Phenyl-methoxyimino-glyoxylic acid derivatives as pesticides

Details Phenyl-methoxyimino-glyoxylic acid derivatives as pesticides Phenyl-methoxyimino-glyoxylic acid derivatives as pesticides

2000-09-27

2002-04-16

Geist, Gary (Department: 1623)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

Reexamination Certificate

active

06372787

ABSTRACT:

The present invention relates to new 2-phenyl-methoxyimino-glyoxylic acid derivatives having microbicidal, insecticidal and acaricidal activity, a process for the preparation thereof, new intermediates for the preparation thereof, agrochemical compositions containing these active ingredients, as well as their usage in the control and prevention of plant-pathogenic fungi, acarids and insects in agriculture and in the field of hygiene.
The new compounds correspond to formula I
wherein
A is a group OCHR
4
or N═CR
4
;
Y is O or NH,
R
1
is C
1
-C
6
-alkyl;
R
2
is C
1
-C
6
-alkyl or C
1
-C
6
-alkyl substituted by 1 to 5 fluorine atoms;
R
3
is C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkoxy, C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkynyl, C
2
-C
6
-alkynyloxy, C
1
-C
6
-alkoxycarbonyl, CN or halogen, whereby the above-mentioned groups, with the exception of CN and halogen, may be substituted by one or more identical or different substitutents selected from the group comprising halogen, cyano, nitro, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, aminocarbonyl, C
1
-C
6
-alkylaminocarbonyl, di-C
1
-C
6
-alkylaminocarbonyl, C
2
-C
6
-alkenyloxy, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, whereby the cyclic radicals in turn may be substituted by one or more identical or different substitutents selected from the group comprising halogen, cyano, nitro, C
1
-C
6
-alkyl, C
1
-C
6
halogenoalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-halogenoalkoxy, 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, optionally substituted benzyl, optionally substituted benzyloxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heteroaryl and optionally substituted heteroaryloxy, whereby the optionally substituted aromatic groups are unsubstituted or mono- to tri-substituted by the same or different substituents selected from halogen, C
1
-C
6
-alkyl, C
1
-C
6
-halogenoalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-halogenoalkoxy, C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkynyl, C
3
-C
6
-alkynyloxy, C
1
-C
6
-alkoxycarbonyl, CN or OCN; or
R
3
is aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, whereby the above-mentioned groups may be substituted by one or more identical or different substitutents selected from the group comprising halogen, C
1
-C
6
-alkoxy, halogeno-C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, halogeno-C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulfinyl, halogeno-C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl, halogeno-C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylcarbonyl, halogeno-C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, halogeno-C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylamino-carbonyl, di-(C
1
-C
6
-alkyl)-aminocarbonyl, whereby the alkyl groups may be identical or different, C
1
-C
6
-alkylaminothiocarbonyl, di-(C
1
-C
6
-alkyl)-aminothiocarbonyl, whereby the alkyl groups may be identical or different, C
1
-C
6
-alkylamino, di-(C
1
-C
6
-alkyl)-amino, NO
2
, an unsubstituted C
1
-C
4
-alkylenedioxy group or one which is substituted once to four times by C
1
-C
4
-alkyl and/or by halogen, or CN, SF
3
and QR
5
;
Q is a direct bond, O, O(C
1
-C
6
-alkylene), (C
1
-C
6
-alkylene)O, S(═O)p, S(═O)p(C
1
-C
6
-alkylene), (C
1
-C
6
-alkylene)S(═O)p, C
1
-C
8
-alkylene, C
2
-C
6
-alkenylene or C
2
-C
6
-alkynylene;
R
5
is a C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl group either unsubstituted or substituted by 1 to 3 halogen atoms, a (C
1
-C
4
-alkyl)
3
Si group, whereby the alkyl groups may be identical or different, CN, an unsubstituted or mono- to penta-substituted C
3
-C
6
-cycloalkyl, aryl, hetaryl or heterocyclyl group, whereby the substituents are selected from the group comprising halogen, C
1
-C
6
-alkyl, halogeno-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, halogeno-C
1
-C
6
-alkoxy, phenoxy and CN;
p is 0, 1 or 2;
R
4
is methyl, ethyl or cyclopropyl;
R
6
is hydrogen or methyl.
Formula I should include all the possible isomeric forms, as well as mixtures, e.g. racemic mixtures, and any [E/Z] mixtures.
Alkyl—as a group per se and as a structural element of other groups and compounds, such as halogenoalkyl, alkoxy and alkylthio—is either straight-chained, 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 se and as a structural element of other groups and compounds, such as halogenoalkenyl—is either straight-chained, for example vinyl, 1-methylvinyl, allyl, 1-butenyl or 2-hexenyl, or branched, for example isopropenyl.
Alkynyl—as a group per se and as a structural element of other groups and compounds, such as halogenoalkynyl—is either straight-chained, for example propargyl, 2-butynyl or 5-hexynyl, or branched, for example 2-ethynylpropyl or 2-propargylisopropyl.
Alkylenedioxy is —O(alkylene)O—.
Alkylene—as a group per se and as a structural element of other groups and compounds, such as O(alkylene), (alkylene)O, S(═O)p(alkylene), (alkylene)S(═O)p or alkylenedioxy— is either straight-chained, for example —CH
2
CH
2
—, —CH
2
CH
2
CH
2
— or —CH
2
CH
2
CH
2
CH
2
—, or branched, for example —CH(CH
3
)—, —CH(C
2
H
5
)—, —C(CH
3
)
2
—, —CH(CH
3
)CH
2
— or —CH(CH
3
)CH(CH
3
)—.
Alkenylene is either straight-chained, for example vin-1,2-ylene, all-1,3-ylene, but-1-en-1,4-ylene or hex-2-en-1,6-ylene, or branched, for example 1-methylvin-1,2-ylene.
Alkynylene is either straight-chained, for example propargylene, 2-butynylene or 5-hexynylene, or branched, for example 2-ethynylpropylene or 2-propargylisopropylene.
Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine. Halogenoalkyl may contain indentical or different halogen atoms.
Aryl is phenyl or naphthyl, preferably phenyl.
Heteroaryl is a cyclic aromatic group with 5 to 9 ring members in one or two rings, 1 to 3 members of which are hetero atoms, selected from the group oxygen, sulphur and nitrogen. 1 to 2 benzene rings may be condensed onto the heterocycle, whereby the binding to the residual molecule takes place either via the hetero or the benzene moiety.
Examples are benzimidazolyl, benzisoxazolyl, benzisothiazolyl, benzocoumarinyl, benzofuryl, benzothiadiazolyl, benzothiazolyl, benzothienyl, benzoxazolyl, benzoxdiazolyl, quinazolinyl, quinolyl, quinoxalinyl, carbazolyl, dihydrobenzofuryl, furyl, imidazolyl, indazolyl, indolyl, isoquinolinyl, isothiazolyl, isoxazolyl, methylenedioxyphenyl, ethylenedioxyphenyl, naphthyridinyl, oxazolyl, phenanthridinyl, phthalazinyl, pteridinyl, purinyl, pyrazinyl, pyrazolyl, pyridazinyl, pyrazolo[3,4-b]pyridyl, pyridyl, pyrimidinyl, pyrrolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, thiazolyl, thienyl, triazinyl and triazolyl.
Pyridyl, pyrazinyl, pyrimidinyl, thiazolyl, quinolinyl and thienyl are preferred.
Heterocyclyl is a 5- to 7-membered non-aromatic ring with one to three hetero atoms selected from the group comprising N, O and S.
Aromatic 5- and 6-rings are preferred, which have a nitrogen atom as hetero atom and optionally a further hetero atom, preferably nitrogen or sulphur, especially nitrogen.
Thiazolinyl and oxazolinyl are preferred.
Of the compounds of formula I, those groups are preferred in which:
(1)
a) A is the group N═CR
4
; or
b) R
1
is methyl or ethyl, preferably methyl; or
c) R
2
is methyl, ethyl, fluoromethyl or trifluoroethyl, preferably methyl; or
d) R
3
is C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkynyl, C
3
-C
6
-alkynyloxy, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkyloxy or C
1
-C
6
-alkoxycarbonyl, whereby the above-mentioned groups may be partially or totally halogenated; and also CN, OCN or halogen; or
e) R
3
is phenyl which is unsubstituted or mono- to tri-substituted by identical or different subsituents from halogen, C
1
-C
6
-alkyl, C
1
-C
6
-halogenoalkyl, C
1
-C
6
-alkoxy, C
1
-C

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