Note: Descriptions are shown in the official language in which they were submitted.
8 5
The present invention is concerned with new fungicidal-
ly active furancarboxylic acid anilides, with the use of these
compounds for controlling phytopathogenic fungi and also with a
process for the manufacture of the new active compounds.
Agents that act against phytopathogenic fungi have
already been known. Agents of this type known in practice are r
for example, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole (United
States Patent Specification Nos. 3,260,725 and 3,260,588) and
tetramethylthiuram disulphide (German Patent Specification No.
642,532). However, these agents do not always have a satis-
factory action against leaf and soil fungi.
The problem upon which the present invention is based
has been to provide an agent having a superior action against
leaf and soil fungi. This problem is now solved in accordance
with the present invention by the compounds of the general formula
I, as defined below.
The present invention provides compounds of the
general formula I
R ~ N - C ~ ~I)
in which
Rl represents a hydrogen atom or an alkyl group containing 1
to 4 carbon atoms,
R2 represents an unsubstituted phenyl group or a phenyl group
substituted by one or more substituents selected from
alkyl groups containing 1 to 4 carbon atoms~ alkoxy groups
3Q containing 1 to 4 carbon atoms, alkylthio groups containing
1 to 4 carbon atoms, halogen atoms, trifl~oromethyl groups,
nitro groups, alkoxycarbonyl groups containing 1 to 4 carbon
~, . .
:atoms in the alkoxy parts, alkylcarbonyl groups containing
1 to 4 carbon atoms in the alkyl parts, phenyl and cyano
groups, and
n represents 1 or 2.
When the substituted phenyl groups represented by R2
contains two or more substituents these substituents may be the
same or different.
The action of the compounds of the present invention
against leaf and soil fungi is surprisingly superior to that of
known agents having the same direction of action and these
compounds are also distinguished by a good plant tolerance and
a sufficient duration of action. In addition, since they do not
act phytotoxicall~ when applied in the quantities suitable in
practice, they may accordingly be used advantageously in
agriculture and horticulture for the control of leaf and soil
fungi.
The compounds of the present inven~ion have outstand-
ing fungicidal properties against harmful fungi.
In contrast to known fungicidal agents having on~y
a preventive action, such as, for example, N-trichloromethyl
thiophthalimide (United States Patent Specification ~o. 2,553,770)
and manganese ethylene bisdithiocarbamate (United ~tates Patent
Specification No. 2,504,404) the compounds of the present
invention surprisingly also have the additional advantage of a
curat~ye and systemic action which, therefore, makes it possible
also to control pathogenic agents which have already penetrated
into the plants.
The present invention accordingly also provides a
fungicidal preparation which comprises a compound of the general
3Q formula I, in admixture or conjunction with a suitable carrier.
The preparation may of course contain one or more compounds of
the general formula I.
8 ~
The present invention further provides a method of
protecting a living plant against phytopathogenic fungi, wherein `~
the living plant is treated with a compound of the general formula
I.
The present invention further provides a method o~
protecting a crop~larea against phythopathogenic fungi, wherein
the crop area is treated with a compound of the general formula
I.
The present invention further provides a method of
dressing seeds, wherein the seeds are treated with a compound of
the general formula I.
The present invention further provides a pack which
comprises a compound of the general formula I together with
instructions for its use for controlling phytopathogenic fungi.
The compounds of the present invention that are es-
pecially distinguished by a superior fungicidal action are those
of the general formula I in which Rl represents a hydrogen atom
or a methyl or ethyl group and R2 represents a phenyl, methyl-
phenyl, dimet~ylphenyl, ethylphenyl, isopropylphenyl, methoxy-
phenyl, ethoxyphenyl, methylthiophenyl, fluorophenyl, chloro-
phenyl, bromophenyl, dichlorophenyl, trifluoromethylphenyl,
nitrophenyl, cyanophenyl, methoxycarbonylphenyl, acetylphenyl
or biphenylyl group.
The new active compounds may be applied singly or,
alternatively, mixtures of at least two constitutionally
different compounds of the general formula I may be applied.
If desired, other fungicides, nematocides, herbicides or other
types of pest-controlling agents may be added depending on the
purpose. The active substances are advantageously applied in the
3Q form of fungicidal preparations, for example powders, strewable
pxeparations, granules, solutions, emulsions or suspensions, with
the addition of liquid and/or solid vehicles or diluents and,
- 3 -
.~. . ~,
11,7~5
if desired, of wetting, adhesive, emulsifying and/or dispersing
agents.
Suitable liquid carriers are, for example, water,
mineral oils or other organic solvents, for example xylene,
chlorobenzene, cyclohexanol, cyclohexanone, dioxan, acetonitrile,
ethyl acetate, dimethylformamide, isophorone and dimethyl sul-
phoxide.
