguali o diversi tra loro, rappresentano un gruppo alchilico od aloalchilico C1-C4; - R and R1, the same or different from each other, represent a C1-C4 alkyl or haloalkyl group;

- X ed ∑i, uguali o diversi tra loro, rappresentano un atomo di alogeno; - X and ∑i, the same or different from each other, represent a halogen atom;

- X2 rappresenta un atomo di idrogeno od un atomo di alogeno; - X2 represents a hydrogen atom or a halogen atom;

- Y rappresenta un atomo di alogeno, un gruppo aloalchilico od aloalcossilico C1-C4, un gruppo ciano, un gruppo nitro; - Y represents a halogen atom, a C1-C4 haloalkyl or haloalkoxyl group, a cyano group, a nitro group;

- W rappresenta uno dei seguenti raggruppamenti: - W represents one of the following groupings:

; ;

in cui: in which:

- Ra ed Rb , uguali o diversi tra loro, rappresentano un atomo di idrogeno od un gruppo alchilico C1-C4; R2 rappresenta: un gruppo alchenilico C3-C6 eventualmente sostituito da gruppi alcossilici Ci-C4; un gruppo alchinilico C3-C6 eventualmente sostituito da gruppi alcossilici C1-C4; un gruppo alcossialchilico od alchiltioalchilico C2-C8; un gruppo cicloalchilico C3-C8 o cicloalchilalchilico C4-C10 eventualmente sostituito da gruppi alchilici C1-C4 ed eventualmente interrotto da atomi di ossigeno; un gruppo alchilamminoalchilico C2-C8 od un gruppo dialchilamminoalchilico C4-C12; un gruppo 4-morfolilalchilico C5-C9; un gruppo 1-pirrolidilalchilico C5-C9; un gruppo 1-piperidilalchilico C6-C10; un gruppo 2-pirrolidinonilalchilico C3-C9; un gruppo alchilcarbonilammino-alchilico C3-C9; un gruppo alchilcarbonilossialchilico C4-C9; un gruppo alcossicarbonilalchilico C3-C10; un gruppo alchenil -ossicarbonilalchilico C4-C12; un gruppo alchinilossicarbonilalchilico C4-C12; un gruppo alcossialcossicarbonilalchilico C4-C12; un gruppo cicloalcossicarbonilalchilico C5-C10; un gruppo cicloalchilalcossicarbonilalchilico C6-C12; tutti questi gruppi a loro volta possono essere sostituiti da atomi di alogeno; oppure rappresenta un gruppo arilico, arilalchilico, arilossialchilico eteroarilico, eteroarilalchilico eteroarilossialchilico, arilamminoalchilico, eteroarilamminoalchilico, tutti gruppi eventualmente sostituiti da gruppi C1-C4 alchilici, aloalchilici, alcossilici,aloalcossilici, da atomi di alogeno, da gruppi nitro, da gruppi ciano; - Ra and Rb, the same or different from each other, represent a hydrogen atom or a C1-C4 alkyl group; R2 represents: a C3-C6 alkenyl group optionally substituted by C1-C4 alkoxy groups; a C3-C6 alkynyl group optionally substituted by C1-C4 alkoxy groups; a C2-C8 alkoxyalkyl or alkylthioalkyl group; a C3-C8 cycloalkyl group or C4-C10 cycloalkylalkyl group optionally substituted by C1-C4 alkyl groups and optionally interrupted by oxygen atoms; a C2-C8 alkylaminoalkyl group or a C4-C12 dialkylaminoalkyl group; a C5-C9 4-morpholylalkyl group; a C5-C9 1-pyrrolidylalkyl group; a C6-C10 1-piperidylalkyl group; a C3-C9 2-pyrrolidinonylalkyl group; a C3-C9 alkylcarbonylamino-alkyl group; a C4-C9 alkylcarbonyloxyalkyl group; a C3-C10 alkoxycarbonylalkyl group; a C4-C12 alkenyl -oxycarbonylalkyl group; a C4-C12 alkynyloxycarbonylalkyl group; a C4-C12 alkoxyalkoxycarbonylalkyl group; a C5-C10 cycloalkoxycarbonylalkyl group; a C6-C12 cycloalkylalkoxycarbonylalkyl group; all these groups in turn can be replaced by halogen atoms; or it represents an aryl, arylalkyl, aryloxyalkyl heteroaryl, heteroarylalkyl heteroaryloxyalkyl, arylaminoalkyl, heteroarylaminoalkyl groups, all groups possibly substituted by C1-C4 alkyl groups, haloalkyl, alkoxy, haloalkyloxyl groups, by alkoxy nitrogen groups, by atoms of nitrogen groups;

R3 rappresenta un gruppo alchenilico od alchinilico C3-C6 eventualmente sostituito da gruppi alcossilici C1-C4 ed eventualmente alogenato; un gruppo alcossialchilico od alchiltioalchilico C2-C8 eventualmente alogenato; un gruppo cicloalchilico C3-C8 o cicloalchilalchilico C4-C10 eventualmente sostituito da gruppi alchilici od aloalchilici C1-C4, eventualmente alogenato ed eventualmente interrotto da atomi di ossigeno; un gruppo alchilafimino-alchilico C3-C8 od un gruppo dialchilamminoalchilico C4-C12 eventualmente alogenato; un gruppo alcossicarbonilalchilico C3-C8 eventualmente alogenato; un gruppo OH; un gruppo alcossilico od aloalcossilico C1-C6; un gruppo alchilcarbonilossi od aloalchilcarbonilossi C2-C7; oppure rappresenta un gruppo arilico, arilalchilico, arilossialchilico eteroarilico, eteroarilalchilico, eteroarilossialchilico, arilamminoalchilico, eteroarilamminoalchilico, tutti gruppi eventualmente sostituiti da gruppi C1-C4 alchilici, aloalchilici, alcossilici, aloalcossilici, da atomi di alogeno, da gruppi nitro, da gruppi ciano; R3 represents a C3-C6 alkenyl or alkynyl group optionally substituted by C1-C4 alkoxy groups and optionally halogenated; a C2-C8 alkoxyalkyl or alkylthioalkyl group optionally halogenated; a C3-C8 cycloalkyl group or C4-C10 cycloalkylalkyl group optionally substituted by C1-C4 alkyl or haloalkyl groups, optionally halogenated and optionally interrupted by oxygen atoms; a C3-C8 alkylaminoalkyl group or a C4-C12 dialkylaminoalkyl group optionally halogenated; a C3-C8 alkoxycarbonylalkyl group optionally halogenated; an OH group; a C1-C6 alkoxy or haloalkoxy group; a C2-C7 alkylcarbonyloxy or haloalkylcarbonyloxy group; or it represents an aryl, arylalkyl, aryloxyalkyl heteroaryl, heteroarylalkyl, heteroaryloxyalkyl, arylaminoalkyl, heteroarylaminoalkyl groups, all groups optionally substituted by C1-C4 alkyl groups, haloalkyl, alkoxy, haloalkyloxyl groups, by nitroalkyloxyl groups;

- R4 rappresenta: un atomo di idrogeno; un gruppo alchilico od aloalchilico C1-C6; un gruppo alchenilico od aloalchenilico C3-C6 eventualmente sostituito da gruppi alcossilici od aloalcossilici C1-C4; un gruppo alchinilico od alo-alchinilico C3-C6 eventualmente sostituito da gruppi alcossilici od alo-alcossilici C1-C4; un gruppo alcossialchilico od aloalcossialchilico C2-C8; - R4 represents: a hydrogen atom; a C1-C6 alkyl or haloalkyl group; a C3-C6 alkenyl or haloalkenyl group optionally substituted by C1-C4 alkoxy or haloalkoxyl groups; a C3-C6 alkynyl or halo-alkynyl group optionally substituted by C1-C4 alkoxy or halo-alkoxy groups; a C2-C8 alkoxyalkyl or haloalkoxyalkyl group;

- Z rappresenta un atomo di ossigeno od un atomo di zolfo; - Z represents an oxygen atom or a sulfur atom;

- m rappresenta un numero intero compreso tra 1 e 4; - n rappresenta zero oppure 1; - m represents an integer between 1 and 4; - n represents zero or 1;

- p rappresenta 1 oppure 2; - p represents 1 or 2;

- K rappresenta un atomo di ossigeno oppure un gruppo NRK in cui: - K represents an oxygen atom or an NRK group in which:

- Rk rappresenta un atomo di idrogeno, un gruppo OH, un gruppo alcossilico od aloalcossilico CiC6, un gruppo alchilcarbonilossi C2-C6 eventualmente alogenato, un gruppo alchenilico od alchinilico C3-C6 eventualmente sostituito d a gruppi alcossilici od aloalcossilici C1-C4 ed eventualmente alogenato; un gruppo alcossialchilico C2-C8 eventualmente alogenato; un gruppo cicloalchilico C3-C8 o cicloalchilalchilico C4-C10 eventualmente sostituito da gruppi alchilici od aloalchilici Ci-C4, eventualmente alogenato ed eventualmente interrotto da atomi di ossigeno; un gruppo alchilammino-alchilico C3-C8 od un gruppo dialchilamminoalchilico C4-C12 eventualmente alogenato. - Rk represents a hydrogen atom, an OH group, a C1-C4 alkoxy or haloalkoxy group, a C2-C6 alkylcarbonyloxy group optionally halogenated, a C3-C6 alkenyl or alkynyl group optionally substituted by C1-C4 alkoxyl or haloalkoxyl groups and possibly halogenated; a C2-C8 alkoxyalkyl group optionally halogenated; a C3-C8 cycloalkyl group or C4-C10 cycloalkylalkyl group optionally substituted by C1-C4 alkyl or haloalkyl groups, optionally halogenated and optionally interrupted by oxygen atoms; a C3-C8 alkylamino-alkyl group or a C4-C12 dialkylaminoalkyl group optionally halogenated.

in W2, quando n = l: in W2, when n = l:

R3 ed R4 insieme possono anche rappresentare una catena alchilenica C2-C7 eventualmente sostituita da gruppi alchilici Ci-C4 ed eventualmente interrotta da atomi di ossigeno o da un gruppo NRS in cui: R3 and R4 together can also represent a C2-C7 alkylene chain possibly replaced by C1-C4 alkyl groups and possibly interrupted by oxygen atoms or by an NRS group in which:

R5 rappresenta un atomo di idrogeno, un gruppo alchilico od aloalchilico C1-C6, un gruppo alchenilico od aloalchenilico C3-C6, un gruppo alchinilico od aloalchinilico C3-C6, un gruppo alcossialchilico od aloalcossialchilico C2-C8 , un gruppo alchilcarboni1ico od aloalchilcarbonilico C2-C7; R5 represents a hydrogen atom, a C1-C6 alkyl or haloalkyl group, a C3-C6 alkenyl or haloalkenyl group, a C3-C6 alkynyl or haloalkynyl group, a C2-C8 alkoxyalkyl or haloalkoxyalkyl group, a C2-C8 alkylcarbonyl or haloalkyl group C7;

Alternativamente, il gruppo W ed il gruppo Y insieme possono rappresentare una catena —N (Re)OCCR7R8O— in cui: Alternatively, group W and group Y together can represent a chain —N (Re) OCCR7R8O— in which:

Re rappresenta un atomo di idrogeno, un gruppo alchilico od aloalchilico C1-C6, un gruppo alchenilico od aloalchenilico C3-C6 eventualmente sostituito da gruppi alcossilici od aloalcossilici C1-C4, un gruppo alchinilico od alo-alchinilico C3-C6 eventualmente sostituito d a g ruppi alcossilici od aloalcossilici C1-C4, un gruppo alcossialchilico od aloalcossialchilico C2-C8; Re represents a hydrogen atom, a C1-C6 alkyl or haloalkyl group, a C3-C6 alkenyl or haloalkenyl group optionally substituted by C1-C4 alkoxyl or haloalkoxyl groups, a C3-C6 alkynyl or halo-alkynyl group optionally substituted by alkoxy groups or C1-C4 haloalkoxyls, a C2-C8 alkoxyalkyl or haloalkoxyalkyl group;

- R7 ed Re, uguali o diversi tra loro, rappresentano un atomo di idrogeno oppure un gruppo alchilico od aloalchilico C1-C4. - R7 and Re, the same or different from each other, represent a hydrogen atom or a C1-C4 alkyl or haloalkyl group.

Come affermato in precedenza, i pirroli di formula generale (I) sono dotati di elevata attività erbicida. As previously stated, the pyrroles of general formula (I) are endowed with a high herbicidal activity.

