Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-10-31
2001-06-12
Robinson, Allen J. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S063000, C514S259500, C514S399000, C514S407000
Reexamination Certificate
active
06245792
ABSTRACT:
The present invention relates to fungicidal mixtures which comprise
a) a carbamate of the formula I
where T 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 when n is 2, and at least one compound from the groups consisting of b)-d):
b) oxire ethers of the formula II
where the substituents have the following meanings:
X is oxygen or amino (NH);
Y is CH or N;
Z is oxygen, sulfur, amino (NH) or C
1
-C
4
-alkylamino (N—C
1
-C
4
-alkyl);
R′ is C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
2
-C
6
-haloalkenyl, C
3
-C
6
-alkynyl, C
3
-C
6
-haloalkynyl, C
3
-C
6
-cycloalkylmethyl, or is benzyl which can be partially or fully halogenated and/or have attached to it 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;
c.1) the oxime ether carboxylate of the formula IIIa
c.2)the oxime ether carboxamide of the formula IIIb
c.3) the methoxyacrylate of the formula IIIc,
and/or
d) an azole derivative IV selected from the group of the compounds IV.1 to IV.17
1-[(2RS,4RS;2RS,4SR)-4-bromo-2-(2,4-dichlorophenyl)tetrahydrofuryl]-1H-1,2,4-triazole (IV.1)
2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol (IV.2)
(+)-4-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-2-yl)phenyl 4-chlorophenyl ether (IV.3)
(E)-(R,S)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol (IV.4)
(Z)-2-(1H-1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)oxirane (IV.5)
4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazolylmethyl)-butyronitrile (IV.6)
3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)-one (IV.7)
bis(4-fluorophenyl)(methyl)(1H-1,2,4-triazol-1-ylmethyl)-silane (IV.8)
(R,S)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-hexan-2-ol (IV.9)
(1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (IV.10)
N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]imidazol-1-carboxamide (IV.11)
(+)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl-methyl]-1H-1,2,4-triazole (IV.12)
(R,S)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (IV.13)
(+)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazolyl)propyl 1,1,2,2-tetrafluoroethyl ether (IV.14)
(E)-1-[1-[[4-chloro-2-(trifluoromethyl]phenyl]imino]-2-propoxyethyl]-1H-imidazol (IV.15)
(RS)-2,4′-difluoro-&agr;-(1H-1,2,4-triazol-1-ylmethyl)benzhydroyl [sic] alcohol (IV.16)
2-p-chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanonitrile (IV.17)
in a synergistically active amount.
Moreover, the invention relates to methods of controlling harmful fungi with mixtures of the compounds I, II, III and IV and to the use of the compounds I, II, III and IV for the preparation of such mixtures.
The compounds of the formula I, their preparation and their action against harmful fungi have been disclosed in the literature (WO-A 96/01,256 and WO-A 96/01,258).
The compounds II are described in the literature as fungicides and insecticides (German Application No. 19 528 651.0).
The compounds IIIa (EP-A 253 213), IIIb (EP-A 477 631) and the compound IIIc (EP-A 382 375), their preparation and their action against harmful fungi have also been disclosed.
The azole derivatives IV, their preparation and their action against harmful fungi are known to the expert from the literature:
IV.1: common name: bromuconazole, Proc. Br. Crop Prot. Conf.—Pests Dis., 5-6, 439 (1990);
IV.2: common name: cyproconazole, U.S. Pat. No. 4,664,696;
IV.3: common name: difenoconazole, GB-A 2,098,607;
IV.4: common name: diniconazole, CAS RN [83657-24-3];
IV.5: common name (proposed): epoxiconazole, EP-A 196 038;
IV.6: common name: fenbuconazole (proposed), EP-A 251 775;
IV.7: common name: fluquinconazole, Proc. Br. Crop Prot. Conf.—Pests Dis., 5-3, 411 (1992);
IV.8: common name: flusilazole, Proc. Br. Crop Prot. Conf.—Pests Dis., 1, 413 (1984);
IV.9: common name: hexaconazole, CAS RN [79983-71-4];
IV.10: common name: metconazole, Proc. Br. Crop Prot. Conf.—Pests Dis., 5-4, 419 (1992);
IV.11: common name: prochloraz, U.S. Pat. No. 3,991,071;
IV.12: common name: propiconazole, GB-A 1,522,657;
IV.13: common name: tebuconazole, U.S. Pat. No. 4,723,984;
IV.14: common name: tetraconazole, Proc. Br. Crop Prot. Conf.—Pests Dis., 1, 49 (1988);
IV.15: common name: triflumizole, JP-A 79/119,462
IV.16: common name: flutriafol, CAS RN [76674-21-0]
IV.17: common name: myclobutanil, CAS RN [88671-89-0].
