Fungicidal active substance combinations

Details Fungicidal active substance combinations Fungicidal active substance combinations

2001-05-16

2003-05-06

Pak, John (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Silicon containing doai

C514S259500, C514S260100, C514S269000, C514S270000, C514S383000, C514S384000

Reexamination Certificate

active

06559136

ABSTRACT:

This application is a 371 of PCT/EP99/08558, filed on Nov. 8, 1999.
The present application relates to novel active compound combinations comprising, on the one hand, pyrimidine derivatives and, on the other hand, other known fungicidally active compounds and being highly suitable for controlling phytopathogenic fungi.
It is already known that pyrimidine derivatives have fungicidal properties (cf. DE-A-19 646 407). The activity of this substance is good; however, at low application rates it sometimes leaves something to be desired.
Furthermore, it is already known that numerous azole derivatives, aromatic carboxylic acid derivatives. morpholine compounds and other heterocycles can be used for controlling fungi (cf. K. H. Büichel “Pflanzenschutz und Schädlings-bekämpfung” pages 87, 136, 140, 141 and 146 to 153, Georg Thieme Verlag, Stuttgart 1977). However, the activity of the substances in question is not always satisfactory at low application rates.
It has now been found that the novel active compound combinations of compounds of the general formula (I)
in which
Z represents optionally substituted phenyl,
X represents halogen and
A represents heterocyclyl —COOCH
3
or —CO—NH—CH
3
and
in each case one compound selected from the list of the compounds below
1)
spiroxamin
2)
quinoxyfen (DE 795)
3)
tebuconazole
4)
fenpropidin
5)
fenpropimorph
6)
(R,S)- and (R,R)- and (S,R)- and (S,S)-N-(1-cyano-1,2-
dimethylpropyl)-2-(2,4-dichlorophenoxy)propionamide
7)
chlorothalonil (DAC 2787)
8)
triadimefon
9)
triadimenol
10)
epoxiconazole
11)
metconazole
12)
fluquinconazole
13)
cyproconazole
14)
penconazole
15)
kresoximmethyl
16)
azoxystrobin
17)
cyprodinil
18)
iminoctadiene triacetate (Befran)
19)
flusilazole (Harvesan)
20)
prochloraz (Sportak)
21)
propiconazole (Desmel)
22)
bitertanol (KWG 0599)
23)
imidacloprid (NTN 33893)
24)
dichlofluanid (Euparen)
25)
tolylfluanid (Euparen M)
26)
metalaxyl (Ridomil)
27)
fenpiclonil
28)
difenoconazole
29)
fludioxonil
30)
carbendazim, benomyl
31)
fuberidazol
32)
imazalil
33)
triazoxide (SAS 9244)
34)
cyfluthrin (Pyrethroid)
35)
guazatine
36)
acibenzolar-S-methyl (Bion)
37)
pencycuron (Monceren)
38)
flutolanil (Moncut)
39)
tricyclazole (Beam)
40)
propineb (Antracol)
41)
procymidone (Sumisclex)
42)
mancozeb
43)
folpet (Phaltan)
44)
dimetomorph
45)
cymoxanil (Curzate)
46)
fosetyl-Al (Aliette)
47)
famoxadone
48)
pyrimethanil
49)
mepanipyrim
50)
iprovalicarb
51)
fenhexamid
52)
carpropamid
53)
fluazinam
54)
captan
55)
chinomethionat (Morestan)
56)
fenamidone (RP 7213)
57)
clothianidin
58)
thiacloprid
59)
diacloden
60)
acetamiprid
61)
MTI 334
62)
sulphur
63)
copper
64)
rovral
65)
ronilan
66)
rabcide
67)
hinosan
68)
coratop
69)
2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-
1,2,4-triazol-1-yl)-propan-2-ol
70)
1-(3,5-dimethylisoxazol-4-sulfonyl)-2-chloro-6,6-difluoro-
[1,3]-dioxolo-[4,5f]-benzimidazole
71)
3-{1-[4-(<2-chlorophenoxy>5-fluoropyrimid-6-yloxy)-phenyl]-
1-(methoximino)-methyl}-5,6-dihydro-1,4,2-dioxazine
72)
zoxamide
73)
cyamidazosulfamide
74)
silthiopham
75)
trifloxystrobin
76)
N-methyl-2-(methoxyimino)-2-[2-([1-(3-trifluoromethyl-
phenyl)ethoxy]iminomethyl)-phenyl]acetamide
77)
2-[2-([2-phenyl-2-methoxy-imino-1-methylethyl]imino-
oxymethyl)phenyl]-2-methoxy-imino-N-methylacetamide
78)
2-[2-([2-(4-fluorophenyl)-2-methoxyimino-1-methylethyl]-
iminooxymethyl)phenyl]-2-methoxyimino-N-methyl-acetamide
79)
2-[4-methoxy-3-(1-methyl-ethoxy)-1,4-diazabuta-1,3-
dienyloxymethyl)phenyl-2-methoximino-N-methylacetamide
80)
methyl N-(2-[1-(4-chloro-phenyl)pyrazol-3-yloxymethyl]-
phenyl)-N-methoxycarbamate
81)
2,4-dihydro-5-methoxy-2-methyl-4-[2-([([1-(3-trifluoro-
methylphenyl)ethylidene]-amino)oxy]methyl)phenyl)-3H-
1,2,4-triazol-3-one
82)
picoxystrobin
