Note: Descriptions are shown in the official language in which they were submitted.
The present invention is concerned with new fungicidally
active cyclopropanecarboxylic 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 kind known in practice are,
for example, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole
(United States Patent Specifications Nos. 3,260,588 and 3,260,725)
and tetramethylthiuram disulphide (German Patent Specification
No. 642,532). These agents, however, do not always have a satis-
factory action against phytopathogenic fungi.
The problem upon which the present invention is based
has been to provide an agent having an outstanding action against
phytopathogenic 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
~0 ~ ) _ 0~ o-a / ¦ (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
containing 1 to 4 carbon atoms, alkylthio groups containing 1 to
4 carbon atoms, halogen
`~
6~
atoms, trifluoromethyl groups, nitro groups, alkoxycarbonyl
groups containing 1 to 4 carbon atoms in the alkoxy part,
alkylcarbonyl groups containing 1 to 4 carbon atoms in the alkyl
part, phenyl,and cyano groups, and n represents 1 or 2.
When the substituted phenyl group 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 phytopathogenic fungi is surprisingly superior to that
of known agents having the same direc~ion of action and, moreover,
these compounds are distinguished by a good plant tolerance and
a sufficient duration of action. Since, in addition, they do
not act phytotoxically when applied in the quantities that come
into consideration in practice, they may accordingly be used
advantageously in agriculture and in horticulture for controlling
phytopathogenic fungi.
The compounds of the present invention have outstanding
fungicidal properties against pathogenic fungi, for example
false mildew fungi.
In contrast to known fungicidal agents having only a
preventive action such as, for example, N-trichloromethyl
thiophthalimide (United States Patent Specifications Nos.
2,553,770, 2,553,771 and 2,553,776) and manganese ethylene
bisdithiocarbamate (United States Patent Specifications Nos.
2,504,404,and 2,710,822), the compounds of the present invention
':~
~ 30
' ' .:'
~ .
11~8~61
surprisingly also have the additional advantage of a curative
and systemic action which, therefore, makes i~ possible also
to control pathogenic agents that have already penetrated into
the plants.
The present invention accordingly also provides a
fungicidal preparation which comprises a compound of the general
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.
The present invention further provides a method of pro- ~
tecting 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 of pro-
tecting a crop area against phytopathogenic 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 com-
prises a compound of the general formula I together with in-
structions for its use for controlling phytopathogenic fungi.
The compounds of the present invention that are
especially distinguished by an outstanding fungicidal action are
those of the general formula I given above in which Rl represents
a hydrogen atom or a methyl or ethyl group and R2 represents a
phenyl, methylphenyl, dimethylphenyl, ethylphenyl, isopropyl-
phenyl, methoxyphenyl, ethoxyphenyl, methylthiophenyl, fluoro-
phenyl, chlorophenyl, bromophenyl, dichlorophenyl, trifluoro-
methylphenyl, nitrophenyl, cyanophenyl, methoxycarbonylphenyl,
acetylphenyl or biphenylyl group.
The new active compounds may be applied singly or,
- 3 -
", /
8~
alternatively, mixtures of at least two constitutionally different
compounds of the general formula I may be applied. If aesired,
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
form of fungicidal preparations, for example powders, strewable
preparations, granules, solutions, emulsions or suspensions,
with the addition of liquid and/or solid vehicles or diluents
and, 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, dioxan, acetonitrile, ethyl acetate,
dimethylformamide, isophorone and dimethyl sulphoxide.
Suitable solid carriers are, for example, lime, 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 of ligninsulphonic acids, salts of 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 fungicidal
preparations may vary within wide limits, the exact concentra-
tion of the active substances used for the preparations being
primarily dependent on the quantity in which the preparations
inter alia are to be used for treating soil or seeds or for
; 30 spraying leaves. The preparations may contain, for example,
.
.~,~
.
approximately 1 to 80% by weight, preferably between 20 and
50~ by weiqht, of active compound(s), approximately 99 to 20~
by weight of liquid or solid carrier and also, if desired, up
to 20~ by 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 I, wherein
a compound of the general formula II .-
(C~2)n- ~H~ R2 (~
l J~o
; ~/ ~o-- ~
. .
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
; solvent with cyclopropanecarboxylic acid chloride of the formula
~ III
; 20
C'l ~ C0 - C~ ¦ (III) O
~H2
The amounts used of the compound of the general formula
II and the compound of the formula III are preferably in
equimolar proportions.
As acid-binding agents there may be used, for example,
organic bases, for example pyridine, triethylamine or N,N-
dimethylaniline, or inorganic bases, for example hydroxides,
: oxides and carbonates of alkali metals and alkaline earth metals,
for example sodium, potassium or calcium.
-- 5
As a solvent that may optionally be used, there may bementioned, for example, ether, 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
temperature within the range of from -10C to 120C.
The products of the process of the present invention may
be isolated in a manner known per se.
Some specific compounds of the present invention are
- 10 listed in the following Table.
- 20
~ 30
-` ~q~16~
Compound Name Physical constant No.
. _ .
1 Cyclopropanecarboxylic acid
[N-(2-oxoperhydro-3-furyl)-
anilide] M.p.: 104C
2 Cyclopropanecarboxylic acid
[2,6-diethyl-N-(2-oxoperhydro-
3-furyl)-anilide] M.p.: 102-103C
3 Cyclopropanecarboxylic acid
[2-methoxy-N-(2-oxoperhydro-
~: 3-furyl)-anilide] M.p.: 175-176C : -
: 4 Cyclopropanecarboxylic acid
[2-methyl-N-(2-oxoperhydro-
3-furyl)-anilide] M.p.: 108-109C
- '
; 5 Cyclopropanecarboxylic acid :~
[2,6-dimethyl-N-(2-oxoperhydro-
3-furyl)-anilide] M.p.: 114-116C :
6 Cyclopropanecarboxylic acid ~::
[2,5-dimethyl-N-(2-oxoperhydro- : :
3-furyl)-anilide] M.p.: 84C
7 Cyclopropanecarboxylic acid
[3-methyl-N-(2-oxoperhydro-
;. 3-furyl)-anilide] M.p.: 109C
8 Cyclopropanecarboxylic acid
: [4-methyl-N-(2-oxoperhydro-
- 3-furyl)-anilide] M.p.: 123C
9 Cyclopropanecarboxylic acid
[3,4-dimethyl-N-(2-oxoperhydro-3-
furyl)-anilide] M.p.: 99-100C
Cyclopropanecarboxylic acid
[2,3-dimethyl-N-(2-oxoperhydro-
3-furyl)-anilide] M.p.: 153C
11 Cyclopropanecarboxylic acid
[2,4-dimethyl-N-(2-oxoperhydro-
3-furyl)-anilide] M.p.: 85-86C
12 Cyclopropanecarboxylic acid
[3,5-dimethyl-N-(2-oxoperhydro-
3-furyl)-anilide] M.p.: 103C
:'
.. ''~ '
13 Cyclopropanecarboxvlic acid
[2,4,6-trimethyl-N-(2-oxoper-
hydro-3-furyl)-anilide] M.p.: 119 - 121C
14 CyclopropanecarboxYlic acid
[4-chloro-N-(2-oxoperhydro-
3-furyl)-anilide] M.p.: 149 - 150C
Cyclopropanecarboxylic acid
[3-chloro-N-(2-oxoperhydro-
3-furyl)-anilide] M.p.: 99 - 100C
16 Cyclopropanecarboxylic acid
[4-isopropyl-N-(2-oxoper-
hydro-3-furyl)-anilide] M.p.: 108 - 110C
. .
17 Cyclopropanecarboxylic acid
[3-trïfluoromethyl-N-(2-oxoper-
hydro-3-furyl)-anilide] M.p.: 104 - 105C
18 Cyclopropanecarboxylic acid
[3-fluoro-N-(2-oxoperhydro-
3-furyl)-anilide] M.p.: 89C
19 Cyclopropanecarboxylic acid
[3-hromo-N-(2-oxoperhydro-3-
furyl)-anilide] M.p: 93 - 94C
: 20 Cyclopropanecarboxylic acid
[2,6-diisopropyl-N-(2-oxoper-
hydro-3-furyl)-anilide] ~1.p.: 215 - 216C
: 21 Cyclopropanecarboxylic acid
[2-ethyl-N-(2-oxoperhydro-
3-furyl)-anilide] M.p.: 103C
22 Cyclopropanecarboxylic acid
[4-ethvl-N-(2-oxoperhYdro-
3-furyl)-anilide] M.p.: 107C
23 Cyclopropanecarboxvlic acid
[4-methoxy-N-(2-oxoperhydro-
3-furyl)-anilide] M.p.: 75C
24 Cyclopropanecarboxylic acid
[4-bromo-N-(2-oxoperhydro-
3-furyl)-anilide] M.p.: 144 - 145C
Cyclopropanecarboxy].ic acid
. . [4-fluoro-N-(2-oxoperhydro-
3-furyl)-anilide] M.p.: 138 - 139C
: 26 Cyclopropanecarboxylic acid
[2-ethoxy-N-(2-oxoperhydro-
: 3-furyl)-anilide] M.p.: 143 - 145C
27 Cyclopropanecarboxyl;c acid
[3-chloro-2-methyl-N-(2-oxoper-
hydro-3-furyl)-anilide] M.p.: 121 - 124C
--7--
3~10831~ -
28 Cyclopropanecarboxylic acid
[5-chloro~2-methyl-N-(2-oxoper-
hydro 3-furyl)~anil~de] M.p.: 114 - 116C
29 Cyclopropanecaxboxylic acid
[4-methoxy-2 methvl-N~(2- 20
oxoperhydro~3-furyl)-anilide] nD = 1.5520
Cyclopropanecarboxylic acid
[4-ethoxy-N-(2-oxoperhydro- 20
3-furyl)-anilide] nD = 1,4579
i~ 31 Cyclopropanecarboxylic acid
[5-chloro-2-methoxy-N-(2-oxo-
perhydro-3-furyl3-anilide] M.p.: 163 - 164C
32 Cyclopropanecarboxylic acid ~-
[3-chloro-N-(5-methyl-2-oxo-
perhydro-3-furyl)-anilide] M.p.: 95 - 97C
33 Cyclopropanecarboxylic acid
[3-ethyl-N-(2-oxoperhydro-
3-furyl)-anilide] M.p.: 69 - 70C
- 34 Cyclopropanecarboxylic acid
[3-cyano-N-(2-oxoperhydro-
3-furyl)-anilide] M.p.: 142 - 143C
Cyclopropanecarboxylic acid
[3-thiomethyl-N-(2-oxoperhvdro- 0
3-furyl)-anilide] nD = 1.5888
36 Cyclopropanecarboxylic acid
[2,3-dichloro-N-(2-oxoperhydro-
` 3-furyl)-anilide] M.p.: 136 - 137C
The compounds of the present invention are ingeneral
almost colourless,odourless,cristalline substances which are prac-
tically insoluble in water and benzine, but, in contrast, are verv
readily soluble in polar organic solvents, for example acetone,
dimethylformamide and dimethyl sulphoxide.
The starting compounds for the manufacture of the com-
pounds of the present invention are known per se or may be produced
; according to processes known per se.
The following Examples illustrate the invention. Example
1 illustrates the manufacture of the compounds of the present
invention and Examples 2 to 9 illustrate the possibilities of
application of the co~pounds ~f the present inyention.
Example 1
.
Cyclopropanecarboxylic acid [~ (2-oxoperhydro-`3-furyl)-anilide]
(Compound No. 1)
6.30 g (0.06 mole) of cyclopropanecarboxylic acid chloride
were added dropwise, at a 5 to 10C internal temperature, while
stirring, to a solution of 10.62 a (0.06 mole) of 3-anilinoper-
hydrofuran-2-one in 50 ml of pyridine. The mixture was then
stirred for 1/2 hour at room temperature and then poured on to
200 a of water/ice and stirred well. After filtering with suction,
the mixture was carefully washed with water and dried in a drying
cupboard.
Yield: 10.25g = 70~ of the theoretical yield; m.p.: 104C.
Each of the other compounds of the present invention
listed in the Tahle above may be produced in an analogous manner.
Example 2 -
Limiting concentration test in the control of Py*hium ultimum
_.
In a series of tests 20~ pulverulent active substance
preparations were mixed uniformlv with soil which was severely
infected with P~thium ultimum. The treated soil was placed in
clay dishes each having a capacity of 0.5 litre and, without
a waiting period, 20 marrowfat peas of the "Xelvedon Wonder"
variety were sown in each dish. ~fter a cultivation period of
three weeks at 20 to 24C the number of healthy peas was
determined and an assessment (1 - 4 as defined below) of the roots
was carried out.
The active substances used and their application ~uan-
tities, and also the results, are given in the following Table.
g _
Active substance Num~er of Root
Compound according to concentration in healthy assessment
the invention mg/l soil _peas (1 - 4)
Cyclopropanecarboxvlic 10 17 4
acid [N-(2-oxoperhydro- 20 17 4
3-furyl)-anilide] 40 18 4
Cyclopropanecarboxylic 10 16 4 ~ ,~
: acid [2~6-dimethyl-N- 20 20 4
(2-oxoperhydro-3~furyl)- 40 19 4
anilide]
Cyclopropanecarboxylic 10 19 4 ~: -
acid [3-chloro-N-(2-oxo- 20 17 4
perhydro-3-furyl)-anilide] 40 17 4
Cyclopropanecarboxylic 10 10
10 acid [3-methyl-N-(2-oxo- 20 16 2 -:
perhydro-3-furyl)-anilide] 40 16 4
Cyclopropanecarboxylic 10 10
acid [2-methoxy-N-(2-oxo- 20 16 2
perhydro-3-furyl)-anilide] 40 20 4
Agent for comparison `
5-Ethoxy-3-trichloro- 10 2
methyl-1,2,4-thiadiazole 20 5
12 3
Control I
. . .
(3 repetitions) a) 1 1-
Infected soil b) 0
c ) O
Control II
20 (3 repetitions) a) 19 4
Steamed soil b) 18 4
c) , ,18 4
Root assessment: 4 = white roots without fungal necroses;
3 = whi.te roots, slight fungal necroses;
2 = brown roots, considerably severe fungal
necroses;
, 1 = severe fungal necroses, mouldy roots.
Example_3
. .
Dress.inq o`f su'~'arbeet
. _ _
In a series of tests graded sugarbeet seeds of the variety
"Dieckmann Suprapolyl' were dressed with-20% pulverulent active
substance prepar~tions~ Clay dishes each of 2 litres capacity
-- 10 --
~ ~ .
:; : : . .
(20 x 20 x 5 cm) were filled with normal compost soil (damping-
off) and 100 of the sugarbeet seeds were sown in each dish .
After a cultivation period of 18 days at 19 to 21C in a green-
house the numker of healthy seedlings was determined.
The active substances used and their application quan-
tities, and also the results, are given in the following Table.
''' . .
. .
' ` '
X
Compound according to Active substance # of healthy
the invention in g/ka seed seedlings from
lOO.seeds
.. . .
Cyclopropanecarboxylic acid 0.4 79
[N-(2-oxoperhydro-3-furyl)- 0.8 79
anilide] 1.6 75
Cyclopropanecarhoxylic acid 0.4 70
[2,6-dimethyl-N-(2-oxoper- 0.8 76
hydro-3-furyl)-anilide] 1.6 83
Cyclopropanecarboxylic acid 0.4 83
[3-chloro-N-(2-oxoperhydro- 0.8 82
3-furyl)-anilide] 1.6 93
Cyclopropanecarboxylic acid 0.4 77
10 [3-methyl~N-(2-oxoperhvdro- 0.8 71
3-furyl)-anilide] 1.6 85
Cyclopropanecarboxylic acid 0.4 83
[2-methoxy-N-(2-oxoperhydro- 0.8 87
3-furyl)-anilide] 1.6 87
Agents for comparison
5-Ethoxy-3-trichloromethyl- 0.4 26
1,2,4-thiadiazole 0.8 44
1.6 53
: Tetramethyl.thiuram 4.8 21
disulphide 9.6 50
: Control I
(3 repetitions) a) 5
Infected soil b) 7
c) 6
Control II
t3 repetitions) a) 83
Steamed soil b) 86
c) 81
- 12 -
1~ 6~ - -
Example 4
Ef fect of prophylatic leaf treatment against Plasmopara
viticola on vines in a greenhouse
In a series of testsvoung vines having approximately 5
to 8 leaves were sprayed until dripping wet with the concentration
of active substance indicated in the Table below and, after the
spray coating had dried on, were sprayed on the undersides of the
leaves with an aqueous suspension of sporangia of the fungus indi-
cated in the heading above (approximately 20,000 per ml), and
immediately incubated in a greenhouse at 22 to 24C in an atmos-
phere as saturated with water vapour as possihle. From the second
day onwards, the air humidity was reduced to the normal level for
3 to 4 days (approximately 30 to 70% saturation) and then maintained
at water vapour saturation for a further day. The percentage
proportion of the surface attacked hy fungi of each leaf was then
recorded and the average per treatment was calculated as follows
to determine the fungicidal effect:
100 - `100 x attack in treated plants = % effect
. .
attack in untreated Plants
: 30
- 13 -
Compound .csording to the %Effect ~qainst Concentration
invention Plasmopara (%active
vit~co~a ~) substance)
Cyclopropanecarboxylic acid
[2,6-diethyl-N-(2-oxoper-
hydro-3-furyl)-anilide] 40 0.025
Cyclopropanecarboxylic acid
[3-fluoro-N-(2-oxoperhydro-
3-furyl)-anilide] 100 0.025
Cyclopropanecarboxylic acid
[3-bromo-N-(2-oxoperhydro-
3-furyl)-anilide] 100 0.025
Cyclopropanecarboxylic acid
[2,6-diisopropyl-N-(2-oxoper-
hydro-3-furyl)-anilide] 84 0.025
Cyclopropanecarboxylic acid
[2-ethyl-N-(2-oxoperhydro-3-
furyl)-anilide] 83 0.025
Cyclopropanecarboxylic acid
[4-ethyl-N-(2-oxoperhydro-
3-furyl)-anilide] 40 0~025
Cyclopropanecarboxylic acid
[4-fluoro-N-(2-oxoperhydro-
3-furyl)-anilide] 100 0.025
Cyclopropanecarboxylic acid
[2-ethoxy-N-(2-oxoperhydro-
3-furyl)-anilide] 70 0.025
Cyclopropanecarboxylic acid
[3-chloro-2-methyl-N-(2-oxoper-
hydro-3-furyl)-anilide] 98 0.025
Cyclopropanecarboxylic acid
[3-ethyl-N-(2-oxoperhydro-
3-furyl)-anilide] . 100 0.025
Cyclopropanecarboxylic.acid .
[3-cyano-N-(2-oxoperhydro-
3-furyl)-anilide] 100 0.025
Cyclopropanecarboxylic acid
~3-thiomethyl-N-(2-oxoper-
hydro-3-furyl)-anilide] 70 0.025
Cyclopropanecarhoxylic acid
[2,3-dichloro-N-(2-oxoperhydro-
3-furyl)-anilide] 100 0.025
Cyclopropanecarbox~tl;c acid
[N-(2--oxoperhydro 3-furyl)-
anilide] 100 0.001
Cyclopropanecarboxylic acid
13-chloro-N-(2-oxoperhydro-
3-furyl)-anilide] 100 0.001
~.-- .
~ - 14 -
+) Effect was calculated on 100% attack in the untreated control.
Example 5
-
Effect of prophylactic leaf treatment against Phytophthora
infestans in tomato plants or p.otato plants in .a greenhouse
In a series of tests younq tomato plants having at least
two developed foliage 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 Table
below and, after the spray coatinq had driedon, were sprayed with
10 an aqueous suspension which contained per millilitre 50,000 to
80,000 sporangia of the fungus indicated in the heading above and
which had been incubated in a refrigerator at 11C for approximately
2 hours. The plants were incubated at a high level of air humidity
and at approximately 15 to 18C in a greenhouse and, after approxi-
mately 5 days, the percentaae proportion of leaf surface that had
been attackefl was assessed. The fungicidal effect was calculated
as follows:
100 = 100 x attack in treated plants = ~ effect
attack in untreated plants
~ Effect against Phytophthora infestansin potatoes +)
Compound accordinq to the Concentration (~
invention active substance )
_. _ __ 0.005
Cyclopropanecarboxylic acid
[N-(2-oxoperhydro-3-furyl)-
anilide] - 95
Cyclopropanecarboxylic acid
[2,6-dimethyl-N-(2-oxoperhydro-
3-furyl)-anilide] 80
?~
, - 15 -
Agent for comparison
~anganese ethylene bisd~thio-
carbamate 50
%Effect against Phytophthora infestans in tomatoes.+)
_ _ .
~ompound accordina to the Concentration (%
invention active substance)
. 0.005
-
Cyclopropanecarboxvlic acid
[N-(2-oxoperhydro-3-furyl)-
anilide] 100
Cyclopropanecarboxylic acid
[3-methyl-N-(2~oxoperhydro-3-
10 furyl)-anilide] 81
Cyclopropanecarboxylic acid
[3-chloro-N-(2-oxoperhydro-3-
furyl)-anilide] 91
Agent for com~arison
-
Manaanese ethylene bisdithio-
carbamate 67
: +) Effect was calculated on 100% attack in the untreated control
: Example 6
Systemic effect of soil treatment against Phytophthora
infestans in tomato p.lants o.r potatoplants in a areenhouse
..... _
: 20 In a series of tests the substances to be tested, which
had been weighed out (weiqht be volume), were mixed with arable
soil which was then placed in plant pots, and young tomato
plants having at least two developed foliage leaves and potato
plants (for example from eye cuttings) at least 10 cm tall were
placed in these pots. After the desired pre-dose time (for
.. example after 4 or 18 days? had expired, the plants were sprayed
with an aqueous suspension which contained per millilitre S0,000
~ to 80,000 sporangia of the fungus indicated in the heading above
.. and which had been incubated in a refrigerator at 11C for
approximately 2 hours. The plants were incubated at a high
- 16 -
~81~1
level of air humidity and at approximately 15 to 18C in a
greenhouse and, aEter approximately 5 days, the percentage pro-
portion of leaf surface that had been attacked was assessed.
l'he fungicidal effect was calculated as follows;
100 - 100 x attack in treated plants = % effect
attack in ~ntreated plants
Systemic effect of soil treatment against Phytophthora infestans
10in tomato plants
Compound according to tne ppm active ~ Effect 4 +) of treatment
invention substance days before 18 days before
inoculation inoculation
.. . .. . . ... ... .. _ . _ .
Cyclopropanecarboxylic acid 25 89 85
[N-(2-oxoperhydro-3-furyl)-5 70 39
anilide]
Cyclopropanecarboxylic acid 25 92 82
[2,6-dimethyl-I~-(2-oxoper-5 40 71
hydro-3-furyl)-anilide]
+) Effect was calculated on 100% attack in the untreated control
~0
; Example 7
Curative effect of leaf treatment against Phytophthora infestans
in tomato plants or potato plants in a greenhouse
, In a series of tests young tomato plants having at
least two developed foliage leaves or potato plants (for example
from eye cuttings) at least 10 cm tall were sprayed with an aqueous
suspension which contained per millilitre 50,000 to 80,000
sporangia of the fungus indicated in the heading above and which
had been incubated in a refrigerator at 11C for approximately
2 hours. The plants were incubated at a high level of air
humidity. After the desired pre-dose time had expired, the
plants were sprayed until dripping wet, within the period of
- 17 -
8~
latent fungal attack, with the concentration to be tested of
the fungicide indicated in the Table below. After the outbreak
of fungal attack in the untreated control plants the percentage
proportion of leaf surface that had been attacked was assessed.
The fungicidal effect was calculated as follows:
100 - 100 x attàck in treated plants = % effect
... .
attack in untreated plants
.
Compound according to the ~ Active % Effect +) of treat-
invention substance before ment 1 day
sprayed inoculation after
inoculation
.. .. . _ _
Cyclopropanecarboxylic acid
[~-(2-oxoperhydro-3-furyl)-
anilide] 0.004 100 68
Cyclopropanecarboxylic acid
[2,6-dimethyl-N-(2-oxoper-
hydro-3-furyl)-anilide] 0.004 100 60
Agent for comparison
Manganese ethylene bisdithio-
carbamate 0.004 91 0
+) Effect was calculated on 100~ attack in the untreated control
Example 8
Effect of treatment of barley grains against helminthosporium
spec.
In a series of tests barley grains that had been
attacked by helmintilosporium spec. were treated with S0 mg of
.....
active substance per 100 g of grains. rrhe grains were then SOWII
in soil and incubated in an air-conditioned chamber at +1~C.
Tile tests were evaluated after 6 weeks and tile rexulting seed-
lings exnibited a markedly reduced attack as compared with plantsof an untreated control group.
- 18 -
lhe results are given in the following Table.
Compound according to the % Effect
invention
. .
Cyclopropanecar~oxylic acid
[4-metllyl-N-(2-oxoperllydro-
3-furyl)-anilide] 40
Cyclopropanecarboxylic acid
[~,4-dimethyl-N-(2-oxoper-
hydro-3-furyl)-anilide] : ~ 40
Cyclopropanecarboxylic acid
[4-ethyl-1~-(2-oxoperhydro-
3-furyl)-anilide] 40
Untreated control o
~xample_
Limiting concentration test in the control of Pythium ultimum
In a series of tests 20~ pulverulent active substance
preparations were mixed uniformly with soil 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 peas (Pisum sativum L. convar.
medullare Alev.) of the "Kelvedon Wonder" variety were sown in
each dish. After a cultivation period of 3 wee]cs at 20 to 40C
the number of healtlly peas was determined and an assessment
(1 - 4 as defined below) of the roots was carried out.
The active substances used and their application
cluantities, and also the results, are given in the following
Table.
-- 19 --
