Phenyl acetic acid derivatives as pesticides

Details Phenyl acetic acid derivatives as pesticides Phenyl acetic acid derivatives as pesticides

1999-06-22

2001-11-06

Stockton, Laura L. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

C514S538000, C514S563000, C560S035000, C560S042000, C564S149000, C564S168000, C504S312000

Reexamination Certificate

active

06313166

ABSTRACT:

DETAILED DESCRIPTION
The invention relates to novel pesticidally active compounds of the formula I
and to the isomers, and isomer mixtures, thereof which are possible, in which either
a) X is an N atom and
Y is OR
11
or N(R
12
)R
13
, or
b) X is CH and
Y is OR
11
,
and in which furthermore:
R
11
is C
1
-C
4
alkyl;
R
12
and R
13
, independently, are hydrogen or C
1
-C
4
alky;
A is an O atom or the group NR
4
;
R
1
is hydrogen, C
1
-C
4
alkyl, halo-C
1
-C
4
alkyl, cyclopropyl, cyano or methylthio;
R
2
is hydrogen, C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, a group
a group
 or thienyl;
D radicals are identical or different and are halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
2
haloalkyl, C
1
-C
2
haloalkoxy, C
3
-C
6
alkenyloxy, C
3
-C
6
alkynyloxy, C
1
-C
4
alkylenedioxy, cyano or nitro;
n is 0, 1, 2, 3 or 4;
Z is —O—, —O—(C
1
-C
4
alkyl)—, —(C
1
-C
4
alkyl)—O—, —S(O)
m
—, —(C
1
-C
4
alkyl)—S(O)
m
—, —S(O)
m
—(C
1
-C
4
alkyl)—,
m is 0, 1 or 2,
B is C
1
-C
6
alkyl, halo-C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl or is C
2
-C
6
alkenyl or C
2
-C
4
alkynyl-C
1
-C
2
alkyl, each of which is unsubstituted or substituted by 1 to 3 halogen atoms, or is aryl or heterocyclyl, each of these two, independently, being unsubstituted or mono- to pentasubstituted by C
1
-C
6
alkyl, halo-C
1
-C
6
alkyl, halogen, C
1
-C
6
alkoxy or
halo-C
1
-C
6
alkoxy, or a group
 or trimethysily;
R
5
, R
6
, R
7
, R
8
and R
9
, independently, are hydrogen, C
1
-C
4
alkyl or halogen and p is 0, 1, 2 or 3;
R
3
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl having 1 to 5 halogen atoms, C
1
-C
4
alkoxy-C
1
-C
2
alkyl, C
2
-C
4
alkenyl-C
1
-C
2
akyl, which is unsubstituted or substituted by 1 to 3 halogen atoms, C
2
-C
4
alkynyl-C
1
-C
2
-alkyl, C
3
-C
6
cycloalkyl which is unsubstituted or substituted by 1 to 4 halogen atoms, C
3
-C
6
-cycloalkyl-C
1
-C
4
alkyl which is unsubstituted or substituted by 1 to 4 halogen atoms, cyano-C
1
-C
4
alkyl; C
1
-C
4
alkoxycarbonyl-C
1
-C
2
alkyl, C
1
-C
4
alkoxycarbamoyl-C
1
-C
2
alkyl, phenyl-C
1
-C
3
alkyl which is unsubstituted or substituted by halogen, C
1
-C
3
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkyl, cyano, nitro or C
1
-C
4
alkylenedioxy, it being possible for the phenyl group to be monosubstituted to trisubstituted by identical or different substituents; phenyl which is unsubstituted or mono- to disubstituted, independently, by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen, C
1
-C
2
haloalkyl having 1 to 3 halogen atoms, nitro or cyano, or pyridyl which is unsubstituted or mono- to disubstituted, independently, by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen, C
1
-C
2
haloalkyl having 1 to 3 halogen atoms, nitro or cyano;
R
4
is C
1
-C
4
alkyl, phenyl, or
R
3
and R
4
together with the nitrogen atom to which they are bonded form a saturated or unsaturated 5- to 7-membered ring which is unsubstituted or substituted by C
1
-C
4
alkyl and which can have 1 to 3 additional hetero atoms selected from amongst N, O and S.
The compounds according to the invention have fungicidal, acaricidal and insecticidal properties and are suitable as active ingredients for use in agriculture, horticulture and the hygiene field.
The invention furthermore also relates to a process for the preparation of the compounds according to the invention, and to fungicidal, acaricidal and insecticidal compositions which comprise such compounds as active ingredients, and to the use of such compounds and compositions for controlling phytopathogenic fungi, Acarina and insects and for preventing such an attack.
If asymmetric carbon atoms exist in the compounds of the formula I, the compounds exist in optically active form. The compounds exist in any case in [E] and/or [Z] forms, merely because of the presence of the aliphatic, the oximino and the hydrazono double bonds. Furthermore, atropisomerism may exist The formula I is intended to embrace all these isomeric forms which are possible and their mixtures, for example racemic mixtures, and any [E/Z] mixtures.
