Dihydrotriazolone derivatives as pesticides

Details Dihydrotriazolone derivatives as pesticides Dihydrotriazolone derivatives as pesticides

2000-12-13

2002-08-20

Morris, Patricia L. (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S063000, C548S110000, C548S263200, C548S263600, C548S263800, C548S264600

Reexamination Certificate

active

06436981

ABSTRACT:

The present invention relates to new dihydrotriazolone derivatives having microbicidal, insecticidal and acaricidal activity, a process for their preparation, new intermediates for the preparation thereof, agrochemical compositions containing these active ingredients, as well as the use thereof in the control and prevention of plant-pathogenic fungi, acarids and insects in agriculture, horticulture and in the field of hygiene.
The new compounds fall within formula I,
wherein:
Y signifies halogen, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio or hydroxy;
R
1
signifies methyl, ethyl or cyclopropyl;
R
2
signifies C
1
-C
6
-alkyl or C
1
-C
6
-alkyl substituted by 1 to 5 fluorine atoms;
R
3
signifies 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
-alkinyl, C
2
-C
6
-alkinyloxy, C
1
-C
6
-alkoxycarbonyl or CN, whereby, with the exception of CN, the above-mentioned groups may be substituted by one or more identical or different substituents 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
-alkylamino-carbonyl, di-C
1
-C
6
-alkylaminocarbonyl, C
2
-C
6
-alkenyloxy, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkoxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, whereby the cyclic radicals in turn may be substituted by one or more identical or different substituents selected from the group comprising halogen, cyano, nitro, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, 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; or
R
3
signifies aryl, heteroaryl, heterocyclyl, aryloxy, hetaryloxy or heterocyclyloxy, whereby the above-mentioned groups may be substituted by one or more identical or different substituents selected from the group comprising halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, halo-C
1
-C
6
-alkoxy, halo-C
1
-C
6
-alkyl, C
1
-C
6
-alkylthio, halo-C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulfonyl, halo-C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkyl-sulfonyl, halo-C
1
-C
6
-alkylsulfonyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkinyl, C
3
-C
6
-alkinyloxy, C
1
-C
6
-alkylcarbonyl, halogen-C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, halo-C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylaminocarbonyl, 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 mono- to tetra-substituted by C
1
-C
4
-alkyl and/or by halogen, or CN, SF
5
and QR
4
;
Q signifies 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
-alkenylene;
R
4
signifies an unsubstituted C
2
-C
6
-alkenyl- or C
2
-C
6
-alkinyl group or one which is 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 tetra-substituted C
3
-C
6
-cycloalkyl, aryl, heteroaryl or heterocyclyl group, whereby the substituents are selected from the group comprising halogen, C
1
-C
6
-alkyl, halo-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, halogen-C
1
-C
6
-alkoxy, phenoxy and CN;
p is 0, 1 or 2;
R
5
signifies hydrogen or methyl.
Formula I is to include all possible isomeric forms and mixtures thereof, e.g. racemic mixtures and any [E/Z] mixtures.
Alkyl 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 is either straight-chained, e.g. vinyl, 1-methylvinyl, allyl, 1-butenyl or 2-hexenyl, or branched, e.g. isopropenyl.
Alkinyl is either straight-chained, e.g. propargyl, 2-butinyl or 5-hexinyl, or branched, e.g. 2-ethinylpropyl or 2-propargylisopropyl.
Alkylenedioxy is —O(alkylene)O—.
Alkylene is either straight-chained, e.g. —CH
2
CH
2
—, —CH
2
CH
2
CH
2
— or —CH
2
CH
2
CH
2
CH
2
—, or branched, e.g. —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, e.g. vin-1,2-ylene, all-1,3-ylene, but-1-en-1,4-ylene or hex-2-en-1,6-ylene, or branched, e.g. 1-methylvin-1,2-ylene.
Alkinylene is either straight-chained, e.g. propargylene, 2-butinylene or 5-hexinylene, or branched, e.g. 2-ethinylpropylene or 2-propargylisopropylene.
Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
Halogenalkyl may contain identical or different halogen atoms.
Aryl signifies phenyl or naphthyl, preferably phenyl.
Heteroaryl signifies a cyclic aromatic group with 5 to 9 ring members in one or two rings, of which 1 to 3 members are hetero atoms selected from the group oxygen, sulphur and nitrogen. 1 to 2 benzene rings may be condensed on the heterocycle, the binding to the residual molecule taking place either through the hetero or the benzene moiety.
Examples are benzimidazolyl, benzisoxazolyl, benzisothiazolyl, benzocumarinyl, 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.
Preference is given to pyridyl, pyrazinyl, pyrimidinyl, thiazolyl, quinolinyl and thienyl. Heterocyclyl signifies a 5- to 7-membered, non-aromatic ring with one to three hetero atoms selected from the group comprising N, O and S. Preference is given to non-aromatic 5- and 6-rings that have one nitrogen atom as a hetero atom and optionally one further hetero atom.
Piperidinyl, morpholinyl, pyrrolidinyl, pyrazolinyl, thiazolinyl and oxazolinyl are preferred.
Of the compounds of formula I, those groups are preferred, wherein:
(1) a) Y is chlorine, bromine, hydroxy, methoxy, or methylthio; or
b) R
1
is 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
-alkinyl, C
3
-C
6
-alkinyloxy, 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; also CN, OCN or halogen; or
e) R
3
is phenyl which is unsubstituted or mono- to tri-substituted by identical or different substituents from halogen, C
1
-C
6
-alkyl, C
1
-C
6
-halogenalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkinyl, C
3
-C
6
-alkinyloxy, C
1
-C
6
-alkoxycarbonyl, CN, OCN; optionally substituted benzyl, optionally substituted phenyl, or optionally substituted phenoxy; or
f) R
3
is pyridyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, which are unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, cyano, nitro, aminocarbonyl, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkylsulfonyl, C
1
-C
6
-alkylsulfoxyl, C
3
-C
6
-cycloalkyl, optionally substituted arylcarbonyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, C
1
-C
6
-a

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