CA1100514A - Imidazolidine derivatives useful as insecticides and acaricides - Google Patents
Imidazolidine derivatives useful as insecticides and acaricidesInfo
- Publication number
- CA1100514A CA1100514A CA188,750A CA188750A CA1100514A CA 1100514 A CA1100514 A CA 1100514A CA 188750 A CA188750 A CA 188750A CA 1100514 A CA1100514 A CA 1100514A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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Abstract
'b \
ABSTRACT OF THE DISCLOSURE
The invention relates to novel pesticidal compositions and to certain novel compounds employed therein as active ingredient. These novel compounds have the formula:
ABSTRACT OF THE DISCLOSURE
The invention relates to novel pesticidal compositions and to certain novel compounds employed therein as active ingredient. These novel compounds have the formula:
Description
110~5:14 The present invention relates to pesticidal compositions and to certain novel compounds employed therein as active ingredient. The comp-ositions show interesting insecticidal and acaricidal activities.
According to one feature of the present invention there are provided imidazolidine derivatives of the formula:
Rl Rl ~ N X ~
R2 ~T CC13 R2 wherein Rl and R2 are in the 3-, 4- or 5-positions and R2 represents a halogen atom or a nitro, lower alkyl or alkoxy group and Rl represents a halogen atom or a nitro, lower alkyl or alkoxy group or (where R2 is other than a 4-chloro atom or a 4-methyl, 4-methoxy or 4-nitro group) a hydrogen atom, or an acid addition salt thereof.
According to one feature of the present invention there are provided imidazolidine derivatives of the formula:
Rl Rl ~ N X ~
R2 ~T CC13 R2 wherein Rl and R2 are in the 3-, 4- or 5-positions and R2 represents a halogen atom or a nitro, lower alkyl or alkoxy group and Rl represents a halogen atom or a nitro, lower alkyl or alkoxy group or (where R2 is other than a 4-chloro atom or a 4-methyl, 4-methoxy or 4-nitro group) a hydrogen atom, or an acid addition salt thereof.
-2- t~
Sl~
A compound of formula I or an acid addition salt thereof is preferably used in which Rl and R2, which may be the same or different, each represents a chlorine or bromine atom or an alkyl or alkoxy group with 1 or 2 carbon atoms.
It is also preferred to use a compound of formula I or an acid addition salt thereof in which Rl represents a
Sl~
A compound of formula I or an acid addition salt thereof is preferably used in which Rl and R2, which may be the same or different, each represents a chlorine or bromine atom or an alkyl or alkoxy group with 1 or 2 carbon atoms.
It is also preferred to use a compound of formula I or an acid addition salt thereof in which Rl represents a
3- or 4-chloro atom or a 3- or 4-methyl group, such compounds being especially preferred when R2 represents a ~ydrogen atom, a chlorine atom or a methyl group.
The compounds of formula I and the acid addition salts thereof are e~emplified by the compounds:-1,3-bis-(3-chlorophenyl)-2-trichloromethyl-imidazolidine and the acid addition salts thereof; and 1,3-bis-(3,5-dimethylphenyl)-2-trichloromethyl-imidazolidine and the acid addition salts thereof.
For the control of insects the active ingredients are preferably used in the conventional manner together with diluents and carriers e.g. emulsifiabIe concentratés wetta~le powders, solutions,aerosols,dusting powders, granulates or colloidal dispersions.
~10~514 The preferred concentration of active ingredient for use in insecticidal and ac~ricidal compositions according to the invention is from 0.02 to 5% by weight.
If required, the concentrates may be mixed with water, so that a spray preferably having a concentration of approximately 0.02 to 5% by weight of active ingredient is obtained.
Carriers and additives which may conveniently be used according to the present invention include for example solvents, diluents, stabilizers, dispersion agents, wetting agents and emulsifying agents. Moreover the insect-icidal and acaricidal compositions according to the present invention m~y, if desired, also contain further known insecticidal or acaricidal agents.