Esempi specifici di composti di formula generale (I) interessanti per la loro attività sono: Specific examples of compounds of general formula (I) interesting for their activity are:

- 2-propenil [2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi]acetato; 3,3-dicloro-2-propenil [2-cloro-5-(2,4-dicloro-lmetil-5-trifluorometil-pirrol-3-il) -4-f luorofenossi] acetato; - 2-propenyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate; 3,3-dichloro-2-propenyl [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

2-metil -2-propenil [2-cloro-5- (2,4-dicloro-lmetil--5-trifluorometil-pirrol-3-il) -4-luorofenossi]acetato ; 2-methyl-2-propenyl [2-chloro-5- (2,4-dichloro-1methyl - 5-trifluoromethyl-pyrrol-3-yl) -4-luorophenoxy] acetate;

2-propinil [2-cloro-5- (2,4-dicloro-l-metil-5-trifluorometil -pirrol -3-il) -4-fluoro-fenos -si]acetato; 2-propinyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol -3-yl) -4-fluoro-phenos-si] acetate;

- 2-propinil [2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluoro- feniltio] acetato ; - 2-propinyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-phenylthio] acetate;

- 3-butin-2-il [2-cloro-5- (2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetato; - 3-butin-2-yl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

- 2-metil-3-butin-2-il [2-cloro-5- (2,4-dicloro-lmetil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetato; - 2-methyl-3-butin-2-yl [2-chloro-5- (2,4-dichloro-lmethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

- 4-metossibut-2-inil [2-cloro-5- (2,4-dicloro-lmetil -5-trifluoromet il-pirrol -3-il) -4-fluoro fenossi] acetato; - 4-methoxybut-2-yl [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-phenoxy] acetate;

- ciclopropilmetil [2-Cloro-5- (2,4-dicloro-l-metil-5-trif luorometil-pirrol-3-il) -4-fluorofenossi] acetato; - cyclopropylmethyl [2-Chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

ciclobutilmetil [2-cloro-5- (2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetato; cyclobutylmethyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

ciclopentil [2-cloro-5- (2,4-dicloro-l-metil-5-trif luorometil-pirrol-3-il) -4-fluorofenossi] acetato; cyclopentyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

3-ossetanil [2-cloro-5- (2,4-dicloro-l-metil-5-trif luorometil -pirrol-3 -il)-4-fluorofenossi] acetato; 3-oxetanil [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3 -yl) -4-fluorophenoxy] acetate;

2,3 -epossipropil [2-cloro-5- (2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetato ; 2,3-epoxypropyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

2-etiltioetil [2-cloro-5- (2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetato; 2-ethylthioethyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

2- (4-morfolil) etil [2-cloro-5- (2,4-dicloro- 1-met il-5-trif luorometil -pirrol-3-il) -4-fluorofenossi] acetato; 2- (4-morpholyl) ethyl [2-chloro-5- (2,4-dichloro- 1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

2- (1-pirrolidil) etil [2-cloro-5- (2,4-dicloro-lmetil-5-trif luorometil-pirrol- 3 -il)-4-fluorofenossi] acetato; 2- (1-pyrrolidyl) ethyl [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol- 3 -yl) -4-fluorophenoxy] acetate;

2- (2-pirrolidinonil) etil [2-cloro-5- (2,4-diclorol-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi]acetato; 2- (2-pyrrolidinonyl) ethyl [2-chloro-5- (2,4-dichlorol-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

2-acetilamminoetil [2-cloro-5-(2,4-dicloro-lmetil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetato; 2-acetylaminoethyl [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

- 2-acetilossietil [2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi] acetato; - 2-acetyloxyethyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

- 2-propenil [2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il) -4-fluoro-fenossi] acetato; - 2-propinil [2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il)-4-fluoro-fenossi] acetato; - 2-propenyl [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-phenoxy] acetate; - 2-propinyl [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-phenoxy] acetate;

- 3-butin-2-il [2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il)-4-fluoro-fenossi] acetato; - 3-butin-2-yl [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-phenoxy] acetate;

2-metil-3-butin-2-il [2-cloro-5-(2,4-dicloro-letil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi]acetato; 2-methyl-3-butin-2-yl [2-chloro-5- (2,4-dichloro-letyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

- 4-metossibut-2-inil [2-cloro-5-(2,4-dicloro-l-etil-5-trif luorometil-pirrol-3-il)-4-fluorofenossi] acetato; - 4-methoxybut-2-yl [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

- ciclopropilmetil [2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi] acetato; - cyclopropylmethyl [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

2-metossietil [2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi] acetato; 2-methoxyethyl [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

3-ossetanil [2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il)-4-fluoro-fenossi] acetato; 3-oxetanyl [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-phenoxy] acetate;

- 2,3-epossipropil [2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi] acetato; - 2,3-epoxypropyl [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate;

2-propenil 2-cloro-5- (2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluoro-benzoato ; 2-propenyl 2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-benzoate;

2-propinil 2-cloro-5- {2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluoro-benzoato ; 2-propinyl 2-chloro-5- {2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-benzoate;

- 3-butin-2-il 2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluorobenzoato ; - 3-butin-2-yl 2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorobenzoate;

- 2-metil-3-butin-2-il 2-cloro-5-(2,4-dicloro-l-metil -5-trifluorometil-pirrol-3-il)-4-fluorobenzoato; - 4-metossibut-2-inil 2-cloro-5-(2,4-dicloro-l-metil-5-trifbuorometil-pirrol-3-il)-4-fluorobenzoato ; ciclopropilmetil 2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluorobenzoato; - 2-metossietil 2-cloro-5- (2 , 4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4 - fluorobenzoato ; - 2-methyl-3-butin-2-yl 2-chloro-5- (2,4-dichloro-1-methyl -5-trifluoromethyl-pyrrol-3-yl) -4-fluorobenzoate; - 4-methoxybut-2-yl 2-chloro-5- (2,4-dichloro-1-methyl-5-trifbuoromethyl-pyrrol-3-yl) -4-fluorobenzoate; cyclopropylmethyl 2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorobenzoate; - 2-methoxyethyl 2-chloro-5- (2, 4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4 - fluorobenzoate;

1-(etossicarbonil)etil 2-cloro-5-(2,4-dicloro-lmetil-5-trifluorometil-pirrol-3-il) -4-fluorobenzoato ; 1- (ethoxycarbonyl) ethyl 2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorobenzoate;

- 2-(2-propenilossicarbonil)prop-2-il 2-cloro-5-2 ,4-dicloro-l-metil-5-trifluoro-metil-pirrol-3-il) -4-fluorobenzoato ; - 2- (2-propenyloxycarbonyl) prop-2-yl 2-chloro-5-2, 4-dichloro-1-methyl-5-trifluoro-methyl-pyrrol-3-yl) -4-fluorobenzoate;

- 2- (2-propenilossicarbonil) prop-2-il 2-cloro-5-2 ,4-dicloro-l-metil-5-trif luoro-metil-pirrol-3-il) benzoato ; - 2- (2-propenyloxycarbonyl) prop-2-yl 2-chloro-5-2, 4-dichloro-1-methyl-5-trifluoro-methyl-pyrrol-3-yl) benzoate;

- 2- (2-propenilossicarbonil) prop-2-il 2-cloro-5-2 ,4-dicloro-l-etil-5-trifluoro-metil-pirrol-3-il)benzoato; - 2- (2-propenyloxycarbonyl) prop-2-yl 2-chloro-5-2, 4-dichloro-1-ethyl-5-trifluoro-methyl-pyrrol-3-yl) benzoate;

- N-metossi- [2-cloro-5- (2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetammide ; - N-methoxy- [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide;

- N-metil-N-metossi- [2-cloro-5- (2,4-dicloro-l-metil-5-trif luorometil-pirrol-3-il) -4-fluorofenossi] acetammide ; - N-methyl-N-methoxy- [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide;

N-(2-propinil) - [2-cloro-5- (2,4-dicloro-l-metil-5-trif luorometil -pirrol-3 -il)-4-fluorofenossi] acetammide ; N- (2-propynyl) - [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3 -yl) -4-fluorophenoxy] acetamide;

- N-metil-N- (2-propinil) -[2-cloro-5- (2,4-dicloro-lmetil-5-trifluorometil-pirrol-3-il) -4-fluoro fenossi] acetammide; - N-methyl-N- (2-propinyl) - [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-phenoxy] acetamide;

- N- (2-propenil) -[2-cloro-5- (2,4-dicloro-l-metil-5trifluorometil-pirrol-3-il)-4-fluorofenossi] acetammide; - N- (2-propenyl) - [2-chloro-5- (2,4-dichloro-1-methyl-5trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide;

- N-ciclopropilmetil-[2-cloro-5-(2,4-dicloro-lmetil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi]acetammide; - N-cyclopropylmethyl- [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide;

- N-(2-metossietil)-[2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi] acetammide; - N- (2-methoxyethyl) - [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide;

- N-metil-N-(2-metossietil)-[2-cloro-5-(2,4-diclorol-metil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi]acetammide; - N-methyl-N- (2-methoxyethyl) - [2-chloro-5- (2,4-dichlorol-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide;

- N-(etossicarbonilmetil)-[2-cloro-5-(2,4-dicloro-lmetil-5-trifluorometil-pirrol-3-il)-4-fluoro fenossi]acetammide; - N- (ethoxycarbonylmethyl) - [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-phenoxy] acetamide;

- 4-[2-cloro-5-(2,4-dicloro-l-metil-5-trifluoro metil-pirrol-3-il)-4-fluorofenossi-acetil] morfelina; - 4- [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoro methyl-pyrrol-3-yl) -4-fluorophenoxy-acetyl] morpheline;

1-[2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi-acetil] pirrolidina; 1- [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy-acetyl] pyrrolidine;

- N-metossi- [2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il)-4-fluoro-fenossi] acetammide; - N-methoxy- [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-phenoxy] acetamide;

- N-metil-N-metossi-[2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi] acetammide; - N-methyl-N-methoxy- [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide;

- N-(2-propinil)-[2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi] acetammide; - N- (2-propinyl) - [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide;

- N-metil-N-(2-propinil)-[2-cloro-5-(2,4-dicloro-letil-5-trifluorometil-pirrol-3-il)-4-luorofenossi] acetammide; - N-methyl-N- (2-propinyl) - [2-chloro-5- (2,4-dichloro-letyl-5-trifluoromethyl-pyrrol-3-yl) -4-luorophenoxy] acetamide;

- N-(2-propenil)-[2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi] acetammide; - N- (2-propenyl) - [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide;

- N-ciclopropilmetil-(2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi] acetammide; - N-cyclopropylmethyl- (2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide;

- N-(2-metossietil)-[2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi] acetammide; - N- (2-methoxyethyl) - [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide;

- N-metil-N-(2-metossietil)- [2-cloro-5-(2,4-diclorol-etil-5-trifluorometil-pirrol-3-il)-4-fluoro fenossi]acetammide; - N-methyl-N- (2-methoxyethyl) - [2-chloro-5- (2,4-dichlorol-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-phenoxy] acetamide;

- N-(etossicarbonilmetil)- [2-cloro-5-(2,4-dicloro-letil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi] acetammide; - N- (ethoxycarbonylmethyl) - [2-chloro-5- (2,4-dichloro-letyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide;

- 4- [2-cloro-5- (2 , 4-dicloro-l-etil-5-trif luorometilpirrol-3-il) -4-f luorofenossi- acetil] morfolina; - 1- [2-cloro-5- (2,4-dicloro-l-etil-5-trifluorometilpirrol-3-il) -4-f luorofenossi- acetil] pirrolidina; - N-metossi- [2-cloro-5- {2 ,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluoro] benzairanide; - N-metil-N-metossi- [2-cloro-5- (2 , 4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-f luoro] benzairanide; - N- (2-propinil) - [2-cloro-5- (2, 4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-f luoro] benzairanide; - N-metil-N- (2-propinil) - [2-cloro-5- (2, 4-dicloro-lmetil-5-trifluorometil-pirrol-3-il) -4-fluoro] benzairanide ; - 4- [2-chloro-5- (2, 4-dichloro-1-ethyl-5-trifluoromethylpyrrol-3-yl) -4-fluorophenoxy-acetyl] morpholine; - 1- [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethylpyrrol-3-yl) -4-fluorophenoxy-acetyl] pyrrolidine; - N-methoxy- [2-chloro-5- {2, 4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro] benzairanide; - N-methyl-N-methoxy- [2-chloro-5- (2, 4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluor] benzairanide; - N- (2-propinyl) - [2-chloro-5- (2, 4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluor] benzairanide; - N-methyl-N- (2-propinyl) - [2-chloro-5- (2, 4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro] benzairanide;

