CA1050041A - Insecticide especially of colorado-beetle killing action - Google Patents
Insecticide especially of colorado-beetle killing actionInfo
- Publication number
- CA1050041A CA1050041A CA101,659A CA101659A CA1050041A CA 1050041 A CA1050041 A CA 1050041A CA 101659 A CA101659 A CA 101659A CA 1050041 A CA1050041 A CA 1050041A
- Authority
- CA
- Canada
- Prior art keywords
- phosphate
- bromovinyl
- dichlorophenyl
- compound
- formula
- 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.)
- Expired
Links
- 241000258916 Leptinotarsa decemlineata Species 0.000 title claims abstract description 12
- 239000002917 insecticide Substances 0.000 title claims abstract description 10
- 230000002147 killing effect Effects 0.000 title claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 239000013543 active substance Substances 0.000 claims abstract description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 16
- 239000010452 phosphate Substances 0.000 claims description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 16
- 241000254173 Coleoptera Species 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 description 21
- 241000607479 Yersinia pestis Species 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 5
- 230000001276 controlling effect Effects 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- FSAVDKDHPDSCTO-WQLSENKSSA-N [(z)-2-chloro-1-(2,4-dichlorophenyl)ethenyl] diethyl phosphate Chemical compound CCOP(=O)(OCC)O\C(=C/Cl)C1=CC=C(Cl)C=C1Cl FSAVDKDHPDSCTO-WQLSENKSSA-N 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- 229940078552 o-xylene Drugs 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000004224 protection Effects 0.000 description 4
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000012875 nonionic emulsifier Substances 0.000 description 2
- 239000002420 orchard Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000010454 slate Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- KLAQAAQATGGTTQ-UHFFFAOYSA-N 2-bromoethenyl dihydrogen phosphate Chemical compound OP(O)(=O)OC=CBr KLAQAAQATGGTTQ-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- -1 aliphatic alcohols Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229940088623 biologically active substance Drugs 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000035611 feeding Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
ABSTRACT
The invention relates to novel compounds of general formula
The invention relates to novel compounds of general formula
Description
~SOO~l The invention relates to novel compolmds of general formula R ~ ~ 0 / \
R0 0-C=CHBr wherein R denotes a lo ~ ar weight alkyl radical containing 1-3 carbon atoms, and n denotes the integral number 1 or 2; and to insecticides, especial-ly for exterminating the Colorado-beetle. From among many known insecticides there is merely a small number that show enough Colorado-beetle killing action to be used for p~otecting the potato against one of the most dangerous pests, the Colorado potato beetle, Up to now, generally used preparations have been insecticidal mixtures, the main active component of which is l,l,l-trichloro-
R0 0-C=CHBr wherein R denotes a lo ~ ar weight alkyl radical containing 1-3 carbon atoms, and n denotes the integral number 1 or 2; and to insecticides, especial-ly for exterminating the Colorado-beetle. From among many known insecticides there is merely a small number that show enough Colorado-beetle killing action to be used for p~otecting the potato against one of the most dangerous pests, the Colorado potato beetle, Up to now, generally used preparations have been insecticidal mixtures, the main active component of which is l,l,l-trichloro-
2,2'-(4-chlorophenyl)-ethane (DDT). But as pests become immunized against the action of DDT and other compounds applied for a longer time, obtaining an effective pest extermination result requires a considerable increase of the quantity of preparations used in the protective measures.
There have also been found other negative features of DDT, as, above all, its remaining for a long time in the soil, depositing in the tissues of living organisms, also with animals and men, and occurrence in greater and greater amounts in food products.
The above mentioned disadvantageous features of DDT caused a remark-able limitation, in some countries even a severe prohibition, of its applica-tion in the protection of plants designed for consumption.
Widely performed investigations resulted in finding a compound of a very strong Colorado beetle killing action, This compound, of the common name chlorphenvinphos being 0,0-diethyl-0-1-(2,4-dichlorophenyl)-2-chloro-vinyl phosphate, i.s ho~ever very toxic to warm-blooded organisms, whereby its range of application in the protection of plants is considerably limited.
The above mentioned difficulties in the protection of plants, especially of the potato against its main pest, the Colorado beetle, are re-moved by the preparation according to the present invention which as the bio-logically active substance contains 0,0-dialkyl-0-1-/mono- and dichlorophenyl/-- 1 - 3~k ~05(~
2- bromovinyl phosphate of the general formula 1, in which R denotes a low-molecular-weight alkyl group containing 1 - 3 carbon atoms, and n denotes the integral number 1 or 2; and particularly, 0,0-diethyl-0~1-(2,4-dichlorophenyl) -2-bromovinyl phosphate of the formula 2, and 0,0-dimethyl-0-1-(2,~ dichloro-phenyl)-2-bromovinyl phosphate of formula 3 and 0,0-di~n- or iso-) propyl-0-1 -(2,4-dichlorophenyl)-2-bromovinyl phosphate of formula 4.
The insecticide according to the invention containing the compound of formula 1 shows the advantage that when compared with a known preparation containing as the active substance Chlorphenvinphos and actually considered to be the most effective in controlling the Colorado potato beetle, it is high-ly effective in controlling harmful insects, including the Colorado potato beetle (table 1) with simultaneously lower toxicity in relation to warm-blooded animals and men (table 2) Furthe~more, compounds of formula 1 constituting the active substance of the preparation according to the invention are characteri7ed by a quick decomposition and by the fact that they do not accumulate in a natural medium nor in food products. The preparation according to the invention, and parti-cularly the one which contains the compound of formula 3, is completely safe in use, as regards toxicity, and can generally be recommended for the protec-tion of orchards and vegetables, as well as for controlling sanitary pests andparasites of domestic animals.
T a b 1 e Insecticidal action on the house-fly and Colorado potato beetle of the preparation according to the invention in comparison with standard insec-ticides 304~
Name of I llouse-fly I Colorado potato the compound I ~g/female I beetle ~g/beetle 50 ¦ 95 1 5() 1 95 Compound of formula 2 1 0,12 0,18 0,8 2,7 Compound of formula 3 10,06 10,13 1 2~5 1 6,4 Chlorphenvinphos ~ 0,052 1 0,08~3 1 1,2 1 2,6 10 DDT I 0,41 ¦6,37 ¦153,0 1 1268,0 T a b 1 e 2 Acute toxicity "per os" to the rate of the preparation according to the invention in comparison with standard insecticides Name of ~ LD50 the compound I mg/kg 20 I Compound of formula 2 1 63,5 I Compound of formula 3 1 224,5 Chlorphenvinphos 1 14,5 DDT ¦ 194 - 800 /
, _ x/ According to "Evolution of some pestice residue in food"
FAO/WH0, 1967 According to the invention, the insecticidal compositions comprise, in addition to the active substance of the general formula 1, at least one com-30 ponent such as e.g. an emulsifying agent, wetting agent, or dispersing agent,carrier, solvent, stabilizing agent, adhesion improver. Thus there exis~s the possibility of applying a number of hereafter described known application forms 10510~4~
of the preparation.
As aqueous application forms can be used: solutions for emulsifying, pastes or suspension powders. As the emulsifying or dispersing agents, non-ionic products, such as e.g. condensation products of ethylene oxide with aliphatic alcohols, amines or carboxylic acids, of a chain containing 10 - 30 carbon atoms, ionic products, such as e.g. salts of alkyl aryl sulphonic acids or of aliphatic alcohol sulphoesters, of fatty acids of a chain containing up to 25 carbon atoms, of sulphonaphthenic acids, quaternary phosphonium and ammonium compounds or mixtures of the above substances, can be used.
Application forms of the preparation used in form of a powder, dust or granules, may contain such mineral carriers as talc, kaolin, bentonite, diatomaceous earth,synthetic silica etc.
The preparation according to the invention can be used for controll-ing the Colorado potato beetle, pests injurious to orchards, vegetables, feed-ing stuff plants, industrial plants, for controlling warehouse pests, forest pests, infectious disease carrying insects, sanitary pests and insect-parasites of animals, Example 1. A preparation in form of a 25% emulsifiable solution is obtainable by mixing 500 g of 0,0-diethyl-0-1-(2,4-dichlorophenyl)-2-bromovinyl phosphate of formula 2 with 1450 g of o-xylene and 50 g of a mixture of anionic and non-ionic emulsifiers.
Example 11. A preparation in form of a 50% emulsifiable solution is obtainable by mixing 1000 g of 0,0-dimethyl-0-1-~2,4-dichlorophenyl)-2-bromovinyl phosphate of formula 3 with 950 g of o-xylene and 50 g of a mixture of anionic and non-ionic emulsifiers.
