Note: Descriptions are shown in the official language in which they were submitted.
1~8492~
The present invention relates to novel 2-cyclopropyl-
amino-4,6-diamino-s-triazine derivatives and salts thereof, to a
proceSs for their manufacture and to their use in pest control.
The 2-cyclopropylamino-4,6-diamino-s-triazine deriva-
tives have the formula
R ~ / 1
N
N
/ N ~ N ~ NH ~ R5
R4
wherein
Rl represents hydrogen, Cl-C3-alkyl which is unsubstituted
or substituted by lower alkoxy or cyano, or represents
C3-C4-alkenyl, C3-C4-alkynyl or cyclopropyl,
R2 represents hydrogen, methyl or ethyl, or
Rl and R2 together With the nitrogen atom to which they are
attached represent a 5- or 6-membered heterocycllc
ring which can contain a further nitrogen atom or an
oxygen atom,
R represents hydrogen, Cl-C3-alkyl, C3-alkenyl, C3-
alkynyl or cyclopropyl,
R4 represents hydrogen, methyl or ethyl, or
R3 and R4 together with the nitrogen atom to which they are
attached represent a 5- or 6-membered heterocyclic
~, .
: - 2 - ~
- ~
' B~i
'.
-. ' . ~ . ', :
:: :. .. . . :
,~ . .
1084~
ring which can contain a further nitrogen atom or an
oxygen atom, and
R5 represents hydrogen or methyl,
with the proviso that if one of the groups NRlR2 and NR3R4
represents NH-cyclopropyl or NH-Cl-C3-alkyl the other group does
not represent NH-cyclopropyl, and the acid addition salts thereof.
Possible alkyl groups Rl and R3 can be straight-chain
or branched, unsubstituted or substituted for example by cyano
groups or alkoxy groups of 1 to 4 carbon atoms. Examples of such
alkyl groups include: methyl, ethyl, n-propyl, isopropyl, 2-
methoxyethyl, l-cyanoethyl, l-cyanopropyl and 2-cyano-prop-2-yl.
i Examples of possible alkenyl and alkynyl groups Rl and R3 in-
clude allyl and propargyl respectively.
The term "acid addition salts" of the 2-cyclopropyl-
; amino-4,6-diamino-s-triazine derivatives of the formula I is to
be understood as meaning salts with strong mineral acids, for
example salts with hydrochloric acid or sulphuric acid.
Preferred compounds on account of their action are
those compounds of the formula I in which Rl represents hydrogen,
Cl-C3-alkyl which is unsubstituted or substituted by lower
alkoxy, or represents C3-C4-alkenyl, C3-C4-alkynyl or cyclopropyl,
R2 represents hydrogen, methyl or ethyl, or Rl and R2 together
with the nitrogen atom to which they are attached represent 1-
pyrrolidinyl, l-piperidinyl, 4-morpholinyl, l-piperazinyl, 1-
(4-methyl)-piperazinyl or l-imidazolyl, R3 represents hydrogen,
Cl-C3-alkyl, C3-alkenyl, C3-alkynyl or cyclopropyl, R4 represents
-- 3 --
Bi
.
. : ~
~084921
hydrogen, methyl or ethyl, or R3 and R4 together with the
nitrogen atom to which they are attached represent l-pyrrolidinyl,
l-plperidinyl, 4-morpholinyl, l-piperazinyl, 1-(4-methyl)-piper-
azinyl or l-imidazolyl, and R5 represents hydrogen or methyl,
and the acid addition salts thereof.
Compounds to be singled out for special mention are
those in which Rl represents hydrogen, methyl, ethyl, n-propyl,
isopropyl or cyclopropyl, R2 represents hydrogen, methyl or
ethyl, or Rl and R2 together with the nitrogen atom to which
they are attached represent l-pyrrolidinyl, l-piperidinyl, 4-
morpholinyl or l-imidazolyl, R3 represents hydrogen, methyl,
ethyl, n-propyl, isopropyl or cyclopropyl, R4 represents hydrogen,
methyl or ethyl, and R5 represents hydrogen, and the acid
addition salts thereof.
