CA2048543C - Processes and agents for combating fleas - Google Patents
Processes and agents for combating fleasInfo
- Publication number
- CA2048543C CA2048543C CA002048543A CA2048543A CA2048543C CA 2048543 C CA2048543 C CA 2048543C CA 002048543 A CA002048543 A CA 002048543A CA 2048543 A CA2048543 A CA 2048543A CA 2048543 C CA2048543 C CA 2048543C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- halogen
- alkoxy
- hydrogen
- collar according
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- 230000008569 process Effects 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 241001465754 Metazoa Species 0.000 claims abstract description 32
- 238000011161 development Methods 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 44
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical group 0.000 claims description 33
- -1 alkythio Chemical group 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 230000002401 inhibitory effect Effects 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 150000001987 diarylethers Chemical class 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Chemical group 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 239000011737 fluorine Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000002917 insecticide Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000006193 alkinyl group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical group CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 239000004814 polyurethane Substances 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 150000008047 benzoylureas Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 4
- 229960001591 cyfluthrin Drugs 0.000 claims description 4
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical group CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 229930014550 juvenile hormone Natural products 0.000 claims description 4
- 239000002949 juvenile hormone Substances 0.000 claims description 4
- 150000003633 juvenile hormone derivatives Chemical class 0.000 claims description 4
- 229930191400 juvenile hormones Natural products 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 241000894007 species Species 0.000 claims description 4
- 150000003918 triazines Chemical class 0.000 claims description 4
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 229920000193 polymethacrylate Polymers 0.000 claims description 3
- 229920001447 polyvinyl benzene Polymers 0.000 claims description 3
- 229920001291 polyvinyl halide Polymers 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- VBLSYPFUJDGKII-UHFFFAOYSA-N 2-ethenoxyperoxyethanol Chemical group OCCOOOC=C VBLSYPFUJDGKII-UHFFFAOYSA-N 0.000 claims description 2
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 22
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 7
- 239000002344 surface layer Substances 0.000 claims 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 3
- 239000002728 pyrethroid Substances 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- WTGULPIOCRAFHN-UHFFFAOYSA-N COClOC(F)(F)F Chemical group COClOC(F)(F)F WTGULPIOCRAFHN-UHFFFAOYSA-N 0.000 claims 1
- YXWCBRDRVXHABN-JCMHNJIXSA-N [cyano-(4-fluoro-3-phenoxyphenyl)methyl] 3-[(z)-2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical group C=1C=C(F)C(OC=2C=CC=CC=2)=CC=1C(C#N)OC(=O)C1C(C)(C)C1\C=C(/Cl)C1=CC=C(Cl)C=C1 YXWCBRDRVXHABN-JCMHNJIXSA-N 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 abstract description 3
- 241000258242 Siphonaptera Species 0.000 description 28
- 150000002431 hydrogen Chemical group 0.000 description 20
- 235000013601 eggs Nutrition 0.000 description 13
- 229920000915 polyvinyl chloride Polymers 0.000 description 12
- 235000013350 formula milk Nutrition 0.000 description 11
- 241000282326 Felis catus Species 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000004800 polyvinyl chloride Substances 0.000 description 8
- 241000282472 Canis lupus familiaris Species 0.000 description 7
- 239000004014 plasticizer Substances 0.000 description 7
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 6
- 239000005927 Pyriproxyfen Substances 0.000 description 6
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 6
- 235000021355 Stearic acid Nutrition 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
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- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 description 4
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 4
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 4
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- RDOFJDLLWVCMRU-UHFFFAOYSA-N Diisobutyl adipate Chemical compound CC(C)COC(=O)CCCCC(=O)OCC(C)C RDOFJDLLWVCMRU-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
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- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical class C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
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- 238000007598 dipping method Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
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- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 235000020929 long fasting Nutrition 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- 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 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01K—ANIMAL HUSBANDRY; AVICULTURE; APICULTURE; PISCICULTURE; FISHING; REARING OR BREEDING ANIMALS, NOT OTHERWISE PROVIDED FOR; NEW BREEDS OF ANIMALS
- A01K27/00—Leads or collars, e.g. for dogs
- A01K27/007—Leads or collars, e.g. for dogs with insecticide-dispensing means
-
- 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
-
- 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
- A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Animal Husbandry (AREA)
- Biodiversity & Conservation Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Catching Or Destruction (AREA)
- Saccharide Compounds (AREA)
Abstract
The present invention relates to processes and agents for combating fleas on, and in the surroundings of, domestic animals, which is characterised in that the domestic animals are treated with collars which contain active compounds which inhibit insect development.
Description
The present invention relates to processes and agents for combating fleas on, and in the surroundings of, domestic animals, which contain substances which inhibit insect development.
Adult fleas usually live preferably in the coat of their host animals. They feed on the Tatter's blood and lay their eggs in the coat of the particular host animal.
Since the eggs deposited do not adhere to the coat of the host, they fall off rapidly and can therefore be found above all in the surroundings of the host animalva, for example in their beds and bedding.
This means that preferably beds and bedding of the host animals are infested with flea eggs, fram which flea larvae hatch within a few days. Three developmental stages can be distinguished in the larvae, each of which lasts approximately 3 days. The third larval stage spins a cocoon and pupates. Under favourable conditions (20 --30°C, 60 - 80~ relative humidity), the developmewt from the egg to the pupa lasts approximately 10 days. After about ~ more days, development of the fleas is complete, and fleas ~rhich are ready to hatch can be found in the cocoons lying on the floor (carpets, sleeping places etc.). The young flea can remain in its cocoon for months. _ Le A 27 'T49 - 1 -L
Under unfavourable conditions, however, the developmewt from the egg to the adult young flea can last as long as 4 - 5 months. In order to reach sexual maturity, that is to say to lay ferule eggs, fleas require blood as food.
Ideally, this blood is from the particular specific host.
However, particularly after a relatively long fasting period, fleas can also accept the blood of other hosts.
Infestation by fleas of domestic animals such as dogs and cats is not only a nuisance for the 9_nfested animal, but also causes considerable pain (injuries by biting, itching and allergies) and harm (loss of blood) to the infested animals. Fleas can also pass on various species of tapeworm. They therefore also represent a medical problem fox the infested animals and for the animal owners. However, it is also possible for the anima3. owner to be bitten by fleas. In some humans, this causes allergy to flea bites. For this reason, effective control of fleas in dogs and cats has always been desirable and necessary, especially since these domestic animals live 2Q in an increasingly greater number and in increasingly c.~.~Se contact with man.
A large number of insecticidal active compounds has been disclosed to date for combating fleas. Examples of such active compounds are, from the class of the carbamates propoxur, bendiocarb and carbaryl, from the class of the phosphates fenthion and dia~inone, sand from the class of the pyrethroids permethrin, cypermethrin and resmethrin.
:Ge A 27 7~9 - 2 -These active compounds are contact insecticides which act mainly on adult fleas. These active compounds have no effect on eggs or on the pupated stages of the fleas.
The active compounds are used on the host animal, and applied, for example by spraying, douching, washing, as a powder, or by pouring-on or spotting-on. They can also be incorporated into collars. The active compounds are also used in the immediate or further surroundings of the host animals in the form of aerosols, spray formulations ZO and dusts. For this purpose, beds and the home and areas outside the home are treated.
It is also known that insect development inhibitors such as methoprene or cyroma~ine can be added to the agents with which the surroundings of the host anima:~s are treated. This stops the development of adult fleas from eggs and larvae and pupae. However, 'to date it was necessary for the entire surroundings of the host animals, that is to say the entire home of the human, to be treated.
It is also known that reinfestation of dogs and cats by fleas can be prevented by treating dogs and cats orally or parenterally with active compounds which inhibit the growth of fleas (EP-i7S (European Published Specification) 255,803).
It is furthermore known that dogs and cats can be protected against fleas by spraying with an aerosol ~e A 27 7~9 - 3 -~~a formulation containing methoprene. In doing so, it was possible to prevent flea larvae developing from the deposited eggs (International Pest Cowtrol 27, 19~a, pp . l0-.14 ) .
There are also known animal collars which have been impregnated with a solution containing methoprene (EP-OS
(European Published Specification) 124,404).
ell insecticide-based or insect-development-inhibitor-based methods which are known to date for combating fleas in domestic animals involve treatment of the host animal (dog or cat), its bedding or its entire surroundings.
Treatment of the host animals alone is of little promise since for weeks and even months there is the risk o~
reinfestation by freshly hatched fleas from the 1~ surroundings. Treatment of only the bedding Of thE3 host animal is also of little promise since the animals change their beds, and some beds are not even known or (in particular in the case of cats ) are not accessible for treatment.
The greatest success can therefore be achieved when the host animals as well as their entire surroundings are treated. Treatment of the surroundings is labour-intensi.ve and xequires plenty of material. Possibilities should therefore be sought which reduce the amount of labraur and the material emplayed for the treatment.
This is made possible by the present invention.
Le .A. 27_ 749 - 4 -Tt has been found that fleas on, and in the surroundings of, domestic animals can be combated by treating the domestic animals with collars which contain insect-development inhibitors.
New animal collars have been found which contain insect-development inhibitors. a~n exception are collars based on absorptive material which has been impregnated with methoprene.
In this way, the treated animals provide, simultaneously with the distribution of the flea eggs, for a targeted distribution of the active compound to those locations from which a reinfestation with fleas may occur. Hence, the animals themselves provide the targeted distribution of the active compaund. In this way, neither are locations left out which must be treated, nor is active compound wasted in locations in which the host animal does not stay. Moreover, the labour in connection with the application of the active compound is dispensed with.
It was surprising that an effect could be achieved by a0 this way of applying the active compound. In the methods known to date, the eggs or larvae in the surroundings were treated directly or came into contact with the active compound on the an9.mals when the latter were treated.
However, it could not have been expected that efficient control of fleas in the surroundings is possible by the Le A 27 749 - 5 -treatment according to the invention.
The success of the treatment can even be increased by adding, to the collars, an insecticide which is active against fleas (adulticide) for combat:Lng the adult fleas.
Domestic animals which may be mentioned are dogs and cats. The following may be mentioned as fleas: Ctenocep halides spec., Pulx spec., Xenopsylla spec., Ceratophyllus spec., ~chidnophaga spec., Tunga spec..
The following may be mentioned as active compounds which have an insect-development-inhibiting action: juvenile hormones or juvenile-hormone-type substances, substituted diaryl ethers, benzoylureas and triazine derivatives.
These compounds are known. The juvenile hormones and juvenile-hormone-type substances include, in particular, compounds of the following formulaes Le A 27 7~g ° 6 -.~C~HS
v C2H5 CH3 -' ~ ~ i '°°'° ~ -O C H ~
~ CHI CH3 i so--H~C3 w.
CHO i H3 I H3 ~~
H3C C\
~CH
C H 3 0--w o a 0 HSC~~ ! C2H5 ~'H3 0 v H~.C OCH~
H3C_ 0 CH3 CH3 II
a HOC OCH~
Le A 27 749 ° '1 The substituted diaryl ethers include, in particular, substituted alkoxydiphenyl ethers or -diphenylmethanes of the general formula T
R1 r- c c~ y- c cH y-a;-H~ c, R~
where R1 represents hydrogen, halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthia, dioxyalkylene, dioxyhalogeno-alkylene, CN, I~C2, alkenyl, alkinyl, alkaxyalkyl, 1p alkoxyalkoxy or hydroxyalkoxy, RZ represents the radicals mentioned under R1, R3 represents the radicals mentioned under R1, R4 represents hydrogen, alkyl, halogenoalkyl or halogen, RS represents the radicals mentioned under R4, ~Iet represents optionally subst~.~tuted heteroaryl which is not banded to the remaining radical via the heteroatom, ~ and Y independently of one another represent -0- or -S-, Z represents -0-, -S-, -CHfz-, -CHCH3-, -C(CI33)z-, m and n independently of one another represent 0, 1, 2 or ~, but their total is equal to, or greater than, ~.
