GB1587571A - 2-cyclo-propylamino-4 -formylamino-6-aminos-triazine derivatives and their use as insecticides - Google Patents
2-cyclo-propylamino-4 -formylamino-6-aminos-triazine derivatives and their use as insecticides Download PDFInfo
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- GB1587571A GB1587571A GB34791/77A GB3479177A GB1587571A GB 1587571 A GB1587571 A GB 1587571A GB 34791/77 A GB34791/77 A GB 34791/77A GB 3479177 A GB3479177 A GB 3479177A GB 1587571 A GB1587571 A GB 1587571A
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- represents hydrogen
- cyclopropylamino
- formylamino
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
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- Health & Medical Sciences (AREA)
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Description
(54) 2-CYCLOPROPYLAMINO-4-FORMYLAMINO-6-AMINO-S-TRIAZINE
DERIVATIVES AND THEIR USE AS INSECTICIDES
(71) We, CIBA-GEIGY AG., a Swiss Body Corporate of Basle, Switzerland, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:
The present invention relates to 2-cyclopropylamino-4-formylamino-6-amino-s-triazine derivatives and salts thereof, to a process for their manufacture and to their use as insecticides.
The 2-cyclopropylamino-4-formylamino-6-amino-s-triazine derivates of the invention have the formula
wnereln Rl represents hydrogen, C1-C4-alkyl which is unsubstituted or substituted by C14 alkoxy, or represents C3 or C4-alkenyl, C3 or C4-alkynyl, cyclopropyl, hydroxy,
methoxy or ethoxy; R2 represents hydrogen, methyl or ethyl, or
R, and R2 together with the nitrogen atom to which they are attached represent a 5- or
6-membered heterocyclic ring in which the nitrogen atom shown is the sole hetero
atom or which contains a further nitrogen atom or an oxygen atom. and
R3 represents hydrogen or methyl, and the acid addition salts thereof.
Possible alkyl groups represcnted by R, can be straight-chain or branched, unsubstituted or substituted by alkoxy groups of 1 to 4 carbon atoms. Examples of such alkyl groups include methyl, ethyl. n-propyl. isopropyl. n-butyl, isobutyl. sec. and tert. butyl, and also 2-methoxyethyl. Examples of C3 or C4-alkenyl and C3 or C4-alkynyl groups comprise allyl and propargyl respectively.
The term "acid addition salts" of the 2-cyclop ropylamino-4-formylamino-6-amino-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 compounds of the formula I in which Rl represents hydrogen. C1-C4-alkyl which is unsubstituted or substituted by CI-C4 alkoxy.
or represents C3 or C4-alkenyl, C3 or C4-alkynyl. cyclopropyl, hydroxyl, methoxy or ethoxy; R2 represents hydrogen, methyl or ethyl, or R, and R2 together with the nitrogen atom to which they are attached represent 1-pyrrolidinyl, 1-piperidinyl. 4-morpholinyl, l-piperazinyl. l-(4-methyl)-piperazinyl or l-imadazolyl and R3 represents hydrogen or methyl.
Particularly preferred compounds are those in which R1 represents hydrogen, methyl, ethyl, isopropyl,2-methoxyethyl, allyl, propargyl or cyclopropyl, R2 represents hydrogen or methyl or R, and R2 together with the nitrogen atom to which they are attached represent 1-pyrrolidinyl, 4-morpholinyl or 1-imidazolyl and R3 represents hydrogen.
The most preferred compounds however are those in which R1 represents hydrogen, ethyl, allyl or propargyl, R2 represents hydrogen and R3 represents hydrogen, and, in particular the compounds:
2-cyclopropylamino- 4-formylamino-6-ethylamino.s-triazine, 2-cyclopropylamino-4-formylamino-6-allylamino-s-triazine, 2-cyclopropylamino-4-formylamino-6-propargylamino-s-triazine and
2-cyclopropylamino-4-formylamino-6-amino-s-triazine.
The compounds of the formula I can be obtained by methods which are known per se, for example by
(a) converting a 2-cyclopropylamino-4-formamidino-6-amino-s-triazine of the formula
II
wherein R1, R2 and R3 are as defined in formula land R4 and R5 are the same or different and represents methyl or ethyl, into the corresponding 2-cyclopropylamino-4-formylamino6-amino-s-triazine by hydrolysis, or
(b) reacting a 2-cyclopropylamino-4,6-diamino-s-triazine of the formula III
in which R3 is as defined in formula I and in which R1 and R2 have the meanings assigned to R1 and R2 in formula I with the exception of hydrogen, with a formylating agent.
