US20050234070A1 - Agents for preserving technical materials against insects - Google Patents
Agents for preserving technical materials against insects Download PDFInfo
- Publication number
- US20050234070A1 US20050234070A1 US11/146,800 US14680005A US2005234070A1 US 20050234070 A1 US20050234070 A1 US 20050234070A1 US 14680005 A US14680005 A US 14680005A US 2005234070 A1 US2005234070 A1 US 2005234070A1
- Authority
- US
- United States
- Prior art keywords
- weight
- parts
- triazole
- soil
- chloro
- 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.)
- Abandoned
Links
- 239000000463 material Substances 0.000 title claims abstract description 27
- 241000238631 Hexapoda Species 0.000 title abstract description 16
- 239000000203 mixture Substances 0.000 claims description 28
- 239000002023 wood Substances 0.000 claims description 25
- -1 2-chloro-5-pyridyl Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 239000002917 insecticide Substances 0.000 claims description 15
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 13
- 239000002689 soil Substances 0.000 claims description 12
- 239000000417 fungicide Substances 0.000 claims description 6
- 239000002131 composite material Substances 0.000 claims description 5
- 230000000855 fungicidal effect Effects 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000010985 leather Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims description 4
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 claims description 4
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 claims description 3
- 229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 claims description 3
- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- AKNQMEBLVAMSNZ-UHFFFAOYSA-N azaconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCCO1 AKNQMEBLVAMSNZ-UHFFFAOYSA-N 0.000 claims description 3
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 claims description 3
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- VAFVPAKNJFBOFX-HKIWRJGFSA-M (z)-octadec-9-enoate;tributylstannanylium Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)O[Sn](CCCC)(CCCC)CCCC VAFVPAKNJFBOFX-HKIWRJGFSA-M 0.000 claims description 2
- RULKYXXCCZZKDZ-UHFFFAOYSA-N 2,3,4,5-tetrachlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C(Cl)=C1Cl RULKYXXCCZZKDZ-UHFFFAOYSA-N 0.000 claims description 2
- AVGVFDSUDIUXEU-UHFFFAOYSA-N 2-octyl-1,2-thiazolidin-3-one Chemical compound CCCCCCCCN1SCCC1=O AVGVFDSUDIUXEU-UHFFFAOYSA-N 0.000 claims description 2
- CXIVKQSIEXBSRQ-UHFFFAOYSA-N 4,5-dichloro-2-octyl-1,2-thiazolidin-3-one Chemical compound CCCCCCCCN1SC(Cl)C(Cl)C1=O CXIVKQSIEXBSRQ-UHFFFAOYSA-N 0.000 claims description 2
- CDIJOYCNNFLOAX-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical compound ClC(Cl)(Cl)SC1=CC=CC2=C1C(=O)NC2=O CDIJOYCNNFLOAX-UHFFFAOYSA-N 0.000 claims description 2
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- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 claims description 2
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- NMCCNOZOBBWFMN-UHFFFAOYSA-N davicil Chemical compound CS(=O)(=O)C1=C(Cl)C(Cl)=NC(Cl)=C1Cl NMCCNOZOBBWFMN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 claims description 2
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- 239000010452 phosphate Substances 0.000 claims description 2
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 claims description 2
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- 239000004753 textile Substances 0.000 claims description 2
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 claims description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 2
- 229910001887 tin oxide Inorganic materials 0.000 claims description 2
- JUEAPPHORMOWPK-UHFFFAOYSA-M tributylstannyl benzoate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)C1=CC=CC=C1 JUEAPPHORMOWPK-UHFFFAOYSA-M 0.000 claims description 2
- 239000004557 technical material Substances 0.000 claims 4
- OCNIQFDCKLHNCQ-UHFFFAOYSA-N 2,4,5-tribromo-3-iodophenol Chemical compound OC1=CC(Br)=C(Br)C(I)=C1Br OCNIQFDCKLHNCQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 150000003751 zinc Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 36
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- 238000012360 testing method Methods 0.000 description 12
- 238000009472 formulation Methods 0.000 description 9
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- 239000005906 Imidacloprid Substances 0.000 description 8
- 229940056881 imidacloprid Drugs 0.000 description 8
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- 231100000331 toxic Toxicity 0.000 description 7
- 230000002588 toxic effect Effects 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 6
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Classifications
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- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
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- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/343—Heterocyclic compounds
Definitions
- the present invention relates to the use of known nitromethylene or nitroimino compounds as agents for combating technical materials destroying insects in order to preserve these materials.
- the present invention also relates to compositions useful for combating these insects, preserving technical materials completely, i.e. not only against insects but also against fungi, bacteriae and algae and for treating soil to protect technical materials against termite infestations.
- the invention furthermore relates to processes for treating technical materials and for soil treatment against termite infestations.
- Insecticidal agents and compositions of said compounds and their use to preserve technical materials completely and to treat soil against termite infestations have not been known up to now.
- insects are known as pests infesting technical materials so that due to serious damages caused thereby undesirable effects on living environment and cultural assets principally made of these materials have posed a social problem, urgently requiring effective controlling of the pests.
- Termites are known as important examples of these pests.
- organophosphorus insecticides such as phoxim [0-( ⁇ -cyanobenzylideneamino)0,0-diethylphosphorothioate], chloropyriphos [0,0-diethyl-3,5,6-trichloro-2-pyridylphosphorothioate], etc., as well as pyrethroides series insecticides such as permethrin [5-benzyl-3-furylmethyl-3-(2-methoxy-carbonyl-1-propenyl)-2,2-dimethylcyclopropane carboxylate], decamethrin [ ⁇ -cyano-3-phenoxybenzyl d,l-cis-3-(2,2-dibromovinyl)-2,2-dimethyl cyclopropane carboxylate], cypermethrin [ ⁇ -cyano-3-phenoxybenzyl ( ⁇ ) cis, trans-3-(2,2-dichloroviny
- X is NH or S
- Y is CH or N
- Z is 2-chloro-5-pyridyl or 2-chloro-5-thiazolyl
- R 1 is hydrogen or methyl
- n 0 or 1
- the compounds according to the invention of the formula (I) surprisingly exhibit an extremely strong insecticidal action on material destroying insects and the function is substantially superior to that of known insecticidal agents.
