Note: Descriptions are shown in the official language in which they were submitted.
The pre~ent invention provides compounds o the formula I
R$~ R4 ~I)
wherein ~1 represents alkyl of l to 4 carbon atoms, alkoxy of
1 t~ 4 carbon ~toms or hal~gen, R2 repre~en~s hydrogen, alkyl
of 1 to 3 carbon at~ms or halogen, ~5 repre~ent8 hydrogen,
fll~l o 1 to 3 carbon atoms or halogen, R~ represents hydro-
gen or methyl, the total number o carbon a~oms o~ the subs~
tu~nt~ Rl, R~, R5 ~nd R6 in the phenyl ring not e~ceeding 8,
X represents -CH2 or C~U3 R~ r~pr~sent~ ~ COOR' or
-CON~ , w~e~e~n each of ~',, R" and R'~ r~pre~en~s hydro-
. .
gen, me~hyl -o~ ethyl, and R4 repre~ents an unsubstituted or a
methyl- andLor halogen-substituted furane 7 tetrahydrofurane,
th~ophene, pyridine, pyrimidin, 2,3-dihydro-4H-pyrane or
l,4-oxa~hi (2)-ine radical with the proviso th~t the phenyl ring
contains a ~urther substituent if it is substi~uted in 2,6-
or in 2,3,6-position by methyl and if at ~he same time R4
represent~ the 2-furanyl radical and -X-R3 represents the
a-propionic acid methyl ester. The invention also provides
a process for the manuEacture of these compounds as well as
compo~itlons whLch contain these compounds as active
,
, -
- , : , ' , ,
, : , , , ~ , . ... . . . .
. . , . , , . - , ..
' - ' , '" "' '1, ' ~ ; ;
,. . . . . . . . .
, ' ,
~s~s~
substances, and a method of using these active substances as
microbicidal agents.
By alkyl and alkyl moiety of an alkoxy group are meant the
following groups, depending on the number of carbon atoms
speciEied: methyl, ethyl, n-propyl, isopropyl or n-, iso-,
sec.- or tert.butyl. Halogen is fluorine, chlorine, bromine or
iodine.
PreEerred as R4 are e.g. the 2-furanyl, 2-tetrahydro~uranyl,
5-bromo-2-furanyl or 5-bromo-2-tetrahydrofuranyl radicals.
German Ofenlegungsschrift 2'006'471 teaches (2'-methylfur-
anyl~3')-carbonyl~2,6-dimethylaniline and (2' methylfuranyl)-
3')-carbonyl-2-methyl-6-chloroaniline as active substances
with moderate action against certain fungi (Uromyces phaseoli,
Alternaria solani, Rhizoctonia solani).
This invantion is based on the surprising observation that
compounds with the markedly different structure of the formula
I havé what ls for practical purposes a very useful micro-
bicidal ~pectrum for proterting cuLtivated plants. Examples
o~ cultivated plants within the s ope of this invention are:
cereals, maize, rice, vegetabLes, sugar b~et, soya, ground
nuts, ruit trees, ornamental plants, but primarily vines,
~'~
~.
~: ' . ' . : ,.,. , ' .
.
..
.
,
hops, cucumber plant~ (cucumbers, m~Lrrows 7 melons), solana-
ceae, such as potatoes 9 ~obacco and tomatoes 7 as well as
bananA~, ocoa and na~ural rubber plants.
~th the active ~ubstances of the formula I it is possible to
inhlbl~ or des~ro~ the fungi which occur in plan~s or parts
o plan~ (fruit, blossoms, leaves, stems~ ~ubers 7 roo~s) of
these and rela~ed cultures of use~ul plan~s and also to pro-
tec~ ~rom ~uch fungi ~he parts of planks which grow la~er.
