Fungicide mixtures

Details Fungicide mixtures Fungicide mixtures

1998-10-22

2001-04-03

Robinson, Allen J. (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

C514S063000, C514S255050, C514S269000, C514S383000, C514S399000, C514S508000, C514S538000, C514S618000, C514S619000

Reexamination Certificate

active

06211236

ABSTRACT:

The present invention relates to fungicidal mixtures which comprise
a) an oxime ether of the formula I
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 can 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;
and at least one compound from groups b)-c):
b.1) the oxime ether carboxylate of the formula IIa,
b.2) the oxime ether carboxamide of the formula IIb
b.3) the methoxyacrylate of the formula IIc,
and/or
c) an azole derivative III selected from the group of the compounds III.1 to III.17
1-[(2RS,4RS;2RS,4SR)-4-bromo-2-(2,4-dichlorophenyl)-tetrahydrofuryl]-1H-1,2,4-triazole (III.1)
2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (III.2)
(+)-4-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-2-yl]phenyl 4-chlorophenyl ether (III.3)
(E)-(R,S)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol (III.4)
(Z)-2-(1H-1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)oxirane (III.5)
4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazolyl-methyl)butyronitrile (III.6)
3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)-one (III.7)
bis(4-fluorophenyl) (methyl) (1H-1,2,4-triazol-1-ylmethyl)silane (III.8)
(R,S)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol (III.9)
(1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (III.10)
N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]imidazole-1-carboxamide (III.11)
(+)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (III.12)
(R,S)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (III.13)
(+)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazolyl)-propyl 1,1,2,2-tetrafluoroethyl ether (III.14)
(E)-1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-1H-imidazole (III.15)
(RS)-2,4′-difluoro-&agr;-(1H-1,2,4-triazol-1-ylmethyl)-benzhydryl alcohol (III.16)
2-p-chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)-hexanenitrile (III.17)
in a synergistically active amount.
Moreover, the invention relates to methods of controlling harmful fungi with mixtures of the compounds I, II and III and to the use the compounds I, II and III for the preparation of such mixtures.
The compounds I are described in the literature as fungicides and insecticides (DE Appl. No. 19 528 651.0, WO-A 95/21,153 and WO-A 95/21,154).
The compounds IIa (EP-A 253 213), IIb (EP-A 477 631) and the compound IIc (EP-A 382,375), their preparation and their activity against harmful fungi have also been disclosed.
The azole derivatives III, their preparation and their activity against harmful fungi are known to the expert from the literature:
III.1: common name: bromuconazole, Proc. Br. Crop Prot. Conf. Pests Dis., 5-6, 439 (1990);
III.2: common name: cyproconazole, U.S. Pat. No. 4,664,696;
III.3: common name: difenoconazole, GB-A 2,098,607;
III.4: common name: diniconazole, CAS RN [83657-24-3];
III.5: common name: (proposed): epoxiconazole, EP-A 196 038;
III.6: common name: fenbuconazole (proposed), EP-A 251 775;
III.7: common name: fluquinconazole, Proc. Br. Crop Prot. Conf. Pests Dis., 5-3, 411 (1992);
III.8: common name: flusilazole, Proc. Br. Crop Prot. Conf. Pests Dis., 1, 413 (1984);
III.9: common name: hexaconazole, CAS RN [79983-71-4];
III.10: common name: metconazole, Proc. Br. Crop Prot. Conf. Pests Dis., 5-4, 419 (1992);
III.11: common name: prochloraz, U.S. Pat. No. 3,991,071;
III.12: common name: propiconazole, GB-A 1,522,657;
III.13: common name: tebuconazole, U.S. Pat. No. 4,723,984;
III.14: common name: tetraconazole, Proc. Br. Crop Prot. Conf. Pests Dis., 1, 49 (1988);
III.15: common name: triflumizole, JP-A 79/119,462;
III.16: common name: flutriafol, CAS RN [76674-21-0];
III.17: common name: myclobutanil, CAS RN [88671-89-0].
It was 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 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 mixtures 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 simultaneously together or separately or by applying the compounds I and II or III in succession than when the individual compounds are used.
In particular, the general formula I represents oxime ethers in which X is oxygen and Y is CH or X is amino and Y is N.
Moreover, preferred compounds I are those where Z is oxygen.
Equally, preferred compounds I are those where R′ is alkyl or benzyl.
Especially preferred with a view to their use in the synergistic mixtures according to the invention are the compounds I compiled in the tables which follow:
TABLE B
No.
ZR′
I.1
O—CH
2
CH
2
CH
3
I.2
O—CH(CH
3
)
2
I.3
O—CH
2
CH
2
CH
2
CH
3
I.4
O—CH(CH
3
)CH
2
CH
3
I.5
O—CH
2
CH(CH
3
)
2
I.6
O—C(CH
3
)
3
I.7
S—C(CH
3
)
3
I.8
O—CH(CH
3
)CH
2
CH
2
CH
3
I.9
O—CH
2
C(CH
3
)
3
I.10
O—C(Cl)═CCl
2
I.11
O—CH
2
CH═CH—Cl (trans)
I.12
O—CH
2
—C(CH
3
)═CH
2
I.13
O—CH
2
—(cyclopropyl)
I.14
O—CH
2
—C
6
H
5
I.15
O—CH
2
—[4-F—C
6
H
4
]
I.16
O—CH
2
—CH
3
I.17
O—CH(CH
2
CH
3
)
2
In relation to the C═Y— or C═CH— or C═N double bonds, the compounds of the formulae I and II can be in the E or the Z configuration (in relation to the carboxylic acid function). Accordingly, they can be used in the mixture according to the invention in each case either in the form of the pure E or Z isomers or else in the form of 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 be in each case in the form of pure E or Z isomers or in the form of E/Z isomer mixtures. The compounds I can be used in the mixtures according to the invention as isomer mixtures or else as pure isomers. With a view to their use, compounds I which are particularly preferred are those where the terminal oxime ether group of the side chain is in the cis configuration (OCH
3
relative to ZR′).
Because of their basic character, the compounds I, II and III are capable of forming adducts or salts with inorganic or organic acids or with metal ions.
Examples of inorganic acids are hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid, sulfuric acid, phosphoric acid and nitric acid.
Suitable organic acids are, for example, formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals having from 1 to 20 carbon atoms), arylsulfonic acids or -disulfonic acids (aromatic radicals such as phenyl and naphthyl which have attached to them one or two sulfo groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals of from 1 to 20 carbon atoms), arylphosphonic acids or -diphosphonic acids (aromatic radicals such as phenyl and naphthyl which have attached to them one or two phosphoric acid radicals), it being possible for the alkyl or aryl radicals to have attached,

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