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AR079191A1 - CYANOBUTIRATES REPLACED WITH HERBICIDE EFFECT, PREPARATION PROCEDURE AND METHOD TO COMBAT INDESEATED PLANTS - Google Patents

CYANOBUTIRATES REPLACED WITH HERBICIDE EFFECT, PREPARATION PROCEDURE AND METHOD TO COMBAT INDESEATED PLANTS

Info

Publication number
AR079191A1
AR079191A1 ARP100103695A AR079191A1 AR 079191 A1 AR079191 A1 AR 079191A1 AR P100103695 A ARP100103695 A AR P100103695A AR 079191 A1 AR079191 A1 AR 079191A1
Authority
AR
Argentina
Prior art keywords
alkyl
haloalkyl
alkynyl
cycloalkyl
alkenyl
Prior art date
Application number
Other languages
Spanish (es)
Original Assignee
Basf Se
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Se filed Critical Basf Se
Publication of AR079191A1 publication Critical patent/AR079191A1/en

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Classifications

    • 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
    • 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
    • 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
    • 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
    • C07C255/42—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
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
    • C07D307/20—Oxygen atoms

Landscapes

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

Abstract

Reivindicacion 1: Cianobutíratos caracterizados por la formula (1) en la que las variables tienen los siguientes significados: R es halogeno, ciano, nitro, C1-4-alquilo, C1-4-haloalquilo, C2-6-alquenilo, C2-6-alquinilo, Z-(tri-C1-4-alquil)sililo, R1 es hidrogeno, Z-CN, C1-8-alquilo, Z-C3-6-cicloalquilo, C1-8-haloalquilo, C3-8-alquenilo, Z-C3-6-cicloalquenilo, C3-8-alquinilo, Z-(tri-C1-4-alquil)sililo, Z-C(=O)-Ra, Z-P(=O)(Ra)2, Z-fenilo, heterociclo saturado, no saturado o aromático, monocíclico de 3 a 7 miembros, o bícíclico de 9 o 10 miembros, que está ligado por medio de C o N, que contiene 1, 2, 3 o 4 heteroátomos seleccionados de entre O, N y S, que puede estar parcial o completamente sustituido por grupos Ra y/o- Rb, Ra es hidrogeno, OH, C1-8-alquilo, C1-4-haloalquilo, Z-C3-6-cicloalquilo, C2-8-alquenilo, Z-C5-6-cicloalquenilo, C2-8-alquinilo, Z-C1-6-alcoxi, Z-C1-4-haloalcoxi, Z-C3-8-alqueniloxi, Z-C3-8-alquiniloxi, NRiRii, C1-6-alquilsulfonilo, Z-(tri-C1-4-alquil)sililo, Z-fenilo, Z-fenoxi, Z-fenilamino y heterociclo monocíclico de 5 o 6 miembros, o bicíclico de 9 o 10 miembros, que contiene 1, 2, 3 o 4 heteroátomos seleccionados de entre O, N y S, estando los grupos cíclicos no sustituidos o sustituidos por 1, 2, 3 o 4 grupos Rb; Ri,Rii significan independientemente entre si hidrogeno, C1-8-alquilo, C1-4-haloalquilo, C3-8-alquenilo, C3-8-alquinilo, Z-C3-6-cicloalquilo, Z-C1-8-alcoxi, Z-C1-8-haloalcoxi, Z-C(=O)-RA, significando RA OH o C1-4-alcoxi; Ri y Rii también pueden formar conjuntamente con el átomo de N al que están ligados, un heterociclo monocíclico de 5 o 6 miembros, o bicíclico de 9 o 10 miembros, que contiene 1, 2, 3 o 4 heteroátomos seleccionados de entre O, N y S; Rb significan independientemente entre si Z-CN, Z-OH, Z-NO2, Z-halogeno, C1-8-alquilo, C1-4-haloalquilo, C2-8-alquenilo, C2-8-alquinilo, Z-C1-8-alcoxi, Z-C1-8-haloalcoxi, Z-C3-10-cicloalquilo, O-Z-C3-10-cicloalquilo, Z-C(=O)Ra, NRiRii, Z-(tri-C1-4-alquil)sililo, Z-fenilo y S(O)mRbb, donde: Rbb significa C1-8-alquilo y C1-6-haloalquilo; m es 0,1 o 2; Rb también puede formar conjuntamente con el grupo Rb ligado al átomo de C vecino un anillo saturado, parcial o completamente insaturado, de cinco o seis miembros, que puede contener además de carbono 1, 2 o 3 heteroátomos seleccionados de entre O, N y S; Z es un enlace covalente o C1-8-alquileno; n es 0, 1, 2, 3, 4 o 5; R2, R3 significan independientemente entre si halogeno, ciano, nitro, C1-4-alquilo, C1-4-alcoxi, S(O)mRbb, NRiRii, C1-4-halogenoalquilo, C1-4-halogenoalcoxi; pudiendo las cadenas de carbono y/o los grupos cíclicos en los grupos R y R1 y sus sub-sustituyentes estar parcial o completamente sustituidos por grupos Ra y/o- Rb, siendo preciso, que a) R2 y R3 no signifiquen ambos cloro, cuando n = 0 y R1 es