CA1050041A - Insecticide especially of colorado-beetle killing action - Google Patents

Insecticide especially of colorado-beetle killing action

Info

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
Application number
CA101,659A
Other languages
French (fr)
Other versions
CA101659S (en
Inventor
Jozef Kroczynski
Jan M. Swiech
Kazimierz-Jerzy Goreckji
Ludwika Cieslak
Stefan-Janusz Fulde
Edmund-Henryk Bakuniak
Aleksander J. Majda
Stefan Mosinski
Bohdan-Stanislaw Sledzinski
Romuald Malinowski
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.)
Instytut Przemyslu Organicznego
Original Assignee
Instytut Przemyslu Organicznego
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 Instytut Przemyslu Organicznego filed Critical Instytut Przemyslu Organicznego
Application granted granted Critical
Publication of CA1050041A publication Critical patent/CA1050041A/en
Expired legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N57/00Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/14Biocides, 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/08Esters of oxyacids of phosphorus
    • C07F9/09Esters of phosphoric acids
    • C07F9/113Esters 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

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-
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
3 formula 2 \p~
/ \
CH30 0 - C = CHBr ¢~Cl ~1 folmula 3 C3H70 \ / 0 (n- or iso-) P
C3H70 ~ C = CHBr ~CI

formula 4

Claims (5)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
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.
CA101,659A 1969-12-29 1970-12-29 Insecticide especially of colorado-beetle killing action Expired CA1050041A (en)

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)

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

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