Phenoxyacetic acid derivatives and their use as herbicides

Details Phenoxyacetic acid derivatives and their use as herbicides Phenoxyacetic acid derivatives and their use as herbicides

1999-11-05

2002-01-08

Raymond, Richard L. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C560S009000, C560S011000, C560S035000, C560S060000, C560S061000, C560S062000, C562S426000, C562S429000, C562S440000, C562S470000, C562S471000, C562S472000, C562S624000, C504S240000, C504S242000, C504S244000, C504S254000, C504S260000, C504S289000, C504S291000, C504S323000, C504S310000, C504S313000, C504S315000, C504S317000, C504S321000, C504S322000, C544S321000, C544S332000, C546S300000, C546S312000, C546S335000, C549S068000, C549S077000, C549S496000, C549S480000, C558S007000, C558S414000

Reexamination Certificate

active

06337306

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to novel phenoxyacetic acid derivatives, compositions containing them, processes and intermediates for their preparation, and their use as herbicides.
BACKGROUND ART
Japanese Patent Publication No. Sho 62-48649 discloses the preparation and fungicidal or plant growth regulator activity for the following acrylic acid ester derivatives, stereoisomers thereof, and metal complexes of general formula:
wherein, V′ represents an oxygen or sulfur atom; X′ and Y′, may be the same or different selected from a hydrogen or halogen atom, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroring, optionally substituted alkynyl, haloalkyl, alkoxy, optionally substituted haloalkoxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, nitrile, —CO
2
R
3
′, —CONR
4
′R
5
′, or —COR
6
′ group, or X′ and Y′ being at the adjacent position on a phenyl ring, may form an aromatic condensed ring or an aliphatic condensed ring optionally containing one or more hetero atoms; Z′ represents optionally substituted methylene, optionally substituted amino, oxygen or sulphur and when Z′ is a substituted methylene group, the substituent may join the 2-position of the phenyl ring to form a non-aromatic fused ring; R
1
′ and R
2
′ each independently represent an alkyl group having from one to four carbon atoms optionally substituted by one or more halogen atoms; R
3
′, R
4
′, R
5
′ and R
6
′ are the same or different groups selected from a hydrogen atom, optionally substituted alkyl, cycloalkyl, alkenyl, alkynyl, optionally substituted aryl, optionally substituted aralkyl and cycloalkyl. However it has not been disclosed or suggested that any 3-alkoxy-2-phenoxyacrylate derivatives having a substituted alkyl substituent(in particular a haloalkyl or hydroxyalkyl substituent) on the benzene ring possess useful herbicidal properties.
OBJECTS OF THE INVENTION
It is an object of the invention to provide new phenoxyacetic acid derivatives useful as herbicides, and processes for their preparation.
A second object of the invention is to provide herbicidal compositions and herbicidal methods of use for herbicidal phenoxyacetic acid derivatives.
A third object of the invention is to provide phenoxyacetic acid derivatives which possess selective herbicidal activity.
A fourth object of the invention is to provide phenoxyacetic acid derivatives effective as low dose herbicides.
A fifth object of the invention is to provide phenoxyacetic acid derivatives which possess good residual activity.
These and other objects of the invention can be achieved in whole or in part.
DESCRIPTION OF THE INVENTION
The present invention provides phenoxyacetic acid derivatives of formula
wherein:
R
1
and R
2
each represents independently a hydrogen atom, optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted cycloalkyl or —C
m
H
2m
(optionally substituted phenyl);
X represents a halogen atom, cyano, lower alkoxycarbonyl, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl, lower alkoxy, lower alkylthio, lower alkylsulphinyl, lower alkylsulfonyl, lower haloalkoxycarbonyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, halocycloalkyl, lower haloalkoxy, lower haloalkylthio, lower haloalkylsulphinyl, lower haloalkylsulfonyl, nitro, amino, lower alkylamino, lower dialkylamino, optionally substituted phenoxy, lower alkylcarbonylamino, carbamoyl, lower alkylcarbamoyl, lower dialkylcarbamoyl or SF5;
n and m represent 0, 1 or 2;
A represents halogen atom, hydroxy, or A′ wherein A′ represents OR
3
, S(O)
K
R
3
; or represents a formula II:
R
3
represents optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted lower alkylcarbonyl, optionally substituted lower alkenylcarbonyl, optionally substituted lower alkynylcarbonyl, optionally substituted cycloalkylcarbonyl, optionally substituted phenylcarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted cycloalkenyl, optionally substituted cycloalkenylcarbonyl, —C
p
H
2p
(optionally substituted phenyl), —C
q
H
2q
(optionally substituted heteroaryl), —(C
r
H
2r
) CO
2
alkyl, —(C
s
H
2s
) cycloalkyl, —CO(C
t
H
2t
)Y, —(C
u
H
2u
) COCH
2
(optionally substituted phenyl), —(C
f
H2
f
) O (optionally substituted phenyl), —(C
g
H
2g
) S (optionally substituted phenyl), or —(C
j
H
2j
) O (C
z
H
2z
) (optionally substituted phenyl);
k represents zero, one or two;
f, g, j, z, p, q, r, s, t and u represent one or two;
Y represents optionally substituted phenyl, optionally substituted phenoxy, optionally substituted heteroaryl, optionally substituted phenylthio, alkoxy or optionally substituted heteroaryloxy;
R
4
represents a hydrogen atom, cyano, optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted cycloalkyl, optionally substituted phenyl, or optionally substituted heteroaryl;
R
5
represents optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted lower alkoxy, optionally substituted lower alkenyloxy, optionally substituted lower alkynyloxy, optionally substituted cycloalkyloxy, optionally substituted heteroaryloxy, optionally substituted cycloalkenyloxy, , optionally substituted heteroaryl, —C
v
H
2v
(optionally substituted phenyl), —OC
w
H
2w
(optionally substituted phenyl), —(C
x
H
2x
) O (optionally substituted phenyl), optionally substituted lower alkylthio, optionally substituted phenylthio, —SC
y
H
2y
(optionally substituted phenyl) or optionally substituted phenoxy;
v, w, x and y represent one or two;
a geometric isomer thereof;
and agriculturally acceptable salts thereof, which possess valuable herbicidal properties.
In the phenoxyacetic acid derivatives of the present invention, there are two different stereoisomers, syn and anti [in other words, cis (Z), and trans (E) isomers] at a double bond. It will be understood that the present invention embraces both the pure isomers and mixtures thereof.
In certain cases the substituents R
1
, R
2
, R
3
, R
4
, R
5
, A and X contribute to optical isomerism and/or stereo isomerism. All such forms are embraced by the present invention.
By the term “agriculturally acceptable salts” is meant salts the cations or anions of which are known and accepted in the art for the formation of salts for agricultural or horticultural use. Preferably the salts are water-soluble. Suitable salts with bases, include alkali metal (e.g. sodium and potassium), alkaline earth metal (e.g. calcium and magnesium), ammonium and amine (e.g. diethanolamine, triethanolamine, octylamine, morpholine and dioctylmethylamine) salts. Suitable acid addition salts, e.g. formed by compounds of formula I containing an amino group, include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates and nitrates and salts with organic acids for example acetic acid.
It is understood that in the above definitions used in formula (I) all of the optionally substituted groups may have as the optional substituent one or more halogen atoms.
It is also understood that for optionally substituted cycloalkyl, optionally substituted cycloalkenyl and for other optionally substituted groups which incorporate cycloalkyl or cycloalkenyl portions, the optional substituent may be selected from lower alkyl, lower alkenyl, lower alkynyl, lower haloalkyl and halogen.
It is also understood that for optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted phenoxy, optionally

Affiliated with

Also associated with

Rating

Phenoxyacetic acid derivatives and their use as herbicides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Phenoxyacetic acid derivatives and their use as herbicides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Phenoxyacetic acid derivatives and their use as herbicides will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2856093