Tetrahydropyridines as pesticides

Details Tetrahydropyridines as pesticides Tetrahydropyridines as pesticides

2002-02-25

2003-10-28

Morris, Patricia L. (Department: 1609)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S352000, C514S357000, C514S358000, C546S329000, C546S330000, C546S333000, C546S339000, C546S340000, C546S342000, C546S343000

Reexamination Certificate

active

06638940

ABSTRACT:

The object of the present invention is a compound of formula
wherein
R
1
and R
2
, independently of one another, are halogen, C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, halogen-C
1
-C
6
-alkyl, halogen-C
3
-C
6
-cycloalkyl, C
2
-C
4
-alkenyl, C
2
-C
4
-alkinyl, halogen-C
2
-C
4
-alkenyl, halogen-C
2
-C
4
-alkinyl, C
1
-C
6
-alkoxy, halogen-C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkinyloxy, halogen-C
2
-C
6
-alkenyloxy, halogen-C
2
-C
6
-alkinyloxy, —SF
5
, —C(═O)N(R
5
)
2
, —O—C(═O)N(R
5
)
2
, —CN, —NO
2
, —S(═O)
2
N(R
5
)
2
, —S(═O)
p
—C
1
-C
6
-alkyl, —S(═O)
p
-halogen-C
1
-C
6
-alkyl, —O—S(═O)
p
—C
1
-C
6
-alkyl, —O—S(═O)
p
-halogen-C
1
-C
6
-alkyl, phenyl, benzyl, phenoxy or benzyloxy, wherein each of the phenyl, benzyl, phenoxy or benzyloxy radicals is either un-substituted or mono- to penta-substituted in the aromatic ring, independently of each other, by substituents selected from the group consisting of halogen, cyano, NO
2
, C
1
-C
6
-alkyl, halogen-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy and halogen-C
1
-C
6
-alkoxy;
R
3
is hydrogen, OH, halogen, C
1
-C
6
-alkoxy, or —O—C(═O)—C
1
-C
6
-alkyl;
R
4
is C
1
-C
6
-alkyl, halogen-C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, halogen-C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkoxy, halogen-C
1
-C
6
-alkoxy, C
2
-C
4
-alkenyl, C
2
-C
4
-alkinyl, halogen-C
2
-C
4
-alkenyl, halogen-C
2
-C
4
-alkinyl, C
1
-C
6
-alkoxy, halogen-C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkinyloxy, halogen-C
2
-C
6
-alkenyloxy, halogen-C
2
-C
6
-alkinyloxy, —C(═O)—C
3
-C
6
-alkyl, —C(═O)-halogen-C
1
-C
6
-alkyl, —C(═O)—OC
1
-C
6
-alkyl, —C(═O)—O-halogen-C
1
-C
6
-alkyl, —NR
6
—C(═O)—O—C
1
-C
6
-alkyl, —NR
6
—C(═O)—O-halogen-C
1
-C
6
-alkyl, —C(═O)N(R
5
)
2
, —O—C(═O)N(R
5
)
2
, —CN, —NO
2
, —S(═O)
2
N(R
5
)
2
, —S(═O)
p
—C
1
-C
6
-alkyl, —S(═O)
p
-halogen-C
1
-C
6
-alkyl, —O—S(═O)
p
—C
1
-C
6
-alkyl, —O—S(═O)
p
-halogen-C
1
-C
6
-alkyl;
benzyl, phenoxy, benzyloxy; or phenyl, benzyl, phenoxy or benzyloxy which is mono- to penta-substituted, independently of each other, by substituents selected from the group consisting of halogen, cyano, NO
2
, C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl, C
3
-C
8
-cycloalkyl-C
1
-C
6
-alkyl;
halogen-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
3
-C
8
-cycloalkoxy, C
3
-C
8
-cycloalkoxy-C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl-C
1
-C
6
-alkoxy, halogen-C
1
-C
6
-alkoxy, C
2
-C
4
-alkenyl, C
2
-C
4
-alkinyl, halogen-C
2
-C
4
-alkenyl, halogen-C
2
-C
4
-alkinyl, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkinyloxy, halogen-C
2
-C
6
-alkenyloxy, halogen-C
2
-C
6
-alkinyloxy, —NR
6
—C(═O)—O—C
1
-C
6
-alkyl, —NR
6
—C(═O)—O—C
2
-C
6
-alkenyl, —NR
6
—C(═O)—O-halogen-C
1
-C
6
-alkyl, —C(R
7
)═N—W—R
8
, phenyl, benzyl, phenoxy, benzyloxy, heterocyclyl and heterocyclyloxy, wherein, depending on the substitution possibility on the ring, the heterocyclyl and heterocyclyloxy radicals are optionally mono- to trisubstituted by substituents selected from the group consisting of halogen, C
1
-C
6
-alkyl, halogen-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, halogen-C
1
-C
6
-alkoxy, C
3
-C
6
-cycloalkyl-C
1
-C
6
-alkyl, cyano-C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkinyl, phenyl or benzyl;
the two R
5
independently of one another, are hydrogen or C
1
-C
6
-alkyl;
R
6
is hydrogen, C
1
-C
6
-alkyl or benzyl;
R
7
is halogen, C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl, C
3
-C
8
-cycloalkyl-C
1
-C
6
-alkyl, halogen-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
3
-C
8
-cycloalkoxy, C
3
-C
8
-cycloalkoxy-C
1
-C
6
-alkyl, halogen-C
1
-C
6
-alkoxy —NH(C
1
-C
6
-alkyl) or —N(C
1
-C
6
-alkyl)
2
;
R
8
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl, C
3
-C
8
-cycloalkyl-C
1
-C
6
-alkyl, halogen-C
1
-C
6
-alkyl or —C(═O)—C
1
-C
6
-alkyl;
m is 0, 1, 2, 3, 4 or 5;
n is 0, 1, 2, 3, 4 or 5;
p is 0, 1 or 2;
q is 0 or 1
