JPH0134964B2 - - Google Patents
Info
- Publication number
- JPH0134964B2 JPH0134964B2 JP55015073A JP1507380A JPH0134964B2 JP H0134964 B2 JPH0134964 B2 JP H0134964B2 JP 55015073 A JP55015073 A JP 55015073A JP 1507380 A JP1507380 A JP 1507380A JP H0134964 B2 JPH0134964 B2 JP H0134964B2
- Authority
- JP
- Japan
- Prior art keywords
- repellent
- present
- repellent effect
- compound
- test
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 70
- 239000004480 active ingredient Substances 0.000 claims description 25
- 239000000077 insect repellent Substances 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000005871 repellent Substances 0.000 description 83
- 230000002940 repellent Effects 0.000 description 83
- 230000000694 effects Effects 0.000 description 55
- -1 thiocyanate compound Chemical class 0.000 description 52
- 241000607479 Yersinia pestis Species 0.000 description 51
- 238000012360 testing method Methods 0.000 description 47
- 239000000123 paper Substances 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 15
- 239000006210 lotion Substances 0.000 description 14
- 239000004744 fabric Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 241000257303 Hymenoptera Species 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 241000237858 Gastropoda Species 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 241000255925 Diptera Species 0.000 description 7
- 239000002917 insecticide Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 235000013311 vegetables Nutrition 0.000 description 7
- 239000002023 wood Substances 0.000 description 7
- 241000238657 Blattella germanica Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000011120 plywood Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 239000013068 control sample Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000252233 Cyprinus carpio Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000257226 Muscidae Species 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241000258242 Siphonaptera Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000003623 enhancer Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 239000004745 nonwoven fabric Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- 239000000057 synthetic resin Substances 0.000 description 3
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010004194 Bed bug infestation Diseases 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 241001414835 Cimicidae Species 0.000 description 2
- 241000256059 Culex pipiens Species 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 2
- AKQOBHZKBDHWQI-BZEFIUHZSA-N O[C@H]1C[C@@H](CCC1)N1C(C2(C3=C1N=C(N=C3)NC1=CC=C(C=C1)S(=O)(=O)NC([2H])([2H])[2H])CC2)=O Chemical compound O[C@H]1C[C@@H](CCC1)N1C(C2(C3=C1N=C(N=C3)NC1=CC=C(C=C1)S(=O)(=O)NC([2H])([2H])[2H])CC2)=O AKQOBHZKBDHWQI-BZEFIUHZSA-N 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 229960001126 alginic acid Drugs 0.000 description 2
- 150000004781 alginic acids Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 210000000038 chest Anatomy 0.000 description 2
- 229940127108 compound 5g Drugs 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 2
- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000012784 inorganic fiber Substances 0.000 description 2
