Isothiazole derivatives and their use as pesticides

Details Isothiazole derivatives and their use as pesticides Isothiazole derivatives and their use as pesticides

2002-11-07

2004-03-09

McKane, Joseph K. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S269000, C514S233800, C514S367000, C514S372000, C544S133000, C548S180000, C548S206000, C548S214000, C548S212000

Reexamination Certificate

active

06703347

ABSTRACT:

The present invention relates to azole derivatives, to processes for preparing them, to fungicidal, insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising them, to methods of using them to combat fungal diseases (especially fungal diseases of plants) and to methods of using them to combat and control insect, acarine, mollusc and nematode pests.
Azole and azine derivatives are disclosed in WO95/31448, WO97/18198, WO98/02424, WO98/05670 and WO98/17630.
The present invention provides a compound of formula (I):
where A is optionally substituted C
1-6
alkylene, optionally substituted C
2-6
alkenylene, optionally substituted C
2-6
alkynylene, optionally substituted cycloalkylene, optionally substituted C
1-6
alkylenoxy, optionally substituted oxy(C
1-6
)alkylene, optionally substituted C
1-6
alkylenethio, optionally substituted thio(C
1-6
)alkylene, optionally substituted C
1-6
alkylenamino, optionally substituted amino(C
1-6
)alkylene, optionally substituted [C
1-6
alkyleneoxy(C
1-6
)alkylene], optionally substituted [C
1-6
alkylenethio(C
1-6
)alkylene], optionally substituted [C
1-6
alkylenesulfinyl(C
1-6
)alkylene], optionally substituted [C
1-6
alkylenesulfonyl(C
1-6
)alkylene] or optionally substituted [C
1-6
alkyleneamino(C
1-6
)alkylene]; provided that A is not CH
2
or CH
2
O; B is N,N-oxide or CR
8
; Y is O, S or NR
9
; Z is O, S or NR
10
; R
1
is hydrogen, halogen, optionally substituted C
1-6
alkyl, optionally substituted C
2-6
alkenyl, optionally substituted C
2-6
alkynyl, optionally substituted C
1-6
alkoxy, optionally substituted C
1-6
alkylthio, optionally substituted C
3-7
cycloalkyl, cyano, nitro or SF
5
; R
2
is hydrogen, halogen, optionally substituted C
1-6
alkyl, optionally substituted C
2-6
alkenyl, optionally substituted C
1-6
alkynyl, optionally substituted C
1-6
alkoxy, optionally substituted C
1-6
alkylthio, optionally substituted C
1-6
alkylsulfinyl, optionally substituted C
1-6
alkylsulfonyl, cyano, nitro, formyl, optionally substituted C
1-6
alkylcarbonyl, optionally substituted C
1-6
alkoxycarbonyl, SF
5
or R
11
ON═C(R
12
); or R
1
and R
2
together with the atoms to which they are attached may be joined to form a five, six or seven-membered saturated or unsaturated, carbocylic or heterocyclic ring which may contain one or two heteroatoms selected from O, N or S and which is optionally substituted by C
1-6
alkyl, C
1-6
haloalkyl or halogen; R
3
is hydrogen, optionally substituted C
1-10
alkyl, optionally substituted [C
2-6
alkenyl(C
1-6
)alkyl], optionally substituted [C
2-6
alkynyl(C
1-6
)alkyl], optionally substituted C
3-7
cycloalkyl, optionally substituted C
1-10
alkylcarbonyl, optionally substituted C
1-10
alkoxycarbonyl, formyl, optionally substituted C
1-10
alkylaminocarbonyl, optionally substituted di(C
1-10
)alkylaminocarbonyl, optionally substituted phenoxycarbonyl, optionally substituted C
1-6
alkylthio, optionally substituted C
1-6
alkylsulfinyl, optionally substituted C
1-6
alkylsulfonyl, optionally substituted C
1-6
arylthio, optionally substituted C
1-6
arylsulfinyl, optionally substituted C
1-6
arylsulfonyl or R
13
R
14
NS(O)
p
; p is 0, 1 or 2; R
4
, R
5
and R
6
are, independently, hydrogen, halogen, optionally substituted C
1-6
alkyl, optionally substituted C
1-6
alkoxy, optionally substituted C
1-6
alkylthio, optionally substituted C
1-6
alkylsulfinyl, optionally substituted C
1-6
alkylsulfonyl, cyano, nitro, optionally substituted C
1-6
alkylcarbonyl, optionally substituted C
1-6
alkoxycarbonyl or SF
5
; R
7
is hydrogen, halogen, cyano, optionally substituted C
1-20
