Cyanohydrazone derivatives

Details Cyanohydrazone derivatives Cyanohydrazone derivatives

2001-02-13

2002-07-09

Stockton, Laura L. (Department: 1626)

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

Organic compounds

Nitriles

Reexamination Certificate

active

06417386

ABSTRACT:

The invention relates to a pesticidal composition which comprises at least one compound of the formula
in which
A
1
and A
2
are independent of one another and are in each case a mono- or bicyclic aryl or hetaryl radical, each hetaryl radical independently of the other having 1 up to and including 4 hetero atoms selected from the group consisting of N, O and S;
A
1
is substituted with a substituent (R
3a
)
n
, and A
2
with a substituent (R
3b
)
n2
;
R
1
is —CN, halo—C
1
-C
6
alkyl or —C(═S)—N(R
5
)
2
(in which the two R
5
are independent of one another);
R
2
is hydrogen, —OH, C
1
-C
6
alkyl, C
1
-C
6
alkoxy, C
3
-C
6
cycloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, halo—C
1
-C
6
alkyl, halo—C
3
-C
6
alkenyl, halo—C
3
-C
6
alkynyl, benzyl or benzoyl, in which the benzyl or benzoyl radical is unsubstituted or mono- to trisubstituted in the aromatic ring by substituents which are independent of one another and selected from the group consisting of halogen, —CN, NO
2
, C
1
-C
6
alkyl, C
1
-C
6
alkoxy, halo—C
1
-C
6
alkyl and halo—C
1
-C
6
alkoxy; C
1
-C
6
alkoxy—C
1
-C
6
alkyl, cyano—C
1
-C
6
alkyl, —C(═X)—R
7
, —OC(═O)—R
7
, —C(═O)—C(═O)—R
7
, —S(═O)
p
N(R
6
)
2
(in which the two R
6
are independent of one another); cyano, —C
1
-C
6
alkyl—N(R
10
)—C(═O)—R
8
, —C
1
-C
6
alkyl-S—C(═S)—R
8
, —C
1
-C
6
alkyl-S(═O)
p
—R
9
, —S(═O)
p
—R
9
, or —CH
2
—N(R
10
)—SO
2
—R
9
;
R
3a
and R
3b
are independently of each other halogen, C
1
-C
6
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, halo—C
1
-C
6
alkyl, halo—C
2
-C
4
alkenyl, halo—C
2
-C
4
alkynyl, C
1
-C
6
alkoxy, halo—C
1
-C
6
alkoxy, C
2
-C
6
alkenyloxy, C
2
-C
6
alkynyloxy, halo—C
2
-C
6
alkenyloxy, halo—C
2
-C
6
alkynyloxy, —OH, —SF
5
, —CHO, —C(═O)—C
1
-C
6
alky), —C(═O)—halo—C
1
-C
6
alkyl, —C(═O)—OC
1
-C
6
alkyl, —C(═O)—O—halo—C
1
—C
6
alkyl, —O—C(═O)
2
N(R
6
)
2
(in which the two R
6
are independent of one another), —CN, —NO
2
, —S(═O)
2
N(R
6
)
2
(in which the two R
6
are independent of one another), —S(═O)
p
—C
1
—C
6
alkyl, —S(═O)
p
—halo—C
1
-C
6
alkyl, —O—S(═O)
p
—C
1
-C
6
alkyl, —O—S(═O)
p
—halo—C
1
-C
6
alkyl, phenyl, benzyl, phenoxy or benzyloxy, each of the phenyl, benzyl, phenoxy or benzyloxy radicals being unsubstituted or mono- to penta-substituted in the aromatic ring by substituents which are independent of one another and selected from the group consisting of halogen, cyano, NO
2
, C
1
-C
6
alkyl, halo—C
1
-C
6
alkyl, C
1
-C
6
alkoxy and halo—C
1
-C
6
alkoxy;
n
1
and n
2
are 0 or, depending on the substitution options on the ring systems A
1
and A
2
in question, independently of each other 1, 2, 3, 4 or 5;
X is O or S;
p is 0, 1 or 2;
R
5
radicals independently of one another are H or C
1
-C
8
alkyl;
R
6
radicals independently of one another are H, C
1
-C
8
alkyl, C
3
-C
6
cycloalkyl, phenyl or benzyl, the phenyl or benzyl group in the aromatic ring being unsubstituted or mono- to trisubstituted by substituents which are independent of one another and selected from the group consisting of halogen, —CN, NO
2
, C
1
-C
6
alkyl, C
1
-C
4
alkoxy, halo—C
1
-C
6
alkyl and halo—C
1
-C
6
alkoxy; or two alkyl radicals R
6
together with the nitrogen atom to which they are bonded form a five- to seven-membered ring in which a CH
2
group may be replaced by a hetero atom selected from the group consisting of O and S, or by NH, and where the five- to seven-membered ring is unsubstituted or mono- or di-substituted by C
1
-C
4
alkyl;
R
7
is H, C
1
-C
8
alkyl, C
2
-C
8
alkenyl, halo—C
1
-C
8
alkyl, halo—C
2
-C
8
alkenyl, C
1
-C
8
alkoxy, halo—C
1
-C
8
alkoxy, C
3
-C
6
cycloalkyl, phenyl, benzyl, phenoxy, benzyloxy or —N(R
6
)
2
(in which the two R
6
are independent of one another);
R
8
is C
1
-C
8
alkyl, C
1
-C
8
alkoxy, halo—C
1
-C
8
alkyl, halo—C
1
-C
8
alkoxy, C
1
-C
8
alkylthio, phenyl, benzyl or —N(R
6
)
2
(in which the two R
6
are independent of one another);
