FONGICIDE

FUNGICIDE

Abrégé anglais

ABSTRACT OF THE DISCLOSURE
A fungicide containing as an active ingredient the compounds with
the general formula 1
<IMG> (1)
where:
X is a halide or methyl sulphate ion with "n" equal 1 or 2,
R1 and R2 are alkyl radicals with 1-4 carbon atoms,
R3 is an alkyl radical with 1-4 carbon atoms or cyclohexyl radical,
R4 is an alkyl radical with 1-18 carbon atoms,
or
R2 and R3 together with the nitrogen atom form a ring with formula 2
<IMG> (2)
where:
W is an oxygen atom, methylene group or a nitrogen atom substituted as
in formula 3
<IMG> (3)
where:
R1 and R4 have the above moaning, U and Y are hydrogen atoms or methyl
groups, Z is a hydrogen atom,
or
Y and Z together are an oxygen atom.
The agent containing as active compounds with the general formula 1, where

the substituents have the above meaning, have strong, also systemic, action
towards fungi, especially of the Alternaria and Phytophthora genera.
-2-

Revendications

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A fungicidal composition comprising a compound of the
general formula 1
<IMG> (1)
where:
X is a halide or methyl sulphate ion with "n" equal 1
or 2,
R1 and R2 are alkyl radicals with 1-4 carbon atoms,
R3 is an alkyl radical with 1-4 carbon atoms or a cyclo-
hexyl radical,
R4 is an alkyl radical with 1-18 carbon atoms,
or
R2 and R3 together with the nitrogen atom form a ring
with formula 2
<IMG> (2)
where:
W is an oxygen atom, methylene group or a nitrogen atom
substituted as in formula 3
<IMG> (3)
where:
R1 and R4 have above meaning,
U and Y are hydrogen atoms or methyl groups,
Z is a hydrogen atom,
or

y and Z together are an oxygen atom, together with an
agriculturally acceptable carrier.
2. A composition according to claim 1 wherein the active
compound is dodecyloxymethyl trimethylamine chloride.
3. A method of combatting fungi which comprises applying
to a habitat thereof an effective amount of a composition as
claimed in claim 1.

Description

This invention relates to a fungicide containing as active agent
the compo~mds with the general formula 1
Rl - / R2 (Xe )n (1)
R4-0-H2C 3
For control of pathogenic fungi of the Alternaria and especially
of the Phytophthora genera, it is known to use agents containing such active
substances as dithiocarbamates~ copper compounds, organo-tin compounds and
others.
Among the above, most frequently used is mankozeb (a complex of
ethylene-bis-dithiocarbamic acid manganese salt with zinc ions), copper
oxychloride, and phentin acetateO
The above agents control fungi of the Phytophthora and Alternaria
genera; however neither of them is a systemic agent.
Preventive use of copper oxychloride requires application of very
high doses (about 8 kg/ha~ phentin aceta~e, as all organotin fungicides,
is highly toxic to all mammals; whilst zineb and mankozeb have relatively
short protective activity. Further, these fungicides are also no~ soluble
in water. Water solubility is another important factor, as spore ~ermination
takes place in water. Also, as the above compounds are not systemic agents,
. .,:
they do~not prevent infection o-f leaves newl~ developed after fungicide
a :application.
Unexpectedly, it has been found that compounds wi~h the general
formula 1, where:
Rl ~ / R2 ~X )n (1)
R4 2 3
X is a halide or methyl sulphate ion with "n" equal 1 or 2,
~1 and R2 are a~yl radicals with 1-4 carbon atoms,
.
~ ' -1-

R3 is an alkyl radical with 1-4 carbon atoms or a cyclohexyl radical,
R4 is an alkyl radical with 1-18 carbon atoms,
or
R2 and R3 together with the nitrogen atom form a ring with the formula 2
/~ ,
N W (2)
sr z ..
where:
W is an oxygen atom, methylene group or a nitrogen atom substltuted
as in formula 3
~ N ~ Rl (3)
~ C~l2~0-R4
lo where: .
R1 and R4 have the above meaning, ~ ~-
U and Y are hydrogen atoms or methyl groups, :
Z is a hydrogen atom
or
Y and Z are together an oxygen atom;
have strong~ and also systemic, action towards fungi, especially of the
Alternaria and Phytophthora genera.
The agent, according to the present invention, containing as an
active substance compounds with the general for~ula 1, may also contain
known additives such as~mineral or organic carriers, thinners or solvents, : -
surface-actlve substances, buffers and adherents.
Effectiveness of the agents according to the yresent invention
~has been tested during biological studies m vitro on the following fungi:
Alternaria tenuis, Botrytis cinerea and Aspergillus niger Results are given
in Table 1.
'~ .
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TABLE 1
E~feCtiVeneSS Of agentS With the gen~ra1 Or~U1a 1
~ _ ~
! COnCentratiOn COnCentratiOn
inhibiting SPOre inh1biting
R R R R germinatiO~ in 1inear mYCe1~a
NO 1 2 ;3 4 X n RPm _ gr
A1terna- BOtrYtiS ASPergi1-
nUaSte Ciner
ea 1US niger
1 -CH3 -CH3 -CH3 -C2H5 C1 1 1000 1000 200
2 -CH3 -CH3 -CH3 -C3H7 C1 1 1000 1000 20
3 -CH3 -CH3 -CH3 -C4H9 C1 1 1000 1000 20
4 -CH3 -CH3 -CH3 -C6H13 C1 1 1000 1000 2
00
5 -C~l3 -CH3 -CH3 -C7H1S C1 1 1000 1000 2
00
6 -CH3 -CH3 -CH3 -C8H17 C1 1 100C 1000 ~
7 -CH3 -CH3 -C~H3 -C9H19 C1 1 1000 1000 2
0 ~ 1
8 -CH3 -CH3 -CH3 -C10H21 C1 1 1100 100 2
0
-CH3 -CH3 -CH3 -C12H25 C1 1 10 +10 2
0
10 -CH3 -CH3 O -C18H37 C1 1 100 100 20
00
11 -CH3 -CH2-CH2-CH2- C16H33 C1 1 -~10 10 -~2000
12 -CH3 -CH2CH20CH2CH2 -C18H37 C1 1 100 100 2000
13 ¦-CH3 -CM2(CH2)3CH2 -C12H25 C1 1 10 2000
14 ¦-CH3 -CH2(CH2)3CH2 ~ -C1~H37 C1 1 +10 2000
~ __ . - _ _ .... ~ ~ ..
; ~ Known~ referenCe fUngiCide Z1neb 100 100 2CO
~ ma~ko~eb _~ lOC 2(10
:
: ~
~ .

Exam~le I
50 parts by weight of dodecyloxymethyl-trimethylamine chloride,
40 parts by weight of mineral carrier (kieselguhr), 2 parts by weight of
wetting agent -~ 8 parts by weight of dispersing agent ~waste calcium sulphite
liquor) were mixed. The fungicide was tested in concentrations of the
active compound 0.1% and 0.01~ and effectiveness compared to a known
fungicide (mankozeb). Investigations were carried out on tomato seedlings
in the 5-6 leaves phase, spraying plants with the tested substance and
infecting afterwards with a suspension of Phytophthora infestans spores.
The percent of infected plants were then evaluated in comparison to unsprayed
plants (controls) after 6 daysO Results are given in Table 2.
TABLE 2
Effectiveness of the agent obtained in Example I against potato
blight~Phytophthora infestans)
. ~ ,. .
Fungicide Concentration in ~ Percent of infected plants ~
. .. .. _ _
Age~t as in 0.01 25.8
Example I 0.1 0.0
~ _ _ . . . _
manko~eb 0.01 34.1
0.1 9.0 '
_ ~ .
Check (without _ 100 0
the preparate) _ .
~ .. ~ _ . _ __ _ '.. :, ' -
~: ~
10 parts by weight of dodecyloxymethyl trimethylamine chloride,
0.3 parts by weight of alkylarylpolyglycol ether, 89.7 parts by weight of
. . .
dlstilled water, were mixed~
The fungicide has been studied for systemic activity in comparison
to a k~lown ~stemic funglclde - carbenda~ime tN-(2-benzimida~ole)-carbamic
acid methyl ester~ and a known preventive agent (mankozeb).
The agent in example II~`and reference fungicides were diluted with
4-

distilled water to concentrations of l.0~ O.l and 0.01%. Roots of bean
seedlings were submerged in the solutions for 24 hours. Next, the sprouts
were cut into l cm fragments. The fragments, by five, were next placed in
Petri dishes with an agar-potato nutrient infected with Aspergillus niger
spores. Mycelia growth inhibition zone around the fragments was measured
after 4 days. Results are given in Table 3.
TABL~ 3
Systemic activity of the agent wikh general formula l.
. ,,,,,, ~ _
Diameter of Aspergillus
niger mycelia growth Average zone of
Tested Concentration inhibition zone around growth inhibition
agent in % the fragment in mm in mm
_ _ _ 2- _ _ _ _ -
Agent as l.0 7 9 5 7 9 7.4
in Example O.l 5 O 5 5 O 3.2
II O.Ol 0 0 0 0 0 0~0
Carbenda- l.0 6 5 9 5 7 6.4
zime O.l 6 5 5 0 6 4.4
0.01 O O O O O 0.0
, _ , _ . __ _ _ _ ' ":'
Mankozeb l.0 O O O O O 0.0
0.1 O O O O O 0.0
0.01 O O O O O 0.0
. _ _ , _ __. _ _ . --i
Check with
water _ 0 0 0 I 0 0 0.0
_ _ _ _ _ : I _ _ .: _
Tl Le obtained results testify thak the age nt according to the
present invention, penetrates through~the roots ~o bean sprouts, similarly
as the known systemic fungiclde - carbendazime. Thus systemlc action of the
invented agent has been confirmed.
An advantage of the agent, according to the present invention,
besides high effectiveness is its systemic activity, not confirmed until
:
now in known fungicides controlling fungi of the Alternaria and Phytophthora
genera Also an important advantage of *he agent~according~to *he presént
, .
~ 5-

invention is its low toxicity to mammals and very good solubility in water,
simplifying application.
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