GB1592229A - Pesticidal formulations - Google Patents
Pesticidal formulations Download PDFInfo
- Publication number
- GB1592229A GB1592229A GB2426578A GB2426578A GB1592229A GB 1592229 A GB1592229 A GB 1592229A GB 2426578 A GB2426578 A GB 2426578A GB 2426578 A GB2426578 A GB 2426578A GB 1592229 A GB1592229 A GB 1592229A
- Authority
- GB
- United Kingdom
- Prior art keywords
- esters
- decamethrin
- permethrin
- foregoing
- weight
- 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
- 239000000203 mixture Substances 0.000 title claims description 22
- 238000009472 formulation Methods 0.000 title claims description 10
- 230000000361 pesticidal effect Effects 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 27
- 150000002148 esters Chemical class 0.000 claims description 18
- 229960002483 decamethrin Drugs 0.000 claims description 15
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 claims description 15
- 229960000490 permethrin Drugs 0.000 claims description 15
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 claims description 15
- -1 95V aromatic hydrocarbons Chemical class 0.000 claims description 9
- 241000238421 Arthropoda Species 0.000 claims description 9
- 244000078703 ectoparasite Species 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 241000238876 Acari Species 0.000 claims description 6
- 239000003995 emulsifying agent Substances 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- QFMDFTQOJHFVNR-UHFFFAOYSA-N 1-[2,2-dichloro-1-(4-ethylphenyl)ethyl]-4-ethylbenzene Chemical compound C1=CC(CC)=CC=C1C(C(Cl)Cl)C1=CC=C(CC)C=C1 QFMDFTQOJHFVNR-UHFFFAOYSA-N 0.000 claims description 4
- 241000238680 Rhipicephalus microplus Species 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- LLMLSUSAKZVFOA-UJURSFKZSA-N (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(O)=O LLMLSUSAKZVFOA-UJURSFKZSA-N 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000003921 oil Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- IEORSVTYLWZQJQ-UHFFFAOYSA-N 2-(2-nonylphenoxy)ethanol Chemical compound CCCCCCCCCC1=CC=CC=C1OCCO IEORSVTYLWZQJQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005995 Aluminium silicate Substances 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 claims description 2
- 238000007598 dipping method Methods 0.000 claims description 2
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 2
- 239000002608 ionic liquid Substances 0.000 claims 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 claims description 2
- 229920000847 nonoxynol Polymers 0.000 claims description 2
- 229920001521 polyalkylene glycol ether Polymers 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 238000005507 spraying Methods 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 239000004563 wettable powder Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 13
- 241000607479 Yersinia pestis Species 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 1
- IDVSZKGRCBMUQW-UHFFFAOYSA-N 2-(2,2-dichloroethenyl)-1,1-dimethylcyclopropane Chemical compound CC1(C)CC1C=C(Cl)Cl IDVSZKGRCBMUQW-UHFFFAOYSA-N 0.000 description 1
- 206010060969 Arthropod infestation Diseases 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical group C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- 241001555556 Ephestia elutella Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- 241000130767 Tineidae Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Landscapes
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
(54) PESTICIDAL FORMULATIONS
(71) We, THE WELLCOME FOUNDATION LIMITED, of 183-193 -Euston Road, London, N.W.I, a company incorporated in England do hereby
declare that the invention for which we pray that a Patent may be granted to us and the method by which it is performed, to be particularly described in and by the
following statement:- This invention relates to novel potentiating compositions, their preparation
formulations containing them, the preparation of such formulations and to their use for the control of arthropod pests.
Arthropod pests are troublesome to man, animal and plants. They are vectors
of disease, and ecomomic losses result from their depredations on plants and
animals. Control of such pests over the years has come to depend strongly upon the
use of chemical pesticides, and prominent amongst those which have been
extensively investigated are pyrethroids-esters of -cyclopropane carboxylic acid
derivatives.
Amongst pyrethroids known to be active against a variety of arthropod pests
are the compounds of formula (I). These are disclosed in British Patent
Specifications Nos. 1413491 and 1448228 and include a number of compounds
having considerable potency as insecticides.
It has now been found that the activity against arthropod pests of one
compound of formula (I) can be potentiated by another compound of formula (I).
For example, the ixodicidal activities of the compounds 3 - phenoxybenzyl (+)
cis, trans - 2,2 - dimethyl - 3 - (2,2 - dichlorovinyl) cyclopropane - 1 - carboxylate (permethrin) and (-) - a - cyano .3 - phenoxybenzyl (+) - cis - 2,2
dimethyl .3 - (2,2 - dibromovinyl) cyclopropane - I - carboxylate (decamethrin)
are potentiated by mixtures of these compounds when tested against the cattle tick
Boophilus microplus.