Unless otherwise defined, the general terms used hereinabove and hereinbelow are intended to mean the following:
Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine, especially fluorine or chlorine.
Alkyl is either straight-chain, for example methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, ndecyl, ndodecyl, n-hexadecyl or n-octadecyl, or branched, for example isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl or isohexyl.
Alkenyl is straight-chain or branched alkenyl, for example vinyl, 1-methylvinyl, allyl, 1-butenyl, isopropenyl, in particular allyl.
Alkynyl is, for example, ethynyl, 1-propynyl or 1-butynyl, in particular propargyl.
Cycloalkyl is to be understood as meaning cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
Halogen-substituted groups such as haloalkyl and haloalkoxy can be partially or fully halogenated by identical or different substituents. Examples of haloalkyl are methyl which is mono- to trisubstituted by fluorine, chlorine and/or bromine, such as CHF
2
, CF
3
or CH
2
Cl; ethyl which is mono- to pentasubstituted by fluorine, chlorine and/or bromine, such as CH
2
CF
3
, CF
2
CF
3
, CF
2
CCl
3
, CF
2
CHCl
2
, CF
2
CHF
2
, CF
2
CFCl
2
, CH
2
CH
2
Cl, CF
2
CHBr
2
, CF
2
CHClF, CF
2
CHBrF or CClFCHClF; trifluoromethyl is very particularly preferred.
Straight-chain C
1
-C
4
alkylenedioxy is —O—CH
2
—O—, —O—CH
2
CH
2
—O—, —O—CH
2
CH
2
CH
2
—O— or —O—CH
2
CH
2
CH
2
CH
2
—O—.
Aryl is, for example, phenyl or naphthyl in particular phenyl.
Heterocyclyl is a 5- to 7-membered aromatic or non-aromatic ring having one to three hetero atoms selected from the group consisting of N, O and S. Preferred are aromatic 5-and 6membered rings which have a nitrogen atom as hetero atom and, if appropriate, a further hetero atom, preferably nitrogen or sulfur, in particular nitrogen.
The term of the 5- to 7-membered ring which is formed by R
3
and R
4
together with the nitrogen atom to which they are bonded encompasses, in particular, pyrrolidine, piperidine, morpholine, thiomorpholine, hexamethyleneimine, imidazole, pytazole, pyrrole, 1,2,4-triazole, 1,2,3-triazole, tetrazole, isoxazole, oxazole, isoxazolidine, oxazolidine, thiazole, isothiazole, thiazoline and isothiazolidine.
Preferred within the scope of the invention are
(1) Compounds of the formula I in which either
a) X is an N atom and
Y is OCH
3
or NHCH
3
, or
b) X is CH and
Y is OCH
3
,
and in which furthermore:
A is an O atom or the group NR
4
;
R
1
is hydrogen, C
1
-C
4
alkyl, halo-C
1
-C
4
alkyl, cyclopropyl, cyano or methylthio;
R
2
is hydrogen, C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, a group
 a group
D radicals are identical or different and are halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
2
haloalkyl, C
1
-C
2
haloalkoxy, C
3
-C
6
alkenyloxy, C
3
-C
6
alkynyloxy, C
1
-C
4
alkylenedioxy, cyano or nitro;
n is 0, 1, 2, 3 or 4;
Z is —O—, —O—(C
1
-C
4
alkyl)—, —(C
1
-C
4
alkyl)—O—, —S(O)
m
—, —(C
1
-C
4
alkyl)—S(O)
m
—, —S(O)
m
—(C
1
-C
4
alkyl)—;
m is 0, 1 or 2;
B is C
1
-C
6
alkyl, halo-C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, or is C
2
-C
6
alkenyl or C
2
-C
4
alkynyl-C
1
-C
2
alkyl, each of which is unsubstituted or substituted by 1 to 3 halogen atoms, or is aryl or heterocyclyl, or aryl or heterocyclyl, each of these, independently, being monosubstituted to pentasubstituted by C
1
-C
6
alkyl, halo-C
1
-C
6
alkyl, halogen, C
1
-C
6
alkoxy or halo-C
1
-C
6
alkoxy, or a group
R
5
, R
6
, R
7
, R
8
and R
9
, independently, are hydrogen, C
1
-C
4
alkyl or halogen and p is 0, 1, 2 or 3;
R
3
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl having 1 to 5 halogen atoms, C
1
-C
4
alkoxy-C
1
-C
2
alkyl, C
2
-C
4
alkenyl-C
1
-C
2
alkyl which is unsubstituted or substituted by 1 to 3 halogen atoms, C
2
-C
4
alkynyl-C
1
-C
2
alkyl, C
3
-C
6
cycloalkyl which is unsubstituted or substituted by 1 to 4 halogen atoms, C
3
-C
6
cycloalkyl-C
1
-C
4
alkyl which is unsubstituted or substituted by 1 to 4 halogen atoms, cyano-C
1
-C
4
alkyl; C
1
-C
4
alkoxycarbonyl-C
1
-C
2
alkyl, phenyl-C
1
-C
3
alkyl wh

Affiliated with

Also associated with

Rating

Phenyl acetic acid derivatives as pesticides does not yet have a rating. At this time, there are no reviews or comments for this patent.

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

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2572049