etilo, y b) R no significa fluor, cuando n = 1 o 2, R1 metilo, R2 es fluor y R3 es fluor, cloro o bromo; así como sus N-oxidos y sales apropiadas en la agricultura. Reivindicacion 13: Proceso caracterizado porque es para la preparacion de los compuestos de la formula 1 de acuerdo con una de las reivindicaciones 1 a 12 por reaccion de derivados de fenilacetonitrilo de la formula (2) bajo condiciones básicas con derivados de la formula (3), en el sentido de una adicion de Michael. Reivindicacion 15: Proceso para combatir el crecimiento de plantas indeseadas, caracterizado porque se hace actuar una cantidad efectiva herbicida de por lo menos un compuesto de cianobutirato de la formula 1 o de una sal agronomicamente util del mismo de acuerdo con una de las reivindicaciones 1 a 12 sobre las plantas, sus semillas y/o su hábitat.Claim 1: Cyanobutyrates characterized by the formula (1) in which the variables have the following meanings: R is halogen, cyano, nitro, C1-4-alkyl, C1-4-haloalkyl, C2-6-alkenyl, C2-6 -alkynyl, Z- (tri-C1-4-alkyl) silyl, R1 is hydrogen, Z-CN, C1-8-alkyl, Z-C3-6-cycloalkyl, C1-8-haloalkyl, C3-8-alkenyl, Z-C3-6-cycloalkenyl, C3-8-alkynyl, Z- (tri-C1-4-alkyl) silyl, ZC (= O) -Ra, ZP (= O) (Ra) 2, Z-phenyl, heterocycle saturated, unsaturated or aromatic, monocyclic of 3 to 7 members, or bicyclic of 9 or 10 members, which is linked by means of C or N, which contains 1, 2, 3 or 4 heteroatoms selected from O, N and S , which may be partially or completely substituted by groups Ra and / or -Rb, Ra is hydrogen, OH, C1-8-alkyl, C1-4-haloalkyl, Z-C3-6-cycloalkyl, C2-8-alkenyl, Z -C5-6-cycloalkenyl, C2-8-alkynyl, Z-C1-6-alkoxy, Z-C1-4-haloalkoxy, Z-C3-8-alkenyloxy, Z-C3-8-alkynyloxy, NRiRii, C1-6 -alkylsulfonyl, Z- (tri-C1-4-alkyl) silyl, Z -phenyl, Z-phenoxy, Z-phenylamino and 5- or 6-membered monocyclic heterocycle, or 9 or 10-membered bicyclic, containing 1, 2, 3 or 4 heteroatoms selected from O, N and S, the cyclic groups being not substituted or substituted by 1, 2, 3 or 4 Rb groups; Ri, Rii independently mean hydrogen, C1-8-alkyl, C1-4-haloalkyl, C3-8-alkenyl, C3-8-alkynyl, Z-C3-6-cycloalkyl, Z-C1-8-alkoxy, Z -C1-8-haloalkoxy, ZC (= O) -RA, meaning RA OH or C1-4-alkoxy; Ri and Rii can also form together with the N atom to which they are linked, a 5- or 6-membered monocyclic heterocycle, or 9 or 10-membered bicyclic, containing 1, 2, 3 or 4 heteroatoms selected from O, N and S; Rb independently means Z-CN, Z-OH, 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-C3-10-cycloalkyl, OZ-C3-10-cycloalkyl, ZC (= O) Ra, NRiRii, Z- (tri-C1-4-alkyl) silyl, Z -phenyl and S (O) mRbb, where: Rbb means C1-8-alkyl and C1-6-haloalkyl; m is 0.1 or 2; Rb can also form together with the group Rb linked to the neighboring C atom a saturated ring, partially or completely unsaturated, of five or six members, which may contain in addition to carbon 1, 2 or 3 heteroatoms selected from 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 mean each other halogen, cyano, nitro, C1-4-alkyl, C1-4-alkoxy, S (O) mRbb, NRiRii, C1-4-halogenoalkyl, C1-4-halogenoalkoxy; the carbon chains and / or the cyclic groups in groups R and R1 and their substituents being able to be partially or completely substituted by groups Ra and / or -Rb, being necessary that a) R2 and R3 do not mean both chlorine, when n = 0 and R1 is ethyl, and b) R does not mean fluorine, when n = 1 or 2, R1 methyl, R2 is fluorine and R3 is fluorine, chlorine or bromine; as well as its appropriate N-oxides and salts in agriculture. Claim 13: Process characterized in that it is for the preparation of the compounds of the formula 1 according to one of the claims 1 to 12 by reaction of phenylacetonitrile derivatives of the formula (2) under basic conditions with derivatives of the formula (3) , in the sense of an addition of Michael. Claim 15: Process for combating the growth of unwanted plants, characterized in that an effective herbicidal amount of at least one cyanobutyrate compound of formula 1 or an agronomically useful salt thereof according to one of claims 1 to is actuated 12 on plants, their seeds and / or their habitat.