- N- (2-propenil) - [2-cloro-5- (2 , 4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluoro] benzairanide; - N-ciclopropilmetil- [2-cloro-5- (2 , 4-dicloro-lmetil-5-trifluorometil-pirrol- 3 -il) -4-fluoro] benzairanide ; - N- (2-propenyl) - [2-chloro-5- (2, 4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro] benzairanide; - N-cyclopropylmethyl- [2-chloro-5- (2, 4-dichloro-1methyl-5-trifluoromethyl-pyrrol- 3 -yl) -4-fluoro] benzairanide;

- N- (2-metossietil) - [2 -cloro- 5- (2, 4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluoro] benzairanide; - N-metil-N- (2-metossietil) - [2-cloro-5- (2 , 4-dicloro-1 -met il - 5 - trif luorometil -pirrol - 3 - il ) -4-fluoro] benzairanide ; - N- (2-methoxyethyl) - [2 -chloro- 5- (2, 4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro] benzairanide; - N-methyl-N- (2-methoxyethyl) - [2-chloro-5- (2, 4-dichloro-1 -methyl - 5 - trifluoromethyl-pyrrol - 3 - yl) -4-fluoro] benzairanide;

- a-[2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi]-γ-butirro lattone; - a- [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] -γ-butyro lactone;

- 3-[2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi]-l-metil-2-pirrolidinone; - 3- [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] -1-methyl-2-pyrrolidinone;

- 6-[5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)]-7-fluoro-4-(2-propinil)-2H-1,4-benzossazin-3(4H)-one; - 6- [5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl)] - 7-fluoro-4- (2-propinyl) -2H-1,4-benzoxazin-3 (4H) -one;

- 6-[5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)]-4- (2-propinil)-2H-1,4-benzossazin-3(4H)-one. - 6- [5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl)] - 4- (2-propinyl) -2H-1,4-benzoxazin-3 (4H) - one.

Ulteriore oggetto della presente invenzione sono i procedimenti per la preparazione dei composti di formula generale (I). A further object of the present invention are the processes for the preparation of the compounds of general formula (I).

I composti di formula generale (I) in cui W rappresenta Wj oppure W2 possono essere preparati per condensazione di un fenilpirrolo di formula generale (II) con un alcool od un'ammina di formula generale (III), a dare un estere od un ammide di formula generale (la) secondo lo schema di reazione 1: The compounds of general formula (I) in which W represents Wj or W2 can be prepared by condensation of a phenylpyrrole of general formula (II) with an alcohol or an amine of general formula (III), to give an ester or an amide of general formula (la) according to the reaction scheme 1:

Schema 1: Scheme 1:

Nelle formule generali riportate in questo schema di reazione : In the general formulas given in this reaction scheme:

- R, Ri, X, Xi, X2 ed Y hanno i significati in precedenza definiti; - R, Ri, X, Xi, X2 and Y have the previously defined meanings;

- A rappresenta un gruppo in cui Ra, Rb, m ed n hanno i significati in precedenza definiti, L rappresenta un atomo di alogeno od un gruppo OH; - A represents a group in which Ra, Rb, m and n have the previously defined meanings, L represents a halogen atom or an OH group;

- Q rappresenta un gruppo R20- od un gruppo R3N(R4)-in cui R2, R3 ed R4 - Q represents a group R20- or a group R3N (R4) -in which R2, R3 and R4

hanno i significati precedentemente definiti; have the previously defined meanings;

- Wa rappresenta un gruppo Wi od un gruppo W2 come definiti in precedenza. - Wa represents a Wi group or a W2 group as defined above.

In generale, la reazione rappresentata nello schema 1 può essere condotta secondo le varie modalità operative descritte nella letteratura chimica per la preparazione di esteri ed ammidi mediante condensazione di cloruri acilici od acidi carbossilici con alcoli ed animine primarie o secondarie (vedere, ad esempio: J. March, "Advanced Organic Chemistry", 4a edizione, John Wiley & Sons, New York e riferimenti ivi citati). In general, the reaction represented in scheme 1 can be carried out according to the various operating modes described in the chemical literature for the preparation of esters and amides by condensation of acyl chlorides or carboxylic acids with primary or secondary alcohols and amines (see, for example: J . March, "Advanced Organic Chemistry", 4th edition, John Wiley & Sons, New York and references cited therein).

Ad esempio, quando si parte da un cloruro acilico (L=C1) la reazione con un alcol od un'ammina di formula generale (III) viene preferibilmente condotta in uno o più solventi inerti, in presenza di una base organica od inorganica, ad una temperatura compresa tra i - 20°C e la temperatura di ebollizione della miscela di reazione. For example, when starting from an acyl chloride (L = C1) the reaction with an alcohol or an amine of general formula (III) is preferably carried out in one or more inert solvents, in the presence of an organic or inorganic base, to a temperature between - 20 ° C and the boiling temperature of the reaction mixture.

Esempi di solventi utilizzabili per la succitata reazione includono l'acqua, gli idrocarburi alifatici o cicloalifatici (etere di petrolio, esano, cicloesano ecc.), gli idrocarburi clorurati (cloruro di metilene, cloroformio, tetracloruro di carbonio, dicloroetano, ecc), gli idrocarburi aromatici (benzene, toluene, xilene, clorobenzene, ecc.), gli eteri -dietil etere, diisopropil etere, dimetossietano, diossano, tetraidrofurano, ecc.), i chetoni (acetone, metiletilchetone, metilpropilchetone, metilisobutilchetone, ecc.), i nitrili (acetonitrile, benzonitrile, ecc.), i solventi dipolari aprotici (dimetilformammide, dimetilacetammide, esametil-fosforotriammide, dimetilsolfossido, solfolano, N-metilpirrolidone, ecc.). Examples of solvents that can be used for the aforementioned reaction include water, aliphatic or cycloaliphatic hydrocarbons (petroleum ether, hexane, cyclohexane, etc.), chlorinated hydrocarbons (methylene chloride, chloroform, carbon tetrachloride, dichloroethane, etc.), aromatic hydrocarbons (benzene, toluene, xylene, chlorobenzene, etc.), the ethers -diethyl ether, diisopropyl ether, dimethoxyethane, dioxane, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, methyl propyl ketone, methyl isobutyl ketone, etc.) nitriles (acetonitrile, benzonitrile, etc.), aprotic dipolar solvents (dimethylformamide, dimethylacetamide, hexamethylphosphorotriamide, dimethylsulfoxide, sulfolane, N-methylpyrrolidone, etc.).

Basi inorganiche utili allo scopo sono, ad esempio, idrossidi, carbonati e bicarbonati di sodio o potassio. Inorganic bases useful for this purpose are, for example, sodium or potassium hydroxides, carbonates and bicarbonates.

Basi organiche utili allo scopo sono, ad esempio, trietilammina, piridina, 4-dimetilamminopiridina, diazabicicloottano (DABCO) , diazabiciclononene (DBN), diazabicicloundecene (DBU) . Organic bases useful for this purpose are, for example, triethylamine, pyridine, 4-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN), diazabicicloundecene (DBU).

I composti di formula generale (I) in cui W rappresenta un gruppo W3, come pure, in alternativa al metodo precedentemente descritto, i composti in cui W rappresenta un gruppo Wj od un gruppo W2 ed n = 1, possono essere preparati per eterificazione di un fenolo o tiofenolo di formula generale (IV) con un composto di formula generale (V) a dare composti di formula generale (Ib), secondo lo schema di reazione 2: The compounds of general formula (I) in which W represents a group W3, as well as, as an alternative to the method described above, the compounds in which W represents a group Wj or a group W2 and n = 1, can be prepared by etherification of a phenol or thiophenol of general formula (IV) with a compound of general formula (V) to give compounds of general formula (Ib), according to reaction scheme 2:

Schema 2: Scheme 2:

Nelle formule generali riportate in questo schema di reazione : In the general formulas given in this reaction scheme:

- R, Ri, X, X1, X2, Y e Z assumono i significati precedentemente definiti; - R, Ri, X, X1, X2, Y and Z take on the previously defined meanings;

- Qx rappresenta un gruppo oppure - Qx represents a group or

in cui R2/ R3, R4 ed m assumono i significati precedentemente definiti; in which R2 / R3, R4 and m take on the previously defined meanings;

- L1 rappresenta un atomo di alogeno, oppure un gruppo in cui RL rappresenta un gruppo alchilico od aloalchilico C1-C4 od un gruppo fenilico eventualmente sostituito da gruppi alchilici C1-C4. - L1 represents a halogen atom, or a group in which RL represents a C1-C4 alkyl or haloalkyl group or a phenyl group optionally substituted by C1-C4 alkyl groups.

- Wb rappresenta un gruppo W3 come sopra definito; oppure rappresenta un gruppo Wi od un gruppo W2, come definiti in precedenza, in cui n = 1. - Wb represents a W3 group as defined above; or it represents a Wi group or a W2 group, as defined above, where n = 1.

La reazione tra i composti di formula generale (IV) ed i composti di formula generale (V) viene preferibilmente condotta in presenza di uno o più solventi organici inerti ed in presenza di una base, preferibilmente inorganica, ad una temperatura compresa tra - 10°C e la temperatura di ebollizione della miscela di reazione. The reaction between the compounds of general formula (IV) and the compounds of general formula (V) is preferably carried out in the presence of one or more inert organic solvents and in the presence of a base, preferably inorganic, at a temperature between - 10 ° C is the boiling temperature of the reaction mixture.

Solventi organici utili allo scopo sono ad esempio gli idrocarburi aromatici (benzene, toluene, xilene, clorobenzene, ecc.), gli eteri (dietil etere, diisopropil etere, dimetossietano, diossano, tetraidrofurano, ecc.), gli alcoli ed i glicoli (metanolo, etanolo, metilcellosolve, glicole etilenico, ecc.), i chetoni (acetone, metiletilchetone, metilpropilchetone, metilisobutilchetone, ecc.), i nitrili ( acetonitrile, benzonitrile, ecc.), i solventi dipolari aprotici (dimetilformammide, dimetilacetammide, esametilfosforotriammide, dimetilsolfossido, solfolano, N-metilpirrolidone, ecc.). Organic solvents useful for this purpose are for example aromatic hydrocarbons (benzene, toluene, xylene, chlorobenzene, etc.), ethers (diethyl ether, diisopropyl ether, dimethoxyethane, dioxane, tetrahydrofuran, etc.), alcohols and glycols (methanol , ethanol, methylcellosolve, ethylene glycol, etc.), ketones (acetone, methylethylketone, methylpropylketone, methylisobutylketone, etc.), nitriles (acetonitrile, benzonitrile, etc.), aprotic dipolar solvents (dimethylformamide, dimethylacetamide , sulfolane, N-methylpyrrolidone, etc.).

Basi inorganiche utili allo scopo sono, ad esempio, idruri, idrossidi e carbonati di sodio o potassio. Inorganic bases useful for this purpose are, for example, hydrides, hydroxides and sodium or potassium carbonates.

La reazione può essere anche vantaggiosamente condotta in un sistema bifasico utilizzando come solventi 3⁄4 acqua ed un solvente organico immiscibile con essa, in presenza di catalizzatori di trasferimento di fase, secondo quanto descritto da Dehmlow and Dehmlow in "Phase Transfer Catalysis" (1983), Verlag Chemie. The reaction can also be advantageously carried out in a biphasic system using 3⁄4 water and an organic solvent immiscible with it as solvents, in the presence of phase transfer catalysts, as described by Dehmlow and Dehmlow in "Phase Transfer Catalysis" (1983 ), Verlag Chemie.

I composti di formula generale (I) in cui W ed Y insieme rappresentano una catena -N(R6)0CCR7R80—, possono essere preparati a partire da un pirrolilamminofenolo di formula (VI) per reazione con un composto di formula (VII) a dare un pirrolilbenzossazinone di formula generale (le); questo può essere convertito ai composti di formula generale (Id) per condensazione con un composto di formula generale (Vili). Questa sequenza di reazioni è riportata nello schema 3. The compounds of general formula (I) in which W and Y together represent a chain -N (R6) 0CCR7R80—, can be prepared starting from a pyrrolylaminophenol of formula (VI) by reaction with a compound of formula (VII) to give a pyrrolylbenzoxazinone of general formula (l); this can be converted to compounds of general formula (Id) by condensation with a compound of general formula (VIII). This sequence of reactions is shown in diagram 3.