- the compounds of the formula (I) can be used to preserve technical materials against insects.
- X is NH or S
- Y is CH or N
- R 1 is hydrogen
- n 0 or 1.
- the active substances to be used according to the invention exhibit powerful insecticidal effects against material destroying insects.
- They can therefore be used in insecticidal agents for combating material destroying insects and preserving technical materials. They can also be used for soil treatment against termite infestation.
- wood or composite wood-materials such as pressed wood, particle board, chip board, wafer board, plywood, wood laminated material, freshly cut timber/lumber etc.
- paper leather or leather products, natural or synthetic polymers, textiles.
- Preferable materials are wood or composite wood-materials.
- insects to be combated or controled by the active substances of formula (I) according to the present invention the following ones can be mentioned:
- Kalotermitidae such as Kalotermes spp. Cryptotermes spp. etc.
- Termopsidae such as Zootermopsis spp. etc.
- Rhinotermitidae such as Reticulitermes spp. Heterotermes spp. Coptotermes spp. etc.
- Termitidae such as Amitermes spp. Nasutitermes spp. Acanthotermes spp. Mikrotermes spp. etc.
- the active compounds of the general formula (I) in the present invention can be prepared into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active compounds, and micro-capsules.
- formulations may be produced in a known manner, for example, by mixing the active compounds with extenders, that is to say liquid or liquefied gaseous or solid diluents or carriers, optionally with the use of surface-active agents, that is to say emulsifying agents, dispersing agents, and/or foam-forming agents.
- extenders that is to say liquid or liquefied gaseous or solid diluents or carriers
- surface-active agents that is to say emulsifying agents, dispersing agents, and/or foam-forming agents.
- organic solvents can, for example, also be used as auxiliary solvents.
- liquid diluents or carriers can be mentioned, for example, aromatic hydrocarbons, such as xylene, toluene and alkyl naphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes and methylene chloride, aliphatic or alicyclic hydrocarbons, such as cyclohexane or paraffins, for example, mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethylformamide and dimethylsulfoxide, as well as water.
- aromatic hydrocarbons such as xylene, toluene and alkyl naphthalenes
- chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chloro
- liquefied gaseous diluents or carriers liquids which are gaseous at normal temperature and under normal pressure, for example, aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
- ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceus earth
- ground synthetic minerals such as highly-dispersed silicic acid, alumina and silicates.
- solid carriers for granules there may be used crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks.
- crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite
- synthetic granules of inorganic and organic meals such as sawdust, coconut shells, maize cobs and tobacco stalks.
- nonionic and ionic emulsifiers such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example, alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates as well as albumin hydrolysis products.
- Dispersing agents include, for example, lignin sulfite waste liquors and methyl cellulose.
- Adhesives such as carboxymethyl cellulose and natural and synthetic polymers, (such as gum arabic, polyvinyl alcohol and polyvinyl acetate) can be used in the formulations in the form of powders, granules or emulsifiable concentrations.
- colorants such as inorganic pigments, for example, iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs or metal phthalo-cyanine dyestuffs, and trace elements, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
- organic dyestuffs such as alizarin dyestuffs, azo dyestuffs or metal phthalo-cyanine dyestuffs
- trace elements such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
- the formulations in general, contain from 0.001 to 95 percent by weight of active compound, preferably from 0.5 to 90 percent by weight.
- the active compound of the present invention having the formula (I) can be present as a mixture with a synergist in a formulation or a use form, of the type that is commercially useful.
- the term “synergist” denotes a compound which is not active in itself, but promotes the action of an active compound.
- the content of the active compounds having the general formula (I) of the present invention in commercially useful formulations can vary within a wide range.
- the active compound concentration of the formulation for use is, for example, from 0.0000001 to 100 percent by weight, preferably from 0.0001 to 1 percent by weight.
- compositions containing at least one insecticidally active compound of the formula (I) and at least one biological active fungicide, bactericide or algizide can be treated with compositions containing at least one insecticidally active compound of the formula (I) and at least one biological active fungicide, bactericide or algizide.
- Wood or composite wood-materials can preferably be treated with a composition containing
- Nitriles such as
- Wood-discoloring fungi such as
- Wood-destroying fungi such as
- compositions also will include at least one additional diluent, emulsifier, melting agent, organic binding agent, auxiliary solvents, processing additives, fixatives, plasticizers, UV-stabilizers or stability enhancers, dyes (water soluble, water insoluble), color pigments, siccatives, corrosion inhibitors, antisettlement agents, additional insecticides (such as insecticidal carbamates, organophosphorus compounds, halogenated hydrocarbons, pyrethroides etc.), anti skinning aqents and the like.
- additional diluent such as insecticidal carbamates, organophosphorus compounds, halogenated hydrocarbons, pyrethroides etc.
- compositions according to the present invention generally comprise from about 10 ⁇ 6 to 30 parts by weight, preferably from about 0.0005 to 15 parts by weight and more preferably from 0.005 to 2 parts by weight of the insecticide of formula (I) and from 0.01 to 90 parts by weight, preferably from about 0.05 to 50 parts by weight and more preferably from 0.1 to 30 parts by weight of at least one of the above-mentioned fungicides.
- compositions can be provided as ready for use products or as concentrates, which have to be diluted prior to use.
- compositions can be applied by means of brushing, spraying, dipping, double vacuum and the like as known in the art.
- the compositions can be prepared by any technique known in the art.