The hydrolysis (a) can be carried out with the addition of an acid, such as hydrochloric acid, at 0 to 1000C under normal pressure. Advantageously, water is used as solvent or diluent, if appropriate with the addition of an organic solvent, such as dioxane or an alcohol, whereupon the reaction product precipitates.
The reaction (b) is preferably carried out using a mixture of formic acid and acetic anhydride as the formylating reagent or by condensation of a compound of the formula III with ortho-formic acid ie an ortho-formate in the presence of a catalytic amount of a strong acid. and subsequent partial hydrolysis. In the former case it is possible to use in the reaction a solvent or diluent which is inert to the reactants. and in the latter case the orthoester is used as solvent.
The starting material of the formula II can be obtained by reacting a triazine derivative of the formula III
in which R1, R2 and R3 are as defined in formula I, with an acetal of the formula V
in which R4 and R5 have the meanings given in formula II.
The compounds of formula II are claimed in our Application No. 34792/77 (Serial No.
1587572).
The starting material of the formula III can be prepared by conventional methods from chlorine-substituted s-triazine derivatives by replacing chlorine with the corresponding amino group or groups. Some of the compounds of formula III are claimed in our Application
No. 34793/77 (Serial No.1587573).
Diamino- and triamino-s-triazines are described as chemosterilants for adult houseflies (Musca domestica) in U.S. patent specification 3,189,521. The chemosterilising action on insects of 2,4,6-triamino-s-triziane derivatives (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)1 and G.C. LaBrecque, R.L. Fye, A.B. DeMilo and A.B.
Borkovec [J. Econ. Entomol. 61, (6), 1621 (1968)1 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 the salts thereof, on adult houseflies (Musca domestica). The chemosterilising action of acetylmelamines is described in U.S. patent specification 3,520,974.
Surprisingly, it has now been 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 compounds of the formula I act on the developmental stages of the insects. The action consists in killing the freshly hatched larvae or preventing adults from hatching from 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 compounds of the formula I can be used in particular for controlling hygiene pests and animal ectoparasites of the order Diptera, especially of the families: Culicidae, Simuliidae,
Tipulidae, Muscidae and Calliphoridae.
The compounds of the formula I can be used without any additive or together with suitable carrier(s) and/or other additive(s). Suitable carriers and other additives can be solid or liquid and can be any conventionally used in the art of formulation of a larvicidal insecticide, for example natural or regenerated substances, solvents and/or dispersants.
The compositions according to the invention can be manufactured in known manner by homogeneously mixing and/or grinding a compound of the formula I with a carrier, which can include a dispersant or solvent and which is inert to the active substance (compound of formula I).
The active substances may be processed to the following formulations:
Solid formulations:
Dusts, tracking agents and granules (coated granules. impregnated 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).
To manufacture a solid formulation (dusts, tracking agents). the active substance is mixed with a solid carrier. Suitable carriers arc, 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), calcium and magnesium sulphates. magnesium oxide. ground synthetic 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 carriers 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. Six2. granicalcium. bentonite etc. and then evaporating the solvent.
Polymer granules can also be manufactured by mixing an active substance of the formula I
with polymerisable compounds (ure a / formalde hyde; dicyandiamide /formaldehyde; melamine/formaldehyde or others), whereupon a mild polymerisation is carried out that does not affect the active substances and in the process of which the granulation is carried out during the gel formation. It is more advantageous 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 manufactured with the aid of atomisers.
It is also possible to obtain granules by compacting the carrier with the active substance and additive(s) and subsequently comminuting 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 or 9 carbon atoms in the alkyl moiety, ligninsulphonic acid, the alkali metal and alkaline earth metal salts thereof, polyethylene glycol ethers, fatty alcohol polyethylene glycol ethers having 5 to 20 ethylene oxide radicals per molecule and 8 to 18 carbon atoms in the fatty alcohol moiety, condensation products of ethylene oxide, propylene oxide, polyvinylpyrrolidone, 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 consists of active substance. carrier, optionally additive(s) which stabilize the active substance, surface-active substance(s) and anti-foam(s) and, if appropriate, solvent(s).
Wettable powders and pastes are obtained by mixing and grinding the active substance with dispersant(s) and pulverulent carriers in suitable devices until homogeneity is attained.