in a mixing ratio of a compound of the formula (I) to in each case one compound of the formulae 1) to 82) of from 20:1 to 1:50 parts by weight have very good fungicidal properties.
Surprisingly, the fungicidally activity of the active compound combination according to the invention is considerably higher than the sum of the activities of the individual active compounds. An unforeseeable true synergistic effect is present, and not just an addition of activities.
Compounds of the formula (I), in which
Z represents a group
in which
R
1
and R
2
represent, independently of one another, hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, bromine, fluorine or cyano,
X represents fluorine and
A represents —CO—NH—CH
3
,
may be preferably mentioned.
In particular, the compounds of the formula (I), in which
R
1
represents hydrogen and
R
2
represents methyl, ethyl, methoxy, chlorine, bromine, fluorine or cyano,
and compounds of the formula (I), in which
R
1
represents methyl and
R
2
represents hydrogen, methyl, ethyl, methoxy, chlorine, bromine, fluorine or cyano,
and compounds of the formula (1), in which
R
2
represents methyl and
R
1
represents hydrogen, methyl, ethyl, methoxy, chlorine, bromine, fluorine or cyano,
may be mentioned specifically.
The active compounds of the formula (I) are known (cf., for example, DE-A 19 646 407, WO 97-27189 or GB 225 3624).
The active compounds which are furthermore present in the combinations according to the invention are also known. The active compounds are described, for example, in The Pesticide Manual, 11th Edition, British Crop Protection Council (BCPC).
The active compound combinations according to the invention comprise, in addition to at least one active compound of the formula (I), at least one active compound from among the compounds of groups 1) to 82). Additionally, they may also comprise other fungicidally active additives.
If the active compounds in the active compound combinations according to the invention are present in certain weight ratios, the synergistic effect is particularly pronounced. However, the weight ratios of the active compounds in the active compound combinations can be varied within a relatively wide range. In general, the combinations according to the invention comprise the active compound of the formula (I) and the mixing partner in the preferred and particularly preferred mixing ratios given in the table below:
Particularly
Preferred
preferred
Mixing partner
mixing ratio*
mixing ratio*
spiroxamin
10:1 to 1:20
 5:1 to 1:10
quinoxyfen (DE 795)
10:1 to 1:20
 5:1 to 1:10
tebuconazole
10:1 to 1:10
 5:1 to 1:5
fenpropidin
10:1 to 1:20
 5:1 to 1:10
fenpropimorph
10:1 to 1:20
 5:1 to 1:10
(R,S)- and (R,R)- and (S,R)- and
10:1 to 1:10
 5:1 to 1:5
(S,S)-N(1-cyano-1,2-di-
methylpropyl)-2-(2,4-di-
chlorophenoxy)propionamide
chlorothalonil (DAC 2787)
 1:1 to 1:50
 1:5 to 1:20
triadimefon
10:1 to 1:10
 5:1 to 1:5
triadimenol
10:1 to 1:10
 5:1 to 1:5
epoxiconazole
10:1 to 1:10
 5:1 to 1:5
metconazole
10:1 to 1:10
 5:1 to 1:5
fluquinconazole
10:1 to 1:10
 5:1 to 1:5
cyproconazole
10:1 to 1:10
 5:1 to 1:5
penconazole
10:1 to 1:10
 5:1 to 1:5
kresoximmethyl
10:1 to 1:10
 5:1 to 1:5
azoxystrobin
10:1 to 1:10
 5:1 to 1:5
cyprodinil
 5:1 to 1:20
 1:1 to 1:10
iminoctadiene triacetate (Befran)
10:1 to 1:10
 5:1 to 1:5
flusilazole (Harvesan)
10:1 to 1:10
 5:1 to 1:5
prochloraz (Sportak)
10:1 to 1:10
 5:1 to 1:5
propiconazole (Desmel)
10:1 to 1:10
 5:1 to 1:5
bitertanol
10:1 to 1:10
 5:1 to 1:5
imidacloprid
20:1 to 1:20
10:1 to 1:10
dichlofluanid (Euparen)
 1:1 to 1:50
 1:1 to 1:20
tolylfluanid (Euparen M)
 1:1 to 1:50
 1:1 to 1:20
metalaxyl (Ridomil)
10:1 to 1:10
 5:1 to 1:5
fenpiclonil
10:1 to 1:10
 5:1 to 1:5
difenoconazole
10:1 to 1:10
 5:1 to 1:5
fludioxonil
10:1 to 1:10
 5:1 to 1:5
carbendazim, benomyl
10:1 to 1:10
 5:1 to 1:5
fuberidazol
20:1 to 1:10
10:1 to 1:5
imazalil
20:1 to 1:10
10:1 to 1:5
triazoxide (SAS 9244)
20:1 to 1:10
10:1 to 1:5
cyfluthrin (Pyrethroid)
20:1 to 1:20
10:1 to 1:10
guazatine
10:1 to 1:10
 5:1 to 1:5
acibenzolar-S

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