N-alkoxy-n-phenylcarbamate derivatives

Details N-alkoxy-n-phenylcarbamate derivatives N-alkoxy-n-phenylcarbamate derivatives

2001-07-10

2002-11-26

Rotman, Alan L. (Department: 1625)

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

Organic compounds

Carboxylic acid esters

C560S029000, C560S030000, C560S312000, C514S274000, C514S345000, C514S478000, C514S485000

Reexamination Certificate

active

06486341

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to new N-alkoxy-N-phenylcarbamates 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 and in the field of hygiene.
DETAILED DESCRIPTION
The new N-alkoxy-N-phenylcarbamates fall within formula I,
wherein:
R
1
is C
1
-C
4
-alkyl or cyclopropyl;
R
2
is C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkinyl; 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
-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
-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 substituents selected from the group comprising halogen, cyano, nitro, C
1
-C
6
-alkyl, C
1
-C
6
-halogenalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-halogenalkoxy, 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 above-mentioned aromatic groups 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
-halogenalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-halogenalkoxy, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino and C
2
-C
6
-alkenyl; or
R
3
signifies aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy 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, halogen-C
1
-C
6
-alkoxy, halogen-C
1
-C
6
-alkyl, C
1
-C
6
-alkylthio, halogen-C
1
-C
6
-alkylthio, C
1
-C
6
-alkylsulfinyl, halogen-C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl, halogen-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, halogen-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
, OH 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
-alkinylene;
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 penta-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, halogen-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, halogen-C
1
-C
6
-alkoxy, phenoxy, CN, SF
5
, NO
2
, C
1
-C
6
-alkylsulfinyl, halogen-C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl, halogen-C
1
-C
6
-alkylsulfonyl and C
1
-C
4
-alkylenedioxy, the latter being unsubstituted or mono- to tetrasubstituted by C
1
-C
4
-alkyl and/or by halogen;
p is 0, 1 or 2;
R
5
signifies hydrogen or methyl;
R
6
and R
7
are C
1
-C
4
-alkyl;
According to the present application, formula I includes all isomeric forms and mixtures thereof, 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 of halogenalkyl, 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 and as a structural element of other groups and compounds, such as of halogenalkenyl—is either straight-chained, e.g. vinyl, 1-methylvinyl, allyl, 1-butenyl or 2-hexenyl, or branched, e.g. isopropenyl.
Alkinyl—as a group per se and as a structural element of other groups and compounds, such as of halogenalkinyl—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, pudnyl, 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.
Preference is given to pyrazolinyl, thiazolinyl and oxazolinyl.
Of the compounds of formula I, those groups are preferred, wherein:
(1)
a) R
1
is methyl, ethyl or cyclopropyl, preferably methyl; or
b) R
2
is methyl, ethyl, fluoromethyl or trifluoroethyl, preferably methyl; or
c) 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 wholly halogenated; furthermore CN, OCN or halogen

Affiliated with

Also associated with

Rating

N-alkoxy-n-phenylcarbamate derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with N-alkoxy-n-phenylcarbamate derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and N-alkoxy-n-phenylcarbamate derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2934641