The compoun~s of formula I show good activity against various pests. Thus, for example, houseflies (Musca domestica) cockroaches ~e.g. Phyllodroma~ermanica), spider mites (e,g. Tetranychus urticae), aphids (e.g. Aphis fabae), caterpillars (e.g. of Plutella maculipennis) and bugs (e g. Epilach_a varivestis) may be extenminated by the use of even small doses of active ingredient.
5~4 The compositions of the present invention are, in general, specific in their actlvity against insects and acaricidS and as a result they may be used for specific plant protection. The compositions of the present invention are substantially non~toxic to warm-blooded animals.
Moreover the active ingredients of the compositions of the present invention decompose with release of chloroform and degrade rapidly to give non-toxic compounds which do not hann the environment.
According to a further feature of the present invention there is provided a method of preventing or inhibiting the growth or proliferation of insects and/or acarids which comprises applying to a site infested with or susceptible to infestation by insects and/or acarids an e~fective amount of a compound of formula I as hereinbefore described or an acid addition salt thereof.
The compounds of formula I may, for example, be produced by reacting a corresponding diaryl-substituted ethylene d;amine of formula II with chloral according to known processes (e.g. H.W. Wanzlick and E. Schikora, Chem.
Ber 94~ 2839 (1961)):
5~4 Thus accorting to a further feature of the present inYentiOn there is provided a process for the preparation of compounds of formula I as hereinbefore defined or an acid addition salt ~hereof which comprises reacting a compound of the formula:-NH--CH2--CH2 NH ~ II
~wherein Rl and R2 are as hereinbefore defined) with a compound of theformula:-~IC CC13 III
whereby a compound of formula I is obtained and, if desired, subsequently converting the compound of formula I thus obtained into an acid addîtion salt thereof. The reaction is preferably effected in the presence ofglacial acetic acid or a mixture of glacial acetic acit and hydrochloric acid as solvent and atvantageously at ambient temperatuIe or at a slightly elevated temperature. We have ~ound, however, that where a 3-substituted or 3,5-tisubstituted ;~,.~.
1 10 ~ 5 ~ 4 dianilinoethane is used as the compound of formula II, only very poor yields of the compound of formula I are obtained and in some cases we have been unable to obtain any yield at all. We have, however, discovered that when the reaction between the compound of formula II
and the compound of formula III is effected with simultaneous removal of water formed in the reaction e~g.
by azeotropic distillation with a substantially water immiscible sol~ent, the compound of formula I is obtained in better yield. The substantially water immiscible solvents include~ for example, benzene, toluene or xylene. The reaction may also, if desired, be effected in the presence of a catalyst e.g. a reaction accelerator e.g. an acidic catalyst, such as p-toluenesulfonic acid. This modified process results in a higher purity and in better yields, of the compounds of formula I even when an unsubstituted or ~-substituted diamine is used as the compound of formula II.
The starting material of formula II may, for example,-be obtained according to known processes e.g. from the corresponding aniline and an ethylene dihalide [for example H.W_ Wanzlick and W. Lockel, B.86,1463 (1953)] or by condensation with glyoxal [analogously to J.M. Klieman and R.K. Barnes, J. Org. Chem. 35, 3I40 (1970)]; but in the latter case the product thus obtained must subsequently SJ~
be hydrogenated.
According to a still fur~her feature of the present invention there are provided compounds of the general formula:-N ~ ~
~wherein R2 represents a halogen atom or a nitro, loweralkyl or alkoxy group and Rl represents a halogen atom or a nitro, lower alkyl or alkoxy group or (where R2 is other than a 4-chloro atom or a 4-methyl, 4-methoxy group or
The compounds of formula I and the acid addition salts thereof are e~emplified by the compounds:-1,3-bis-(3-chlorophenyl)-2-trichloromethyl-imidazolidine and the acid addition salts thereof; and 1,3-bis-(3,5-dimethylphenyl)-2-trichloromethyl-imidazolidine and the acid addition salts thereof.
For the control of insects the active ingredients are preferably used in the conventional manner together with diluents and carriers e.g. emulsifiabIe concentratés wetta~le powders, solutions,aerosols,dusting powders, granulates or colloidal dispersions.
~10~514 The preferred concentration of active ingredient for use in insecticidal and ac~ricidal compositions according to the invention is from 0.02 to 5% by weight.
If required, the concentrates may be mixed with water, so that a spray preferably having a concentration of approximately 0.02 to 5% by weight of active ingredient is obtained.
Carriers and additives which may conveniently be used according to the present invention include for example solvents, diluents, stabilizers, dispersion agents, wetting agents and emulsifying agents. Moreover the insect-icidal and acaricidal compositions according to the present invention m~y, if desired, also contain further known insecticidal or acaricidal agents.
The compoun~s of formula I show good activity against various pests. Thus, for example, houseflies (Musca domestica) cockroaches ~e.g. Phyllodroma~ermanica), spider mites (e,g. Tetranychus urticae), aphids (e.g. Aphis fabae), caterpillars (e.g. of Plutella maculipennis) and bugs (e g. Epilach_a varivestis) may be extenminated by the use of even small doses of active ingredient.
5~4 The compositions of the present invention are, in general, specific in their actlvity against insects and acaricidS and as a result they may be used for specific plant protection. The compositions of the present invention are substantially non~toxic to warm-blooded animals.
Moreover the active ingredients of the compositions of the present invention decompose with release of chloroform and degrade rapidly to give non-toxic compounds which do not hann the environment.
According to a further feature of the present invention there is provided a method of preventing or inhibiting the growth or proliferation of insects and/or acarids which comprises applying to a site infested with or susceptible to infestation by insects and/or acarids an e~fective amount of a compound of formula I as hereinbefore described or an acid addition salt thereof.
The compounds of formula I may, for example, be produced by reacting a corresponding diaryl-substituted ethylene d;amine of formula II with chloral according to known processes (e.g. H.W. Wanzlick and E. Schikora, Chem.
Ber 94~ 2839 (1961)):
5~4 Thus accorting to a further feature of the present inYentiOn there is provided a process for the preparation of compounds of formula I as hereinbefore defined or an acid addition salt ~hereof which comprises reacting a compound of the formula:-NH--CH2--CH2 NH ~ II
~wherein Rl and R2 are as hereinbefore defined) with a compound of theformula:-~IC CC13 III
whereby a compound of formula I is obtained and, if desired, subsequently converting the compound of formula I thus obtained into an acid addîtion salt thereof. The reaction is preferably effected in the presence ofglacial acetic acid or a mixture of glacial acetic acit and hydrochloric acid as solvent and atvantageously at ambient temperatuIe or at a slightly elevated temperature. We have ~ound, however, that where a 3-substituted or 3,5-tisubstituted ;~,.~.
1 10 ~ 5 ~ 4 dianilinoethane is used as the compound of formula II, only very poor yields of the compound of formula I are obtained and in some cases we have been unable to obtain any yield at all. We have, however, discovered that when the reaction between the compound of formula II
and the compound of formula III is effected with simultaneous removal of water formed in the reaction e~g.
by azeotropic distillation with a substantially water immiscible sol~ent, the compound of formula I is obtained in better yield. The substantially water immiscible solvents include~ for example, benzene, toluene or xylene. The reaction may also, if desired, be effected in the presence of a catalyst e.g. a reaction accelerator e.g. an acidic catalyst, such as p-toluenesulfonic acid. This modified process results in a higher purity and in better yields, of the compounds of formula I even when an unsubstituted or ~-substituted diamine is used as the compound of formula II.
The starting material of formula II may, for example,-be obtained according to known processes e.g. from the corresponding aniline and an ethylene dihalide [for example H.W_ Wanzlick and W. Lockel, B.86,1463 (1953)] or by condensation with glyoxal [analogously to J.M. Klieman and R.K. Barnes, J. Org. Chem. 35, 3I40 (1970)]; but in the latter case the product thus obtained must subsequently SJ~
be hydrogenated.
According to a still fur~her feature of the present invention there are provided compounds of the general formula:-N ~ ~
~wherein R2 represents a halogen atom or a nitro, loweralkyl or alkoxy group and Rl represents a halogen atom or a nitro, lower alkyl or alkoxy group or (where R2 is other than a 4-chloro atom or a 4-methyl, 4-methoxy group or
4-nitro group) a hydrogen atom] and acid addition salts thereof.
The compounds of the invention possess insecticidal and acaricidal activity.
Preferred compounds according to the present invention, by virtue of their favourable insecticidal and acaricidal activity, include:
1,3-bis-(3-chlorophenyl)-2-trichloromethyl-imidazolidine and the acid addition salts thereof; and 1,3-bis-(3,5-dimethylphenyl)-2-trichloromethyl-imidazoIidine and the acid addition salts thereof.
The fo~owing non-limiting exampl~s illustrate the invention:-~ormu_ation Examples:
Example A
Sus~ension Powder ___ _____________ 0 parts by weight Qf 1,3~bis-(4-tolyl)-2-trichloromethyl~
imidazo]idine 8 " " " of sodium lignine sulfonate 2 '~ " " of sodium naphthaline sulfonate " " " of kaolin " " " of silicious chalk The components are mixed and milled by a pinned disk mill. The particle size of the product is approximately 2 to 6~u. The active ingredient cont~nt may be increased by decreasing the carriers and~may amount to approximately 80 parts by weight. For use, a spray with the desired concentration of active ingredient is made by mixing the latter with water; the concentration amounts in general to from 0.02 to 5% approximately.
Example B
Dusting_Powder 1.5 parts by weight of 1,3-bis-(3-chlorophenyl)-2~tri-chloromethyl-imidazolidine 98.0 parts by weight of talcum , lla~sl4, 0.5 parts by weight of aluminium stearate The active ingredient is milled using a pinned disk mill and mixed with the remaining components.
Example C
Colloid Formulation:
20.0 parts by weight of 1,3-bis-(3-tolyl)-2-trichloro-methyl-imidazolidine 2.5 " " 1l . of ethoxylated isotridecanol poly~ycol-ether (wetting agent, emulsifier) . 2.5 " ll ll of ethoxylated coconLt fat alcohol polyglycolether (wetting agent, emulisifier) 1.5 " " " alkylphenol polyglycolether 73.5-" " " liquid n-parrafins The components are predispersed and subsequently milled using a glass bead mill; size of particles: < 2~. 20% of the particles being below 1.1~.
Example D
Aerosol .5 parts by weight of 1,3-bis-(4-tolyl)-2-trichloromethyl-imidazoLidine.
35.0 " " " of talcum 0.5 " " " of zinc stearate 0.5 " " " of hexadecyl alcohol 63~5 " " " of propellant (Frigene) ~lQ~514 .
Propane/butane, nitrogen, carbon dioxide or air may also be used as the propellant instead of Frigene.
110~5~4 Example 1 a) N,N'-Bis-(3-chlorophenyl)-ethylenediamine - 188 g of ethylene bromide, 383 g of 3-chloroaniline and 300 g of sodium carbonate are stirred for 5 hours at 140C. After cooling to approx;mately 80C the inorganic substances are dissolved by the addition of water. The mixture is extracted with ethyl acetate and the organic extract is dr;ed with sodium sulfate~
Solvent and excess 3-chloro-aniline are distilled off - in vacuo. The remaining residue m~y be further processed directly according to conventional methods; the residue can also be distilled at 16 mm Hg and approx. 285C.