Schema 3 Scheme 3

Nelle formule generali riportate in questo schema di reazione : In the general formulas given in this reaction scheme:

- R, Ri, X, X1, X2, R7 ed R8 assumono i significati in precedenza definiti; - R, Ri, X, X1, X2, R7 and R8 take on the previously defined meanings;

- L2 rappresenta un atomo di alogeno, un gruppo OH, un gruppo alcossilico C1-C4; - L2 represents a halogen atom, an OH group, a C1-C4 alkoxy group;

- L3 ed L4 rappresentano un atomo di alogeno oppure un gruppo RL,SO2O- in cui RL rappresenta un gruppo alchilico od aloalchilico Ci-C4 od un gruppo fenilico eventualmente sostituito da gruppi alchilici C1-C4. - L3 and L4 represent a halogen atom or an RL, SO2O- group in which RL represents a C1-C4 alkyl or haloalkyl group or a phenyl group optionally substituted by C1-C4 alkyl groups.

- R6' assume i significati in precedenza definiti per il gruppo Re eccettuato il significato di atomo di idrogeno. - R6 'takes on the meanings previously defined for the group Re except for the meaning of hydrogen atom.

La reazione tra un composto di formula generale (VI) ed un composto di formula generale (VII) viene preferibilmente condotta in uno o più solventi organici inerti, in presenza di una base organica od inorganica in rapporto molare almeno doppio rispetto ai reagenti, ad una temperatura compresa tra i -10°C e la temperatura di ebollizione della miscela di reazione . The reaction between a compound of general formula (VI) and a compound of general formula (VII) is preferably carried out in one or more inert organic solvents, in the presence of an organic or inorganic base in a molar ratio at least double compared to the reactants, at a temperature between -10 ° C and the boiling temperature of the reaction mixture.

Basi e solventi possono essere scelti tra quelli indicati come preferiti per le reazioni riportate negli schemi 1 e 2. Bases and solvents can be selected from those indicated as preferred for the reactions reported in schemes 1 and 2.

La reazione può essere anche vantaggiosamente condotta in un sistema bifasico utilizzando come solventi l'acqua ed un solvente organico immiscibile con essa, in presenza di catalizzatori di trasferimento di fase, secondo quanto descritto in "Synthesis" , 1984, pag. 851-2. The reaction can also be advantageously carried out in a biphasic system using water and an organic solvent immiscible with it as solvents, in the presence of phase transfer catalysts, as described in "Synthesis", 1984, pag. 851-2.

La reazione tra un composto di formula (Ie) ed un composto di formula (VIII) viene effettuata secondo modalità operative analoghe a quelle descritte per la reazione riportata nello schema 2, in presenza di uno o più solventi organici inerti ed in presenza di una base, ad una temperatura compresa tra - 10°C e la temperatura di ebollizione della miscela di reazione. The reaction between a compound of formula (Ie) and a compound of formula (VIII) is carried out according to operating methods similar to those described for the reaction reported in scheme 2, in the presence of one or more inert organic solvents and in the presence of a base , at a temperature between - 10 ° C and the boiling temperature of the reaction mixture.

Basi e solventi possono essere scelti tra quelli indicati come preferiti per le reazioni riportate nello schema 2. Bases and solvents can be chosen from those indicated as preferred for the reactions reported in scheme 2.

Anche in questo caso la reazione può essere anche condotta in un sistema bifasico utilizzando come solventi l'acqua ed un solvente organico immiscibile con essa, in presenza di catalizzatori di trasferimento di fase. Also in this case the reaction can also be carried out in a biphasic system using water and an organic solvent immiscible with it as solvents, in the presence of phase transfer catalysts.

Gli intermedi di formule generali (II), (IV) e (VI), quando non siano descritti nella domanda di brevetto europea EP 1061072, possono essere ottenuti secondo i metodi sintetici in essa riportati. Gli intermedi di formule generali (III), (V), (VII) e (Vili) sono per lo più noti o facilmente ottenibili secondo metodi conosciuti nella prassi della chimica organica. The intermediates of general formulas (II), (IV) and (VI), when they are not described in the European patent application EP 1061072, can be obtained according to the synthetic methods reported therein. The intermediates of general formulas (III), (V), (VII) and (VIII) are mostly known or easily obtainable according to methods known in the practice of organic chemistry.

Come detto, i composti di formula generale (I) sono dotati di una elevata attività erbicida che li rende adatti all'impiego in campo agrario nella difesa delle colture utili dalle piante infestanti. In particolare, i composti oggetto della presente invenzione sono efficaci nel controllo, sia in preemergenza che in post-emergenza, di numerose erbe infestanti monocotiledoni e dicotiledoni. Nel contempo, detti composti mostrano compatibilità od assenza di effetti tossici nei confronti di colture utili in trattamenti di pre- e/o di post-emergenza. As mentioned, the compounds of general formula (I) are endowed with a high herbicidal activity which makes them suitable for use in the agricultural field in the defense of crops useful from weeds. In particular, the compounds object of the present invention are effective in the control, both in pre-emergence and in post-emergence, of numerous monocotyledonous and dicotyledonous weeds. At the same time, said compounds show compatibility or absence of toxic effects towards crops useful in pre- and / or post-emergence treatments.

Esempi di malerbe che possono essere efficacemente controllate utilizzando i composti aventi formula generale (I) sono: Abutilon theofrasti, Alisma plantago, Amaranthus spp., Amni maius , Capsella bursa pastoris, Chenopodium album, Convolvulus sepium, Galium aparine, Geranium dissectum, Ipomea spp., Matricaria spp., Papaver rhoaes, Phaseolus aureus , Polygonum persicaria, Portulaca oleracea, Sida spinosa, Sinapsis arvensis, Solanum nigrum, Stellaria media, Veronica spp., Viola spp., Xanthium spp., Alopecurus myosuroides, Avena fatua, Cyperus spp., Digitarla sanguinalis, Echinocloa spp., Heleocaris avicularis, Heteranthera spp., Panicum spp., Poa spp., Scirpus spp., Sorghum Spp · , ecc· Examples of weeds that can be effectively controlled using compounds having general formula (I) are: Abutilon theofrasti, Alisma plantago, Amaranthus spp., Amni maius, Capsella bursa pastoris, Chenopodium album, Convolvulus sepium, Galium aparine, Geranium dissectum, Ipomea spp. ., Matricaria spp., Papaver rhoaes, Phaseolus aureus, Polygonum persicaria, Portulaca oleracea, Sida spinosa, Sinapsis arvensis, Solanum nigrum, Stellaria media, Veronica spp., Viola spp., Xanthium spp., Alopecurus myosuroides, Avena sppua, Cyperppua ., Digitarla sanguinalis, Echinocloa spp., Heleocaris avicularis, Heteranthera spp., Panicum spp., Poa spp., Scirpus spp., Sorghum Spp., Etc.

Alle dosi di impiego utili per le applicazioni agrarie, i suddetti composti non hanno mostrato effetti tossici verso uno o più colture agrarie importanti quali riso (Oryza sativa), frumento (Triticum sp.), orzo (Hordeum vulgare), mais (Zea mays), soia (Glycine max). At the doses of use useful for agricultural applications, the above compounds did not show toxic effects towards one or more important agricultural crops such as rice (Oryza sativa), wheat (Triticum sp.), Barley (Hordeum vulgare), corn (Zea mays) , soy (Glycine max).

Ulteriore oggetto della presente invenzione è un metodo per il controllo delle erbe infestanti in aree coltivate mediante l'applicazione dei composti aventi formula generale (I). A further object of the present invention is a method for controlling weeds in cultivated areas by applying the compounds having general formula (I).

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, la malerba da colpire, il grado di infestazione, le condizioni climatiche, le caratteristiche del suolo, il metodo di applicazione, ecc. The amount of compound to be applied to obtain the desired effect may vary depending on various factors such as, for example, the compound used, the crop to be preserved, the weed to be affected, the degree of infestation, the climatic conditions, the characteristics of the soil, method of application, etc.

Dosi di composto comprese tra lg e lOOOg per ettaro forniscono, in genere, un sufficiente controllo. Compost doses ranging from lg to 1000g per hectare generally provide sufficient control.

Per gli impieghi in agricoltura è spesso vantaggioso utilizzare composizioni ad attività erbicida contenenti, come sostanza attiva, uno o più composti aventi formula generale (I), eventualmente anche come miscela di isomeri. For uses in agriculture it is often advantageous to use compositions with herbicidal activity containing, as an active substance, one or more compounds having general formula (I), possibly also as a mixture of isomers.

Si possono impiegare composizioni che si presentano sotto forma di polveri secche, polveri bagnabili, concentrati emulsionabili, microemulsioni, paste, granulati, soluzioni, sospensioni, ecc.: la scelta del tipo di composizione dipenderà dall'impiego specifico. It is possible to use compositions in the form of dry powders, wettable powders, emulsifiable concentrates, microemulsions, pastes, granulates, solutions, suspensions, etc .: the choice of the type of composition will depend on the specific use.

Le composizioni vengono preparate secondo metodologie note, per esempio diluendo o sciogliendo la sostan3⁄4 attiva con un mezzo solvente e/o diluente solido, eventualmente in presenza di tensioattivi. The compositions are prepared according to known methods, for example by diluting or dissolving the active substance with a solvent medium and / or solid diluent, optionally in the presence of surfactants.

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 . Kaolin, alumina, silica, talc, bentonite, gypsum, quartz, dolomite, attapulgite, montmorillonite, diatomaceous earth, cellulose, starch, etc. can be used as solid inert diluents or supports.

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 olii vegetali o minerali o loro miscele, ecc. Water or organic solvents such as aromatic hydrocarbons (xylols, mixtures of alkylbenzols, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), halogenated aromatic hydrocarbons (chlorobenzol, etc.), alcohols (methanol) can be used as liquid inert diluents , propanol, butanol, octanol, etc.), esters (isobutyl acetate, etc.), ketones (acetone, cyclohexanone, acetophenone, isophorone, ethylamyl ketone, etc.), or vegetable or mineral oils or their mixtures, etc.

Come tensioattivi possono essere utilizzati agenti bagnanti ed emulsificanti di tipo non-ionico (alchilfenoli polietossilati, alcoli grassi polietossilati ,ecc.),anionico (alchilbenzensolfonati, alchilsolfonati, ecc.), cationico (sali quaternari di alchilammonio, ecc.). Non-ionic wetting and emulsifying agents can be used as surfactants (polyethoxylated alkylphenols, polyethoxylated fatty alcohols, etc.), anionic (alkylbenzenesulphonates, alkylsulfonates, etc.), cationic (quaternary alkylammonium salts, etc.).

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.) . Furthermore, dispersants (for example lignin and its salts, cellulose derivatives, alginates, etc.), stabilizers (for example antioxidants, absorbers of ultraviolet rays, etc.) can also be added.

Per ampliare lo spettro d'azione delle suddette composizioni è possibile aggiungere ad esse altri ingradienti attivi quali, ad esempio, altri erbicidi, fungicidi, insetticidi, acaricidi, fertilizzanti, ecc.. To broaden the spectrum of action of the above compositions it is possible to add to them other active ingredients such as, for example, other herbicides, fungicides, insecticides, acaricides, fertilizers, etc.

Esempi di altri erbicidi che possono essere aggiunti alle composizioni contenenti uno o più composti di formula generale (I) sono i seguenti: acetochlor, acifluorfen, aclonifen, AKH-7088, alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, amitroie, anilofos, asulam, atrazine, azafenidin, azimsulfuron, aziprotryne, BAY MKH 6561, 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, carfentrazoneethyl, 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, cyhalofopbutyl, 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, dini tramine, dinoseb, dinoseb acetate, dinoterb, diphenamid, dipropetryn, diquat, dithiopyr, 1-diuron, eglinazine, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuronmethyl, 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), flucarbazonesodium, fluchloralin, flufenacet, flumetsulam, flumiclorac-pentyl, flumioxazin, flumipropin, fluometuron, fluoroglycofen, fluoronitrofen, flupoxam, flupropanate, flupyrsulfuron, flurenol, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine, furyloxyfen, glufosinate, glyphosate, halosulfuron-methyl, 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, MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, methazole, methoprotryne, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, molinate, monalide, monolinuron, naproanilide, napropamide, naptalam, NC-330, neburon, nicosulfuron, nipyraclofen, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pebulate, pendimethalin, 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, pyrazolynate , pyrazosulfuron, pyrazoxyfen, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, 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-aliate, triasulfuron, triaziflam, tribenuron, triclopyr, trietazine, trifloxysulfurori, trifluralin, triflusulfuron-methyl, tritosulfuron, UBI-C4874, vernolate . Examples of other herbicides that can be added to compositions containing one or more compounds of general formula (I) are the following: acetochlor, acifluorfen, aclonifen, AKH-7088, alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, amitroie, anilofos, asulam , atrazine, azafenidin, azimsulfuron, aziprotryne, BAY MKH 6561, beflubutamid, benazolin, benfluralin, benfuresate, bensulfuron, bensulide, bentazone, benzfendizone, benzobicyclon, benzofenap, benzthiazuron, brofenomacin, brofenoxyl, brofenoxylacomac, brofenoxylacomac, brofenoxylacomac, brofenoxyl , butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazoneethyl, chlomethoxyfen, chloramben, chlorbromuron, chlorbufam, chlorflurenol, chloridazon, chlorimuron, chlortlorthon, chlortl ethyl, cinmethylin, cinosulfuron, clethodim, clodinafop, clomazone, clomeprop, clopyralid, cloransulam-m ethyl, cumyluron (JC-940), cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofopbutyl, 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, dini tramine, dinoseb, dinoseb acetate, dinoterb, diphenamid, dipropetryn, diquat-diurnal-tTC , esprocarb, ethalfluralin, ethametsulfuronmethyl, ethidimuron, ethiozin (SMY 1500), ethofumesate, ethoxyfen-ethyl (HC-252), ethoxysulfuron, etobenzanid (HW 52), fenoxaprop, fenoxaprop-P, fentrazamide, flamprop, fenuron flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazolate (JV 485), flucarbazonesodium, fluchloralin, flufenacet, flumetsulam, flumiclorac-pentyl, flumioxazin, flumipropin, fluometuron, fluoroglycofen, flyroxupurate, fluoruponit ne, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine, furyloxyfen, glufosinate, glyphosate, halosulfuron-methyl, haloxyfop, haloxyfop-P-methyl, hexazinone, imazamapquinaza, imhabamazetaza, imhabapenz imazosulfuron, indanofan, iodosulfuron, ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, KPP-421, lactofen, lenacil, linuron, LS830556, MCPA, mfenacrop, mcpecrop, mcpecrop-mcpecrop-mcpa mesotrione, metamitron, metazachlor, methabenzthiazuron, methazole, methoprotryne, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, molinate, monaptalide, naptan, monolinuron, nc nicosulfuron, nipyraclofen, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pebulate, pendimethalin, pentanochlor, pentoxazone, pethox amid, phenmedipham, picloram, picolinafen, piperophos, pretilachlor, primisulfuron, prodiamine, profluazol, proglinazine, prometon, prometryne, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propyzamide, prosulfocarbate, pyryufol pyrazosulfuron, pyrazoxyfen, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, quinclorac, quinmerac, quizalofop, quizalofop-P, rimsulfuron, simmon-trone, sulfentretry, sulfentretry, sulfentrine, sulfentretry, sulfentretry, sulfentretry, sulfentr sulfosulfuron, 2,3,6-TBA, TCA-sodium, tebutam, tebuthiuron, tepraloxydim, terbacil, terbumeton, terbuthyl-azine, terbutryn, thenylchlor, thiazafluron, thiazopyr, thidiazimin, thifensulfoxyduron-methyl, thaziliobarb tri-aliate, triasulfuron, triaziflam, tribenuron, triclopyr, trietazine, trifloxysulfurori, trifluralin, triflusulfuron-methyl, tritosulfuron, UBI-C4874, vernolate.

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 1 e 90%. The concentration of active substance in the aforesaid compositions can vary within a wide range, depending on the active compound, the applications for which they are intended, the environmental conditions and the type of formulation adopted. In general, the concentration of active substance is preferably between 1 and 90%.

Vengono ora fom iti alcuni esempi che sono da intendersi come descrittivi e non limitativi della presente invenzione. Some examples are now given which are intended as descriptive and not limitative of the present invention.

ESEMPIO 1 EXAMPLE 1

Sintesi del [2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometilpirrol-3-il) -4-fluorofenossi]acetil cloruro (Intermedio di formula II). Synthesis of [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethylpyrrol-3-yl) -4-fluorophenoxy] acetyl chloride (Intermediate of formula II).

Cloruro di tionile (10 g) viene aggiunto ad una soluzione di acido [2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometilpirrol-3-il)-4-fluorofenossi]acetico (10 g) ed Ν,Ν-dimetilformammide (DMF; 0,1 mi) in cloruro di metilene (100 mi). Thionyl chloride (10 g) is added to a solution of [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethylpyrrol-3-yl) -4-fluorophenoxy] acetic acid (10 g) and Ν, Ν-dimethylformamide (DMF; 0.1ml) in methylene chloride (100ml).

Si scalda a riflusso sotto agitazione ed in atmosfera di azoto per 4 ore. The mixture is refluxed under stirring and in a nitrogen atmosphere for 4 hours.

Si concentra al rotavapor ed il residuo ottenuto (10 g) viene utilizzato tal quale per le prove successive . It is concentrated in the rotavapor and the residue obtained (10 g) is used as such for the subsequent tests.

L'acido di partenza (p.f. 142°C) è stato ottenuto per idrolisi del corrispondente estere etilico (composto N° 15 della domanda di brevetto europea EP 1061072. ESEMPIO 2 The starting acid (m.p.142 ° C) was obtained by hydrolysis of the corresponding ethyl ester (compound No. 15 of European patent application EP 1061072. EXAMPLE 2

Sintesi del 2-propinil [2-cloro-5-(2,4-dicloro-lmetil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi]acetato (Composto N. 1). Synthesis of 2-propinyl [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 1).

In una miscela di alcol propargilico (80 mg; 1,4 mmoli) e trietilammina (0,23 mi; 1,65 mmoli) in cloruro di metilene (15 mi) viene gocciolata a 0°C una soluzione in cloruro di metilene (5 mi) di [2-cloro-5- (2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi]acetil cloruro (0,6 g; 1,36 mmoli) ottenuto come descritto nell'esempio 1. A solution in methylene chloride (5 ml) of [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetyl chloride (0.6 g; 1.36 mmol) obtained as described in example 1.

Si lascia in agitazione per 2 ore a temperatura ambiente. Si aggiunge acqua (100 mi), si estrae con cloruro di metilene (2x80 mi), si anidrifica la fase organica con sodio solfato, si concentra. Il residuo è purificato per cromatografia su colonna di gel di silice eluendo con esano/acetato di etile 7:3. Si ottengono 0,5 g di un solido con p.f. 90-92°C; 3⁄4- e 19F-NMR in accordo con la struttura. It is left under stirring for 2 hours at room temperature. Water is added (100 ml), extracted with methylene chloride (2x80 ml), the organic phase is dried with sodium sulphate and concentrated. The residue is purified by silica gel column chromatography eluting with hexane / ethyl acetate 7: 3. 0.5 g of a solid are obtained with m.p. 90-92 ° C; 3⁄4- and 19F-NMR according to the structure.

ESEMPIO 3 EXAMPLE 3

Sintesi del 2-propenil [2-cloro-5-(2,4-dicloro-lmetil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetato (Composto N. 2). Synthesis of 2-propenyl [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 2).

Ad una miscela di 3 -(4-cloro-2-fluoro-5-idrossifenil) -2,4-dicloro-l-metil-5-trifluorometilpirrolo (0,45 g; 1,25 mmoli) e.carbonato di potassio (0,17 g; 1,26 mmoli) in DMF (10 mi) si aggiunge cloroacetato di allile (0,17 g; 1,26 mmoli); si scalda sotto agitazione a 50°C per 4 ore. Al termine della reazione la miscela viene versata in acqua (30 mi) ed estratta con etere etilico (3x30 mi); la fase eterea viene lavata con soluzione satura di cloruro di sodio, anidrificata con sodio solfato, concentrata al rotavapor. Il residuo è purificato per cromatografia su gel di silice eluendo con esano/acetato di etile 7:3. Si ottengono 0,42 g di olio denso: analisi elementare, H- e 19F-NMR in accordo con la struttura. To a mixture of 3 - (4-chloro-2-fluoro-5-hydroxyphenyl) -2,4-dichloro-1-methyl-5-trifluoromethylpyrrole (0.45 g; 1.25 mmol) and potassium carbonate ( 0.17 g; 1.26 mmoles) in DMF (10 ml) allyl chloroacetate (0.17 g; 1.26 mmoles) is added; it is heated under stirring at 50 ° C for 4 hours. At the end of the reaction the mixture is poured into water (30 ml) and extracted with ethyl ether (3x30 ml); the ether phase is washed with saturated sodium chloride solution, anhydrified with sodium sulphate, concentrated in the rotavapor. The residue is purified by silica gel chromatography eluting with hexane / ethyl acetate 7: 3. 0.42 g of thick oil are obtained: elemental analysis, H- and 19F-NMR according to the structure.

Il fenolo di partenza corrisponde al composto N° 13 della domanda di brevetto europea EP 1061072. The starting phenol corresponds to compound No. 13 of European patent application EP 1061072.

ESEMPIO 4 EXAMPLE 4

Sintesi dell' 1-(etossicarbonil)etil 2-cloro-5-(2,4-dicloro-l-metil-5-trifluoro-metilpirrol-3-il) -4-fluorobenzoato (Composto N. 3). Synthesis of 1- (ethoxycarbonyl) ethyl 2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoro-methylpyrrol-3-yl) -4-fluorobenzoate (Compound No. 3).

Una soluzione di 2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometilpirrol-3-il) -4-fluorobenzoil cloruro (0,6 g; 1,46 mmoli) in cloruro di metilene (5 mi) viene gocciolata a 0°C in una miscela di etil lattato (0,18 g; 1,5 mmoli), trietilammina (0,23 mi; 1,65 mmoli) e cloruro di metilene (15 mi). Si scalda a riflusso per 4 ore. Si aggiunge acqua (100 mi), si estrae con cloruro di metilene (2x80 mi) , si anidrifica la fase organica con sodio solfato, si concentra. Il residuo è purificato per cromatografia su colonna di gel di silice eluendo con esano/acetato di etile 7:3. Si ottengono 0,38 g di un olio denso: analisi elementare, e 19F-NMR in accordo con la struttura. A solution of 2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethylpyrrol-3-yl) -4-fluorobenzoyl chloride (0.6 g; 1.46 mmol) in methylene chloride (5 ml) is dropped at 0 ° C in a mixture of ethyl lactate (0.18 g; 1.5 mmol), triethylamine (0.23 ml; 1.65 mmol) and methylene chloride (15 ml). The mixture is refluxed for 4 hours. Water is added (100 ml), extracted with methylene chloride (2x80 ml), the organic phase is dried with sodium sulphate and concentrated. The residue is purified by silica gel column chromatography eluting with hexane / ethyl acetate 7: 3. 0.38 g of a thick oil are obtained: elemental analysis, and 19F-NMR according to the structure.