alkyl, optionally substituted C
2-20
alkenyl, optionally substituted C
2-20
alkynyl, optionally substituted C
3-7
cycloalkyl, optionally substituted C
5-6
cycloalkenyl, formyl, optionally substituted C
1-20
alkoxycarbonyl, optionally substituted C
1-20
alkylcarbonyl, aminocarbonyl, optionally substituted C
1-20
alkylaminocarbonyl, optionally substituted di(C
1-20
)alkylaminocarbonyl, optionally substituted aryloxycarbonyl, optionally substituted arylcarbonyl, optionally substituted arylaminocarbonyl optionally substituted N—(C
1-6
)alkyl-N-arylaminocarbonyl, optionally substituted diarylaminocarbonyl, optionally substituted heteroaryloxycarbonyl, optionally substituted heteroarylcarbonyl, optionally substituted heteroarylaminocarbonyl, optionally substituted N—(C
1-6
)alkyl-N-heteroarylaminocarbonyl, optionally substituted diheteroarylaminocarbonyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, SH, optionally substituted C
1-20
alkylthio, optionally substituted C
1-20
alkylsulfinyl, optionally substituted C
1-20
alkylsulfonyl, optionally substituted arylthio, optionally substituted arylsulfinyl, optionally substituted arylsulfonyl, R
15
O, R
16
R
17
N or R
18
ON═C(R
19
); R
8
is hydrogen, halogen, nitro, cyano, optionally substituted C
1-8
alkyl, optionally substituted C
2-6
alkenyl, optionally substituted C
2-6
alkynyl, optionally substituted C
3-7
cycloalkyl, optionally substituted C
1-6
alkoxycarbonyl, optionally substituted C
1-6
alkylcarbonyl, optionally substituted C
1-6
alkylaminocarbonyl, optionally substituted di(C
1-6
)alkylaminocarbonyl, optionally substituted phenyl or optionally substituted heteroaryl; R
9
is hydrogen, cyano, nitro, optionally substituted C
1-6
alkyl, optionally substituted C
3-7
cycloalkyl, optionally substituted (C
2-4
)alkenyl(C
1-6
)alkyl, optionally substituted (C
2-6
)alkynyl(C
1-6
)alkyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted C
1-6
alkylcarbonyl, optionally substituted C
1-6
alkoxycarbonyl, optionally substituted C
1-6
alkylamino, optionally substituted di(C
1-6
)alkylamino, optionally substituted C
1-6
alkylcarbonylamino, optionally substituted C
1-6
alkoxycarbonylamino, optionally substituted C
1-6
alkoxy, optionally substituted C
1-6
alkylthio, optionally substituted C
1-6
alkylsulfinyl, optionally substituted C
1-6
alkylsulfonyl, optionally substituted arylthio, optionally substituted arylsulfinyl, optionally substituted arylsulfonyl or C
1-6
alkylcarbonyloxy; R
10
is hydrogen, cyano, optionally substituted C
1-8
alkyl, optionally substituted [C
2-6
alkenyl(C
1-6
)alkyl], optionally substituted [C
2-6
alkyl(C
1-6
)alkyl], optionally substituted C
3-7
cycloalkyl, optionally substituted [C
3-7
cycloalkyl(C
1-6
)alkyl], C
1-6
alkoxy(C
1-6
)alkyl, optionally substituted C
1-6
alkoxycarbonyl, optionally substituted C
1-6
alkylcarbonyl, optionally substituted C
1-6
alkylaminocarbonyl, optionally substituted di(C
1-6
)alkylaminocarbonyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted alkylsulfonyl or optionally substituted arylsulfonyl; R
11
and R
18
are, independently, hydrogen, optionally substituted phenyl (C
1-2
)alkyl or optionally substituted C
1-20
alkyl; R
12
and R
19
are, independently, hydrogen, optionally substituted phenyl or optionally substituted C
1-6
alkyl; R
13
and R
14
are, independently, optionally substituted C
1-6
alkyl; or R
13
and R
14
together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N and S and which is optionally substituted by one or two independently selected C
1-6
alkyl groups; R
15
is hydrogen, optionally substituted C
1-20
alkyl, optionally substituted [C
2-20
alkenyl(C
1-6
)alkyl], optionally substituted [C
2-20
alkynyl(C
1-6
)alkyl], optionally substituted C
3-7
cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, (C
1-6
)alkylCH═N, optionally substituted arylCH═N, optionally substituted [aryl(C
1-6
)alkyl]CH═N, optionally substituted heteroarylCH═N, optionally substituted [hetero

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