Phenoxy-and thiophenoxy acrylic acid compounds as herbicides

Details Phenoxy-and thiophenoxy acrylic acid compounds as herbicides Phenoxy-and thiophenoxy acrylic acid compounds as herbicides

2002-06-05

2003-03-04

Qazi, Sabiha (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S209000, C504S227000, C504S229000, C504S236000, C504S238000, C504S239000, C504S242000, C504S130000, C544S242000, C544S298000, C544S309000, C544S215000, C544S216000, C544S219000, C544S220000, C548S543000, C548S545000

Reexamination Certificate

active

06528455

ABSTRACT:

The present invention relates to 2-phenoxy- and 2-thiophenoxyacrylic acid compounds of the formula I
in which
Z, V and W independently of one another are oxygen or sulfur,
R
1
is hydrogen or halogen and
R
2
is halogen, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-haloalkoxy;
R
3
is hydrogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-alkylamino-C
1
-C
6
-alkyl, (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl, 2,3-dihydrofuryl, 2,5-dihydrofuryl, tetrahydrofuryl, where each of the ten last mentioned groups may carry one, two or three substituents selected from the group consisting of:
halogen, nitro, cyano, hydroxyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkoxy-C
1
-C
6
-alkoxy, C
3
-C
6
-cycloalkoxy, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkylcarbonyloxy, (C
2
-C
6
-alkenyl)carbonyloxy, (C
2
-C
6
-alkynyl)carbonyloxy, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylideneiminooxy, ═N—OR
8
, —O—(C
n
H
2n−1
)═N—OR
8
where n=1, 2, 3, 4, 5 or 6,
phenyl, benzyloxy, phenoxy or phenylsulfonyl, where the three last mentioned groups may carry one, two or three substituents selected from the group consisting of halogen, nitro, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy or C
1
-C
6
-alkoxycarbonyl;
 is (C
3
-C
6
-alkenyloxy)carbonyl-C
1
-C
6
-alkyl, (C
3
-C
6
-alkynyloxy)carbonyl-C
1
-C
6
-alkyl, furyl or phenyl, where furyl and phenyl independently of one another may carry one, two or three substituents selected from the group consisting of halogen, nitro, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy or C
1
-C
6
-alkoxycarbonyl;
Het is an unsaturated five- or six-membered heterocyclic radical which is attached to the phenyl ring of I via a nitrogen atom and which is selected from among radicals of the formulae II-1 to II-19:
which
in the formula II-14 denotes a single bond or a double bond,
R
4
, R
4′
and R
4″
independently of one another are hydrogen, amino, C
1
-C
4
-alkylamino, di-C
1
-C
4
-alkylamino, saturated 5- or 6-membered N-bonded nitrogen heterocyclyl, C
3
-C
6
-cycloalkylamino, halogen, cyano, carboxyl, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-haloalkylthio, C
1
-C
6
-alkoxycarbonyl, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
3
-C
8
-cycloalkyl or C
3
-C
8
-cycloalkyl-C
1
-C
6
-alkyl, and R
4
in the formula II-14 also is a corresponding imino or alkylidene group if
denotes a double bond;
R
5
and R
5′
independently of one another are hydrogen, amino, hydroxyl, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-alkoxycarbonyl, C
3
-C
8
-cycloalkyl, C
3
-C
8
-cycloalkyl-C
1
-C
6
-alkyl, phenyl or phenyl-C
1
-C
6
-alkyl; and/or
in each case two of the radicals R
4
, R
4′
, R
4″
, R
5
and R
5′
together with the ring atoms of Het to which they are attached form a 4-, 5-, 6- or 7-membered ring which may be saturated or unsaturated, which may contain one or two nitrogen, oxygen and/or sulfur atoms as ring members and/or which may be substituted by one, two or three radicals selected from the group consisting of C
1
-C
4
-alkyl and halogen;
R
6
and R
7
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl or C
3
-C
6
-cycloalkyl, or together with the C atom to which they are attached form a 4-, 5-, 6- or 7-membered ring which may be saturated or unsaturated, which may contain one or two oxygen and/or sulfur atoms as ring members and/or which may be substituted by one, two or three substituents selected from the group consisting of C
1
-C
4
-alkyl and halogen;
R
8
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkylthio-C
1
-C
6
-alkyl, cyano-C
1
-C
6
-alkyl, (C
1
-C
6
-alkyl)carbonyl-C
1
-C
6
-alkyl, (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkyl or (C
1
-C
6
-alkoxy)carbonyl-C
2
-C
6
-alkenyl;
Q in the formula II-1 is O or S,
X and X′ independently of one another are O or S, and
Y is O, S or a group N—R
9
in which R
9
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl or C
3
-C
8
-cycloalkyl;
and the agriculturally useful salts of the compounds of the formula I.
Moreover, the invention relates to
the use of the compounds I as herbicides,
compositions which comprise the compounds I as herbicidally active substances,
methods for controlling undesirable vegetation using the compounds of the formula I, and
compounds of the formula III
 in which R
1
, R
2
, R
3
, V, W and Z are as defined above and R
y
is —N═C=O, —N═C═S, —NH—NH
2
, NO
2
or a group —NH—R
10
in which R
10
is hydrogen or C
1
-C
6
-alkylcarbonyl; and
compounds of the formula IV
 in which R
1
and R
2
are as defined above, Hal is a halogen atom, preferably chlorine or bromine, and R
3′
is selected from the group consisting of hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkyl and phenyl which may carry one, two or three substituents selected from the group consisting of halogen, cyano, C
1
-C
6
-alkyl, C
1
-C
5
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy and C
1
-C
6
-alkoxycarbonyl, and R
3
is preferably hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl or C
1
-C
6
-cyanoalkyl, the compounds of the formulae III and IV serving as intermediates for the preparation of the compounds I.
EP-A 255 047 discloses phenyluracils which have, at the phenyl ring, in the m-position to the uracil group, an ether group, a (thio)carbonyl group, which is attached via an oxygen atom, or a sulfonyloxy group.
EP-A 83 055 discloses N-(2-fluorophenyl)tetrahydrophthalimides which, in the 5-position of the phenyl ring, have a group which is attached via an oxygen atom or a nitrogen atom and which is derived from an &agr;-amino- or &agr;-hydroxycarboxylic acid.
It is an object of the present invention to provide novel herbicidally active compounds which allow better targeted control of undesirable plants than the known active compounds.
We have found that this object is achieved by the phenoxy- and phenylthioacrylic acid compounds of the formula I defined at the outset which, at the phenyl ring, have a 5- or 6-membered heterocycle Het of the formulae II-1 to II-19 defined at the outset which is attached via a nitrogen atom.
Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal activity. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
The compounds of the formula I can contain one or more chiral centers in the substituents, in which case they are present as enantiomer or diastereomer mixtures. The invention provides both the pure enantiomers or diastereomers and mixtures thereof.
Agriculturally useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the herbicidal activity of the compounds I. Thus, particularly suitable cations are the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which may, if desired, carry one to four C
1
-C
4
-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C
1
-C
4
-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C
1
-C
4
-alkyl)sulfoxonium.
Anions of useful acid addition salts are

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