R
9
is C
1
-C
6
alkyl, halo—C
1
-C
4
alkyl or aryl which is unsubstituted or mono- to trisubstituted by substituents which are independent of one another and selected from the group consisting of C
1
-C
6
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
1
-C
4
alkoxy, halogen, cyano, halo—C
1
-C
4
alkyl, halo—C
2
-C
4
alkenyl, halo—C
2
-C
4
alkynyl, halo—C
1
-C
4
alkoxy and nitro; and
R
10
is H, C
1
-C
6
alkyl, C
3
-C
6
cycloalkyl, phenyl or benzyl, the phenyl and benzyl radicals being unsubstituted or mono- to trisubstituted in the aromatic ring by substituents which are independent of one another and selected from the group consisting of C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen, cyano, halo—C
1
-C
4
alkyl, halo—C
1
-C
4
alkoxy and nitro;
or, where appropriate, an E/Z isomer, EIZ isomer mixture and/or a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, with the exception of 1-phenyl-hydrazono-2-nitriloethylbenzene, as active ingredient and at least one auxiliary;
to compounds of the formula (Ia) defined below, E/Z isomers and/or tautomers thereof, in each case in free form or in salt form; to a process for the preparation and to the use of these compounds, E/Z isomers and tautomers; to a process for the preparation and to the use of these compositions; to intermediates, in free form or in salt form, for the preparation of these compounds, if appropriate to tautomers, in free form or in salt form, of these intermediates; and to a process for the preparation and to the use of these intermediates and tautomers thereof.
Certain phenylhydrazone derivatives are proposed in the literature as active ingredients in pesticides. However, the biological properties of these known compounds are not entirely satisfactory in the field of pest control, which is why there is a demand for providing further compounds which have pesticidal properties, in particular for controlling insects and representatives of the order Acarina, this object being achieved according to the invention by providing the present pesticides containing compounds of the formula (I).
Some compounds of the formula (I) contain asymmetric carbon atoms, which is why optically active forms of the compounds can occur. Owing to the presence of the C═N double bond, E- and Z-isomeric forms of the compounds may occur. Moreover, atropisomers of the compounds may occur. The formula (I) is intended to embrace all these isomeric forms which are possible and mixtures of these, for example racemates or E/Z isomer mixtures.
Unless otherwise defined, the general terms used hereinabove and hereinbelow have the meanings given in the following text.
Unless otherwise defined, carbon-containing groups and compounds contain in each case 1 up to and including 8, preferably 1 up to and including 6, in particular 1 up to and including 4, especially 1 or 2, carbon atoms.
Alkyl—as a group per se and as structural element of other groups and compounds, such as of haloalkyl, alkoxy or alkylthio—is, in each case with due consideration of the number of carbon atoms present in the relevant group or compound in every single case, either straight-chain, i.e. methyl, ethyl, propyl, butyl, pentyl or hexyl, or branched, e.g. isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl or isohexyl.
Alkenyl—as a group per se and as structural element of other groups and compounds, such as of alkenoxy, haloalkenyl or haloalkenoxy—is, in each case with due consideration of the number of carbon atoms present in the relevant group or compound in every single case, either straight-chain, e.g. vinyl, 1-methylvinyl, allyl, 1-butenyl or 2-hexenyl, or branched, e.g. isopropenyl.
Alkynyl—as a group per se and as structural element of other groups and compounds, such as haloalkynyl—is, in each case with due consideration of the number of carbon atoms present in the relevant group or compound in every single case, either straight-chain, e.g. propargyl, 2-butynyl or 5-hexynyl, or branched, e.g. 2-ethynylpropyl or 2-propargylisopropyl.
C
3
-C
6
-cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl or cyclo

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