ESEMPIO 5 EXAMPLE 5

Seguendo le procedure descritte negli esempi sopra riportati, sono stati preparati i seguenti composti (identificati mediante analisi elementare, H- e 19F-NMR) : Following the procedures described in the examples above, the following compounds were prepared (identified by elemental analysis, H- and 19F-NMR):

3,3-dicloro-2-propenil [2-cloro-5- (2,4-dicloro-lmetil-5-trif luorometil-pirrol-3-il) -4-fluorofenossi] acetato (Composto N° 4); 3,3-dichloro-2-propenyl [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 4);

- 2-metil-2-propenil [2-cloro-5- (2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetato (Composto N° 5); - 2-methyl-2-propenyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 5);

3-butin-2-il [2-cloro-5- (2,4-dicloro-l-metil-5-trif luorometil-pirrol-3-il) -4-fluorofenossi] acetato (Composto N° 6); 3-butin-2-yl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 6);

2-metil-3-butin-2-il [2 -cloro-5-(2,4-dicloro- 1-metil-5-trifluorometil-pirrol- 3-il) -4-fluorofenossi] acetato (Composto N° 7); 2-methyl-3-butin-2-yl [2 -chloro-5- (2,4-dichloro- 1-methyl-5-trifluoromethyl-pyrrol- 3-yl) -4-fluorophenoxy] acetate (Compound No. 7 );

4-metossibut-2-inil [2 -cloro-5-(2,4-dicloro-lmetil-5-trif luorometil-pirrol-3-il) -4-fluorofenossi] acetato (Composto N° 8); 4-methoxybut-2-yl [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 8);

- ciclopropilmetil [2-cloro -5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetato (Composto N° 9); - cyclopropylmethyl [2-chloro -5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 9);

- ciclobutilmetil [2-cloro-5 -(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4 -fluorofenossi]acetato (Composto N° 10); - cyclobutylmethyl [2-chloro-5 - (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4 -fluorophenoxy] acetate (Compound No. 10);

ciclopentil [2-cloro-5- (2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetato (Composto N° 11); cyclopentyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 11);

3-ossetanil [2-cloro-5- (2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetato (Composto N° 12); 3-oxetanil [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 12);

- 2,3-epossipropil [2-cloro-5- (2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetato (Composto N° 13); - 2,3-epoxypropyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 13);

2-etiltioetil [2-cloro-5- (2,4-dicloro-l-metil-5-trif luorometil-pirrol-3-il) -4-fluorofenossi] acetato (Composto N° 14); 2-ethylthioethyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 14);

- 2-(4-morfolil) etil [2-cloro-5- (2,4-dicloro-l-metil-5-trif luorometil-pirrol-3-il) -4-f luorofenossi] acetato (Composto N° 15); - 2- (4-morpholyl) ethyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 15 );

2-(1-pirrolidil) etil [2-cloro-5- (2,4-dicloro-lmetil -5-trif luorometil -pirrol-3 -il)-4-fluorofenossi] acetato (Composto N° 16); 2- (1-pyrrolidyl) ethyl [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3 -yl) -4-fluorophenoxy] acetate (Compound No. 16);

- 2-(2-pirrolidinonil) etil [2-cloro-5-(2,4-dicloro-lmetil-5-trif luorometil-pirrol-3-il) -4-fluorofenossi] acetato (Composto N° 17); - 2- (2-pyrrolidinonyl) ethyl [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 17);

- 2-acetilamminoetil [2-cloro-5- (2,4-dicloro- 1-met il-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetato (Composto N° 18); - 2-acetylaminoethyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 18);

- 2-acetilossietil [2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi]acetato (Composto N° 19); - 2-acetyloxyethyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 19);

2-propenil [2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il) -4-fluoro- fenossi]acetato (Composto N° 20); 2-propenyl [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-phenoxy] acetate (Compound No. 20);

2-propinil [2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il) -4-fluoro-fenossi]acetato (Composto N° 21); 2-propinyl [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-phenoxy] acetate (Compound No. 21);

3-butin-2-il [2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il) -4-fluoro-fenossi]acetato (Composto N° 22); 3-butin-2-yl [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-phenoxy] acetate (Compound No. 22);

2-metil-3-butin-2-il [2-cloro-5-(2,4-dicloro-letil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetato (Composto N° 23); 2-methyl-3-butin-2-yl [2-chloro-5- (2,4-dichloro-letyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 23);

4-metossibut-2-inil[2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi]acetato (Composto 24); 4-methoxybut-2-yl [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound 24);

ciclopropilmetil[2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi]acetato (Composto N° 25); cyclopropylmethyl [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 25);

-2-metossietil [2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi]acetato (Composto N° 26); -2-methoxyethyl [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 26);

3-ossetanil [2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il)-4-fluoro-fenossi]acetato (Composto N° 27); 3-oxetanil [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-phenoxy] acetate (Compound No. 27);

- 2,3-epossipropil [2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi]acetato (Composto N° 28); - 2,3-epoxypropyl [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetate (Compound No. 28);

- 2-propenil 2-cloro-5- (2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluoro-benzoato (Composto N° 29); - 2-propenyl 2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-benzoate (Compound No. 29);

- 2-propinil-2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluoro-benzoato (Composto N° 30); - 2-propinyl-2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-benzoate (Compound No. 30);

3-butin-2-il 2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluorobenzoato (Composto N° 31); 3-butin-2-yl 2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorobenzoate (Compound No. 31);

- 2-metil-3-butin-2-il 2-cloro-5-(2,4-dicloro-lmetil-5-1rifluorometil-pirrol-3-il)-4-fluorobenzoato (Composto N° 32); - 2-methyl-3-butin-2-yl 2-chloro-5- (2,4-dichloro-lmethyl-5-1rifluoromethyl-pyrrol-3-yl) -4-fluorobenzoate (Compound No. 32);

- 4-metossibut-2-inil 2-cloro-5-(2,4-dicloro-lmetil-5-trifluorometil-pirrol-3-il)-4-fluorobenzoato (Composto N° 33); - 4-methoxybut-2-yl 2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorobenzoate (Compound No. 33);

- ciclopropilmetil 2-cloro-5- (2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluorobenzoato (Composto N° 34); - cyclopropylmethyl 2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorobenzoate (Compound No. 34);

2-metossietil 2-cloro-5- (2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluorobenzoato (Composto N° 35); 2-methoxyethyl 2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorobenzoate (Compound No. 35);

- 2-(2-propenilossicarbonil)prop-2-il 2-cloro-5-(2,4-dicloro-l-metil-5-trifluoro-metil-pirrol-3-il)-4-fluorobenzoato (Composto N° 36); - 2- (2-propenyloxycarbonyl) prop-2-yl 2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoro-methyl-pyrrol-3-yl) -4-fluorobenzoate (Compound No. 36);

- 2-(2-propenilossicarbonil)prop-2-il 2-cloro-5-(2,4-dicloro-l-metil-5-trifluoro-metil-pirrol-3-il)benzoato (Composto N° 37); - 2- (2-propenyloxycarbonyl) prop-2-yl 2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoro-methyl-pyrrol-3-yl) benzoate (Compound No. 37);

- 2-(2-propenilossicarbonil)prop-2-il 2-cloro-5-(2,4-dicloro-l-etil-5-trifluoro-metil-pirrol-3-il)benzoato (Composto N° 38); - 2- (2-propenyloxycarbonyl) prop-2-yl 2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoro-methyl-pyrrol-3-yl) benzoate (Compound No. 38);

- N-metil-N-metossi-[2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi] acetammid (Composto N° 39); - N-methyl-N-methoxy- [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide (Compound No. 39);

- N-(2-propinil)-[2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi] acetammide (Composto N° 40); - N- (2-propinyl) - [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide (Compound No. 40);

N-metil-N- (2-propinil)-[2-cloro-5-(2,4-diclorol-metil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi]acetairanide (Composto N° 41); N-methyl-N- (2-propinyl) - [2-chloro-5- (2,4-dichlorol-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetairanide (Compound No. 41) ;

N- (2-propenil)-[2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetammide (Composto N° 42); N- (2-propenyl) - [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide (Compound No. 42);

N-ciclopropilmetil- [2-cloro-5-(2,4-dicloro-lmetil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi]acetammide (Composto N° 43); N-cyclopropylmethyl- [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide (Compound No. 43);

N- (2-metossietil)-[2-cloro-5-(2,4-dicloro-lmetil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi]acetammide (Composto N° 44); N- (2-methoxyethyl) - [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide (Compound No. 44);

N-metil-N- (2-metossietil)-[2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi]acetammide (Composto N° 45); N-methyl-N- (2-methoxyethyl) - [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide (Compound No. 45);

N- (etossicarbonilmetil)-[2-cloro-5-(2,4-diclorol-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetammide (Composto N° 46); N- (ethoxycarbonylmethyl) - [2-chloro-5- (2,4-dichlorol-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide (Compound No. 46);

4- [2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossiacetil]morfolina (Composto N° 47); 4- [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxyacetyl] morpholine (Compound No. 47);

1- [2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluorofenossiacetil]pirrolidina (Composto N° 48); N-metossi- [2-cloro-5- (2,4-dicloro-l-etil-5-trif luorometil-pirrol-3-il) -4-fluorofenossi] acetammide (Composto N° 49); 1- [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxyacetyl] pyrrolidine (Compound No. 48); N-methoxy- [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide (Compound No. 49);

N-metil-N-metossi- [2-cloro-5- (2,4-dicloro-letil-5-trif luorometil-pirrol-3-il) -4-fluorofenossi] acetaitimide (Composto N° 50); N-methyl-N-methoxy- [2-chloro-5- (2,4-dichloro-letyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetaithimide (Compound No. 50);

N- (2-propinil) -[2-cloro- 5-(2,4-dicloro-l-etil-5-trif luorometil-pirrol-3-il) -4-fluorofenossi] acetammide (Composto N° 51); N- (2-propinyl) - [2-chloro- 5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide (Compound No. 51);

N-metil-N- (2-propinil) -[2-cloro-5- (2,4-diclorol-etil-5-trif luorometil-pirrol-3-il) -4-fluorofenossi] acetammide (Composto N° 52); N-methyl-N- (2-propinyl) - [2-chloro-5- (2,4-dichlorol-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide (Compound No. 52 );

N- (2-propenil) -[2-cloro-5- (2,4-dicloro-l-etil-5-trif luorometil-pirrol-3-il) -4-fluorofenossi] acetammide (Composto N° 53); N- (2-propenyl) - [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide (Compound No. 53);

N-ciclopropilmetil- [2-cloro-5- (2,4-dicloro-letil-5-trifluorometil-pirrol-3-il) -4-fluorofenossi] acetammide (Composto N° 54); N- (2-metossietil) - [2-cloro-5- (2,4-dicloro-letil-5-trif luorometil-pirrol-3-il) -4-fluorofenossi] acetammide (Composto N° 55); N-cyclopropylmethyl- [2-chloro-5- (2,4-dichloro-letyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide (Compound No. 54); N- (2-methoxyethyl) - [2-chloro-5- (2,4-dichloro-letyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide (Compound No. 55);

N-metil-N- (2-metossietil) -[2-cloro-5- (2,4-dicloro-l-etil-5-trif luorometil-pirrol-3-il) -4-f luorofenossi] acetammide (Composto N° 56); N- (etossicarbonilmetil)-[2-cloro-5-(2,4-diclorol-etil-5-trifluorometil-pirrol-3-il)-4-fluorofenossi]acetanunide (Composto N° 57); N-methyl-N- (2-methoxyethyl) - [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetamide (Compound N ° 56); N- (ethoxycarbonylmethyl) - [2-chloro-5- (2,4-dichlorol-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxy] acetanunide (Compound No. 57);

1- [2-cloro-5-(2,4-dicloro-l-etil-5-trifluorometil-pirrol-3-il)-4-fluorofenossiacetil]pirrolidina (Composto N° 58); 1- [2-chloro-5- (2,4-dichloro-1-ethyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenoxyacetyl] pyrrolidine (Compound No. 58);

N-metossi- [2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluoro]benzammide (Composto N° 59); N-methoxy- [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro] benzamide (Compound No. 59);

N-metil-N-metossi- [2-cloro-5-(2,4-dicloro-lmetil-5-trifluorometil-pirrol-3-il) -4-fluoro]benzammide (Composto N° 60); N-methyl-N-methoxy- [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro] benzamide (Compound No. 60);

N- (2-propinil)-[2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-fluoro] benzammide (Composto N° 61); N- (2-propinyl) - [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro] benzamide (Compound No. 61);

N-metil-N- (2-propinil)-[2-cloro-5-(2,4-diclorol-metil-5-trifluorometil-pirrol-3-il) -4-fluoro] benzammide (Composto N° 62); N-methyl-N- (2-propinyl) - [2-chloro-5- (2,4-dichlorol-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro] benzamide (Compound No. 62) ;

N- (2-propenil)-[2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il) -4-luoro]benzcunmide (Composto N° 63); N- (2-propenyl) - [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-luoro] benzcunmide (Compound No. 63);

N-ciclopropilmetil- [2-cloro-5-(2,4-dicloro-lmet il-5-trifluorometil-pirrol-3-il)-4-fluoro]benzammide (Composto N° 64); N-cyclopropylmethyl- [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro] benzamide (Compound No. 64);

N-(2-metossietil)-[2-cloro-5-(2,4-dicloro-lmetil-5-trifluorometil-pirrol-3-il)-4-fluoro] benzammide (Composto N° 65); N- (2-methoxyethyl) - [2-chloro-5- (2,4-dichloro-1methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro] benzamide (Compound No. 65);

N-metil-N-(2-metossietil)- [2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluoro]benzammide (Composto N° 66); N-methyl-N- (2-methoxyethyl) - [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro] benzamide (Compound No. 66);

a-[2-cloro-5-(2,4-dicloro-l-metil-5-trifluoro metil-pirrol-3-il)-4-fluorofenossi]-γ-butirrolattone (Composto N° 67); a- [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoro methyl-pyrrol-3-yl) -4-fluorophenoxy] -γ-butyrolactone (Compound No. 67);

3-[2-cloro-5-(2,4-dicloro-l-metil-5-trifluoro metil-pirrol-3-il)-4-fluorofenossi]-l-metil-2-pirrolidinone (Composto N° 68); 3- [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoro methyl-pyrrol-3-yl) -4-fluorophenoxy] -1-methyl-2-pyrrolidinone (Compound No. 68) ;

2-propinil [2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluoro-feniltio] acetato (Composto N° 69); 2-propinyl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluoro-phenylthio] acetate (Compound No. 69);

3-butin-2-il [2-cloro-5-(2,4-dicloro-l-metil-5-trifluorometil-pirrol-3-il)-4-fluorofeniltio] acetato (Composto N° 70). 3-butin-2-yl [2-chloro-5- (2,4-dichloro-1-methyl-5-trifluoromethyl-pyrrol-3-yl) -4-fluorophenylthio] acetate (Compound No. 70).

ESEMPIO 6 EXAMPLE 6

Determinazione dell'attività erbicida e della fitotossicità in post-emergenza. Determination of herbicidal activity and phytotoxicity in post-emergence.

L'attività erbicida dei composti dell'invenzione in post-emergenza è stata valutata secondo le seguenti modalità operative. The herbicidal activity of the compounds of the invention in post-emergence was evaluated according to the following operative modalities.

Le speci vegetali di interesse (erbe infestanti o colture) sono state seminate in vasetti aventi diametro superiore di 10 cm, altezza di 10 cm e contenenti terreno sabbioso. Sono stati utilizzati 10 vasetti per ogni specie vegetale. The plant species of interest (weeds or crops) were sown in pots with a diameter greater than 10 cm, a height of 10 cm and containing sandy soil. 10 jars were used for each plant species.

Ad ogni vasetto è stata aggiunta acqua in quantità idonea alla germinazione dei semi. I vasetti sono stati quindi divisi in due gruppi ognuno contenente 5 vasetti per ciascuna infestante o coltura. Water was added to each jar in a quantity suitable for the germination of the seeds. The jars were then divided into two groups each containing 5 jars for each weed or crop.

Dopo quindici giorni dalla semina (dieci nel caso del frumento) , quando cioè le piantine infestanti e le colture, a seconda della specie, avevano un'altezza di 10-15 cm, il primo gruppo di vasetti è stato trattato con una dispersione idro-acetonica contenente acetone al 10% in volume, il prodotto in valutazione alla concentrazione desiderata e Tween 20 allo 0.5%. Fifteen days after sowing (ten in the case of wheat), i.e. when the weed seedlings and crops, depending on the species, had a height of 10-15 cm, the first group of pots was treated with a water dispersion. acetone containing acetone at 10% by volume, the product under evaluation at the desired concentration and Tween 20 at 0.5%.

Il secondo gruppo è stato trattato soltanto con una soluzione idroacetonica contenente acetone al 10% in volume e Tween 20 allo 0.5%, ed è stato impiegato come termine di confronto (testimone). The second group was treated only with a hydroacetonic solution containing acetone at 10% by volume and Tween 20 at 0.5%, and was used as a comparison term (control).

Tutti i vasetti sono stati mantenuti sotto osservazione in ambiente condizionato alle seguenti condizioni ambientali: All the jars were kept under observation in a conditioned environment under the following environmental conditions:

- temperatura: 24°C - temperature: 24 ° C

umidità relativa: 60% relative humidity: 60%

- fotoperiodo: 16 ore - photoperiod: 16 hours

- intensità luminosa: 10000 lux - light intensity: 10000 lux

Ogni due giorni i vasetti sono stati uniformemente innaffiati in modo da assicurare un grado di umidità sufficiente per un buon sviluppo delle piante. Every two days the pots were watered evenly in order to ensure a sufficient degree of humidity for a good development of the plants.

Dopo quindici giorni dal trattamento è stata valutata l'attività erbicida in base alla seguente scala di valori riferentesi alla percentuale di danno rilevato sulle piante trattate rispetto a quelle non trattate (testimone) : Fifteen days after treatment, the herbicidal activity was assessed on the basis of the following scale of values referring to the percentage of damage detected on the treated plants compared to the untreated ones (witness):

0 = 0 - 10 % di danno 0 = 0 - 10% damage

1 = 11 - 30 % di danno 1 = 11 - 30% damage

2 = 31 - 50 % di danno 2 = 31 - 50% damage

3 = 51 - 70 % di danno 3 = 51 - 70% damage

4 = 71 - 90 % di danno 4 = 71 - 90% damage

5 = 91 % di danno - morte della pianta 5 = 91% damage - plant death

In tabell'a 1 sono riportati i risultati ottenuti trattando 3⁄4on i composti 1 e 2 alla dose di 50 g/ha le speci vegetali sotto riportate: Table 1 shows the results obtained by treating 3⁄4 with compounds 1 and 2 at a dose of 50 g / ha of the plant species listed below:

Abutilon theofrasti (AT); Amaranthus retroflexus (AR); Chenopodium album (CA); Convolvulus sepium (CS); Galium aparine (GA); Ipomea purpurea (IP); Portulaca oleracea (PO); Solanum nigrum (SN); Sida spinosa (SS); mais (M). Abutilon theofrasti (AT); Amaranthus retroflexus (AR); Chenopodium album (CA); Convolvulus sepium (CS); Galium aparine (GA); Ipomea purpurea (IP); Portulaca oleracea (PO); Solanum nigrum (SN); Sida spinosa (SS); corn (M).

Tabella 1: Attività erbicida in post-emergenza alla dose di 50 g/ha Table 1: Herbicidal activity in post-emergence at a dose of 50 g / ha

Claims (8)

