DE3334224A1 - N-Benzoyl-N'-alkoxyphenylureas and their use for controlling insects and acarids - Google Patents
N-Benzoyl-N'-alkoxyphenylureas and their use for controlling insects and acaridsInfo
- Publication number
- DE3334224A1 DE3334224A1 DE19833334224 DE3334224A DE3334224A1 DE 3334224 A1 DE3334224 A1 DE 3334224A1 DE 19833334224 DE19833334224 DE 19833334224 DE 3334224 A DE3334224 A DE 3334224A DE 3334224 A1 DE3334224 A1 DE 3334224A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- benzoyl
- abovementioned meanings
- preparation
- insecticidal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
Abstract
Description
N-Benzoyl-N'-alkoxyphenylharnstoffe und ihre Verwendung zur BekämpfungN-Benzoyl-N'-alkoxyphenylureas and their use for combating
von Insekten und Akariden Die vorliegende Erfindung betrifft N-Benzoyl-N'-Benzoyl-N'-phenylharnstoffe, Verfahren zu ihrer Herstellung und insektizide Mittel, die diese Verbindungen als Wirkstoffe enthalten.of insects and acarids The present invention relates to N-benzoyl-N'-benzoyl-N'-phenylureas, Process for their preparation and insecticidal agents using these compounds as Contain active ingredients.
Es ist bekannt, daß N-Benzoyl-N'-phenylharnstoffe insektizid wirksam sind (DE-OS 2 123 236).It is known that N-benzoyl-N'-phenylureas have insecticidal properties are (DE-OS 2 123 236).
Es wurde gefunden, daß N-Benzoyl-N'-phenylharnstoffe der Formel in der X für F, Cl, oder H, Y für F, Cl, Br oder CR3> R1 und R2 (die gleich oder verschieden sein können) für H, F, C1, Br und R3 für einen Alkyl- oder Cycloalkylrest mit 2 - 13 Kohlenstoffatomen steht, insektizid sehr wirksam sind. Sie sind bekannten Benzoylharnstoffen ähnlicher Struktur in ihrer Wirkung überlegen.It has been found that N-benzoyl-N'-phenylureas of the formula in which X for F, Cl, or H, Y for F, Cl, Br or CR3> R1 and R2 (which can be identical or different) for H, F, C1, Br and R3 for an alkyl or cycloalkyl radical with 2 - 13 carbon atoms, insecticidal is very effective. They are superior to known benzoylureas with a similar structure in terms of their effect.
Als (Cyclo)-Alkylreste für R3 in Formel I kommen primäre, sekundäre und tertiäre Alkylreste mit 2 bis 13 C-Atomen oder Cycloalkylreste mit 4 bis 13 C-Atomen, wie Isopropyl, sec.-Butyl, Pentyl-(3), 2,4-Dimethyl--pentyl-(3), n-Heptyl, 2, 6-Dimethylheptyl-(4), 2,2,4,4-Tetramethyl--pentyl-(3), 1-Methyl-7-ethyl-nonyl-(4), 2, 8-Dimethyl-nonyl-(8), 3,5,5-Trimethyl-hexyl-(1), Ethyl, n-Propyl, n-Butyl, n-Pentyl, n-Hexyl, n-Dodecyl, 6,6, 4-Trimethylhexyl-(1), t-Butyl, 3-Ethylpentyl-(3), 2,2,5--Trimethylpentyl-( 1), Cyclobutyl, Cyclopentyl, Cyclohexyl, 1-Methylcyclohexyl, Cyclohexylmethyl oder Dicyclohexylmethyl in Betracht.The (cyclo) -alkyl radicals for R3 in formula I are primary, secondary and tertiary alkyl radicals with 2 to 13 carbon atoms or cycloalkyl radicals with 4 to 13 C atoms, such as isopropyl, sec-butyl, pentyl (3), 2,4-dimethyl - pentyl (3), n-heptyl, 2,6-Dimethylheptyl- (4), 2,2,4,4-tetramethyl-pentyl- (3), 1-methyl-7-ethyl-nonyl- (4), 2, 8-dimethyl-nonyl- (8), 3,5,5-trimethyl-hexyl- (1), ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-dodecyl, 6,6, 4-trimethylhexyl- (1), t-butyl, 3-ethylpentyl- (3), 2,2,5-trimethylpentyl- ( 1), cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcyclohexyl, cyclohexylmethyl or Dicyclohexylmethyl into consideration.
Bevorzugte N-Benzoyl-N'-phenylharnstoffe sind Verbindungen der Formel I, in der X Fluor oder Chlor und Y Fluor oder Wasserstoff bedeuten. R3 ist vorzugsweise ein verzweigter Alkylrest mit sekundär oder tertiär gebundenem Kohlenstoff mit 4 bis 9 Kohlenstoffatomen.Preferred N-benzoyl-N'-phenylureas are compounds of the formula I, in which X is fluorine or chlorine and Y is fluorine or hydrogen. R3 is preferably a branched alkyl radical with secondary or tertiary carbon with 4 up to 9 carbon atoms.
Man kann die N-Benzoyl-N'-phenylharnstoffe der Formel I erhalten durch Umsetzung von Benzoylisocyanaten der Formel in der X und Y die obengenannten Bedeutungen haben, mit Alkoxynnilinen der Formel in der R1, R2 und R3 die obengenannten Bedeutungen haben, vorzugsweise in Gegenwart eines inerten organischen Lösungsmittels bei einer ausreichenden Temperatur von im allgemeinen nicht mehr als 80°C.The N-benzoyl-N'-phenylureas of the formula I can be obtained by reacting benzoyl isocyanates of the formula in which X and Y have the abovementioned meanings, with alkoxynnilines of the formula in which R1, R2 and R3 have the abovementioned meanings, preferably in the presence of an inert organic solvent at a sufficient temperature of generally not more than 80.degree.
Für das Verfahren zur Herstellung der erfindungsgemäßen Verbindungen eignn sich eine Reihe von Lösungs- bzw. Verdünnungsmitteln. Als solche kommen z.B. in Betracht: Aliphatische und aromatische, gegebenenfalls chlorierte oder nitrierte Kohlenwasserstoffe, wie Benzol, Toluol, Xylole, Chlorbenzole, Benzin, Tetrachlorkohlenstoff, 1,2-Dichlorethan, Methylenchlorid, Chloroform, Nitromethan; cyclische und acyclische Ether, wie Diethylether, Dibutylether, Tetrahydrofuran, Dioxan; acyclische und cyclische Ketone, wie Aceton, Methylethylketon, Methylisopropylketon, Cyclohexanon; Nitrile, wie Acetonitril, Benzonitril. Auch Gemische dieser Lösungsmittel können verwendet werden.For the process for the preparation of the compounds according to the invention A number of solvents or diluents are suitable. As such, e.g. into consideration: Aliphatic and aromatic, optionally chlorinated or nitrated Hydrocarbons such as benzene, toluene, xylenes, chlorobenzenes, gasoline, carbon tetrachloride, 1,2-dichloroethane, methylene chloride, chloroform, nitromethane; cyclic and acyclic Ethers such as diethyl ether, dibutyl ether, tetrahydrofuran, dioxane; acyclic and cyclic Ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone, cyclohexanone; Nitriles, such as acetonitrile, benzonitrile. Mixtures of these solvents can also be used will.
Zweckmäßig verwendet man ein Lösungsmittel(gemisch), in dem die Reaktionsprodukte unlöslich sind; dies erleichtert deren Gewinnung.It is advisable to use a solvent (mixture) in which the reaction products are insoluble; this makes it easier to obtain them.
Die Umsetzung verläuft exotherm und nimmt im Bereich zwischen 20 und 60"C im allgemeinen eine ausreichende Geschwindigkeit an. Die Anwendung von überatmosphärischem Druck ist i.a. nicht erforderlich. Die Umsetzung kann diskontinuierlich oder kontinuierlich durchgeführt werden und verläuft praktisch quantitativ, wenn man die Reaktionsteilnehmer in etwa stöchiometrischem Verhältnis einsetzt. Ein Überschuß der einen oder anderen Komponente bringt keine wesentlichen Vorteile.The reaction is exothermic and increases in the range between 20 and 60 "C is generally a sufficient speed. The use of superatmospheric Pressure is generally not mandatory. The reaction can be discontinuous or continuous can be carried out and runs practically quantitatively if you consider the reactants begins in an approximately stoichiometric ratio. An excess of one or the other Component does not have any significant advantages.
Die Harnstoffe der Formel I fallen gewöhnlich in reiner fester Form an - ggf. wird das Reaktionsgemisch teilweise eingeengt - und können falls nötig, durch Umkristallisieren gereinigt werden.-Zu ihrer Charzkterisierung dienen Elementaranalyse und Schmelzpunkt.The ureas of the formula I usually fall in pure solid form on - if necessary, the reaction mixture is partially concentrated - and if necessary, be purified by recrystallization.-Elemental analysis is used to characterize them and melting point.
Zur Durchführung des erfindungsgemäßen Verfahrens wird zweckmäßigerweise das substituierte Alkoxyanilin zusammen mit dem Lösungs- oder Verdünnungsmittel vorgelegt, dann wird das Isocyanat zugegeben. Nach der Umsetzung, in der Regel nicht mehr als etwa 2 Stunden, wird das Produkt dann abgesaugt und unter vermindertem Druck getrocknet.To carry out the method according to the invention, it is expedient the substituted alkoxyaniline together with the solvent or diluent submitted, then the isocyanate is added. After implementation, usually not more than about 2 hours, the product is then suctioned off and under reduced Print dried.
Die Benzoylisocyanate der Formel II und die Alkoxyaniline der Formel III und ihre Herstellung sind bekannt (J. Org. Chem. 28, 1805-1811 (1963); Weygand-Hilgetag Organisch-Chemische Experimentierkunet, 4. Auflage, 1970, S. 373, 576, J. A. Barth Verlag Leipzig) oder sie können nach bekannten Verfahren hergestellt werden.The benzoyl isocyanates of the formula II and the alkoxyanilines of the formula III and their preparation are known (J. Org. Chem. 28, 1805-1811 (1963); Weygand-Hilgetag Organisch-Chemische Experimentierkunet, 4th edition, 1970, pp. 373, 576, J. A. Barth Verlag Leipzig) or they can be produced by known processes.
Harnstoffe der Formel 1 können auch durch Umsetzung von Amiden der Formel mit Isocyanaten der Formel hergestellt werden. In den Formeln IV und V haben X, Y, R1, R2 und R3 die obengenannten Bedeutungen.Urea of the formula 1 can also be obtained by reacting amides of the formula with isocyanates of the formula getting produced. In the formulas IV and V, X, Y, R1, R2 and R3 have the meanings given above.
Auch bei diesem Herstellverfahren werden die Reaktionspartner gewöhnlich in stöchiometrischen Mengen und vorzugsweise in Gegenwart eines Lösungsmittels umgesetzt. Eine ausreichende Reaktionstemperatur liegt i.a. unterhalb von 140"C, vorzugsweise zwischen 60 und 100"C. Gegebenenfalls kann ein Katalysator, wie Triethylamin oder eine Organozinnverbindung zugesetzt werden. Als Lösungsmittel kommen die gleichen Solventien in Betracht, die bei der Umsetzung der Verbindungen der Formel II mit den Verbindungen der Formel III verwendet werden können.In this manufacturing process, too, the reactants become common reacted in stoichiometric amounts and preferably in the presence of a solvent. A sufficient reaction temperature is generally below 140 "C, preferably between 60 and 100 "C. Optionally, a catalyst such as triethylamine or an organotin compound can be added. The same solvents are used Solvents into consideration, which in the implementation of the compounds of formula II with the compounds of formula III can be used.
Herstellungsbeispiel 1 3,8 g (4-Amino,2-fluorphenyl),(2,6-dimethylheptyl-4)-ether werden in 70 ml Toluol gelöst und mit 2,9 g 2-Chlorbenzoylisocyanat versetzt. Es wird über Nacht gerührt, eingeengt, abgesaugt und getrocknet.Preparation Example 1 3.8 g of (4-amino, 2-fluorophenyl), (2,6-dimethylheptyl-4) ether are dissolved in 70 ml of toluene and treated with 2.9 g of 2-chlorobenzoyl isocyanate. It is stirred overnight, concentrated, filtered off with suction and dried.
3,8 g Harnstoff vom Fp.: 152 - 156°C (Tabelle Nr. 15) Herstellungsbeispiel 2 4,8 g (4-Amino,2-chlorphenyl),(2,4-dimethylpentyl-3)-ether werden in 40 ml Toluol vorgelegt und mit 4,7 g 2,6-Dichlorbenzoylisocyanat tropfenweise versetzt. Es wird über Nacht gerührt, abgesaugt und getrocknet.3.8 g of urea with a melting point of 152-156 ° C. (Table No. 15) Preparation example 2 4.8 g of (4-amino, 2-chlorophenyl), (2,4-dimethylpentyl-3) ether are dissolved in 40 ml of toluene submitted and treated with 4.7 g of 2,6-dichlorobenzoyl isocyanate dropwise. It will Stirred overnight, filtered off with suction and dried.
6,3 g Harnstoff vom Fp.: 220 - 225'C (Tabelle Nr. 11).6.3 g of urea with a melting point of 220-225 ° C (Table No. 11).
Durch entsprechende Anwandlung des vorstehenden Beispiels können die nachfolgend aufgeführten Verbindungen erhalten werden; soweit sie hergestellt wurden, sind charakterisierende physikalische Stoffkonstanten (Schmelzpunkte) angegeben. Die nicht mit Stoffkonstanten versehenen Stoffe können auf die angegebene Weise erhalten werden und lassen aufgrund ihrer Strukturähnlichkeit eine den untersuchten Verbindungen vergleichbare biologische Wirksamkeit erwarten.By adapting the above example accordingly, the compounds listed below are obtained; as far as they were manufactured, characterizing physical material constants (melting points) are given. The substances that are not provided with constants can be used in the specified manner can be obtained and, due to their structural similarity, leave one of the investigated Expect compounds to have comparable biological efficacy.
Nr. X Y R1 R2 R3 Fp.No. X Y R1 R2 R3 Fp.
1 F F F H Isopropyl 187 - 194 2 C1 C1 F H Isopropyl 199 - 204 3 H H F H Isopropyl 173 - 178 4 F F C1 H sec.-Butyl 172 - 174 5 C1 C1 Cl H sec.-Butyl 154 - 158 6 H C1 CI H sec.-Butyl 171 - 174 7 F F F H 2,4-Dimethylpentyl-(3) 187 - 189 8 C1 Cl F H 2,4-Dimethylpentyl-(3) 211 - 216 9 H C1 F H 2,4-Dimethylpentyl-(3) 205 - 210 10 F F Cl H 2,4-Dimethylpentyl-(3) 166 - 173 11 Cl Cl Cl H 2,4-Dimethylpentyl-(3) 220 - 225 12 H C1 C1 H 2,4-Dimethylpentyl-(3) 193 - 205 13 F F F H 2,6-Dimethylheptyl-(4) 117 - 124 14 Cl Cl F H 2,6-Dimethylheptyl-(4) 211 - 216 15 H Cl F H 2,6-Dimethylheptyl-(4) 152 - 156 16 H CH3 F H 2,6-Dimethylheptyl-(4) 17 H Br F H 2,6-Dimethylheptyl-(4) 18 F F H H 2,6-Dimethylheptyl-(4) Nr. X Y R1 R2 R3 Fp. 1 F F F H isopropyl 187-194 2 C1 C1 F H isopropyl 199-204 3 H H F H isopropyl 173-178 4 F F C1 H sec-butyl 172-174 5 C1 C1 Cl H sec-butyl 154-158 6 H C1 CI H sec-butyl 171-174 7 F F F H 2,4-dimethylpentyl- (3) 187 - 189 8 C1 Cl F H 2,4-dimethylpentyl- (3) 211 - 216 9 H C1 F H 2,4-dimethylpentyl- (3) 205 - 210 10 F F Cl H 2,4-dimethylpentyl- (3) 166 - 173 11 Cl Cl Cl H 2,4-dimethylpentyl- (3) 220 - 225 12 H C1 C1 H 2,4-dimethylpentyl- (3) 193-205 13 F F F H 2,6-dimethylheptyl- (4) 117 - 124 14 Cl Cl F H 2,6-dimethylheptyl- (4) 211-216 15 H Cl F H 2,6-dimethylheptyl- (4) 152-156 16 H CH3 F H 2,6-dimethylheptyl- (4) 17 H Br F H 2,6-dimethylheptyl- (4) 18 F F H H 2,6-dimethylheptyl- (4) No. X Y R1 R2 R3 Fp.
19 C1 Cl H H 2,6-Dimethylheptyl-(4) 20 H Cl H H 2,6-Dimethylheptyl-(4) 21 F F Cl H Cyclohexyl 22 Cl Cl Cl H Cyclohexyl 23 H Cl Cl Cyclohexyl 24 F F Br H 2,4-Dimethylpentyl-(3) 25 Cl Cl Br H 2,4-Dimethylpentyl-(3) 26 H Cl Br H 2,4-Dimethylpentyl-(3) 27 F F Cl Cl 2,6-Dimethylheptyl-(4) 28 Cl Cl Cl Cl 2,6-Dimethylheptyl-(4) 29 H Cl Cl Cl 2,6-Dimethylheptyl-(4) 30 F F H Cl 2,6-Dimethylheptyl-(4) 31 Cl Cl H Cl 2,6-Dimethylheptyl-(4) 32 H Cl H Cl 2,6-Dimethylheptyl-(4) 33 F F Cl H tert.-Butyl 34 Cl Cl Cl H tert.-Butyl 35 H Cl Cl H tert.-Butyl 36 F F F H 3-Ethylpentyl 37 Cl Cl F H 3-Ethylpentyl 38 H Cl F H 3-Ethylpentyl 39 F F F H 5,5,3-Trimethylhexyl 40 Cl Cl F H 5,5,3-Trimethylhexyl 41 H Cl F H 5,5,3-Trimethylhexyl19 C1 Cl H H 2,6-dimethylheptyl- (4) 20 H Cl H H 2,6-dimethylheptyl- (4) 21 F F Cl H Cyclohexyl 22 Cl Cl Cl H Cyclohexyl 23 H Cl Cl Cyclohexyl 24 F F Br H 2,4-dimethylpentyl- (3) 25 Cl Cl Br H 2,4-dimethylpentyl- (3) 26 H Cl Br H 2,4-dimethylpentyl- (3) 27 F F Cl Cl 2,6-dimethylheptyl- (4) 28 Cl Cl Cl Cl 2,6-dimethylheptyl- (4) 29 H Cl Cl Cl 2,6-dimethylheptyl- (4) 30 F F H Cl 2,6-dimethylheptyl- (4) 31 Cl Cl H Cl 2,6-dimethylheptyl- (4) 32 H Cl H Cl 2,6-dimethylheptyl- (4) 33 F F Cl H tert -butyl 34 Cl Cl Cl H tert -butyl 35 H Cl Cl H tert-butyl 36 F F F H 3-ethylpentyl 37 Cl Cl F H 3-ethylpentyl 38 H Cl F H 3-ethylpentyl 39 F F F H 5,5,3-trimethylhexyl 40 Cl Cl F H 5,5,3-trimethylhexyl 41 H Cl F H 5,5,3-trimethylhexyl
Claims (7)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833334224 DE3334224A1 (en) | 1983-09-22 | 1983-09-22 | N-Benzoyl-N'-alkoxyphenylureas and their use for controlling insects and acarids |
| EP84111168A EP0142667B1 (en) | 1983-09-22 | 1984-09-19 | N-benzoyl-n'-alkoxyphenyl ureas and their use in combating insects and acaridae |
| DE8484111168T DE3476538D1 (en) | 1983-09-22 | 1984-09-19 | N-benzoyl-n'-alkoxyphenyl ureas and their use in combating insects and acaridae |
| CA000463661A CA1280767C (en) | 1983-09-22 | 1984-09-20 | N-benzoyl-n'-alkoxyphenylureas and their use for controlling insectsand acaridae |
| JP19699784A JPS6087255A (en) | 1983-09-22 | 1984-09-21 | N-benzoyl-n'-alkoxyphenylurea, manufacture and insecticidal tickicide containing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833334224 DE3334224A1 (en) | 1983-09-22 | 1983-09-22 | N-Benzoyl-N'-alkoxyphenylureas and their use for controlling insects and acarids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3334224A1 true DE3334224A1 (en) | 1985-04-04 |
Family
ID=6209742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833334224 Withdrawn DE3334224A1 (en) | 1983-09-22 | 1983-09-22 | N-Benzoyl-N'-alkoxyphenylureas and their use for controlling insects and acarids |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6087255A (en) |
| DE (1) | DE3334224A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0167197A1 (en) * | 1984-07-05 | 1986-01-08 | Duphar International Research B.V | Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same |
| US4783485A (en) * | 1983-01-24 | 1988-11-08 | Duphar International Research B.V. | Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same |
-
1983
- 1983-09-22 DE DE19833334224 patent/DE3334224A1/en not_active Withdrawn
-
1984
- 1984-09-21 JP JP19699784A patent/JPS6087255A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4783485A (en) * | 1983-01-24 | 1988-11-08 | Duphar International Research B.V. | Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same |
| EP0167197A1 (en) * | 1984-07-05 | 1986-01-08 | Duphar International Research B.V | Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6087255A (en) | 1985-05-16 |
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