Hetaryl-substituted benzyl phenyl ethers, method for the...

Details Hetaryl-substituted benzyl phenyl ethers, method for the... Hetaryl-substituted benzyl phenyl ethers, method for the...

2000-08-29

2003-06-24

Ramsuer, Robert W. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S377100

Reexamination Certificate

active

06583090

ABSTRACT:

The present invention relates to hetaryl-substituted benzyl phenyl ethers of the formula I
where:
Q is C(═CHOCH
3
)—COOCH
3
, C(═CHCH
3
)—COOCH
3
, C(═NOCH
3
)—COOCH
3
, C(═NOCH
3
)—CONHCH
3
, N(—OCH
3
)—COOCH
3
or
 a group F, G, H, or J
 where
# denotes the bond with the phenyl ring and
R
A
is hydrogen, cyano, halogen,
 C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-halocycloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-haloalkenyl, C
2
-C
6
-alkynyl, C
2
-C
6
-haloalkynyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
3
-C
6
-cycloalkyloxy, C
3
-C
6
-halocycloalkyloxy, C
2
-C
6
-alkenyloxy, C
2
-C
6
-haloalkenyloxy, C
2
-C
6
-alkynyloxy, C
2
-C
6
-haloalkynyloxy, acetyloxy,
 C
1
-C
6
-alkylthio, C
1
-C
6
-haloalkylthio, C
3
-C
6
-cycloalkylthio, C
2
-C
6
-alkenylthio, C
2
-C
6
-haloalkenylthio, C
2
-C
6
-alkynylthio, C
2
-C
6
-haloalkynylthio, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-haloalkylsulfinyl, C
3
-C
6
-cycloalkylsulfinyl, C
2
-C
6
-alkenylsulfinyl, C
2
-C
6
-haloalkenylsulfinyl, C
2
-C
6
-alkynylsulfinyl, C
2
-C
6
-haloalkynylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-haloalkylsulfonyl, C
3
-C
6
-cycloalkylsulfonyl, C
2
-C
6
-alkenylsulfonyl, C
2
-C
6
-haloalkenylsulfonyl, C
2
-C
6
-alkynylsulfonyl, C
2
-C
6
-haloalkynylsulfonyl,
 amino, C
1
-C
6
-alkylamino, C
1
-C
6
-dialkylamino, C
1
-C
6
-alkoxyamino, (C
1
-C
6
-alkyl) (C
1
-C
6
-alkoxy)amino, or
 unsubstituted heterocyclyl or heterocyclyl which is substituted by one to three groups R
4
;
R
B
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-cycloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-haloalkenyl, C
2
-C
6
-alkynyl or C
2
-C
6
-haloalkynyl;
R
C
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-halocycloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-haloalkenyl, C
2
-C
6
-alkynyl, C
2
-C
6
-haloalkynyl, hydroxyl, C
1
-C
2
-alkoxy, acetyloxy, C
2
-C
4
-alkylcarbonyl or C
2
-C
4
-alkoxycarbonyl;
X is five-membered hetaryl which is unsubstituted or substituted by a group Y
2
p
and contains one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom;
Y, Y
1
are halogen, cyano, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-haloalkenyl or C
1
-C
4
-alkoxy;
Y
2
is halogen, cyano, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-haloalkenyl, C
2
-C
6
-alkynyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylamino or C
1
-C
4
-alkylthio, or
 phenyl, phenoxy or benzyl, where the aromatic rings may be partially or fully halogenated or may carry one to three groups R
4
:
R
4
is halogen, cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, alkyl, haloalkyl, alkenyl, alkenyloxy, alkynyloxy, alkoxy, haloalkoxy, alkylthio, alkylamino, dialkylamio, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, where the alkyl groups in these radicals contain 1 to 6 carbon atoms and the abovementioned alkenyl or alkynyl groups in these radicals contain 2 to 8 carbon atoms;
 and/or one to three of the following radicals
cycloalkyl, cycloalkoxy, heterocyclyl, heterocyclyloxy, where the cyclic systems contain 3 to 10 ring members; aryl, aryloxy, arylthio, aryl-C
1
-C
6
-alkoxy, aryl-C
1
-C
6
-alkyl, hetaryl, hetaryloxy, hetarylthio, where the aryl radicals preferably contain 6 to 10 ring members, the hetaryl radicals 5 or 6 ring members, where the cyclic systems may be partially or fully halogenated or may be substituted by one to three groups R
5
or by one or two groups R
6
:
R
5
is halogen, cyano, nitro, hydroxyl, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkylcarbonyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy and C
1
-C
4
-alkylenedioxy which may be halogenated; and