RIVENDICAZIONI 1. Fenilpirroli aventi formula generale (I): CLAIMS 1. Phenylpyrroles having general formula (I): ( I ) in cui: - R ed Ri, uguali o diversi tra loro, rappresentano un gruppo alchilico od aloalchilico C1-C4; - X ed Xi, uguali o diversi tra loro, rappresentano un atomo di alogeno; - X2 rappresenta un atomo di idrogeno od un atomo di alageno; - Y rappresenta un atomo di alogeno, un gruppo aloalchilico od aloalcossilico Ci.-C4, un gruppo ciano, un gruppo nitro; W rappresenta uno dei seguenti raggruppamenti: (I) in which: - R and Ri, the same or different from each other, represent a C1-C4 alkyl or haloalkyl group; - X and Xi, the same or different from each other, represent a halogen atom; - X2 represents a hydrogen atom or a halogen atom; - Y represents a halogen atom, a C1-C4 haloalkyl or haloalkoxyl group, a cyano group, a nitro group; W represents one of the following groupings: in cui: Ra ed Rb , uguali o diversi tra loro, rappresentano un atomo di idrogeno od un gruppo alchilico C1-C4; R2 rappresenta: un gruppo alchenilico C3-C6 eventualmente sostituito da gruppi alcossilici C1-C4; un gruppo alchinilico C3-C6 eventualmente sostituito da gruppi alcossilici C1-C4; un gruppo alcossialchilico od alchiltioalchilico C2-C8; un gruppo cicloalchilico C3-C8 o cicloalchilalchilico C4-C10 eventualmente sostituito da gruppi alchilici C1-C4 ed eventualmente interrotto da atomi di ossigeno; un gruppo alchilamminoalchilico C2-C8 od un gruppo dialchilamminoalchilico C4-C12; un gruppo 4-morfolilalchilico C5-C9; un gruppo 1-pirrolidilalchilico C5-C9; un gruppo 1-piperidilalchilico C6-C10; un gruppo 2-pirrolidinonilalchilico C5-C9; un gruppo alchilcarbonilammino-alchilico C3-C9; un gruppo alchilcarbonilossialchilico C4-C9; un gruppo alcossicarbonilalchilico C3-C10; un gruppo alchenil -ossicarbonilalchilico C4-C12; un gruppo alchinilossicarbonilalchilico C4-C12; un gruppo alcossialcossicarbonilalchilico C4-C12; un gruppo cicloalcossicarbonilalchilico C5-C10; un gruppo cicloalchilalcossicarbonilalchilico C6-C12; tutti questi gruppi a loro volta possono essere sostituiti da atomi di alogeno; oppure rappresenta un gruppo arilico, arilalchilico, arilossialchilico eteroarilico, eteroarilalchilico eteroarilossialchilico, arilamminoalchilico, eteroarilamminoalchilico, tutti gruppi eventualmente sostituiti da gruppi C1-C4 alchilici, aloalchilici, alcossilici, aloalcossilici, da atomi di alogeno, da gruppi nitro, da gruppi ciano; R3 rappresenta un gruppo alchenilico od alchinilico C3-C6 eventualmente sostituito da gruppi alcossilici C1-C4 ed eventualmente alogenato; un gruppo alcossialchilico od alchiltioalchilico C2-C8 eventualmente alogenato; un gruppo cicloalchilico C3-C8 o cicloalohilalchilico C4-C10 eventualmente sostituito da gruppi alchilici od aloalchilici C1-C4, eventualmente alogenato ed eventualmente interrotto da atomi di ossigeno; un gruppo alchilammino-alchilico C3-C8 od un gruppo dialchilamminoalchilico C4-C12 eventualmente alogenato; un gruppo alcossicarbonilalchilico C3-C8 eventualmente alogenato; un gruppo OH; un gruppo alcossilico od aloalcossilico C1-C6; un gruppo alchilcarbonilossi od aloalchilcarbonilossi C2-C7; oppure rappresenta un gruppo arilico, arilalchilico, arilossialchilico eteroarilico, eteroarilalchilico eteroarilossialchilico, arilamminoalchilico, eteroarilamminoalchilico, tutti gruppi eventualmente sostituiti da gruppi Ci-C4 alchilici, aloalchilici, alcossilici, aloalcossilici, da atomi di alogeno, da gruppi nitro, da gruppi ciano; - R4 rappresenta: un atomo di idrogeno; un gruppo alchilico od aloalchilico C1-C6; un gruppo alchenilico od aloalchenilico C3-C6 eventualmente sostituito da gruppi alcossilici od aloalcossilici C1-C4; un gruppo alchinilico od alo-alchinilico C3-C6 eventualmente sostituito da gruppi alcossilici od alo-alcossilici C1-C4; un gruppo alcossislchilico od aloalcossialchilico C2-C8; - Z rappresenta un atomo di ossigeno od un atomo di zolfo; - m rappresenta un numero intero compreso tra 1 e 4; - n rappresenta zero oppure 1; - p rappresenta 1 oppure 2; - K rappresenta un atomo di ossigeno oppure un gruppo NRK in cui: - Rk rappresenta un atomo di idrogeno, un gruppo OH, un gruppo alcossilico od aloalcossilico C1-C6, un gruppo alchilcarbonilossi C2-C6 eventualmente alogenato, un gruppo alchenilico od alchinilico C3-C6 eventualmente sostituito d a gruppi alcossilici od aloalcossilici C1-C4 ed eventualmente alogenato; un gruppo alcossialchilico C2-C8 eventualmente alogenato; un gruppo cicloalchilico C3-C8 o cicloalchilalchilico C4-C10 eventualmente sostituito da gruppi alchilici od aloalchilici C1-C4, eventualmente alogenato ed eventualmente interrotto da atomi di ossigeno; un gruppo alchilaminino-alchilico C3-C8 od un gruppo dialchilamminoalchilico C4-C12 eventualmente alogenato . in W2, quando n = 1: R3 ed R4 insieme possono anche rappresentare una catena alchilenica C2-C7 eventualmente sostituita da gruppi alchilici C1-C4 ed eventualmente interrotta da atomi di ossigeno o da un gruppo NR5 in cui: R5 rappresenta un atomo di idrogeno, un gruppo alchilico od aloalchilico C1-C6, un gruppo alchenilico od aloalchenilico C3-C6, un gruppo alchinilico od aloalchinilico C3-C6, un gruppo alcossialchilico od aloalcossialchilico C2-C8, un gruppo alchilcarbonilico od aloalchilcarbonilico C2-C7; alternativamente, il gruppo W ed il gruppo Y insieme possono rappresentare una catena -N (R6)0CCR7R80- in cui: - R6 rappresenta un atomo di idrogeno, un gruppo alchilico od aloalchilico C1-C6, un gruppo alchenilico od aloalchenilico C3-C6 eventualmente sostituito da gruppi alcossilici od aloalcossilici C1-C4, un gruppo alchinilico od alo-alchinilico C3-C6 eventualmente sostituito d a g ruppi alcossilici od aloalcossilici C1-C4, un gruppo alcossialchilico od aloalcossialchilico C2-C8; - R7 ed R8, uguali o diversi tra loro, rappresentano un atomo di idrogeno oppure un gruppo alchilico od aloalchilico C1-C4. in which: Ra and Rb, the same or different from each other, represent a hydrogen atom or a C1-C4 alkyl group; R2 represents: a C3-C6 alkenyl group optionally substituted by C1-C4 alkoxy groups; a C3-C6 alkynyl group optionally substituted by C1-C4 alkoxy groups; a C2-C8 alkoxyalkyl or alkylthioalkyl group; a C3-C8 cycloalkyl group or C4-C10 cycloalkylalkyl group optionally substituted by C1-C4 alkyl groups and optionally interrupted by oxygen atoms; a C2-C8 alkylaminoalkyl group or a C4-C12 dialkylaminoalkyl group; a C5-C9 4-morpholylalkyl group; a C5-C9 1-pyrrolidylalkyl group; a C6-C10 1-piperidylalkyl group; a C5-C9 2-pyrrolidinonylalkyl group; a C3-C9 alkylcarbonylamino-alkyl group; a C4-C9 alkylcarbonyloxyalkyl group; a C3-C10 alkoxycarbonylalkyl group; a C4-C12 alkenyl -oxycarbonylalkyl group; a C4-C12 alkynyloxycarbonylalkyl group; a C4-C12 alkoxyalkoxycarbonylalkyl group; a C5-C10 cycloalkoxycarbonylalkyl group; a C6-C12 cycloalkylalkoxycarbonylalkyl group; all these groups in turn can be replaced by halogen atoms; or it represents an aryl, arylalkyl, aryloxyalkyl heteroaryl, heteroarylalkyl heteroaryloxyalkyl, arylaminoalkyl, heteroarylaminoalkyl groups, all groups possibly substituted by C1-C4 alkyl groups, haloalkyl, alkoxy, haloalkyloxyl groups, by alkoxy nitrogen groups, by atoms of nitrogen groups; R3 represents a C3-C6 alkenyl or alkynyl group optionally substituted by C1-C4 alkoxy groups and optionally halogenated; a C2-C8 alkoxyalkyl or alkylthioalkyl group optionally halogenated; a C3-C8 cycloalkyl group or C4-C10 cycloalkylalkyl group optionally substituted by C1-C4 alkyl or haloalkyl groups, optionally halogenated and optionally interrupted by oxygen atoms; a C3-C8 alkylamino-alkyl group or a C4-C12 dialkylaminoalkyl group optionally halogenated; a C3-C8 alkoxycarbonylalkyl group optionally halogenated; an OH group; a C1-C6 alkoxy or haloalkoxyl group; a C2-C7 alkylcarbonyloxy or haloalkylcarbonyloxy group; or it represents an aryl, arylalkyl, aryloxyalkyl heteroaryl, heteroarylalkyl heteroaryloxyalkyl, arylaminoalkyl, heteroarylaminoalkyl groups, all groups optionally substituted by C4-C4 alkyl, haloalkyl, alkoxy, haloalkyl, nitrogen groups, by atoms from nitrogen groups; - R4 represents: a hydrogen atom; a C1-C6 alkyl or haloalkyl group; a C3-C6 alkenyl or haloalkenyl group optionally substituted by C1-C4 alkoxy or haloalkoxyl groups; a C3-C6 alkynyl or halo-alkynyl group optionally substituted by C1-C4 alkoxy or halo-alkoxy groups; a C2-C8 alkoxy or haloalkoxyalkyl group; - Z represents an oxygen atom or a sulfur atom; - m represents an integer between 1 and 4; - n represents zero or 1; - p represents 1 or 2; - K represents an oxygen atom or an NRK group in which: - Rk represents a hydrogen atom, an OH group, an alkoxy or haloalkoxy group C1-C6, an alkylcarbonyloxy group C2-C6 possibly halogenated, an alkenyl or alkynyl group C3-C6 possibly substituted by alkoxyl or haloalkoxyl groups C1-C4 and possibly halogenated; a C2-C8 alkoxyalkyl group optionally halogenated; a C3-C8 cycloalkyl group or C4-C10 cycloalkylalkyl group optionally substituted by C1-C4 alkyl or haloalkyl groups, optionally halogenated and optionally interrupted by oxygen atoms; a C3-C8 alkylamine-alkyl group or a C4-C12 dialkylaminoalkyl group optionally halogenated. in W2, when n = 1: R3 and R4 together can also represent a C2-C7 alkylene chain possibly replaced by C1-C4 alkyl groups and possibly interrupted by oxygen atoms or by a NR5 group in which: R5 represents a hydrogen atom, a C1-C6 alkyl or haloalkyl group, a C3-C6 alkenyl or haloalkenyl group, a C3-C6 alkynyl or haloalkynyl group, a C2-C8 alkoxyalkyl or haloalkoxyalkyl group, a C2-C8 alkylcarbonyl or haloalkyl group C7; alternatively, group W and group Y together can represent a chain -N (R6) 0CCR7R80- in which: - R6 represents a hydrogen atom, a C1-C6 alkyl or haloalkyl group, a C3-C6 alkenyl or haloalkenyl group optionally substituted by C1-C4 alkoxyl or haloalkoxyl groups, a C3-C6 alkynyl or halo-alkynyl group optionally substituted by groups C1-C4 alkoxy or haloalkoxy, a C2-C8 alkoxyalkyl or haloalkoxyalkyl group; - R7 and R8, the same or different from each other, represent a hydrogen atom or a C1-C4 alkyl or haloalkyl group. 2. Processo per la preparazione dei composti di formula generale (I) in cui- W rappresenta W3 oppure W2 comprendente la condensazione di un fenilpirrolo di formula generale (II) con un alcool od un'ammina di formula generale (III), a dare un estere od un ammide di formula generale (la) secondo lo schema di reazione 1: Schema 1 2. Process for the preparation of compounds of general formula (I) in which - W represents W3 or W2 comprising the condensation of a phenylpyrrole of general formula (II) with an alcohol or an amine of general formula (III), to give an ester or an amide of general formula (la) according to the reaction scheme 1: Scheme 1 (Π) (la) in cui: R, Ri, X, Xi, X2 ed Y hanno i significati in precedenza definiti; A rappresenta un gruppo tn cui Ra, Rb, m ed n hanno i significati in precedenza definiti, L rappresenta un atomo di alogeno od un gruppo OH; Q rappresenta un gruppo R20- od un gruppo R3N(R4)- in cui R2, R3 ed R4 hanno i significati precedentemente definiti; Wa rappresenta un gruppo Wi od un gruppo W2 come definiti in precedenza. (Π) (la) in which: R, Ri, X, Xi, X2 and Y have the previously defined meanings; A represents a group tn of which Ra, Rb, m and n have the previously defined meanings, L represents a halogen atom or an OH group; Q represents a group R20- or a group R3N (R4) - in which R2, R3 and R4 have the previously defined meanings; Wa represents a Wi group or a W2 group as defined above. 3. Processo per la preparazione dei composti di formula generale (I) in cui W rappresenta un gruppo scelto tra W3, un gruppo Wi od un gruppo W2 in cui n = 1, comprendente l' eterificazione di uh fenolo o tiofenolo di formula generale (IV) con un composto di formula generale (V) a dare composti di formula generale (Ib), secondo lo schema di reazione 2: Schema 2 3. Process for the preparation of compounds of general formula (I) in which W represents a group selected from W3, a Wi group or a W2 group in which n = 1, comprising the etherification of uh phenol or thiophenol of general formula ( IV) with a compound of general formula (V) to give compounds of general formula (Ib), according to reaction scheme 2: Scheme 2 OV) db) ili cui : R, Ri, X, Xlf X2, Y e Z assumono i significati precedentemente definiti; Qi rappresenta un gruppo OV) db) whose: R, Ri, X, Xlf X2, Y and Z take on the previously defined meanings; Qi represents a group oppure , in cui R2, R3i R4 ed m assumono i significati precedentemente definiti; Li rappresenta un atomo di alogeno, oppure un gruppo RLS020- in cui RL rappresenta un gruppo alchilico od aloalchilico Ci-C4 od un gruppo fenilico eventualmente sostituito da gruppi alchilici C1-C4. Wb rappresenta un gruppo W3 come sopra definito; oppure rappresenta un gruppo Wi od un gruppo W2, come definiti in precedenza, in cui n = 1. or, in which R2, R3i R4 and m take on the previously defined meanings; Li represents a halogen atom, or an RLS020- group in which RL represents a C1-C4 alkyl or haloalkyl group or a phenyl group optionally substituted by C1-C4 alkyl groups. Wb represents a group W3 as defined above; or it represents a Wi group or a W2 group, as defined above, where n = 1. 4. Processo per la preparazione dei composti di formula generale (I) in cui W ed Y insieme rappresentano una catena -N (R6)0CCR7R80—, comprendente la reazione di un pirrolilamminofenolo di formula (VI) con un composto di formula (VII) a dare un pirrolil-benzossazinone di formula generale (le), il quale può essere successivamente convertito ai composti di formula generale (Id) per condensazione con un composto di formula generale (Vili), secondo lo schema 3. Schema 3 4. Process for the preparation of compounds of general formula (I) in which W and Y together represent a chain -N (R6) 0CCR7R80—, comprising the reaction of a pyrrolylaminophenol of formula (VI) with a compound of formula (VII) to give a pyrrolyl-benzoxazinone of general formula (le), which can be subsequently converted to compounds of general formula (Id) by condensation with a compound of general formula (VIII), according to scheme 3. Scheme 3 in cui: R, R1, X, X1, X2, R7 ed R8 assumono i significati in precedenza definiti; L2 rappresenta un atomo di alogeno, un gruppo OH, un gruppo alcossilico C1-C4; L3 ed L4 rappresentano un atomo di alogeno oppure un gruppo RLS020- in cui RL rappresenta un gruppo alchilico od aloalchilico C1-C4 od un gruppo fenilico eventualmente sostituito da gruppi alchilici C1-C4. R6' assume i significati in precedenza definiti per il gruppo Re eccettuato il significato di atomo di idrogeno. in which: R, R1, X, X1, X2, R7 and R8 take on the previously defined meanings; L2 represents a halogen atom, an OH group, a C1-C4 alkoxy group; L3 and L4 represent a halogen atom or an RLS020- group in which RL represents a C1-C4 alkyl or haloalkyl group or a phenyl group optionally substituted by C1-C4 alkyl groups. R6 'takes on the meanings previously defined for the group Re except for the meaning of hydrogen atom. 5. Composizioni erbicide comprendenti supporti solidi, diluenti liquidi, tensioattivi od altri additivi speciali ed almeno uno dei composti secondo la rivendicazione 1. 5. Herbicidal compositions comprising solid supports, liquid diluents, surfactants or other special additives and at least one of the compounds according to claim 1. 6. Composizioni secondo la rivendicazione precedente in cui la concentrazione dei composti è compresa tra 1 e 90%. 6. Compositions according to the preceding claim in which the concentration of the compounds is between 1 and 90%. 7. Metodo per il controllo delle erbe infestanti in aree coltivate che consiste nell'applicare a dette aree un composto secondo la rivendicazione 1 o una composizione secondo la rivendicazione 5. 7. Method for the control of weeds in cultivated areas which consists in applying to said areas a compound according to claim 1 or a composition according to claim 5. 8. Metodo secondo la rivendicazione 7 in cui i composti attivi vengono applicati al terreno a dosi comprese tra 1 e 1000 g per ettaro. 8. Method according to claim 7 wherein the active compounds are applied to the soil at doses ranging from 1 to 1000 g per hectare.
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