- Emulsifier 1 part by weight of polyoxyethylene-alkylphenyl-ether
- the index of xylophagous damage observed on the test blocks 0 No damage 0.5
- More than three deep damages 4 Evidently damaged zone covering up to about one third of the whole surface area of the block 5
- the toxicity against larvae of Hylotorupes bajulus, using wood samples treated with the active compound I.3 provided in Example 8 in chloroform having concentrations of 1.44 ⁇ 10 ⁇ 5 %, 1.44 ⁇ 10 ⁇ 4 %, 7.2 ⁇ 10 ⁇ 3 %, and 1.44 ⁇ 10 ⁇ 2 % was determined according to the detailed description of DIN EN 47 (edition 1990, Beuth Verlag GMBH) which is concerned with the European standard method prescribed by the European Committee for standardization concerning wood preservatives, determination of the toxic value against larvae of Hylotrupes bajulus.
- the Toxic threshold value was between 1.08 g/m 3 and 10.8 g/m 3 of the active compound I.3.
- Example 10 The same three wood-samples with impregnation treatment in vacuum as in Example 10 are provided.
- the toxic threshold value was between 0.135 g/m 3 and 1.344 g/m 3 of the active compound I.3.
Abstract
Description
- The present invention relates to the use of known nitromethylene or nitroimino compounds as agents for combating technical materials destroying insects in order to preserve these materials.
- The present invention also relates to compositions useful for combating these insects, preserving technical materials completely, i.e. not only against insects but also against fungi, bacteriae and algae and for treating soil to protect technical materials against termite infestations.
- The invention furthermore relates to processes for treating technical materials and for soil treatment against termite infestations.
- The compounds and their insecticidal use in the field of plant protection has already been known. Compare for example with EP-A 163855 and EP-A 192060.
- Insecticidal agents and compositions of said compounds and their use to preserve technical materials completely and to treat soil against termite infestations have not been known up to now.
- Different insects are known as pests infesting technical materials so that due to serious damages caused thereby undesirable effects on living environment and cultural assets principally made of these materials have posed a social problem, urgently requiring effective controlling of the pests. Termites are known as important examples of these pests.
- At present, use for combating technical materials destroying insects has been made of organophosphorus insecticides such as phoxim [0-(α-cyanobenzylideneamino)0,0-diethylphosphorothioate], chloropyriphos [0,0-diethyl-3,5,6-trichloro-2-pyridylphosphorothioate], etc., as well as pyrethroides series insecticides such as permethrin [5-benzyl-3-furylmethyl-3-(2-methoxy-carbonyl-1-propenyl)-2,2-dimethylcyclopropane carboxylate], decamethrin [α-cyano-3-phenoxybenzyl d,l-cis-3-(2,2-dibromovinyl)-2,2-dimethyl cyclopropane carboxylate], cypermethrin [α-cyano-3-phenoxybenzyl (±) cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], fenvalerate [(RS)-α-cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbutyrate], cyflutrine [cyano-(4-fluoro-3-phenoxyphenyl) methyl-3-(2,2-dichloroethenyl)-2,2-dimethyl-cyclopropane carboxylate].
- However, the above-mentioned insecticides are unsatisfactory as far as effective concentration and the long lasting effect are concerned.
-
- X is NH or S,
- Y is CH or N
- Z is 2-chloro-5-pyridyl or 2-chloro-5-thiazolyl,
- R1 is hydrogen or methyl, and
- n is 0 or 1,
- exhibit powerful insecticidal properties on material destroying insects and preferably on termites.
- The compounds according to the invention of the formula (I) surprisingly exhibit an extremely strong insecticidal action on material destroying insects and the function is substantially superior to that of known insecticidal agents.
- The compounds of the formula (I) can be used to preserve technical materials against insects.
- In the formula (I), the individual residues have the following preferable meanings:
- X is NH or S,
- Y is CH or N,
- Z is 2-chloro-5-pyridyl,
- R1 is hydrogen, and
- n is 0 or 1.
- As examples of the active substances to be used according to the invention, the following ones are particularly preferred:
- 1-(6-chloro-3-pyridylmethyl)-2-nitromethylene-imidazolidine,
- 3-(6-chloro-3-pyridylmethyl)-2-nitromethylene-thiazolidine,
- 1-(6-chloro-3-pyridylmethyl)-2-nitroimino-imidazolidine,
- 1-(6-chloro-3-pyridylmethyl)-2-nitromethylene-tetrahydropyrimidine, and
- 3-(6-chloro-3-pyridylmethyl)-2-nitromethylene-tetrahydro-2H-1,3-thiazine.
- The active substances to be used according to the invention exhibit powerful insecticidal effects against material destroying insects.
- They can therefore be used in insecticidal agents for combating material destroying insects and preserving technical materials. They can also be used for soil treatment against termite infestation.
- As individual examples of technical materials preserved by means of the insecticidal agents according to the present invention the following ones can be mentioned: wood or composite wood-materials (such as pressed wood, particle board, chip board, wafer board, plywood, wood laminated material, freshly cut timber/lumber etc.), paper, leather or leather products, natural or synthetic polymers, textiles.
- Preferable materials are wood or composite wood-materials.
- As individual examples of insects to be combated or controled by the active substances of formula (I) according to the present invention the following ones can be mentioned:
- Order Isoptera
Mastotermitidae Kalotermitidae such as Kalotermes spp. Cryptotermes spp. etc. Termopsidae such as Zootermopsis spp. etc. Rhinotermitidae such as Reticulitermes spp. Heterotermes spp. Coptotermes spp. etc. Termitidae such as Amitermes spp. Nasutitermes spp. Acanthotermes spp. Mikrotermes spp. etc. - Order Coleoptera
Lyctidae such as Lyctus brunneus etc. Bostrychidae such as Bostrychus capucinus Dinoderus minutus etc. Anobiidae such as Anobium punctatum Xyletinus peltatus Xestobium rufovillosum Ptilinus pectinicomis etc. Cerambycidae such as Hylotrupes bajulus Hesperophanus cinereus Stromatium fulvum Chlorophorus pilosus etc. Oedemeridae Serropulpidae Curculionidae Seolytida Platypodidae - Order Hymenoptera
Siricidae such as Sirex spp. Urocerus spp. Formicidae such as Camponotus spp. - In the above Isopterous insects, especially, there may be mentioned as examples of termites in Japan:
- Deucotermes speratus,
- Coptotermes formosanus,
- Glyptotermes fucus,
- Glyptotermes satsumensis,
- Glyptotermes nakajimai,
- Glyptotermes Kodamai,
- Incisitermes minor,
- Neotermes koshunensis,
- Cryptotermes domesticus,
- Hodotermopsis japonica,
- Reticulitermes miyatakei,
- Odontotermes formosanus,
- Nasutitermes takasagoensis,
- Capritermes nitobei and so on.