It was an object of the present invention to provide mixtures which display an improved activity against harmful fungi combined with a reduced total amount of active ingredients applied (synergistic mixtures) with a view to reducing the rates of application and to improving the spectrum of action of the known compounds.
Accordingly, we have found that this object is achieved by the mixture defined at the outset. Moreover, we have found that better control of the harmful fungi is possible by applying the compounds I and II or III or IV simultaneously together or separately or by applying the compounds I and II or III or IV in succession than when the individual compounds are used.
In particular, the formula I represents carbamates in which the combination of the substituents corresponds to one line of the table which follows:
TABLE 1
No.
T
R
n
I.1
N
2-F
I.2
N
3-F
I.3
N
4-F
I.4
N
2-Cl
I.5
N
3-Cl
I.6
N
4-Cl
I.7
N
2-Br
I.8
N
3-Br
I.9
N
4-Br
I.10
N
2-CH
3
I.11
N
3-CH
3
I.12
N
4-CH
3
I.13
N
2-CH
2
CH
3
I.14
N
3-CH
2
CH
3
I.15
N
4-CH
2
CH
3
I.16
N
2-CH(CH
3
)
2
I.17
N
3-CH(CH
3
)
2
I.18
N
4-CH(CH
3
)
2
I.19
N
2-CF
3
I.20
N
3-CF
3
I.21
N
4-CF
3
I.22
N
2,4-F
2
I.23
N
2,4-Cl
2
I.24
N
3,4-Cl
2
I.25
N
2-Cl, 4-CH
3
I.26
N
3-Cl, 4-CH
3
I.27
CH
2-F
I.28
CH
3-F
I.29
CH
4-F
I.30
CH
2-Cl
I.31
CH
3-Cl
I.32
CH
4-Cl
I.33
CH
2-Br
I.34
CH
3-Br
I.35
CH
4-Br
I.36
CH
2-CH
3
I.37
CH
3-CH
3
I.38
CH
4-CH
3
I.39
CH
2-CH
2
CH
3
I.40
CH
3-CH
2
CH
3
I.41
CH
4-CH
2
CH
3
I.42
CH
2-CH(CH
3
)
2
I.43
CH
3-CH(CH
3
)
2
I.44
CH
4-CH(CH
3
)
2
I.45
CH
2-CF
3
I.46
CH
3-CF
3
I.47
CH
4-CF
3
I.48
CH
2,4-F
2
I.49
CH
2,4-Cl
2
I.50
CH
3,4-Cl
2
I.51
CH
2-Cl, 4-CH
3
I.52
CH
3-Cl, 4-CH
3
The compounds I.12, I.23, I.32 and I.38 are especially preferred.
The general formula II particularly represents oxime ethers where X is oxygen and Y is CH or X is amino and Y is N.
Compounds II which are furthermore preferred are those where Z is oxygen.
Compounds II which are equally preferred are those where R′ is alkyl and benzyl.
Compounds II which are particularly preferred with a view to their use in the synergistic mixtures according to the invention are those compiled in the tables which follow:
TABLE B
No.
ZR′
II.1
O—CH
2
CH
2
CH
3
II.2
O—CH(CH
3
)
2
II.3
O—CH
2
CH
2
CH
2
CH
3
II.4
O—CH(CH
3
)CH
2
CH
3
II.5
O—CH
2
CH(CH
3
)
2
II.6
O—C(CH
3
)
3
II.7
S—C(CH
3
)
3
II.8
O—CH(CH
3
)CH
2
CH
2
CH
3
II.9
O—CH
2
C(CH
3
)
3
II.10
O—C(Cl)═CCl
2
II.11
O—CH
2
CH═CH—Cl (trans)
II.12
O—CH
2
—C(CH
3
)═CH
2
II.13
O—CH
2
—(cyclopropyl)
II.14
O—CH
2
—C
6
H
5
II.15
O—CH
2
-[4-F—C
6
H
4
]
Relative to the C═Y or C═CH or C═N double bonds, the compounds of the formulae I, II and III can exist in the E or in the Z configuration (relative to the carboxylic acid function). Accordingly, they can be used in the mixture according to the invention in each case as pure E or Z isomers or as an E/Z isomer mixture. The E/Z isomer mixture or the Z isomer are preferably used, the Z isomer being especially preferred.
The C═N double bonds of the oxime ether groups in the side chain of the compounds I can exist in each case as the pure E or Z isomers or as E/Z isomer mixtures. The compounds I can be used in the mixtures according to the invention both as isomer mixtures and as pure isomers. Preferred with a view to their use are, in particular, compounds of the formula
Ammermann Eberhard
Leyendecker Joachim
Lorenz Gisela
Muller Bernd
Saur Reinhold
BASF - Aktiengesellschaft
Keil & Weinkauf
Robinson Allen J.
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