R
6
is C(═NOR
d
) -&Ggr;
l
-R
d
′, where R
d
is hydrogen or C
1
-C
6
-alkyl, &Ggr; is oxygen, sulfur or NR
d
and l is 0 or 1;
m, n are 0, 1 or 2, where the radicals Y and Y
1
may be different if m or n=2;
p is 0, 1, 2 or 3, where the radicals Y
2
may be different if p=2 or 3;
and salts thereof.
Additionally, the invention relates to processes for preparing the compounds I and to the use of the compounds I for controlling harmful fungi and animal pests.
Phenoxymethylenephenylacetic acid methyl esters and methyl amides are known from EP-A 253 213, EP-A 254 426, EP-A 251 082, EP-A 278 595, EP-A 280 185, EP-A 299 694, EP-A 386 561, EP-A 398 692 and EP-A 477 631, and the corresponding methoxycarbamates are known from WO-A 93/15046. Hetaryl-substituted phenylacetic acid derivatives are disclosed in EP-A 811 614.
Cyclic amides which carry an ortho-substituted phenyl ring in the position ortho to the amide carbonyl group are disclosed in WO-A 95/14009, WO-A 96/17851, WO-A 96/26191, WO-A 96/36229, WO-A 96/36615, WO-A 96/36616, WO-A 96/38425, WO-A 97/00612, WO-A 97/02255, WO-A 97/05120, WO-A 97/19935, WO-A 98/05652, WO-A 98/20003 and WO-A 98/23155, and JP-A 09/104676 and JP-A 09/208565. Cyclic amides which carry a substituted heterocycle in the position ortho to the amide carbonyl group are disclosed in WO-A 96/36633.
The compounds described in the abovementioned publications are suitable for use as crop protection agents against harmful fungi and in some cases against animal pests.
However, their action is in many cases unsatisfactory.
It is an object of the invention to provide compounds having improved activity.
This object was achieved by the substituted benzyl phenyl ethers of the formula I. Furthermore, intermediates and processes for preparing the compounds I, and also the use of the compounds I and of compositions comprising them for controlling harmful fungi and animal pests, were found. The fungicidal action is preferred.
Compared with the known compounds, the compounds of the formula I have increased activity against harmful fungi and animal pests.
The compounds of the formula I differ from the compounds known from the abovementioned publications by the design of the phenoxy group, which is substituted by five-membered nitrogen heterocycles or heteroaromatics.
The compounds I can be obtained by different routes, and it is immaterial for the synthesis whether the group Q or the phenoxy group E is constructed first.
The bracket } in the formula E denotes the linkage point with the benzyl skeleton in the formula I.
The construction of the group —Q is known, for example, from the publications cited at the outset, and also from the following publications:
EP-A 254 426, EP-A 370 629, EP-A 463 488, EP-A 472 300 and EP-A 513 580.
Thus, for clarity, the term
Q# is used for C(═CHOCH
3
)—COOCH
3
, C(—CHCH
3
)—COOCH
3
, C(═NOCH
3
)—COOCH
3
, N(—OCH
3
)—COOCH
3
or the group F, G, H or J, or a suitable precursor thereof, and
L# is used for the phenoxy group E, or a suitable precursor thereof,
in the descriptions of the reactions below.
For compounds of the formulae IF and IH
preference is given to introducing the phenoxy group in the steps in which Q# is nitro or, in the case of IF, is the group F, and, in the case IH, is the group H.
For compounds of the formulae IG and IJ
preference is given to introducing the phenoxy group in the steps in which Q# is the group G and the group J, respectively.
The synthesis of the compounds I is generally carried out by reacting phenols of the formula II with benzyl derivatives of the formula III#.
In the formula III#, L is a nucleofuge leaving group, such as halogen or alkyl- or arylsulfonate, preferably bromine, chlorine, mesylate, tosylate or triflate.
1) This reaction is usually carried out at 0°C. to 180° C., preferably at 20° C. to 60° C., in an inert organic solvent in the presence of a base [cf. EP-A 254 426; EP-A 463 488; WO-A 93/15046; W

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