Preferred compounds of the formula T are those in which R1 represents hydrogen, fluorine, chlorine, bromine, Cl_4-alkyl, C1_~,-alkoxy, Cl_4-alkylthio, Cl_4-halo-genoalkyl having up to 5 halogen atoms, in particular trichloromethyl, ~trifluoroanethyl, C~_~--halogenoalkoxy having up to 5 halogen atoms, in particular trichloromethoxy, trifluoromethoxy, C~_4-halogenoalkylthio having up to 4 halogen atoms, in particular trifluoromethylthio, CN, X102, CZ_3-alkenyl, C1_~,-alkoxy-C1_2-alkyl, in particular ethoxymethyl, methoxyethyl, C~_z-alkoxy-Cl_g-alkoxy, in particular methoxyethoxy, C1_4-~hydroxyalkoxy, in particular hydroxyethoxy, dioxyethylene, dioxymethylene, difluorodioxymethylene, trifluorodioxyethylene or dichlorooxymethylene, RZ represents the radicals mentioned under R1, R3 represents the radicals mentioned under R', R~ represents hydrogen, Cl_,,-alkyl, C1_4-halogenoalkyl having up to 5 halogen atoms, chlorine, fluorine or bromine, 7Le A ~7 74~
Ft5 represents the radicals mentioned under R, Het represents pyridyl, pyridazinyl, pyrimidinyl, or pyra~inyl, each of which is aptionally sub-stituted by one ar mare identical or different radicals Pram the group comprising C1_~-alkyl, such as methyl, ethyl, t-butyl, halogen, such as fluorine, chlorine, bromine, IdOa, C1_$-alkoa~y, C1_4-alkylthio, Ci_~-alkoxy, Cl_4-alkyl~thio, C1,4-halagenoalkyl having up to 5 halogen atoms, C1_4-halogenaalkoxy having up to ~ halogen stems ar C1_~-halogenaalkylthia having up to a halagen atoms, X and Y independently of one another represent -t7- or -S-r ~ represents -0-, -~-, -CH2-, -CHCH3-, -C ( CI~3 ) a-, m represents 1 ox' 2, and n represents 1 or 2a Particularly preferred campaunds of 'the formula I are these in which represents hydrogen, methyl, trifluaramethyl, me~thax~r, trifluoromethaxy, chlorine ar fluorine, represents hydrogen, R~ represents hydrogen, fluorine, chlorine or methyl, R4 represents hydrogen or methyl, RS represents methyl, ethyl, trifluoromethyl or hydrogen, Het represents pyridyl or pyrids~iny.l, each of which is optionally substituted by fluorine, chlorine, methyl, ~TOz, metl~ao~cyor methylmercapto 0 X represewts O, Y represents 0, represents 0, CHz or 'C ( CH3 ) z', m represents 1 n represents 1 The following comgounds be mentioned lndlVldllt''Allys may R1 ~ J R6 ~ ' Ck3~ - CH' Cr' N
R
H H CHI ~-C1 0 H H CHI H C(CI9~)2 Z \_..-/ I R6 R3 o-CHZ-CH-a--(~~~
N
Ri Ft3 R5 R6 ~
Z(CH2)~-0-Hei, ~R1 ~R--~3 F3~ ~d~ Z H~i H H p N
H H O
N
H H O "°
N--N
Le .Pb 2 7 7 4 9_ ° ~. ~ -°
The substituted diaryl ethers also include the compounds of the formula zz R1 ~ ~ ~ ~ Y-(CH)m-(CH)n~Z-13~t X~ 6 O
R
where ~ represents 0, S, NH, -CH2-, -CHCH3~, -C ( CH3 ) ~-, Y represents ~ or S, represents 0 or S, R1 represents identical or different radicals from the group comprising hydrogen, halogen, alkyl, Zp alkoxy or halogenoalkyl, R2 represents identical ar different radicals from the group comprising hydrogen, halogen, alkyl, alkenyl, halagenoalkyl, alkoxy, alkylthio, halogenaalkoxy or halogenoalkylthio, R3 represents hydrogen, alkyl, halogenoalkyl, alkoxyalkyl, alkenoxyalkyl, alkenyl or alkinyl, R" represents the radicals mentioned under R3, R3 and R4 together with the adjacent C atoms can represent saturated or unsaturated 5- to 7-membered carbocyclic rings, m represents 1 or 2, n represents 1 or 2, o represents 1, ~ or 3 and Het represents optionally substituted heteroaryl which is not bonded to the remaining radical ~a.a the heteroatom.
The following may be mewtioned in par~t.~cular~
Zo(-~t-7C~-Het b ~~ 3 X
H2 s H2 ~ Hit ~2H5 -CHI°CH°
Q. 1.3 ~C1~
i ~' 3 5 H °CH~-CH
s H~t 0 1,3-012 -CHZ-iH-CHZF
0 1.3-012 CHZ iH
i CHZ-F
S 1.3-012 -CHZ'iH- ~
CHZ-F
v 0 3-F5r -CHZ- i H-CHZ-F
CHZ 1.3-012 -CHZ-iH-CHZF
CHZ H -CHZ-iH-CHZ-F
0 H -CHZ-jH- \ y CHZF
S H -CHZ-iH-CHZF
~~~~~c~~9 X Rz H Hit 0 1.3-cy -cH~-cH- ~ I
'''~.r''~"'c x cH~~
I H 3 ~-~c H 3 - ~~N 0 0 1a3-C1~ -CHZ-CH
/ \ N
1 3_C1 -CH -CH- N_~,.N ~'~
IH3 ~CH3 - w~N 0 CHI 1.3-C12 -CH2-CH H
~
-CH- / \ N
0 H -C IJ~N ~"C
Z
0 1.3-012 -CH2CH~0- CH2-CH~-I~ 1 X~Y(-H-)-0-Hit X Y H Het 0 S -CH2GH~OCH~CH~ ~~~ I
I e~
CHZ-F
S o -cH~-cH- r I
cH~-F
r 0 O °CHy CH-I w CfI2-F
r I w CHI-F
0 p -CH2-CH-w 7Le i~. 2 7 7 4 9 ° ~.7 0~5 ~C Y a H~ ~
CHI
N-CH
AN
~
CHI
~--N~O
O 0 - CH 2 CH , - N----N ~--( I . CH3 CHZF
~ ~CI~~
~~
---N N-CH
I NN ~--J 'C 1-I ~
CHEF
CHI
CH 0 -CH -~~
-CH- ~--N~
Adult fleas usually live preferably in the coat of their host animals. They feed on the Tatter's blood and lay their eggs in the coat of the particular host animal.
Since the eggs deposited do not adhere to the coat of the host, they fall off rapidly and can therefore be found above all in the surroundings of the host animalva, for example in their beds and bedding.
This means that preferably beds and bedding of the host animals are infested with flea eggs, fram which flea larvae hatch within a few days. Three developmental stages can be distinguished in the larvae, each of which lasts approximately 3 days. The third larval stage spins a cocoon and pupates. Under favourable conditions (20 --30°C, 60 - 80~ relative humidity), the developmewt from the egg to the pupa lasts approximately 10 days. After about ~ more days, development of the fleas is complete, and fleas ~rhich are ready to hatch can be found in the cocoons lying on the floor (carpets, sleeping places etc.). The young flea can remain in its cocoon for months. _ Le A 27 'T49 - 1 -L
Under unfavourable conditions, however, the developmewt from the egg to the adult young flea can last as long as 4 - 5 months. In order to reach sexual maturity, that is to say to lay ferule eggs, fleas require blood as food.
Ideally, this blood is from the particular specific host.
However, particularly after a relatively long fasting period, fleas can also accept the blood of other hosts.
Infestation by fleas of domestic animals such as dogs and cats is not only a nuisance for the 9_nfested animal, but also causes considerable pain (injuries by biting, itching and allergies) and harm (loss of blood) to the infested animals. Fleas can also pass on various species of tapeworm. They therefore also represent a medical problem fox the infested animals and for the animal owners. However, it is also possible for the anima3. owner to be bitten by fleas. In some humans, this causes allergy to flea bites. For this reason, effective control of fleas in dogs and cats has always been desirable and necessary, especially since these domestic animals live 2Q in an increasingly greater number and in increasingly c.~.~Se contact with man.
A large number of insecticidal active compounds has been disclosed to date for combating fleas. Examples of such active compounds are, from the class of the carbamates propoxur, bendiocarb and carbaryl, from the class of the phosphates fenthion and dia~inone, sand from the class of the pyrethroids permethrin, cypermethrin and resmethrin.
:Ge A 27 7~9 - 2 -These active compounds are contact insecticides which act mainly on adult fleas. These active compounds have no effect on eggs or on the pupated stages of the fleas.
The active compounds are used on the host animal, and applied, for example by spraying, douching, washing, as a powder, or by pouring-on or spotting-on. They can also be incorporated into collars. The active compounds are also used in the immediate or further surroundings of the host animals in the form of aerosols, spray formulations ZO and dusts. For this purpose, beds and the home and areas outside the home are treated.
It is also known that insect development inhibitors such as methoprene or cyroma~ine can be added to the agents with which the surroundings of the host anima:~s are treated. This stops the development of adult fleas from eggs and larvae and pupae. However, 'to date it was necessary for the entire surroundings of the host animals, that is to say the entire home of the human, to be treated.
It is also known that reinfestation of dogs and cats by fleas can be prevented by treating dogs and cats orally or parenterally with active compounds which inhibit the growth of fleas (EP-i7S (European Published Specification) 255,803).
It is furthermore known that dogs and cats can be protected against fleas by spraying with an aerosol ~e A 27 7~9 - 3 -~~a formulation containing methoprene. In doing so, it was possible to prevent flea larvae developing from the deposited eggs (International Pest Cowtrol 27, 19~a, pp . l0-.14 ) .
There are also known animal collars which have been impregnated with a solution containing methoprene (EP-OS
(European Published Specification) 124,404).
ell insecticide-based or insect-development-inhibitor-based methods which are known to date for combating fleas in domestic animals involve treatment of the host animal (dog or cat), its bedding or its entire surroundings.
Treatment of the host animals alone is of little promise since for weeks and even months there is the risk o~
reinfestation by freshly hatched fleas from the 1~ surroundings. Treatment of only the bedding Of thE3 host animal is also of little promise since the animals change their beds, and some beds are not even known or (in particular in the case of cats ) are not accessible for treatment.
The greatest success can therefore be achieved when the host animals as well as their entire surroundings are treated. Treatment of the surroundings is labour-intensi.ve and xequires plenty of material. Possibilities should therefore be sought which reduce the amount of labraur and the material emplayed for the treatment.
This is made possible by the present invention.
Le .A. 27_ 749 - 4 -Tt has been found that fleas on, and in the surroundings of, domestic animals can be combated by treating the domestic animals with collars which contain insect-development inhibitors.
New animal collars have been found which contain insect-development inhibitors. a~n exception are collars based on absorptive material which has been impregnated with methoprene.
In this way, the treated animals provide, simultaneously with the distribution of the flea eggs, for a targeted distribution of the active compound to those locations from which a reinfestation with fleas may occur. Hence, the animals themselves provide the targeted distribution of the active compaund. In this way, neither are locations left out which must be treated, nor is active compound wasted in locations in which the host animal does not stay. Moreover, the labour in connection with the application of the active compound is dispensed with.
It was surprising that an effect could be achieved by a0 this way of applying the active compound. In the methods known to date, the eggs or larvae in the surroundings were treated directly or came into contact with the active compound on the an9.mals when the latter were treated.
However, it could not have been expected that efficient control of fleas in the surroundings is possible by the Le A 27 749 - 5 -treatment according to the invention.
The success of the treatment can even be increased by adding, to the collars, an insecticide which is active against fleas (adulticide) for combat:Lng the adult fleas.
Domestic animals which may be mentioned are dogs and cats. The following may be mentioned as fleas: Ctenocep halides spec., Pulx spec., Xenopsylla spec., Ceratophyllus spec., ~chidnophaga spec., Tunga spec..
The following may be mentioned as active compounds which have an insect-development-inhibiting action: juvenile hormones or juvenile-hormone-type substances, substituted diaryl ethers, benzoylureas and triazine derivatives.
These compounds are known. The juvenile hormones and juvenile-hormone-type substances include, in particular, compounds of the following formulaes Le A 27 7~g ° 6 -.~C~HS
v C2H5 CH3 -' ~ ~ i '°°'° ~ -O C H ~
~ CHI CH3 i so--H~C3 w.