ARP100103695 2009-10-09 2010-10-08 CYANOBUTIRATES REPLACED WITH HERBICIDE EFFECT, PREPARATION PROCEDURE AND METHOD TO COMBAT INDESEATED PLANTS AR079191A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP09172632 2009-10-09
EP09180018 2009-12-18

Publications (1)

Publication Number Publication Date
AR079191A1 true AR079191A1 (en) 2012-01-04

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Application Number Title Priority Date Filing Date
ARP100103695 AR079191A1 (en) 2009-10-09 2010-10-08 CYANOBUTIRATES REPLACED WITH HERBICIDE EFFECT, PREPARATION PROCEDURE AND METHOD TO COMBAT INDESEATED PLANTS

Country Status (4)

Country Link
AR (1) AR079191A1 (en)
TW (1) TW201127285A (en)
UY (1) UY32936A (en)
WO (1) WO2011042378A1 (en)

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EP2474226A1 (en) * 2011-01-07 2012-07-11 Basf Se Herbicidally active composition comprising cyanobutyrates
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CN103889954B (en) 2011-10-31 2016-12-07 拜耳知识产权有限责任公司 4 cyano group 3 phenyl 4 (the pyridine 3 base) butyrates that are replaced, they preparation method and as herbicide and the purposes of plant growth regulator
AR089249A1 (en) 2011-12-19 2014-08-06 Bayer Ip Gmbh 4-CIANO-3-PHENYL-4- (PIRIDIN-3-IL) SUBSTITUTED BUTANOATS, PROCEDURES FOR THEIR PREPARATION AND ITS USE AS HERBICIDES AND AS REGULATORS OF GROWTH OF PLANTS
CA2895585A1 (en) 2012-12-21 2014-06-26 Bayer Cropscience Ag Substituted 4-cyan-3-(pyridyl)-4-phenylbutanoates, method for the production thereof and uses as herbicides and plant growth regulators
AR096517A1 (en) 2013-06-07 2016-01-13 Bayer Cropscience Ag DERIVATIVES OF 5-HIDROXI-2,3-DIFENYLPENTANONITRILE REPLACED, PROCEDURES FOR THEIR PREPARATION AND ITS USE AS HERBICIDES AND / OR REGULATORS OF GROWTH OF PLANTS
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Also Published As

Publication number Publication date
UY32936A (en) 2011-06-30
WO2011042378A1 (en) 2011-04-14
TW201127285A (en) 2011-08-16

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