Suitable solid carriers are, for example, li'me,kaolin,
chalk, talcum, attaclay and other clays as well as natural or
synthetic silicic acid.
As surface-active agents there may be mentioned, for
example, salts or lignin sulphonic acid, salts or alkylated
benzenesulphonic acids, sulphonated acid amides and salts !,
thereof, polyethoxylated amines and alcohols.
When the active substances are to be used for dressing
seeds, they may also be admixed with dyestuffs in order to give
the dressed seeds a clearly visible colour.
The proportion of active substance(s) in the fungi-
cidal preparations may vary within wide limits, ~he exact con
centration of the active substances used for the preparations
depending primarily on the quantity in which the preparations
inter alia are to be used for treating soil or seeds or for
treating parts of plants above the soil. The preparations may
contain, for example, approximately 1 to 80% by weight, prefer-
ably between 20 and 50% by weight, of active compound(s),
appxoximately 99 to 20% ~y weight of liquid or solid carrier and
also, if desired, up to 20% ~y weight of surface-active agent(s).
The new compounds of the general formula ~I) may be
produced by the process of the present invention~ as defined
below.
The present invention further provides a process for
the manufacture of a compound of the general formula ~, wherein
-- 4
,
a compound of the general formula II
(fH2)n - fH - NH 2
H ~ ~ (II),
Rl
in which Rl, R2 and n have the meanings given above, is reacted
in the presence of an acid-binding agent and, if desired, a sol-
vent with a furancarboxylic acid chloride of the formula III
''
Cl - CO - ~ ~
~ (III).
The amounts used of the compound of the general formula
II and the compound of the formula III are preferably in equi- ~;
molar proportions.
As acid-binding agents there ~ay be used, for example,
organic bases, for example pyridine, triethylamine or N,N-
dimethylaniline, or inorganic bases, for example hydroxides,oxides and car~onates of alkali metals and alkaline earth
metals, for example sodium, potassium or calcium.
As a solvent that may optionally be used, there may
be mentioned, for example, other, tetrahydrofuran, benzene or
ethyl acetate. Liquid acid-binding agents, for example pyridine,
may serve simultaneously as solvents.
The reaction is advantageously carried out at a tem-
perature within the range of from -10C to 120C.
rrhe products of the process of the present invention
3Q may be isolated in a manner known per se.
Some specific compounds of the pr~sent invention are
listed in the following Table.
-- 5 --
Name __ Physical constant
_ _
Furan-2-carboxylic acid [N-(2-oxoperhydro-
3-furyl)-2,6-dimethylanilide] M.p.: 135-138C
Furan-2-carboxylic acid [2-chloro-N-
(2-oxoperhydro-3-furyl)-anilide] M.p.: 98-100C
Furan~2-carboxylic acid [N-(2-oxo-
perhydro-3-furyl)-anilide~ M.p.: 140-141C
Furan-2-carboxylic acid [2,6-dîethyl-
N-(2-oxoperhydro-3-furyl)-anilide~ M.p.: 12~-125C
Furan-2-carboxylic acid ~2-ethyl-6-
methyl-N-(2-oxoperhydro-3-furyl)-
anilide] M.p.: 127-129C
Furan-2-carboxylic acid [2-methoxy-
N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 139-140C
Furan-2-carboxylic acid [2,6-dimethyl-
N-(5-methyl-2-oxoperhydro-3-furyl)-
anilide] M.p.: 190-191C
Furan-2-carboxylic acid [3,4-dichloro-
N~(2-oxoperhydro-3-furyl)-anilide] M.p.: 139-141C
Furan~2-carboxylic acid [2-methyl-
N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 132C
Furan-2-carboxylic acid [2,4-dimethyl-
N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 123-124C
Furan-2-carboxylic acid [3,4-dimethyl-
N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 122C
Furan-2-carboxylic acid [2,3-dimethyl-
N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 129-130C
Furan-2-carboxylic acid [3,5-dimethyl-
N-(2-oxoperhydro-3-furyl) anilideJ M.p.: 161-162C