- 230000009545 invasion Effects 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000003915 liquefied petroleum gas Substances 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 229920001220 nitrocellulos Polymers 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- HZVFRKSYUGFFEJ-YVECIDJPSA-N (2r,3r,4s,5r)-7-phenylhept-6-ene-1,2,3,4,5,6-hexol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=CC1=CC=CC=C1 HZVFRKSYUGFFEJ-YVECIDJPSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- ZYAFYIUCLZDJLT-UHFFFAOYSA-N (aminosulfonothioylamino)-dichloro-fluoromethane Chemical compound NS(=O)(=S)NC(F)(Cl)Cl ZYAFYIUCLZDJLT-UHFFFAOYSA-N 0.000 description 1
- IGOWHGRNPLFNDJ-ZPHPHTNESA-N (z)-9-tricosene Chemical compound CCCCCCCCCCCCC\C=C/CCCCCCCC IGOWHGRNPLFNDJ-ZPHPHTNESA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- XYIANCZIPATGDH-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)-1,3,5-trioxane Chemical compound CC(C)C1OC(C(C)C)OC(C(C)C)O1 XYIANCZIPATGDH-UHFFFAOYSA-N 0.000 description 1
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- WYAUHKUSKIIGEI-UHFFFAOYSA-N 2-thiocyanatoacetic acid Chemical compound OC(=O)CSC#N WYAUHKUSKIIGEI-UHFFFAOYSA-N 0.000 description 1
- XWHQMTVBJPPDCB-UHFFFAOYSA-N 2-thiocyanatobutanoic acid Chemical compound CCC(C(O)=O)SC#N XWHQMTVBJPPDCB-UHFFFAOYSA-N 0.000 description 1
- QJZIGRDRTMUAAV-UHFFFAOYSA-N 2-thiocyanatopropanoic acid Chemical compound OC(=O)C(C)SC#N QJZIGRDRTMUAAV-UHFFFAOYSA-N 0.000 description 1
- XNYGOEGATLFFOX-UHFFFAOYSA-N 4,5a,6,9,9a,9b-hexahydro-1h-dibenzofuran-4a-carbaldehyde Chemical compound C12CC=CCC2OC2(C=O)C1CC=CC2 XNYGOEGATLFFOX-UHFFFAOYSA-N 0.000 description 1
- MGGVALXERJRIRO-UHFFFAOYSA-N 4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-2-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-1H-pyrazol-5-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)O MGGVALXERJRIRO-UHFFFAOYSA-N 0.000 description 1
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- PIVQQUNOTICCSA-UHFFFAOYSA-N ANTU Chemical compound C1=CC=C2C(NC(=S)N)=CC=CC2=C1 PIVQQUNOTICCSA-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000255628 Tabanidae Species 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- FIQBPVMEUQLQNH-UHFFFAOYSA-N but-2-enyl 2-thiocyanatoacetate Chemical compound S(C#N)CC(=O)OCC=CC FIQBPVMEUQLQNH-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920006184 cellulose methylcellulose Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- FODTZLFLDFKIQH-FSVGXZBPSA-N gamma-Oryzanol (TN) Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)O[C@@H]2C([C@@H]3CC[C@H]4[C@]5(C)CC[C@@H]([C@@]5(C)CC[C@@]54C[C@@]53CC2)[C@H](C)CCC=C(C)C)(C)C)=C1 FODTZLFLDFKIQH-FSVGXZBPSA-N 0.000 description 1
- 238000010413 gardening Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 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
- 239000004009 herbicide Substances 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- USSDLSWIXCOFDV-UHFFFAOYSA-N hexyl 2-thiocyanatoacetate Chemical compound CCCCCCOC(=O)CSC#N USSDLSWIXCOFDV-UHFFFAOYSA-N 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005360 mashing Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000003986 organophosphate insecticide Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- FWQHRZXEQNUCSY-UHFFFAOYSA-N tert-butyl N-[2-(ethoxycarbonylamino)-5-[(4-fluorophenyl)methyl-prop-2-ynylamino]phenyl]carbamate Chemical compound CCOC(=O)NC1=C(C=C(C=C1)N(CC#C)CC2=CC=C(C=C2)F)NC(=O)OC(C)(C)C FWQHRZXEQNUCSY-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は新しい害虫忌避剤に関する。
