Fungicidal mixtures

Details Fungicidal mixtures Fungicidal mixtures

1999-12-01

2001-10-16

Robinson, Allen J. (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S239500, C514S317000, C514S384000, C514S269000, C514S407000, C514S522000, C514S539000, C514S543000, C514S619000

Reexamination Certificate

active

06303599

ABSTRACT:

The present invention relates to a fungicidal mixture which comprises
a.1) a carbamate of the formula I.a,
in which X is CH or N, n is 0, 1 or 2 and R is halogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl, it being possible for the radicals R to be different if n is 2, or
a.2)the oxime ether carboxamide of the formula I.b
 and
b.1) 4-[2-methyl-3-(4-tert-butylphenyl)propyl]-2,6-dimethylmorpholine
 or
b.2) 4-(C
10
-C
13
-alkyl)-2,6-dimethylmorpholine
 or
b.3) (RS)-1-[3-(4-tert-butylphenyl)-2-methylpropyl]-piperidine
 and
c) a further active ingredient from the class of the strobilurin fungicides (III),
in a synergistically effective amount.
Particular preference is given to mixtures which comprise, as strobilurin fungicide (III), a
III.1 methyl phenylacetate of the formula III.1
in which U is CHOCH
3
or NOCH
3
, R
a
is cyano, halogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl, x is 1, 2 or 3, it being possible for the radicals R
a
to be different if x is 2 or 3, and Y is one of the radicals OCH
2
or O-(4,6-pyrimidinyl)-O, or a
III.1 benzyloxybisoxime of the formula III.2
 where:
A is OCH
3
or NHCH
3
;
B is CHOCH
3
or NOCH
3
;
R′ is phenyl which may carry one to three of the following substituents: cyano, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy and C
1
-C
4
-alkylthio; or C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, C
1
-C
6
-haloalkyloxy, C
1
-C
6
-haloalkylthio, C
1
-C
6
-haloalkylamino, N—C
1
-C
6
-haloalkyl-N—C
1
-C
4
-alkylamino, C
3-C
6
-alkenyloxy, C
3
-C
6
-alkenylthio, C
3
-C
6
-alkenylamino, N—C
3
-C
6
-alkenyl-N—C
1
-C
4
-alkylamino, C
2
-C
6
-haloalkenyloxy, C
2
-C
6
-haloalkenylthio, C
2
-C
6
-haloalkenylamino, N—C
2
-C
6
-haloalkenyl-N—C
1
-C
4
-alkylamino, C
3
-C
6
-alkynyloxy, C
3
-C
6
-alkynylthio, C
3
-C
6
-alkynylamino, N—C
3
-C
6
-alkynyl-N—C
1
-C
4
-alkylamino, C
3
-C
6
-haloalkynyloxy, C
3
-C
6
-haloalkynylthio, C
3
-C
6
-haloalkynylamino, N—C
3
-C
6
-haloalkynyl-N—C
1
-C
4
-alkylamino, C
3
-C
6
-cycloalkyl-methoxy, C
3
-C
6
-cycloalkyl-methylthio, C
3
-C
6
-cycloalkyl-methylamino, N—C
3
-C
6
-cycloalkyl-methyl-N—C
1
-C
4
-alkylamino, or benzyloxy, benzylthio, benzylamino, N-benzyl-N—C
1
-C
4
-alkylamino, it being possible for the phenyl groups to be partially or fully halogenated and/or to carry one to three of the following radicals: cyano, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy and C
1
-C
4
-alkylthio.
Moreover, the invention relates to methods for controlling harmful fungi using mixtures of the compounds I (I.a and I.b), II (II.a to II.c) and III (III.1 and III.2).
The compounds of the formula I, their preparation and their activity against harmful fungi are disclosed in the literature (EP-A 477 631; WO-A 96/01,256; WO-A 96/01,258).
The compounds of the formula II are also disclosed:
II.a (common name: fenpropimorph): CAS RN [67564-91-4], U.S. Pat. No. 4,202,894;
II.b (common name: tridemorph): CAS RN [81412-43-3], DE-A 11 64 152;
II.c (common name: fenpropidin): CAS RN [67306-00-7], U.S. Pat. No. 4,202,894.
Furthermore, the strobilurin fungicides III are disclosed in the literature as active compounds for controlling harmful fungi:
oxime ether ester III.1: EP-A 253 213, EP-A 254 426 and EP-A 382 375;
benzyloxybisoximes of the formula III.2: WO-A 95/18,789, WO-A 95/21,153, WO-A 95/21,154 and DE P 195 28 651.0.
Synergistic mixtures of the compounds I.a with active compounds II.a to II.c are disclosed in the earlier application DE-A 19 616 724.
Furthermore, EP-A 645 087 discloses synergistic mixtures of the compound I.b with active compounds II.a to II.c.
It is an object of the present invention to provide mixtures which have an improved activity against harmful fungi combined with a reduced total amount of active ingredient applied (synergistic mixtures), with a view to reducing the application rates and to improving the activity spectrum of the known compounds I, II and III.
We have found that this object is achieved by the mixture defined at the outset. Moreover, we have found that better control of harmful fungi is possible by applying the compounds I, II and III simultaneously, that is either together or separately, or by applying the compounds I, II and III in succession than when the individual compounds are used.
The formula I.a in particular represents carbamates in which the combination of the substituents corresponds to a row of Table 1 below:
TABLE 1
I.a

