Substituted (hetero) aryl compounds, process for their...

Details Substituted (hetero) aryl compounds, process for their... Substituted (hetero) aryl compounds, process for their...

1998-01-29

2002-11-19

Raymond, Richard L. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

C544S319000, C544S403000, C546S178000, C546S301000, C548S187000, C548S228000, C548S229000, C548S544000, C549S066000, C549S479000

Reexamination Certificate

active

06482947

ABSTRACT:

The invention relates to the technical area of crop-protection agents, in particular active ingredient/antidote combinations, which are highly suitable for use against competing weeds in crops of useful plants.
Use of crop treatment agents, in particular use of herbicides, can result in undesired damage to the treated crop plants. Many herbicides are not fully compatible (selective) with some important crop plants, such as corn, rice or cereals, so that their use is very restricted. They can therefore sometimes not be employed at all or only at such low application rates that the desired broad herbicidal activity against the weeds is not ensured. Thus, for example, many herbicides of the substance classes (A) mentioned below cannot be employed sufficiently selectively in corn, rice or in cereals. In particular in the case of post-emergence application of herbicides, phytotoxic side-effects on the crop plants occur, and it is desired to prevent or reduce this phytotoxicity.
It has already been disclosed to employ herbicides in combination with compounds which reduce the phytotoxicity of herbicides in crop plants without correspondingly reducing the herbicidal activity against the weeds. Such combination partners are known as “safeners” or “antidotes”.
EP-A-31 938 discloses the use of aryloxycarbonitriles and aryloxycarboxamide oximes as safeners for herbicides from the series consisting of the phenoxyphenoxycarboxylic esters, chloroacetanilides and dimedone derivatives. EP-A-170 906 describes, inter alia, phenoxycarboxylic ester oximes and EP-A-154 153 describes aryloxy compounds as safeners for phenoxyphenoxy and heteroaryloxyphenoxy herbicides.
EP-A-112 799 mentions 4-chlorophenoxy- and 4-chloro-2-mnethylphenoxyacetic acid as safeners for propargyl 2-[4-(3, 5-dichloropyridyl-2-oxy)phenoxy]propionate.
EP-A-293 062 describes the use of aryloxy compounds as safeners for cyclohexanedione herbicides, and EP-A-88 066 the use of 3,5-bis(trifluoromethyl)phenoxycarboxylic acid derivatives as safeners, in particular for acetamides, specifically for triallate.
EP-A-86 750 describes quinoline-8-oxyalkanecarbornitriles and quinoline-8-oxyalkanecarboxamide oximes as safeners for phenoxyphenoxyalkanecarboxylic esters and sulfonyl ureas. EP-A-94 349 discloses the use of corresponding carboxylic esters as safeners for herbicides from various structural classes.
DE 2637886 has already disclosed the use of 3-pyridyloxyalkanecarboxamides as safeners for herbicides from the triazine, carbamate and haloacetanilide series.
It has now been found that, surprisingly, a group of aryl and heteroaryl derivatives of the formula I below is highly suitable for protecting crop plants against the harmful effects of aggressive agrochemicals, in particular herbicides.
Aryl and heteroaryl derivatives which are suitable for protecting crop plants against the harmful effects of aggressive agrochemicals conform to the formula I
in which
R
1
and R
2
, independently of one another, are radicals of the formula
in which R, R
T
, R
4
, R
5
, R
6
, Y, T, Z, Q, A
i
, X
i
and q are as defined below, or
R
1
and R
2
are bonded to one another and together are a group of the formula
—CO—Q
1
-D—Q
2
—CO—
 in which
Q
1
and Q
2
, independently of one another, are as defined for Q and
D is a divalent group of the formula CR′R″ or C═O, where R′ and R″, independently of one another, are hydrogen or C
1
-C
4
-alkyl,
R
3
is hydrogen, halogen, C
1
-C
18
-alkyl, C
2
-C
8
-alkenyl, C
2
-C
8
-alkynyl, C
1
-C
18
-alkoxy, C
2
-C
8
-alkenyloxy, C
2
-C
8
-alkynyloxy, C
1
-C
18
-alkylthio, C
2
-C
8
-alkenylthio, C
2
-C
8
-alkynylthio, where each of the 9 last-mentioned radicals is in each case unsubstituted or substituted by one or more radicals from the group consisting of halogen, nitro and cyano, or is C
3
-C
12
-cycloalkyl which is unsubstituted or substituted by one or more radicals from the group consisting of C
1
-C
4
-alkyl, halogen, nitro and cyano, or is SiR
a
R
b
R
c
, in which R
a
, R
b
and R
c
, independently of one another, are C
1
-C
4
-alkyl, C
2
-C
4
-alkenyl, C
2
-C
4
-alkynyl or substituted or unsubstituted phenyl, or is a radical of the formula Ar′X′—, in which Ar′ and X′ are defined analogously to Ar and X,
X is O, S, NH—NH or NR
d
, where R
d
is defined analogously to R
4
, or is —CH
2
O—, —CH
2
S—, —CH(Ar)O— or —CH(Ar)S—,
Ar is an aromatic radical, for example an unsubstituted or substituted phenyl, naphthyl or heteroaryl radical, preferably a carbocyclic or carbobicyclic radical of the formula
 in which
(U) are identical or different radicals which, independently of one another, are hydrogen, halogen, cyano, nitro, amino or C
1
-C
8
-haloalkyl, C
1
-C
8
-haloalkoxy, C
1
-C
8
-alkyl, C
1
-C
8
-alkoxy, mono-(C
1
-C
4
-alkyl) amino, di-(C
1
-C
4
-alkyl)amino, C
1
-C
9
-alkylthio or C
1
-C
8
-alkylsulfonyl, where each of the 8 last-mentioned radicals is unsubstituted or substituted by one or more, preferably up to three identical or different substituents from the group consisting of halogen, C
1
-C
8
-haloalkoxy, nitro, cyano, hydroxyl, C
1
-C
8
-alkoxy, in which one or more, preferably up to three, CH
2
groups may be replaced by oxygen, C
1
-C
8
-alkylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
2
-C
8
-alkenylthio, C
2
-C
8
-alkynylthio, C
2
-C
8
-alkenyloxy, C
2
-C
8
-alkynyloxy, C
3
-C
7
-cycloalkyl, C
3
-C
7
-cycloalkoxy, mono- and di-(C
1
-C
4
-alkyl)amino and C
1
-C
8
-alkoxycarbonyl, and preferably hydrogen, halogen, C
1
-C6-haloalkyl, such as trifluoromethyl, C
1
-C
6
-haloalkoxy, such as difluoromethoxy, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy , C
1
-C
6
-alkythio, C
1
-C
6
-alkylsulfonyl, nitro, amino, (C
1
-C
2
-alkyl) amino, di-(C
1
-C
2
-alkyl) amino or cyano, and
o is an integer from 1 to 5, preferably from 1 to 3, and
p is an integer from 1 to 7, preferably from 1 to 3,
or Ar is a monocyclic or bicyclic heteroaryl radical from the group consisting of furyl, thienyl, pyrrolyl, pyrazolyl, thiazolyl, oxazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and quinolinyl, each of which is unsubstituted or substituted by one or more, preferably from one to three, of said radicals U,
R is hydrogen or an aliphatic, aromatic, heteroaromatic, araliphatic or heteroaraliphatic radical having 1 to 30 carbon atoms and, if desired, containing one or more functional groups, for example R is a hydrogen, C
1
-C
18
-alkyl, C
3
-C
12
-cycloalkyl, C
2
-C
8
-alkenyl, C
2
-C
8
-alkynyl, heterocyclyl, phenyl or heteroaryl radical,
where each of the above C-containing radicals, independently of one another, is unsubstituted or substituted by one or more radicals from the group consisting of halogen, cyano, thio, nitro, hydroxyl, C
1
-C
8
-alkyl, the latter only in the case of cyclic radicals, C
1
-C
8
-haloalkyl, C
2
-C
8
-alkoxy, C
2
-C
8
-alkenyloxy, C
2
-C
8
-alkynyloxy, C
1
-C
8
-haloalkoxy, C
2
-C
8
-alkylthio, C
2
-C
9
-alkenylthio, C
2
-C
8
-alkynylthio, C
3
-C
7
-cycloalkyl, C
3
-C
7
-cycloalkoxy, radicals of the formulae -NR*R** and —CO—NR*R** and —O—CO—NR*R**, where R* and R** in the three last-mentioned radicals are, independently of one another, hydrogen, C
2
-C
8
-alkyl, C
2
-C
8
-alkenyl, C
2
-C
8
-alkynyl, benzyl, phenyl or substituted phenyl, or together with the nitrogen atom are a 3- to 8-membered heterocyclic ring which may contain up to 2 further heteroatoms from the group consisting of N, O and S, and may be substituted by C
1
-C
4
-alkyl, and (C
1
-C
8
-alkoxy)carbonyl, (C
1
-C
8
-alkoxy)thiocarbonyl, (C
2
-C
8
-alkenyloxy)carbonyl, (C
1
-C
8
-alkylthio)carbonyl, (C
2
-C
8
-alkenylthio)carbonyl, (C
2
-C
8
-alkynylthio)carbonyl, (C
2
-C
8
-alkynyloxy carbonyl, formyl, (C
1
-C
8
-alkyl) carbonyl, (C
2
-C
8
-alkenyl) carbonyl, (C
2
-C
8
-alkynyl)carbonyl, C
1
-C
4
-alkylimino, C
1
-C
4
-alkoxyimino, (C
1
-C
8
-alkyl) carbonylamino, (C
2
-C
8
-alkenyl) carbonylamino, (C
2
-C
8
-alkynyl)carbonylamino, (C
1
-C
8
-alkoxy)carbonylamino, (C
2
-C
8
-alkenyloxy) carbonylamino, (C
2
-C
8
-alkynyloxy)carbonylamino, (C
1
-C
8
-alk

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