CHO i H3 I H3 ~~
H3C C\
~CH
C H 3 0--w o a 0 HSC~~ ! C2H5 ~'H3 0 v H~.C OCH~
H3C_ 0 CH3 CH3 II
a HOC OCH~
Le A 27 749 ° '1 The substituted diaryl ethers include, in particular, substituted alkoxydiphenyl ethers or -diphenylmethanes of the general formula T
R1 r- c c~ y- c cH y-a;-H~ c, R~
where R1 represents hydrogen, halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthia, dioxyalkylene, dioxyhalogeno-alkylene, CN, I~C2, alkenyl, alkinyl, alkaxyalkyl, 1p alkoxyalkoxy or hydroxyalkoxy, RZ represents the radicals mentioned under R1, R3 represents the radicals mentioned under R1, R4 represents hydrogen, alkyl, halogenoalkyl or halogen, RS represents the radicals mentioned under R4, ~Iet represents optionally subst~.~tuted heteroaryl which is not banded to the remaining radical via the heteroatom, ~ and Y independently of one another represent -0- or -S-, Z represents -0-, -S-, -CHfz-, -CHCH3-, -C(CI33)z-, m and n independently of one another represent 0, 1, 2 or ~, but their total is equal to, or greater than, ~.
Preferred compounds of the formula T are those in which R1 represents hydrogen, fluorine, chlorine, bromine, Cl_4-alkyl, C1_~,-alkoxy, Cl_4-alkylthio, Cl_4-halo-genoalkyl having up to 5 halogen atoms, in particular trichloromethyl, ~trifluoroanethyl, C~_~--halogenoalkoxy having up to 5 halogen atoms, in particular trichloromethoxy, trifluoromethoxy, C~_4-halogenoalkylthio having up to 4 halogen atoms, in particular trifluoromethylthio, CN, X102, CZ_3-alkenyl, C1_~,-alkoxy-C1_2-alkyl, in particular ethoxymethyl, methoxyethyl, C~_z-alkoxy-Cl_g-alkoxy, in particular methoxyethoxy, C1_4-~hydroxyalkoxy, in particular hydroxyethoxy, dioxyethylene, dioxymethylene, difluorodioxymethylene, trifluorodioxyethylene or dichlorooxymethylene, RZ represents the radicals mentioned under R1, R3 represents the radicals mentioned under R', R~ represents hydrogen, Cl_,,-alkyl, C1_4-halogenoalkyl having up to 5 halogen atoms, chlorine, fluorine or bromine, 7Le A ~7 74~
Ft5 represents the radicals mentioned under R, Het represents pyridyl, pyridazinyl, pyrimidinyl, or pyra~inyl, each of which is aptionally sub-stituted by one ar mare identical or different radicals Pram the group comprising C1_~-alkyl, such as methyl, ethyl, t-butyl, halogen, such as fluorine, chlorine, bromine, IdOa, C1_$-alkoa~y, C1_4-alkylthio, Ci_~-alkoxy, Cl_4-alkyl~thio, C1,4-halagenoalkyl having up to 5 halogen atoms, C1_4-halogenaalkoxy having up to ~ halogen stems ar C1_~-halogenaalkylthia having up to a halagen atoms, X and Y independently of one another represent -t7- or -S-r ~ represents -0-, -~-, -CH2-, -CHCH3-, -C ( CI~3 ) a-, m represents 1 ox' 2, and n represents 1 or 2a Particularly preferred campaunds of 'the formula I are these in which represents hydrogen, methyl, trifluaramethyl, me~thax~r, trifluoromethaxy, chlorine ar fluorine, represents hydrogen, R~ represents hydrogen, fluorine, chlorine or methyl, R4 represents hydrogen or methyl, RS represents methyl, ethyl, trifluoromethyl or hydrogen, Het represents pyridyl or pyrids~iny.l, each of which is optionally substituted by fluorine, chlorine, methyl, ~TOz, metl~ao~cyor methylmercapto 0 X represewts O, Y represents 0, represents 0, CHz or 'C ( CH3 ) z', m represents 1 n represents 1 The following comgounds be mentioned lndlVldllt''Allys may R1 ~ J R6 ~ ' Ck3~ - CH' Cr' N
R
H H CHI ~-C1 0 H H CHI H C(CI9~)2 Z \_..-/ I R6 R3 o-CHZ-CH-a--(~~~
N
Ri Ft3 R5 R6 ~
Z(CH2)~-0-Hei, ~R1 ~R--~3 F3~ ~d~ Z H~i H H p N
H H O
N
H H O "°
N--N
Le .Pb 2 7 7 4 9_ ° ~. ~ -°
The substituted diaryl ethers also include the compounds of the formula zz R1 ~ ~ ~ ~ Y-(CH)m-(CH)n~Z-13~t X~ 6 O
R
where ~ represents 0, S, NH, -CH2-, -CHCH3~, -C ( CH3 ) ~-, Y represents ~ or S, represents 0 or S, R1 represents identical or different radicals from the group comprising hydrogen, halogen, alkyl, Zp alkoxy or halogenoalkyl, R2 represents identical ar different radicals from the group comprising hydrogen, halogen, alkyl, alkenyl, halagenoalkyl, alkoxy, alkylthio, halogenaalkoxy or halogenoalkylthio, R3 represents hydrogen, alkyl, halogenoalkyl, alkoxyalkyl, alkenoxyalkyl, alkenyl or alkinyl, R" represents the radicals mentioned under R3, R3 and R4 together with the adjacent C atoms can represent saturated or unsaturated 5- to 7-membered carbocyclic rings, m represents 1 or 2, n represents 1 or 2, o represents 1, ~ or 3 and Het represents optionally substituted heteroaryl which is not bonded to the remaining radical ~a.a the heteroatom.
The following may be mewtioned in par~t.~cular~
Zo(-~t-7C~-Het b ~~ 3 X
H2 s H2 ~ Hit ~2H5 -CHI°CH°
Q. 1.3 ~C1~
i ~' 3 5 H °CH~-CH
s H~t 0 1,3-012 -CHZ-iH-CHZF
0 1.3-012 CHZ iH
i CHZ-F
S 1.3-012 -CHZ'iH- ~
CHZ-F
v 0 3-F5r -CHZ- i H-CHZ-F
CHZ 1.3-012 -CHZ-iH-CHZF
CHZ H -CHZ-iH-CHZ-F
0 H -CHZ-jH- \ y CHZF
S H -CHZ-iH-CHZF
~~~~~c~~9 X Rz H Hit 0 1.3-cy -cH~-cH- ~ I
'''~.r''~"'c x cH~~
I H 3 ~-~c H 3 - ~~N 0 0 1a3-C1~ -CHZ-CH
/ \ N
1 3_C1 -CH -CH- N_~,.N ~'~
IH3 ~CH3 - w~N 0 CHI 1.3-C12 -CH2-CH H
~
-CH- / \ N
0 H -C IJ~N ~"C
Z
0 1.3-012 -CH2CH~0- CH2-CH~-I~ 1 X~Y(-H-)-0-Hit X Y H Het 0 S -CH2GH~OCH~CH~ ~~~ I
I e~
CHZ-F
S o -cH~-cH- r I
cH~-F
r 0 O °CHy CH-I w CfI2-F
r I w CHI-F
0 p -CH2-CH-w 7Le i~. 2 7 7 4 9 ° ~.7 0~5 ~C Y a H~ ~
CHI
N-CH
AN
~
CHI
~--N~O
O 0 - CH 2 CH , - N----N ~--( I . CH3 CHZF
~ ~CI~~
~~
---N N-CH
I NN ~--J 'C 1-I ~
CHEF
CHI
CH 0 -CH -~~
-CH- ~--N~
2 I , ~---N
N
o O -cH~-cH---~~~---N o i N.---N ~
CHI
0 O _CFI~_CH_ ,~-N O
I N~N
ccz~ cH~
r~
S 0 -CHI-CHw -~~---N
O
I N~N ~
CC1~
~e A 27 749 - lg -The substituted diaryl ethers furthermore include the compounds of the formula (III) R~ R4 R1 s ~ ~ ~. _CHs ,,.CH_ ~ ~5 X 2 ~ Y ° (ITI) F~
where x represents 0, S, D1H, -CHI-, --CHCH3-, -~ ( CH3 ) 2-Y represents straight-chain or branched alkylene which is optionally interrupted by oxygen, R1 represents identical or different radica7.s from the group comprising hydrogen, halogen, alkyl, alkaxy and halogenaalkyl, R2 represents identical ax different radica~.s from the group comprising hydrogen, halogen, alkyl, alkenyl, halagenoalkyl, alkoxy, alkylthio, halogenoalko~cy and halogenoalkylthia, R3 represents hydrogen, alkyl, halagenaalkyl, alkaxyalkyl, alkenaxyalkyl, alkenyl ar alkinyl, R" repxesents the radicals mentioned under R~, R3 and R~ tagethes can represent a direct bond, an~cl Le ~4 27 749 - 19 -v~5 RS repre~ent~ hydrogen, halogen, alkyl, halogeno-alkyl, al3soxy, amino, alkyl, alkylamino, dialkyld amino ox acylamino.
The following array ~e mentioned in particulars _ ~~ ~\
~ z Ct ~"
~--- 5 0 1.3 C1~ -CH2-CHZ-0-CH~-CH- 3-NH2 iH3 S H -CHICH-0-CHZ-CH- 5-N~a o. 1.3-C1~ -CH2-CHZ-0-CH~CH~- 4-NF-l~
p 1.3-C12 -CH2-CH~-0-CH~CHZ- 3-oCH3 S 1.3-Clz -CHI-CHI-C3-CHZCH~- S-OCH3 Q 3-8r -CHI-CH~-0-CH~CP4~- S-OCH3 CH2 1.3-C1~ -CHI-CHZ-0-CH~CH2-0-CH~CH~-CH2 H -CHI-CHI-O-CH2-CH 5-C~"3 0 H -CH2-~H-0-CHZ-iH- 5N~
S H CH~-iHO-CH~-CH2- 5-NON-CH3 0 1.3-C1~ -CHZ-CHZ-0-CH2CH2-3-NH-C-NH f~_\ ~~\
~I
!H3 ~CH3 0 1.3-C12 -CHZ-CH-0-CH2CH2- 5-~N~O
~....~
S 1.3-C1~ -CHI-CH-0-CHZ-rH2-5-N~
Le A 2? ?49 - 21 -X F~'~ a R 5 iH3 ,~CH3 CHI 1.3-C1~ -CHI-CH-0-CH~CH~° 5-N~0 O H -CHI°CHZ-0-CH2CH2° 5°N~O
O 1.3°C1~ --CHZCI-1~0-CHZ°CH~- 3°NH-C-NH ~
ii -CH- H -CH2CH~°O°CNZCH~° 4°OCH3 i i O H 3°NH°C-NH ~
0 H -CH2CHZ°0°CHZCH2CH2° 4°NH°C-NH' F3 i ~l 7~~ A 27 7~9 - 22 -The diaryl ethers furthermore include the compounds of the formula (IV) Het-X
o cp n c;-cH~~ ~-Z (xV~
~s in which Het represents an optionally sulastituted hetero-aromatic radical represents O, S, -CHZ°, °O-CH2-, -''a-~I~Ig~-, -C:HZ-O-O
I I
_C°D _C_ N-O-C1-~4-alkyl , Y represents O, -0-CHZ-, S, Z represents an optianally substituted aromatic or heteroaromatic radical;
m represents integers from 1 to ~&, n represents 0, 1, 2, 3 or 4, o represents 0, 1, 2, 3 or ~, where n and o must not simultaneously represent 0, Le A 27 749 - 23 °
p represents integers from 1 to 4, R2, R3, R~, 'R5, R6 independently of one another represent hydrogen, C1-C6-alkyl, which is optionally sub-stituted by halogen or C1_4-alko~cy; two radicals which axe adjacent to each other can also, together with the C atoms to which they are bonded, form a saturated carbocyclic 5- or 6-ring, and R1 represents identical or different radicals from the group comprising hydrogen, halogen, CN, C1_4-alkyl, 1-5-halogeno-C1_~-alkyl, C1_4-alkoxy, C1_4-alkylthio, 1-5-halogeno-C1_~-al3coacy, 1-5-halogeno--C1_4-alkylthio, phenyl or phenoxy.
The following may be mentioned in particulars x ~'~r-o ( -a d D o-sae ~.