No.
X
R
n
Ia.1
N
2-F
Ia.2
N
3-F
Ia.3
N
4-F
Ia.4
N
2-Cl
Ia.5
N
3-Cl
Ia.6
N
4-Cl
Ia.7
N
2-Br
Ia.8
N
3-Br
Ia.9
N
4-Br
Ia.10
N
2-CH
3
Ia.11
N
3-CH
3
Ia.12
N
4-CH
3
Ia.13
N
2-CH
2
CH
3
Ia.14
N
3-CH
2
CH
3
Ia.15
N
4-CH
2
CH
3
Ia.16
N
2-CH(CH
3
)
2
Ia.17
N
3-CH(CH
3
)
2
Ia.18
N
4-CH(CH
3
)
2
Ia.19
N
2-CF
3
Ia.20
N
3-CF
3
Ia.21
N
4-CF
3
Ia.22
N
2,4-F
2
Ia.23
N
2,4-Cl
2
Ia.24
N
3,4-Cl
2
Ia.25
N
2-Cl, 4-CH
3
Ia.26
N
3-Cl, 4-CH
3
Ia.27
CH
2-F
Ia.28
CH
3-F
Ia.29
CH
4-F
Ia.30
CH
2-Cl
Ia.31
CH
3-Cl
Ia.32
CH
4-Cl
Ia.33
CH
2-Br
Ia.34
CH
3-Br
Ia.35
CH
4-Br
Ia.36
CH
2-CH
3
Ia.37
CH
3-CH
3
Ia.38
CH
4-CH
3
Ia.39
CH
2-CH
2
CH
3
Ia.40
CH
3-CH
2
CH
3
Ia.41
CH
4-CH
2
CH
3
Ia.42
CH
2-CH(CH
3
)
2
Ia.43
CH
3-CH(CH
3
)
2
Ia.44
CH
4-CH(CH
3
)
2
Ia.45
CH
2-CF
3
Ia.46
CH
3-CF
3
Ia.47
CH
4-CF
3
Ia.48
CH
2,4-F
2
Ia.49
CH
2,4-Cl
2
Ia.50
CH
3,4-Cl
2
Ia.51
CH
2-Cl, 4-CH
3
Ia.52
CH
3-Cl, 4-CH
3
Particular preference is given to the compounds Ia.12, Ia.23, Ia.32 and Ia.38.
The formula III.1 in particular represents methyl phenylacetates in which the combination of the substituents corresponds to a row of Table 2 below:
TABLE 2
III.1

No.
U
Y
R
a
x
III-1.1
NOCH
3
OCH
2
2-CH
3
III-1.2
NOCH
3
OCH
2
2,5-(CH
3
)
2
III-1.3
NOCH
3
OCH
2
2-Cl
III-1.4
NOCH
3
OCH
2
2-Cl, 5-CH
3
III-1.5
NOCH
3
OCH
2
5-Cl, 2-CH
3
III-1.6
CHOCH
3
O-[4,6-pyrimi-
2-CN
dinediyl]-O
III-1.7
CHOCH
3
O-(4,6-pyrimi-
3-CN
dinediyl]-O
III-1.8
CHOCH
3
O-(4,6-pyrimi-
4-CN
dinediyl]-O
Particular preference is given to the compounds III-1.1 and III-1.6.
The formula III.2 in particular represents benzyloxybisoximes in which the combination of the substituents corresponds to one row of Table 3 below:
No.
A
B
R′
III-2.1
NHCH
3
NOCH
3
C
6
H
5
III-2.2
NHCH
3
NOCH
3
4-F—C
6
H
4
III-2.3
NHCH
3
NOCH
3
4-Cl—C
6
H
4
III-2.4
NHCH
3
NOCH
3
4-Br—C
6
H
4
III-2.5
NHCH
3
NOCH
3
4-I—C
6
H
4
III-2.6
NHCH
3
NOCH
3
O-CH
2
CH
2
CH
3
III-2.7
NHCH
3
NOCH
3
O-CH(CH
3
)
2
III-2.8
NHCH
3
NOCH
3
O-CH
2
CH
2
CH
2
CH
3
III-2.9
NHCH
3
NOCH
3
O-CH(CH
3
)CH
2
CH
3
III-2.10
NHCH
3
NOCH
3
O-CH
2
CH(CH
3
)
2
III-2.11
NHCH
3
NOCH
3
O—C(CH
3
)
3
III-2.12
NHCH
3
NOCH
3
S—C(CH
3
)
3
III-2.13
NHCH
3
NOCH
3
O-CH(CH
3
)CH
2
CH
2
CH
3
III-2.14
NHCH
3
NOCH
3
O-CH
2
C(CH
3
)
3
III-2.15
NHCH
3
NOCH
3
O-CH
2
C(Cl)═CCl
2
III-2.16
NHCH
3
NOCH
3
O-CH
2
CH═CH-Cl (trans)
III-2.17
NHCH
3
NOCH
3
O-CH
2
-C(CH
3
)═CH
2
III-2.18
NHCH
3
NOCH
3
O-CH
2
-(cyclopropyl)
III-2.19
NHCH
3
NOCH
3
O-CH
2
-C
6
H
5
III-2.20
NHCH
3
NOCH
3
O-CH
2
-[4-F—C
6
H
4
]
III-2.21
NHCH
3
NOCH
3
O-CH
2
CH
3
III-2.22
NHCH
3
NOCH
3
O-CH(CH
2
CH
3
)
2
III-2.23
OCH
3
CHOCH
3
O-CH
2
CH
2
CH
3
III-2.24
OCH
3
CHOCH
3
O-CH(CH
3
)
2
III-2.25
OCH
3
CHOCH
3
O-CH
2
CH
2
CH
2
CH
3
III-2.26
OCH
3
CHOCH
3
O-CH(CH
3
)CH
2
CH
3
III-2.27
OCH
3
CHOCH
3
O-CH
2
CH(CH
3
)
2
III-2.28
OCH
3
CHOCH
3
O—C(CH
3
)
3
III-2.29
OCH
3
CHOCH
3
S—C(CH
3
)
3
III-2.30
OCH
3
CHOCH
3
O-CH(CH
3
)CH
2
CH
2
CH
3
III-2.31
OCH
3
CHOCH
3
O-CH
2
C(CH
3
)
3
III-2.32
OCH
3
CHOCH
3
O-CH
2
C(Cl)═CCl
2
III-2.33
OCH
3
CHOCH
3
O-CH
2
CH═CH-Cl (trans)
III-2.34
OCH
3
CHOCH
3
O-CH
2
-C(CH
3
)═CH
2
III-2.35
OCH
3
CHOCH
3
O-CH
2
-(cyclopropyl)
III-2.36
OCH
3
CHOCH
3
O-CH
2
-C
6
H
5
III-2.37
OCH
3
CHOCH
3
O-CH
2
-[4-F—C
6
H
4
]
III-2.38
OCH
3
CHOCH
3
O-CH
2
CH
3
III-2.39
OCH
3
CHOCH
3
O-CH(CH
2
CH
3
)
2
Particular preference is given to compounds III-2.1, III-2.2, III-2.3 and to those compounds III-2 in which R′ is C
1
-C
6
-alkoxy or is benzyloxy with or without substitution by halogen.
Owing to the basic character of

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