Plant protecting and regulating compositions – Plant growth regulating compositions – Plural active ingredients
Utility Patent
1998-03-23
2001-01-02
Dees, Jose′ G. (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Plural active ingredients
C504S130000, C504S131000, C504S132000, C504S138000, C504S140000, C514S222200, C514S228200, C514S297000, C514S272000
Utility Patent
active
06169056
ABSTRACT:
The present invention relates to compositions for controlling harmful fungi and to methods of controlling harmful fungi using such compositions.
It is known from the literature that active ingredients which inhibit the cytochrome bc
1
complex (cytochrome complex III) can be employed as fungicides [cf. U. Brandt, U. Haase, H. Sch{umlaut over (a)}gger, G. von Jagow: “Spezifit{umlaut over (a)}t and Wirkmechanismus der Strobilurine” [Specificity and mechanism of action of the strobilurins], Dechema monograph Vol. 129, 27-38, VCH Verlagsgesellschaft Weinheim, 1993; J. M. Clough: Natural Product Reports, 1993, 565-574; F. Röhl, H. Sauter: Biochem. Soc. Trans. 22, 635 (1993)].
However, when using these active ingredients, it has emerged that their action is only transitory, ie. new fungal growth was observed after only a short time.
EP-A-545 099 describes anilide compounds of the formula
where A is phenyl which is substituted in the 2-position by methyl, trifluoromethyl, chlorine, bromine or iodine, or is one of certain aromatic or non-aromatic heterocyclic radicals which can be unsubstituted or substituted by methyl, chlorine or trifluoromethyl, and R is one of certain aliphatic or cycloaliphatic radicals which can be unsubstituted or substituted by halogen, or is phenyl which is unsubstituted or substituted by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio or halogen. These compounds can be used for controlling botrytis.
EP-A-589 301 describes anilide compounds of the same formula where A is a cyclic radical of the formulae:
where R
1
is hydrogen or C
1
-C
4
-alkyl; R
2
is halogen or C
1
-C
4
-alkyl;
R
3
is C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl; n is 1 or 2; and R has essentially the abovementioned meanings. These compounds can also be used for treating botrytis.
WO 93/11117 describes compounds of the formula
where
Q is C
1
-C
3
-alkyl, C
2
-C
3
-alkenyl, C
2
-C
3
-alkynyl, —(CH
2
)
m
CH═or —(CH
2
)
m
—X—CH
2
)m;
n is 0 or 1;
each m independently of the other is 0, 1, 2 or 3;
each X independently is O or S;
R
1
is one of certain alicyclic radicals;
R
2
is hydrogen, fluorinated methyl, methyl, ethyl, C
2
-C
6
-alkenyl, C
3
-C
6
-chloroalkyl, phenyl, alkylthioalkyl, alkoxyalkyl, haloalkylthioalkyl, haloalkoxyalkyl or hydroxyalkyl;
R
3
is halomethyl, halomethoxy, methyl, ethyl, halogen, cyano, methylthio, nitro, aminocarbonyl or aminocarbonylmethyl;
R
4
is hydrogen, halogen or methyl;
R
5
, R
6
and R
7
in each case independently of one another are selected from amongst hydrogen, halogen, cyano, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
3
-C
4
-cycloalkyl and halomethoxy. These compounds are fungicidally active.
However, it has emerged that the abovementioned anilide compounds do not have a sufficiently broad and satisfactory spectrum of action.
It is an object of the present invention to provide an improved possibility of controlling harmful fungi, in particular botrytis.
Surprisingly, we have found that this object is achieved by a composition which comprises an active ingredient which inhibits respiration on cytochrome complex III in combination with an amide compound of the abovementioned type.
The present invention therefore relates to compositions for controlling harmful fungi which comprise, in a solid or liquid carrier,
a) at least one active ingredient I, which inhibits respiration on cytochrome complex III, and
b) at least one amide compound of the formula II
A—CO—NR
1
—R
2
(II)
where
A is an aryl group or an aromatic or non-aromatic 5- or 6-membered heterocycle which has 1 to 3 hereto atoms selected from amongst O, N and S;
it being possible for the aryl group or the heterocycle to be unsubstituted or to have 1, 2 or 3 substituents, independently of one another selected from amongst alkyl, halogen, CHF
2
, CF
3
, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl and alkylsulfonyl;
R
1
is a hydrogen atom, alkyl or alkoxy;
R
2
is a phenyl or cycloalkyl group which is unsubstituted or has 1 to 3 substituents, independently of one another selected from amongst phenyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkenyl, cycloalkyloxy and cycloalkenyloxy and which can additionally be substituted by 1 or more halogen atoms, it being possible for the aliphatic and cycloaliphatic radicals to be partially or fully halogenated and/or for the cycloaliphatic radicals to be substituted by 1 to 3 alkyl groups, and it being possible for the phenyl group, in turn, to have 1 to 5 halogen atoms and/or 1 to 3 substituents, independently of one another selected from amongst alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and haloalkylthio, and it being possible for the amidic phenyl group to be fused to a saturated 5-membered ring which is unsubstituted or substituted by one or more alkyl groups and/or can have one hereto atom selected from amongst O and S, with the exception of the compound of the formula II where
A is 2-chloropyridin-3-yl, R
1
is H and R
2
is
The compositions according to the invention have a synergistic action and are therefore especially suitable for controlling harmful fungi, in particular botrytis. It is assumed that this is based on the fact that, when respiration on the cytochrome complex III is inhibited, the fungus utilizes a secondary route of alternative respiration, so that the fungi are not destroyed completely. This would means that the amide compounds of the formula II inhibit the alternative respiration. It must therefore be assumed that the combination of the two active ingredients inhibits respiration via the cytochrome complex III and also the alternative respiration, so that the fungi are destroyed completely.
Halogen within the scope of the present invention is fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
The term “alkyl” encompasses straight-chain or branched alkyl groups. They are preferably straight-chain or branched C
1
-C
12
-alkyl and, in particular, C
1
-C
6
-alkyl groups. Examples of alkyl groups are alkyl such as, in particular, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl, 1-ethyl-2-methylpropyl, n-heptyl, 1-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 1-propylbutyl, octyl, decyl, dodecyl.
Haloalkyl is an alkyl group as defined above which is partially or fully halogenated with one or more halogen atoms, in particular fluorine and chlorine. There are preferably 1 to 3 halogen atoms present, the difluoromethyl or the trifluoromethyl group being especially preferred.
What has been said above the alkyl group and haloalkyl group applies analogously to the alkyl and haloalkyl group in alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, and alkylsulfonyl.
The alkenyl group encompasses straight-chain and branched alkenyl groups. Preferably, they are straight-chain or branched C
3
-C
12
-alkenyl groups, in particular C
3
-C
6
-alkenyl groups. Examples of alkenyl groups are 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-but
Ammermann Eberhard
Bayer Herbert
Eicken Karl
Kohle Harald
Lorenz Gisela
BASF - Aktiengesellschaft
Dees Jose′ G.
Keil & Weinkauf
Pryor Alton
LandOfFree
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