~°N X ~ ~' ~1 a x R 1 B ~I ~t t j~~s o a . a-cy -c~az-c~-Le A z~ ~~~ - z4 -X R1 ~ Hit CF"3 H -CHI-CH I
0 1.3-C1~ -CH2-CH- r I
I h~
CHEF
0 1.3C1~ -CHZ-CH I
I std CHZ-F' S 1.3-C12 _CH2-CH- r I
I
CHZ-~' CHZ 1.3-C12 _CH~-CH- r I
I h~
CH2_F
CH2 H -CH2-CH- r I
I .~-'N
CH2_F
0 H CH~-CH-~t~P
CHEF' S H -CHI-CH- r I
~N
CH~~"
T~e da 2"7 a~9 - 25 -H1 ~ Het 0 1.3-C1~ -CHI-CH-CHEF
iH3 ~CH3 0 1 -CH ! ~ N
3-Cl -CH-. 2 0 Z
H3 /~'~CH3 S 1 -CH ~~~~ --3J 0 . 2 p,~'~"T~ ~.--~
CH2 1.3-C1~ _CH~-CH_ ! ~ N
H
0 H -CH ! ~ IJ~O
-CH-C;H3 ~H3 I
0 1.3-C12 -CHaGH~O-CHI-CH~- v Le A 27 749 - 2~ --~ n ~i 1 xYC-B-)-o-Hat X Y B Het r O S -CH2CH20CH~CH~
°
0 0 CH2-CHZ-0-CH~-CHI
s 0 S -CHI-iH-S 0 -CH2-iH-CHI-F
0 0 -CH2-CH- °
CHc -~' CH~_F
ri Le A 27 749 - ~7 ~-X Y ~~ Het I H --~~---N~N-cH ~
0 O -CHI-CH- N-°'N
CHI
~~---_N'~o O o -CHZ-CH- N-N
cH3 cH~F
/CHI
S O - CH ~ - C i - --~-~N~N--CH
N...aN \C H 3 CHEF
CHI
Ck.p~ O °CH~-CH- '.~N O
I N--mN \"'°"~
CFA CHI
O O -CH2 CH ~~~N~,O
I N°'-N
O O _C~I~_CH- -'-~N O
N-N
CC;I ~ CHI
o - CH z _ c ~ _ --,~~---.NCO
N-°-N
CCl~
La A 27 7~9 - 28 -The benzoylureas inolude compounds of the formula (V):
R~ V
~ ~-NH-coNH( ) '°~R4 RZ
where R1 represents halogen, Rz represents hydrogen or halogen, R3 represents hydrogen, halogen or C1_4-alkyl, R4 represents halogen, 1-5-halogeno-C1_4-alkyl, Cl_4-alko~cy, 1-5-halogeno-C1_4-alkoxy, Cl_4-alkyl-thin, 1-5-halogens-C1_~,-alkylthio, pheno:Ky or ltd pyridyloxy, each of whioh aan be optionally substituted by halogen, C1_m-alkyl, 1-5-halogeno-Cl_4-alkyl, C1_4-alkoary, 1-5-halogeno-Cl_4--alkoxy, C1_4-alkylthio, or 1-5-halogeno-C1-C4-alkylthio.
The following may be mentioned in particular:
R~
ONHCONH ° ~ ~ R'~
- ~e :~ 27 749 - 29 -F F CFS
F F SCFS
H F OCFS
F F 0 ~~~ C1 F F 0 ~~~ CF3 F F 0 ~~.~ CF3 the ~triazines include compounds of the formula (VT) N, IN (VI) .
wheria he A ~7 74~ m 30 -~~~
R1 represents cyclopropyl or isopropyl;
Rz represents hydrogen, halogen, C1-Clz--alkyl-carbonyl, cyclopropylcarbonyl, Cz-Clz-alkl-carbamoyl, C~-Clz-alkylthiocarbamoyl or Cz-C6-alkenylcarbamoyl; and R3 represents hydrogen, C1-C~z-alkyl, cyclopropyl, Cz-Cs-alkenyl, C1-Ciz-alkylcarbonyl, cyclopropyl-carbonyl, C1-Clz-alkylcarbamoyl, C1-Clz-alkylthio-carbamoyl or Cz-C6-alkenylcarbamoyl, and their acid addition salts which are non-toxic to warm-blooded species.
The following may be mentioned in particularo Cyclopropyi H H
Cyclopropyi H CHI
Cyclopropyl H CZHS
Cyclapropyl H C~H7-n Cyc 1 opropyl H C,~Hc~-n Cyclopropyl H CSHqq-n Cyclopropyl H C6Hq~-n Cyclopropyl H C~HqS-n Cyclopropyl H C~H1?-n ~e A 27 749 - 31 -( con-tinua~ion) Cyclopropyl H C12H25 n Cyclopropyl H CH2-CgH9-t Cyclopropyl H CH2CH(CH3)C2H5 Cyelopropyl H CH2CH-CH2 Cyclopropyl C1 Cyclopropyl C1 C6H13-n Cyclopropyl C1 C8H1~.-n Cyclopropyl C1 C12H25"n Cyclopropyl H Cyclopropyl Cyclopropyl H COCH3 Cyclopropyl H COCH3'HC1 Cyeloprapyl H C0C2H5'HC1 Cyclopropyl H COC2H5 Cyclopropyl H COC3H~-n Cyclopropyl H COC3Hp-i Cyclopropyl H COC4H9-tHCl Cyclopropyl H COCaH9-n Cyclopropyl H
COC~H13-n Cyclopropyl H COC11-H23-n Cyclopropyl COCH3 COC2H5 Cyclopropyl COC3H~-n COC6H13-n Cyclopropyl COCH3 COC3H~-n Cyclopropyl COC2H5 COC3H'-n Cyclopropyl H COCyclopropyl Cyclopropyl COCylclopropyl COCyclopropyl Cycloprapyl COCH3 COCH3 T~opropyl H H
Le A 27 749 ~ 32 (continuation) H1 R2 ~3 Isopropyl H COCHC
Isopropyl H COC~H~-n Cyclopropyl H CONHCH3 Cyclopropyl H C0NHC3H7-i Cyclopropyl CONHCH~ CONHCH~
Cyclopropyl H CSNHCH3 Cyclopropyl H CONHCH~CH=CHI
Cyclopropyl CONHCHZCH=CHZ CONHCHZCH=CHz Cyeloprapyl CSNHCH~ CSNHCH3 The abovementioned substituted diaxyl ethers of the formula I must be particularly emphasised.
Insecticides which may be incorporated into the collars according to the invention in addition to the development inhibitors mentioned axe: phosphates, such as, for example, fenthion, caxbamates such as, fox example, propoxux, pyrethxoids such as, fox example, cyfluthrin ox flumethxin.
1Q Substances which can be used for producing the collars according to the invention axe polyvinyl resins, poly-urethanes, polyacrylates, epoxy resins, cellulose, cellulose derivatives, polyamides and polyesters which axe suff~.ciewtly compatible with th~ abovementioned active compounds. The polymers must have suffic:Lently Le A 27 749 - 33 -high strength and flexibility so as not to crac3c or became brittle when formed into a collar. They must be sufficiently durable so as to be resistant to normal wear and tear. Moreover, the polymers must permit sufficient migration of the active compounds to the surface of the moulding. These properties are met, in particular, by solid polyvinyl resins, that is to say po:Lymers which are formed by polymers of a vinyl double bond.
Examples of typical vinyl resins are polyvinyl halides, such as polyvinyl chloride, polyvinyl chloride/vinyl acetate and polyvinyl fluoride; polyacrylate esters and polymethacrylate esters such as polymethyl acrylate and polymethyl methacrylate; and polyvinylbenzenes such as polystyrene and palyvinyltoluene.
Z5 Suitable plasticisers for the production of the collars according to the invention on the basis of polyvinyl resin are those which are customarily used for plastic-ising solid vinyl resins. The plasticiser to be used depends on the resin and .its compatibility with the 2~J plasticiser. Examples of suitable plasticisers are esters of phosphoric acid, such as tricresyl phosphate, esters of phthalic acid, such as dimethyl phthalate and dioctyl phthalate, and esters of adipic acid, such as diisobutyl adipate. It is also possible to use other esters, s7,ach as 25 the esters of azelaic acid, malefic acid, ric:inoleic acid, myristic acid, palmitic acid, oleic acid, sebacic acid, stearic acid and tr:imellitic acid, and also complex linear polyesters, polymeric plasticisers and epox:i.dised Le A 27 749 - 34 -soybean oils. The amount of plasticiser is approximately to 50~ by weight, preferably about 20 to 45~ by weight, of the entire composition.
The collars can also contain other components such as 5 stabilisers, spreading agents, lubricants, fillers and colourants, without this changing the basic properties of the composition. Suitable stabilisers are antioxidants and agents which protect 'the collars from ultraviolet rays and undesired degradation during processing, such as 10 extrusion moulding. home stabilisers, such as epoxidised soybean oils, also act as secondary plasticisers.
Examples of lubricants which can be used are stearates, stearic acid and low-molecular-weight polyethylenes.
These components can be used in a concentration of up to approximately 5~ by weight of the entire composition.
In the production of the collars according to the invention on a vinyl basis, the various components are mixed in the dry state using known mixing methods, and the mixture is moulded using known extruding or injection-moulding methods.
The choice of the processing method for the productian of the collars according to the invention depends technically in principle on the rheological properties of the collar material and the shape of the desired collar.
The processing methods can be adjusted to suit the processing technology or the nature of the shaping process. In the case of process technology, the methods Le A 27 749 - 35 -can be divided on the basis of the rheological states which the material assumes. Accordingly, pouring, pressing, inject on moulding and coating are suitable for viscous collar materials, and injection moulding, extruding, calendering, rolling and, if appropriate, edging in the case of elastoviscous polymers. Divided according to the nature of shaping, the mouldings according to the invention can be produced by casting, dipping, compression moulding, injection moulding, extruding, calendering, embossing, bending, thermoforming etc..
These processing methods are known and need no further explanation. What has been illustrated above by way of example for polyvinyl resins is also true in principle in the case of other polymers.
Other support materials fox the collars according to the invention are polyurethanes. These are prepared in a manner known per se by reacting polyisocyanates with high-molecular compounds which have at least two groups which are reactive towards isocyanates and, if appropriate, with low-molecular chain extenders and/or monofunctional chain terminators.
They are prepared by methods known in principle (for example compare European Offenlegungsschrift (Eux°opean Published Specification) 50,72, German 0ffenlegungs-schrift (German Published Specification) 2,715,595 and the references cited therein).
Le A 27 7~9 - 35 -~h~ concentrations of the active compounds in the support polymers are 0.05-20 ~ by weight. preferred concentrations are 0,1~5 ~ by weight. A concentration of active compound of around approximately 1 per cent by weight is particularly preferred.
In the examples below the following active compounds are used:
Pyriproxyfen: 2-[ 1-methyl-2-(4-phenoxyphenoxy)-ethoxyJ-pyridine Triflumuron = 1-(2-chloro't~nzoyl)-3-(4-trifluoromethoxyphenyl)-urea PrOpoxur = 2-isopropoxyphenyl-IV-methyl carbarnate Cyfluthrin: Cyano-(4-fiuoro-3-phenoxyphenyl)-methyl-3-(2,:~-dichlorovinyl)-2,2-dimethyl- cyclopropane carboxylate ~ A 27 719 - ~7 example A
The test is carried owt using PVC collars which contain 1~ by weight of the compound pyriproxyfen of the formula ~o~ c~az-cry-o l~\ /~..\ ! /-..\
xo Tiled pens of approx. 170 x 270 cm are covered with carpet ( 3 . 4 mZ) , the area of the reed bowls and litter tray remaining uncovered, and 2 cats wearing the collars to be tested are placed in the pens. After i week, the g5 carpets are removed from the pens and in each case 20 test discs of 80 mm diameter are cut out. T;he discs should be distributed on the carpet as uniformly as possible.
2p The carpet discs are scattered with a spatula-tipful of blood meal (specifications blood meal (powder) for feed purposes; manufactured by sniff ) , and infested with eggs or Ll larvae of the flea species to be tested. They are kept in an incubation cabinet at 2~°C/~0~ relative 25 humidity. The development of the flea larvae is checked every three days. The dishes in which larva development takes place are sealed tightly after about i4 days using Parafilm o~ Tesafilm so as to prevent the adult fleas 2a from escaping. The test is concluded one week after the fleas in the untreated controls have hatched. The dishes in which the development of adult f leas took place are k~pt for 2~ hours in a freezer at -15 - 1~°C and are then evaluated. even though larvae hatch from the eggs, no 25 adult fleas develop, even after 1~ weeks.
Le A 27 749 Production exarn~les Examples of polyurethane collars:
The collars are produced continuously by the casting process with the aid of a belt conveyor system.
The polyether, the active compound ar active compound combination, the colouring paste, the xeolite paste, the spreading agent and 1,4-butanediol are mixed together in a healable vessel and i ~ heated to 50°C. The catalyst (dibutyl tin dilaurate) is then added.
'The resulting mixture is component A, which is mixed with component B in a weight ratio of 1:1 using a mixing apparatus. The mixing head is attached to an oscillating traversing device. The reaction mixture flows continuously from the mixing head on to a supporting material (e.g. coating t 5 on a plastic belt). The reaction mixture begins to react 30 sets after issuing from the mixing head and hardens after about 60 sets.
The web of material then passes through a cooling zone. The product has solidified to such an extent that it can be passed to the cutting device via a system of slowly rotating '~1-belts.
2~
Example 1 component A:
Trihydroxypalyether (m.w. 4,800) 41.18 parts by weight 1,4-butanediol (crosslinking agent)5.00 "
Pigment (iron oxide) 0.50 "
Zealite paste (1:1 in castor oil)0.50 "
Tsiflumuron 10.00 3t7 1(lexyl laurate (spreading 1800 "
agent) I?ibutyl tin dilaurate 0.02 "
Component B:
35 'Tripropylene-glycol-madiHed 4,4'-diisacyanatodiphenylmethane, isacyanate content: 23°lo by weight 24.80 parts by weight Le A ~7 '7~9 - 39 °
Example 2 a Component A:
Trihydroxypolyether (m.w. 4,800) 39.063 parts by weight 1,4-butanediol 5.000 "
Pigment (iron oxide) 0.500 "
2eolite past ( 1:1 in castor oil) 0.500 ' Propoxur 8.00 "
Pyriproxyfen 1.00 Isopropyl myristate (spreading 22.00 "
agent) Dibutyl tin dilaurate 0.037 "
Component B:
'I'ripropylene-glycol-modified 4,4'-diisocyanatodiphenylmethane, isocyanate content: 23% by weight 23.90 parts by weight Example 3 Component A:
Trihydroxypolyether (m.w. 4,800) 51.48 parts by vsreight 1,4-butanediol 5.00 '"
Pyriproxyfen 1.50 "
Cyfluthrin 7.50 ' Pigment (iron oxide) 0.50 "
Zeolite paste (1:1 castor oil) 0.50 "
Ester of a branched fatty acid with saturated fatty alcohois/Cta-Cts (spreading agent) 8.00 "
Dibutyl tin dilaurate 0.02 ' ~e A 27 749 - 40 -°
Component B:
Tripropylene-glycol-modified 4,4'-diisocyanatodiphenylmethane, isocyanate content: 23% by weight 25.50 parts by weight Examples of PVC collars The active compound, the colourant and the PVC homopolymer are initially fed into a high-speed mixer and mixed thoroughly. The speed of the mixer is increased and the teml~rature raised to ~60°C.
i ~ Then diisobutyl adipate, dioctyl phthalate and the wetting agent are added and the mixture is mixed further until the temperature has again reached 60°C.
The mixture is slowly stirred further until it is dry and powdery in appearance.
Then stearic acid is added.
The mixture is then cooled rapidly with stirring.
This mixture is processed in an injection-moulding machine to foam collars of the appropriate shape.
Example ~~
Pyriproxyfen 0.70 parts by weight l3usobutyl adipate 23.25 Dioctyl phthalate 10.03 Epoxidised soybean oil (wetting agent) 2.54 ~tearic acid 0'gg Iron oxide pigment 0.14 ' PVC homopalymer 62.44 r.o n ~~ 7dA - 41 -Example 5 1'yriproxyfen 0.20 parts by weight Propoxur 10.0V vv Diisobutyl adipate 17.25 "
Dioctyl phthalate 6.03 "
Epoxidised soybean oil 2.54 "
Stearic acid 0.88 PVC homopolymer 62.96 "
I5 Example 6 Pyriproxyfen 0.50 parts by weight Cyftuthrin 10.00 "
Stearic acid 0.88 Iron oxide pigment 0.10 "
PVC homopolymer 60.52 "
Tributyl citrate 18.00 Triacetin 10.00 ~e A 27 749 - 42 -
N
o O -cH~-cH---~~~---N o i N.---N ~
CHI
0 O _CFI~_CH_ ,~-N O
I N~N
ccz~ cH~
r~
S 0 -CHI-CHw -~~---N
O
I N~N ~
CC1~
~e A 27 749 - lg -The substituted diaryl ethers furthermore include the compounds of the formula (III) R~ R4 R1 s ~ ~ ~. _CHs ,,.CH_ ~ ~5 X 2 ~ Y ° (ITI) F~
where x represents 0, S, D1H, -CHI-, --CHCH3-, -~ ( CH3 ) 2-Y represents straight-chain or branched alkylene which is optionally interrupted by oxygen, R1 represents identical or different radica7.s from the group comprising hydrogen, halogen, alkyl, alkaxy and halogenaalkyl, R2 represents identical ax different radica~.s from the group comprising hydrogen, halogen, alkyl, alkenyl, halagenoalkyl, alkoxy, alkylthio, halogenoalko~cy and halogenoalkylthia, R3 represents hydrogen, alkyl, halagenaalkyl, alkaxyalkyl, alkenaxyalkyl, alkenyl ar alkinyl, R" repxesents the radicals mentioned under R~, R3 and R~ tagethes can represent a direct bond, an~cl Le ~4 27 749 - 19 -v~5 RS repre~ent~ hydrogen, halogen, alkyl, halogeno-alkyl, al3soxy, amino, alkyl, alkylamino, dialkyld amino ox acylamino.
The following array ~e mentioned in particulars _ ~~ ~\
~ z Ct ~"
~--- 5 0 1.3 C1~ -CH2-CHZ-0-CH~-CH- 3-NH2 iH3 S H -CHICH-0-CHZ-CH- 5-N~a o. 1.3-C1~ -CH2-CHZ-0-CH~CH~- 4-NF-l~
p 1.3-C12 -CH2-CH~-0-CH~CHZ- 3-oCH3 S 1.3-Clz -CHI-CHI-C3-CHZCH~- S-OCH3 Q 3-8r -CHI-CH~-0-CH~CP4~- S-OCH3 CH2 1.3-C1~ -CHI-CHZ-0-CH~CH2-0-CH~CH~-CH2 H -CHI-CHI-O-CH2-CH 5-C~"3 0 H -CH2-~H-0-CHZ-iH- 5N~
S H CH~-iHO-CH~-CH2- 5-NON-CH3 0 1.3-C1~ -CHZ-CHZ-0-CH2CH2-3-NH-C-NH f~_\ ~~\
~I
!H3 ~CH3 0 1.3-C12 -CHZ-CH-0-CH2CH2- 5-~N~O
~....~
S 1.3-C1~ -CHI-CH-0-CHZ-rH2-5-N~
Le A 2? ?49 - 21 -X F~'~ a R 5 iH3 ,~CH3 CHI 1.3-C1~ -CHI-CH-0-CH~CH~° 5-N~0 O H -CHI°CHZ-0-CH2CH2° 5°N~O
O 1.3°C1~ --CHZCI-1~0-CHZ°CH~- 3°NH-C-NH ~
ii -CH- H -CH2CH~°O°CNZCH~° 4°OCH3 i i O H 3°NH°C-NH ~
0 H -CH2CHZ°0°CHZCH2CH2° 4°NH°C-NH' F3 i ~l 7~~ A 27 7~9 - 22 -The diaryl ethers furthermore include the compounds of the formula (IV) Het-X
o cp n c;-cH~~ ~-Z (xV~
~s in which Het represents an optionally sulastituted hetero-aromatic radical represents O, S, -CHZ°, °O-CH2-, -''a-~I~Ig~-, -C:HZ-O-O
I I
_C°D _C_ N-O-C1-~4-alkyl , Y represents O, -0-CHZ-, S, Z represents an optianally substituted aromatic or heteroaromatic radical;
m represents integers from 1 to ~&, n represents 0, 1, 2, 3 or 4, o represents 0, 1, 2, 3 or ~, where n and o must not simultaneously represent 0, Le A 27 749 - 23 °
p represents integers from 1 to 4, R2, R3, R~, 'R5, R6 independently of one another represent hydrogen, C1-C6-alkyl, which is optionally sub-stituted by halogen or C1_4-alko~cy; two radicals which axe adjacent to each other can also, together with the C atoms to which they are bonded, form a saturated carbocyclic 5- or 6-ring, and R1 represents identical or different radicals from the group comprising hydrogen, halogen, CN, C1_4-alkyl, 1-5-halogeno-C1_~-alkyl, C1_4-alkoxy, C1_4-alkylthio, 1-5-halogeno-C1_~-al3coacy, 1-5-halogeno--C1_4-alkylthio, phenyl or phenoxy.
The following may be mentioned in particulars x ~'~r-o ( -a d D o-sae ~.
~°N X ~ ~' ~1 a x R 1 B ~I ~t t j~~s o a . a-cy -c~az-c~-Le A z~ ~~~ - z4 -X R1 ~ Hit CF"3 H -CHI-CH I
0 1.3-C1~ -CH2-CH- r I
I h~
CHEF
0 1.3C1~ -CHZ-CH I
I std CHZ-F' S 1.3-C12 _CH2-CH- r I
I
CHZ-~' CHZ 1.3-C12 _CH~-CH- r I
I h~
CH2_F
CH2 H -CH2-CH- r I
I .~-'N
CH2_F
0 H CH~-CH-~t~P
CHEF' S H -CHI-CH- r I
~N
CH~~"
T~e da 2"7 a~9 - 25 -H1 ~ Het 0 1.3-C1~ -CHI-CH-CHEF
iH3 ~CH3 0 1 -CH ! ~ N
3-Cl -CH-. 2 0 Z
H3 /~'~CH3 S 1 -CH ~~~~ --3J 0 . 2 p,~'~"T~ ~.--~
CH2 1.3-C1~ _CH~-CH_ ! ~ N
H
0 H -CH ! ~ IJ~O
-CH-C;H3 ~H3 I
0 1.3-C12 -CHaGH~O-CHI-CH~- v Le A 27 749 - 2~ --~ n ~i 1 xYC-B-)-o-Hat X Y B Het r O S -CH2CH20CH~CH~
°
0 0 CH2-CHZ-0-CH~-CHI
s 0 S -CHI-iH-S 0 -CH2-iH-CHI-F
0 0 -CH2-CH- °
CHc -~' CH~_F
ri Le A 27 749 - ~7 ~-X Y ~~ Het I H --~~---N~N-cH ~
0 O -CHI-CH- N-°'N
CHI
~~---_N'~o O o -CHZ-CH- N-N
cH3 cH~F
/CHI
S O - CH ~ - C i - --~-~N~N--CH
N...aN \C H 3 CHEF
CHI
Ck.p~ O °CH~-CH- '.~N O
I N--mN \"'°"~
CFA CHI
O O -CH2 CH ~~~N~,O
I N°'-N
O O _C~I~_CH- -'-~N O
N-N
CC;I ~ CHI
o - CH z _ c ~ _ --,~~---.NCO
N-°-N
CCl~
La A 27 7~9 - 28 -The benzoylureas inolude compounds of the formula (V):
R~ V
~ ~-NH-coNH( ) '°~R4 RZ
where R1 represents halogen, Rz represents hydrogen or halogen, R3 represents hydrogen, halogen or C1_4-alkyl, R4 represents halogen, 1-5-halogeno-C1_4-alkyl, Cl_4-alko~cy, 1-5-halogeno-C1_4-alkoxy, Cl_4-alkyl-thin, 1-5-halogens-C1_~,-alkylthio, pheno:Ky or ltd pyridyloxy, each of whioh aan be optionally substituted by halogen, C1_m-alkyl, 1-5-halogeno-Cl_4-alkyl, C1_4-alkoary, 1-5-halogeno-Cl_4--alkoxy, C1_4-alkylthio, or 1-5-halogeno-C1-C4-alkylthio.
The following may be mentioned in particular:
R~
ONHCONH ° ~ ~ R'~
- ~e :~ 27 749 - 29 -F F CFS
F F SCFS
H F OCFS
F F 0 ~~~ C1 F F 0 ~~~ CF3 F F 0 ~~.~ CF3 the ~triazines include compounds of the formula (VT) N, IN (VI) .
wheria he A ~7 74~ m 30 -~~~
R1 represents cyclopropyl or isopropyl;
Rz represents hydrogen, halogen, C1-Clz--alkyl-carbonyl, cyclopropylcarbonyl, Cz-Clz-alkl-carbamoyl, C~-Clz-alkylthiocarbamoyl or Cz-C6-alkenylcarbamoyl; and R3 represents hydrogen, C1-C~z-alkyl, cyclopropyl, Cz-Cs-alkenyl, C1-Ciz-alkylcarbonyl, cyclopropyl-carbonyl, C1-Clz-alkylcarbamoyl, C1-Clz-alkylthio-carbamoyl or Cz-C6-alkenylcarbamoyl, and their acid addition salts which are non-toxic to warm-blooded species.
The following may be mentioned in particularo Cyclopropyi H H
Cyclopropyi H CHI
Cyclopropyl H CZHS
Cyclapropyl H C~H7-n Cyc 1 opropyl H C,~Hc~-n Cyclopropyl H CSHqq-n Cyclopropyl H C6Hq~-n Cyclopropyl H C~HqS-n Cyclopropyl H C~H1?-n ~e A 27 749 - 31 -( con-tinua~ion) Cyclopropyl H C12H25 n Cyclopropyl H CH2-CgH9-t Cyclopropyl H CH2CH(CH3)C2H5 Cyelopropyl H CH2CH-CH2 Cyclopropyl C1 Cyclopropyl C1 C6H13-n Cyclopropyl C1 C8H1~.-n Cyclopropyl C1 C12H25"n Cyclopropyl H Cyclopropyl Cyclopropyl H COCH3 Cyclopropyl H COCH3'HC1 Cyeloprapyl H C0C2H5'HC1 Cyclopropyl H COC2H5 Cyclopropyl H COC3H~-n Cyclopropyl H COC3Hp-i Cyclopropyl H COC4H9-tHCl Cyclopropyl H COCaH9-n Cyclopropyl H
COC~H13-n Cyclopropyl H COC11-H23-n Cyclopropyl COCH3 COC2H5 Cyclopropyl COC3H~-n COC6H13-n Cyclopropyl COCH3 COC3H~-n Cyclopropyl COC2H5 COC3H'-n Cyclopropyl H COCyclopropyl Cyclopropyl COCylclopropyl COCyclopropyl Cycloprapyl COCH3 COCH3 T~opropyl H H
Le A 27 749 ~ 32 (continuation) H1 R2 ~3 Isopropyl H COCHC
Isopropyl H COC~H~-n Cyclopropyl H CONHCH3 Cyclopropyl H C0NHC3H7-i Cyclopropyl CONHCH~ CONHCH~
Cyclopropyl H CSNHCH3 Cyclopropyl H CONHCH~CH=CHI
Cyclopropyl CONHCHZCH=CHZ CONHCHZCH=CHz Cyeloprapyl CSNHCH~ CSNHCH3 The abovementioned substituted diaxyl ethers of the formula I must be particularly emphasised.
Insecticides which may be incorporated into the collars according to the invention in addition to the development inhibitors mentioned axe: phosphates, such as, for example, fenthion, caxbamates such as, fox example, propoxux, pyrethxoids such as, fox example, cyfluthrin ox flumethxin.
1Q Substances which can be used for producing the collars according to the invention axe polyvinyl resins, poly-urethanes, polyacrylates, epoxy resins, cellulose, cellulose derivatives, polyamides and polyesters which axe suff~.ciewtly compatible with th~ abovementioned active compounds. The polymers must have suffic:Lently Le A 27 749 - 33 -high strength and flexibility so as not to crac3c or became brittle when formed into a collar. They must be sufficiently durable so as to be resistant to normal wear and tear. Moreover, the polymers must permit sufficient migration of the active compounds to the surface of the moulding. These properties are met, in particular, by solid polyvinyl resins, that is to say po:Lymers which are formed by polymers of a vinyl double bond.
Examples of typical vinyl resins are polyvinyl halides, such as polyvinyl chloride, polyvinyl chloride/vinyl acetate and polyvinyl fluoride; polyacrylate esters and polymethacrylate esters such as polymethyl acrylate and polymethyl methacrylate; and polyvinylbenzenes such as polystyrene and palyvinyltoluene.
Z5 Suitable plasticisers for the production of the collars according to the invention on the basis of polyvinyl resin are those which are customarily used for plastic-ising solid vinyl resins. The plasticiser to be used depends on the resin and .its compatibility with the 2~J plasticiser. Examples of suitable plasticisers are esters of phosphoric acid, such as tricresyl phosphate, esters of phthalic acid, such as dimethyl phthalate and dioctyl phthalate, and esters of adipic acid, such as diisobutyl adipate. It is also possible to use other esters, s7,ach as 25 the esters of azelaic acid, malefic acid, ric:inoleic acid, myristic acid, palmitic acid, oleic acid, sebacic acid, stearic acid and tr:imellitic acid, and also complex linear polyesters, polymeric plasticisers and epox:i.dised Le A 27 749 - 34 -soybean oils. The amount of plasticiser is approximately to 50~ by weight, preferably about 20 to 45~ by weight, of the entire composition.
The collars can also contain other components such as 5 stabilisers, spreading agents, lubricants, fillers and colourants, without this changing the basic properties of the composition. Suitable stabilisers are antioxidants and agents which protect 'the collars from ultraviolet rays and undesired degradation during processing, such as 10 extrusion moulding. home stabilisers, such as epoxidised soybean oils, also act as secondary plasticisers.
Examples of lubricants which can be used are stearates, stearic acid and low-molecular-weight polyethylenes.
These components can be used in a concentration of up to approximately 5~ by weight of the entire composition.
In the production of the collars according to the invention on a vinyl basis, the various components are mixed in the dry state using known mixing methods, and the mixture is moulded using known extruding or injection-moulding methods.
The choice of the processing method for the productian of the collars according to the invention depends technically in principle on the rheological properties of the collar material and the shape of the desired collar.
The processing methods can be adjusted to suit the processing technology or the nature of the shaping process. In the case of process technology, the methods Le A 27 749 - 35 -can be divided on the basis of the rheological states which the material assumes. Accordingly, pouring, pressing, inject on moulding and coating are suitable for viscous collar materials, and injection moulding, extruding, calendering, rolling and, if appropriate, edging in the case of elastoviscous polymers. Divided according to the nature of shaping, the mouldings according to the invention can be produced by casting, dipping, compression moulding, injection moulding, extruding, calendering, embossing, bending, thermoforming etc..
These processing methods are known and need no further explanation. What has been illustrated above by way of example for polyvinyl resins is also true in principle in the case of other polymers.
Other support materials fox the collars according to the invention are polyurethanes. These are prepared in a manner known per se by reacting polyisocyanates with high-molecular compounds which have at least two groups which are reactive towards isocyanates and, if appropriate, with low-molecular chain extenders and/or monofunctional chain terminators.
They are prepared by methods known in principle (for example compare European Offenlegungsschrift (Eux°opean Published Specification) 50,72, German 0ffenlegungs-schrift (German Published Specification) 2,715,595 and the references cited therein).
Le A 27 7~9 - 35 -~h~ concentrations of the active compounds in the support polymers are 0.05-20 ~ by weight. preferred concentrations are 0,1~5 ~ by weight. A concentration of active compound of around approximately 1 per cent by weight is particularly preferred.
In the examples below the following active compounds are used:
Pyriproxyfen: 2-[ 1-methyl-2-(4-phenoxyphenoxy)-ethoxyJ-pyridine Triflumuron = 1-(2-chloro't~nzoyl)-3-(4-trifluoromethoxyphenyl)-urea PrOpoxur = 2-isopropoxyphenyl-IV-methyl carbarnate Cyfluthrin: Cyano-(4-fiuoro-3-phenoxyphenyl)-methyl-3-(2,:~-dichlorovinyl)-2,2-dimethyl- cyclopropane carboxylate ~ A 27 719 - ~7 example A
The test is carried owt using PVC collars which contain 1~ by weight of the compound pyriproxyfen of the formula ~o~ c~az-cry-o l~\ /~..\ ! /-..\
xo Tiled pens of approx. 170 x 270 cm are covered with carpet ( 3 . 4 mZ) , the area of the reed bowls and litter tray remaining uncovered, and 2 cats wearing the collars to be tested are placed in the pens. After i week, the g5 carpets are removed from the pens and in each case 20 test discs of 80 mm diameter are cut out. T;he discs should be distributed on the carpet as uniformly as possible.
2p The carpet discs are scattered with a spatula-tipful of blood meal (specifications blood meal (powder) for feed purposes; manufactured by sniff ) , and infested with eggs or Ll larvae of the flea species to be tested. They are kept in an incubation cabinet at 2~°C/~0~ relative 25 humidity. The development of the flea larvae is checked every three days. The dishes in which larva development takes place are sealed tightly after about i4 days using Parafilm o~ Tesafilm so as to prevent the adult fleas 2a from escaping. The test is concluded one week after the fleas in the untreated controls have hatched. The dishes in which the development of adult f leas took place are k~pt for 2~ hours in a freezer at -15 - 1~°C and are then evaluated. even though larvae hatch from the eggs, no 25 adult fleas develop, even after 1~ weeks.
Le A 27 749 Production exarn~les Examples of polyurethane collars:
The collars are produced continuously by the casting process with the aid of a belt conveyor system.
The polyether, the active compound ar active compound combination, the colouring paste, the xeolite paste, the spreading agent and 1,4-butanediol are mixed together in a healable vessel and i ~ heated to 50°C. The catalyst (dibutyl tin dilaurate) is then added.
'The resulting mixture is component A, which is mixed with component B in a weight ratio of 1:1 using a mixing apparatus. The mixing head is attached to an oscillating traversing device. The reaction mixture flows continuously from the mixing head on to a supporting material (e.g. coating t 5 on a plastic belt). The reaction mixture begins to react 30 sets after issuing from the mixing head and hardens after about 60 sets.
The web of material then passes through a cooling zone. The product has solidified to such an extent that it can be passed to the cutting device via a system of slowly rotating '~1-belts.
2~
Example 1 component A:
Trihydroxypalyether (m.w. 4,800) 41.18 parts by weight 1,4-butanediol (crosslinking agent)5.00 "
Pigment (iron oxide) 0.50 "
Zealite paste (1:1 in castor oil)0.50 "
Tsiflumuron 10.00 3t7 1(lexyl laurate (spreading 1800 "
agent) I?ibutyl tin dilaurate 0.02 "
Component B:
35 'Tripropylene-glycol-madiHed 4,4'-diisacyanatodiphenylmethane, isacyanate content: 23°lo by weight 24.80 parts by weight Le A ~7 '7~9 - 39 °
Example 2 a Component A:
Trihydroxypolyether (m.w. 4,800) 39.063 parts by weight 1,4-butanediol 5.000 "
Pigment (iron oxide) 0.500 "
2eolite past ( 1:1 in castor oil) 0.500 ' Propoxur 8.00 "
Pyriproxyfen 1.00 Isopropyl myristate (spreading 22.00 "
agent) Dibutyl tin dilaurate 0.037 "
Component B:
'I'ripropylene-glycol-modified 4,4'-diisocyanatodiphenylmethane, isocyanate content: 23% by weight 23.90 parts by weight Example 3 Component A:
Trihydroxypolyether (m.w. 4,800) 51.48 parts by vsreight 1,4-butanediol 5.00 '"
Pyriproxyfen 1.50 "
Cyfluthrin 7.50 ' Pigment (iron oxide) 0.50 "
Zeolite paste (1:1 castor oil) 0.50 "
Ester of a branched fatty acid with saturated fatty alcohois/Cta-Cts (spreading agent) 8.00 "
Dibutyl tin dilaurate 0.02 ' ~e A 27 749 - 40 -°
Component B:
Tripropylene-glycol-modified 4,4'-diisocyanatodiphenylmethane, isocyanate content: 23% by weight 25.50 parts by weight Examples of PVC collars The active compound, the colourant and the PVC homopolymer are initially fed into a high-speed mixer and mixed thoroughly. The speed of the mixer is increased and the teml~rature raised to ~60°C.
i ~ Then diisobutyl adipate, dioctyl phthalate and the wetting agent are added and the mixture is mixed further until the temperature has again reached 60°C.
The mixture is slowly stirred further until it is dry and powdery in appearance.
Then stearic acid is added.
The mixture is then cooled rapidly with stirring.
This mixture is processed in an injection-moulding machine to foam collars of the appropriate shape.
Example ~~
Pyriproxyfen 0.70 parts by weight l3usobutyl adipate 23.25 Dioctyl phthalate 10.03 Epoxidised soybean oil (wetting agent) 2.54 ~tearic acid 0'gg Iron oxide pigment 0.14 ' PVC homopalymer 62.44 r.o n ~~ 7dA - 41 -Example 5 1'yriproxyfen 0.20 parts by weight Propoxur 10.0V vv Diisobutyl adipate 17.25 "
Dioctyl phthalate 6.03 "
Epoxidised soybean oil 2.54 "
Stearic acid 0.88 PVC homopolymer 62.96 "
I5 Example 6 Pyriproxyfen 0.50 parts by weight Cyftuthrin 10.00 "
Stearic acid 0.88 Iron oxide pigment 0.10 "
PVC homopolymer 60.52 "
Tributyl citrate 18.00 Triacetin 10.00 ~e A 27 749 - 42 -
Claims (23)
1. A collar for domestic animals comprising a surface that, in use, is exposed to the atmosphere and bears one or more insect-development-inhibiting compounds selected from the group consisting of juvenile hormones and juvenile-hormone-type substances, substituted diaryl ethers, benzoyl ureas and triazine derivatives.
2. A collar according to claim 1 wherein the insect-development-inhibiting compound is selected from a group of juvenile hormones and juvenile-hormone-type substances of the following formulae:
3. A collar according to claim 1 wherein the insect-development-inhibiting compound is selected from a group of substituted diaryl ethers of general formula (I):
where R1 represents hydrogen, halogen, alkyl, alkoxy, alkythio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, dioxyalkylene, dioxyhalogenoalkylene, CN, NO2, alkenyl, alkinyl, alkoxyalkyl, alkoxyalkoxy or hydroxyalkoxy, R2 represents the radicals mentioned under R1, R3 represents the radicals mentioned under R1, R4 represents hydrogen, alkyl, halogenoalkyl or halogen, R5 represents the radicals mentioned under R4, Het represents optionally substituted heteroaryl which is not bonded to the remaining radical via the heteroatom, X and Y independently of one another represent -O- or -S-, Z represents -O-, -S-, -CH2-, -CHCH3-, -C(CH3)2-, m and n independently of one another represent 0, 1, 2 or 3, but their total is equal to, or greater than, 2.
where R1 represents hydrogen, halogen, alkyl, alkoxy, alkythio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, dioxyalkylene, dioxyhalogenoalkylene, CN, NO2, alkenyl, alkinyl, alkoxyalkyl, alkoxyalkoxy or hydroxyalkoxy, R2 represents the radicals mentioned under R1, R3 represents the radicals mentioned under R1, R4 represents hydrogen, alkyl, halogenoalkyl or halogen, R5 represents the radicals mentioned under R4, Het represents optionally substituted heteroaryl which is not bonded to the remaining radical via the heteroatom, X and Y independently of one another represent -O- or -S-, Z represents -O-, -S-, -CH2-, -CHCH3-, -C(CH3)2-, m and n independently of one another represent 0, 1, 2 or 3, but their total is equal to, or greater than, 2.
4. The collar of claim 3 wherein with respect to the substituted diaryl ethers of general formula (I):
R1 represents hydrogen, fluorine, chlorine, bromine, C1-4-alkyl, C1-4-alkoxy, C1-4-alkylthio, C1-4-halogenoalkyl having up to 5 halogen atoms, in particular trichloromethyl, trifluoromethyl, C1-4-halogenoalkoxy having up to 5 halogen atoms, in particular trichloromethoxy, trifluoromethoxy, C1-4-halogenoalkylthio having up to 4 halogen atoms, in particular trifluoromethylthio CN, NO2, C2-3-alkenyl, C1-4-alkoxy-C1-2-alkyl, in particular ethoxymethyl, methoxyethyl, C1-2-alkoxy-C1-4-alkoxy, in particular methoxyethoxy, C1-4-hydroxyalkoxy, in particular hydroxyethoxy, dioxyethylene, dioxymethylene, difluorodioxymethylene, trifluorodioxyethylene or dichlorooxymethylene, R2 represents the radicals mentioned under R1, R3 represents the radicals mentioned under R1, R4 represents hydrogen, C1-4-alkyl, C1-4-halogenoalkyl having up to 5 halogen atoms, chlorine, fluorine or bromine, R5 represents the radicals mentioned under R4, Het represents pyridyl, pyridazinyl, pyrimidinyl, or pyrazinyl, each of which is optionally substituted by one or more identical or different radicals from the group comprising C1-4-alkyl, such as methyl, ethyl, t-butyl, halogen, such as fluorine, chlorine, bromine, NO2, C1-4-alkoxy, C1-4-alkylthio, C1-4-alkoxy, C1-4-alkylthio, C1-4-halogenoalkyl having up to 5 halogen atoms, C1-4-halogenoalkoxy having up to 5 halogen atoms or C1-4-halogenoalkylthio having up to 5 halogen atoms, X and Y independently of one another represent -O- or -S-, Z represents -O-, -S-, -CH2-, -CHCH3-, -C(CH3)2-, m represents 1 or 2, and n represents 1 or 2.
R1 represents hydrogen, fluorine, chlorine, bromine, C1-4-alkyl, C1-4-alkoxy, C1-4-alkylthio, C1-4-halogenoalkyl having up to 5 halogen atoms, in particular trichloromethyl, trifluoromethyl, C1-4-halogenoalkoxy having up to 5 halogen atoms, in particular trichloromethoxy, trifluoromethoxy, C1-4-halogenoalkylthio having up to 4 halogen atoms, in particular trifluoromethylthio CN, NO2, C2-3-alkenyl, C1-4-alkoxy-C1-2-alkyl, in particular ethoxymethyl, methoxyethyl, C1-2-alkoxy-C1-4-alkoxy, in particular methoxyethoxy, C1-4-hydroxyalkoxy, in particular hydroxyethoxy, dioxyethylene, dioxymethylene, difluorodioxymethylene, trifluorodioxyethylene or dichlorooxymethylene, R2 represents the radicals mentioned under R1, R3 represents the radicals mentioned under R1, R4 represents hydrogen, C1-4-alkyl, C1-4-halogenoalkyl having up to 5 halogen atoms, chlorine, fluorine or bromine, R5 represents the radicals mentioned under R4, Het represents pyridyl, pyridazinyl, pyrimidinyl, or pyrazinyl, each of which is optionally substituted by one or more identical or different radicals from the group comprising C1-4-alkyl, such as methyl, ethyl, t-butyl, halogen, such as fluorine, chlorine, bromine, NO2, C1-4-alkoxy, C1-4-alkylthio, C1-4-alkoxy, C1-4-alkylthio, C1-4-halogenoalkyl having up to 5 halogen atoms, C1-4-halogenoalkoxy having up to 5 halogen atoms or C1-4-halogenoalkylthio having up to 5 halogen atoms, X and Y independently of one another represent -O- or -S-, Z represents -O-, -S-, -CH2-, -CHCH3-, -C(CH3)2-, m represents 1 or 2, and n represents 1 or 2.
5. A collar according to claim 3 wherein, with respect to the substituted diaryl ethers of general formula (I):
R1 represents hydrogen, methyl, trifluoromethyl, methoxy, trifluoromethoxy, chlorine or flourine, R2 represents hydrogen, R3 represents hydrogen, fluorine, chlorine or methyl, R4 represents hydrogen or methyl, R5 represents methyl, ethyl, trifluoromethyl or hydrogen, Het represents pyridyl or pyridazinyl, each of which is optionally substituted by fluorine, chlorine, methyl, NO2, methoxy or methylmercapto, X represents O, Y represents O, Z represents O, CH2 or -C(CH3)2-, m represents 1, n represents 1.
R1 represents hydrogen, methyl, trifluoromethyl, methoxy, trifluoromethoxy, chlorine or flourine, R2 represents hydrogen, R3 represents hydrogen, fluorine, chlorine or methyl, R4 represents hydrogen or methyl, R5 represents methyl, ethyl, trifluoromethyl or hydrogen, Het represents pyridyl or pyridazinyl, each of which is optionally substituted by fluorine, chlorine, methyl, NO2, methoxy or methylmercapto, X represents O, Y represents O, Z represents O, CH2 or -C(CH3)2-, m represents 1, n represents 1.
6. A collar according to claim 5 wherein the insect-development-inhibiting compound is of the formula:~~
7. A collar according to claim 1 wherein the insect-development-inhibiting compound is selected from a group of substituted diaryl ethers of general formula (II):
where X represents O, S, NH, -CH2-, -CHCH3-, -C(CH3)2-, Y represents O or S, Z represents O or S, R1 represents identical or different radicals from the group comprising hydrogen, halogen, alkyl, alkoxy or halogenoalkyl, 47~
R2 represents identical or different radicals from the group comprising hydrogen, halogen, alkyl, alkenyl, halogenoalkyl, alkoxy, alkylthio, halogenoalkoxy or halogenoalkylthio, R3 represents hydrogen, alkyl, halogenoalkyl, alkoxyalkyl, alkenoxyalkyl, alkenyl or alkinyl, R4 represents the radicals mentioned under R3, R3 and R4 together with the adjacent C atoms can represent saturated or unsaturated 5- to 7-membered carbocyclic rings, m represents 1 or 2, n represents 1 or 2, o represents 1, 2 or 3 and Het represents optionally substituted heteroaryl which is not bonded to the remaining radical via the heteroatom.
where X represents O, S, NH, -CH2-, -CHCH3-, -C(CH3)2-, Y represents O or S, Z represents O or S, R1 represents identical or different radicals from the group comprising hydrogen, halogen, alkyl, alkoxy or halogenoalkyl, 47~
R2 represents identical or different radicals from the group comprising hydrogen, halogen, alkyl, alkenyl, halogenoalkyl, alkoxy, alkylthio, halogenoalkoxy or halogenoalkylthio, R3 represents hydrogen, alkyl, halogenoalkyl, alkoxyalkyl, alkenoxyalkyl, alkenyl or alkinyl, R4 represents the radicals mentioned under R3, R3 and R4 together with the adjacent C atoms can represent saturated or unsaturated 5- to 7-membered carbocyclic rings, m represents 1 or 2, n represents 1 or 2, o represents 1, 2 or 3 and Het represents optionally substituted heteroaryl which is not bonded to the remaining radical via the heteroatom.
8. A collar according to claim 1 wherein the insect-development-inhibiting compound is selected from a group of substituted diaryl ethers of general formula (III):
where X represents O, S, NH, -CH2-, -CHCH3-, -C(CH3)2-, Y represents straight-chain or branched alkylene which is optionally interrupted by oxygen, R1 represents identical or different radicals from the group comprising hydrogen, halogen, alkyl, alkoxy and halogenoalkyl, R2 represents identical or different radicals from the group comprising hydrogen, halogen, alkyl, alkenyl, halogenoalkyl, alkoxy, alkylthio, halogenoalkoxy and halogenoalkylthio, R3 represents hydrogen, alkyl, halogenoalkyl, alkoxyalkyl, alkenoxyalkyl, alkenyl or alkinyl, R4 represents the radicals mentioned under R3, R3 and R4 together can represent a direct bond, and R5 represents hydrogen, halogen, alkyl, halogenoalkyl, alkoxy, amino, alkyl, alkylamino, dialkylamino or acylamino, mixed with a polymer selected from the group consisting of polyvinyl halides, polyacrylate or polymethacrylate esters, polyvinyl benzenes and polyurethanes, to form a mixture which is molded to form the exposed surface layer of the collar.
where X represents O, S, NH, -CH2-, -CHCH3-, -C(CH3)2-, Y represents straight-chain or branched alkylene which is optionally interrupted by oxygen, R1 represents identical or different radicals from the group comprising hydrogen, halogen, alkyl, alkoxy and halogenoalkyl, R2 represents identical or different radicals from the group comprising hydrogen, halogen, alkyl, alkenyl, halogenoalkyl, alkoxy, alkylthio, halogenoalkoxy and halogenoalkylthio, R3 represents hydrogen, alkyl, halogenoalkyl, alkoxyalkyl, alkenoxyalkyl, alkenyl or alkinyl, R4 represents the radicals mentioned under R3, R3 and R4 together can represent a direct bond, and R5 represents hydrogen, halogen, alkyl, halogenoalkyl, alkoxy, amino, alkyl, alkylamino, dialkylamino or acylamino, mixed with a polymer selected from the group consisting of polyvinyl halides, polyacrylate or polymethacrylate esters, polyvinyl benzenes and polyurethanes, to form a mixture which is molded to form the exposed surface layer of the collar.
9. A collar according to claim 1 wherein the insect-development-inhibiting compound is selected from a group of substituted diaryl ethers of general formula (IV):
in which Het represents an optionally substituted heteroaromatic radical, X represents O, S, -CH2-, -O-CH2-, -S-CH2-, -CH2-O- Y represents O, -O-CH2-, S
Z represents an optionally substituted aromatic or heteroaromatic radical;
m represents integers from 1 to 4, n represents 0, 1, 2, 3 or 4, o represents 0, 1, 2, 3 or 4, where n and o must not simultaneously represent 0, p represents integers from 1 to 4, R2, R3, R4, R5, R6 independently of one another represent hydrogen, C1-6-C-alkyl, which is optionally substituted by halogen or C1-4-alkoxy; two radicals which are adjacent to each other can also, together with the C atoms to which they are bonded, form a saturated carbocyclic 5- or 6-ring, and R1 represents identical or different radicals from the group comprising hydrogen, halogen, CN, C1-4-alkyl, 1-5-halogeno-C1-4-alkyl, C1-4-alkoxy, C1-4-alkylthio, 1-5-halogeno-C1-4-alkoxy, 1-5-halogeno-C1-4-alkylthio, phenyl or phenoxy.
in which Het represents an optionally substituted heteroaromatic radical, X represents O, S, -CH2-, -O-CH2-, -S-CH2-, -CH2-O- Y represents O, -O-CH2-, S
Z represents an optionally substituted aromatic or heteroaromatic radical;
m represents integers from 1 to 4, n represents 0, 1, 2, 3 or 4, o represents 0, 1, 2, 3 or 4, where n and o must not simultaneously represent 0, p represents integers from 1 to 4, R2, R3, R4, R5, R6 independently of one another represent hydrogen, C1-6-C-alkyl, which is optionally substituted by halogen or C1-4-alkoxy; two radicals which are adjacent to each other can also, together with the C atoms to which they are bonded, form a saturated carbocyclic 5- or 6-ring, and R1 represents identical or different radicals from the group comprising hydrogen, halogen, CN, C1-4-alkyl, 1-5-halogeno-C1-4-alkyl, C1-4-alkoxy, C1-4-alkylthio, 1-5-halogeno-C1-4-alkoxy, 1-5-halogeno-C1-4-alkylthio, phenyl or phenoxy.
10. A collar according to claim 1 wherein the insect-development-inhibiting compound is selected from a group of benzoyl ureas of general formula (V):
where R1 represents halogen, R1 represents hydrogen or halogen, R3 represents hydrogen, halogen or C1-4-alkyl, R4 represents halogen, 1-5-halogeno-C1-4-alkyl, C1-4-alkoxy, 1-5-halogeno-C1-4-alkoxy, C1-4-alkylthio, 1-5-halogeno-C1-4-alkylthio, phenoxy or pyridyloxy, each of which can be optionally substituted by halogen, C1-4-alkyl, 1-5-halogeno-C1-4-alkyl, C1-4-alkoxy, 1-5-halogeno-C1-4-alkoxy, C1-4-alkylthio, or 1-5-halogeno-C1-C4-alkylthio.
where R1 represents halogen, R1 represents hydrogen or halogen, R3 represents hydrogen, halogen or C1-4-alkyl, R4 represents halogen, 1-5-halogeno-C1-4-alkyl, C1-4-alkoxy, 1-5-halogeno-C1-4-alkoxy, C1-4-alkylthio, 1-5-halogeno-C1-4-alkylthio, phenoxy or pyridyloxy, each of which can be optionally substituted by halogen, C1-4-alkyl, 1-5-halogeno-C1-4-alkyl, C1-4-alkoxy, 1-5-halogeno-C1-4-alkoxy, C1-4-alkylthio, or 1-5-halogeno-C1-C4-alkylthio.
11. A collar according to claim 1 wherein the insect-development-inhibiting compound is selected from a group consisting of triazines of general formula (VI):
where R1 represents cyclopropyl or isopropyl;
R2 represents hydrogen, halogen, C1-C12-alkyl-carbonyl, cyclopropylcarbonyl, C1-C12-alkylcarbamoyl. C1-C12-alkylthiocarbamoyl or C2-C6-alkenylcarbamoyl; and R3 represents hydrogen, C1-C12-alkyl, cyclopropyl, C2-C6-alkenyl, C1-C12-alkylcarbonyl, cyclopropylcarbonyl, C1-C12-alkylcarbamoyl, C1-C12-alkylthiocarbamoyl or C2-C6-alkenylcarbamoyl, and their acid addition salts which are non-toxic to warm-blooded species.
where R1 represents cyclopropyl or isopropyl;
R2 represents hydrogen, halogen, C1-C12-alkyl-carbonyl, cyclopropylcarbonyl, C1-C12-alkylcarbamoyl. C1-C12-alkylthiocarbamoyl or C2-C6-alkenylcarbamoyl; and R3 represents hydrogen, C1-C12-alkyl, cyclopropyl, C2-C6-alkenyl, C1-C12-alkylcarbonyl, cyclopropylcarbonyl, C1-C12-alkylcarbamoyl, C1-C12-alkylthiocarbamoyl or C2-C6-alkenylcarbamoyl, and their acid addition salts which are non-toxic to warm-blooded species.
12. A collar according to any one of claims 1 to 11 wherein the insect-development-inhibiting compound is mixed with a polymer selected from the group consisting of polyvinyl halides, polyacrylate or polymethacrylate esters, polyvinylbenzenes and polyurethanes to form a mixture which is molded to form the exposed surface layer of the collar.
13. A collar according to any one of claims 1 to 12 wherein the insect-development-inhibiting compound is present in an amount from 0.05 to 20% by weight of the surface layer.
14. A collar according to claim 13 wherein the insect-development-inhibiting compound is present in an amount from 0.1 to 5% by weight of the surface layer.
15. A collar according to claim 14 wherein the insect-development-inhibiting compound is present in an amount of approximately 1% by weight of the surface layer.
16. A collar according to any one of claims 1 to 15 wherein the surface layer additionally comprises one or more insecticides selected from the group consisting of an organophosphate, a carbamate and a pyrethroid.
17. A collar according to claim 16 wherein the insecticide is a carbamate.
18. A collar according to claim 17 wherein the carbamate is propoxur.
19. A collar according to claim 16 wherein the insecticide is an organophosphate.
20. A collar according to claim 16 wherein the insecticide is a pyrethroid
21. A collar according to claim 16 wherein the insecticide is cyfluthrin.
22. A collar according to claim 16 wherein the insecticide is flumethrin.
23. A method of combating fleas on, and in the surroundings of a domestic animal which comprises placing on the animal a collar according to any one of claims 1 to 22.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4025345A DE4025345A1 (en) | 1990-08-10 | 1990-08-10 | METHOD AND MEANS FOR COMBATING FLUES |
DEP4025345.7 | 1990-08-10 |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2048543A1 CA2048543A1 (en) | 1992-02-11 |
CA2048543C true CA2048543C (en) | 2001-06-05 |
Family
ID=6411985
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002048543A Expired - Lifetime CA2048543C (en) | 1990-08-10 | 1991-08-07 | Processes and agents for combating fleas |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP0470467B1 (en) |
JP (1) | JPH04229125A (en) |
KR (1) | KR100202152B1 (en) |
AT (1) | ATE111298T1 (en) |
AU (1) | AU656141B2 (en) |
CA (1) | CA2048543C (en) |
DE (2) | DE4025345A1 (en) |
DK (1) | DK0470467T3 (en) |
ES (1) | ES2061136T3 (en) |
ZA (1) | ZA916295B (en) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4216535A1 (en) * | 1991-08-21 | 1993-02-25 | Bayer Ag | FORMKOERPER FOR CONTROLLING SHAEDLINGEN |
ATE149286T1 (en) * | 1992-06-26 | 1997-03-15 | Sumitomo Chemical Co | CARRIER MATERIALS FOR INSECTICIDES |
US5632999A (en) * | 1993-08-18 | 1997-05-27 | Virbac, Inc. | Sustained release pyriproxifen compositions for parasite control |
AU700100B2 (en) * | 1995-07-10 | 1998-12-24 | Sumitomo Chemical Company, Limited | Resin composition and molded product thereof |
IE80657B1 (en) * | 1996-03-29 | 1998-11-04 | Merial Sas | Insecticidal combination to control mammal fleas in particular fleas on cats and dogs |
US6596291B2 (en) | 1997-12-05 | 2003-07-22 | Thomas A. Bell | Compositions and methods for treating surfaces infected with ectoparasitic insects |
JP2002193808A (en) * | 2000-12-26 | 2002-07-10 | Mitsubishi Chemicals Corp | Tool for controlling harmful life using pyrazole derivative |
DE10115225A1 (en) * | 2001-03-28 | 2002-12-19 | Bayer Ag | Molded articles containing active ingredients based on thermoplastically processable polyurethanes for combating parasites |
DE102004031325A1 (en) | 2004-06-29 | 2006-01-19 | Bayer Healthcare Ag | Active substance-containing solid shaped articles for external use against parasites on animals |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2715596C2 (en) | 1977-04-07 | 1986-04-30 | Bayer Ag, 5090 Leverkusen | Animal collars with insecticidal activity, process for their manufacture and their use |
FR2555408B2 (en) * | 1983-04-14 | 1986-11-21 | Rombi Max | INSECTICIDE NECKLACE AND MANUFACTURING METHOD THEREOF |
NZ221262A (en) | 1986-08-06 | 1990-08-28 | Ciba Geigy Ag | Preventing the reinfestation of dogs and cats by fleas by administering to the host a flea growth inhibiting substance orally, parenterally or by implant |
GB8809262D0 (en) | 1988-04-20 | 1988-05-25 | Secto Co Ltd | Devices for protecting animals from parasites |
DE4216535A1 (en) * | 1991-08-21 | 1993-02-25 | Bayer Ag | FORMKOERPER FOR CONTROLLING SHAEDLINGEN |
-
1990
- 1990-08-10 DE DE4025345A patent/DE4025345A1/en not_active Withdrawn
-
1991
- 1991-07-27 DE DE59102918T patent/DE59102918D1/en not_active Expired - Fee Related
- 1991-07-27 DK DK91112643.1T patent/DK0470467T3/en active
- 1991-07-27 ES ES91112643T patent/ES2061136T3/en not_active Expired - Lifetime
- 1991-07-27 AT AT91112643T patent/ATE111298T1/en not_active IP Right Cessation
- 1991-07-27 EP EP91112643A patent/EP0470467B1/en not_active Expired - Lifetime
- 1991-08-01 AU AU81534/91A patent/AU656141B2/en not_active Ceased
- 1991-08-05 JP JP3218066A patent/JPH04229125A/en active Pending
- 1991-08-07 CA CA002048543A patent/CA2048543C/en not_active Expired - Lifetime
- 1991-08-09 ZA ZA916295A patent/ZA916295B/en unknown
- 1991-08-09 KR KR1019910013736A patent/KR100202152B1/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
AU656141B2 (en) | 1995-01-27 |
ZA916295B (en) | 1992-05-27 |
EP0470467A2 (en) | 1992-02-12 |
AU8153491A (en) | 1992-02-13 |
DE59102918D1 (en) | 1994-10-20 |
ES2061136T3 (en) | 1994-12-01 |
ATE111298T1 (en) | 1994-09-15 |
JPH04229125A (en) | 1992-08-18 |
EP0470467B1 (en) | 1994-09-14 |
DE4025345A1 (en) | 1992-02-13 |
KR920003856A (en) | 1992-03-27 |
KR100202152B1 (en) | 1999-06-15 |
DK0470467T3 (en) | 1995-02-13 |
EP0470467A3 (en) | 1992-04-15 |
CA2048543A1 (en) | 1992-02-11 |
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