- The active compounds of the general formula (I) in the present invention can be prepared into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active compounds, and micro-capsules.
- These formulations may be produced in a known manner, for example, by mixing the active compounds with extenders, that is to say liquid or liquefied gaseous or solid diluents or carriers, optionally with the use of surface-active agents, that is to say emulsifying agents, dispersing agents, and/or foam-forming agents. In the case of using water as an extender, organic solvents can, for example, also be used as auxiliary solvents.
- As liquid diluents or carriers can be mentioned, for example, aromatic hydrocarbons, such as xylene, toluene and alkyl naphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes and methylene chloride, aliphatic or alicyclic hydrocarbons, such as cyclohexane or paraffins, for example, mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethylformamide and dimethylsulfoxide, as well as water.
- By liquefied gaseous diluents or carriers are meant liquids which are gaseous at normal temperature and under normal pressure, for example, aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
- As solid diluents there may be used ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceus earth, and ground synthetic minerals, such as highly-dispersed silicic acid, alumina and silicates.
- As solid carriers for granules there may be used crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks.
- As emulsifying and/or foam-forming agents there may be used nonionic and ionic emulsifiers, such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example, alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates as well as albumin hydrolysis products. Dispersing agents include, for example, lignin sulfite waste liquors and methyl cellulose.
- Adhesives such as carboxymethyl cellulose and natural and synthetic polymers, (such as gum arabic, polyvinyl alcohol and polyvinyl acetate) can be used in the formulations in the form of powders, granules or emulsifiable concentrations.
- It is possible to use colorants such as inorganic pigments, for example, iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs or metal phthalo-cyanine dyestuffs, and trace elements, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
- The formulations, in general, contain from 0.001 to 95 percent by weight of active compound, preferably from 0.5 to 90 percent by weight.
- Furthermore, the active compound of the present invention having the formula (I) can be present as a mixture with a synergist in a formulation or a use form, of the type that is commercially useful. The term “synergist” denotes a compound which is not active in itself, but promotes the action of an active compound. The content of the active compounds having the general formula (I) of the present invention in commercially useful formulations can vary within a wide range. The active compound concentration of the formulation for use is, for example, from 0.0000001 to 100 percent by weight, preferably from 0.0001 to 1 percent by weight.
- In order to protect the above-mentioned materials completely, i.e. not only against material destroying insects but also against fungi, bacteria and algae, they can be treated with compositions containing at least one insecticidally active compound of the formula (I) and at least one biological active fungicide, bactericide or algizide.
- Wood or composite wood-materials can preferably be treated with a composition containing
- a) an insecticidally effective amount of a compound of the formula (I) or mixtures thereof and
- b) a fungicidally effective amount of at least one compound selected from the group of
- Trihalosulfenyl-Compounds such as
- N-Dichlorofluoromethylthio-N′,N′-dimethyl-N-phenyl-sulfuric acid diamide (Dichlofluanide)
- N-Dichlorofluoromethylthio-N′,N′-dimethyl-N-p-toluylsulphamide (Tolylfluanide)
- N-Trichloromethylthiophthalimide (Folpet)
- N-Dichlorofluoromethylthiophthalimide (Fluorfolpet) etc.
- Iodine-Compounds such as
- 3-Iodo-2-propynyl-butylcarbamate (IPBC)
- 3-Iodo-2-propynyl-hexylcarbamate
- 3-Iodo-2-propynyl-cyclohexylcarbamate
- 3-Iodo-2-propynyl-phenylcarbamate
- Diiodmethyl-p-tolylsulphone (Amical 48) etc.
- Phenols such as
- ortho-Phenylphenol
- Tribromophenol
- Tetrachlorophenol
- Pentachlorophenol etc.
- Azole-Compounds such as
- 1-(4-Chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4 triazol-1-yl)-2-butanone (Triadimefon)
- β-(4-Chlorophenoxy)-α-(1,1 dimethyl-ethyl)-1H-1,2,4 triazole-1-ethanol (Triadimenol)
- ±α[2-(4-chlorophenyl) ethyl]-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol (Tebuconazole)
- 1-[2(2,4-dichlorophenyl) 4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (Propiconazol)
- 1-[2(2,4-dichlorophenyl)-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (Azaconazol)
- (RS)-2(2,4-dichlorophenyl)-1-(1H-1,2,4 triazol-2-yl)-2-ol (Hexaconazol)
- 1-N-propyl-N-[2-(2,4,6-trichlorophenoxy) ethyl] carbamoylimidazol (Prochloraz) etc.
- Tin Compounds such as
- Tributyl tin octoate
- Tributyl tin oleate
- Bistributyl tin oxide
- Tributyl tin naphthenate
- Tributyl tin phosphate
- Tributyl tin benzoate etc.
- Thiocyanate Compounds such as
- Methylenebisthiocyanate (MBT)
- 2-Thiocyanomethylthiobenzothiazole (TCMTB) etc.
- Quarternary Ammonium Compounds such as
- Benzyl-dimethyl-tetradecylammoniumchloride
- Benzyl-dimethyl-dodecylammoniumchloride etc.
