GB2083360A - Solvent-flowable compositions containing a substituted urea insecticide - Google Patents
Solvent-flowable compositions containing a substituted urea insecticide Download PDFInfo
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- GB2083360A GB2083360A GB8126638A GB8126638A GB2083360A GB 2083360 A GB2083360 A GB 2083360A GB 8126638 A GB8126638 A GB 8126638A GB 8126638 A GB8126638 A GB 8126638A GB 2083360 A GB2083360 A GB 2083360A
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- 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<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Dispersion Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
A non-aqueous solvent-flowable insecticide composition which comprises a solvent having suspended therein a substituted urea insecticide wherein the nitrogen atoms of the urea moiety are independently substituted with substituted or unsubstituted phenyl, benzoyl, pyridyl, pyrazinyl or benzopyrazinyl radicals and containing a suspending agent for the insecticide and an emulsifier which is an alkaline earth metal, magnesium or aluminium salt of a branched chain C6-C18 alkylarylsulphonic acid. Chlorpyrifos, chlorpyrifosmethyl, diazinon, azodrin, parathion, methyl parathion, malathion, fenvalerate, cypermethrin, decamethrin, acephate and chlordane may be used in the compositions.
Description
SPECIFICATION Solvent-flowable compositions containing a substituted urea insecticide
The present invention relates to non-aqueous solvent flowable compositions containing a substituted urea insecticide.
Benzoyl phenyl ureas and pyridylcarbonyl phenyl ureas are becoming increasingly important as insecticides which are used at low levels in combination with other insecticides against pests such as those which affect cotton crops.
The insolubility of benzoyl phenyl urea and pyridylcarbonyl phenyl ureas has hitherto necessitated their formulation, in combination with other insecticides, in the form of wettable powders or aqueous suspension concentrates.
Certain non-aqueous solvent-flowable toxicant compositions are known in which one toxicant is dissolved in the solvent and another particulate toxicant is dissolved in the solvent by the use of an appropriate suspending agent. A balanced emulsifier system is included in such compositions to emulsify the composition when it is added to water.
Specific organophilic clays, such as bentonites modified by treatment with long chain amines, i.e. the products known as Bentones (Registered Trade Mark), have been used as suspending agents for the particulate toxicants in such formulations.
The balanced emulsifier systems in such formulations are generally an anionic-nonionic blend, usually composed of a calcium dodecylbenzenesulphonate as the anionic and any suitable conventional nonionic which will provide a balanced emulsifier blend for the particular formulation.
We found, whilst attempting to develop a non-aqueous solvent-flowable composition containing a benzoyl phenyl urea or pyridyl carbonyl phenyl urea, that using a calcium dodecylbenzenesulphonate which has an essentially linear dodecyl moiety and which is classed by the manufacturers as being biodegradable, a very rigid gel structure was formed by the interaction of the benzoyl phenyl urea or pyridyl carbonyl urea and the calcium dodecylbenzenesulphonate.
The gel structure made the formulation unusable.
We surprisingly discovered that when a branched chain calcium dodecylbenzenesulphonate was used instead of the linear calcium dodecylbenzenesulphonate, the gel structure was not formed and a non-aqueous solvent-flowable composition containing a benzoyl phenyl urea or pyridylcarbonyl phenyl urea insecticide was obtained.
Accordingly, the present invention provides a non-aqueous solvent-flowable insecticide composition which comprises a solvent having suspended therein a substituted urea insecticide wherein the nitrogen atoms of the urea moiety are independently substituted with substituted or unsubstituted phenyl, benzoyl, pyridyl, pyrazinyl or benzopyrazinyl radicals, for example, the known benzoyl phenyl ureas, benzoyl pyridyl ureas, pyridylcarbonyl phenyl ureas and benzoyl pyrazinyl ureas such as are described, for example, in British specifications 1,324,293; 1,501,607 and 1,575,799, German Patent Specification No. 2,926,480 and in U.S. Patents 4,148,902; 4,173,637 and Reissue 30,563 and containing a suspending agent for the insecticide and an emulsifier which is an alkaline earth metal, magnesium or aluminium salt of a branched-chain C6-C18 aryl sulphonic acid.
Whilst any benzoylphenylurea insecticide may be used in the compositions of the present invention, the preferred insecticides of this class are those compounds of the general formula:
wherein R is a hydrogen or halogen atom, or a C,-C2 alkyl or nitro group at position 2 and/or position 6; or a trimethylsilyl group;
R' is a hydrogen or halogen atom, or an alkyl C12 group;
X is O or S;
Y is a halogen atom; C14 alkyl; C14 alkoxy; halo substituted C14 alkyl;
halosubstituted C14 alkoxy; halosubstituted C24 alkenyl; nitro; COOT; COOR3 wherein R3 is a C16 alkyl group; a phenoxy group substituted at the 4-position by cyano, trifluoromethyl, nitro, C14 alkyl or alkoxy; a 2-pyridyloxy group substituted at the 5-position by cyano or trifluoromethyl; or Y is the group ZR4R5 wherein
Z is 0, S, SO, SO2 or NH;
R4 is C1 4aikylene; and R5 is a phenyl or heterocyclic group; m is 1 or 2; and n is 1 or 2.
Particularly preferred compounds of the Formula I are the following:
1 -[4-(2, 2-dichloro- 1, 1 -difluoroethoxy)phenyl]-3-(2-chlorobenzoyl)urea;
1 -(4-trifluoromethoxyphenyl)-3-(2-chlorobenzoyl)urea;
1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea.
1-[3,5-dichloro-4-(2-chloro-1,1-difluoroethoxy)phenyl]-3-(2,6-difluorobenzoyl)urea,
1-[3,5-dichloro-4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]-3-(2-chlorobenzoyl)urea, and
1 -[3,5-dichloro-4-((5-trifluoromethyl)-3-chloro-2-pyridyloxy)-phenyl]-3-(2, 6-difluorobenzoyl)urea.
Similarly, whilst any pyridylcarbonyl phenyl urea may be used in the compositions of the present invention, the preferred insecticides of this class are
(i) those compounds of the general formulae:
wherein each R' is independently a hydrogen or halogen atom or a C12 alkyl or nitro group: R" is a hydrogen or halogen atom, or a C14 alkyl or C14 alkoxy group;
X is O or S; and
p is 1 or 2, and (ii) those compounds of the general formulae:
wherein each R' is independently a hydrogen or halogen atom, or a C12 alkyl or nitro group;
R" is a hydrogen or halogen atom or a C14 alkyl or C14 alkoxy group;
Y' is a hydrogen atom or the group ZR4R5 wherein Z,R4 and R5 are as defined with reference to Formula I
X is O or S; and
p is 1 or 2.
In a similar manner pyrazinylcarbonyl phenyl ureas of the general formula:
wherein each R' is independently a hydrogen or halogen atom, or a C12 alkyl or nitro group:
each R"' is independently a hydrogen or halogen atom, or a C16 alkyl, nitro or cyanophenyl or halophenyl group; and
X is O or S may be employed.
In a preferred aspect of the present invention the non-aqueous solvent-flowable insecticide compositions contain not only the benzoyl phenyl urea, pyridylcarbonyl phenyl urea or pyrazinylcarbonyl phenyl urea suspended in the solvent, but also another insecticide dissolved in the solvent. Examples of insecticides which are soluble in most organic solvents and may thus be used in the compositions of the present invention are O,O-diethyl 0-(3,5,6-trichloro-2pyridyl)phosphorothioate (commonly called chlorpyrifos), O,O-dimethyl 0-(3,5, 6-trichloro-2-pyri- dyl)phosphorothioate (commonly called chlorpyrifosmethyl),diazinon, azodrin, parathion,methyl parathion, malathion, fenvalerate, cypermethrin, decamethrin, acephate and chlordane.
The emulsifier which is essential to the present invention is an alkaline earth metal, magnesium or aluminium salt of a branched chain C6-C,8 alkylarylsulphonic acid. Calcium salts are preferred and the alkylarylsulphonic acid is preferably a branched chain dodecyl or tridecylbenzenesulphonic acid. It will be understood that the commercially available dodecyl-(C,2) and tridecyl-(C,3)-benzenesulphonic acids contain other alkylbenzenesulphonic acids as impurities.
The emulsifier which is essential to the present invention is an anionic emulsifier and is usually present as a component of an emulsifier blend together with a non ionic emulsifier.
Suitable nonionic emulsifiers are the condensation products of fatty acids esters, fatty alcohols, fatty acid am ides or fatty acid amines with ethylene and/or propylene oxide, alkyl- or alkenylsubstituted phenols with ethylene and/or propylene oxide, fatty esters of polyhydric alcohol ethers e.g. sorbitan fatty acid esters, condensation products of such esters with ethylene oxide e.g. polyoxyethylene sorbitan fatty acid esters, block copolymers or ethylene oxide and propylene oxide, ethoxylated lanolin alcohols or ethoxylated lanolic acids.
The solvent which forms the base of the compositions of the invention may be any solvent which possess the desired solvent characteristics for the insecticides. The suspended insecticide should be essentially insoluble in the solvent, although a solubility of up to 700 ppm may be acceptable. The solvent should also keep a soluble insecticide, if present, in solution even at low temperature. Thus, by an appropriate choice of solvent, formulations may be prepared which are both suitable for ultra-low volume applications and emulsifiable in water for more conventional methods of application.
The suspending agent for the benzoyl phenyl urea, pyridylcarbonyl phenyl urea or pyrazinylcarbonyl phenyl urea insecticide may be any such agent which will maintain the insecticide in suspension in the solvent e.g. an organophilic clay such as Bentone (Registered Trade Mark), a fumed silica such as Cab-O-Sil (Registered Trade Mark), aluminium stearate, or a hydrogenated oil.
The compositions of the present invention will be further described with reference to the following Examples.
EXAMPLE 1
Two experiments were carried out to show the compatability between 1-(4-chlorophenyl)-3 (2,6-difluorobenzoyl)-urea and calcium dodecylbenzenesulphonate (Soprophor S 70).
1 g of 1 -(4-chlorophenyl)-3-(2,6-diflurobenzoyl) urea (Dimilin-Registered Trade Mark) and 1 g of calcium dodecylbenzenesulphonate (Soprophor S 70) were added to xylene (89). The slurry was stored at 55"C. It was found that when linear calcium dodecylbenzenesulphonate was used the slurry gelled to a solid mass, whereas when a branched chain calcium dodecylbenzenesulphonate was used the slurry did not gel.
EXAMPLE 2
Two experiments were carried out to show the compatability between 1-[4-(2,2-dichloro-1, 1difluoroethoxy)phenyl]-3-(2-chlorobenzoyl)urea and calcium dodecylbenzenesulphonate (Soprophor S 70).
1 g of 1-[4-2,2-dichloro-1,-difluoroethoxy)phenyl]-3-(2-chlorobenzoyl)urea and 19 of calcium dodecylbenzenesulphonate were added to Solvesso 200 (89) (Registered Trade Mark). The slurry was stored at 55"C. It was found that when a linear calcium dodecylbenzenesulphonate (Soprophor S 70) was used the slurry gelled to a solid mass, whereas when a branched chain calcium dodecylbenzenesulphonate was used the slurry did not gel.
EXAMPLE 3
(A) 480 g of O,O-diethyl 0-(3,5,6-trichloro-2-pyridyl) phosphorothioate were dissolved in 4709 of Solvesso 200 (Registered Trade Mark) and 459 of 1-(4-chlorophenyl)-3-(2,6-difluoro benzoyi)urea and 1 6g of Geopon GO-11 added thereto. The mixture was dispersed with a
Silverson mixer. Propylene carbonate (5.39), a branched chain calcium dodecylbenzenesulphonate (30g) (Soprophor S 70) and a nonylphenol ethoxylate surfactant (90g) (Ethylan KEO) were added thereto. The mixture was again homogenised and passed through a bead mill. The resultant liquid was stable and did not gel on storage.
(B) The procedure of part (A) was repeated, except that a linear calcium dodecylbenzenesulphonate was used instead of a branched chain calcium dodecylbenzenesulphonate. The resultant product was unstable on storage owing to gel formation.
EXAMPLE 4
4809 of O,O-diethyl 0-(3,5,6-trichloro-2-pyridyl) phosphorothioate were dissolved in 4359 of xylene and 309 of 1-(4-chlorophenyl)3-(2,6-difluorobenzoyl)urea and 1 Og of Armogel added thereto. The mixture was dispersed with a Silverson mixer. A branched chain calcium dodecylbenzenesulphonate (35g) (Soprophor S 70) and a castor-oil poly-glycol ether surfactant (65g) (Soprophor B) were added thereto. The mixture was again homogenised and passed through a bead mill.
The resultant liquid was a stable product which did not form a gel on storage.
EXAMPLE 5
The procedure of Example 3(A) was repeated except that 1 0g of Attagel 50 was incorporated at the same time as the Geopen GO-II.
A product was obtained which was slightly thicker than that obtained in Example 3(A). The product did not gel on storage.
This product, because of the slightly higher loading of solids due to the addition of Attagel 50, was less prone to syneresis that the product from Example 3(A).
Claims (14)
1. A non-aqueous solvent-flowable insecticide composition which comprises a solvent having suspended therein a substituted urea insecticide wherein the nitrogen atoms of the urea moiety are independently substituted with substituted or unsubstituted phenyl, benzoyl, pyridyl, pyrazinyl or benzopyrazinyl radicals and containing a suspending agent for the insecticide and an emulsifier which is an alkaline earth metal, magnesium or aluminium salt of a branched chain C6-C,8 alkylarylsulphonic acid.
2. A composition as claimed in claim 1 wherein the benzoyl phenyl urea insecticide is a compound of the general formula:
wherein R is a hydrogen or halogen atom, or a C12 alkyl or nitro group at position 2 and/or position 6; or a trimethylsilyl group;
R1 is a hydrogen or halogen atom, or an alkyl C12 group;
X is O or S;
Y is a halogen atom; C14 alkyl; C14 alkoxy; halosubstituted C14 alkyl-halosubstituted C14 alkoxy; halosubstituted C24 alkenyl; nitro; COOH;COOR3 wherein R3 is a C16 alkyl group; a phenoxy group substituted at the 4-position by cyano trifluoromethyl, nitro, C14 alkyl or alkoxy; a 2-pyridyloxy group substituted at the 5-position by cyano or trifluoromethyl; or Y is the group
ZR4R5 wherein
Z is O,S,SO,SO2 or NH;
R4 is C14 alkylene; and R5 is a phenyl or heterocyclic group;
m is 1 or 2; and
n is 1 or 2.
3. A composition as claimed in claim 2 wherein the benzoyl phenyl urea insecticide is a compound of the formula:
4. A composition as claimed in claim 2 wherein the benzoyl phenyl urea insecticide is a compound of the formula:
5. A composition as claimed in claim 2 wherein the benzoyl phenyl urea insecticide is a compound of the formula:
6. A composition as claimed in claim 1 wherein the pyridylcarbonyl phenyl urea insecticide is a compound of the formula:
wherein each R' is independently a hydrogen or halogen atom, or a C12 alkyl or nitro group;
R" is a hydrogen or halogen atom, or a C14 alkyl or C14 alkoxy group;
X is O or S; and
p is 1 or 2.
7. A composition as claimed in claim 1 wherein the pyridylcarbonyl phenyl urea insecticide is a compound of the formula:
wherein each R' is independently a hydrogen or halogen atom, or a C12 alkyl or nitro group; R" is a hydrogen or halogen atom, or a C, 4 alkyl or C14 alkoxy group; y' is a hydrogen atom or the group ZR4R5 wherein Z,R4 and R5 are as defined in claim 2
X is O or S; and
p is 1 or 2.
8. A composition as claimed in claim 1 wherein the pyrazinylcarbonyl phenyl urea insecticide is a compound of the formula:
wherein each R is independently a hydrogen or halogen atom, or a C12 alkyl or nitro group:
each R"' is independently a hydrogen or halogen atom, or a C1 6 alkyl, nitro or cyano group, phenyl or halophenyl; and
X is O or S.
9. A composition as claimed in any one of the preceding claims which includes an insecticide dissolved in the solvent.
10. A composition as claimed in claim 9 wherein the insecticide dissolved in the solvent is O,O-diethyl 0-(3,5,6-trichloro-2-pyridyl) phosphorothioate.
11. A composition as claimed in claim 9 wherein the insecticide dissolved in the solvent is
O,0-dimethyl 0-(3,5,6-trichloro-2-pyridyl) phosphorothioate.
12. A composition as claimed in any one of the preceding claims wherein the emulsifier is a calcium salt of a branched chain alkylbenzenesulphonic acid.
13. A composition as claimed in claim 12 wherein the emulsifier is a calcium salt of a branched chain dodecyl- or tridecyl-benzenesulphonic acid.
14. A composition as claimed in any one of the preceding claims wherein the emulsifier is a component of an emulsifier blend together with a non ionic emulsifier.
1 5. A composition as claimed in any one of the preceding claims wherein the solvent is a hydrocarbon.
1 6. A composition as claimed in any one of the preceding claims wherein the suspending agent is an organophilic clay.
1 7. A composition as claimed in claim 1 6 wherein the clay is modified by treatment with a long chain amine.
1 8. A composition as claimed in claim 1 substantially as hereinbefore described with reference to any one of Examples 3 to 5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8126638A GB2083360B (en) | 1980-09-03 | 1981-09-02 | Solvent-flowable compositions containing a substituted urea insecticide |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8028414 | 1980-09-03 | ||
| GB8126638A GB2083360B (en) | 1980-09-03 | 1981-09-02 | Solvent-flowable compositions containing a substituted urea insecticide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2083360A true GB2083360A (en) | 1982-03-24 |
| GB2083360B GB2083360B (en) | 1983-09-21 |
Family
ID=26276764
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8126638A Expired GB2083360B (en) | 1980-09-03 | 1981-09-02 | Solvent-flowable compositions containing a substituted urea insecticide |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2083360B (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0091756A2 (en) * | 1982-03-31 | 1983-10-19 | Rhone-Poulenc Nederland B.V. | Synergistic insecticidal composition |
| FR2529442A1 (en) * | 1982-06-30 | 1984-01-06 | Union Carbide Corp | SYNERGISTIC INSECTICIDE COMPOSITION CONTAINING BENZOYLIDEE AND ANOTHER PESTICIDE |
| GB2123294A (en) * | 1982-07-09 | 1984-02-01 | Chinoin Gyogyszer Es Vegyeszet | Stablized plant protecting agent suspension |
| GB2141628A (en) * | 1983-05-30 | 1985-01-03 | Ciba Geigy Ag | Synergistic pesticidal compositions |
| EP0149459A2 (en) * | 1984-01-18 | 1985-07-24 | S.I.P.C.A.M. S.p.A. Società Italiana Prodotti Chimici e per l'Agricoltura Milano | Stabilized fluid suspension of antiparasites in unchlorinated organic solvents and process for the preparation and use thereof |
| US4540578A (en) * | 1982-12-30 | 1985-09-10 | Union Carbide Corporation | Pesticidal phenoxypyridyl benzoyl ureas |
| US4602109A (en) * | 1982-12-30 | 1986-07-22 | Union Carbide Corporation | Novel pesticidal phenoxyphenyl and phenoxypyridyl benzoyl ureas and process for preparation |
| US4659724A (en) * | 1982-12-30 | 1987-04-21 | Union Carbide Corporation | Certain 1-[4-(5-cyano-2-pyridyloxy)phenyl-benzoyl ureas having pesticidal properties |
| US4767773A (en) * | 1982-06-30 | 1988-08-30 | Rhone-Poulenc Nederland B.V. | Synergistic insecticidal compositions |
| US4873264A (en) * | 1983-05-20 | 1989-10-10 | Rhone-Poulenc Nederlands B.V. | Novel pesticidal 1-(alkyl-phenoxy-aryl)-3-benzoyl ureas and process for preparation |
| US4880838A (en) * | 1982-06-30 | 1989-11-14 | Rhone-Poulenc | Pesticidal 1-(4-Phenoxyphenyl)-5-Benzoyl urea compounds and process for preparation |
| WO1995033380A1 (en) * | 1994-06-08 | 1995-12-14 | Ciba-Geigy Ag | Synergistic composition |
| EP0850564A1 (en) * | 1996-12-23 | 1998-07-01 | Maria Pilar Mateo Herrero | Emulsifiable vinylic concentrate inhibiting the chitin synthesis in arthropods, for the control of pests and allergens |
| WO2000018227A1 (en) * | 1998-09-25 | 2000-04-06 | American Cyanamid Company | Non-aqueous suspension concentrate |
| US6165940A (en) * | 1998-09-25 | 2000-12-26 | American Cyanamid Co. | Non-aqueous suspension concentrate |
-
1981
- 1981-09-02 GB GB8126638A patent/GB2083360B/en not_active Expired
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0091756A3 (en) * | 1982-03-31 | 1984-11-07 | Union Carbide Corporation | Synergistic insecticidal composition |
| EP0091756A2 (en) * | 1982-03-31 | 1983-10-19 | Rhone-Poulenc Nederland B.V. | Synergistic insecticidal composition |
| US4880838A (en) * | 1982-06-30 | 1989-11-14 | Rhone-Poulenc | Pesticidal 1-(4-Phenoxyphenyl)-5-Benzoyl urea compounds and process for preparation |
| FR2529442A1 (en) * | 1982-06-30 | 1984-01-06 | Union Carbide Corp | SYNERGISTIC INSECTICIDE COMPOSITION CONTAINING BENZOYLIDEE AND ANOTHER PESTICIDE |
| GB2122494A (en) * | 1982-06-30 | 1984-01-18 | Union Carbide Corp | Synergistic insecticidal composition |
| US4767773A (en) * | 1982-06-30 | 1988-08-30 | Rhone-Poulenc Nederland B.V. | Synergistic insecticidal compositions |
| TR22553A (en) * | 1982-06-30 | 1987-10-22 | Union Carbide Corp | SYNERGISTIC COMPOUNDS THAT CAN BE USED AS SPECIFIC BENZOIL URERES AND PESTICIDES INTENTION INDEX |
| GB2123294A (en) * | 1982-07-09 | 1984-02-01 | Chinoin Gyogyszer Es Vegyeszet | Stablized plant protecting agent suspension |
| US4540578A (en) * | 1982-12-30 | 1985-09-10 | Union Carbide Corporation | Pesticidal phenoxypyridyl benzoyl ureas |
| US4602109A (en) * | 1982-12-30 | 1986-07-22 | Union Carbide Corporation | Novel pesticidal phenoxyphenyl and phenoxypyridyl benzoyl ureas and process for preparation |
| US4659724A (en) * | 1982-12-30 | 1987-04-21 | Union Carbide Corporation | Certain 1-[4-(5-cyano-2-pyridyloxy)phenyl-benzoyl ureas having pesticidal properties |
| US4873264A (en) * | 1983-05-20 | 1989-10-10 | Rhone-Poulenc Nederlands B.V. | Novel pesticidal 1-(alkyl-phenoxy-aryl)-3-benzoyl ureas and process for preparation |
| GB2178317A (en) * | 1983-05-30 | 1987-02-11 | Ciba Geigy Ag | Pesticidal compositions |
| GB2141628A (en) * | 1983-05-30 | 1985-01-03 | Ciba Geigy Ag | Synergistic pesticidal compositions |
| EP0149459A2 (en) * | 1984-01-18 | 1985-07-24 | S.I.P.C.A.M. S.p.A. Società Italiana Prodotti Chimici e per l'Agricoltura Milano | Stabilized fluid suspension of antiparasites in unchlorinated organic solvents and process for the preparation and use thereof |
| EP0149459A3 (en) * | 1984-01-18 | 1985-08-28 | S.I.P.C.A.M. S.p.A. Società Italiana Prodotti Chimici e per l'Agricoltura Milano | Stabilized fluid suspension of antiparasites in unchlorinated organic solvents and process for the preparation and use thereof |
| WO1995033380A1 (en) * | 1994-06-08 | 1995-12-14 | Ciba-Geigy Ag | Synergistic composition |
| EP1642501A2 (en) * | 1994-06-08 | 2006-04-05 | Syngenta Participations AG | Synergistic compositions comprising lufenuron and fenoxycarb |
| EP1642501A3 (en) * | 1994-06-08 | 2009-10-21 | Syngenta Participations AG | Synergistic compositions comprising lufenuron and fenoxycarb |
| EP2260707A2 (en) * | 1994-06-08 | 2010-12-15 | Syngenta Participations AG. | Synergistic compositions comprising lufenuron |
| EP2260707A3 (en) * | 1994-06-08 | 2013-07-24 | Syngenta Participations AG. | Synergistic compositions comprising lufenuron |
| EP0850564A1 (en) * | 1996-12-23 | 1998-07-01 | Maria Pilar Mateo Herrero | Emulsifiable vinylic concentrate inhibiting the chitin synthesis in arthropods, for the control of pests and allergens |
| WO2000018227A1 (en) * | 1998-09-25 | 2000-04-06 | American Cyanamid Company | Non-aqueous suspension concentrate |
| US6165940A (en) * | 1998-09-25 | 2000-12-26 | American Cyanamid Co. | Non-aqueous suspension concentrate |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2083360B (en) | 1983-09-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19960902 |