Plant protecting and regulating compositions – Plant growth regulating compositions – Plural active ingredients
Reexamination Certificate
2000-02-28
2001-05-22
Robinson, Allen J. (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Plural active ingredients
C504S148000
Reexamination Certificate
active
06235684
ABSTRACT:
The present invention relates to novel fungicidal compositions for the treatment of phytopathogenic diseases of crop plants, especially phytopathogenic fungi, and to a method of combating phytopathogenic diseases on crop plants.
It is known that certain 2-(5-phenyl-3,6-diaza-2,7-dioxa-octa-3,5-dienyl)-phenylacrylic acid derivatives have biological activity against phytopathogenic fungi, e.g. known from WO 95/18789, WO 95/21154 and WO 97/20809 where their properties and methods of preparation are described. On the other hand azole derivatives, phthalimides, phenylamides, morpholines and aminopyrimidines and numerous further compounds of different chemical classes are widely known as plant fungicides for application in various crops of cultivated plants. However, crop tolerance and activity against phytopathogenic plant fungi do not always satisfy the needs of agricultural practice in many incidents and aspects.
It has now been found that the use of
a) a 2-(5-phenyl-3,6-diaza-2,7-dioxa-octa-3,5-dienyl)-phenylacrylamide of formula I
wherein
R
1
is hydrogen, fluoro or chloro,
R
2
is methyl, ethyl, trifluoromethyl, trifluoromethoxy, cyano, fluoro, chloro or bromo, with the proviso that R
2
cannot be fluoro, chloro or bromo, when R
1
is hydrogen;
in association with
b) either an anilinopyrimidine of formula II
wherein
R
3
is methyl, 1-propynyl or cyclopropyl;
or an azole of formula III
wherein
A is selected from
whereby the &bgr;-carbon attaches to benzene ring of formula III, and wherein
R
4
is H, F, Cl, 4-fluorophenoxy or 4-chlorophenoxy;
R
5
is H, Cl or F;
R
6
and R
7
are independently H or CH
3
;
R
8
is C
1-4
alkyl or cyclopropyl;
R
9
is 4-chlorophenyl or 4-fluorophenyl;
R
10
is phenyl, and
R
11
is allyloxy, C
1-4
alkyl, or 1,1,2,2-tetrafluoroethoxy-methyl, and the salts of such azole fungicide;
or a morpholine fungicide of formula IV
wherein
R
12
is C
8-15
cycloalkyl, C
8-15
alkyl, or C
1-4
alkylphenyl-C
1-4
alkyl, and the salts of such morpholine fungicide;
or a strobilurin compound of formula V
wherein
X is NH or O
Y is CH or N, and
R
13
is 2-methylphenoxy-methyl, 2,5-dimethylphenoxy-methyl, 4-(2-cyanophenoxy)-pyrimidin-6-yloxy, or 4-(3-trifluoromethylphenyl)-3-aza-2-oxa-4-pentenyl;
or a pyrrole compound of the formula VI
wherein
R
14
and R
15
are indendently halo, or together from a perhalomethylendioxo bridge;
or a phenylamide of the formula VII
wherein
R
16
is benzyl, methoxymethyl, 2-furanyl or chloromethyl,
R
17
is 1-methoxycarbonyl-ethyl, or
Z is CH or N;
or a dithiocarbamate fungicide selected from mancozeb, maneb, metiram and zineb;
or a copper compound selected from copper hydroxide, copper oxychloride, copper sulfate and oxine-copper;
or sulfur;
or a phthalimide compound of the formula VIII
wherein
R
18
and R
19
together form a 4-membered bridge —CH
2
—CH═CH—CH
2
— or ═CH—CH═CH—CH═;
or with the compound of formula IX
or with the compound of formula X
or with the compound of formula XI
or with the compound of formula XII
or with the compound of formula XIII
or with the compound of formula XIV
or with the compound of formula XV
or with the compound of formula XVI
or with the compound of formula XVII
or with the compound of formula XVIII
or with the compound of formula XIX
or with the compound of formula XX
or with the compound of formula XXI
or with the compound of formula XXII
or with the compound of formula XXIII
or with the compound of formula XXIV
or with 2-chloro-N-(4′-fluoro-1,1′-biphenyl-2-yl)nicotinamide (compound XXV),
or with 2-chloro-N-(4′-chloro-1,1′-biphenyl-2-yl)nicotinamide (compound XXVI),
or with methyl N-(2-[1-(4-chlorophenyl)pyrazol-3-yloxymethyl]phenyl)-N- methoxycarbamate (compound XXVII),
or with methyl N-(2-[1-(4-tolyl)pyrazol-3-yloxymethyl]phenyl)-N- methoxycarbamate (compound XXVIII),
or with 2-[4-methoxy-3-(1-methylethoxy)-1,4-diazabuta-1,3-dienyloxymethyl]phenyl-2-methoximino-N-methylacetamide (compound XXIX),
or with 2-[4-methoxy-3-(1-methylpropoxy)-1,4-diazabuta-1,3-dienyloxymethyl]phenyl-2-methoximino-N-methylacetamide (compound XXX),
or with N-(cyclopropylmethoxy)-N′-(2-phenylacetyl)-2,3-difluoro-6-trifluoromethyl-benzamidine (compound XXXI),
or with N-[3′-(1′-chloro-3-methyl 2′-oxopentan)]-3,5-dichloro-4-methylbenzamide (compound XXXII),
or with methyl(2)-2-{6-[6-(trifluoromethyl)pyrid-2-yloxymethyl]-phenyl}-3-methoxyacrylate (compound XXXIII),
or with 2-chloro-4-(2-fluoro-2-methylpropionylamino)-N,N-dimethylbenzamide (compound XXXIV),
or with (S)-1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one (compound XXXV),
or with N-methyl-2-{2-[&agr;-methyl-3-(trifluoromethyl)benzyloximinomethyl]phenyl}-2-methoximinoacetamide (compound XXXVI),
or with a (S)-valinamide of formula XXXVII)
wherein
R
20
is isopropyl, sec.-butyl or tert.-butyl, and
R
21
is 4-chlorophenyl, 4-tolyl, 4-methoxyphenyl or &bgr;-naphthyl, preferably the compound isopropyl 2-methyl-1-[(1-p-tolylethyl)carbamoyl]-(S)-propylcarbamate (compound XXXVIIa);
or with a (S)-valinamide of formula XXXVIII
wherein
R
20
is isopropyl, sec.-butyl or tert.-butyl,
R
22
is halogen, methyl or methoxy,
and n is 0, 1, or 2;
or with an azole of formula XXXIX
wherein
R
23
is chloro or fluoro, and
R
24
is hydrogen or methyl;
is particularly effective in combating or preventing fungal diseases of crop plants. These combinations exhibit synergistic fungicidal activity.
Among the components b) all the compounds except those of formulae XXV to XXXIX are mentioned as a particular subgroup.
Throughout this document the expression combination stands for the various combinations of components a) and b), e.g. in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, e.g. a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, e.g. a few hours or days. The order of applying the components a) and b) is not essential for working the present invention.
The combinations according to the invention may also comprise more than one of the active components b), if broadening of the spectrum of disease control is desired. For instance, it may be advantageous in the agricultural practice to combine two or three components b) with the any of the compounds of formula I, or with any preferred member of the group of compounds of formula I.
From WO 95/18789, WO 95/21154 and WO 97/20809 the following specific species of formula I are known:
Compound
No.
R
1
R
2
1.01
H
4-CH
3
1.02
H
4-C
2
H
5
1.03
2-Cl
4-Cl
1.04
H
4-CN
1.05
H
4-OCF
3
1.06
2-F
4-CH
3
1.07
2-F
4-F
1.08
2-Cl
4-F
1.09
2-F
4-Cl
1.10
2-F
4-CF
3
A preferred embodiment of the present invention is represented by those combinations which comprise as component a) a compound of the formula I wherein R
1
is fluoro or chloro and R
2
is methyl, trifluoromethyl, fluoro, chloro or bromo.
Most preferred subgroups of formula I are those wherein R
1
is fluoro or chloro and R
2
is methyl, chloro or fluoro; or wherein R
1
and R
2
are independently fluoro or chloro; or wherein R
1
is hydrogen, fluoro or chloro and R
2
is methyl, fluoro or chloro, provided that R
2
is methyl when R
1
is hydrogen.
Among the mixtures of present invention most preference is given to the mixtures of compounds 1.01, 1.03, 1.05, 1.06, 1.07, 1.08 and 1.09 with the compounds of component b), especially the commercially available products falling within the given ranges, i.e. the commercial products mentioned throughout this document. Particular preference is given to the combination of compound 1.01 with any of the components b), and to the combination of compound 1.07 with any of the components b).
Salts of the azole, amine and morpholine active ingredients are prepared by reaction with acids, e.g., hydrohalo acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydro
Gsell Bettina
Knauf-Beiter Gertrude
Zurfluh Rene
Novartis Crop Protection, Inc.
Pryor Alton
Robinson Allen J.
Teoli, Jr. William A.
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