Trifluoromethylpyri(mi)dine carboxamides

Details Trifluoromethylpyri(mi)dine carboxamides Trifluoromethylpyri(mi)dine carboxamides

2002-01-18

2003-05-20

Balasubramanian, Venkataraman (Department: 1624)

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

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C546S316000, C514S256000, C514S357000

Reexamination Certificate

active

06566518

ABSTRACT:

The object of the present invention is a compound of the formula
wherein
R
1
and R
2
, independently of one another, are hydrogen, C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl, C
2
-C
20
-alkenyl or C
3
-C
20
-alkinyl; or mono- or poly-substituted C
1
-C
20
-alkyl, C
2
-C
20
-alkenyl or C
3
-C
20
-alkinyl;
aryl or heterocyclyl, or aryl or heterocyclyl which are substituted by one or more substituents selected from the group consisting of C
1
-C
6
-alkyl, halogen-C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
3
-C
6
-alkinyl, halogen, C
1
-C
6
-alkoxy, halogen-C
1
-C
6
-alkoxy, nitro, cyano, C
3
-C
8
-cycloalkyl, halogen-C
3
-C
8
-cycloalkyl, C
3
-C
6
-alkenyloxy, C
1
-C
4
-alkylthio and di-(C
1
-C
4
-alkyl)amine;
or —C(═O)—R
3
;
R
3
is hydrogen, OH, SH, C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
2
-C
6
-alkenyl, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkinyl, C
3
-C
6
-alkinyloxy, di-(C
1
-C
4
-alkyl)amine, aryl, heterocyclyl, aryloxy, benzyloxy or heterocyclyloxy;
C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
3
-C
6
-alkenyl, C
3
-C
6
-al-kenyloxy, C
3
-C
6
-alkinyl or C
3
-C
6
-alkinyloxy, which are substituted by one or more substituents selected from the group consisting of halogen, nitro, cyano, —OH, —SH, C
3
-C
8
-cycloalkyl, halogen-C
3
-C
8
-cycloalkyl and di-(C
1
-C
4
-alkyl)amine;
or aryl, heterocyclyl, aryloxy, benzyloxy or heterocyclyloxy, which are optionally substituted by one to three substituents selected from the group consisting of halogen, nitro, cyano, —OH, —SH, COOH, COH, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, halogen-C
1
-C
6
-alkyl, halogen-C
1
-C
6
-alkoxy, halogen-C
1
-C
6
-alkylthio, C
3
-C
8
-cycloalkyl, halogen-C
3
-C
8
-cycloalkyl and di-(C
1
-C
4
-alkyl)amine;
m is 0 or 1; and
X is CH or N;
and the compounds thereof, and where appropriate to E/Z isomers, to mixtures of E/Z isomers and/or to tautomers, in each case 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 literature, certain pyridine 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) may be present partly in the form of tautomers. Accordingly, any reference to compounds of formula (I) hereinbefore and hereinafter is understood to include also their corresponding tautomers, even if the latter are not specifically mentioned in each case.
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 hydroxycarboxylic 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. 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 tautomer 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, haloalkenyloxy, alkinyloxy or halo-alkinyloxy—are straight-chained or branched and respectively contain two or preferably one unsaturated carbon-carbon bond(s). Vinyl, prop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, prop-2-in-1-yl, but-2-in-1-yl and but-3-in-1-yl may be example.
Cycloalkyl—as a group per se and as a structural element of other groups and compounds, for example of alkyl—is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Cyclopentyl and cyclohexyl are preferred, in particular cyclopropyl.
Halogen-substituted carbon-containing groups and compounds, such as haloalkyl and haloalkoxy , can be partially halogenated or perhalogenated, in the case of polyhalogenation it being possible for the halogen substituents to be identical or different. Examples of haloalkyl—as a group per se and as structural element of other groups and compounds such as haloalkoxy, —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 oder CClFCHClF; propyl or isopropyl, mono- to heptasubstituted by fluorine, chlorine and/or bromine, such as CH
2
CHBrCH
2
Br, CF
2
CHFCF
3
, CH
2
CF
2
CF
3
, CF
2
CF
2
CF
3
, CH(CF
3
)
2
or CH
2
CH
2
CH
2
Cl; and butyl or one of its isomers, mono- to nonasubstituted by fluorine, chlorine and/or bromine, such as CF(CF
3
)CHFCF
3
, CF
2
(CF
2
)
2
CF
3
oder CH
2
(CF
2
)
2
CF
3
.
In di-(C
1
-C
4
-alkyl)amine, the two alkyl groups are independent of each other.
Aryl preferably signifies phenyl or naphthyl, especially phenyl.
Heterocyclyl signifies a 5- to 7-membered,

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