CA1053244A - Imides - Google Patents
ImidesInfo
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- CA1053244A CA1053244A CA195,418A CA195418A CA1053244A CA 1053244 A CA1053244 A CA 1053244A CA 195418 A CA195418 A CA 195418A CA 1053244 A CA1053244 A CA 1053244A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
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- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
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- Plural Heterocyclic Compounds (AREA)
Abstract
A B S T R A C T
of the Disclosure New dicarboximides of the formula
of the Disclosure New dicarboximides of the formula
Description
105;~Z4~
The present invention relates to dicarboxinides, to processes for their preparation, and to their use for the control of insects.
The dicarboximides correspond to the formula O
~ N-R (I) wherein o R represents a phenyl mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, iodine, trifluoromethyl, nitro, cyano, Cl-C4-alkyl, methoxy or methylthio, or monosubstituted by a methylenedioxy group, and Zl and Z2 each represent hydrogen, or together with the carbon atoms to which they are bound they -represent a carbon-carbon bond.
As substltuents of the phenyl group, the Cl~C4-alkyl groups can be branched-chain or straight-chain, and are preferably the methyl or ethyl group.
Compounds of formula I preferred by virtue of their action are those wherein R represents a phenyl mono- to trisubstituted9 identically or differently, by fluorine, chlorine, ~ .
' ~ ~ ' ' ' ' ', '' .: ' . ~' .
1~53Z9t4 bromine, iodine, trifluoromethyl, methyl, ethyl, methoxy, methylthio, nitro, or cyano, or monosubstituted by a methylenedioxy group, and Zl and Z2 each represent hydrogen, or together with the carbon atoms to which they are bound they represent a carbon-carbon bond.
Paritcularly preferred compounds of formula I are those wherein R represents a phenyl mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, iodine, trifluoromethyl, ethyl, methyl, methylthio, nitro or cyano, or monosubstituted by a methylenedioxy group, and Zl and Z2 together with the carbon atoms to which they are bound re-present a carbon-carbon bond.
The present invention also relates to a process for the preparation of compounds of the formula ~ / - R
wherein R represents a phenyl mono- to trisubstituted, identically or different-ly, by fluorine, chlorine, bromine, iodine, trifluoromethyl, nitro, cyano, Cl-C4-alkyl, thoxy or methylthio, or mono substituted by a methylene dioxy group, and Zl and Z2 each represent hydrogen, or together with the carbon atoms to which they are bound they ~represent a carbon-carbon bond5 in which process a compound of the formula <~X\
o ' ~' is reacted _ 3 - ~:
~.. . :...
~)S;~Z44 with a compound of the formula wherein R, Zl and Z2 have the meanings given for formula I.
The reaction is performed under normal pressur~, at a temperature of 60 - 150C, preferably 80 - 120C, and in a high-boiling solvent, such as, e.g. glacial acetic acid, benzene, toluene or xylene.
The starting materials of formula II are known, and can be prepared by a method analogous to that described in Ber. 86, 1528-39 (1953).
The compounds of formula I are suitable for the control of insects. To be particularly emphasised is their high degree of effectiveness against Lepidoptera.
In the U S Patent Specifications Nos. 2,462,835 and
The present invention relates to dicarboxinides, to processes for their preparation, and to their use for the control of insects.
The dicarboximides correspond to the formula O
~ N-R (I) wherein o R represents a phenyl mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, iodine, trifluoromethyl, nitro, cyano, Cl-C4-alkyl, methoxy or methylthio, or monosubstituted by a methylenedioxy group, and Zl and Z2 each represent hydrogen, or together with the carbon atoms to which they are bound they -represent a carbon-carbon bond.
As substltuents of the phenyl group, the Cl~C4-alkyl groups can be branched-chain or straight-chain, and are preferably the methyl or ethyl group.
Compounds of formula I preferred by virtue of their action are those wherein R represents a phenyl mono- to trisubstituted9 identically or differently, by fluorine, chlorine, ~ .
' ~ ~ ' ' ' ' ', '' .: ' . ~' .
1~53Z9t4 bromine, iodine, trifluoromethyl, methyl, ethyl, methoxy, methylthio, nitro, or cyano, or monosubstituted by a methylenedioxy group, and Zl and Z2 each represent hydrogen, or together with the carbon atoms to which they are bound they represent a carbon-carbon bond.
Paritcularly preferred compounds of formula I are those wherein R represents a phenyl mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, iodine, trifluoromethyl, ethyl, methyl, methylthio, nitro or cyano, or monosubstituted by a methylenedioxy group, and Zl and Z2 together with the carbon atoms to which they are bound re-present a carbon-carbon bond.
The present invention also relates to a process for the preparation of compounds of the formula ~ / - R
wherein R represents a phenyl mono- to trisubstituted, identically or different-ly, by fluorine, chlorine, bromine, iodine, trifluoromethyl, nitro, cyano, Cl-C4-alkyl, thoxy or methylthio, or mono substituted by a methylene dioxy group, and Zl and Z2 each represent hydrogen, or together with the carbon atoms to which they are bound they ~represent a carbon-carbon bond5 in which process a compound of the formula <~X\
o ' ~' is reacted _ 3 - ~:
~.. . :...
~)S;~Z44 with a compound of the formula wherein R, Zl and Z2 have the meanings given for formula I.
The reaction is performed under normal pressur~, at a temperature of 60 - 150C, preferably 80 - 120C, and in a high-boiling solvent, such as, e.g. glacial acetic acid, benzene, toluene or xylene.
The starting materials of formula II are known, and can be prepared by a method analogous to that described in Ber. 86, 1528-39 (1953).
The compounds of formula I are suitable for the control of insects. To be particularly emphasised is their high degree of effectiveness against Lepidoptera.
In the U S Patent Specifications Nos. 2,462,835 and
2,545,283, dicarboximides are described as synergists.
Reference is made to, inter alia, their insecticidal action.
The insecticidal, herbicidal and fungicidal action of dicarboximides is described in the U S Patent Specification No. 3,654,302.
Compared with the compounds described in the above-mentioned patent specifications, the dicarboximides of formula I exhibit an unexpectedly better larvicidal action, especially in the case of larvae of Lepidoptera.
_ 4 _ .
1(~53;~44 The insecticidal action of the dicarboximides of formula I can be appreciably broadened and adapted to suit given circumstances by the addition of other insecticides. Suitable additives are, for example:
organic phosphorous compounds~
nitrophenols and derivatives thereof, formamidines, carbamates and chlorinated hydrocarbons.
~0 5 3Z ~ ~
The compo~mds of formula I can be used on their own or ~ogcther with suitable carriers and/or additives.
Suitable carriers and additives may be solid or liquid, and they correspond to the substances common in forrnulation practice, such as, e.g. natural or regenerated substances, solvents, dispersing agents, wetting agents, adhesives, thickeners, binders and/or fertilisers.
For application, the compo~mds of formula I can be processed into the form of dusts, emulsion concentrates, granulates, dispersions, sprays or solutions, the formulation of these preparations being e~fected in a manner commonly kno~n in practice. Also to be mentioned are cattle dips and spray races, in which aqueous preparations are used. - -The agents according to the invention are prepared in a manner known per se by the intimate mixing and/or grinding of active substances of formula I with suitable carrlers, optionally with the addition of dispersing agents or solvents which are inert to the active substances. The active substances can be obtained and used in the following forms:
_ Ld ions:- dusts, scattering agents, granulates, coated granulates, impregnated granulates and homogeneous granulates;
~ (~53Z44 liquid preparat;ons:-a) water-dispersible active-substance concentrates:
wettable powders, pastes or emulsions;
b~ solutions.
The content of active substance in the described agents is between 0.1 and 95 %.
The active substances of ormula I can be formulated, for example, as follows:
Dusts:
The following substances are used in the preparation of a) a 5% dust, and b) a 2% dust:
a) 5 parts of active substance, 9S parts of talcum;
b) 2 parts of active substance, 1 part of highly dispersed silicic acid, 97 parts of talcum.
The active substances are mixed and ground with the carriers.
11~53Z44 Granula~e:
Tlle followlng subs~ances are used to prepare a 5% granulate:
S par~s o active substance, 0.25 part of epichlorohydrin, 0.25 part of cetyl polyglycol ether,
Reference is made to, inter alia, their insecticidal action.
The insecticidal, herbicidal and fungicidal action of dicarboximides is described in the U S Patent Specification No. 3,654,302.
Compared with the compounds described in the above-mentioned patent specifications, the dicarboximides of formula I exhibit an unexpectedly better larvicidal action, especially in the case of larvae of Lepidoptera.
_ 4 _ .
1(~53;~44 The insecticidal action of the dicarboximides of formula I can be appreciably broadened and adapted to suit given circumstances by the addition of other insecticides. Suitable additives are, for example:
organic phosphorous compounds~
nitrophenols and derivatives thereof, formamidines, carbamates and chlorinated hydrocarbons.
~0 5 3Z ~ ~
The compo~mds of formula I can be used on their own or ~ogcther with suitable carriers and/or additives.
Suitable carriers and additives may be solid or liquid, and they correspond to the substances common in forrnulation practice, such as, e.g. natural or regenerated substances, solvents, dispersing agents, wetting agents, adhesives, thickeners, binders and/or fertilisers.
For application, the compo~mds of formula I can be processed into the form of dusts, emulsion concentrates, granulates, dispersions, sprays or solutions, the formulation of these preparations being e~fected in a manner commonly kno~n in practice. Also to be mentioned are cattle dips and spray races, in which aqueous preparations are used. - -The agents according to the invention are prepared in a manner known per se by the intimate mixing and/or grinding of active substances of formula I with suitable carrlers, optionally with the addition of dispersing agents or solvents which are inert to the active substances. The active substances can be obtained and used in the following forms:
_ Ld ions:- dusts, scattering agents, granulates, coated granulates, impregnated granulates and homogeneous granulates;
~ (~53Z44 liquid preparat;ons:-a) water-dispersible active-substance concentrates:
wettable powders, pastes or emulsions;
b~ solutions.
The content of active substance in the described agents is between 0.1 and 95 %.
The active substances of ormula I can be formulated, for example, as follows:
Dusts:
The following substances are used in the preparation of a) a 5% dust, and b) a 2% dust:
a) 5 parts of active substance, 9S parts of talcum;
b) 2 parts of active substance, 1 part of highly dispersed silicic acid, 97 parts of talcum.
The active substances are mixed and ground with the carriers.
11~53Z44 Granula~e:
Tlle followlng subs~ances are used to prepare a 5% granulate:
S par~s o active substance, 0.25 part of epichlorohydrin, 0.25 part of cetyl polyglycol ether,
3.50 parts o polye~hylene glycol, 91 parts of kaolin (particle size 0.3 - 0.8 mm).
The active substance is mixed with epichlorohydrin and dissolved with 6 parts of acetone; the polyethylene 10 glycol and cetyl polyglycol ether are then added. The solution thus obtained is sprayed onto kaolin, and the acetone subsequently evaporated off in vacuo.
Wettable powder:
The follo~ing constituents are used for the preparation of a) a 40%, b) and c) a 25%, and d) a 10% wettable powder:
a) 40 parts of active substance, parts of sodiun lignin sulphonate, 1 part of sodium dibutyl~naphthalene sulphonate, 54 parts of silicic acid;
20 b) 25 parts of active substance,
The active substance is mixed with epichlorohydrin and dissolved with 6 parts of acetone; the polyethylene 10 glycol and cetyl polyglycol ether are then added. The solution thus obtained is sprayed onto kaolin, and the acetone subsequently evaporated off in vacuo.
Wettable powder:
The follo~ing constituents are used for the preparation of a) a 40%, b) and c) a 25%, and d) a 10% wettable powder:
a) 40 parts of active substance, parts of sodiun lignin sulphonate, 1 part of sodium dibutyl~naphthalene sulphonate, 54 parts of silicic acid;
20 b) 25 parts of active substance,
4,5 parts of calcium lignin sulphonate, 1.9 parts of Champagne chalk/hydroxyethyl cellulose mix~ure (1:1), 1.5 parts of soclium dibutyl naphthalene sulphonate, 19.5 parts of silicic acid, : .. - ~. ' ' : .' 19.5 parts of Champagne chalk, 28.1 parts of kaolin;
c) 25 par~s of active substance~
2.5 parts of isooctylphenoxy polyoxyethylene-ethanol, S 1.7 parts of Clampagne chalk/hydroxyethyl cellulose mixture (1:1), 8.3 parts of sodium aluminium silicate, 16.5 parts of kieselguhr, 46 parts of kaolin;
d) 10 ?arts of active substance, 3 parts of a mixture of the sodium salts of saturated fatty alcohol sulphates, Sparts of naphthalenesulphonic acid/formaldehyde condensate, .15 82parts of kaolin.
The active substances are intimately mixed~ in suitable mixers, with the additives, the mixture being then ground in the appropriate mills and rollers. ~ettable powders are obtained which can be diluted with water to give suspensions of any desired concentration~
Emulsifiable concentrates:
The.following substances are used to prepare a) a 10%
and b) a 25% emulsifiable concentrate: . -a) 10 parts of active substance, 3,4 parts of epoxidised vegetable oi.l, . 9 .
. .
IL(~5;~4 3..4 par~s of a combination emulsifier consisting oE f~ty alcohol polyglycol e~her and alkylaryl-sulpllonate calcium salt, 40 parts of dimethylformamide5 43.2 parts of xylene;
b) 25 parts of active substance, 2.5 parts of epoxidised vege~able oil, 10 parts of an alkylarylsulphonate/fatty alcohol polyglycol ether mixture,
c) 25 par~s of active substance~
2.5 parts of isooctylphenoxy polyoxyethylene-ethanol, S 1.7 parts of Clampagne chalk/hydroxyethyl cellulose mixture (1:1), 8.3 parts of sodium aluminium silicate, 16.5 parts of kieselguhr, 46 parts of kaolin;
d) 10 ?arts of active substance, 3 parts of a mixture of the sodium salts of saturated fatty alcohol sulphates, Sparts of naphthalenesulphonic acid/formaldehyde condensate, .15 82parts of kaolin.
The active substances are intimately mixed~ in suitable mixers, with the additives, the mixture being then ground in the appropriate mills and rollers. ~ettable powders are obtained which can be diluted with water to give suspensions of any desired concentration~
Emulsifiable concentrates:
The.following substances are used to prepare a) a 10%
and b) a 25% emulsifiable concentrate: . -a) 10 parts of active substance, 3,4 parts of epoxidised vegetable oi.l, . 9 .
. .
IL(~5;~4 3..4 par~s of a combination emulsifier consisting oE f~ty alcohol polyglycol e~her and alkylaryl-sulpllonate calcium salt, 40 parts of dimethylformamide5 43.2 parts of xylene;
b) 25 parts of active substance, 2.5 parts of epoxidised vege~able oil, 10 parts of an alkylarylsulphonate/fatty alcohol polyglycol ether mixture,
5 parts of dimethylformamide, 57.5 par~s of xylene.
From these concentrates it is possible to prepare~ .-by dilution with water, emulsions of any desired concen.tration.
, ~:
The following constituents are used to prepare a 5% spray:
S parts of active substance, 1 part of epichlorhydrin, 94 parts of ligroin (boiling limits 160 - 190C).
. .
. .
l(~S3244 Exampl e 1 a) ~ r ~ion of N-(4'-nitrophen~ tricyclo-[4.2.2.02-4]-non-8-ene-6`7-dicarboximide.
_ _ _ _ _ _ _ _ _ _ _ . _ . _ _ _ . _ _ _ 250 g of tricyclo-[4.2.2.02-4]-non-8-ene-6,7-dicarboxylic acid anhydride (prepared from cycloheptatriene and m~leic acid anhydride, K. ~lder, Ber. 86, 1528-39 (1953)) and 200 g of 4-nitroaniline are refluxed in 1500 ml of glacial acetic acid for 3 hours. The reaction mixture cooled to 60C is poured into 2000 ml of hot water, whereupon the crude product precipitates. After cooling, the crude product is filtered off, dried, and recrystallised from ethyl acetate; M.P. 210 - 212C.
b) Preparation of N-(3',5'-dichlorophenYl)-tricyclo-l4.2.2. o2 4 ~ -nonane-6~7-dicarboximide.
__ .
19.2 g of tricyclo-[4.2.2.02 4l-nonane-6,7-dicarboxylic acid anhydride (prepared from the cycloheptatriene/maleic acid anhydride adduct (see Ex. la) by catalytic hydrogenation, K. Alder, Ber. 86, 1528-39 (1953) and 19.4 g of 3,5-dichloroaniline are refluxed in 1000 ml of toluene for 16 hours, whereby the water orming during the reaction is separated with a water separator. After cooling, the toluene is removed in vacuum, and the residue recrystallised from ethyl acetate, M.P. 145 - 153C.
- . . . . ~ .
~;
105~2~4 The following addi~ional compounds are prepared in an analogous manner:
o/
.. ~ .
_ _ R= _ M.P ~C _ 3,4-dichlo,ophenyl 204 - 206C
4-bromophenyl 206 - 207C
~-fluorophenyl 184C
4-chlorophenyl 203C
3-txi~lu~romethyl-phenyl 20GC
3-methylthio-phenyl 186 - 188C
3,5-dichlorophenyl 167 - 169C
2,4,5-trichlorophenyl 168 - 170C
275-dibromophenyl 191 - 192C
2,5-dichlorophenyl 195 - 196C
3-chlorophenyl 182 - 183C
3-nitrophenyl 204 - 206C .-. 3,5-bis~trifluoromethyl-phenyl 100 - 101C
. 2-chloro-5-trifluoromethyl-phenyl 126 - 127C
2-ethyl-phenyl ` 152 ~ 154C
. 4-cyano-phenyl 190 - 191C .
202-methyl-4-chlorophenyl 179 - 180C
. .... .. ~ . ,. __ '. -' ',. ' ,. ,. ' " ' , ' . , :
1053Z4~
R= _ _ M.P. C~
2-methyl-5-chlorophenyl 184 - 190C :
3-trifluorclnethyl-4-chlorophenyl 189 - 190C
2-methyl-5-nitrophenyl 189 - 190C
2-nitrophenyl 168 - 170C
4-methoxy-phenyl 198 - 200C
2-fluorophenyl 148 - 149C
3-fluorophenyl 152 - 154C
2-iodophenyl 149 - lSlC
4-iodophenyl 216 - 218C
2-chloro-4-bromophenyl 208 - 210C
2,5-dimethoxy-4-chlorophenyl 196 - 198C
4-methylthio-phenyl 186 - 188C
. 3,5-dinitro-phenyl 178 - 180C
2-nitro-4-methyl-phenyl 202 - 204C
. 2,4-dichlorophenyl . 162 - 164C
2-trifluoromethyl-phenyl 128C
: 2-methyl-3-chlorophenyl 157C
3,4-methylenedioxy-phenyl 217C
4-trifluoromethylphenyl 218C
.
..... . ..
~0532~
.
~o~
_ R-- M.P. C
. _ _ 2-methoxy-4-ohlorophenyl 170C
2,4-dibromophenyl 207C
2,4-difluorophenyl 135C
.5 2,5-difluorophenyl 135C
2-methyl-4-bromophenyl 198C
3-fluoro-4-methyl-phenyl 202C
3-bromo-5-trifluoromethyl-phenyl 141C
3,4,5-trichlorophenyl 186 - 187C
2-methyl-3-nitrophenyl 210C
~0S3;~
<¦ ~ N--R
R- M . P . C
, 4-bromophenyl 230 - 240C
2-chloro-5-trifllloromethyl-phenyl 157C
2,4-dichlorophenyL 175C
Exa~ 2 105;~244 -tSecticLdal action a~ains~ Spodoptera littoralis Cotton plants 15 cm in height were sprayed with 25 ml of a solu~ion (acetone/~ater 1:1) containing 0.2%
of active substance. After drying of the coating~ 5 Spodoptera littoralis caterpillars (L3 stage) were placed on each plant. A plastic cylinder was put over the plant and closed with a copper gauze lid. A mortality determination was made after 2 days. The compounds according to Example 1 exhibited in ~his test a good action against Spodoptera littoralis.
Example 3 Insecticidal action aga]nst Lep~inotarsa decemlineata Potato plants 15 cm in height were sprayed with 25 ml o a solution (acetone/water 1:1) containing 0.1% of active substance. After drying o~ the coating, 10 Leptinotarsa larvae (L3 stage) were placed on each plant.
A plastic cylinder was put over the plant and closed with a copper gauze lid. A mortality evaluation was made a~ter 2 days.
The compounds according to Example 1 exhibited in this test a good action against Leptinotarsa decemlineata.
~ .
, .
. ~ - , . . . . . , . . . . ., ... -'.' . ~'; ,,i ' , .
From these concentrates it is possible to prepare~ .-by dilution with water, emulsions of any desired concen.tration.
, ~:
The following constituents are used to prepare a 5% spray:
S parts of active substance, 1 part of epichlorhydrin, 94 parts of ligroin (boiling limits 160 - 190C).
. .
. .
l(~S3244 Exampl e 1 a) ~ r ~ion of N-(4'-nitrophen~ tricyclo-[4.2.2.02-4]-non-8-ene-6`7-dicarboximide.
_ _ _ _ _ _ _ _ _ _ _ . _ . _ _ _ . _ _ _ 250 g of tricyclo-[4.2.2.02-4]-non-8-ene-6,7-dicarboxylic acid anhydride (prepared from cycloheptatriene and m~leic acid anhydride, K. ~lder, Ber. 86, 1528-39 (1953)) and 200 g of 4-nitroaniline are refluxed in 1500 ml of glacial acetic acid for 3 hours. The reaction mixture cooled to 60C is poured into 2000 ml of hot water, whereupon the crude product precipitates. After cooling, the crude product is filtered off, dried, and recrystallised from ethyl acetate; M.P. 210 - 212C.
b) Preparation of N-(3',5'-dichlorophenYl)-tricyclo-l4.2.2. o2 4 ~ -nonane-6~7-dicarboximide.
__ .
19.2 g of tricyclo-[4.2.2.02 4l-nonane-6,7-dicarboxylic acid anhydride (prepared from the cycloheptatriene/maleic acid anhydride adduct (see Ex. la) by catalytic hydrogenation, K. Alder, Ber. 86, 1528-39 (1953) and 19.4 g of 3,5-dichloroaniline are refluxed in 1000 ml of toluene for 16 hours, whereby the water orming during the reaction is separated with a water separator. After cooling, the toluene is removed in vacuum, and the residue recrystallised from ethyl acetate, M.P. 145 - 153C.
- . . . . ~ .
~;
105~2~4 The following addi~ional compounds are prepared in an analogous manner:
o/
.. ~ .
_ _ R= _ M.P ~C _ 3,4-dichlo,ophenyl 204 - 206C
4-bromophenyl 206 - 207C
~-fluorophenyl 184C
4-chlorophenyl 203C
3-txi~lu~romethyl-phenyl 20GC
3-methylthio-phenyl 186 - 188C
3,5-dichlorophenyl 167 - 169C
2,4,5-trichlorophenyl 168 - 170C
275-dibromophenyl 191 - 192C
2,5-dichlorophenyl 195 - 196C
3-chlorophenyl 182 - 183C
3-nitrophenyl 204 - 206C .-. 3,5-bis~trifluoromethyl-phenyl 100 - 101C
. 2-chloro-5-trifluoromethyl-phenyl 126 - 127C
2-ethyl-phenyl ` 152 ~ 154C
. 4-cyano-phenyl 190 - 191C .
202-methyl-4-chlorophenyl 179 - 180C
. .... .. ~ . ,. __ '. -' ',. ' ,. ,. ' " ' , ' . , :
1053Z4~
R= _ _ M.P. C~
2-methyl-5-chlorophenyl 184 - 190C :
3-trifluorclnethyl-4-chlorophenyl 189 - 190C
2-methyl-5-nitrophenyl 189 - 190C
2-nitrophenyl 168 - 170C
4-methoxy-phenyl 198 - 200C
2-fluorophenyl 148 - 149C
3-fluorophenyl 152 - 154C
2-iodophenyl 149 - lSlC
4-iodophenyl 216 - 218C
2-chloro-4-bromophenyl 208 - 210C
2,5-dimethoxy-4-chlorophenyl 196 - 198C
4-methylthio-phenyl 186 - 188C
. 3,5-dinitro-phenyl 178 - 180C
2-nitro-4-methyl-phenyl 202 - 204C
. 2,4-dichlorophenyl . 162 - 164C
2-trifluoromethyl-phenyl 128C
: 2-methyl-3-chlorophenyl 157C
3,4-methylenedioxy-phenyl 217C
4-trifluoromethylphenyl 218C
.
..... . ..
~0532~
.
~o~
_ R-- M.P. C
. _ _ 2-methoxy-4-ohlorophenyl 170C
2,4-dibromophenyl 207C
2,4-difluorophenyl 135C
.5 2,5-difluorophenyl 135C
2-methyl-4-bromophenyl 198C
3-fluoro-4-methyl-phenyl 202C
3-bromo-5-trifluoromethyl-phenyl 141C
3,4,5-trichlorophenyl 186 - 187C
2-methyl-3-nitrophenyl 210C
~0S3;~
<¦ ~ N--R
R- M . P . C
, 4-bromophenyl 230 - 240C
2-chloro-5-trifllloromethyl-phenyl 157C
2,4-dichlorophenyL 175C
Exa~ 2 105;~244 -tSecticLdal action a~ains~ Spodoptera littoralis Cotton plants 15 cm in height were sprayed with 25 ml of a solu~ion (acetone/~ater 1:1) containing 0.2%
of active substance. After drying of the coating~ 5 Spodoptera littoralis caterpillars (L3 stage) were placed on each plant. A plastic cylinder was put over the plant and closed with a copper gauze lid. A mortality determination was made after 2 days. The compounds according to Example 1 exhibited in ~his test a good action against Spodoptera littoralis.
Example 3 Insecticidal action aga]nst Lep~inotarsa decemlineata Potato plants 15 cm in height were sprayed with 25 ml o a solution (acetone/water 1:1) containing 0.1% of active substance. After drying o~ the coating, 10 Leptinotarsa larvae (L3 stage) were placed on each plant.
A plastic cylinder was put over the plant and closed with a copper gauze lid. A mortality evaluation was made a~ter 2 days.
The compounds according to Example 1 exhibited in this test a good action against Leptinotarsa decemlineata.
~ .
, .
. ~ - , . . . . . , . . . . ., ... -'.' . ~'; ,,i ' , .
Claims (14)
1. Compounds of the formula wherein R represents a phenyl mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, iodine, trifluoromethyl, nitro, cyano, C1-C4-alkyl, methoxy or methylthio, or monosubstituted by a methylenedioxy group, and Z1 and Z2 each represent hydrogen, or together with the carbon atoms to which they are bound they represent a carbon-carbon bond.
2. Compounds according to Claim 1 wherein R represents a phenyl mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, iodine, trifluoromethyl, methyl, ethyl, methoxy, methylthio, nitro or cyano, or mono-substituted by a methylenedioxy group, and Z1 and Z2 each represent hydrogen, or together with the carbon atoms to which they are bound they represent a carbon-carbon bond.
3. Compounds according to Claim 2 wherein R represents a phenyl mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, iodine, trifluoromethyl, methyl, ethyl, methylthio, nitro or cyano, or monosubstituted by a methylenedioxy group, and Z1 and Z2 together with the carbon atoms to which they are bound represent a carbon-carbon bond.
4. Compound according to Claim 3 of the formula .
5. Compound according to Claim 3 of the formula .
6. Compound according to Claim 3 of the formula
7. Compound according to Claim 3 of the formula
8. Compound according to Claim 3 of the formula
9. Compound according to Claim 3 of the formula
10. Compound according to Claim 3 of the formula
11. Compound according to Claim 3 of the formula
12. A process for the preparation of compounds of the formula wherein R represents a phenyl mono- to trisubstituted, identically or differently, by fluorine, chlorine, bromine, iodine, trifluoromethyl, nitro, cyano, C1-C4-alkyl, methoxy or methylthio, or monosubstituted by a methylene-dioxy group, and Z1 and Z2 each represent hydrogen, or together with the carbon atoms to which they are bound they represent a carbon-carbon bond, in which process a compound of the formula is reacted with a compound of the formula wherein R, Z1 and Z2 have the meanings given in claim 1.
13. Method of combatting insects on plants which comprises applying to the plants a compound according to claim 1.
14. Method according to claim 13 for the control of Lepidoptera.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH549773A CH576744A5 (en) | 1973-04-17 | 1973-04-17 | N-substd phenyl dicarboximides - insecticides useful against lepidoptera larvae, prepd. from an anhydride and an aniline |
| CH276574A CH591207A5 (en) | 1974-02-27 | 1974-02-27 | N-substd phenyl dicarboximides - insecticides useful against lepidoptera larvae, prepd. from an anhydride and an aniline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1053244A true CA1053244A (en) | 1979-04-24 |
Family
ID=25691347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA195,418A Expired CA1053244A (en) | 1973-04-17 | 1974-03-19 | Imides |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS505533A (en) |
| CA (1) | CA1053244A (en) |
| DD (1) | DD112889A5 (en) |
| DE (1) | DE2417839A1 (en) |
| FR (1) | FR2226397B1 (en) |
| GB (1) | GB1449538A (en) |
| IL (1) | IL44447A (en) |
| NL (1) | NL7404165A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4173646A (en) | 1974-10-04 | 1979-11-06 | Merck & Co., Inc. | Tricyclicdicarboximides |
| US4132799A (en) | 1975-05-09 | 1979-01-02 | Merck & Co., Inc. | N-(Benzoxazolinyl-2-one)-tricyclic dicarboximides |
| US4061763A (en) | 1975-05-09 | 1977-12-06 | Merck & Co., Inc. | Tricyclicdicarboximides |
| DE10348022A1 (en) * | 2003-10-15 | 2005-05-25 | Imtm Gmbh | New dipeptidyl peptidase IV inhibitors for the functional influence of different cells and for the treatment of immunological, inflammatory, neuronal and other diseases |
-
1974
- 1974-03-19 IL IL44447A patent/IL44447A/en unknown
- 1974-03-19 CA CA195,418A patent/CA1053244A/en not_active Expired
- 1974-03-27 NL NL7404165A patent/NL7404165A/xx not_active Application Discontinuation
- 1974-04-11 DE DE19742417839 patent/DE2417839A1/en not_active Withdrawn
- 1974-04-12 FR FR7412973A patent/FR2226397B1/fr not_active Expired
- 1974-04-16 GB GB1658174A patent/GB1449538A/en not_active Expired
- 1974-04-16 DD DD177936A patent/DD112889A5/xx unknown
- 1974-04-17 JP JP49043235A patent/JPS505533A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2226397B1 (en) | 1976-12-17 |
| IL44447A (en) | 1976-11-30 |
| JPS505533A (en) | 1975-01-21 |
| DE2417839A1 (en) | 1974-11-07 |
| NL7404165A (en) | 1974-10-21 |
| DD112889A5 (en) | 1975-05-12 |
| IL44447A0 (en) | 1974-06-30 |
| FR2226397A1 (en) | 1974-11-15 |
| GB1449538A (en) | 1976-09-15 |
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