W is O or NH or N—C
1
-C
6
-alkyl;
and, if appropriate, the E/Z isomers, E/Z isomeric mixtures and/or tautomers thereof, each in free form or in salt form;
a method of producing and the use of these compounds, pesticides whose active ingredient is selected from these compounds or from an agrochemically employable salt thereof, a method of producing and the use of these compositions, plant propagating material that has been treated with these compositions and a method of controlling pests.
In the literature, certain piperidine derivatives have been proposed as active ingredients in pesticides. The biological properties of these known compounds, however, are not fully satisfactory in the field of pest control, which is why there is a need to produce further compounds with pesticidal properties, especially for the control of insects and members of the order Acarina; this problem is solved according to the invention with the development of the present compounds of formula (I).
The compounds of formula (I) and where appropriate their tautomers can form salts, for example acid addition salts. These are formed for example with strong inorganic acids, typically mineral acids, e.g. sulphuric acid, a phosphoric acid or a hydrohalic acid, or with strong organic carboxylic acids, typically C
1
-C
4
alkanecarboxylic acids substituted where appropriate for example by halogen, e.g. acetic acid, such as optionally unsaturated dicarboxylic acids, e.g. oxalic, malonic, maleic, fumaric or phthalic acid, such as hydroxy-carboxylic acids, e.g. ascorbic, lactic, malic, tartaric or citric acid, or benzoic acid, or with organic sulphonic acids, typically C
1
-C
4
alkane or arylsulphonic acids substituted where appropriate for example by halogen, e.g. methane- or p-toluene-sulphonic acid. In a broader sense, compounds of formula (I) with at least one acid group can form salts with bases. Suitable salts with bases are for example metal salts, such as alkali or alkaline earth metal salts, e.g. sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, e.g. ethyl, diethyl, triethyl or dimethylpropylamine, or a mono-, di- or trihydroxy-lower alkylamine, e.g. mono-, di- or triethanolamine. Corresponding internal salts where appropriate may also be formed. The free form is preferred on the one hand. Of the salts of compounds of formula (I), the agrochemically beneficial salts are preferred. Hereinbefore and hereinafter, the free compounds of formula (I) or their salts are understood where appropriate to include also the corresponding salts, or the salts are understood to include also the free compounds of formula (I). The same applies to tautomers of compounds of formula (I) and salts thereof. Unless otherwise defined, the general terms used hereinabove and hereinbelow have the meanings given hereinbelow.
Halogen—as a group per se or as structural element of other groups and compounds such as haloalkyl, halocycloalkyl, haloalkenyl, haloalkinyl and haloalkoxy—is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine, mainly fluorine or chlorine, especially chlorine.
If not otherwise defined, carbon-containing groups and compounds each contain 1 to 20, inclusively, preferably 1 to 18, in particular 1 to 10, especially 1 to 6, in particular 1 to 4, especially 1 to 3, particularly 1 or 2, carbon atoms, with methyl being preferred in particular.
Alkyl—as a group per se and as structural element of other groups and compounds such as haloalkyl, alkoxy, alkoxyalkyl, haloalkoxy, alkoxycarbonyl, alkylthio, haloalkylthio, alkylsulphonyl and alkylsulphonyloxy—is, in each case with due consideration of the specific number of carbon atoms in the group or compound in question, either straight-chained, e.g. methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, n-decyl, n-dodecyl, n-hexadecyl or n-octadecyl, or branched, for example isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl or isohexyl.
Alkenyl and alkinyl—as groups per se and as structural elements of other groups and compounds, such as of haloalkenyl, haloalkinyl, alkenyloxy, haloalk

Affiliated with

Also associated with

Rating

Tetrahydropyridines 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 Tetrahydropyridines as pesticides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Tetrahydropyridines as pesticides will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3135144