Furan-2-carboxylic acid [2,4j6-trimethyl-
N-~2-oxoperhydro-3-furyl)-anilide] M.p.: 142 143C
Furan-2-carboxylic acid [3-methyl-N-
(2-oxoperhydro-3-furyl)-anilide M.p.: 121C
Furan-2-carboxylic acid C4-methyl-N-
(2-oxoperh~dro-3-furyl~-anilide] M.p.: 118-119C
Furan-2-carboxylic acid [3-chloro-N-
(2-oxoperhydro-3-furyl)-anilide~ M.p.: 134-135C
Furan-2-carboxylic acid ~4-chloro-N-
(2-oxoperhydro-3-furyl)-anilide] M.p.: 157-158C
3Q Furan-2-car~oxylic acid ~2-ethyl N-
C2-oxoperhydro~3-furyl~-anilide] M.p.: 122-123C
Furan-2-carboxylic acid [N-(2-oxo-
perhydro 3-furyl~-3-trifluoromethyl-
anilide] M.p.: 130-131C
6 -
Furan-2-carboxylic acid [4 isopropyl-N-
(2-oxoperhydro-3-furyl)-anilide] M.p.: 95-96C
Furan-2-carboxylic acid [3-bromo-N-(2-
oxoperhydro-3-furyl)-anilide] M.p.: 150-153C
Furan-2-carboxylic acid [4-methoxy-N-
(2-oxoperhydro-3 furyl)-anilide] M.p.: 149-151C
Furan-2-carboxylic acid [4-ethoxy-N-
(2-oxoperhydro-3~furyl)-anilide] M~po 87-88C
Furan-2-carboxylic acid [4-ethyl-N-
(2-oxoperhydro-3-furyl)-anilide] M.p.: 120-121C
Furan-2-carboxylic acid ~4-bromo-N-
(2-oxoperhydro-3-furyl)-anilide] M.p.: 137-140C
Furan-2-car~oxylic acid [3-fluoro-N-
(2-oxoperhydro-3-furyl~-anilide] M.p.: 142-144C
Furan-2-carboxylic acid [4-fluoro-N-
(2-oxoperhydro-3-furyl)-anilide] ' M.p.: 165~1~6C
Furan-2-carboxylic acid [4-methoxy-2-
methyl-N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 133-135C
Furan-2-carboxylic acid r2,5-dimethyl-
N-(2-oxoperhydro-3-fu~yl)-anilide] M.p.: 120-121C
Furan-2-carboxylic acid [2-ethoxy-N-
(,2-oxoperhydro-3-furyl)-anilide] M.p.: 150C
Furan-2-carboxylic acid [2,6-diisopropyl-
N-(2-oxoperhydro-3~furyl)-anilide] M.p.: 149-150C
Furan-2-carboxylic acid [3,5-dichloro-N-
(2-oxoperhydro-3-furyl)-anilide] M.p.: 143-145C
Furan-2~carboxylic acid r 3-chloro-2-
methyl~N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 151C
Furan-2-carboxylic acid [5-chloro-2-
methyl-N-(2-oxoperhydro-3-furyl~-anilide] M.p.: 138-139C
Furan--2-carboxylic acid [2-methoxycarbonyl-
N~(2-oxoperhydro-3-furyl)-anilide] M.p.: 110~112C ~.i
Furan-2-carboxylic acid [3-methoxy-N-(2-
oxoperhydro-3-furyl)-anilide~ M.p.: 145-148C
Furan-2-carboxylic acid [3-nitro N-(2-
oxoperhydro-3-furyl)-anilide] M.p.: 137-138C
Furan-2-carboxylic acid [3-chloro-N-(5-
methyl-2-oxoperhydro-3-furyl)-anilide] M.p~: 105-108C
Furan-2-car~oxylic acid ~3-methylthio~N- -
3Q (2-oxoperhydro-3-furyl)-anilide] M.p.: 154~155C
Furan-2-carboxylic acid ~5-chloro-2-
methoxy-N-(,2-oxoperhydro-3-furyl~-anilide M.p.- 171-173C
Furan-2-carboxylic acid [3-fluoro-N-(5-
methyl-2-oxoperhydro-3-furyl)-anilide] M.p.: 93~94C
Furan-2-carboxylic acid [4-phenyl-N-(2-
oxoperhydro-3-furyl)-anilide] M.p.: 186-187C
Furan-2-carboxylic acid [3-acetyl-N-(2-
oxoperhydro-3-furyl)-anilide] M.p.: 166-167C
Furan-2-carboxylic acid ~2-chloro-6-methyl-
N-(2-oxoperhydro-3-furyl)-anilide] M.p.: 145-148C
Furan-2-carboxylic acid [2-bromo-N-~2-
oxoperhydro-3-furyl)-anilide] M.p.: 118C
Furan-2-carboxylic acid [2,3-dichloro-N-
(2-oxoperhydro-3-furyl)-anilide] M.p.: 126C
lD Furan-2-carboxylic acid [3-chloro-2-
methoxy-N-(2-oxoperhydro-3-furyl)-
anilide] M.p.: llS/116-117C
Furan-2-ca~rboxylic acid [3-ethyl-N-2-
oxoperhydro-3-furyl)-anilide] M.p.: 128-12~C
Furan-2-carboxylic acid [3-cyano-N-(2-
oxoperhydro-3-furyl)-anilide] M.p.: 131/132-134C
The compounds of the present invention are generally
almost colourless, odourless, crystalline substances that are
practically insoluble in water and benzine but, on the other hand
hand, vary readily soluble in polar organic solvents, for example
acetone, dimethylformamide and dimethyl sulphoxide.
2~ The starting compounds for the manufacture of the
compounds of the present invention are known per se or may be
produced according to processes known per se ,
The following Examples illustrate the invention.
Examples 1 to 3 illustrate the manufacture of the compounds of
the present invention and Examples 4 to 13 illustrate the
possibilities of application of the compounds of the present
invention.
Example 1
Furan-2-carboxylic a id [N_(2-oxope~ydro-3-furyl)-
3a 2,6-dimethyl-anilide]
-- 8 --
206.2 g (1.58 mole) of furan-2-carboxylic acid chlor-
ide were added dropwise, at room temperature and while stirring,
to a solution of 300 g tl.46 mole~ of 3-(2,6-dimethylanilino)-
perhydrofuran-2-one in 600 ml of dry pyridine. After the addi-
tion was complete a pyridine complex precipitated out with a
simultaneous increase in temperature. Heating was effected for
3 hours at 50C and the whole was then concentrated in vacuo
to half its volume. The mixture was then poured, while stirring,
into 2.5 1 of ice-cold 5% hydrochloric acid and after 30 min-
utes filtered with suction. Washing with a large amount ofwater and drying ln vacuo at 70C were then carried out.
Yield: 387 g = 89% of the theoretical yield.
M.p.: 135-138C.
Example 2
Furan-2-carboxylic acid [2-chloro-N-(2-oxoperhydro-
3-furyl)-anilide]
13.05 g (0.1 mole) of furan-2-carboxylic acid chloride
were added at room temperature to 21.16 g (0.1 mole) of 3-(2-
chloranilino)-perhydrofuran-2-one. The reaction mixture was
heated slowly to 120C and maintained at this temperature for
1.5 hours until the evolution of hydrogen chloride had been
completed. After cooling, 100 ml of ethyl acetate were added ;
and the mixture was washed until neutral with a saturated sodium
bicarbonate solution. The ethyl acetate phase was dried with
magnesium sulphate, fil~ered and concentrated in vacuo. The
resulting oil was crystallized with a little ether and filtered
off with suction, and the resulting crystals were washed with
diisopropyl ether.
Yield: 21.4 g - 70% of ~he theoretical yield.
M.p.: 98-100C.
Example 3
Furan-2-car~oxylic acid ~N-[2~oxoperhydro-3~furyl)-
_ _ . ......... _ ... _ _
anilide]
,
1~5g~
A solution of 14.16 g (0.08 mole) of 3-anilinoper-
y hydro furan-2-one in 150 ml of ethyl acetate and a solution of
9.54 g ~0.09 mole) of sodium carbonate in 15 ml of water
were mixed by stirring. 11.70 g (0.09 mole) of furan-2-caxbox-
ylic acid chloride were then added dropwise while cooling with
ice. The mixture was then stirred for an hour, if necessary
neutralized with a little soda solution and extracted by shak-
ing with ethyl acetate. After drying over magnesium sulphate
the ethyl acetate solution was concentxated to dryness in vacuo
and the solid residue was treated with a little ether/ethanol.
The whole was filtered with suction, washed with ether and
recrystallized from ethanol.
Yield: 10.6 g = 49~ of the theoretical yieldO
M.p.: 140-141C.
Each of the other compounds of the present invention
listed in the Table above may be produced in a manner analogous
to that described in any one of Examples 1 to 3.
Example 4
Limiting concentration test in the control of
Pythium ultimum
In a series of tests 20% pulverulent active substance
preparations were mixed uniformly with soîl which was severely
infected with Pythium ultimum. The treated soil was placed in
. . . :
clay dishes each having a capacity of 0.5 litre and, without
a waiting period, 20 marrowfat pea seeds of the Kelvedon Wonder
variety were sown in each dish. After a cultivation period of
3 weeks at 20 to 24C the numbex of sound peas was de~ermined
and a root assessment (1-4 as defined below) was carried out.
The active substances used and their application
quantities, and also the results, are given in the following
Table.
.
~ 10 -
~ ~-r ~r 1l;3 V
o ~ n ~ ~ r- u~ oo ~ C~ ~ ~ ~n r. ~ r
10 ~ ~ ~ I ~ ~ ~ 1 ~ 1
~ :
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~o
~l ~
~ a~ o o o o o o o o o o o o o o o o o o ~:.
'~ ~ ~ ~ ~ er ,1 ~ ~:r ,J ~ ~r, ,i ~ ~r ,1 ~ ~r ,1 ~ ~ ':~
~ o ~
o~ ~ ~ l z ~ z
~C O ~ ~ ~r_ O Or~l~ ~:
~ l ~ ~ s~ o~ ~
_ ~ r_ I ~ O ,1 ~5 rl h rl
.~ ~ --a~ ~ ~ ~ u~ ,q~
~i Z I ~ ~ I -~1 i ~rl I ~1
_ Z-~l t~ I ~ ~:: ~ ~ ~
~ ~d ~- ~d ~ :
~ ~ ~ r~ ~1 f-l~l ~rl ~ , .
O O o ~1 U ~ O ~ ~ ~ U
l :~ rd S~ 1~ ~ ~ ~ d h
t~ U U'5 U ~, ~ :1 t) ~ o~Z
rl~ ~rl Q) r~ O ~ ~-1 1 ,-
,~ ~1 ~ -~ E3 ~1 ~C ~ ~1 ~ ~ ~
h X ri X ~ X 1 ~ o X O X O
O O ~1 O I O ~ O ~ 0 5~ O h
C) ,{1 rl Q ~D .4 1 Q ~ Q ~ ~ ~:1
U ~ h ` h ~ S~ h :~ ~ :~
U I t~ ~ (a ~ U Ll ~ ~ ~ h
~ 1~ I_ I ~ I a) I O I O
1~ N r-l t~l r~l t~ a) tl) t~ ~4 N ~1
I ~ I ~ ~ ~ ~ ~ O I O I O
î~ :~ ~ h ~ u~ ~1 1 o ~S X ~:
~ 4~ ~ ~ rl 5~ 1 ~ I h I
O ~ I ~ I ~ ~ N ~ N
~ 14 ~ ~ Z ~ 14--
,... -- 11 --
~ ,. ~" ' .
11~ 5
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,~ I I ~ er ~r
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h .
10 ~ .~ ~
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o o oc~ o o _~ _~ O a
.~ ~ ~ ~ ~ i~ ,4 U ~11 ,SI U
~ UO ~ t~
~ ~I h O
~ o ~
'3
~:, ~ l 0~
~: ~1 ~ . ~ a) ~ h
,1 .1 .~ ~I-SI ~3
a) ~ :~ 3 3: Q tQ
11 11 11 11 :.
~ ~--
$ ~d ~ 0 h
1~ .,~ tH . ~ O
.,1. ~ ~ 5~ ~ ..
I ~ U _~ ~
h X O ~.,1 ~ _~ ~:
O ~ ~1 ~3~1 ~ r~ 1~
V A ~ O ~ o .,1 F~ ~1 E3
U 5~ OI O ~1 o o-~
~d ~tl ~ ~ 1 ~ u~ ~_1 ,1 o t~
V h hI O H ~1 H ~ 1:11 a)
1 0 O~ N ~ ~ ~1 U)
t~ 4-1~c la ~_1 O ~ ~_1 ~ ~ Il)
::1 I o o ,~ o Q,~ O . a) a) ~d
o ~: x ~~: ~ ,, a) c) ~1
o ~~ ~ ~ ~ a) ~ a) ~ ~
~i ~1 I 0~1 rl ~ i ~H ~ h 0 O
O ,~ t~ tJ)I ~: O ~ S: O ~ O
E'---' '¢ ~ ~ ~--H C.) ~) U~ p:~
-- 12 --
`` '` !
1 ~5~i5
Example 5
Dressing of su~ rbeet seeds
In a series of tests gr~ded sugarbeet seeds o~ the
Dieckmann-Suprapoly variety were dressed with 20~ pulverulent
active substance preparations. Clay dishes each of 2 litres
capacity (20 x 20 x 5 cm) were filled with normal compost soil
(damping-off) and lO0 of the sugarbeet seeds were sown in each
dish. After a cultivation period of 18 days at 19 - 21 C in a
greenhouse the number of sound seedlings was determined.
The active substances used and their application
quantities, and also the results, are given in the following
Table.
Compound accordin~ to the ~ctive substance Number o~
InYention 'n u/kg seed sound seedlings
_ lQO~seeds
Furan-2-carboxyl~c ac~d~N 0-.-4 g 84
(2-oxoperhydro-3-~uryl)-2,6- 0.8 g 90
dimethylanilide] 1.6 g 91
Furan-2-carboxylic acid [3- 0.4 g 73
chloro-N-(2-oxoperhydro-3- 0.8 g 71
furyl)-anilide] 1.6 g 91
Furan-2-carboxylic acid [3- 0.4 g 75
fluoro-N-(2-oxoperhydro-3- 0.8 g 79
furyl)-anilide] 1.6 g 75
_
Furan-2-carboxylic acid [2,3- 0.4 g 74
dimethyl-N-(2-oxoperhydro-3- 0.8 g 82
furyl)-anilide] 1.6 g 85
Furan-2-carboxylic acid [3-methyl- 0.4 g 72
N-(2-oxoperhydro-3-furyl)- 0.8 g 78
anilide] 1.6 g 79
Furan-2-Ga~rboxylic acid [2,6- 0.4 g 57
dimethyl-N-(5-methyl-2-oxoper~ 0.8 g 70
hydro-3-furyl)-anilide] 1.6 g 92
Furan-2~carboxylic acid ~3- 0.4 g 56
bromo-N-(2-oxoperhydro-3-furyl)- 0.8 g 55
anilide] 1.6 g 75
Agents for comparison
5-Ethoxy-3-trichloromethyl- 0.4 g 26
1,2,4-thiadiazole 0.8 g 44
1.6 g 53
Tetramethylthiuram disulph~de 4.8 g 21
9.6 g 5
.
Control I
(3 repetitions a) 5
Infected soil ~) 7
c~ 6
.
Control Ir
(3-re~etition~ a~ 83
Steamed so~ 81
1~ -
$ 5
Example 6
Control of Rythi~ splendens in t~e pot cultivation o~ Poinsettia
pulcherri~a
~ .. ... :
In a series of tests ~oung poinsettia plants of the
Annette Hegg Diva variety which had taken root were potted in
clay pots each of 11 cm in diameter. The pot substrate (peat ,-
culture substrate + sandy compost soil 1 : 1) was severely
infected with Pythium sple-ndens. After potting, 100 ml of the
preparation under test and having the concentration indicated
in the Table below werepoured once over the plants. There
followed a cultivation period of 10 weeks at 20 to 21C in a
greenhouse. At the end of the cultivation period the height
of each of 10 plants was measured, the fresh weight of the
leaves and bracts was determined and a root assessment (1 - 4
as defined below) was carried out.
The active substances used and their application quan-
tities, and also the results, are given in the following Tabla.
:
_
_ :
1~ R ~1~1,1 --1~1 r-l ~ ~ O
10 '~
~. ~ ~ ~ ~ ~ ~r ,
~0
o o~ ~`3 CO ~` ~ ~ ~
~ r ~ ~1
a~ ~ dP d~ dP d~
N el~ OD
v o o a cY o
.
'
~ ~ l
~ ~ ~ ¦ ~ ~ ¦ H
~ N ` ¦ _ ~3
-~ .,
, :, \ -- 16 -- :
Exa~ple 7
Control o~-bulh s~t ~ot and ~bulb root rot in tulip cultivation
In a ser~es o~ tests prepaxed tulip bulhs (5C tulips)
o~ the Gander variety were peeled and 12 bulbs in each case were
planted in wooden boxes each measuring 27 x 27 x 12 cm. The
plant su~strate ~sandy compost soil) was severely infected with
Pythium ultimum and Pythium sylvaticum. The preparation under
test, as a 10% pulverulent preparation, was worked uniformly
into the compost ~efore planting. There followed a cultivation
period of 47 days at a soil temperature rising slowly from 12
to 17C. The mature flowers were weighed, the plant losses
as a result of bulb rot were determined, and a root assessment
(1-4 as defined below) was carried out.
The active substance used and its application quanti-
ties, and also the results, are given in the following Table.
- 17 -
$ 5
_
' O ~o, ~ ~r er ~ ~ '
O ~ ~ P ~P d~
o o o ~ U~
~:4 ~ R a~ I`
a) a) ~ ~ ~ ~ ~ tJ
0~ ~ u~u~r`
~ ~ O ~ r
~o~ ..
o ~ ~ ~
0 0 0 ~ ~5 ~ Q)
Q) ~ ~ ~r ~ S
t) k .
~1 11 11 11
V ~ l
rl ~ 'I n) ~,~ ..
~1 Q)
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-- 18 --
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Exam~le 8
Control o~ Ph~top~t~or~ paras~tica ~'ar.' ni'coti'a'nae ~n the pot
_ult~vation o~ S~nning~a specosa (~loxinia)
In a series of tests ~oung Sinningia plants of the
Gierth's Blaue variety were potted in clay pots each of ll cm in
diameter. The pot substrate was a l : 1 mixture of peat culture
substrate and sandy compost soil. After potting, lO0 ml of the
preparation under test and having the concentration indicated in
the Table below were poured once over the plants. 3 days after-
wards the pots were inoculated uniformly with mycelium flocci of
a 3-week-old Phytophthora culture. There followed a cultivation
period of 7 weeks at 22 to 24C in a greenhouse.
The active substance used and its application quantities,
and also the results, are given in the following Table.
C~x~d according Active substance Plant losses Average fre~h
to the invention concentrationafter 7 weeks weight of the
plants after
' 7 weeks
Furan-2-carbcxylic 0.01 % O ~ 217 g
acid ~N-(2-oxoperhydro- 0.02 % O ~ 259 g
3- ~ yl)-2,6-dimethyl- 0.04 % 0 % 223 g
20 anilide]
Control I
In~ated sn % 140 g
Control II
Not inoculated - 0 ~ 239 g
~ . . _ .. . .
Example 9
Control of Pythium ultimum in the pxvpagation of Pelargonium
cuttings - ' ~
In a ~eries of tests cla~- pots each o~ 6 cm in diameter
were ~illed with a pxopa~gat,ion sub~trate ~Jhic~ was severely in-
fected with Pyth~u~ ulti~um. The su~strate was a mixture of
19 -
8~5
3 parts o~ peat culture substrate and 2 parts of sand. 30 ml
of t~e acti~e su~stance concentration indicated in the Ta~le
below was poured on to the soil surface in each pot. Afterwards,
shoots, which had not taken root, of Pelargonium peltatum of
the Luisenhof variety were planted in 24 pots per test series.
After a cultivation period of 25 days at 22 to 25C in a propa-
gation bed the plant losses were ascertained and the average
fresh weight o~ the cuttings which has taken root was determined.
The active substances used and their application quanti-
ties, and also the results, are given in the following Table.
Compound according Active substance Plant losses Average fresh
to the invention concentration weight of the
plants
.
Furan-2-ca~boxylic 0.005 % O % 7.3 g
acid 13-chloro-N- 0.01 % Q % 7.1 g
(2-oxoperhydro,3-
~yl)-anilide]
_ .
Furan-2-carboxylic 0.005 % 0 % 6.2 g
acid [N-(2-oxoper- ~.01 ~ O ~ 6.8 g
hydro-3-~yl)-2,6-
dimethylanilide]
-
Control I
~0
Infected soil . - 83 % 2.6 g
Control II
Steamed soil - 0 % 6.8 g
,
Exa~ple 10
Effect of prophylactic leaf treatment against Plasmopara
viticola on vines in a ~reenhouse
In ~ s.er~es of test$ young vines having approximately
5 to 8 leayes were spra~ed unt~l dr~ppin~ wet with the concentra-
tion o~ act~Ye substance indicated ~n the Ta~le below and, after
the spra~ coatin~ ~ad dried on, an aqueous suspension of sp~ran-
gia of the fun~us indicated in the heading above (app.rroxi-
- 20 -
mately 20,QOQ per ~1) was ~prayed on th.e undersides o~ the
leaves and plants were then immediately incubated in a green-
house at 22 to 24C ~n an at~osp~ere as saturated with steam as
possible. From the second day on the air humidity was reduced
for 3 to 4 days to the normal le~el (30 to 70% saturation) and
then maintained for a further day at steam saturation. The per-
centage proportion o~ the surface attacked by fungi of each
leaf was then noted and the avera~e per treatment was calculated
as follows to determine the ~ungicidal effect:
100 - lQ0 x a~tack in treated plants = % effect
attack in untreated plants
% Effect against Plasmopara viticola in vines +)
Compound according to Concentration 0.001
the invention (% active substance)
-
Furan-2-carboxylic acid ~N- 100
~2-oxoperhydro-3~furyl)-2,6-
dimethylanilide~
Furan-2-carboxylic acid
~2,6-dimethyl-N-(5-methyl-
2-oxoperhydro-3-furyll-
aniltde] 100
Furan-2-carboxylic acid [3-
chloro-N-(2-oxoperhydro 3-
furyl~-anilide] 98
Agent for comparison
N-Trichloromethyl thio-
phthalimide 80
+~ Effect was calculated on lQ0 % attack in the untreated
control.
~Q
21 -
Exa~ple 11
Effect of ~oph~lactic lea~ treatment against Ph~tophthora
infestans in tomato plants or potato plants in a greenhouse
In a ,eries o~ tests young tomato plants having at
least two developed folia~e leaves and potato plants (for example
from eye cuttings) at least 10 cm tall were sprayed until
dripping wet with the concentration of active substance indicated
in the Ta~le below and, after the spray coating had dried on,
they were ~pxayed with an aqueous suspension which contained
per millilitre 50,0Q0 to 80,0QQ sporangia of the fungus indicated
in the heading above and which had been incubated for approxi-
mately 2 hours in a refrigerator at 11C. The plan~.s were
incubated at a high level of air humidity and approximately
15 to 18C in a greenhouse and after approximately 5 days the
percentage proportion of the leaf surface that had been at~acked
was assessed. The fungicidal effect was calculated as follows: :
100 - 1_0 x attack in treated plants = % effect
.
attack in untreated plants
% Effect against_Phytophthora infestans in -,potatoes ~) ;
~ Compound according to Concentration 0.005 0.001
t,ke,,~.nve,ntion ~% active substance)
_
Furan-2-carboxylic acid
[N-(,2-oxoperh~dro-3-
furyl~-anilide] 70
Furan-2-carboxylic acid
[N-(2-oxoperhydro-3-
furyl)-2,6-dimethyl-
anilide~ 100 9
Furan-2-car~ox~lic acid
~2,6-d~methyl-N-(5-
methyl-2-oxoperh~dro-
3-~ur~ anil~de~ ~5 95
~gent for comparison
Man~anese et~ylene b-isdi-
thiocarh~ma,te 50 30
22 -
:. .
~ Effect ~gainst Ph~.to.phthora : nfe:s.tans in .tomat~.e.s.~)
Co~pound a~ccording to Concentration 0.005 0.001
t~e invent~on- (:~ active substance)
:
Furan-2-ca~o~l~c Acid 100 86
~N-C2-oxoperh~dro-3-
furyll-2,6-dlmethyl~
anil~de] 100 86
Furan-2-carboxylic acid
L 2, 6-dimethyl-N- (5
methyl-2-oxoperhydro-
3-furyl)-anilide~ 100 86
Furan-2-car~ox~lic acid
[2,3-dimeth~l-N-~2-
oxoperhydro-3-furyl)-
anilide~ 71
Furan-2-carboxylic acid
13-chloro-N- t2-oxoper-
hydro-3-furyl)-anilide] 100
Furan-2 carboxylic acid
[3-fluoro-N-C2-oxoper-
hydro-3-furyl~-anilide] 81
Agent for comparison
Manganese ethylene ~isdithio-
carbamate 67 0
~) Effect was calculated on 100 % attack in the untreated control.
- Example -12
Systemic effect o~ soil treatment against Phytophthora infestans
in tomato plants or in potato plants in a greenhouse
In a series of tests the active substances to be
tested, ~hich ~ad been weighed out, (weight by volume), were
mixed w~th soil which was then placed in plant pots and young
to~ato plants having at least two developed foliage leaves and
potato plants (f~r example from eye cuttin~s) at least 10 cm tall
wexe placed in these pots. After the expiry of the desired pre-
dose t~e C~r exa~ple a~ter 3, 4 or 18 days) the plants were
~pxa~ed ~th. an
3Q
- 23 -
6 ~
aqueous su~pension ~h~ch. contained per millilitre 50,000 to
8Q,QQQ sp~X,an~i`,a o~ the ~ungus ~nd~cated in the heading above
and wh~ch.had been Incubated for approximately 2 hours in a
refrigerator at 11C. The plants wére incubated at a high level
of air ~umidity and at approximately 15 to 18C in a greenhouse
and after approximately 5 days the percentage proportion of lea~
surface that ~ad been attacked was assessed. The fungicidal
effect was calculated as follows:
100 - 100 x attack in treat_d plants - % effect
attack in untreated plants -.
Systemic effec.t o~..soil treatment against Phytophthora:.infestans
in tomato plants ~Weight active substance/volume)
.
Compound according ppm active % Effect +) ' o~ treatment
to the invention su~stance 4 days before 18 days before
inoculationinoculation
Furan-2-carboxylic
acid lN-(2-oxoperhydro-3- 25 32 75
furyl)-anilide] . 5 10 32
Furan-2-carkoKylic acid [N-
(2-oxoperhydro,3 ~yl)- 25 60 92
2,6-dimethylanil~de~ 5 27 66
Furan-2-carbRxyltc acid 12,6-
dimethyl-N-(5-methyl-2-
oxoperhydro-3-furyll- 25 94 100
anilide] ' 5 57 95
~) Effect was calculated on 100 ~ attack in untreated control.
- 24 -
6 5
Exa~p-le 13
Curatl~ve e~ect o~ lea~ treatment ~ainst Phytophthora infestans
. in .tomato plants.''.or.''.p.o.tato plants in a ~reenhouse
In a series of tests young tomato plants hav.ing at
least 2 de~eloped foliage leaves and potato plant (for example
$rom eye cuttings) at least 10 cm tall were sprayed with an
aqueous suspension w~ich contained per millilitre 50,000 to
8Q,000 sporangia of the fungus indicated in the heading above
and which has been incubated for approximately 2 hours in a
refrigerator at 11C. The plants were incubated at a high level
of air humidity. After the expiry of the desired pre-dose time
the plants were sprayed until dripping wet with the concentra-
tion to ~e tested on the fungicide (indicated in the Table below)
within the period of latent fungal attack. After the outbreak
of fungal attack in the untreated control plants the percentage
proportion of leaf sur~ace that had been attacked wa~ assessed.
The fun~icidal e~fect was calculated as follows:
lQ0 - .l.O.O.x .attack in treated plants = % effect
attack in untreated plants
Ca~x~nd accordin~ to ~ ActiYe % Effect ~) of treatment
t~2 invention substance before 1 day after
. spraYed inoculation inoculation
... . . . . . . . .
Furan-2-carfioxylic ac~d
~N-~2-oxoperhydro-3-
furyl)-2,6~ hyl-
anilide~ 0.004 100 75
Furan-2-car~oxylic
acid ~,6-dimethyl-N ~5-
meth~l 2-oxoperhy~x~3-
furyl~-an~lide] 0.Q04 100 47
A~ent'fo~'ce~
M~nganesP ethylene ~isdi-
t~iocarEamate Q.004 91 0
Ef~ect w~$ calc~lated on lQQ ~ attack i.n the untreated control.
- 25 -