Particularly preferred compounds are those in which
Rl represents hydrogen, ethyl or cyclopropyl, R2 represents
hydrogen, R3 represents hydrogen or methyl, R4 represents hydro-
gen, methyl or ethyl, and R5 represents hydrogen, whilst at
least one of the symbols Rl, R3 and R4 represents hydrogen,
-- 4 --
,
, ' ~ ~ ,, ~ ' . '
: . -
-- ~849~
and the hydrochlorides thereof, in particular 2-cyclopropyl-
amino-4-amino-6-ethylamino-s-triazine hydrochloride,
2,4-bis-(cyclopropylamino)-6-amino-s-triazine,
2-cyclopropylamino_4-amino-6-methylamino-s-triazine
dihydrochloride,
2-cyclopropylamino-4,6-diamino-s-triazine,
2-cyclopropylamino-4-amino-6-dimethylamino-s-triazine,
2-cyclopropylamino_4,6_bis_(ethylamino)-s-triazine dihydro-
chloride and
2-cyclopropylamino_4-amino_6-(N-methyl-N-ethylamino)-s-
triazine.
The compounds of the formula I are obtained by methods which
are known per se, for-example by
a) reacting a 2-cyclopropylamino_4-amino-6-halogeno_s-
triazine of the formula II, in which Rl, R2 and R5 are as
defined in formula I and X represents halogen, preferably
chlorine, with ammonia or a primary or secondary amine of the
formula V, in which R3 and R4 are as defined in formula I:
~ /
X ~ ~ ~ + 2 H~'\'' 3 -~~~~~~
II
S _
.
- .
-
1084921
~N/
~ R
N ~ 3 ~
R / ~ N ~ ~ R5 ~ /
or
b) reacting a 2,4-diamino-6-halogeno-s-triazine of the
formula III, in which Rl, R2, R3 and R4 are as defined in
formula I and X represents halogen, preferably chlorine,
with a compound of the formula VI, in which R5 is as defined
in formula I:
~ /
~ .
N N ~ R
> ~ N r ~ ~ 5
R4
III ~ VI
- 6 -
~084921
R2 Rl ,
\/ '
' ~ -
R / ~\N~ ~R + H2N ~ R5 . HX
or
c) if in the compounds of the formula I Rl has the same
meaning as R3 and R2 has the same meaning as R4, reacting a
2-cyclopropylamino-4,6-dihalogeno-s-triazine of the formula IV,
in which R5 is as defined in formula I and X represents halo-
gen, preferably chlorine, with ammonia or a primary or secon-
dary amine of the formula VII, in which R'l has the meaning
of Rl~R3, as defined in formula I,and R'2 has the meaning of
R2=R4, as defined in formula I:
~ R
X ~ 1I NH ~ `+ 4 HN
IV ~II
. . .
-- 7 --
1084921
R~ / 1
N
/ ~ N ~ ~ + 2 ~N \ l ~ HX
R2
Ia
The substitution of the halogen atoms with ammonia, primary
and/or secondary amines of the formulae V, VI and VII is
effected by dissolving the starting materials of the
formulae II, III and IV in inert solvents, for example
acetone, acetone/water mixtures, methyl ethyl ketone,
dioxane or dioxane/water mixtures, and reacting these
mixtures at normal or, if appropriate, elevated pressure and
at temperatures between 20 and 150C, preferably between
50 and 140C, with ammonia, primary and/or secondary amines.
Most of the starting materials of the formulae II, III and IV
are known or they can be obtained in accordance with known
methods.
~iamino- and triamino-s_triazines are described as chemo-
sterilants for adult houseflies (Musca domestica) in US
patent speci~ication 3,189,521. ~he chemosterilising action
on insects of 2,4,6-triamino-s-triazine derivatives
:, , - - ~
'
~ ~0849~1
(melamine derivatives) is also described by S. Nagasawa et
al., Botyu-Kagaku 39 (4), 105 (1974). A.B. Borkovec and
A B DeMilo [J. Med. Chem. 10 (5), 457 (1967)] and G.C.
LaBrecque,R.L. Fye, A.B.DeMilo and A.B. Borkovec lJ. Econ.
Entomol. 61, (6), 1621 (1968)] also describe the chemosterilising
action of~among other compounds,2-cyclohexylamino-4,6-diamino-s-
triazine, 2-cyclohexylamino-4,6_dihexylamino-s_triazine and
2,4,6-tris-cyclohexylamino-s-triazine, and t~e salts thereof,
on adult houseflies (Musca domestica).
Surprisingly, it has now ~een found that the compounds of the
formula I possess a marked larvicidal action on insect larvae,
preferably on Diptera larvae. In contrast to the above
mentioned insecticidal chemosterilants, the c~mpounds of the
formula I act on the developmental stages of the insects. The
action consists in killing the freshly hatchetlarvae or preventing
ad~lltsfrom hatchingfrom the pupae. The mode of action of the
compounds of the formula I is not to be compared with that of
classical insecticides, chemosterilants or juvenile hormone
analogues.
The active compounds of the formula I can be used in parti-
cular for controlling hygiene pests and animal ectoparasites
of the order Diptera and of the families: Culicidae,
Simuliidae, Tipulidae, Muscidae and Calliphoridae.
_ 9 _
, . .
-- :L08492~
The compounds of the formula I can be used as pure active
substance or together with suitable carriers and/or additives.
Suitable carriers and additives can be solid or liquid and
correspond to the substances conventionally used in the art
of formulation, for example natural or regenerated substances,
solvents and/or dispersants.
The c~mpositions according to the invention are manufactured
in known manner by homogeneously mixing and/or grinding
active substances (compounds) of the formula I with the
suitable carriers, with or without the addition of disper-
sants or solvents which are inert to the active substances.
The active substances may be processed to the following
formulations:
Solid formulations:
Dusts, tracking agents and granules (coated granules,
~mpregnated granules and homogeneous granules), premix
(feed additive)
Liquid formulations:
a) active substance concentrates which are dispersible
in water: wettable powders, pastes and emulsions;
b) solutions: sprays (aerosols).
- 10 -
iO84921
To manufacture solid forms (dusts, tracking agents), the
active substances are mixed with solid carriers. Suitable
carriers are, for example: kaolin, talc, bolus, loess, chalk,
limestone, ground limestone, attaclay, dolomite, diatomaceous
earth, precipitated silica, alkaline earth silicates, sodium
and potassium aluminium silicates (feldspar and mica), cal-
cium and magnesiwn sulphates, magnesium oxide, ground synthe-
tic materials, fertilisers, for example ammonium sulphate,
ammonium phosphate, ammonium nitrate, urea, ground vegetable
products, such as corn meal, bark dust, sawdust, nutshell meal,
cellulose powder, residues of plant extractions, activated
charcoal etc. These substances can either be used alone or in
admixture with one another.
Granules can be very easily manufactured by dissolving an
active substance of the formula I in an organic solvent and
applying the solution thereby obtained to a granulated
mineral, for example attapulgite, SiO2, granicalcium,
bentonite etc. and then evaporating the solvent.
Polymer granules can also be manufactured by mixing the
active substances of the formula I with polymerisable
compounds (urea/formaldehyde; dicyandiamide formaldehyde;
melamine/formaldehyde or others), whereupon a mild polymeri-
sation is carried out that does not affect the active sub-
stances and in the process of which the granulation is
- 11 -
.
~084921
carried out during the gel formation. It is more advanta-
geous to impregnate finished, porous polymer granules (urea/
formaldehyde, polyacrylonitrile, polyester or others) which
have a specific surface area and a favourable predeterminable
adsorption/desorption ratio, with the active substances, for
example in the form of their solutions (in a low boiling
solvent) and to remove the solvent. Polymer granules of this
kind in the form of microgranules having preferably a bulk
density of 300 g/litre to 600 g/litre can also be manufac-
tured with the aid of atomisers.
It is also possible to obtain granules by compacting the
carrier with the active substance and additives and sub-
sequently commminuting the product.
To these mixtures can also be added additives which stabilize
the active substance and/or nonionics, anionics and cationics,
which, for example, ensure a better wettability (wetting
agents) and dispersibility (dispersants). Examples of suitable
substances are: olein/chalk mixture, cellulose derivatives
(methyl cellulose, carboxymethyl cellulose), hydroxyethyl
glycol ethers of monoalkyl and dialkyl phenols having 5 to
15 ethylene oxide radicals per molecule and 8 to 9 carbon
atoms in the alkyl moiety, ligninsulphonic acid, ~he alkali
metal and alkaline earth metal salts thereof, polyethylene
glycol ethers (carbowaxes), fatty alcohol polyethylene glycol
~0849Zl
ethers having 5 to 20 ethylene oxide radicals per molecule and
8 to 18 carbon atoms in the fatty alcohol moiety, condensation
products of ethy~ene oxide, propylene oxide, polyvinylpyrroli-
done, polyvinyl alcohol, condensation products of urea and
formaldehyde, and also latex products.
Water-dispersible concentrates, i.e. wettable powders, pastes
and emulsifiable concentrates, are compositions which can be
diluted with water to the desired concentration. They consist
of active substance, carrier, optionally additives which
stabilize the active substance, surface-active substances and
anti-foams and, if appropriate, solvents.
Wettable powders and pastes are bbtained by mixing and
grinding the active substances with dispersants and pulveru-
lent carriers in suitable devices until homogeneity isattained. Suitable carriers are, for example, those already
mentioned for the solid forms of application. In some cases
it is advantageous to use mixtures of different carriers.
Examples of dispersants are: condensation products of sul-
phonated naphthalene and sulphonated naphthalene derivatives
with formaldehyde, condensation products of naphthalene or
naphthalene sulphonic acids with phenol and formaldehyde,
as well as alkali metal, ammonium and alkaline earth metal
salts of ligninsulphonic acid, in addition alkylarylsul-
phonates, alkali metal and al~aline earth metal salts of
dibutylnaphthalenesulphonic acid, fatty alcohol sulphates
- 13 -
1al84921
such as salts of sulphated hexadecanols, heptadecanols,octadecanols, and salts of sulphated fatty alcohol glycol
ethers, the sodium salt of oleyl methyl tauride, ditertiary
ethylene glycols, dialkyl_dilaurylammonium chloride and
fatty acid alkali metal and alkaline earth metal salts.
Suitable anti-foams are for example silicone oils.
The active substances are so mixed, ground,sieved and
strained with the additives mentioned above that, in wettable
powders, the solid particle size of 0.02 to 0.0~ mm and in
pastes, of 0.03 mm, is not exceeded Emulsifiable concentra-
tes and pastes are manufactured by using dispersants, such
as those referred to above, organic solvents, and water.
Examples of suitable solvents are: alcohols, dimethyl sul-
phoxide, and mineral oil fractions which boil between 120
and 350C The solvents must be virtually odourless and inert
to the active substances.
Furthermore, the compositions according to the invention
can be applied in the form of solutions. For this purpose
the active substance or several acti~e substances of the
general formula I are dissolved in suitable organic solvents
or mixtures of solvents. Aliphatic and aromatic hydrocarbons,
chlorinated derivatives thereof, alkylnaphthalenes and
mineral oils, singly or in admixture, can be used as organic
solvents.
_ 14 -
' ~
~0849;2:~
Formulations of the novel active compounds of the formula I
are described hereinafter. The parts denote parts by weight.
Dusts:
The following substances are used to manufacture a) a 0.5%
and b) a 2% dust:
a) 0.5 part of active substance
99.5 parts of talc
b) 2 parts of active substance
1 part of highly disperse silicic acid
97 parts of talc.
The active substances are mixed with the carriers and ground.
Tracking Agents:
5 parts of active substance are mixed with
95 parts of carbonate of lime and ground to an average
particle size of 80~.
Granules:
-
5 parts of active substance are dissolved in a solven~,e.g. methylene chloride, and mixed with
2 parts of polyethylene `glycol ("Carbowax").
91.5 parts of calcium carbonate are impregnated with the
mixture and
1.5 parts of precipitated silicic acid,are admixed.
The solvent is subsequently evaporated.
~84921
Wettable Powder-
50 parts of active substance are mixed with
5 parts of a dispersing agent, e.g. sodium lignin~
sulphonate,
5 parts of a wetting agent, e.g. dibutylnaphthalene-
sulphonic acid
10 parts of silicic acid and
30 parts of China clay
and the mixture is finely ground.
Emulsifiable Concentrate:
20 parts of active substance are mixed ~Jith
20 parts of emulsifier, e.g. a mixture of alkylaryl-
polyglycol ether with alkylarylsulphonates, and
60 parts of solvent
until the solution is completely homogeneous.
By diluting this concentrate with water i.t is
possible to obtain an emulsion of the desired
concentration.
Premix (feed additive):
0.25 p~rt of active substance and
4.75 parts of secondary calcium phosphate, or China
clay, aerosil or carbonate of lime are homoge-
neously mixed with
95 parts of an animal feed, e.g. poultry food.
_ 16 -
~084921
Spray:
The following constituents are used to manufacture a 2% spray:
2 parts of active substance
98 parts of kerosene.
Other biocidal active substances or agents can be admixed
with the compositions described hereinabove. Thus in addition
to the cited compounds of the general formula I, the compo-
sitions of the present invention can obtain, for example,
insecticides to broaden the activity spectrum
The compositions, or the active compounds contained therein,
exert their inhibitory action therefore chiefly on the
development of larvae or pupae of insects, preferably of the
order Diptera.
_ 17 -
~84g2~
Example 1
2-Cyclopropylamino-4-amino-6-ethylamino-s-triazine
A mixture of 13.7 g of 2-cyclopropylamino-4-chloro-
6-ethylamino-s-triazine, 17.4 g of 25% conc. aqueous ammonia
and 30 ml of dioxane is heated for 2 hours in an autoclave to
130C. After cooling, the reaction mixture is poured into
water, whereupon the crude product precipitates. After drying,
the product is recrystallised from ether/hexane. Melting
point: 141-145C.
Example _
a) 2-Cyclopropylamino-4-amino-6-morpholino-s-triazine
9.3 g of 2-Cyclopropylamino-4-chloro-6-amino-s-
triazine are suspended in a mixture of 45 ml of dioxane and
9 ml of ether. Then 8.7 g of morpholine are added dropwise
at room temperature. The reaction is exothermic and the re-
action mixture becomes fluid. The reaction mixture is allowed
to continue to react for 16 hours at room temperature and
the dioxane and ether are then removed in vacuo. The residue
is diluted with water and filtered. After drying, the residual
crude product is recrystallised from methanol. Melting point:
186C.
b) 5 g of 2-cyclopropylamino-4-amino-6-morpholino-
s-triazine are dissolved in 700 ml of abs. ether and then
gaseous hydrogen chloride is introduced at 10C until the sol-
ution is saturated. The precipitated crystals are filtered
off and washed with a small amount of methanol. The result-
ant hydrochloride of 2-cyclopropylamino-4-amino-6-morpholino-
- 18 -
B~
~C38~9Zl
s-triazine melts at 250C.
Example 3
2-Cycloprop~lamino-4,6-bis-dimethylamino-s-triazine
123 g of 2-cyclopropylamino-4,6-dichloro-s-triazine
are dissolved in 300 ml of dioxane. Then 397 g of 40.8%
aqueous dimethylamine are added dropwise with gentle cooling
in such a manner that the internal temperature does not exceed
55C. The reaction is allowed to continue for 4 hours at
room temperature. The reaction mixture is then taken up in
ether and the aqueous phase is separated. The ether and
dioxane are removed in vacuo after washing with water and
drying over sodium sulphate. The crude product is recrystal-
lised from isopropanol. Melting point: 82-83 C.
The following active compounds of the formula I are
also prepared by proceeding as described in Examples 1 to 3:
-- 19 --
~.'
1084921
No. Compound mp. in C
1 2-cyclopropylamino-4-amino-6-
methylamino-s-triazine 159-162
2 2-cyclopropylamino-4,6-bis-
(isopropylamino)-s-triazine 119-121
3 2-cyclopropylamino-4-amino-6-
pyrrolidino-s-triazine 186
4 2-cyclopropylamino-4-ethylamino-
6-morpholino-s-triazine 90-91
2-cyclopropylamino-4-ethylamino-
6-pyrrolidino-s-triazine 169-170
6 2-cyclopropylamino-4-amino-6-
morpholino-s-triazine 186
7 2-cyclopropylamino-4-ethylamino-
6-morpholino-s-triazine 90-91
8 2-cyclopropylamino-4-amino-6-
morpholino-s-triazine hydrochloride 250
9 2-cyclopropylamino-4-amino-6-
imidazolo-s-triazine 244-245
2-cyclopropylamino-4-amino-6-
pyrrolidino-s-triazine
dihydrochloride 196-197
11 2-cyclopropylamino-4-amino-6-
ethylamino-s-triazine
dihydrochloride 199-200
- 20 -
-
.
,: .
.
i~84921
No. Compound mp. in C
12 2-cyclopropylamino-4-ethylamino-
6-pyrrolidino-s-triazine
hydrochloride 226-227
13 2-cyclopropylamino-4-ethylamino-
6-morpholino-s-triazine
hydrochloride 230-231
14 2-cyclopropylamino-4-amino-6-
isopropylamino-s-triazine
dihydrochloride 172-173
2-cyclopropylamino-4-amino-6-
allylamino-s-triazine
dihydrochloride 183-185
16 2-cyclopropylamino-4-amino-6-
propargylamino-s-triazine 225-226
17 2,4-bis-(cyclopropylamino)-6-amino-
s-triazine 137-140
18 2,4-bis-(cyclopropylamino)-6-dimethyl-
amino-s-triazine 136-137
19 2-cyclopropylamino-4-amino-6-
methylamino-s-triazine
dihydrochloride 197-199
2-cyclopropylamino-4,6-diamino-s-
triazine 219-222
21 2-cyclopropylamino-4-amino-6-
(2-methoxyethylamino)-s-triazine 154-156
22 2-cyclopropylamino-4-amino-6-
dimethylamino-s-triazine 182-184
_ 21 -
,~?
'
-~
.
1~849Zl
No. _ Compound mp. in C
23 2-cyclopropylamino-4,6-bis-
(ethylamino)-s-triazine (viscous)
24 2-cyclopropylamino-4-methylamino-
6-n-propylamino-s-triazine (viscous)
2-cyclopropylamino-4-ethylamino-
6-n-propylamino-s-triazine (viscous)
26 2,4-bis-(cyclopropylamino)-6-diethyl-
amino-s-triazine 76-77
27 2-cyclopropylamino-4-amino-6-(N-
methyl-N-ethylamino)-s-triazine 150-152
28 2-cyclopropylamino-4,6-bis-(methyl-
amino)-s-triazine dihydrochloride 158-162
29 2-cyclopropylamino-4-methylamino-6-
dimethylamino-s-triazine dihydrochloride164-165
2-cyclopropylamino-4,6-bis-(ethylamino)-
s-triazine dihydrochloride 170-172
31 2-cyclopropylamino-4-methylamino-6-
n-propylamino-s-triazine dihydrochloride164-165
32 2-cyclopropylamino-4-ethylamino-6-n-
propyl-amino-s-triazine dihydrochloride164-165
33 2-cyclopropylamino-4-dimethylamino-6-
isopropylamino-s-triazine 140-142
34 2-cyclopropylamino-4-dimethylamino-6-
morpholino-s-triazine 148-150
~. ' ,
.
iO8~9Zl
No. ~omponnd m~p. in C
2-cyclopropylamino-4-amino-6-
diethylamino-s-triazine 128-129
36 2.4-bis-(cyclopropylamino)-6-
morpholino-s-triazine 137-138
37 2.4-bis-(cyclopropylamino)-6-
pyrrolidino-s-triazine 193-196
38 2-cyclopropylamino-4-dimethyl-
amino-6-propargylamino-s-
triazine hydrochloride 178-180
39 2-cyclopropylamino-4-dimethyl-
amino-6-morpholino-s-triazine
hydrochloride 208
2-cyclopropylamino-4-methylamino-
6-diethylamino-s-triazine hydrochloride153-154
41 2-cyclopropylamino-4-ethylamino-6-
diethyl-amino-s-triazine hydrochloride144-145
42 2-cyclopropylamino-4-dimethylamino-
6-diethylamino-s-triazine hydrochloride153-154
43 2-cyclopropylamino-4-dimethylamino-
6-ethylamino-s-triazine hydrochloride 220
44 2-cyclopropylamino-4-dimethylamino-
6-pyrrolidino-s-triazine hydrochloride 214
2-cyclopropylamino-4.6-bis-(diethyl-
amino)-s-triazine hydrochloride (oily)
46 2-cyclopropylamino-4-ethylamino-6-
isopropylamino-s-triazine 94.5-96
47 2-cyclopropylamino-4-ethylamino-6-
dimethylamino-s-triazine 111-112
48 2-cyclopropylamino-4.6-bis-(ethyl-
amino)-s-triazine hydrochloride 140-142
. `''~ .
10849Zl
Example _
Test substance: compounds of the formula I formulated as
acetonic solutions
Test subject: Musca domestica
Test material: CSMA nutrient substrate for maggots
Concentration: 0.1%, 0.05%, 0.01% of active substance
Test method: 50 g of freshly prepared CSMA nutrient sub-
strate for maggots are charged into beakers.
A specific amount of a 1% acetonic solution
of the respective active substance is
pipetted onto the nutrient substrate present
in the beakers. The substrate is then
thoroughly mixed and the acetone subsequently
allowed to evaporate over a period of at
least 20 hours.
Then 25 one-day-old maggots of Musca domestica
are put into each of the beakers containing
the treated nutrient substrate for testing
with each active substance at one of its
given concentrations. After 5 days, the
pupae are separated from the substrate by
flushing them out with water and then deposited
in the same beaker.
Each batch of flushed out pupae is counted
to determine the toxic effect of the active
- 24 -
..
.
.
~084921
substance on the maggot development. The
number of flies which have hatched out of
the pupae are then counted after lO days
and any influence on the metamorphosis there-
by determined.
The compounds of the formula I exhibit good
activity in this test.
Example 5
Test substance: compound of the formula I formulated as
acetonic solutions
Test subject: Aedes aégypti
Test material: yoghourt beakers filled with water
Concentration: lO ppm, 5 ppm, and l ppm of active substance
Test method: Yoghourt beakers are each filled with 150 ml
of water and a specific amount of a 0.1%
solution of the active substance in acetone
is pipetted onto the surface of the water.
After the acetone has evaporated, 30 to 40
two-day-old larvae of Aedes aegypti are put
into each of the beakers containing the
active substance solution. Two beakers per
concentration of active substance are used
for the test. Then ground dog-biscuit is
added to the beakers, which are covered with
a copper gauze top.
- 25 -
B
.
..... .. . .
.. .
- . .. . .- . -- . . - . . .
.
~ ~ .. . . . -
.. . . . ~ .
.
~0849Z~
Evaluation of mortality is made after 1, 2
and 5 days respectively. Subsequently,
evaluation is made of the inhibiting action
on pupation, metamorphosis, and shedding
and emergence to the adult stage.
The compounds of the formula I have a good action in this
test.
Example 6
Test substances:Active substances of the formula I formu-
lated as 25% wettable powder or as aqueous
solution or suspension of the hydrochlorides.
Test subject: Lucilia sericata (blowfly), freshly hatched-
larvae I
Concentration: 250 ppm of active substance
Test method: 1 ml of an aqueous suspension or solution
of the active substance in a concentration
of 1000 ppm is added at 50C to 3 ml of a
sPecial culture medium so as to give a
homogeneous mixture with an active substance
content of 250 ppm. Approx. 30 Lucilia
larvae are used for each test. Evaluation
of mortality is made after 4 days.
In this test, the compounds of formula I exhibit good action.
E~
,.
.,
. .. : .-; . .