In the compounds of formula (I):
R2 represents halo and R3 represents alkyl or halo; R represents a group of the formula:
wherein
Z represents 0, S, CH2 or CO, Y represents hydrogen, alkyl, alkenyl or alkynyl, or aryl or furyl which is unsubstituted or substituted in the ring by one or more alkyl, alkenyl, alkoxy or halo radicals,
R7 and RB, which may be the same or different, each represent hydrogen, alkyl or alkenyl,
R9 represents hydrogen or methyl,
R10 and R", which may be the same or different, each represent hydrogen or alkyl, R12 represents an organic radical having carbon-carbon unsaturation in a position a to the CH2 group to which R12 is attached, indicates an aromatic ring or a dihydro or tetrahydro analogue thereof,
X', X2, X3 and X4, which may be the same or different, each represent hydrogen, chloro or methyl, Z3 represents -CM2- or -0- or -S- or -CO-, D represents hydrogen, cyano or --CECH, Z' and Z2, which may be the same or different, each represent chloro or methyl, and
each n, which may be the same or different, is 0, 1 or 2.
Formula (I) is intended to encompass all the possible geometric and optical isomers. More particularly the acid moiety of the ester may be selected from the (+) - cis - isomer, the (+) trans - isomer, the (I) - cis - isomer, the (j) - trans isomer and the (+) - cis, trans - isomer (the stereochemistry referring to that of the cyclopropane ring), and especially form the dihalo acids such as the dichloro and dibromo acids (in formula (I) R2, R3=CI or Br). The alcohol moiety may especially be chosen from 3 - phenoxybenzyl alcohol and a - cyano - 3 - phenoxybenzyl alcohol. Preferred esters of formula (I) which may be used together include permethrin; decamethrin; (+) - a - cyano - 3 - phenoxybenzyl - (+) - cis, trans 2,2 - dimethyl - 3 - (2,2 - dichlorovinyl)cyclopropane - 1 carboxylate(cypermethrin); and (±) - a - cyano - 3 - phenoxybenzyl - (+) - cis 2,2 - dimethyl - 3 - (2,2 - dibromovinyl)cyclopropane - 1 - carboxylate.
Two or more compounds of formula (I) may therefore be used together to control arthropod pests and especially insects and acarines. Insects and acarines requiring control for agricultural, public health domestic, veterinary and medical purposes include adult and juvenille stages of flies, mites, ticks, cockroaches, mosquitoes, tetse fly, moths including warehouse and clothes moths, fleas, lice and timber and grain infesting insects and dther ectoparasites of mammals and birds.
The compounds may be used to combat arthropod infestations either as a mixture of the raw chemicals (hereafter called the 'compositions') or as a formulation with an inert carrier or diluent. The formulations may be prepared by customary methods as dusts or granular solids, wettable powders, baits, solutions, laquers, creams, pastes, gels, foams, greases, shampoos, ointments, emulsifiable concentrates, sprays, aerosols and other liquid preparations after the addition of appropriate solvents, synergists, diluents and surface active agents. The formulations may contain up to 99 /" by weight of a mixture of compounds of formula (I) and may be diluted prior to use.
Such formulations may be applied directly to arthropod pests or to their environment by dusting, spraying, pouring, fogging, vaporisation, painting, dipping' and other methods customarily used in arthropod control. The amount and concentration of a mixture of compounds of formula (I) which should be applied will vary with the nature of the compounds and formulation, the pests to be controlled, and the habitat and method of application but in general the total concentration should be in the range of 0.0001 to l.0V w/v. In a composition, the compounds of formula (I) should be present in potentiating amounts from 50/1 to 1/50, especially 10/1 to 1/10, parts by weight of the respective compounds.
The following Examples are provided by way of an illustration of the present invention and should not be construed as in any way constituting a limitation thereof.
EXAMPLE 1
Engorged female ticks of the Biarra strain of Boophilus microplus are immersed, in groups of 20 ticks per concentration, in a range of dilutions of (-) a - cyano - 3 - phenoxybenzyl - (+)- cis - 2,2 - dimethyl - 3 - (2,2 dibromovinyl)cyclopropane - 1 - carboxylate (hereafter referred to as decamethrin) in combination with 3 - phenoxybenzyl(+)- cis, trans - 2,2 dimethyl - 3 - (2,2 - dichlorovinyl)cyclopropane - 1 - carboxylate (hereinafter referred to as permethrin) at a ratio of 1/1 w/w of decamethrin and permethrin.
The composite wash is prepared by mixing the two constituents at a ratio of 1:1 and then diluting the mixture with water to give the desired range of concentration for the test. The constituents were in the form of miscible oil concentrates.
The ticks are removed from the wash after 10 minutes, dried, and stuck dorsal side down on double-sided adhesive tape. They remain in this position for 14 days when the numbers laying viable eggs are determined. From this data a regression line is plotted (concentration against V0 inhibition of egg-production) and the IR99 values determined (Table I).
IR99=concentration at which 99Vo inhibition of egg-production occurs.
The values so obtained for the composite wash are compared with similar values obtained for the constituents of the composite wash when alone. By reference to the equation for the harmonic mean, the factor of potentiation is determined (Table I).
The equation for the harmonic mean is:
Proportion of A + Proportion of B X=.
Proportion of A Proportion of B
~ +
IR99A IR99B
X IR99 mixture of A and B YxPronortinn of A
Factor of Potentiation (FOP)=
Proportion of A+Proportion of B
TABLE I
B. microplus Biarra Strain
Factor of
Chemical IR99 ( /n) Potentiation
Permethrin 0.13
Decamethrin 0.0039
Permethrin/Decamethrin (1:1) 0.00032 11.9
Example 2
Wettable Powders
Parts by Weight
(a) (b)
Permethrin 2.5 15.0
Decamethrin 2.5 15.0
Fine silica 5.0 20.0
Kaolin 84.5 44.5
Sodium alkyl naphthalene sulphonate 0.5 0.5
Sodium salt of condensed naphthalene
sulphonic acid 5.0 5.0
100.0 100.0
Example 3
Miscible Oils
Parts by Weight
Permethrin 2.5 12.5
Decamethrin 2.5 12.5
Solvent 200 82.5 57.5
Cyclohexanone - 5.0
Ethylan KEO 8.5 7.5
Tergitol XD 0.7 1.5
Arylan CA 3.3 3.5
100.0 100.0
'Solvent 200' is a liquid comprising 95V aromatic hydrocarbons. 'Ethylan
KEO' (Registered Trade Mark) is an emulsifying agent of a nonyl phenol ethoxylate condensate with ethylene oxide having arl average chain length of 9.5 mols. 'Tergitol XD' (Registered Trade Mark) is a non-ionic liquid emulsifier of a polyalkylene glycol ether. 'Arylan CA' is an emulsifier of calcium dodecyl benzene sulphonate.
Example 4
Dusts
Parts by Weight
Permethrin 0.01 1.0
Decamethrin 0.01 1.0
Talc 99.98 98.0
100.00 100.0
WHAT WE CLAIM IS:
1. A method of controlling arthropod ectoparasites of birds or mammals (other than man) comprising the simultaneous application to the animal or the ectoparasite of two or more esters of formula (I) as hereinbefore defined.
2. A method as claimed in claim 1 wherein two esters of formula (I) are applied.
3. A method as claimed in claim 1 or 2 wherein the esters are applied as a mixture.
4. A method as claimed in claims 2 or 3 wherein the esters are applied in the ratio of 1 to 50 to 50 to 1 parts by weight.
5. A method as claimed in claims 2 or 3 wherein the esters are applied in the ratio of 1 to 10 to 10 to 1 parts by weight.
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (18)
1. A method of controlling arthropod ectoparasites of birds or mammals (other than man) comprising the simultaneous application to the animal or the ectoparasite of two or more esters of formula (I) as hereinbefore defined.
2. A method as claimed in claim 1 wherein two esters of formula (I) are applied.
3. A method as claimed in claim 1 or 2 wherein the esters are applied as a mixture.
4. A method as claimed in claims 2 or 3 wherein the esters are applied in the ratio of 1 to 50 to 50 to 1 parts by weight.
5. A method as claimed in claims 2 or 3 wherein the esters are applied in the ratio of 1 to 10 to 10 to 1 parts by weight.
6. A method as claimed in any foregoing claims wherein in the esters of
formula (I), R2 and R3 are both halo.
7. A method as claimed in claim 6 wherein R2 and R3 are the same and each is selected from chloro and bromo.
8. A method as claimed in any foregoing claim wherein R is selected from 3phenoxybenzyl and a - cyano - 3 - phenoxybenzyl.
9. A method as claimed in any foregoing claim where the esters are selected from: 3 - phenoxybenzyl (+) - cis, trans - 2,2 - dimethyl - 3 - (2,2 - dichlorovinyl)cyclopropane - 1 - carboxylate; (-) - a - cyano - 3 - phenoxybenzyl-(+) - cis - 2,2 - dimethyl - 3 - (2,2 - dibromovinyl)cyclopropane - - carboxylate, (±) - a - cyano - 3 - phenoxybenzyl - (j) - cis, trans - 2,2 - dimethyl - 3 - (2,2 - dichlorovinyl)cyclopropane - 1 - carboxylate; and (+) - a cyano - 3 - phenoxybenzyl - -(+) - cis - 2,2 - dimethyl - 3 - (2,2 dibromovinyl)cyclopropane - 1 - carboxylate.
10. A method as claimed in any of claims I to 9 wherein permethrin and decamethrin are applied.
11. A method as claimed in claim 10 wherein the esters are applied in the ratio of 1 part each by weight.
12. A method as claimed in any foregoing claim wherein the ectoparasites are acarine ectoparasites.
13. A method as claimed in claim 12 wherein the acarine ectoparasites are ticks.
14. A method as claimed in any foregoing claim wherein the esters are applied as a formulation including an inert carrier or diluent.
15. A method as claimed in claim 14 wherein the formulation applied is an aqueous suspension of a wettable powder or an aqueous emulsion of an emulsifiable concentrate.
16. A method as claimed in any foregoing claim wherein the esters are applied by dipping or spraying.
17. A method as claimed in any foregoing claim wherein the esters are applied at a concentration of 0.0001 to 1%.
18. A method for the control of ectoparasites of animals (other than man) substantially as hereinbefore described.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2426578A GB1592229A (en) | 1978-05-30 | 1978-05-30 | Pesticidal formulations |
| DE7979101646T DE2967512D1 (en) | 1978-05-30 | 1979-05-29 | Synergistic pyrethroid formulations and their preparation |
| AU47505/79A AU528416B2 (en) | 1978-05-30 | 1979-05-29 | Pesticidal formulations |
| EP79101646A EP0005826B1 (en) | 1978-05-30 | 1979-05-29 | Synergistic pyrethroid formulations and their preparation |
| NZ190600A NZ190600A (en) | 1978-05-30 | 1979-05-29 | Arthropodicidal compositions containing cyclopropane-carboxylic acid ester derivatives |
| IE1051/79A IE51386B1 (en) | 1978-05-30 | 1979-08-08 | Synergistic pyrethroid formulations and their preparation |
| US06/251,101 US4404223A (en) | 1978-05-30 | 1981-04-06 | Pesticidal formulations |
| MY282/85A MY8500282A (en) | 1978-05-30 | 1985-12-30 | Pesticidal formulations |
| US06/817,786 US4940729A (en) | 1978-05-30 | 1986-01-08 | Pesticidal formulations |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2426578A GB1592229A (en) | 1978-05-30 | 1978-05-30 | Pesticidal formulations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1592229A true GB1592229A (en) | 1981-07-01 |
Family
ID=10209006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2426578A Expired GB1592229A (en) | 1978-05-30 | 1978-05-30 | Pesticidal formulations |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB1592229A (en) |
| MY (1) | MY8500282A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2141201C1 (en) * | 1998-03-16 | 1999-11-20 | Закрытое акционерное общество "Экспериментально-производственный центр "Дезинфекционист" АО "ДДД" | Insecticide composition "ribor-ekstra" |
-
1978
- 1978-05-30 GB GB2426578A patent/GB1592229A/en not_active Expired
-
1985
- 1985-12-30 MY MY282/85A patent/MY8500282A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2141201C1 (en) * | 1998-03-16 | 1999-11-20 | Закрытое акционерное общество "Экспериментально-производственный центр "Дезинфекционист" АО "ДДД" | Insecticide composition "ribor-ekstra" |
Also Published As
| Publication number | Publication date |
|---|---|
| MY8500282A (en) | 1985-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4404223A (en) | Pesticidal formulations | |
| US4564631A (en) | Baits for combating vermin | |
| AU715579B2 (en) | Emulsifiable composition for the control of insects | |
| KR100404645B1 (en) | Emulsifiable Composition for Insect Control | |
| NZ210326A (en) | Pyrethroid-based pesticide composition | |
| JP2861076B2 (en) | Insecticidal aqueous solution | |
| US4020181A (en) | Method of repelling insects from domestic mammals | |
| US3683078A (en) | Transparent toxicant compositions | |
| GB2185685A (en) | An oil-in-water pesticidal emulsion | |
| KR950002852B1 (en) | Insecticide composition for arthropod | |
| US4210642A (en) | Insecticidal and acaricidal compositions | |
| US4362722A (en) | Synergistic tickicidal compositions containing organophosphorus compounds and cyclopropane carboxylates | |
| US4144331A (en) | Synergistic chlorfenvinphos and pyrethroid pesticidal composition | |
| US3462537A (en) | Method for combating mites and ticks | |
| JP2790678B2 (en) | Pest repellent | |
| CA1091148A (en) | Pest control | |
| JP3838661B2 (en) | Emulsifying composition for insect control | |
| GB1592229A (en) | Pesticidal formulations | |
| GB1591105A (en) | Pest control | |
| US4308262A (en) | Pyrethroid pesticidal compositions | |
| US4182772A (en) | Synergistic combinations of amitraz and certain pyrethroids | |
| JPH05255026A (en) | Repellent for blood-sucking insect pest | |
| JP3954649B2 (en) | Emulsifying composition for insect control | |
| GB1602971A (en) | Synergistic pesticidal compositions | |
| JPH08225417A (en) | Aerosol agent for controlling house tick |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |