AU5766501A

AU5766501A - Pesticidal resin compositions

Info

Publication number: AU5766501A
Application number: AU57665/01A
Authority: AU
Inventors: Hiroki Nakata; Satoshi Sembo
Original assignee: Sumitomo Chemical Co Ltd
Current assignee: Sumitomo Chemical Co Ltd
Priority date: 2000-08-01
Filing date: 2001-07-26
Publication date: 2002-02-07
Also published as: FR2812519A1; ES2189657B1; BR0103324A; FR2812519B1; ITTO20010760A1; ZA200106205B; JP2002047110A; ES2189657A1

Description

S&FRef: 563171

AUSTRALIA

PATENTS ACT 1990 COMPLETE SPECIFICATION FOR A STANDARD PATENT

ORIGINAL

Name and Address of Applicant: Actual Inventor(s): Address for Service:

S

*5 S. Sumitomo Chemical Company, Limited 5-33, Kitahama 4-Chome Chuo-ku Osaka 541-8550 Japan Satoshi Sembo, Hiroki Nakata Spruson Ferguson St Martins Tower,Level 31 Market Street Sydney NSW 2000 (CCN 3710000177) Pesticidal Resin Compositions Invention Title: .S S S

S.

The following statement is a full description of this invention, including the best method of performing it known to me/us:- 5845c PESTICIDAL RESIN COMPOSITIONS Technical field of the invention The present invention relates to pesticidal resin compositions and methods of controlling pests.

Background of the Invention Various neonicotinoid compounds such as imidacloprid are well known as pesticidally active compounds.

USP 5,532,365 discloses as a pesticidal compound 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine. USP 5,532,365 discloses formulations of said pesticidal compound for uses in mass agriculture arts.

Animal collars in which a pesticidal compound, such as permethrin, phenothrin, diazinon, dichlorvos and propoxur, is supported on polyvinyl chloride have heretofore been commercially known. Polyvinyl chloride is, however, inappropriate for uses in such animal collars.

Summary of the Invention The present invention provides pesticidal resin compositions and methods of controlling pests.

Detailed description of the invention The pesticidal resin compositions of the present invention involve a polyolefin resin and a pesticidally active ingredient. The pesticidally active ingredient utilized in the present invention is 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine, which is disclosed in USP 5,532,365.

Examples of the polyolefin resin include an a -olefin homopolymer such as polyethylene and polypropylene; a -olefinic copolymers; copolymers composed of a cyclic olefm; copolymers ofethylene and a carbonate derivative having an ethylenically unsaturated bond such as ethylene-methyl methacrylate copolymer, ethylene-vinyl acetate copolymer, ethylene-acrylate copolymer and ethylene-vinyl acetate-methyl methacrylate copolymer and the like. The a -olefinic copolymers typically are composed of different olefm units, with more specific examples of such a -olefinic copolymers including a propylene-butene copolymer; an ethylene- a -olefin copolymer such as ethylene-propylene copolymer, ethylene-butene copolymer, ethylene-4-methyl-1-pentene copolymer and ethylene-hexene copolymer and the like.

Preferably, the pesticidal resin compositions utilize therein as the polyolefin resin, the polyethylene homopolymer or the ethylene- a -olefin copolymer. More preferably, such pesticidal resin compositions utilize therein as the ethylene- a -olefin copolymer, a low density a -olefinic copolymer. Typically, the polyolefin resin has at 190 0 C a melt flow rate of about 1 to 10 g/min, preferably about 1.5 g/min, when measured with the JIS K7210 method, which is well known.

The amount of the 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine ',present in the pesticidal resin compositions may vary with the use thereof, but can be, based on 100 parts by weight of the polyolefin resin, 0.001 to 100 parts by weight, and S* more preferably be 0.001 to 20 parts by weight.

Various plasticizers or softeners may also be added to pesticidal resin compositions, such as a plasticizer, a softener and the like. As the plasticizer, there is mentioned phthalate esters such as dioctyl phthalate, diisodecyl phthalate and diisoundecyl phthalate, trimellitate esters such as trioctyl trimellitate, tri-2-ethylhexyl trimellitate and tridecyl trimellitate; aliphatic diacidic esters such as dioctyl adipate, diisononyl adipate, diisodecyl adipate, dioctyl azelate and dioctyl sebacate; phosphate esters such as tricresyl phosphate and triphenyl phosphate; epoxy plasticizers such as epoxidized soybean oil, polyester plasticizers and the like; and as the softener, there is mentioned petroleum process oils, natural oils such as pine oil and the like.

When utilized, the amount of the plasticizer or softener present in the pesticidal resin compositions may be changed with the use thereof, but usually is, based on 100 parts by weight of the polyolefin resin, 120 parts by weight or less, and more preferably 100 parts by weight or less, and even more preferably 80 parts by weight or less.

Further, there may be optionally added to the pesticidal resin compositions, while in the range that the effect of the present invention is not eliminated, a stabilizer, antifoulant, pigments, dyestuffs, deodorants, aroma chemicals, incense, sticking agents, anti-corrosive agents, lubricants, anti-blocks surfactants and the like.

The pesticidal resin compositions, while in the range that the effect of the present invention is not eliminated, can also optionally added thereto other active ingredients, for example, other pesticidally active ingredients, pesticidally repellent ingredients, synergists, biocides/fungicides. As the other pesticidally active ingredients there is mentioned, for example, pyrethroid compounds such as allethrin, tetramethrin, prallethrin, phenothrin, resmethrin, cyphenothrin, permethrin, cypermethrin, °deltamethrin, tralomethrin, cyfluthrin, furamethrin, imiprothrin, etofenprox, fenvalerate, fenpropathrin, silafluofen, bifenthrin and transfluthrin; organophosphorous compounds such as dichlorvos, tetrachlorvinphos, fenthion, chlorpyrifos and diazinon; carbamate compounds such as propoxur, carbaryl, metoxadiazone and fenobucarb; chitin synthesis inhibitors such as lufenuron, chlorfluazuron, hexaflumuron, diflubenzuron, cyromazine, triflumuron, teflubenzuron, flufenoxuron, fluazuron, triazamate and 1 -(2,6-difluorobenzoyl)-3-[2-fluoro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl] urea; juvenile hormone analogues such as pyriproxyfen, methoprene, hydroprene and fenoxycarb; neonicotinoid compounds such as acetamiprid, nitenpyram, thiacloprid, thiamethoxam and derivatives; N-phenylpyrazole compounds and the like.

As a pesticidal repellent ingredient, for example, there is mentioned N,N-diethyl-m-toluamide, limonene, linalool, citronellol, menthol, menthone, hinokitiol, geraniol, eucalyptol, indoxacarb and carane-3,4-diol and the like.

As the synergist, for example, there is mentioned, for example, synergists such S. as PBO, S421, MGK264, IBTA and the like.

The pesticidal resin compositions can be produced by conventional methods, for example, by kneading 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine into the polyolefin resin. Such kneading is usually conducted by adding/kneading into the polyolefin resin in a kneading device, adding the 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine directly or as a dilution thereof in a plasticizer. As the kneading device, for example, there is mentioned a Banbury mixer, kneader, roll and the like.

The pesticidal resin compositions may then be shaped into a pesticidal article, if •so desired. The pesticidal article is typically produced from the pesticidal resin compositions by using conventional methods to mold resins. For example, the pesticidal resin compositions can be shaped to the desired form usually at an appropriate temperature in the range of 70 to 250 0 C by well-known forming methods such as extrusion forming, injection molding, blow molding, vacuum forming, pressure forming, casting molding, press molding, calendering, roll forming and the like.

The pesticidal articles produced from the pesticidal resin compositions can take various forms to control pests. Examples of such forms for the pesticidal articles include animal collars, eartags, medals, gloves, wall papers, floorings, agricultural films, nets, textiles, unwoven textiles, hoses, sheets, trays and the like.

The pesticidal resin compositions and the pesticidal articles are effective with various well known arthropods of agricultural pests, insanitary pests and animal pests.

Specifically, for example, there is mentioned Hemiptera: plant hoppers (Delphacidae) such as small brown plant hopper (Laodelphax striatellus), brown plant hopper (Nilaparvata lugens) and white-backed rice hopper (Sogatellafurifera); leafhoppers (Deltocephalidae) such as green rice leafhopper (Nephotettix cincticeps) and green rice leafhopper (Nephotettix virescens); aphids (Aphididae) such as cotton aphid (Aphis gossypii) and green peach aphid (Myzus persicae); plant bugs (Heteroptera) such as green rice bug (Nezara antennata) and bean bug (Riptortus clavetus); whiteflies (Aleyrodidae) such as greenhouse whitefly (Trialeurodes vaporariorum) and silverleaf whitefly (Bemisi argentifolii); scales such as Aonidiella aurantii, San Jose scale (Comstockaspis perniciosa), citrus snowscale (Unaspis citri), Ceroplastes rubens and Icerya purchasi; lace bugs (Tingidae), jumping plantlice (Psyllidae) and the like; Lepidoptera: Pyralidae such as rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis), cotton leaf roller (Notarcha derogata and Indian meal moth (Plodia interpunctella); Noctuidae such as tobacco cutworm (Spodoptera litura), rice armyworm (Pseudaletia separata), Trichoplusia sp, Heliothis sp. and Helicoverpa sp; sulfur butterflies (Pieridae) such as common cabbageworm (Pieris rapae crucivora); tortricids (Tortricidae) such as Adoxophyes sp., oriental fruit moth (Grapholita molesta) and Cydia pomonella; Carposinidae such as peach fruit moth (Carposina niponesnsis); Lyonetiidae such as Lyonetia sp.; tussock moths (Lymantriidae) such as Lymantria sp and Euproctis sp.; yponomeutids (Yponomeutidae) such as diamondback moth (Plutella xylostella); Gelechiidae such as Pectinophora gossypiela; Arctiidae such as Hyphantria cunea; clothes moths such as casemaking clothes moth (Tinea pellionella) and webbing clothes moth (Tineola bisselliella) and the like; Diptera mosquitoes (Culicidae) such as common mosquito (Culexpipiens pallens), Culex tritaeniorhynchus and Culex quinquefasciatus; Aedes sp. such as yellow fever mosquito (Aedes aegypti) and Aedes albopictus; Anopheles sp. such as Anopheles sinensis; Chironomidae (midges); muscid flies (Muscidae) such as housefly (Musca domestica) and false housefly (Muscina stabulans); blow flies (Calliphoridae); flesh flies (Sarcophagidae); little housefly (Fannia canicularis); Anthomyiidae such as seedcorn maggots (Delia platura) and onion maggot (Delia antiqua); fruit flies (Tephritidae); vinegar flies (Drosophilidae); moth flies (Psychodidae); black flies (Simuliidae); breeze flies (Tabanidae); stable flies (Stomoxyidae); laefminer flies (Agromyzidae) and the like; Beetles (Coleoptera): corn rootworms such as western corn rootworm (Diabrotica virgifera) and southern corn rootworm (Diabrotica undecimpunctata howardi); scarabs (Scarabaeidae) such as cupreous chafer (Anomala cuprea) and soybean beetle (Anomala rufocuprea); weevils (Curculionidae) such as maize weevil (Sitophilus zeamais), ricewater weevil (Lissorhoptrus oryzophilus) and adzuki bean weevil (Collosobruchus chinensis); Tenebrionidae (darkling beetles) such as yellow mealworm (Tenebrio molitor) and red flour beetle (Tribolium castaneum); leaf beetles (Chrysomelidae) such as cucurbit leaf beetle (Aulacophorafemoralis), striped flea beetle (Phyllotreta striolata) and Colorado beetle (Leptinotarsa decemlineata); deathwatch and drugstore beetle (Anobiidae); Epilachna sp. such as twenty-eight spotted ladybird (Epilachna vigintioctopunctata); powderpost beetle (Lyctidae); false powderpost beetles (Bostrychidae); longicorn beetles (Cerambycidae); robe beetle (Paederusfuscipes) and the like; Cockroaches (Blattidae): German cockroach (Blattella germanica); smokybrown cockroach (Periplaneta fuliginosa); American cockroach (Periplaneta americana); brown cockroach (Periplaneta brunnea), oriental cockroach (Blatta orientalis) and the like; Thrips (Thripidae): Thripspalmi and Thrips tabaci Hymenoptera: ants (Formicidae); hornets (Vespidae); Bethylid wasp (Bethylidae); sawflies (Tenthredinidae) such as Athaliajaponica and the like; Orthoptera: mole crickets (Gryllotalpidae); grasshoppers (Acrididae) and the like; Siphonaptera: cat flea (Ctenocephalidesfelis); dog flea (Ctenocephalides canis); human flea (Pulex irritans); oriental rat flea (Xenopsylla cheopsis) and the like; Lice (Anoplura): Pediculus humanus corporis; crab louse (Pthirus pubis); Haematopinus eursysternus; Daalmainia ovis and the like; Termites (Isoptera): Reticulitermes speratus; Formosan subterranean termite (Coptotermesformosanus) and the like; Mites and ticks (Acarina): spider mites (Tetranychidae) such as Tetranychus urticae (two-spotted spider mite), citrus red mite (Panonychus citri) and Orgonicus sp.; Eriophyidae such as Aculops pelekassi; Tarsonemidae such as broad mite (Polyphagotarsonemus lactus); Tenuipalpidae; Tuckerellidae; Ixodidae such as Haemaphysalis longicornis, Haemaphysalisflava, Dermacentor taiwanicus, Ixodes ovatus, Ixodes persulcatus and Boophilus microplus; acarid mites (Acaridae) such as mold mite (Tyrophagus putrescentiae); Dermanyssidae such as American house dust mite (Dermatophagoides farinae) and Dermatophagoides pteronyssinus; Cheyletidae such as Cheyletus eruditus, Chelacaropsis malaccensis and Cheyletus moorei; Dermanyssus sp and the like; Nematoda: coffee root-lesion nematode (Pratylenchus coffeae); Pratylenchus fallax; soybean cyst nematode (Heterodera glycines); potato cyst nematode (Globodera rostochiensis); northern root-knot nematode (Meloidogyne hapla) and the like; Spiders: Chiracanthiumjaponicum; Latrodectus hasseltii and the like; Chilopoda: Thereuonema hilgendorfi; Scolopendra subspinipes and the like; Diplopoda: hot house millipede (Oxidus gracilis); Nedyopus tambanus and the like; Pill bugs (Isopoda): pill bug (Armadillidium vulgare) and the like; Gastropoda: tree slug (Limax marginatus); yellow slug (Limaxflavus) and the like.

It is preferable to use the pesticidal resin compositions to control household pests such as flies, mosquitoes, cockroaches, ticks, fleas, lice, termites and the like.

For example, when controlling animal ectoparasites, the pesticidal resin compositions may be formed into animal collars, animal eartags and the like. When controlling cockroaches, mites, ticks, ants or thrips, the pesticidal resin compositions may be formed into a pesticidal sheets. When repelling aviator pests such as flies, mosquitoes and the like, the pesticidal resin compositions may be formed into pesticidal strings, such that the strings are formed into a pesticidal screen net.

To provide an effective residual control of the pests, the pesticidal resin composition is applied to an area of where pests inhabit. In such cases, the pesticidal resin composition is applied such that 0.1 mg to 400 mg of 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine is utilized to control 1cm 3 for 1 to 10000 days.

When utilizing as the animal collar, ectoparasites such as fleas can be controlled by fastening the animal collar at the neck area of the animal such as a dog, cat and the like. In such cases, the pesticidal resin compositions are formed to have a width of about 1 to 2cm and a length which is greater than the circumference of the neck of the animal.

When utilizing as the animal eartag, ectoparasites such as flies and breeze flies can be controlled by fastening to the ear of the animal such as a cow, a plate molding of the pesticidal articles, which has a surface area of about 10 to 200cm 2 When utilizing as the pesticidal sheet, household pests such as cockroaches can be controlled by spreading onto the kitchen floor area, the plate form or film form of the *sea pesticidal article, which has been cut to an appropriate size.

Further, when utilizing as the pesticidal sheet, the termites can be prevented from infesting a house by spreading and clogging openings at under the house floor with the plate form or film form of the pesticidal article that has been cut to an appropriate size.

When utilizing as said pesticidal screen net, mosquitoes can be prevented from infesting a house, by producing the pesticidal resin compositions into a string form, forming the string form into a screen net of a screen door or a Japanese mosquito net and using the screen net as such.

Examples Formulation Example 1 Five grams of 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine is added to ultra low density polyethylene (Sumitomo Chemical Company, EXCELLEN EUL430; melt flow rate at 190°C of 4.0g/min.) to provide a mixture of 100g. Using a plastograph, the mixture was melt kneaded for 5 minutes under the conditions 150°C and 50rpm, to produce a pesticidal resin composition. The pesticidal resin composition is press molded at 150C for 10 minutes, to produce a 1mm thick sheet (formulation 1).

Formulation Example 2 Ten (10) grams of 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and 3990g of ultra low density (Sumitomo Chemical Company, SUMIKATHENE F208-1; melt flow rate at 190 0 C of 1.5 g/min.) was kneaded for 10 minutes with a Bunbary mixer (Nippon Roll MFG. Co., LTD) to produce a master batch of 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine. A 5 fold dilution of the master batch with the above polyethylene was then produced. The dilution above was then utilized to produce a pesticidal film having a thickness of 180im at a resin temperature of 180 0 C with an air-cooled inflation film-forming machine equipped with a circular die. (formulation 2).

Comparative Example 1 Twenty-one (21) grams of di-n-butyl adipate, 9.1 g diethylhexyl phthalate and 2.3g of epoxydated soybean oil are mixed with 10.0g of 1-methyl-2-nitro-3-[(3-tetrahydrofuryl)methyl]guanidine and 56.7g ofpoly(vinyl chloride) (Shin Dai-Ichi Vinylchloride Corporation, product name: ZEST 1300Z) to provide a mixture of 100g. Using a plastograph, the mixture was melt kneaded for minutes under the conditions 150°C and 50rpm, to produce a comparative resin composition. The comparative resin composition was press molded at 150 0 C for minutes to produce a lmm thick sheet (comparative formulation 1).

Comparative Example 2 Using only the ultra low density polyethylene identical to Example 2, a film having a thickness of 180gm was produced by a method similar to Example 2 (formulation 2).

Test Example 1 After the surface of formulation 1 produced in Formulation Example 1 was •wiped 5 times with a laboratory paper towel, formulation 1 was preserved at room •temperature (25 29C). Subsequently, the wiping treatment of the rein surface Sprocedure was continuously conducted every 2 to 3 days for 86 days.

•After said 86 days of wiping treatment, 10 adult common mosquitoes were anesthetized with carbon dioxide and were placed on the surface of formulation 1. A ••plastic cover having a 3cm diameter and a height of 1 cm was placed thereon to force the adult common mosquitoes to be in contact with the resin surface. After 1 hour, all of the adult common mosquitoes were anesthetized and transferred to a sanitary container.

Food sugar water) was provided to adult common mosquitoes and the mortality was examined the next day.

Further, the surface of comparative formulation 1 produced in Comparative Example 1 had conducted the 86 day continuous wiping treatment as similar to formulation 1 above and the mortality effect on the common mosquitoes was examined by a similar method.

Table 1 Concentration of Adult common pesticidally active mosquito mortality ingredient Resin Polyethylene formulation 1 5.0 copolymer Comparative formulation 1 10.0 vinyl chloride Test Example 2 Formulation 1 in which the surface thereof was wipe treated for 86 days as similar to Test Example 1 was cut to a width of 1 cm and length of 15cm. After the cut formulation 1 was fastened onto the inner surface of a commercially available flea repellent collar cover (containing no pesticidally active ingredient), that was fastened at the neck area of a cat (of a weight of 3kg). Two weeks after fastening, the cat was infested with 30 adult cat fleas. Ten (10) days after infestation, the total number of infested fleas was examined by using a flea removal comb.

Further, comparative formulation 1, in which the surface thereof was wipe treated for 86 days as similar to Test Example 1, was fastened to the cat as similar to the above, and the number of infested fleas was examined.

The experiment was repeated once. The results are shown in Table 2.

Table 2 CC Table 2 Concentration of pesticidally active ingredient Resin cat flea infestation Polyethylene formulation 1 5.0 Hetercompolymer 4 comparative formulation 1 10.0 vinyl chloride 19 [0050] Test Example 3 Soil was added to the bottom of a 8L plastic bucket and the 8L plastic bucket was infested with 500 termites. After adding a little water, a concrete block having a length of 10cm, width of 6cm, height of 10 was placed onto the soil in the 8L plastic bucket. The film of formulation 1 or the film of comparative formulation 2 was then cut to a thickness of about 7cm. At the portion 3cm higher than the soil surface, the film of formulation 1 or comparative formulation 2 was attached to the concrete block at each of the 4 vertical surfaces of the concrete block, such that the film covered the upper portion of the 4 vertical surfaces thereof. Timber food was placed on top of the concrete block. A month thereafter, the mortality of the termites, the presence of feed harm on said sheet and the presence of formed termite pathways on the concrete block surface was examined.

T Table 3 .999..

9 *99. oo9o..

9.

oo o o 99 9o oooo •go• *.:99 9e feed harm on formation of sheet pathways mortality of termites formulation 1 None none mostly terminated comparative formulation 2 Present present many alive The examples above evidence that the pesticidal resin compositions of the present invention provide an excellent pesticidal effect with pests which is stabily set forth for an extended period of time.

Claims

2. The pesticidal molding according to claim I, wherein said pesticidal resin composition is used for an animal collar.
3. The pesticidal resin composition according to claim I, wherein said pesticidal resin composition is used for an eartag.
4. The pesticidal resin composition according to claim I, wherein said pesticidal rI-esin composition is used for a pesticidal sheet. The pesticidal resin composition according to any one of claims I to 4, wherein the polyolefin resin is an ethylene-a-olefin heterocopolymer.
6. A method of controlling pests, wherein the pesticidal composition of any one of claims I to 5 is applied to an area where pests inhabit.
7. A pesticidal resin composition, substantially as hereinbefore described with i referece to any one of the examples but excluding any comparative examples.
8. A pesticidal resin composition according to any one of claims I to 5 or 7 \when used for controlling pests. Dated 19 July, 2001 Sumitomo Chemical Company, Limited Patent Attorneys for the Applicant/Nominated Person SPRUSON FERGUSON as%* .0 0000 00* S L 0 OS S [R:\LIBFF]02820.doc:aak