The ~ctlv~ substances ac~ against the phy~opathogenie fungi
wh~ch beltmg to the following clas~es: ~scomycetes (e.g, ery-
siphaceae); ba~idiomycete~, above all rust fungi; fungi imper-
ectl but eepec~lly ~in~t ~c~yc2~e~ wh~ch belon~ to ~hc
¢1~ a~ phycomycekes, e.g. phyt:o~hthora, peronosporn, p~eudo-
p~rono~p~ra~ py~hium or plasmopaLra. In aLddition, the compounds
o~ t~e ~o ~ula I have a sys~emic ac~ion~ They can also be used
a8 ~eed~dre~sing agen~ for protecting seeds (fruit, ~ubers,
kernels~ ~nd pl~nt cuttings rom fungus inections as well as
~rom phy~opathogenic fungi which occur in ~he soil.
Pre~erred microb~cides are compounds of the formula I wherein
~1 reprasents me~h~l9 R2 is in ortho-position to the amino
group and reprQ~Qn~s methyl, e~hyl or chlorine, -X-R3 is
he ~ro~p 7H3 ~ and ~4, R5 , Rh ~nd R' have the meanings
~CH-COOR'
revlously assigned to them. These c~mpound9 will be referred
- 4 -
. ., . ~ .
,
.
~ ~5~5 ~6to as group Ia. Preeminent amoung thesecompounds Ia are those
wherein R4 represents the 2-furanyl radical which is optionally
substituted by a methyl group but which is preferably
unsubstituted.
Within this last mentioned group, especial importance attaches
to microbicldal compounds w~erein -X-R3 represents the a-pro-
pLonic acid methyl ester group and wherein the total number
of carbon atoms of the substituents Rl, R2, R5 and R6 does not
exceed 4, for example the 2,3,5,6 tetramethylaniline, 2,6-
dimethyl-3-ethylaniline or 2,6-dimethylaniline derivatives as
well as tho~e 2,6-dimethylaniline derivatives which contain
in addi~ion a thlrd substituent R5 or R6 in the phenyL
nucleus. The group Ia includes as fu~ther microbicidal group
which is of interest in particular fields those compounds
wherein R4 represents a 3-~ur~nyl radical which may be
substit~ted by one or two methyl groups. Those compounds of
the g~oup Ia in which R4 is 2 thienyl are also particularly
interesting microbicides.
_ 5 _
.,,.~,.
.. , . .; . ,, , ., ~, , . ,, .,.. , ., . . ~ :. - . .
. - :. . ,, : . .
., ,: , .. , . . ,: : : . ,. : :
.
.
. : .
, - , , , . .: . . .. .
"
~. . . . . .
,: . .. . . ..
., , .. ,. : ~........ ..
The compounds o~ the formula I are mantlfactured according to
the invention by acylating a compourld of ~he formula II
R5 ,~ ~ X - R3
.
wL~h ~ c~bo~cylie ~cid of the onnul~ III
HO-CO-R~, (III)
o~ wi~h the acid halide9 acid anhydride or es~er thereof, in
isola~ed ~nstances also with one of the acid amides thereo~
~:rRnsamid~tlon).
Accordin,g to another method of ~he invention, it is a~L~o pos-
sible t~ manu~actu~e the compounds of the formllla I by con~
te~tin~ the acyl anilide of the formula IY
R5,~,~111-CO-R4 (IV)
..
6-
.. . .. . . .
: - , ,; . .
: , , , ,, ~ , ,
: . . , . : : . . ,
, , ,. : ,,: . ,
., " . , ~ .
,
~ O ~ 5 ~
with butyl lithium or sodi~m hydride into the corresponding
alkali salt, which ls then reacted with a compound of the
formula V
Hal-X~R3 (V)
to give the desired end product9 or ~lse to re~ct the acyl anl-
lide of ehe ormula IV with the compound of the fonmula V in
~he presence of an alkali carbona~e (e.g, Na2C03 or K2C03~
as pro~on accep~or, preferably with the addition of ca~alytic
amoun~s of alkali i~odide (e.g. potassium iodide).
In ~he forrnulae II, III, IV and V, the symbols Rl ~o R6 and
X have the meanings assigned ~o them in formula I and Hal re-
pr~ents ~ h~logen ~tom ~ preferably chlorine or bromine, or
~nother easily remov~ble r~dica:l, ~e ~erm "~cid halld~ c~ln
preferably ~he acid chloride or acid bromide.
The reactions can be carrled out in ~he presence o absence
o olvents or diluents ~hich are ~nert to ~he reactants.