Suitable carrier(s) 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 sulphonated 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 lignin sulphonic acid. in addition, alkylaryl sulphonates, alkali metal and alkaline earth metal salts of dibutyl naphthalene sulphonic acid, fatty alcohol sulphates 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 dilauryl ammonium chloride and fatty acid alkali metal and alkaline earth metal salts.
Suitable anti-foams are for example silicone oils.
The active substances is so mixed. ground. sieved and strained with the additive(s) mentioned above that, in wettable powders the solid particle size of 0.02 to 0.04 mm and in pastes. of 0.03 mm. is not exceeded. Emulsifiable concentrates and pastes are manufactured by using dispersants. such as those referred to above. organic solvents, and water. Examples of suitable solvents are: alcohols. dimethyl sulphoxide. and mineral oil fractions which boil between 120 and 350"C. The solvents must be virtually odourless and inert to the active substances.
Furthermore. the compositions according to the invention can take the form of solutions.
For this purpose the active substance or several active substances of the general formula I are dissolved in suitable organic solvents or mixtures of solvents. Aliphatic and aromatic hydrocarbons. chlorinated derivatives thereof, alkylnaphthalencs and mineral oils, singly or in admixture. can be used as organic solvents.
Formulations of the 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 partsoftale 2 parts of active substance I part of highly disperse silica
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 80y.
Granules:
5 parts of active substance are dissolved in a solvent, e.g.
methylene chloride, and mixed with
2 parts of polyethylene glycol ("Carbowax"; Registered Trade
Mark)
91.5 parts of calcium carbonate are impregnated with the mixture and
1.5 parts of precipitated silica are admixed.
The solvent is subsequently evaporated.
Wettable Power:
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 silica and
30 parts of China clay
and the mixture is finely ground.
Emulsifiable Concentrate:
20 parts of active substance are mixed with
20 parts of emulsifier, e.g. a mixture of alkylarylpolyglycol ether
with alkylarylsulphonates, and
60 parts of solvent
until the solution is completely homogeneous. By diluting this
concentrate with water it is possible to obtain an emulsion of the
desired concentration.
Premix (feed additive):
0.25 part of active substance and
4.75 parts of secondary calcium phosphate, or China clay, aerosil or
carbonate of lime are homogenously mixed with
95 parts of an animal feed, e.g. poultry food.
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, the compositions of the present invention can contain. for example, insecticides to broaden the activity spectrum.
The compositions, or the compounds of formula (I) contained therein, exert their inhibitory action therefore chiefly on the development of larvae or pupae of insects, preferably of the orderDiptera.
EXAMPLE I 2- Cyclopropylamino- 4-formylamino- 6-morpholino-s-triazine 25 g of 2-cyclopropylamino-4-N",N'-dimethylformamidino-6-morpholino-s-triazine are dissolved in 1000 ml of water and the solution is treated with 100 ml of 1N hydrochloric acid.
After stirring for 15 minutes at room temperature. the 2-cyclopropylamino-4-formylamino6-morpholino-s-triazine with a melting point of 288"C begins to precipitate. The crude product is recristallised from dimethylformamide. Melting point: 291 -292 C.
The following compounds of the formula I are prepared in accordance with the above procedure:
No.
Compound
mp. in C 1 2-cyclopropylamino-4-formylamino-6-morpho- lino-s-triazinehydrochloride 244-245 2 2-cyclopropylamino-4-formylamino-6-pyrroli- dino-s-triazine 260-261 3 2-cyclopropylamino-4-formylamino-6-methyl-
amino-s-triazine 244-245 4 2-cycloproylamino-4-formylamino-6-ethyl-
amino-s-triazine 257-258 5 2-cycloproylamino-4-formylamino-6-allyl- amino-s-triazine 245-246 6 2-cyclopropylamino-4-formylamino-6-isopro- pylamino-s-triazine 199-201 7 2-cyclopropylamino-4-formylamino-6-propargyl
amino-s-triazine 258-260 8 2-cyclopropylamino-4-formylamino-6-imidazolo- s-triazine 256-259 9 2-cyclopropylamino-4-formylamino-6-dimethyl- amino-s-triazine 259-261
10 2-cyclopropylamino-4-formylamino-6-(2- methoxyethylamino)-s-triazine 214-215
11 2,6-bis-(cyclopropylamino)-4-formylamino-s-
triazine 259-260
12 2-cyclopropylamino-4-formylamino-6-amino-s- triazine 69-27 1 13 3-cyclopropylamino-4-form\lamino-6-( N-ethylamino)-s-triazine 205
EXAMPLE2
Action against Musca donicstica 50 g of freshly prepared CSMA nutrient substrate for maggots were charged into beakers.
2.5 ml portions of a 1% acetonic solution of the respective active substance were pipetted onto the nutrient substrate present in the beakers. The substrate was then thoroughly mixed and the solvent subsequently allowed to evaporate.
Then 25 one. two- and three-day-old maggots and approx. 50 eggs of Musca dotncsnc.a were put into each of the beakers containing the treated nutrient substrate for testing with each active substance. After the maggots had pupated. the pupae were separated from the substrate by flushing them out with water and counted. The number of flies which had hatched out of the pupae was then counted after 10 days and any influence on the metamorphosis thereby determined.
In the above text. the compounds of Example 1 displayed a good action against Musca domestica.
EXAMPLE 3
Action against Lucilia sericata
I ml of an aqueous solution containing 0.5% of active substance was added to 9 ml of a culture medium at 50 C. Then approx. 30 freshly hatched larvae of Lucilia sericata were added to the culture medium and the insecticidal action was determined by evaluation of mortality after 48 and 96 hours respectively. In this test. the compounds of the formula I acted well against Lucilin sericata.
EXAMPLE 4
Action againstA des aegypti larvae
Active substance concentrations of 10, 5 and 1 ppm respectively were obtained by pipetting a specific amount of a 0.1 % solution of the active substance in acetone onto the surface of 150 ml of water in each of a number of beakers.
After the acetone had evaporated, 30 to 40 two-day-old larvae ofAt;des aegypti were put into each of the beakers containing the active substance solution. Evaluation of mortality is made after 1,2 and 5 days respectively.
In this test, the compounds of the formula I acted well againstA des aegypti.
WHAT WE CLAIM IS:
1. 2-Cyclopropylamino-4-formylamino-6-amino-s-triazines of the formula
wherein
R1 represents hydrogen, C,-C4-alkyl which is unsubstituted or substituted by C1-C4
alkoxy, or represents C3 or C4-alkenyl, C3 or C4-alkynyl, cyclopropyl, hydroxy,
methoxy or ethoxy;
R2 represents hydrogen, methyl or ethyl, or R1 and R2 together with the nitrogen atom to which they are atached represent a 5- or
6-membered heterocyclic ring in which the nitrogen atom shown is the sole hetero
atom or which contains a further nitrogen atom or an oxygen atom; and
R3 represents hydrogen or methyl, and the acid addition salts thereof.
2. Compounds according to claim 1 wherein R1 represents hydrogen, C1-C4-alkyl which is unsubstituted or substituted by C,-4 alkoxy, or represents C3- or C4-alkenyl, C3- or
C4-alkynyl, cyclopropyl, hydroxyl, methoxy or ethoxy; R2 represents hydrogen methyl or ethyl; or Rl and R2 together with the nitrogen atom to which they are attached represent 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 1-piperazinyl or 1-(4-methyl)-piperazinyl and
R3 represents hydrogen or methyl.
3. Compounds according to claim 1 wherein R1 and R2, together with the nitrogen atom to which they are attached, represent a 1-imidazolyl group and R3 represents hydrogen or methyl.
4. Compounds according to claim 1 wherein R, represents hydrogen, C14 alkyl which is unsubstituted or substituted by C14 alkoxy or represents C3- or C4-alkenyl, C3 or C4-alkynyl or cyclopropyl and R2 represents hydrogen, methyl or ethyl; or R, and R2 together with the nitrogen atom to which they are attached form a heterocyclic ring as defined in claim 1.
5. Compounds according to claim 1 wherein R1 represents hydrogen, methyl, ethyl, isopropyl. 2-methoxyethyl. allyl, propargyl or cyclopropyl; R2 represents hydrogen or methyl or R1 and R2 together with the nitrogen atom to which they are attached represent 1-pyrrolidinyl or 4-morpholinyl, and R3 represents hydrogen.
6. Compounds according to claim 1 wherein R, and R2 together with the nitrogen atom to which they are attached represent a 1-imidazolyl group, and R3 represents hydrogen.
7. Compounds according to claim 1 wherein R, represents hydrogen, ethyl, allyl or propargyl; R2 represents hydrogen and R3 represents hydrogen.
8. Compounds according to claim 5. 6 or 7 in the form of hydrochloride salts.
9. 2-Cyclopropylamino-4-formylamino-6-ethylamino-s-triazine.
10. 2-Cyclopropylamino-4-formylamino-6-allylamino-s-triazine.
11. 2-Cyclopropylamino-4-formylamino-6-propargylamino-s-triazine.
12. 2-Cyclopropylamino-4-formylamino-6-amino-s-triazine.
13. 2-Cyclopropylamino-4-formylamino-6-morpholino-s-triazine.
14. Each of the compounds 2,3,6 8 to l 1 and 13 specifically hereinbefore named.
15. A process for the manufacture of 2-cyclopropylamino-4-formylamino-6-amino-striazines of the formula I according to claim 1, wherein a 2-cyclopropylamino-4-formamidino-6-amino-s-triazine of the formula II
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (25)
1. 2-Cyclopropylamino-4-formylamino-6-amino-s-triazines of the formula
wherein
R1 represents hydrogen, C,-C4-alkyl which is unsubstituted or substituted by C1-C4
alkoxy, or represents C3 or C4-alkenyl, C3 or C4-alkynyl, cyclopropyl, hydroxy,
methoxy or ethoxy;
R2 represents hydrogen, methyl or ethyl, or R1 and R2 together with the nitrogen atom to which they are atached represent a 5- or
6-membered heterocyclic ring in which the nitrogen atom shown is the sole hetero
atom or which contains a further nitrogen atom or an oxygen atom; and
R3 represents hydrogen or methyl, and the acid addition salts thereof.
2. Compounds according to claim 1 wherein R1 represents hydrogen, C1-C4-alkyl which is unsubstituted or substituted by C,-4 alkoxy, or represents C3- or C4-alkenyl, C3- or
C4-alkynyl, cyclopropyl, hydroxyl, methoxy or ethoxy; R2 represents hydrogen methyl or ethyl; or Rl and R2 together with the nitrogen atom to which they are attached represent 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 1-piperazinyl or 1-(4-methyl)-piperazinyl and
R3 represents hydrogen or methyl.
3. Compounds according to claim 1 wherein R1 and R2, together with the nitrogen atom to which they are attached, represent a 1-imidazolyl group and R3 represents hydrogen or methyl.
4. Compounds according to claim 1 wherein R, represents hydrogen, C14 alkyl which is unsubstituted or substituted by C14 alkoxy or represents C3- or C4-alkenyl, C3 or C4-alkynyl or cyclopropyl and R2 represents hydrogen, methyl or ethyl; or R, and R2 together with the nitrogen atom to which they are attached form a heterocyclic ring as defined in claim 1.
5. Compounds according to claim 1 wherein R1 represents hydrogen, methyl, ethyl, isopropyl. 2-methoxyethyl. allyl, propargyl or cyclopropyl; R2 represents hydrogen or methyl or R1 and R2 together with the nitrogen atom to which they are attached represent 1-pyrrolidinyl or 4-morpholinyl, and R3 represents hydrogen.
6. Compounds according to claim 1 wherein R, and R2 together with the nitrogen atom to which they are attached represent a 1-imidazolyl group, and R3 represents hydrogen.
7. Compounds according to claim 1 wherein R, represents hydrogen, ethyl, allyl or propargyl; R2 represents hydrogen and R3 represents hydrogen.
8. Compounds according to claim 5. 6 or 7 in the form of hydrochloride salts.
9. 2-Cyclopropylamino-4-formylamino-6-ethylamino-s-triazine.
10. 2-Cyclopropylamino-4-formylamino-6-allylamino-s-triazine.
11. 2-Cyclopropylamino-4-formylamino-6-propargylamino-s-triazine.
12. 2-Cyclopropylamino-4-formylamino-6-amino-s-triazine.
13. 2-Cyclopropylamino-4-formylamino-6-morpholino-s-triazine.
14. Each of the compounds 2,3,6 8 to l 1 and 13 specifically hereinbefore named.
15. A process for the manufacture of 2-cyclopropylamino-4-formylamino-6-amino-striazines of the formula I according to claim 1, wherein a 2-cyclopropylamino-4-formamidino-6-amino-s-triazine of the formula II
in which Rl, R2 and R3 are as defined in formula land R4 and R5 are the same or different and represent methyl or ethyl, is converted by hydrolysis into the corresponding 2-cyclopropylamino-4- formylamino-6-amino-s-triazine.
16. A process for the manufacture of 2cyclopropylamino-4-formylamino-6-amino-s- triazines of the formula I according to claim 1, wherein a 2-cyclopropylamino-4,6-diaminos-triazine of the formula III
in which R3 is as defined in formula I and in which Rl and R2 have the meanings assigned to
R, and R2 in formula I with the exception of hydrogen. is reacted with a formylating agent.
17. A process according to claim 16 wherein the formylating agent is a mixture of formic acid and acetic anhydride or is ortho-formic acid.
18. 2-Cyclopropylamino-4-formylamino-6-amino-s-triazine derivatives according to claim 1 when prepared by a process claimed in claim 15, or 17.
19. An insecticidal composition which comprises a 2-cyclopropylamino4-formylamino-6- amino-s-triazine claimed in claim l and a carrier.
20. A composition according to claim 19 in the form of a dust, tracking agent, granules wettable powder, emulsifiable concentrate. animal feed additive or spray.
21. A method of preventing the development of adult insects from larvae or pupae, which comprises applying to the larvae or pupae a 2-cyclopropylamino-4,6-diamino-s-triazine claimed in claim 1 or 2.
22. A method according to claim 2 1 wherein the insects are of the order Diptera.
23. A method according to claim 22 wherein the insects are of the families Culicidae,
Simuliidae, Tipulidae, Muscidae and Ca lliphori doe belonging to the order Diptera.
24. A method according to claim 21, 22 or 23 wherein a compound claimed in any one of claims 4,5,7 and 13 is applied.
25. A method according to claim 2 1. 22 or 23 wherein a compound claimed in any one of claims 3.6, and 8 to 12 is applied.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1055976A CH603049A5 (en) | 1976-08-19 | 1976-08-19 | (2)-Cyclopropyl-amino-(4)-formyl-amino-(1,3,5)-triazine cpds. |
CH271977 | 1977-03-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1587571A true GB1587571A (en) | 1981-04-08 |
Family
ID=25691230
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB34791/77A Expired GB1587571A (en) | 1976-08-19 | 1977-08-18 | 2-cyclo-propylamino-4 -formylamino-6-aminos-triazine derivatives and their use as insecticides |
Country Status (11)
Country | Link |
---|---|
JP (1) | JPS5325586A (en) |
AU (1) | AU518857B2 (en) |
CA (1) | CA1084923A (en) |
DE (1) | DE2736699A1 (en) |
ES (1) | ES461716A1 (en) |
FR (1) | FR2362135A1 (en) |
GB (1) | GB1587571A (en) |
IL (1) | IL52766A (en) |
NL (1) | NL7709098A (en) |
NZ (1) | NZ184954A (en) |
YU (1) | YU198977A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ221262A (en) * | 1986-08-06 | 1990-08-28 | Ciba Geigy Ag | Preventing the reinfestation of dogs and cats by fleas by administering to the host a flea growth inhibiting substance orally, parenterally or by implant |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL39385A (en) * | 1971-06-01 | 1974-12-31 | Ciba Geigy Ag | A method for combating insects by the use of 4-azido-2,6-diamino triazine derivatives,certain such novel derivatives and their manufacture |
-
1977
- 1977-08-16 DE DE19772736699 patent/DE2736699A1/en not_active Withdrawn
- 1977-08-17 YU YU01989/77A patent/YU198977A/en unknown
- 1977-08-17 CA CA284,902A patent/CA1084923A/en not_active Expired
- 1977-08-17 IL IL52766A patent/IL52766A/en unknown
- 1977-08-17 NL NL7709098A patent/NL7709098A/en not_active Application Discontinuation
- 1977-08-18 FR FR7725248A patent/FR2362135A1/en active Granted
- 1977-08-18 GB GB34791/77A patent/GB1587571A/en not_active Expired
- 1977-08-18 NZ NZ184954A patent/NZ184954A/en unknown
- 1977-08-18 ES ES461716A patent/ES461716A1/en not_active Expired
- 1977-08-19 AU AU28042/77A patent/AU518857B2/en not_active Expired
- 1977-08-19 JP JP9939977A patent/JPS5325586A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
AU518857B2 (en) | 1981-10-22 |
JPS638105B2 (en) | 1988-02-19 |
NZ184954A (en) | 1980-05-08 |
YU198977A (en) | 1982-08-31 |
FR2362135B1 (en) | 1980-06-27 |
FR2362135A1 (en) | 1978-03-17 |
AU2804277A (en) | 1979-02-22 |
ES461716A1 (en) | 1978-12-16 |
IL52766A0 (en) | 1977-10-31 |
CA1084923A (en) | 1980-09-02 |
DE2736699A1 (en) | 1978-06-22 |
IL52766A (en) | 1981-02-27 |
JPS5325586A (en) | 1978-03-09 |
NL7709098A (en) | 1978-02-21 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |