[go: up one dir, main page]

DE3123720A1 - Urea derivatives, their preparation and use - Google Patents

Urea derivatives, their preparation and use

Info

Publication number
DE3123720A1
DE3123720A1 DE19813123720 DE3123720A DE3123720A1 DE 3123720 A1 DE3123720 A1 DE 3123720A1 DE 19813123720 DE19813123720 DE 19813123720 DE 3123720 A DE3123720 A DE 3123720A DE 3123720 A1 DE3123720 A1 DE 3123720A1
Authority
DE
Germany
Prior art keywords
formula
urea
tetrachlorophenyl
urea derivatives
preparation
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Withdrawn
Application number
DE19813123720
Other languages
German (de)
Inventor
Heinz-Manfred Dipl.-Chem. Dr. 6530 Bingen Becher
Picarda Dipl.-Biol. Dr. 6500 Mainz Prokić-Immel
Walter Dipl.-Entomologe Dr. 6100 Darmstadt Wirtz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Agrar GmbH and Co KG
Original Assignee
Celamerck GmbH and Co KG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Celamerck GmbH and Co KG filed Critical Celamerck GmbH and Co KG
Priority to DE19813123720 priority Critical patent/DE3123720A1/en
Priority to DE8181109618T priority patent/DE3161657D1/en
Priority to AT81109618T priority patent/ATE5585T1/en
Priority to EP81109618A priority patent/EP0052833B1/en
Priority to US06/321,446 priority patent/US4457943A/en
Priority to IL64317A priority patent/IL64317A/en
Priority to AU77725/81A priority patent/AU537096B2/en
Priority to PL1981233920A priority patent/PL129912B1/en
Priority to SI8112738A priority patent/SI8112738A8/en
Priority to ES507310A priority patent/ES8301903A1/en
Priority to CA000390554A priority patent/CA1177852A/en
Priority to ES507324A priority patent/ES8301904A1/en
Priority to YU2738/81A priority patent/YU41998B/en
Priority to DD81235011A priority patent/DD202007A5/en
Priority to NZ199011A priority patent/NZ199011A/en
Priority to HU813477A priority patent/HU185066B/en
Priority to MX6352A priority patent/MX154685A/en
Priority to BR8202968A priority patent/BR8202968A/en
Priority to DK230982A priority patent/DK155831C/en
Publication of DE3123720A1 publication Critical patent/DE3123720A1/en
Priority to US06/604,371 priority patent/US4622340A/en
Priority to HR921360A priority patent/HRP921360B1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
    • C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
    • C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/24—Derivatives of thiourea containing any of the groups, X being a hetero atom, Y being any atom
    • C07C335/26—Y being a hydrogen or a carbon atom, e.g. benzoylthioureas

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Novel insecticidal urea derivatives, and their preparation by processes which are known per se, are described. These urea derivatives correspond to the formula <IMAGE> in which X represents oxygen or sulphur, Y represents chlorine or fluorine, and Z represents hydrogen, chlorine or fluorine.

Description

Harnstoffderivate, ihre Herstellung und Ver-Urea derivatives, their production and

wendung Die Erfindung betrifft neue Harnstoffderivate der allgemeinen Formel in der X für Sauerstoff oder Schwefel Y für Chlor oder Fluor und Z für Wasserstoff, Chlor oder Fluor steht, sowie die Herstellung dieser Verbindungen nach an sich bekannten Verfahren und die Verwendung bei der Bekämpfung von tierischen Schädlingen im Pflanzenschutz.application The invention relates to new urea derivatives of the general formula in which X is oxygen or sulfur, Y is chlorine or fluorine and Z is hydrogen, chlorine or fluorine, and the preparation of these compounds by processes known per se and their use in combating animal pests in crop protection.

Aus der DE-AS 2 123 236 sind Benzoylharnstoffe mit Wirkung gegen tierische Schädlinge bekannt. Die in dieser DE-AS beschriebene Verbindung der Formel ist ein Handelsprodukt (Diflubenzuron). Gegenüber dieser Verbindung zeigen die Verbindungen gemäß der Erfindung eine deutlich überlegene Wirkung, z.B. gegen Insekten im Raupen- oder Larvenstadium.From DE-AS 2 123 236 benzoylureas with action against animal pests are known. The compound of the formula described in this DE-AS is a commercial product (Diflubenzuron). Compared to this compound, the compounds according to the invention show a clearly superior action, for example against insects in the caterpillar or larval stage.

Die Herstellung der neuen Verbindungen kann nach an sich bekannten Verfahren erfolgen: a) in dem man das Anilin der Formel mit einem Isocyanat bzw. Senföl der Formel oder b) ein Isocyanat bzw. Senföl der Formel mit einem Benzamid der Formel umsetzt.The new compounds can be prepared by processes known per se: a) by using the aniline of the formula with an isocyanate or mustard oil of the formula or b) an isocyanate or mustard oil of the formula with a benzamide of the formula implements.

Die Umsetzungen gemäß a) und b) werden bei Temperaturen zwischen der Umgebungstemperatur und der Siedetemperatur des Reaktions gemisches durchgeführt. Als Reaktionsmedium dient ein inertes Lösungsmittel, z.B. ein aromatischer Kohlenwasserstoff, etwa Toluol oder Xylol, Chlorbenzol, Pyridin, ein Äther wie Dioxan, Tetrahydrofuran, ggf. in Gegenwart einer tertiären organischen Base (Triäthylamin, Pyridin).The reactions according to a) and b) are carried out at temperatures between Ambient temperature and the boiling temperature of the reaction mixture carried out. An inert one is used as the reaction medium Solvent such as an aromatic one Hydrocarbons such as toluene or xylene, chlorobenzene, pyridine, an ether such as dioxane, Tetrahydrofuran, if necessary in the presence of a tertiary organic base (triethylamine, Pyridine).

Die Ausgangsstoffe können, soweit sie noch nicht beschrieben wurden, nach üblichen Methoden in an sich bekannter Weise gewonnen werden.The starting materials can, as far as they have not yet been described, can be obtained by conventional methods in a manner known per se.

Das Anilin der Formel II erhält man aus der entsprechenden Nitroverbindung durch Reduktion der Nitrogruppe mit den hierfür gebräuchlichen Reduktionsmitteln. Aus dem Anilin II entsteht durch Umsetzung mit Phosgen bzw. Thiophosgen das Isocyanat bzw.The aniline of the formula II is obtained from the corresponding nitro compound by reducing the nitro group with the reducing agents commonly used for this purpose. The isocyanate is formed from the aniline II through reaction with phosgene or thiophosgene respectively.

Senföl der Formel IV.Formula IV mustard oil.

Die neuen Verbindungen können vor allem als hochwirksame Insektizide verwendet werden. Sie eignen sich besonders zur Bekämpfung von Stechmücken, Raupen, Käfern und Käferlarven.The new compounds can mainly be used as highly effective insecticides be used. They are particularly suitable for combating mosquitoes, caterpillars, Beetles and beetle larvae.

Fur die Anwendung werden die erfindungsgemäßen Wirkstoffe mit Ublichen Hilfs- und/oder Trägerstoffen zu gebräuchlichen Formulierungen verarbeitet, z.B. Emulsionskonzentraten, Suspensionspulvern, Stäuben. Die Anwendung erfolgt in Spritzbrühen und Stäuben mit Wirkstoffkonzentrationen zwischen etwa 0,0005 und 2 %, in Form von ULV-Formulierungen auch mit höheren Wirkstoffkonzentrationen (bis etwa 90 %). Die Aufwandmenge pro Hektar beträgt je nach Wirkstoff und Kultur zwischen etwa 0,005 und 0,5 kg, vorzugsweise zwischen 0,01 und 0,25 kg.For use, the active compounds according to the invention are commonly used Auxiliaries and / or carriers processed into customary formulations, e.g. Emulsion concentrates, suspension powders, dusts. It is used in spray liquors and dusts with active ingredient concentrations between about 0.0005 and 2%, in the form of ULV formulations also with higher active ingredient concentrations (up to about 90%). the The application rate per hectare is between about 0.005, depending on the active ingredient and crop and 0.5 kg, preferably between 0.01 and 0.25 kg.

Formulierungsbeispiel: Susoensionspulver (Angaben in Gew.-0jo') 25 % Wirkstoff gemäß der Erfindung 55 % Kaolin 10 % kolloidale Kieselsäure 9 % Ligninsulfonat (Dispergiermittel) 1 % Natriumtetrapropylenbenzolsulfonat (Netzmittel) Die Bestandteile werden wie üblich zu einem Suspensionspulver (Partikelgröße C 4)verarbeitet. Für die Anwendung wird mit Wasser eine Spritzbrühe hergestellt, die etwa 0,0005 bis 0,5 Gew.-% Wirkstoff enthält.Formulation example: suspension powder (data in percentages by weight) 25 % Active ingredient according to the invention 55% kaolin 10% colloidal silica 9% lignin sulfonate (Dispersant) 1% sodium tetrapropylene benzene sulfonate (wetting agent) The ingredients are processed into a suspension powder (particle size C 4) as usual. For the application is made with water a spray mixture that is about 0.0005 to Contains 0.5% by weight of active ingredient.

Die überlegene Wirksamkeit der erfindungsgemäßen Verbindungen zeigt sich z.B. beim Vergleich mit dem oben erwähnten Handelsprodukt Diflubenzuron.Shows the superior effectiveness of the compounds according to the invention e.g. when comparing with the above-mentioned commercial product Diflubenzuron.

Der Vergleich wurde an Larven (Aedes aegyptii, A) und an Raupen (Spodoptera littoralis, B) im Labor durchgeführt. Ermittelt wurde die LD95 in ppm Wirkstoff, wobei die Spritzbrühe aus einer 0,1 bis 0,5-prozentigen Lösung der Wirkstoffe in Aceton durch Verdünnen mit Wasser hergestellt wurde.The comparison was made on larvae (Aedes aegyptii, A) and on caterpillars (Spodoptera littoralis, B) performed in the laboratory. The LD95 was determined in ppm active ingredient, wherein the spray mixture from a 0.1 to 0.5 percent solution of the active ingredients in Acetone was made by diluting it with water.

I: N-(2,3,4,5-Tetrachlorphenyl)-N'-(2,6-difluorbenzoyl)-harnstoff II: N-(2,3,4,5-Tetrachlorphenyl)-N'-(2-chlorbenzoyl)-thioharnstoff III: N-(2,3,4,5-Tetrachlorphenyl)-N'-(2-chlor-6-fluorbenzoyl)-harnstoff.I: N- (2,3,4,5-tetrachlorophenyl) -N '- (2,6-difluorobenzoyl) urea II: N- (2,3,4,5-tetrachlorophenyl) -N '- (2-chlorobenzoyl) -thiourea III: N- (2,3,4,5-tetrachlorophenyl) -N' - (2-chloro- 6-fluorobenzoyl) urea.

Wirkstoff LD95 gegen A LD95 gegen B (ppm Wirkstoff) (ppm Wirkstoff) Diflubenzuron 0,0031 3,4 I 0,00084 0,3 II - 0,4 III 0,00094 0,65 Die Herstellung der neuen Verbindungen ist in dem folgenden Beispiel näher erläutert: Beispiel N-(2,3,4,5-Tetrachlor-phenyl)-N'-(2,6-difluorbenzoyl)-harnstoff Zu der Lösung von 4 g (0,017 Mol) vic. Tetrachloranilin in 60 ml Toluol werden 3,9 g (0,020 Mol) 2,6-Difluorbenzoylisocyanat gegeben. Die entstandene Lösung wird 1 h lang bei Raumtemperatur gerührt. Active ingredient LD95 against A LD95 against B (ppm active ingredient) (ppm active ingredient) Diflubenzuron 0.0031 3.4 I 0.00084 0.3 II - 0.4 III 0.00094 0.65 The manufacture of the new compounds is explained in more detail in the following example: Example N- (2,3,4,5-tetrachlorophenyl) -N '- (2,6-difluorobenzoyl) urea To the solution of 4 g (0.017 mol) vic. Tetrachloroaniline in 60 ml of toluene will be 3.9 added g (0.020 mol) of 2,6-difluorobenzoyl isocyanate. The resulting solution is 1 stirred for h at room temperature.

Danach wird das in dieser Zeit ausgefallene Produkt abgesaugt, mit Toluol gewaschen und getrocknet.The product which has precipitated out during this time is then filtered off with suction Toluene washed and dried.

Ausbeute: 7 g (0,017 Mol); prak-t. quantitativ) Fp.: 255 - 2570C.Yield: 7 g (0.017 mol); prak-t. quantitative) m.p .: 255-2570C.

Ein kleiner Teil wurde aus viel A6eton umkristallisiert.A small part was recrystallized from a large amount of A6eton.

Fp. : 257 - 259°C.M.p .: 257-259 ° C.

Entsprechend werden folgende Verbindungen erhalten: a) N-( 2,3,4, 5-Tetrachlorphenyl)-N1-( 2-chlor-6-fluorbenzoyl)-harnstoff, Fp.> 2500C; b) N-(2,3,4,5-Tetrachlorphenyl)-N'-(2-chlorbenzoyl)-thioharnstoff; Fp. 186-187°C; c) N-(2,3,4,5-TetrachlorphenZl)-N'-(2-chlorbenzoyl)-harnstoff; d) N-(2,3,4,5-Tetrachlorphenyl)-N'-(2,6-difluor benzoyl)-thioharnstoff; e) N-(2,3,4,5-Tetrachlorphenyl)-N'-(2-chlor-6-fluorbenzoyl)-thionharnstoff; f) N-(2,3,4,5-Tetrachlorphenyl)-N'-(2-fluorbenzoyl)-harnstoff; g) N-(2,3,4,5-Tetrachlorphenyl)-N'-(2-fluorbenzoyl)-thioharnstoff; h) N-(2,3,4,5-Tetrachlorphenyl)-N'-(2,6-dichlorbenzoyl)-harnstoff; i) N-(2,3,4,5-Tetrachlorphenyl)-N'-(2,6-dichlorbenzoyl)-thionharnstoff.The following compounds are obtained accordingly: a) N- (2,3,4, 5-tetrachlorophenyl) -N1- (2-chloro-6-fluorobenzoyl) urea, m.p.> 2500C; b) N- (2,3,4,5-tetrachlorophenyl) -N '- (2-chlorobenzoyl) thiourea; Mp 186-187 ° C; c) N- (2,3,4,5-tetrachlorophenZl) -N '- (2-chlorobenzoyl) urea; d) N- (2,3,4,5-tetrachlorophenyl) -N '- (2,6-difluoro-benzoyl) -thiourea; e) N- (2,3,4,5-tetrachlorophenyl) -N '- (2-chloro-6-fluorobenzoyl) -thione urea; f) N- (2,3,4,5-tetrachlorophenyl) -N '- (2-fluorobenzoyl) urea; g) N- (2,3,4,5-tetrachlorophenyl) -N '- (2-fluorobenzoyl) thiourea; h) N- (2,3,4,5-tetrachlorophenyl) -N '- (2,6-dichlorobenzoyl) urea; i) N- (2,3,4,5-tetrachlorophenyl) -N '- (2,6-dichlorobenzoyl) -thione urea.

Claims (7)

Patentansprüche 4¼ 1. Harnstoffderivate der Formel in der X iUi Sauerstoff oder schwefel Y für Chlor oder Fluor und Z für Wasserstoff, Chlor oder Fluor steht.Claims 4¼ 1. Urea derivatives of the formula in which X iUi oxygen or sulfur, Y is chlorine or fluorine and Z is hydrogen, chlorine or fluorine. 2. Schädlingsbekämpfungsmittel, gekennzeichnet durch einen Gehalt an mindestens einer Verbindung nach Anspruch 1.2. Pesticides, characterized by a content of at least one compound according to Claim 1. 3. Verwendung von Verbindungen nach Anspruch 1 bei der Bekämpfung von Insekten, insbesondere von Schädlingen im Raupen- oder Larvenstadium.3. Use of compounds according to Claim 1 in combating of insects, especially pests in the caterpillar or larval stage. 4. Verfahren zur Herstellung von Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß man a) das Anilin der Formel mit einem Isocyanat oder Senföl der Formel oder b) ein Isocyanat oder Senföl der Formel mit einem Benzamid der Formel umsetzt.4. Process for the preparation of compounds according to Claim 1, characterized in that a) the aniline of the formula with an isocyanate or mustard oil of the formula or b) an isocyanate or mustard oil of the formula with a benzamide of the formula implements. 5. N-(2,3,4,5-Tetrachlorphenyl)-N'-(2,6-difluorbenzoyl)-harnstoff.5. N- (2,3,4,5-tetrachlorophenyl) -N '- (2,6-difluorobenzoyl) urea. 6. Schädlingsbekämpfungsmittel, insbesondere zur Bekämpfung von Larven und Raupen, gekennzeichnet durch einen Gehalt an mindestens einer Verbindung nach Anspruch 5.6. Pesticides, especially for controlling larvae and caterpillars, characterized by a content of at least one compound according to Claim 5. 7. Verwendung einer Verbindung nach Anspruch 5 bei der Bekämpfung tierischer Schädlinge, insbesondere Larven und Raupen.7. Use of a compound according to claim 5 in combating animal pests, in particular larvae and caterpillars.
DE19813123720 1980-11-22 1981-06-15 Urea derivatives, their preparation and use Withdrawn DE3123720A1 (en)

Priority Applications (21)

Application Number Priority Date Filing Date Title
DE19813123720 DE3123720A1 (en) 1981-06-15 1981-06-15 Urea derivatives, their preparation and use
DE8181109618T DE3161657D1 (en) 1980-11-22 1981-11-11 Urea derivatives, preparation and use
AT81109618T ATE5585T1 (en) 1980-11-22 1981-11-11 UREA DERIVATIVES, THEIR PRODUCTION AND USE.
EP81109618A EP0052833B1 (en) 1980-11-22 1981-11-11 Urea derivatives, preparation and use
US06/321,446 US4457943A (en) 1980-11-22 1981-11-16 N-(2H-Difluoro-3,5-dichloro-phenyl)-N'-(2,6-difluorobenzoyl) urea derivative and pesticidal compositions containing same
IL64317A IL64317A (en) 1980-11-22 1981-11-19 Substituted n-phenyl-n-benzoyl ureas,their preparation and their use as pesticides
ES507324A ES8301904A1 (en) 1980-11-22 1981-11-20 Urea derivatives, preparation and use.
HU813477A HU185066B (en) 1980-11-22 1981-11-20 Pesticide compositions containing urea derivatives and process for producing new urea derivatives
SI8112738A SI8112738A8 (en) 1980-11-22 1981-11-20 Process for preparing new urea derivatives
ES507310A ES8301903A1 (en) 1980-11-22 1981-11-20 Urea derivatives, preparation and use.
CA000390554A CA1177852A (en) 1980-11-22 1981-11-20 Urea derivatives, their preparation and use
AU77725/81A AU537096B2 (en) 1980-11-22 1981-11-20 N-phenyl-n-benzoyl ureas and thioureas
YU2738/81A YU41998B (en) 1980-11-22 1981-11-20 Process for preparing new urea derivatives
DD81235011A DD202007A5 (en) 1980-11-22 1981-11-20 PROCESS FOR THE PREPARATION OF UREA DERIVATIVES
NZ199011A NZ199011A (en) 1980-11-22 1981-11-20 N-(2,3,4,5-tetrahalophenyl)-n'-(2,6-dihalobenzoyl ureas and thioureas
PL1981233920A PL129912B1 (en) 1980-11-22 1981-11-20 Method of obtaining new urea derivatives and pesticide containing them
MX6352A MX154685A (en) 1980-11-22 1982-04-30 PROCEDURE FOR THE PREPARATION OF UREA DERIVATIVES
BR8202968A BR8202968A (en) 1980-11-22 1982-05-21 UREA DERIVATIVES, PESTICIDE COMPOSITES, COMPOUND USE AND PROCESS FOR COMPOUND PREPARATION
DK230982A DK155831C (en) 1981-06-15 1982-05-21 N-PHENYL-N'-BENZOYL URINARY DERIVATIVES AND THEIR USE AS PESTICIDES
US06/604,371 US4622340A (en) 1980-11-22 1984-04-26 Urea derivatives and pesticidal compositions containing same
HR921360A HRP921360B1 (en) 1980-11-22 1992-11-26 Urea derivatives, the preparation and use thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19813123720 DE3123720A1 (en) 1981-06-15 1981-06-15 Urea derivatives, their preparation and use

Publications (1)

Publication Number Publication Date
DE3123720A1 true DE3123720A1 (en) 1982-12-30

Family

ID=6134763

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19813123720 Withdrawn DE3123720A1 (en) 1980-11-22 1981-06-15 Urea derivatives, their preparation and use

Country Status (2)

Country Link
DE (1) DE3123720A1 (en)
DK (1) DK155831C (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3433152A1 (en) * 1984-09-10 1985-04-11 Celamerck Gmbh & Co Kg, 6507 Ingelheim Insecticidally active combinations of benzoylurea derivatives with 1,2-methylenedioxybenzene derivatives and, if desired, pyrethrins or pyrethroids
EP0176868A1 (en) * 1984-09-29 1986-04-09 Shell Internationale Researchmaatschappij B.V. Benzoyl ureas having an insecticidal activity
EP0255678A1 (en) * 1986-08-05 1988-02-10 Shell Internationale Researchmaatschappij B.V. Process for production of benzoyl ureas

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3433152A1 (en) * 1984-09-10 1985-04-11 Celamerck Gmbh & Co Kg, 6507 Ingelheim Insecticidally active combinations of benzoylurea derivatives with 1,2-methylenedioxybenzene derivatives and, if desired, pyrethrins or pyrethroids
EP0176868A1 (en) * 1984-09-29 1986-04-09 Shell Internationale Researchmaatschappij B.V. Benzoyl ureas having an insecticidal activity
EP0255678A1 (en) * 1986-08-05 1988-02-10 Shell Internationale Researchmaatschappij B.V. Process for production of benzoyl ureas

Also Published As

Publication number Publication date
DK155831C (en) 1989-10-02
DK155831B (en) 1989-05-22
DK230982A (en) 1983-11-22

Similar Documents

Publication Publication Date Title
EP0052833B1 (en) Urea derivatives, preparation and use
DE2438747C2 (en) Benzoylureido diphenyl ethers, process for their preparation and their use as insecticides
DE2531279C2 (en) N- (3-Trifluoromethyl-4-halophenyl) - N&#39;-benzoylureas, process for their preparation and their use as insecticides
DE2123236B2 (en) Urea and thiourea derivatives, processes for their preparation and their use
DE2530439A1 (en) NOVEL BIS-(0-1-ALKYLTHIO-AETHYLIMINO)-N-METHYLCARBAMIC ACID)-N,N&#39;-SULFIDES, PROCESS FOR THEIR PREPARATION AND PESTICIDES
CH618965A5 (en)
DE3033512C2 (en)
EP0235089B1 (en) N-benzoyl-n&#39;-phenyl ureas, their preparation and their use against pests
CH645348A5 (en) ACYL UREAS AND INSECTICIDES CONTAINING THESE COMPOUNDS.
EP0040179B1 (en) Phenylbenzoyl urea
DE3783070T2 (en) PHENYL URINE.
DE3123720A1 (en) Urea derivatives, their preparation and use
CH647754A5 (en) ACYL UREAS, INSECTICIDAL AGENTS CONTAINING THESE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF.
EP0044278B1 (en) Phenyl ureas
DE3044055A1 (en) N-Halo:benzoyl-N&#39;-tetra:halo-phenyl (thio)urea derivs. - prepd. e.g. by reaction of a tetra:halo-aniline with a halo-benzoyl isocyanate or isothiocyanate
DE3041947A1 (en) PHENOXYPHENYL URINE
DE1142599B (en) Process for the production of carbamic acid esters
DE3240975A1 (en) Phenylbenzoylureas and -thioureas
EP0142667B1 (en) N-benzoyl-n&#39;-alkoxyphenyl ureas and their use in combating insects and acaridae
DD235996A5 (en) PESTICIDE BENZOYL HARNASTIC COMPOUND
DE2843691A1 (en) DIURETHANE, METHOD FOR PRODUCING THESE COMPOUNDS AND THE SELECTIVE HERBICIDES CONTAINING THEM
DE3529343A1 (en) Acyl ureas, their preparation, and their use as insecticides containing these compounds
DE3435895A1 (en) Novel benzoylureas
DE4000335A1 (en) New optically active insecticide - is (plus)-n-2,6-di:fluoro:benzoyl -N&#39;-4-(1,1,2,3,3,3-hexafluoropropoxy) -2,5-di:chloro:phenyl-urea
DE1568490A1 (en) Process for the preparation of fluoroacylaminotrichloromethyl methane derivatives

Legal Events

Date Code Title Description
8139 Disposal/non-payment of the annual fee