Examples o~ such solvents or di]Luents are; aliphatic or aro-
matLc hydrocarbons, e~g. benzene, toluene, xylene, petroleum
e~her; halogenated hydrocarbon~, e.g, chlorobenzene,me~hylene
chloride, ethylene chloride, chloroorm; ethers and ethereal
compounds such ~s dialkyl ethers, dioxan 3 tetrahydrouran;
nitrile8 like acetonitrile; N,N-dialkylated amides llke di-
methyl orm~mide; anhydrous acetic acid, dimethyl sulphoxide;
ketones like methyl ethyl ketone and mixture~ o~ such solvents.
~ 7 -
,, . .. , . . . . . ,., .. . -
' ' , ~ ' ' ', . , '' , ' . ' '
~s~
The reaction temperatures are between 0 and 180C, preferably
between 20 and 120C. In many cases it is advantageous to
use acceptors or condensation agents. Suitable examples are:
tertiary amines, e.g. trialkylamines (e.g. triethylamine), py-
ridine and pyrldine bases, e.g. the oxides and hydroxides,
hydrogen carbonates and carbonates of alkali metals and alk-
aline earth metals, as well as sodium acetate. Furthermore, it
is alsio possible to use a surplus of the respective aniline
derivative of the formula II as acid acceptor in the first
method,
The process of manufacture which proceeds from compounds of
the formula II can also be carried out without acid acceptors;
in some instances it is expedient to pass in nitrogen in
order to expel the hydrogen halide that has formed. In other
instances, it is very advantageous to use dimethyl formamide
as reaction catalyst.
Particulars on the manufacture of the intermediates of the
~ormula II can be inferred from the methods which are generally
indicated for ~he manufacture of anilino-alkane acid ester in
the following publications: J. Org. Chem. 30,4101 (1965),
Tetrahedron 1967, 487, Tetrahedron 1967, 493~
CH3
The compo~mds of the formula I in which X = -~CH- possess an
asymmetrical carbonatom (*) and can be resolved into the op~i-
cal antipodes in the customary manner In this connection, the
enantiomeric D-form has the more pronounced microbicidal action.
:. , , .: i . .: , ~ , .. : .
~ O ~ 5~ ~
Within the scope of the invention, those compounds~ their
agents and their use whi~h refer to the D-configuration of the
formula I are accordingly preferred. In ethanol or acetone
these D-forms have,as a rule a negat;ve angle of rotation.
Thie pure, optical D-antipodes are obtained by manufacturing
the racemic compound of the formula VI
R5 - 1 CH3
6 ~ NH-CH~COOH (VI)
,
wherein Rl, R2, R5 and R6 have the meanings assigned to them
in formula I, and then reacting t:his in known manner with a
nitrogen-containing, optically ac:tive base to give the corres-
ponding salt. The pure D-form is obtained stepwise by frac~iona-l
crystallisation of the salt and subsequent liberation of the
acid of the formula Vl which is enriched with the op~ical D-
antipode and, if appropriate, repeating (also several timesj
the salt formation, crystallisation and liberation of the ~- ~
anilinopropionic acid of the formula VI. From this D-form it ;
is then possible, if desired, to manufa¢ture the optical D-con- ;
figuration of the ester of the formula IX in conventional
manner, e.g. in the presence of HCl or H2S04, with methanol or
ethanol, or to manufacture the amide of the formula II with
the corresponding amine of the formula HN(R")(R"'). A suitable
_ 9 _ .
'
, ' ' ' ;' ' ~ ' ' ' ~ ' ~ . ,
~ 5~5~6
optica]ly active organic base is, for example~ ~-phenylethyl-
amine.
Instead of fractional crystallisation, it is also possible to
obtain the enantiomeric D-form o the formula VI by replacing
the hydroxy group in the naturally occurring L(~)lactic acid
by halogen and reacting this product further with the desired
aniline o-f the formula VII
~ ~ ~VII)
with reversal of the configuration.
Besides the optical isomerism, an atropisomerism i5 normally
observed about the phenyl N ~ ax;s in those cases where
the phenyl ring is substituted at least in 2,6~-position and
at the same time unsymmetrically to this axis (i.e. also by
the presence of additional subst:ituents as the case may be).
This feature is caused by the steric hindrance of the radicals
-X-R3 and -CO-~. Provided no syn,~hesis is carried out
with the aim of isolating pure isomers, a product normally
occurs as a mixture of two optical isomers or of two atropiso-
mers or as a mixture of these four possible isomers. The
basically better fungicidal action of the enantiomeric D-form
(in compar-Lson to the D,L-form or to the L~form) is retained
-
- 10 -
;. - - - - :
,. . . .
~,' ' I ' ''' ,
1~ 5~ 5~
however and is not noticeably affected by the atropisomerism.
The following Examples illustrate the invention in more detail
but do not limit it to what is described therein. Unless
otherwise stated, an active substance of the formula I, which
can occur in optically active forms,is always the racemic
mixture~
,. , . : :
.
~5~S~à
E:xample
C~l
3 / ~H - COOCH3
Manafacture of ~ O ~ ~l (compound 2)
O
N~ methoxycarbonyl-ethyl~-N-(furan-(2")-carbonyl) 2,3-di-
methyl-6-ethylaniline.
a) 100 g of 2,3-dimethyl-6-ethylaniline, 223 g of 2- ; -
bromopropionic acid methyl ester and 84 g of NaHC03
were stirred for 17 h~ours at 140C. Ihe m;xture
, was then cooled, diluted with 300 ml of water and
extrac~ion was performed wit~ diethyl ether. The
extract was washed with a small amount of water,
dried over sodium sulphate, filtered, and the ether
evaporated off. After the surplus 2-brsmopropionic
acid methylester had been distilled off, the crude - .
product was distilled in a high vacuum; b.p. 88a-
90C/0.04 Torr.
b~ 13 g o~ furan-2-carboxylic acid chloride were added
dropwise with stirring to 17 g of the ester obtained
.
. - 12 -
. : . .. , . .: ..
s ., ~ , , . . ~ . ;
~ S~ ~6
in a), 2 ml of dimethyl formamide and 150 ml of
absolute toluene and the mixture was refluxed for
1 hour. The solvent was evaporated off and the
crude product was then crystallised by trituration
with petroleum ether; m.p. 110.5-126C (ethyl
acetate/petroleum ether). Compound 2 is the mix-
ture of two pairs of diastereoisomers.
The D-forms of both atropisomers (compounds 2a and 2b) are ob-
tained by acylating the D-form of ~-(2,3-dimethyl-6-ethylani-
lino)-propionic acid methyl ester with furan-(2)-carbo~ylic
acid or one of the reactive derivatives thereof. --~
. ~
. .
. .
- 13 -
,
':
:,.,, ., -,. ., , , ... , . .,. .: " . ,,, ,.. ~.:: , ,,: ,.. . .. . . . . ..
";, : :,~ ,, , , , ,,, . . .:, " :, ,:, " . , .:, . :.. :: ,. ::: , . . , ,. ::
.,, , j ,, ,: , . . .. , , , ., ,,, i .. , ., ., , , , . . ., ., ., , ,. . .. .: , :, . . . . .. .
-
5~
Example 2
Manufacture of
3 f H2CN \
(compound 47)
~ CH ~ C ~ O ~
N-(dimethylaminocarbonylmethyl)-N-~furan-(2")-carbonyl)-2,6-
dimethylaniline.
28 g of the N~ '-methoxycarbonyl-methyl)-N-(furan-(2'l)-carbonyl)-
2,6~dimethylaniline manufactured analogously to Example 1
(m.p. 98-99C) are stirred for l day at room temperature with
150 ml of 40% aqueous dimethylamine solution and 0.5 g of ~ri-
ethylenediamine.
Unreacted starting material is removed by performing extraction
twice with ether and the aqueous ph~se is then concentrated by
rotary evaporation. The residual viscous oil is crystallised
by trituration with hexane.
The end product has a melting point of 142-145C af~er recry-
stallisation from hexane/tetrahydrofuran.
1~ .
,
. . . . . .. .... . . .. . . . ..
, .. , . . . . . . , .... . ~ ... . . .
., . , . , , , : .- , . ~, :
... ,. , ., , . . , , . . ,~ ~
Example 3
Manufacture of
CH3
CH3 CH~COOCH3
Cl (compo~d 114)
C~3 ~ ~ ~ Cl
N~ methoxycarbonylethyl)-N~(2",4"-dichloropyrimidine-(5")-
carbonyl)-2,6-dimethylaniline.
With stirring, 25.4 g of 2,4-dichloropyrimidine-5-carboxylic
acid chloride in SO ml of chlorobenzene were added dropwise
within 2~ minutes to a mixture of 20.7 g of N-(l'-met'noxycar-
bonylethyl)-2,6-dimethylaniline, 2 ml of dimethyl formamide
~nd lSO ml of chlorobenzene, in the process of which the tem
perature roi~e by 10C. The reaction mixture was then heated
to 110C and the hydrogen chloride which had formed was re-
moved by passing in nitrogen. The solvent was evaporated off
by rotary evaporation and the crude product was then crys~al-
lised by trituration with petroleum ether. The end product
which was purified by recrystallisation from isopropanol had a
melting point of 136-137C. The following compounds of the
formula Ib (Rl = 2-position) whLch are tri or tetra-substi-
'
- 15 - ' .':'
. , ' ~ '
,. .. . . . .. .. ...... . . . . . . .
,, , ~, , ; ;
... . , , , .,, . .. ~.
: i .
~ L~5~5~
s~uted in the phenyl nucleus are manufactured in this manner
or by one of the methods indicated hereinabove. -
R7 R
/
R9 '``8 ~ (Ib)
- 16 - .
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- 19 -
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16
The compounds listed hereinafter are mono- o~ disubstituted
in the phenyl nucleus. They include compounds of the formula
~ 1 - ~ / R3
R2 ~3
: '
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- 22 -
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- 24 -
.,
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Classed among these are also the compounds of the
formula
2 \ C~
~'..,
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Classed among these are also c~mpounds of the formula
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Also the compounds of the general formula:
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- 37 -
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The compounds of the formula I can be used by themselves or
together with suitable carriers and/or other additives, Suit-
able carriers and additi~es can be solid or liquid and corres-
pond to the customary substances used in formulation techno-
logy, for example natural or regenerated mineral substances,
solvents, dispersants~ wetting agents, stickers, thickeners,
binders or fertilisers. The amount of active substance in .
commercially useful compositions is between 3.1 and 90%.
The compounds of the formula I can be applied in the follc-
wing process forms (the percentages by weight in brackets
denote the advantageous amounts of active substance):
solid forms: dusts and tracking agents (up to 10%); granules,
coated granules,
impregnated granules and homogeneous granules :
~l to 80%);
liquid forms:
a) active substance concentrates which are dispersible in
water:
wettable powders and pastes (25-90% in the commercial .
pack, 0.01 to 15% in ready for use solution);
emulsion concentrates and concen~rated solutions (10 to
50%; 0.01 to 15% in ready for use solution);
b) solutions (0.1 ~o 20%).
The active substances of the formula I can be formulated, :~
for example, as follows:
- 38 - ~;
~''""i,' . ' , ' ,;' :.' , "
~ S~ 5~ ~
Dusts: The following substances are used to manufacture a)
a 50% and b) a 2% dust:
a) 5 parts of active subs~ance
95 parts of talcum;
b) 2 parts of active substance
1 part of highly disperse silieic acid
97 parts of talcum.
The aetive substances are mixed with the carriers and ground
and in this form ean be proeessed to dusts for application.
Granules: The following substances are used to manufaeture
5% granules:
5 parts of aetive substance
0.25 part of epiehlorohydrin
0,25 part of cetyl polyglycol ether
3.50 parts of polyethylene glyeol
91 parts of kaolin (partiele size 0.3 - 0~8 mm).
me aetive substanee is mixed wi~h the epiehlorohydrin and the
mixture is dissolved in 6 parts of aeetone. Then polyethylene
glyeol and eetyl polyglyeol ether are added. Ihe resultant -
solution is sprayed on kaolin and the aee~one is evaporated
in vaeuo. Sueh miero granules are advantageously used for eom-
bating soil fungi.
Wettable powders: The following eonstituents are used to
manufaeture a) a 70% b) a 40%, e) and d) a 25% and e) a 10%
wettable powder:
.
- 39 -
,, ~
' ' ' ' ':: ' . .
. .
~, . . . . . . .
54~6
a)70 parts of active substance
5 parts of sodi~n dibutyl naphthylsulphonate
3 parts of naphthalenesulphonic acid/phenolsulphonic
acid/formaldehyde condensate (3:2:1)
10 par~s of kaolin
12 parts of Champagne chalk
b)40 parts of active substance
5 parts of sodium lignin sulphonate
1 part of sodium dibuty]naphthalenesulphonic acid
54 parts of silicic acid
cj 25.parts of active s~bstance . : .
4.5 parts of calcium ligr.in sulphonate
1.9 parts of a Champagne chalk/hydroxyethyl cellulose
mixture (1:1)
1.5 parts of sodium dibut:ylnaphthalenesulphonate
19.5 parts of silicic acidl :
19.5 parts of Champagne chalk
28.1 parts of kaolin
d)25 parts of active substance
2.5 parts of isooctylphenoxy-polyethylene-ethanol :~.
1.7 parts of a Champagne chalk/hydroxyethyl cellulose
mixture (1:1)
8.3 par~s of sodium alumlnium silicate
16.3 parts of kieselguhr
- 40 -
., ,, . . ,;.. , ~ -. , . . ,.-. , ,, i.; .:
;, " ~, ~ , . . . ... .. . .
; .~.,, ", , : ., ,: :
:: , . ,,, ,, ~. .. . . . . . ......
:~ . . ,
46 parts of kaolin
e) 10 parts of active substance
3 parts of a mixture of the sodium salts of sa-
turated fatty alcohol sulphates
5 parts of naphthalenesulphonic acid/formaldehyde
condensate
82 parts of kaolin.
The active substances are intimately mixed in suitable mixers
with the additives and ground in appropriate mills and roolers.
Wettable powders of excellent wettability and suspension pcwer
are obtained. These wettable powders can be diluted with water
to give suspensions of every desired concentration and can ke
used in particular for application to leaves.
Emulsifiable concentrates: The iollowing substances are used
to manufacture a 25% emulsifiable concentrate:
25 parts of active substance
2,5 parts of epoxidised vegetable oil
10 parts of an alkylarylsulphonate/fatty alcohol
polyglycol ether mixture
5 parts of dimethyl formamide
57.5 parts of xylene
By diluting such concentrates with water it is possible to
.. .
manufacture emulsions of every desired concentration which -~
are especially suitable for application to leaves.
- 41
Example 4
Action against Phytophthora infestans on Solanum lycopersicum
(tomatoes).
Ia) Residual preventive action
Solanum lycopersicum plants of the "Roter Gnom" variety
are infect.ed when 3 weeds old with a zoospore suspension of
Phytophthora infestans after they have been sprayed with a
broth prepared from the active substance processed to a we~t-
able powder and containing 0.05% of active su~s~ance, and
dried, They are then kept for 6 days in a climatic chamber
at 18 to 20~C and high humidity, which is produced with an
artificial wet fog. After this time typical leaf specks ap-
pear. Their number and si2e are the criterion for evaluating
the tested substance.
Ib) Curative action
"Ro~er Gnoml' tomato plants are sprayed when 3 weeks old
with a zoospore suspension of the fungus ~nd incubated in a
climatic chamber at 18 to 20C and saturated humidity. The
humidifying is inter}upted aiter 24 hours. After the plants
have been dried, they are sprayed with a broth which contains
the active substance formulated as wettable powder in a con-
centration of 0.05 %. After the spray coating has dried, the
plants are again kept in the humid chamber or 4 days. Size
.,
42 -
, " . ,
, - .' , - .
" '~' , ': ' ' :; ' , , :
~ 5q~5~6
and number of the typical leaf specks which have occurred
during this time are the criterion for evaluating the effec-
tiveness of the tested substances.
II) Preventive-systemic ac~ion
The active substance is applied as wettable powder in a
concentration of 0.05% (referred to the volume of the soil) to
the surface of the soil of 3 week old "~oter Gnom" toma~oes
in pots. Three days later the underside of the leaves of the
plants are sprayed with a zoospore suspension of Phytophthora
infestans. The plants are then kept for 5 days in a spray
chamber at 18 to 20C and staurated humidity, ~fter which
time typical leaf specks form. The size and number of the
specks serve as criterion for evaluating the effectiveness of
the tested substancesO
In the test of Example 4 the compounds of formula I exhibit
the following strong action against the leave-fungus (aver-
age values).
.
,, , . : . .: . : - .. ... .. . , . " . .. . . . . . .. ..
, . . . . .. .. . . .
~ . : . : . :, . :
.. , , ., :, . . , - . ; . : , .
~, . ,. . . .. , ~ . . .
: , , . .,, , , : :
5'~6
T a b 1 e
. ~
Compound Fungus infection Compound Fungus in~ection
in % in %
.
1 0-5 % 54 0 - 5 %
2 ~ 20 % 57 ~ 20 %
3 ~20 % 63 ~ 20 %
4 0-5 % 65 0 - 5 %
6 <20 % 70 ~ 20 %
7 ~20 % 74 0 - 5 %
-~ 8 0-5 % 75 ~ 20 %
9 ~ 20 % 76 20 -~0 %
j 12 ~20 % 80 ~20 %
13 ~ 20 % - 84 ~20 %
14 ~20 % g7 <20 %
j ~5 C 20 % 88 C20 %
16 ~ 20 % 91 ~ 20 %
17 20-40 % 93 ~20 %
19 ~2C % 95 C20 %
~ 25 ~-5 ~/O . 100 ~20 %
i 27 ~20 % 102 ~20 %
s, 28 0 5 % 10~ < 20 %
29 ~20 % 109 ~20 %
31 C20 % 110 ~ 20 %
ji 32 0-5 % 112 0 - 5 /,
; 35 ~ 20 % 113 C 20 ~/;.
42 C 20 % 114 ~ 20 %
53 0-5 % 115 ~ 20 %
. .
.~
- 44 - ;
''. ' .
.
: . . . .. .. :
- ~
. -, . . . .
'' '' '' ',: .' . ' ' .' .. ~ '. ' ;' , ', '. . ' '
~: ' ' ' . : . :' . ' ' ,; ~ :
~ D5 ~ 6
Compounds 1, 4, 8, 53, 65, 74 and 112 reduced the fungus in-
fection to G 20% in the same tests at application concentra-
tions of only 0.02%; compound 54 (D-form of compound 53) re-
duced it to only 0-5%.
''' ` ' ',
, `.
~` : " `-
:
:
:
:
, ~ :
. :
'~
: .
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~ - 45 - . .
,! . ~ :
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':
~ ~ S~ S ~6
Example 5
. ~
Action against Plasmopara viticola (Bert. et Curt.) (Berl. et
De Toni~ on vines
a) Residual preventive action
... ,.. .. ~ :
Vine cuttings of the variety "Chasselas" were reared in a
greenhouse. Three plants in the 10 leaf stage were sprayed with
a 0.05% broth prepared frorn the active substance and formu-
lated as a wettable powder. After the coating layer had dried,
the plants were infected on the underside of the leaves with
the spore suspension of the fungus. The plants were subsequen-
tly kept for 8 days in a humid chamber, after which time symp~
toms of the disease were visible on the control plants. The
number and size of the infected areas on the treated plants
served as criterion for evaluating the effectiveness of the
tested active substances.
.
b) Curative action
Vine cuttings of the variety "Chasselas" were reared in a
greenhouse and infected in the 10 leaf stage with a spore sus-
pension of Plasmopara viticola on the underside of the leaves. ~-
After they had been kept for 24 hours in a humid chamber, th~
plants were sprayed with an active substance broth~O.05%)pre~
pared rom a wettable powder of the active substance. The plants
were then kept for a further 7 days in a humid chamber, after
- 46 -
: , , , ,, "
,,: ~ , . . . .
: , , . ~ . I ,
... .
. .
~ ~ 5~15~ ~
which time the symptoms of the disease were visible on the
control plants. The size and number of the infected areas
served as criterion for evaluating the effectiveness of the
tested substances.
In both these tests the compounds of the formula I exhihited
a predominantly leaf-fungicidal action. Without exception,
the compounds listed in the Table of Example 4 reduced the
fungus infection to c~ 20% and in some cases, for examples
those of compounds l~ 53, 54, almost no infection occurred
(~-5%).
:,;
: .
.
.
.
47 -
'
. .. :-; . :, . . , .. .. -: .- ., ., . : ~ . . . .. . .
~ , , . , , , . . .: . , .
~ ~ S~ ~ 6
Example 6
Action against Erysiphe graminis on Hordeum vulgare ~barley)
.
Residual protective action
Barley plants about 8 cm in height were sprayed with a spray
broth (0.05% active substance) prepared from a wettable po~der
of the active substance. After 48 hours the treated plants
were dusted with conidia of the fungus. The infected barley
plants w~e stood in a greenhouse at about 22C and the fungus
infection was evaluated 10 days later.
A number of the compounds of the formula I, e.g. compounds 76
and 77, effect in this test a reduction of the flmgus infec-
tion to c 20%.
- ~8 -
:
-
~ ~ ~Q~
Example 7
Action against Py~hium debaryanum in Beta vulgaris (sugar
beet)
,
a) ~c~ion after soil application
The fungus is cultivated on sterile oat kernels and added
to a mixture of earth and sand. ~lower pots are filled with
the infected soil in which sugar beet seeds are then sown.
Immediately after sowing, the test preparations formulated as
wettable powders are poured in the form of aqueous suspensions
over the soil (0.002% active substance referred to the volume
of the soil). The pots are then stood for 2-3 weeks in a green-
house at 20-24C. The soil is kept unifonnly moist by gently
spraying it with water. The emergence of the surgar beet
plants as well as the number of healthy and sick plants are
ascertain~d in evaluating the tests.
b) Action after seed dressing
~ .
The fungus is cultivated on sterile oat kernels and added
to a mixture of earth and sant. Flower pots are filled with
the infected soil and sugar bee~ seeds which have been tre~ted
with the test preparations formulated as seed dressing powders
are sown therein (0.1% active substance referred to the weight
of the seeds). The pots are then stood in a greenhouse for
2~3 weeks at 20-24C. The soil is kept unifonnly moist by
_ ~9 -
",'
" , . ~ ,. :
: ', ~ ~ ' '. ". '',' ' ' ' ,,' ' '' ..
~ 6
gently spraying it with water. The emergence o:E the sugar
beet plants as well as the number of healthy and sick plants
are ascertained.
Under the conditions of both test a) and test b~, more than
85% of the sugar beet plants emerged aiter tr~atment with ~he
active substances of the formula I and had a healthy appear- -
ance, Les~ than 20% of the untreated control plants emerged
and their appearance was in part sickly.
- 50 -
. . ... . . .. .
, ,' `, ` ,'' ' ,' ~ ' `' " ' '.' ' ~' ' .~ " '
' ` , ` ' ,,
'
~56:D5~
Example 8
Growth inhibition of grasses
Aqueous preparations of an active substance of the formula I
were sprayed on parcels measuring 3 m2 of a prepared outdoor
lawn consisting of the grasses Lolium perenne, Poa pratensis
and Festuca rubra, two days after the first cutting in spring.
The amount of active substance used corresponded to 5 kg per
hectare. Untreated parcels were used as controls. The aver-
age growth in height of the grasses in treated and untreated
parcels was ascertained 6 weeks after the application. The
turf treated with the active substances was uniformly compact
and had a healthy appearance. Pronounced or almost complete
growth inhibition was effected in particular by active sub-
stances of the formula I wherein -X-R3 represents the radical
-CO-N(R")~ defined for the formula I.
:''
- 51 -
, ~ , . .~ . , ., ", , , . , , . - .
... . . . .
