AR080160A1 - 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
AR080160A1
AR080160A1 ARP110100418A ARP110100418A AR080160A1 AR 080160 A1 AR080160 A1 AR 080160A1 AR P110100418 A ARP110100418 A AR P110100418A AR P110100418 A ARP110100418 A AR P110100418A AR 080160 A1 AR080160 A1 AR 080160A1
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AR
Argentina
Prior art keywords
alkyl
haloalkyl
alkoxy
groups
alkylthio
Prior art date
Application number
ARP110100418A
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Spanish (es)
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Basf Se
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Publication date
Application filed by Basf Se filed Critical Basf Se
Publication of AR080160A1 publication Critical patent/AR080160A1/en

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    • C07C255/00Carboxylic acid nitriles
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    • C07C255/32Carboxylic 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
    • C07C255/41Carboxylic 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
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    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
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    • A01N37/00Biocides, 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
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    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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    • C07C255/32Carboxylic 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
    • C07C255/42Carboxylic 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
    • C07C255/44Carboxylic 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 at least one of the singly-bound nitrogen atoms being acylated
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    • C07C271/44Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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Abstract

Composiciones que los comprenden y su uso como herbicidas, así como un método para controlar la vegetacion indeseada. 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 o 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 C3-8, 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 o 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-alquilenoxi C1-3, Z-C(=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 sí, 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-haloalcoxi C1-8, Z-alquiltio C1-8, Z-haloalquiltio 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, independientemente entre sí, son halogeno, ciano, nitro, alquilo C1-4, alcoxi C1-4, S(O)mRbb, NRiRii, haloalquilo C1-4 o haloalcoxi C1-4; en donde en los grupos R y R1 y sus subsustituyentes, 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 el índice n es 0 o 1 y R es halogeno o Rn es 3,5-Cl2 y R1 es alquilo C1-4 o H; y R2 y R3 no sean ambos fluor, si el índice n es 1 y R es halogeno y R1 es alquilo C1-4.Compositions that comprise them and their use as herbicides, as well as a method to control unwanted vegetation. 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- alkynyl 6, C1-4 alkoxy, C1-4 alkylthio or 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, C3-8 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 or 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, C1-3 oxy-alkyleneoxy, ZC (= T) -RA, ZTC (= T) -RA, Z- (tri-C 1-4 alkyl) silyl, Z-phenyl, Z-phenoxy, Z-phenylamino or a monocyclic heterocycle of 3 to 7 members or bicyclic of 9 or 10 members containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, wherein the cyclic groups are unsubstituted or may 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 haloalkoxy, Z- C 1-8 alkylthio, C1-8 haloalkylthio, C3-10 cycloalkyl, C3-10 TZ-cycloalkyl, 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, independently of one another, are halogen, cyano, nitro, C1-4 alkyl, C1-4 alkoxy, S (O) mRbb, NRiRii, C1-4 haloalkyl or C1-4 haloalkoxy; 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 salt thereof suitable in agriculture; provided that R2 and R3 are not both chlorine, if the index n is 0 or 1 and R is halogen or Rn is 3,5-Cl2 and R1 is C1-4 alkyl or H; and R2 and R3 are not both fluorine, if the index n is 1 and R is halogen and R1 is C1-4 alkyl.

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