- Benzimidazole Compounds such as
- 2-(2′-Furyl)-1H-benzimidazole (Fuberidazole)
- Methylbenzimidazol-2-ylcarbamate (BCM)
- 2-(41-thiazolyl) benzimidazole (Thiabendazole)
- Methyl (1-butylcarbamoyl)-2-benzimidazole carbamate (Benomyl)
- Isothiazolinone Compounds such as
- N-Methylisothiazolin-3-one
- 5-Chloro-N-methylisothiazolin-3-one
- 4,5-Dichloro-N-octylisothiazolin-3-one
- N-Octylisothiazolin-3-one
- Morpholine Compounds such as
- C14-C11-4-Alkyl-2,6-dimethylmorpholine (Tridemorph)
- Pyridine Compounds such as
- 1-Hydroxy-2-pyridine-thione and Sodium Iron, Manganese or Zinc-Salt thereof
- Tetrachloro-4-methyl sulphonyl pyridine
- N-Cyclohexyldiaziniumdioxy Compounds such as
- Tris-(N-cyclohexyldiaziniumdioxy) aluminium
- Bis-(N-cyclohexyldiaziniumdioxy) copper
- Naphthenate Compounds such as
- Zincnaphthenate
- Quinoline Compounds such as the copper salt of
- 8-hydroxy-quinoline
- Nitriles such as
- 1,2,3,5-Tetrachloro-4,6-cyanobenzene.
- Boric compounds such as boric acid, borax, borates
- Ureas such as N′(3,4-dichlorophenyl)-N,N-dimethylurea
- Furane derivatives such as Furmecyclox
- These fungicidally effective compounds are added to the composition in order to prevent wood or wood materials not only against wood destroying insects but also against
- Wood-discoloring fungi such as
-
- Ascomycetes (Caratocystis minor)
- Deuteromycetes (Aspergillus niger, Aureobasidium pullulans, Dactyleum fusarioides, Penicillium Variabile, Sclerophoma pithyophila, Scopularia phycomyces, Trichoderma viride, Trichoderma liguorum)
- Zygomycetes (Mucor spinosus)
and/or
- Wood-destroying fungi such as
-
- Ascomycets (Chetomium alba-arenulum, Chaetonium globosum, Humicola grisea, Petriella setifera, Trichurus spiralis)
- Basidiomycetes
- (Coniophera puteana
- Coriolus versicolor
- Donbiopora expansa
- Glenospora graphii
- Gloeophyllum abietinum
- Gloeophyllum adoratum
- Gloeophyllum protactum
- Gloeophyllum trabeum
- Gloeophyllum sepiarium
- Lentinus cyathioformes
- Lentinus edodes
- Lentinus lepideus
- Lentinus squavrolosus
- Paxillus panuoides
- Pleurofus ostreatus
- Poria placenta
- Poria monticola
- Poria vaillantii
- Poria vaporia
- Serpula himantoides
- Serpula lacrymans
- Tyromyces palustris)
- Deuteromycetes (Cladosporium herbarum).
- Generally the compositions also will include at least one additional diluent, emulsifier, melting agent, organic binding agent, auxiliary solvents, processing additives, fixatives, plasticizers, UV-stabilizers or stability enhancers, dyes (water soluble, water insoluble), color pigments, siccatives, corrosion inhibitors, antisettlement agents, additional insecticides (such as insecticidal carbamates, organophosphorus compounds, halogenated hydrocarbons, pyrethroides etc.), anti skinning aqents and the like.
- The above-mentioned additional ingredients and their use are described in prior art. (EP-A 0370665, DE-A 3531257, DE-A 3414244).
- The compositions according to the present invention generally comprise from about 10−6 to 30 parts by weight, preferably from about 0.0005 to 15 parts by weight and more preferably from 0.005 to 2 parts by weight of the insecticide of formula (I) and from 0.01 to 90 parts by weight, preferably from about 0.05 to 50 parts by weight and more preferably from 0.1 to 30 parts by weight of at least one of the above-mentioned fungicides.
- The compositions can be provided as ready for use products or as concentrates, which have to be diluted prior to use.
- The compositions can be applied by means of brushing, spraying, dipping, double vacuum and the like as known in the art. The compositions can be prepared by any technique known in the art.
- The content of the present invention will be concretely exolained by way of the following examples but the present invention should not be limited only thereto.
- *Remark: the percentages are given in percent by weight
-
0.005% 1-(6-chloro-3-pyridylmethyl)-2-nitroimino- imidazolidine (imidacloprid) 5% Butylglycol 94.995% Mineral spirits -
0.01% Imidacloprid 0.5% Dichlofluanide 1% Tebuconazole 9.7% Alkyd resin (solid) 88.79% Mineral spirits -
0.01% imidacloprid 0.5% Dichlofluanide 1.2% Tebuconazole 21% Alkyd resin (solid) 2% Pigment 4% Antisettlement additive, dryes etc. 71.29% Mineral spirits -
0.015% imidacloprid 0.6% Dichlofluanide 1.5% Tebuconazole 40% Alkyd resin 2% Pigment 4% Antisettlement additive, dryer etc. 48.115% Mineral spirits -
20% imidacloprid 8% ethylene glycol 3% emulsifiers 0.25% thickeners 68.75% distilled water -
0.1% imidacloprid 1% 3-bromo-2,3-diiodo-2-propenyl ethylcarbonate 98.9% organic solvents -
0.1% imidacloprid 1.5% 4-chlorophenyl-3- iodopropargylformal 98.4% organic solvents - Compounds Under Test
- Examples of the Active Compounds According to the Present Invention
- I.1: 1-(6-chloro-3-pyridylmethyl)-2-nitromethylene-imidazolidine
- I.2: 3-(6-chloro-3-pyridylmethyl)-2-nitromethylene-thiazolidine
- I.3: imidacloprid
- Comparative Compounds
- A: phoxim
- B: chlorpyriphos
- Preparation of Test Formulation:
- Solvent: 3 parts by weight of xylene
- Emulsifier: 1 part by weight of polyoxyethylene-alkylphenyl-ether
- To prepare a suitable formulation of the active compound, 1 part by weight of each of the active compounds was mixed with the above-mentioned amount of the solvent containing the above-mentioned amount of the emulsifier, and the mixture was diluted with water to a predetermined concentration.
- Test Method:
- 1 ml of the aqueous solution prepared in the above-mentioned procedure was uniformly applied using a pipette onto a filter paper that was placed in petri dish of 9 cm diameter. Ten head of worker termites (Coptotermes formosanus) were replaced into the petri dish and it was kept in a constant temperature chamber at 25° C.
- After four days, the mortality of the termites was investigated. This test procedure was carried out in duplicate per each concentration of the active compounds under test.
- The test results are shown in Table 1.
TABLE 1 Concentration of Mortality of termites active compound after four days Compound (ppm) (%) I.1 40 100 8 100 1.6 100 0.32 100 I.2 40 100 8 100 1.6 100 0.32 100 I.3 40 100 8 100 1.6 100 0.32 100 A 40 100 8 100 1.6 100 0.32 90 B 40 100 8 100 1.6 100 0.32 100 UnTreated 0 - Small blocks of Japanese redpine tree ( 2 cm×2 cm×2 cm) were soaked for one minute into the aqueous solution prepared by the similar procedure to Example 8.
- After air-dried, they were kept in a constant temperature chamber at 40° C. for four weeks. Then each of the thus treated blocks was placed in a polymeric cup (10 cm diameter) containing 150 ml of sandy loam of 20% moisture content. Into each of the polymeric cups, 100 head of working termites and 10 head of soldier termites (Coptotermes formosanus) were released. After three weeks, the degree of xylophagous damage in the block and the mortality of the termites were investigated.
- Three tests were carried out in duplicate 25° C., and the results are shown in Table 2.
- The index of xylophagous damage observed on the test blocks:
0 No damage 0.5 One to two traces of damage each having a depth of about 1 mm from the block surface 1 One to two evident damages each having a depth from 1 to 2 mm from the block surface 2 More than three evident damages or more than one deep trace of damage having a depth of more than 2 mm from the block surface 3 More than three deep damages 4 Evidently damaged zone covering up to about one third of the whole surface area of the block 5 Evidently damaged zone covering more than one third of the whole surface area of the block -
TABLE 2 Degree of Concentration Mortality xylophagous of active termites damage in the compound after three pine tree Compound (ppm) weeks (%) block (0-5) I.1 40 100 0 8 100 0 1.6 100 0 0.32 98 0.5 I.2 40 100 0 8 100 0 1.6 100 0 0.32 100 0 I.3 40 100 0 8 100 0 1.6 100 0 0.32 100 0 A 40 25 3 8 0 5 1.6 0 5 0.32 0 5 B 40 100 0 8 78 1 1.6 0 3 0.32 0 5 Untreated 0 5 - The toxicity against larvae of Hylotorupes bajulus, using wood samples treated with the active compound I.3 provided in Example 8 in chloroform having concentrations of 1.44×10−5%, 1.44×10−4%, 7.2×10−3%, and 1.44×10−2% was determined according to the detailed description of DIN EN 47 (edition 1990, Beuth Verlag GMBH) which is concerned with the European standard method prescribed by the European Committee for standardization concerning wood preservatives, determination of the toxic value against larvae of Hylotrupes bajulus.
- An outline of the method is as follows: (see DIN EN 47 for detail)
- Five wood-samples (50 mm×25 mm×15 mm) which are treated by the active compound beforehand (impregnation treatment in vacuum) are provided and in each specimen, a regular pattern of six holes are bored, and then one head of the larvae is inserted per a hole.
- After four weeks, the specimens are cut up in turn and the number of live/dead of larvae is determined.
- In determination, where a live larvae is identified in a specimen, then the remaining specimens without cutting up are stored for a further eight weeks, and afterword, the of live/dead larvae is determined.
- From this test, the Toxic threshold value was between 1.08 g/m3 and 10.8 g/m3 of the active compound I.3.
- The results are shown in Table 3.
TABLE 3 Concen- State of the larvae at the end of Duration tration Quantity of active compound the test of the of the concentrate absorbed in dead test in impregnating g/m3 wood no wood wood not weeks solution (%) min. max. M-value digested digested living found 4 0.0144 82.08 116.64 103.97 27 3 0 0 0.0072 45.36 56.63 52.85 29 1 0 0 0.00144 10.08 11.23 10.80 4 6 1 1 (*1) 12 0.00144 9.94 11.66 10.80 6 11 0 1 (*2) 0.000144 0.95 1.21 1.08 4 12 11 3 0.0000144 0.09 0.12 0.11 1 4 23 2 12 control impregnated with 2 2 24 2 semoles chloroform not treated 1 1 27 1
Note:
(*1) One live larvae was found in the second specimen.
(*2) The remaining three specimens were tested for further eight weeks (12 weeks in total).
- Comparative values of W. Metzner et al in “Holz als Rohund Werkstoff, 35 (1977) 233-237”, table 6 on page 236.
TABLE 4 Insecticide toxic value (g/m3) DDT 5-10 Diazinon 12-18-22 Phoxim 7-12 Chlorophoxim 12-20-32 Bassa (Baycarb) 17-30-44 Propoxur 18-30 Carbaryl 12-18 - The toxicity against Reticulitermes santonensis of solutions containing the active compound I.3 in chloroform having the concentrations mentioned in Example 10 was determined according to the detailed description of DIN EN 117 Edition 1981 which is concerned with the European standard method prescribed by the European Committee for standardization concerning wood preservatives, determination of the toxic value against Reticulitermes santonesis.
- An outline of the method is as follows: (see DIN EN 117 for detail)
- The same three wood-samples with impregnation treatment in vacuum as in Example 10 are provided.
- They are exposed to 250 workers, 1 soldier and 1 nymph per batch for eight weeks, and afterword, the number of live/dead larvae is determined.
- From this test, the toxic threshold value was between 0.135 g/m3 and 1.344 g/m3 of the active compound I.3.
- The evaluation was made by the following standard:
- *rating values:
-
- 0=no attack
- 1=attempted attack
- 2=slight attack
- 3=average attack
- 4=strong attack
- The results are shown in Table 5.
TABLE 5 Quantity of Quantity of protective agent Concentration solution absorbed Results of evaluation of protect absorbed average sur- agent tested No. of per wood per wood quantity viving Soldiers(S) in % wood sample sample absorbed workers or (m/m) sample in g/m3 in g/m3 in g/m3 % nymphs (N) * rating 1.44 × 10−5% 1 17.75 0.136 0.135 55 S/N 4 2 17.47 0.134 51 S/N 4 3 17.69 0.136 58 S/N 4 1.44 × 10−4% 4 17.75 1.363 1.344 0 — 1 5 17.39 1.336 0 — 1 6 17.37 1.334 0 — 1 1.44 × 10−3% 7 17.54 13.471 13.463 0 — 1 8 17.56 13.486 0 — 1 9 17.49 13.432 0 — 1 7.20 × 10−3% 10 17.29 66.3936 68.211 0 — 0 11 18.03 69.2352 0 — 0 12 17.97 69.0048 0 — 0 1.44 × 10−2% 13 17.79 136.627 136.627 0 — 0 14 17.72 136.090 0 — 0 15 17.86 137.165 0 — 0 control samples 16 17.72 0 0 50 —/N 4 diluent 17 18.15 0 57 S/N 4 (chloroform) 18 17.77 0 48 S/N 4 control samples) 19 0 0 0 55 S/N 4 untreated 20 0 0 62 S/N 4 21 0 0 64 —/N 4 - Comparative values of W. Metzner et al in “Holz als Rohund Werkstoff,” 35 (1977) 233-237, table 10 on page 236.
TABLE 6 toxic value Insecticide g/m3 DDT >1 500 Dieldrin 50 Lindan 75 Ethylparathion 200 Phoxim 400 Chlorophoxim 500 Bassa 500 Propoxur 140 Carbaryl 1 100
Claims (11)
1-6. (canceled)
7. A method of protecting a technical material exposed to soil comprising applying to the soil, either before or after the technical material contacts the soil, a composition comprising an insecticidally effective amount of an insecticide having the formula (I)
wherein
X is NH or S,
Y is CH or N,
Z is 2-chloro-5-pyridyl or 2-chloro-5-thiazolyl,
R1 is hydrogen or methyl, and
n is 0 or 1.
8. A method according to claim 7 wherein the insecticide having the formula (I) is 1-(6-chloro-3-pyridylmethyl)-2-nitroiminoimidazolidine.
9. A method according to claim 7 additionally comprising a fungicidally effective amount of a fungicide.
10. A method according to claim 9 wherein the fungicide is N-dichlorofluoromethylthio-N′,N′-dimethyl-N-phenyl sulfuric acid diamide, N-dichlorofluoromethylthio-N′,N′-dimethyl-N-p-toluylsulphamide, N-trichloromethylthiophthalimide, N-dichlorofluoromethylthiophthalimide, 3-iodo-2-propynyl-butylcarbamate, 3-iodo-tribromophenol, tetrachlorophenol, pentachlorophenol, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone, β-1(4-chlorophenoxy)-α-(1,1 dimethylethyl)-1H-1,2,4-triazole-1-ethanol, ±α[2-(4-chlorophenyl ethyl]-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol, 1-[2(2,4-dichlorophenyl) 4-propyl-1,3-dioxolan-1-yl-methyl]-1H-1,2,4-triazole, 1-[2(2,4-dichlorophenyl)-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole, (RS)-2(2,4-dichlorophenyl)-1-)1H-1,2,4-triazole-2-yl)-2-ol, 1-N-propyl-N-[2,4,6-trichlorophenoxy)ethyl]carbamoylimidazole, 2(2′-furyl)-1H-benzimidazole, methylbenzimidazol-2-ylcarbamate, 2(4′-thiazolyl) benzimidazole, methyl (1-butyl-carbamoyl)-2-benzimidazole carbamate, N-methylisothiazolin-3-one, 5-chloro-N-methylisothiazolin-3-one, 4,5-dichloro-N-octylisothiazolin-3-one, N-octylisothiazolin-3-one, C14-C11-4-alkyl-2,6-dimethymorpholine, 1-hydroxy-2-pyridinethione or a sodium, iron, manganese, or zinc salt thereof, tetrachloro-4-methylsulphonylpyridine, tris(N-cyclohexyldiaziniumdioxy) aluminum, bis(N-cyclohexyldiaziniumdioxy) copper, zinc naphthenate, copper salt of 8-hydroxyquinoline, 1,2,3,5-tetrachloro-4,6-cyanobenzene, N′-(3,4-dichlorophenyl)-N,N,-dimethylurea, boric acid, borax, a borate, methylenebisthiocyanate, 2-thiocycanomethylthiobenzothiazole, tributyl tin octoate, tributyl tin oleate, bistributyl tin oxide, tributyl tin naphthenate, tributyl tin phosphate, tributyl tin benzoate, or a combination thereof.
11. A method according to claim 9 comprising applying to the soil a composition comprising
(a) from about 10−6 to 30 parts by weight of the insecticide having the formula (I); and
(b) from about 0.01 to about 90 parts by weight of the fungicide.
12. A method according to claim 9 comprising applying to the soil a composition comprising
(a) from about 0.0005 to 15 parts by weight of the insecticide having the formula (I); and
(b) from about 0.05 to about 50 parts by weight of the fungicide.
13. A method according to claim 9 comprising applying to the soil a composition comprising
(a) from about 10−6 to 30 parts by weight of 1-(6-chloro-3-pyridylmethyl)-2-nitroiminoimidazolidine; and
(b) from about 0.01 to about 90 parts by weight of ±α-[2-(4-chlorophenyl ethyl]-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol.
14. A method according to claim 9 comprising applying to the soil a composition comprising
(a) from about 0.0005 to 15 parts by weight of 1-(6-chloro-3-pyridylmethyl)-2-nitroiminoimidazolidine; and
(b) from about 0.05 to about 50 parts by weight of ±α-[2-(4-chlorophenyl ethyl]-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol.
15. A method according to claim 7 wherein the technical material is wood, a composite wood material, paper, leather, a leather product, a synthetic polymer, a natural polymer, a textile, or a combination thereof.
16. A method according to claim 7 wherein the technical material is wood or a composite wood material.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US11/146,800 US20050234070A1 (en) | 1991-04-27 | 2005-06-07 | Agents for preserving technical materials against insects |
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
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JP12517291 | 1991-04-27 | ||
JPHEI3-125172 | 1991-04-27 | ||
JP35075191A JP3162450B2 (en) | 1991-04-27 | 1991-12-12 | Pest control agent to protect craft materials from pests |
JPHEI3-350751 | 1991-12-12 | ||
US87227992A | 1992-04-22 | 1992-04-22 | |
US08/543,351 US6323224B1 (en) | 1991-04-27 | 1995-10-16 | Agents for preserving technical materials against insects |
US09/886,197 US6936624B2 (en) | 1991-04-27 | 2001-06-21 | Agents for preserving technical materials against insects |
US11/146,800 US20050234070A1 (en) | 1991-04-27 | 2005-06-07 | Agents for preserving technical materials against insects |
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US09/886,197 Division US6936624B2 (en) | 1991-04-27 | 2001-06-21 | Agents for preserving technical materials against insects |
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US20050234070A1 true US20050234070A1 (en) | 2005-10-20 |
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ID=27471088
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US09/886,197 Expired - Fee Related US6936624B2 (en) | 1991-04-27 | 2001-06-21 | Agents for preserving technical materials against insects |
US11/146,800 Abandoned US20050234070A1 (en) | 1991-04-27 | 2005-06-07 | Agents for preserving technical materials against insects |
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Families Citing this family (7)
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US6936624B2 (en) * | 1991-04-27 | 2005-08-30 | Nihon Bayer Agrochem K.K. | Agents for preserving technical materials against insects |
DE10228104A1 (en) * | 2002-06-24 | 2004-01-15 | Bayer Cropscience Ag | Fungicidal active ingredient combination |
GB0604602D0 (en) * | 2006-03-07 | 2006-04-19 | Univ Edinburgh | Ruthenium (II) compounds |
GB0610062D0 (en) * | 2006-05-19 | 2006-06-28 | Univ Edinburgh | Ruthenium (ll) compounds |
GB201010439D0 (en) | 2010-06-21 | 2010-08-04 | Arch Timber Protection Ltd | A method |
GB201119139D0 (en) | 2011-11-04 | 2011-12-21 | Arch Timber Protection Ltd | Additives for use in wood preservation |
CN106457600A (en) | 2014-05-02 | 2017-02-22 | 奥麟木材保护有限公司 | Wood preservative composition |
Citations (8)
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---|---|---|---|---|
US4678795A (en) * | 1984-04-13 | 1987-07-07 | Nihon Tokushu Noyaku Seizo K.K. | 1-pyridylmethyl-2-nitromethylene-1,3-diazacycloalkane insecticides |
US4731385A (en) * | 1985-10-26 | 1988-03-15 | Nihon Tokushu Noyaku Seizo K.K. | Insecticidal and fungicidal composition for agricultural and horticultural use |
US4742060A (en) * | 1985-02-04 | 1988-05-03 | Nihon Tokushu Noyaku Seizo K. K. | Heterocyclic compounds |
US5087632A (en) * | 1989-06-16 | 1992-02-11 | Nihon Tokushu Noyaku Seizo K.K. | Formicidal agent for combating termites |
US5165934A (en) * | 1989-11-28 | 1992-11-24 | Nihon Bayer Agrochem K.K. | Stabilized agrochemical compositions |
US5972971A (en) * | 1993-06-21 | 1999-10-26 | Bayer Aktiengesellschaft | Fungicidal active compound combinations |
US6323224B1 (en) * | 1991-04-27 | 2001-11-27 | Nihon Bayer Agrochem K.K. | Agents for preserving technical materials against insects |
US6936624B2 (en) * | 1991-04-27 | 2005-08-30 | Nihon Bayer Agrochem K.K. | Agents for preserving technical materials against insects |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4648988A (en) * | 1983-12-21 | 1987-03-10 | Janssen Pharmaceutica, N.V. | Water-dilutable wood-preserving liquids |
EP0214546A2 (en) | 1985-09-05 | 1987-03-18 | Nihon Tokushu Noyaku Seizo K.K. | Insecticidal composition for use in agriculture and horticulture |
-
2001
- 2001-06-21 US US09/886,197 patent/US6936624B2/en not_active Expired - Fee Related
-
2005
- 2005-06-07 US US11/146,800 patent/US20050234070A1/en not_active Abandoned
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4678795A (en) * | 1984-04-13 | 1987-07-07 | Nihon Tokushu Noyaku Seizo K.K. | 1-pyridylmethyl-2-nitromethylene-1,3-diazacycloalkane insecticides |
US4742060A (en) * | 1985-02-04 | 1988-05-03 | Nihon Tokushu Noyaku Seizo K. K. | Heterocyclic compounds |
US4731385A (en) * | 1985-10-26 | 1988-03-15 | Nihon Tokushu Noyaku Seizo K.K. | Insecticidal and fungicidal composition for agricultural and horticultural use |
US5087632A (en) * | 1989-06-16 | 1992-02-11 | Nihon Tokushu Noyaku Seizo K.K. | Formicidal agent for combating termites |
US5165934A (en) * | 1989-11-28 | 1992-11-24 | Nihon Bayer Agrochem K.K. | Stabilized agrochemical compositions |
US6323224B1 (en) * | 1991-04-27 | 2001-11-27 | Nihon Bayer Agrochem K.K. | Agents for preserving technical materials against insects |
US6936624B2 (en) * | 1991-04-27 | 2005-08-30 | Nihon Bayer Agrochem K.K. | Agents for preserving technical materials against insects |
US5972971A (en) * | 1993-06-21 | 1999-10-26 | Bayer Aktiengesellschaft | Fungicidal active compound combinations |
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