Example 111. A preparation in form of a 10% oily solution for drop-let spraying is obtainable by mixing 200 g of 0,0-diethyl-0-1-~ 2,4-dic'nloro-phenyl)-2-bromovinyl phosphate of formula 2 with 1600 g of spindle oil and 200 g of paraffin oil.
Example lV. A preparation in form of a 5% powder for sprinkling is obtainable by mixing 100 g of O~o-dimethyl-o-l-~2~4-dichlorophenyl)-2-bromo-~inyl phosphate of formula 3 in a pan crusher with 500 g of pyrophylite slate.
~C~5004~
The mixture thus obtained is then diluted in a high-speed propeller agitator with a further amount of 1400 g of pyrophylite slate.
Example V. A preparation in form of a 50% suspension powder is obtained as follows: 1000 g of 0,0-dimethyl-0-1-(2,4-dichlorophenyl)-2-bromovinyl phosphate of formula 3, 300 g of Ultrasil type synthetic silica, 600 g of Kaolin, ~0 g of klutan and 10 g of S Nekaline* are mixed first in a pan crusher and then in a high-speed propeller agitator.
Example Vl. A preparation in form of 5% granules is obtained as follows: 100 g of 0,0-diethyl-0-1-~2,4-dichlorophenyl)-2-bromovinyl pho~phate of formula 2 and 5 g of a non-ionic emulsifier of 14,0 - 16,0 HLB is dissolved in 95 g of o-xylene and then the solution thus obtained is mixed with 1~00 g of granulated diatomite.
Example Vll. A preparation in form of a 20% fluid preparation for veterinary pllrposes is obtained by mixing 200 g of 0,0-dimethyl-0-1-(2,4-dichlorophenyl)-2-bromovinyl phosphate of formula 3 with 300 g of paraffin oil, 400 g of spi.ndle oil and 100 g of a non-ionic emulsifier of 13,0 - 16,0 HLB.
Example Vlll. A preparation for sanitary purposes is obtained by mixing 20 g of 0,0-dimethyl-0-1-(2,4-dichlorophenyl)-2-bromovinyl phosphate and 200 g of Freon.*
Example lX. A preparation in form of a 25% emulsifiable solution is obtained by mixing 500 g of 0,0-diisopropyl-0-1-(2,4-dichlorophenyl)-2-bromovinyl phosphate of formula 4 with 1450 g of o-xylene and 50 g of a mix-ture of anionic and non-ionic emulsifiers.
* Trademarks ~L05~41 \ ~
p 0 - C = CHBr ~ Cln formula 1 C2 5 \
p C2H50 ~ C = CHBr ~Cl
There have also been found other negative features of DDT, as, above all, its remaining for a long time in the soil, depositing in the tissues of living organisms, also with animals and men, and occurrence in greater and greater amounts in food products.
The above mentioned disadvantageous features of DDT caused a remark-able limitation, in some countries even a severe prohibition, of its applica-tion in the protection of plants designed for consumption.
Widely performed investigations resulted in finding a compound of a very strong Colorado beetle killing action, This compound, of the common name chlorphenvinphos being 0,0-diethyl-0-1-(2,4-dichlorophenyl)-2-chloro-vinyl phosphate, i.s ho~ever very toxic to warm-blooded organisms, whereby its range of application in the protection of plants is considerably limited.
The above mentioned difficulties in the protection of plants, especially of the potato against its main pest, the Colorado beetle, are re-moved by the preparation according to the present invention which as the bio-logically active substance contains 0,0-dialkyl-0-1-/mono- and dichlorophenyl/-- 1 - 3~k ~05(~
2- bromovinyl phosphate of the general formula 1, in which R denotes a low-molecular-weight alkyl group containing 1 - 3 carbon atoms, and n denotes the integral number 1 or 2; and particularly, 0,0-diethyl-0~1-(2,4-dichlorophenyl) -2-bromovinyl phosphate of the formula 2, and 0,0-dimethyl-0-1-(2,~ dichloro-phenyl)-2-bromovinyl phosphate of formula 3 and 0,0-di~n- or iso-) propyl-0-1 -(2,4-dichlorophenyl)-2-bromovinyl phosphate of formula 4.
The insecticide according to the invention containing the compound of formula 1 shows the advantage that when compared with a known preparation containing as the active substance Chlorphenvinphos and actually considered to be the most effective in controlling the Colorado potato beetle, it is high-ly effective in controlling harmful insects, including the Colorado potato beetle (table 1) with simultaneously lower toxicity in relation to warm-blooded animals and men (table 2) Furthe~more, compounds of formula 1 constituting the active substance of the preparation according to the invention are characteri7ed by a quick decomposition and by the fact that they do not accumulate in a natural medium nor in food products. The preparation according to the invention, and parti-cularly the one which contains the compound of formula 3, is completely safe in use, as regards toxicity, and can generally be recommended for the protec-tion of orchards and vegetables, as well as for controlling sanitary pests andparasites of domestic animals.
T a b 1 e Insecticidal action on the house-fly and Colorado potato beetle of the preparation according to the invention in comparison with standard insec-ticides 304~
Name of I llouse-fly I Colorado potato the compound I ~g/female I beetle ~g/beetle 50 ¦ 95 1 5() 1 95 Compound of formula 2 1 0,12 0,18 0,8 2,7 Compound of formula 3 10,06 10,13 1 2~5 1 6,4 Chlorphenvinphos ~ 0,052 1 0,08~3 1 1,2 1 2,6 10 DDT I 0,41 ¦6,37 ¦153,0 1 1268,0 T a b 1 e 2 Acute toxicity "per os" to the rate of the preparation according to the invention in comparison with standard insecticides Name of ~ LD50 the compound I mg/kg 20 I Compound of formula 2 1 63,5 I Compound of formula 3 1 224,5 Chlorphenvinphos 1 14,5 DDT ¦ 194 - 800 /
, _ x/ According to "Evolution of some pestice residue in food"
FAO/WH0, 1967 According to the invention, the insecticidal compositions comprise, in addition to the active substance of the general formula 1, at least one com-30 ponent such as e.g. an emulsifying agent, wetting agent, or dispersing agent,carrier, solvent, stabilizing agent, adhesion improver. Thus there exis~s the possibility of applying a number of hereafter described known application forms 10510~4~
of the preparation.
As aqueous application forms can be used: solutions for emulsifying, pastes or suspension powders. As the emulsifying or dispersing agents, non-ionic products, such as e.g. condensation products of ethylene oxide with aliphatic alcohols, amines or carboxylic acids, of a chain containing 10 - 30 carbon atoms, ionic products, such as e.g. salts of alkyl aryl sulphonic acids or of aliphatic alcohol sulphoesters, of fatty acids of a chain containing up to 25 carbon atoms, of sulphonaphthenic acids, quaternary phosphonium and ammonium compounds or mixtures of the above substances, can be used.
Application forms of the preparation used in form of a powder, dust or granules, may contain such mineral carriers as talc, kaolin, bentonite, diatomaceous earth,synthetic silica etc.
The preparation according to the invention can be used for controll-ing the Colorado potato beetle, pests injurious to orchards, vegetables, feed-ing stuff plants, industrial plants, for controlling warehouse pests, forest pests, infectious disease carrying insects, sanitary pests and insect-parasites of animals, Example 1. A preparation in form of a 25% emulsifiable solution is obtainable by mixing 500 g of 0,0-diethyl-0-1-(2,4-dichlorophenyl)-2-bromovinyl phosphate of formula 2 with 1450 g of o-xylene and 50 g of a mixture of anionic and non-ionic emulsifiers.
Example 11. A preparation in form of a 50% emulsifiable solution is obtainable by mixing 1000 g of 0,0-dimethyl-0-1-~2,4-dichlorophenyl)-2-bromovinyl phosphate of formula 3 with 950 g of o-xylene and 50 g of a mixture of anionic and non-ionic emulsifiers.
Example 111. A preparation in form of a 10% oily solution for drop-let spraying is obtainable by mixing 200 g of 0,0-diethyl-0-1-~ 2,4-dic'nloro-phenyl)-2-bromovinyl phosphate of formula 2 with 1600 g of spindle oil and 200 g of paraffin oil.
Example lV. A preparation in form of a 5% powder for sprinkling is obtainable by mixing 100 g of O~o-dimethyl-o-l-~2~4-dichlorophenyl)-2-bromo-~inyl phosphate of formula 3 in a pan crusher with 500 g of pyrophylite slate.
~C~5004~
The mixture thus obtained is then diluted in a high-speed propeller agitator with a further amount of 1400 g of pyrophylite slate.
Example V. A preparation in form of a 50% suspension powder is obtained as follows: 1000 g of 0,0-dimethyl-0-1-(2,4-dichlorophenyl)-2-bromovinyl phosphate of formula 3, 300 g of Ultrasil type synthetic silica, 600 g of Kaolin, ~0 g of klutan and 10 g of S Nekaline* are mixed first in a pan crusher and then in a high-speed propeller agitator.
Example Vl. A preparation in form of 5% granules is obtained as follows: 100 g of 0,0-diethyl-0-1-~2,4-dichlorophenyl)-2-bromovinyl pho~phate of formula 2 and 5 g of a non-ionic emulsifier of 14,0 - 16,0 HLB is dissolved in 95 g of o-xylene and then the solution thus obtained is mixed with 1~00 g of granulated diatomite.
Example Vll. A preparation in form of a 20% fluid preparation for veterinary pllrposes is obtained by mixing 200 g of 0,0-dimethyl-0-1-(2,4-dichlorophenyl)-2-bromovinyl phosphate of formula 3 with 300 g of paraffin oil, 400 g of spi.ndle oil and 100 g of a non-ionic emulsifier of 13,0 - 16,0 HLB.
Example Vlll. A preparation for sanitary purposes is obtained by mixing 20 g of 0,0-dimethyl-0-1-(2,4-dichlorophenyl)-2-bromovinyl phosphate and 200 g of Freon.*
Example lX. A preparation in form of a 25% emulsifiable solution is obtained by mixing 500 g of 0,0-diisopropyl-0-1-(2,4-dichlorophenyl)-2-bromovinyl phosphate of formula 4 with 1450 g of o-xylene and 50 g of a mix-ture of anionic and non-ionic emulsifiers.
* Trademarks ~L05~41 \ ~
p 0 - C = CHBr ~ Cln formula 1 C2 5 \
p C2H50 ~ C = CHBr ~Cl
3 formula 2 \p~
/ \
CH30 0 - C = CHBr ¢~Cl ~1 folmula 3 C3H70 \ / 0 (n- or iso-) P
C3H70 ~ C = CHBr ~CI
formula 4
/ \
CH30 0 - C = CHBr ¢~Cl ~1 folmula 3 C3H70 \ / 0 (n- or iso-) P
C3H70 ~ C = CHBr ~CI
formula 4
Claims (5)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A compound of general formula in which R denotes a low-molecular-weight alkyl radical containing 1-3 carbon atoms, and n denotes the integral number 1 or 2.
2. The compound 0,0-diethyl-0-1-(2,4-dichlorophenyl)-2-bromovinyl phosphate, being a compound according to claim 1.
3. The compound 0,0-dimethyl-0-1-(2,4-dichlorophenyl)-2-bromovinyl phosphate, being a compound according to claim 1.
4. A method of killing Colorado-beetle comprising applying to the beetle habitat an insecticide characterized in that it contains as the active substance a compound of the formula in which R denotes a low-molecular-weight alkyl radical containing 1-3 carbon atoms, and n denotes the integral number 1 or 2, together with a carrier.
5. A method according to claim 4 wherein said insecticide contains as active substance one of 0,0-diethyl-0-1-(2,4-dichlorophenyl)-2-bromovinyl phosphate; 0,0-dimethyl-0-1-(2,4-dichlorophenyl)-2-bromovinyl phosphate; or 0,0-di(n- or iso)propyl-0-1-(2,4-dichlorophenyl)-2-bromovinyl phosphate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL13783069A PL79031B1 (en) | 1969-12-29 | 1969-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1050041A true CA1050041A (en) | 1979-03-06 |
Family
ID=19951112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA101,659A Expired CA1050041A (en) | 1969-12-29 | 1970-12-29 | Insecticide especially of colorado-beetle killing action |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS541775B1 (en) |
| BE (1) | BE760040A (en) |
| BG (1) | BG17716A3 (en) |
| CA (1) | CA1050041A (en) |
| CH (1) | CH545066A (en) |
| CS (1) | CS154311B2 (en) |
| DE (1) | DE2059071A1 (en) |
| FR (1) | FR2072090B1 (en) |
| GB (1) | GB1303470A (en) |
| NL (1) | NL153064B (en) |
| PL (1) | PL79031B1 (en) |
| RO (2) | RO67871A (en) |
| SU (1) | SU362525A3 (en) |
-
0
- BE BE760040D patent/BE760040A/en unknown
-
1969
- 1969-12-29 PL PL13783069A patent/PL79031B1/xx unknown
-
1970
- 1970-12-01 DE DE19702059071 patent/DE2059071A1/en not_active Withdrawn
- 1970-12-04 GB GB565670A patent/GB1303470A/en not_active Expired
- 1970-12-14 CH CH1852370A patent/CH545066A/en not_active IP Right Cessation
- 1970-12-15 NL NL7018254A patent/NL153064B/en not_active IP Right Cessation
- 1970-12-15 BG BG016320A patent/BG17716A3/en unknown
- 1970-12-23 FR FR7046483A patent/FR2072090B1/fr not_active Expired
- 1970-12-25 SU SU1604774A patent/SU362525A3/ru active
- 1970-12-28 CS CS882270A patent/CS154311B2/cs unknown
- 1970-12-28 JP JP12514670A patent/JPS541775B1/ja active Pending
- 1970-12-28 RO RO7084327A patent/RO67871A/en unknown
- 1970-12-28 RO RO6542670A patent/RO63399A/en unknown
- 1970-12-29 CA CA101,659A patent/CA1050041A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2072090A1 (en) | 1971-09-24 |
| CS154311B2 (en) | 1974-03-29 |
| BG17716A3 (en) | 1973-12-25 |
| JPS541775B1 (en) | 1979-01-29 |
| NL153064B (en) | 1977-05-16 |
| FR2072090B1 (en) | 1975-01-10 |
| RO67871A (en) | 1981-06-22 |
| SU362525A3 (en) | 1972-12-13 |
| CH545066A (en) | 1973-12-15 |
| RO63399A (en) | 1978-07-15 |
| BE760040A (en) | 1971-05-17 |
| DE2059071A1 (en) | 1971-07-01 |
| NL7018254A (en) | 1971-07-01 |
| GB1303470A (en) | 1973-01-17 |
| PL79031B1 (en) | 1975-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100405400B1 (en) | Insecticidal combinations including an insecticide from the chloronicotinyl family and an insecticide having a pyrazole, pyrrole or phenylimidazole group | |
| CA1169769A (en) | Synergistic insecticidal compositions | |
| KR100357353B1 (en) | Oil-in-water emulsion | |
| US3683078A (en) | Transparent toxicant compositions | |
| CS227693B2 (en) | Insecticide and method of its preparation | |
| US3628941A (en) | Antimicrobial solutions of dodecylguanidine hydrochloride having low-temperature stability | |
| CA1050041A (en) | Insecticide especially of colorado-beetle killing action | |
| US2861876A (en) | Method of destroying undesired plants | |
| US4133878A (en) | Stabilized organothiophosphorus formulations | |
| US4380537A (en) | Stabilized insecticide formulations | |
| CA1198670A (en) | Pesticidal formulations | |
| JPS5827768B2 (en) | Insecticidal composition for high-concentration micro-spraying | |
| DE2202471A1 (en) | New esters | |
| IL28155A (en) | Method for combatting nematodes and preparations for use in such method | |
| US3116335A (en) | Organic sulfur-containing compounds | |
| US3051614A (en) | Heavy oil for tree spray | |
| KR880002244B1 (en) | Compositions for controlling parasites of rice | |
| US2976311A (en) | Dithiophosphoric acid esters | |
| GB2095114A (en) | Antifungal compositions based on phosphorous acid derivatives, and their application to the protection of plants | |
| IL37390A (en) | Imidazolyl-alkyl-thiophosphates and thiophosphonates,their manufacture and their use as pesticides | |
| US3530206A (en) | O,o-diloweralkyl-o - (2-chloro - 4 - bromo phenyl) phosphates and thiophosphates | |
| US3096238A (en) | Omicron-(halophenyl) phosphonothioates | |
| CA2036469A1 (en) | Concentrated aqueous emulsions of neophanes and azaneophanes for use in plant protection | |
| US3755564A (en) | Synergistic insecticidal composition of diazinon and a certain carbamate | |
| KR840000836B1 (en) | Pesticidal compositions |