The crude yield amounts to 215 g (76% of theory).
b) 1,3-Bis-(3-chlorophenyl)-2-trichloro-methyl-imidazolidine 112.4 g of N,N'-bis(3-chlorophenyl~ethylenediamine in 500 ml of benzene are heated for 6 hours with 100 g of chloral on a water-separator, together with 10 g of ~-toluenesulfonic acid . Subsequently, the mixture is evaporated in vacuo as far as possible and the residue is taken up in 100 ml of glacial acetic acid while heating. After cooling crystallization begins.
The product is filtered off with suction, first washed with a little cold glacial acetic acid and then with ice-cold methanol. After drying 115 g (70% of theory) of the product of m.p. 90C are obtained.
Example 2 a) N,N'-Bis-(4-tolyl)-_thylenediimine 18 g of a 40% glyoxal solution in water are added dropwise to a refluxing solution of 27 g of ~-toluidine in 225 ml of methanol. During the addition of the glyoxal the Schiff base begins to precipitate. After the addition has been completed, the mixture is stirred for 15 minutes without heating and after cooling it is filtered off with suction. The filter r'esidue is washed wi~h methanol and dried. The yield of the product amounts to 25 g (86% of theory), m.p. 168C.
b) N ,N ' -Bis- (4-tolyl) -e~ylenediamine 19 g of the Schiff base are'hydrogenated in 500 ml of ethanol in the presence of Raney-nickel at 10 atmospheres pressure. After f`iltering off the catalyst with suction, the solvent'is evaporated in vacuo and the residue is suspended in petroleum ether, whereby a white crystalline substance is formed. After filtering off with suction and drying, the product shows a melting point of 94C.
The yield amounts to 15.2 g (80% of theory).
c) 1 3 Bis-(4 tol 1)-2-trichloromet l-imidazolidine _ = y hy 4.8 g of the hydrogenation product are dissolved in 10 ml of glacial acetic acid and mixed dropwise at room temperature with a solution of 6.0 g of chloral in 5 ml of glacial acetic acid. After standing for several hours crystallization begins. The next day the crystals are filtered off with suction and treated with cold methanol. After filtering off with suction a second precipitate can be obtained by the addition of water to the mother liquor. Ethanol or a methanol/
benzene mixture are suitable for recrystallization.
Melting point: 138C.
Yield: 5.5 g (74% of theory).
llQ~5~4 The following compounds of formula I can be synthesized according to the process described in the above - ~xamples:-Example No.UTH-No~ R1 R2Melting Point .. ' ~
3 727 H ll 138 4 ~ 1180 3-CH3 H 132 S W 1512 4-F H . 119 6 117~ 4-Cl H 172 7 W 1735 ~-Br H 164 1462 4-0C2H5 H ~ 128 14 1447 3-Cl ,5-Cl 197 17 1558 3-Br 4-CH3 167
The compounds of the invention possess insecticidal and acaricidal activity.
Preferred compounds according to the present invention, by virtue of their favourable insecticidal and acaricidal activity, include:
1,3-bis-(3-chlorophenyl)-2-trichloromethyl-imidazolidine and the acid addition salts thereof; and 1,3-bis-(3,5-dimethylphenyl)-2-trichloromethyl-imidazoIidine and the acid addition salts thereof.
The fo~owing non-limiting exampl~s illustrate the invention:-~ormu_ation Examples:
Example A
Sus~ension Powder ___ _____________ 0 parts by weight Qf 1,3~bis-(4-tolyl)-2-trichloromethyl~
imidazo]idine 8 " " " of sodium lignine sulfonate 2 '~ " " of sodium naphthaline sulfonate " " " of kaolin " " " of silicious chalk The components are mixed and milled by a pinned disk mill. The particle size of the product is approximately 2 to 6~u. The active ingredient cont~nt may be increased by decreasing the carriers and~may amount to approximately 80 parts by weight. For use, a spray with the desired concentration of active ingredient is made by mixing the latter with water; the concentration amounts in general to from 0.02 to 5% approximately.
Example B
Dusting_Powder 1.5 parts by weight of 1,3-bis-(3-chlorophenyl)-2~tri-chloromethyl-imidazolidine 98.0 parts by weight of talcum , lla~sl4, 0.5 parts by weight of aluminium stearate The active ingredient is milled using a pinned disk mill and mixed with the remaining components.
Example C
Colloid Formulation:
20.0 parts by weight of 1,3-bis-(3-tolyl)-2-trichloro-methyl-imidazolidine 2.5 " " 1l . of ethoxylated isotridecanol poly~ycol-ether (wetting agent, emulsifier) . 2.5 " ll ll of ethoxylated coconLt fat alcohol polyglycolether (wetting agent, emulisifier) 1.5 " " " alkylphenol polyglycolether 73.5-" " " liquid n-parrafins The components are predispersed and subsequently milled using a glass bead mill; size of particles: < 2~. 20% of the particles being below 1.1~.
Example D
Aerosol .5 parts by weight of 1,3-bis-(4-tolyl)-2-trichloromethyl-imidazoLidine.
35.0 " " " of talcum 0.5 " " " of zinc stearate 0.5 " " " of hexadecyl alcohol 63~5 " " " of propellant (Frigene) ~lQ~514 .
Propane/butane, nitrogen, carbon dioxide or air may also be used as the propellant instead of Frigene.
110~5~4 Example 1 a) N,N'-Bis-(3-chlorophenyl)-ethylenediamine - 188 g of ethylene bromide, 383 g of 3-chloroaniline and 300 g of sodium carbonate are stirred for 5 hours at 140C. After cooling to approx;mately 80C the inorganic substances are dissolved by the addition of water. The mixture is extracted with ethyl acetate and the organic extract is dr;ed with sodium sulfate~
Solvent and excess 3-chloro-aniline are distilled off - in vacuo. The remaining residue m~y be further processed directly according to conventional methods; the residue can also be distilled at 16 mm Hg and approx. 285C.
The crude yield amounts to 215 g (76% of theory).
b) 1,3-Bis-(3-chlorophenyl)-2-trichloro-methyl-imidazolidine 112.4 g of N,N'-bis(3-chlorophenyl~ethylenediamine in 500 ml of benzene are heated for 6 hours with 100 g of chloral on a water-separator, together with 10 g of ~-toluenesulfonic acid . Subsequently, the mixture is evaporated in vacuo as far as possible and the residue is taken up in 100 ml of glacial acetic acid while heating. After cooling crystallization begins.
The product is filtered off with suction, first washed with a little cold glacial acetic acid and then with ice-cold methanol. After drying 115 g (70% of theory) of the product of m.p. 90C are obtained.
Example 2 a) N,N'-Bis-(4-tolyl)-_thylenediimine 18 g of a 40% glyoxal solution in water are added dropwise to a refluxing solution of 27 g of ~-toluidine in 225 ml of methanol. During the addition of the glyoxal the Schiff base begins to precipitate. After the addition has been completed, the mixture is stirred for 15 minutes without heating and after cooling it is filtered off with suction. The filter r'esidue is washed wi~h methanol and dried. The yield of the product amounts to 25 g (86% of theory), m.p. 168C.
b) N ,N ' -Bis- (4-tolyl) -e~ylenediamine 19 g of the Schiff base are'hydrogenated in 500 ml of ethanol in the presence of Raney-nickel at 10 atmospheres pressure. After f`iltering off the catalyst with suction, the solvent'is evaporated in vacuo and the residue is suspended in petroleum ether, whereby a white crystalline substance is formed. After filtering off with suction and drying, the product shows a melting point of 94C.
The yield amounts to 15.2 g (80% of theory).
c) 1 3 Bis-(4 tol 1)-2-trichloromet l-imidazolidine _ = y hy 4.8 g of the hydrogenation product are dissolved in 10 ml of glacial acetic acid and mixed dropwise at room temperature with a solution of 6.0 g of chloral in 5 ml of glacial acetic acid. After standing for several hours crystallization begins. The next day the crystals are filtered off with suction and treated with cold methanol. After filtering off with suction a second precipitate can be obtained by the addition of water to the mother liquor. Ethanol or a methanol/
benzene mixture are suitable for recrystallization.
Melting point: 138C.
Yield: 5.5 g (74% of theory).
llQ~5~4 The following compounds of formula I can be synthesized according to the process described in the above - ~xamples:-Example No.UTH-No~ R1 R2Melting Point .. ' ~
3 727 H ll 138 4 ~ 1180 3-CH3 H 132 S W 1512 4-F H . 119 6 117~ 4-Cl H 172 7 W 1735 ~-Br H 164 1462 4-0C2H5 H ~ 128 14 1447 3-Cl ,5-Cl 197 17 1558 3-Br 4-CH3 167
Claims (14)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A compound of the general formula:
I
wherein R1 and R2 are in the 3-, 4- or 5-positions and R2 represents a halogen atom or a nitro, lower alkyl or alkoxy group and R1 represents a halogen atom or a nitro, lower alkyl or alkoxy group or (where R2 is other than a 4-chloro atom or a 4-methyl, 4-methoxy or 4-nitro group) a hydrogen atom, or an acid addition salt thereof.
I
wherein R1 and R2 are in the 3-, 4- or 5-positions and R2 represents a halogen atom or a nitro, lower alkyl or alkoxy group and R1 represents a halogen atom or a nitro, lower alkyl or alkoxy group or (where R2 is other than a 4-chloro atom or a 4-methyl, 4-methoxy or 4-nitro group) a hydrogen atom, or an acid addition salt thereof.
2. A compound as claimed in claim 1 wherein R1 and R2, which may be the same or different, each represents a chlorine or bromine atom or an alkyl or alkoxy group with 1 or 2 carbon atoms.
3. A compound as claimed in claim 2 wherein R1 and R2 are in 3- or 5-positions.
4. A compound as claimed in claim 1 wherein R2 represents a 3- or 5-chlorine atom or a 3- or 5-methyl group.
5. A compound as claimed in claim 4 wherein R1 represents a hydrogen or chlorine atom or a methyl group.
6. 1,3-Bis-(3-chlorophenyl)-2-trichloromethyl-imidazolidine and acid addition salts thereof.
7. 1,3-Bis-(3,5-dimethylphenyl)-2-trichloromethyl-imidazolidine and acid addition salts thereof.
8. A method of preventing or inhibiting the growth or proliferation of insects and/or acarids which comprises applying to a site infested with or susceptible to infestation by insects and/or acarids an effective amount of a compound of formula I as defined in claim 1 or an acid addition salt there-of.
9. A process for the preparation of compounds of formula I as defined in claim 1, or an acid addition salt thereof, which comprises reacting a compound of the formula:
II
(wherein R1 and R2 are as defined in claim 1) with a compound of the formula:
OHC-CCl3 III
whereby a compound of formula I is obtained and, if desired, subsequently converting the compound of formula I thus obtained into an acid addition salt thereof.
II
(wherein R1 and R2 are as defined in claim 1) with a compound of the formula:
OHC-CCl3 III
whereby a compound of formula I is obtained and, if desired, subsequently converting the compound of formula I thus obtained into an acid addition salt thereof.
10. A process as claimed in claim 9 wherein water formed in the reaction is removed by azeotropic distillation with a substantially water immiscible solvent.
11. A process as claimed in claim 10 wherein the substantially water immiscible solvent comprises benzene, toluene or xylene.
12. A process as claimed in claim 10 wherein the reaction is effected in the presence of an acidic catalyst.
13. A process as claimed in claim 12 wherein the acidic catalyst comprises p-toluene sulfonic acid.
14. A process as claimed in either claim 10 or 11 wherein a 3-substituted or 3,5-disubstituted compound of formula II is used.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2263239A DE2263239C3 (en) | 1972-12-23 | 1972-12-23 | New derivatives of 2-trichloromethylimidazolidine, their preparation and insecticidal and acaricidal agents containing them |
| DEP2263239.9 | 1972-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1100514A true CA1100514A (en) | 1981-05-05 |
Family
ID=5865348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA188,750A Expired CA1100514A (en) | 1972-12-23 | 1973-12-21 | Imidazolidine derivatives useful as insecticides and acaricides |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5820921B2 (en) |
| BE (1) | BE809042A (en) |
| CA (1) | CA1100514A (en) |
| CH (1) | CH587827A5 (en) |
| CS (1) | CS165314B2 (en) |
| DD (2) | DD114606A5 (en) |
| DE (1) | DE2263239C3 (en) |
| FR (1) | FR2211183B1 (en) |
| GB (1) | GB1444600A (en) |
| HU (1) | HU167236B (en) |
| IL (1) | IL43887A (en) |
| IT (1) | IT1048292B (en) |
| NL (1) | NL7317576A (en) |
| SU (1) | SU547170A3 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2508715A1 (en) * | 1975-02-28 | 1976-09-09 | Celamerck Gmbh & Co Kg | INSECTICIDAL AND ACARICIDAL ACTIVE SUBSTANCES AND THEIR USES |
-
1972
- 1972-12-23 DE DE2263239A patent/DE2263239C3/en not_active Expired
-
1973
- 1973-12-13 SU SU1979274A patent/SU547170A3/en active
- 1973-12-20 GB GB5919373A patent/GB1444600A/en not_active Expired
- 1973-12-20 CH CH1792873A patent/CH587827A5/xx not_active IP Right Cessation
- 1973-12-21 BE BE139228A patent/BE809042A/en not_active IP Right Cessation
- 1973-12-21 CA CA188,750A patent/CA1100514A/en not_active Expired
- 1973-12-21 HU HUCE981A patent/HU167236B/hu unknown
- 1973-12-21 JP JP744694A patent/JPS5820921B2/en not_active Expired
- 1973-12-21 DD DD182319*A patent/DD114606A5/xx unknown
- 1973-12-21 NL NL7317576A patent/NL7317576A/xx not_active Application Discontinuation
- 1973-12-21 FR FR7346115A patent/FR2211183B1/fr not_active Expired
- 1973-12-21 IT IT54552/73A patent/IT1048292B/en active
- 1973-12-21 DD DD175607A patent/DD110162A5/xx unknown
- 1973-12-21 IL IL43887A patent/IL43887A/en unknown
- 1973-12-21 CS CS8908A patent/CS165314B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE809042A (en) | 1974-06-21 |
| SU547170A3 (en) | 1977-02-15 |
| IL43887A0 (en) | 1974-03-14 |
| DD114606A5 (en) | 1975-08-12 |
| CH587827A5 (en) | 1977-05-13 |
| GB1444600A (en) | 1976-08-04 |
| JPS5820921B2 (en) | 1983-04-26 |
| DD110162A5 (en) | 1974-12-12 |
| FR2211183A1 (en) | 1974-07-19 |
| DE2263239C3 (en) | 1982-02-25 |
| IL43887A (en) | 1977-05-31 |
| CS165314B2 (en) | 1975-12-22 |
| DE2263239A1 (en) | 1974-06-27 |
| NL7317576A (en) | 1974-06-25 |
| HU167236B (en) | 1975-09-27 |
| FR2211183B1 (en) | 1978-12-01 |
| JPS4994836A (en) | 1974-09-09 |
| IT1048292B (en) | 1980-11-20 |
| DE2263239B2 (en) | 1981-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |