AR079524A1 - CYANOBUTIRATES REPLACED WITH HERBICIDE ACTION, PROCESS TO PREPARE THEM, HERBICIDE COMPOSITION CONTAINING THEM AND METHOD TO CONTROL INDENATED VEGETATION - Google Patents

CYANOBUTIRATES REPLACED WITH HERBICIDE ACTION, PROCESS TO PREPARE THEM, HERBICIDE COMPOSITION CONTAINING THEM AND METHOD TO CONTROL INDENATED VEGETATION

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Publication number
AR079524A1
AR079524A1 ARP100104739A AR079524A1 AR 079524 A1 AR079524 A1 AR 079524A1 AR P100104739 A ARP100104739 A AR P100104739A AR 079524 A1 AR079524 A1 AR 079524A1
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AR
Argentina
Prior art keywords
alkyl
haloalkyl
groups
alkoxy
alkylthio
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Spanish (es)
Original Assignee
Basf Se
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Application filed by Basf Se filed Critical Basf Se
Publication of AR079524A1 publication Critical patent/AR079524A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
    • A—HUMAN NECESSITIES
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • A—HUMAN NECESSITIES
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
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    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
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    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
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    • C07C317/00—Sulfones; Sulfoxides
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    • C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
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    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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    • 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
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    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms

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  • Chemical & Material Sciences (AREA)
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  • 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)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Reivindicacion 1: Un compuesto de cianobutirato, caracterizado porque tiene la formula 1 en donde las variables tienen el siguiente significado R es halogeno, ciano, nitro, alquilo C1-4, haloalquilo C1-4, alquenilo C2-6, alquinilo C2-6, alcoxi C1-4, alquiltio C1-4, Z-(tri-alquil C1-4)sililo; R1 es hidrogeno, Z-CN, alquilo C1-8, Z-cicloalquilo C3-6, haloalquilo C1-8, alcoxi C1-4-alquilo C1-4, alquiltio C1-4-alquilo C1-4, alquenilo C3-8, Z-cicloalquenilo C3-6, alquinilo C3-6, NRiRii, Z-(tri-alquil C1-4)sililo, Z-N=C(Ra)2, Z-C(Ra)=NRa, Z-C(=T)Ra, Z-P(=T)(Ra)2, Z- fenilo, un heterociclo saturado, insaturado o aromático monocíclico de 3 a 7 miembros o bicíclico de 9 o 10 miembros que contiene 1, 2, 3 o 4 heteroátomos seleccionados del grupo que consiste en O, N y S, que puede tener grupos de carbonilo o tiocarbonilo y que se une mediante carbono o nitrogeno, T es O o S; Ra es hidrogeno, TH, alquilo C1-8, haloalquilo C1-4, Z-cicloalquilo C3-6, alquenilo C2-8, Z-cicloalquenilo C5-6, alquinilo C2-8, Z-alcoxi C1-6, Z-haloalcoxi C1-4, Z-alqueniloxi C3-8, Z-alquiniloxi C3-8, Z-alquiltio C1-4, Z-haloalquiltio C1-4, Z-alqueniltio C3-8, Z-alquiniltio C3-8, NRiRii, alquilsulfonilo C1-6, oxi-C1-3-alquilenoxi, Z-Brb3-, ZC(=T)RA, Z-T-C(=T)RA, Z-(tri-alquil C1-4)sililo, Z-fenilo, Z-fenoxi, Z-fenilamino o un heterociclo monocíclico de 3 a 7 miembros o bicíclico de 9 o 10 miembros que contiene 1, 2, 3 o 4 heteroátomos seleccionados del grupo que consiste en O, N y S, en donde los grupos cíclicos son no sustituidos o pueden tener 1, 2, 3 o 4 grupos Rb y/o grupos carbonilo o tiocarbonilo; Ri, Rii independientemente entre si, son hidrogeno, alquilo C1-8, haloalquilo C1-4, alquenilo C3-8, alquinilo C3-8, Z-cicloalquilo C3-6, Z-alcoxi C1-8, Z-alquiltio C1-8, Z-haloalcoxi C1-8, Z-haloalquiltio C1-8, Z-C(=T)RA, en donde RA es TH, alquilo C1-4, alcoxi C1-4, o alquiltio C1-4; Ri y Rii, junto con el átomo de nitrogeno al que están unidos, también pueden formar un heterociclo monocíclico de 3 a 7 miembros o bicíclico de 9 o 10 miembros, que contiene 1, 2, 3 o 4 heteroátomos seleccionados del grupo que consiste en O, N y S y que puede tener grupos carbonilo o tiocarbonilo; Rb independientemente entre sí, es Z-CN, Z-TH, Z-NO2, Z-halogeno, alquilo C1-8, haloalquilo C1-4, alquenilo C2-8, alquinilo C2-8, Z-alcoxi C1-8, Z-alquiltio C1-8, Z-haloalquiltio C1-8, Z-haloalcoxi C1-8, Z-cicloalquilo C3-10, T-Z-cicloalquilo C3-10, Z-C(=T)Ra, NRiRii, Z-(tri-alquil C1-4)sililo, Z-fenilo y S(O)mRbb, en donde Rbb es alquilo C1-8 o haloalquilo C1-6; m es 0, 1 o 2; Rb, junto con el grupo Rb unido al átomo de carbono adyacente, también puede formar un anillo saturado o parcial o totalmente insaturado de 5 o 6 miembros que, además de átomos de carbono, puede contener 1, 2 o 3 heteroátomos seleccionados del grupo que consiste en O, N y S; Z es un enlace covalente o alquileno C1-8; n es 0, 1, 2, 3, 4 o 5; R2, R3, R4 independientemente entre sí, son halogeno, ciano, nitro, N=C=T, alquilo C1-4, alcoxi C1-4, alquiltio C1-4, S(O)mRbb, NRiRii, haloalquilo C1-4, haloalcoxi C1-4, haloalquiltio C1-4; en donde, si el índice x es 2 o 3, los grupos R4 pueden ser idénticos o diferentes; x es 0,1, 2 o 3; en donde en los grupos R y R1 y sus substituyentes, las cadenas de carbono y/o los grupos cíclicos pueden ser parcial o totalmente sustituidos con grupos Ra y/o Rb, o un N-oxido o una sal de aquél adecuada en la agricultura; siempre que R2 y R3 no sean ambos cloro, si los índices n y x son 0 y R1 es alquilo C1-4 o H; y R2 y R3 no sean ambos fluor, si el índice n es 1, el índice x es 0 o 3 y R y R4 son fluor y R1 es alquilo C1-4. Reivindicacion 15: Un método para controlar la vegetacion indeseada, caracterizado porque comprende permitir que una cantidad eficaz como herbicida de al menos un compuesto de cianobutirato de la formula (1) o una sal de éste aceptable en la agricultura de acuerdo con cualquiera de las reivindicaciones 1 a 12 actue en las plantas, sus semillas y/o su hábitat.Claim 1: A cyanobutyrate compound, characterized in that it has the formula 1 wherein the variables have the following meaning R is halogen, cyano, nitro, C1-4 alkyl, C1-4 haloalkyl, C2-6 alkenyl, C2-6 alkynyl, C1-4 alkoxy, C1-4 alkylthio, Z- (tri-C1-4 alkyl) silyl; R1 is hydrogen, Z-CN, C1-8 alkyl, Z3-6 cycloalkyl, C1-8 haloalkyl, C1-4 alkoxy-C1-4 alkyl, C1-4 alkylthio-C1-4 alkyl, C3-8 alkenyl, Z3-6 cycloalkenyl, C3-6 alkynyl, NRiRii, Z- (tri-C 1-4 alkyl) silyl, ZN = C (Ra) 2, ZC (Ra) = NRa, ZC (= T) Ra, ZP ( = T) (Ra) 2, Z-phenyl, a saturated 3-, 7-membered or 9 or 10-membered monocyclic or monocyclic heterocyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, which can have carbonyl or thiocarbonyl groups and which is linked by carbon or nitrogen, T is O or S; Ra is hydrogen, TH, C1-8 alkyl, C1-4 haloalkyl, Z3-6 cycloalkyl, C2-8 alkenyl, Z5-6 cycloalkenyl, C2-8 alkynyl, Z- C1-6 alkoxy, Z-haloalkoxy C1-4, Z3-8 alkenyloxy, C3-8 alkynyloxy, C1-4 alkyloxy, Z4-4 haloalkylthio, C3-8 alkenylthio, C3-8 alkynylthio, NRiRii, C1 alkylsulfonyl -6, oxy-C1-3-alkyleneoxy, Z-Brb3-, ZC (= T) RA, ZTC (= T) RA, Z- (tri-C 1-4 alkyl) silyl, Z-phenyl, Z-phenoxy, Z-phenylamino or a 3- or 7-membered monocyclic or 9 or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, wherein the cyclic groups are unsubstituted or they can have 1, 2, 3 or 4 Rb groups and / or carbonyl or thiocarbonyl groups; Ri, Rii independently of each other, are hydrogen, C1-8 alkyl, C1-4 haloalkyl, C3-8 alkenyl, C3-8 alkynyl, Z3-6 cycloalkyl, Z- C1-8 alkoxy, Z- C1-8 alkylthio , Z-haloalkoxy C1-8, Z-haloalkylthio C1-8, ZC (= T) RA, wherein RA is TH, C1-4 alkyl, C1-4 alkoxy, or C1-4 alkylthio; Ri and Rii, together with the nitrogen atom to which they are attached, can also form a 3- to 7-membered monocyclic or 9 or 10-membered bicyclic heterocycle, containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and which may have carbonyl or thiocarbonyl groups; Rb independently of one another, is Z-CN, Z-TH, Z-NO2, Z-halogen, C1-8 alkyl, C1-4 haloalkyl, C2-8 alkenyl, C2-8 alkynyl, Z- C1-8 alkoxy, Z - C1-8 alkylthio, Z- haloalkyl C1-8, Z-haloalkoxy C1-8, Z-cycloalkyl C3-10, TZ-cycloalkyl C3-10, ZC (= T) Ra, NRiRii, Z- (tri-alkyl C1 -4) silyl, Z-phenyl and S (O) mRbb, wherein Rbb is C1-8 alkyl or C1-6 haloalkyl; m is 0, 1 or 2; Rb, together with the group Rb attached to the adjacent carbon atom, can also form a saturated or partially or totally unsaturated ring of 5 or 6 members which, in addition to carbon atoms, can contain 1, 2 or 3 heteroatoms selected from the group that consists of O, N and S; Z is a covalent bond or C1-8 alkylene; n is 0, 1, 2, 3, 4 or 5; R2, R3, R4 independently of one another, are halogen, cyano, nitro, N = C = T, C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio, S (O) mRbb, NRiRii, C1-4 haloalkyl, C1-4 haloalkoxy, C1-4 haloalkylthio; where, if the index x is 2 or 3, the groups R4 can be identical or different; x is 0.1, 2 or 3; wherein in the R and R1 groups and their substituents, the carbon chains and / or the cyclic groups can be partially or totally substituted with Ra and / or Rb groups, or an N-oxide or a suitable salt thereof in agriculture ; provided that R2 and R3 are not both chlorine, if the indexes n and x are 0 and R1 is C1-4 alkyl or H; and R2 and R3 are not both fluorine, if the index n is 1, the index x is 0 or 3 and R and R4 are fluorine and R1 is C1-4 alkyl. Claim 15: A method of controlling unwanted vegetation, characterized in that it comprises allowing an effective amount as a herbicide of at least one cyanobutyrate compound of the formula (1) or a salt thereof acceptable in agriculture according to any of the claims 1 to 12 act on plants, their seeds and / or their habitat.

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