従来よりゴキブリ等の各種衛生害虫を防除する
方法としては、例えばピレスロイド系殺虫剤等の
殺虫剤を散布する方法や各種の捕虫器具等を用い
る方法が知られている。之等の方法は殺虫乃至捕
虫によつて害虫の殺滅を計り、該害虫による食害
や吸血等の被害をある程度防止できるものではあ
るが、例えば台所、畜舎、水屋、タンス等の家具
内又は人体、農作物等の動植物体への害虫の飛
来、接近、接触、侵入、汚染等を回避できるもの
ではなく、充分な防除効果は奏し得ない。しかも
上記方法においては殺虫乃至捕虫後の害虫の処理
が必要となり、殊に家具内等へ侵入後に死ぬ害虫
の処理は困難であると共にこれはむしろ汚染源と
なる弊害がある。一方上記害虫の飛来、侵入等を
防止でき、勿論死虫の処理を何ら必要としない害
虫防除方法として、害虫忌避剤を用いる方法が知
られており、近時上記方法に利用できる害虫忌避
作用を有する各種の物質が研究開発及び提案され
つつある。しかしながら上記提案された各種の物
質は、いずれも尚充分に満足できる害虫忌避効果
を発揮できるものではなく、わずかにＮ，Ｎ―ジ
エチル―メタ―トルアミドを始めとする数種の物
質が、スプレー、ローシヨン、クリーム等の形態
で蚊、ノミ、ナンキンムシ、サシバエ等の吸血害
虫に対する忌避剤として実用されているにすぎな
い。また、ISRAEL JOURNAL OF
ENTOMOLLGY，vol.XI，1976，p15〜31には、
一般式
The present invention relates to a new pest repellent. BACKGROUND ART Conventionally, methods for controlling various sanitary pests such as cockroaches include, for example, methods of spraying insecticides such as pyrethroid insecticides, and methods of using various insect traps. These methods kill pests by killing or trapping insects, and can prevent damage such as feeding damage and blood sucking caused by the pests to a certain extent, but they do not apply to the inside of furniture such as kitchens, livestock sheds, water sheds, chests of drawers, etc. It is not possible to avoid the flying, approaching, contact, invasion, contamination, etc. of pests to the human body, agricultural crops, and other animals and plants, and a sufficient pest control effect cannot be achieved. Moreover, in the above method, it is necessary to dispose of pests after killing or capturing them, and it is particularly difficult to dispose of pests that die after entering furniture, etc., and this has the disadvantage of becoming a source of contamination. On the other hand, a method using a pest repellent is known as a pest control method that can prevent the above pests from flying or entering, and of course does not require any treatment of dead insects. Research and development and proposals are being made on various substances that have the same properties. However, none of the various substances proposed above can exhibit a sufficiently satisfactory pest repellent effect, and only a few substances, including N,N-diethyl-meta-toluamide, can be used as sprays, It is only used as a repellent for blood-sucking pests such as mosquitoes, fleas, bed bugs, and stable flies in the form of lotions and creams. Also, ISRAEL JOURNAL OF
ENTOMOLLGY, vol.XI, 1976, p15-31,
general formula
【式】で表わされるアセ
テートが蚊に対して忌避作用を有することが報告
されている。しかしながら、本発明者の研究によ
れば、上記アセテートの蚊に対する忌避効果はそ
の濃度低下につれ激減する傾向にあり、従つて該
化合物は低濃度では使用できない欠点がある。し
かも上記化合物は各種害虫に対する忌避効力の持
続試験の結果、短期間に効力が失われ、持続性に
乏しいことも確認されている（後記比較例参照）。
本発明者らは上記現状に鑑み、優れた害虫忌避
効果を発揮し、害虫の侵入等をほぼ確実に防止可
能で、しかも各種害虫に対して低濃度でも効果が
あり、また優れた忌避効果の持続効果を発揮す
る。忌避剤を提供することを目的として種々研究
を重ねた。その結果下記一般式〔〕で表わされ
る特定のチオシアネート化合物が、上記目的に合
致する害虫忌避効果を発現できることを見い出し
た。
本発明はこの新しい知見に基づいて完成された
ものである。
即ち本発明は一般式
NCS（―CH2）―oCOOR 〔〕
〔式中ｎは１〜５の整数及びＲは炭素数３〜６
の直鎖状アルケニルもしくはアルキニル基を示
す。〕
で表わされる化合物を有効成分として含有するこ
とを特徴とする害虫忌避剤に係る。
本発明の害虫忌避剤は、その有効成分として上
記一般式〔〕で表わされる特定のチオシアネー
ト化合物を含有することに基づいて、極めて優れ
た害虫忌避効果を奏し得る。その忌避効果は、ゴ
キブリ、ハエ、カ、アブ、ノミ、ナンキンムシ等
の衛生害虫乃至吸血害虫は勿論のこと、イガ、コ
イガ等の衣料害虫、コクヌストモドキ、コクゾウ
ムシ等の貯穀害虫、更にはアリ及びナメクジ等に
対しても強力なものである。従つて本発明の害虫
忌避剤は、これを家庭内の玄関、台所、食堂等や
畜舎、農園芸ハウス等の特定区域、タンス、食物
収納庫、衣裳ケース、人形ケース等の収納家具
内、及び人体、動物体、植物体等に適用すること
によつて、之等の場所への害虫の飛来、接近、接
触、侵入等を確実に防止し、また上記特定区域内
等での害虫の棲息、食害等及び動植物体の刺咬、
吸血等、更には汚染をもみごとに回避できるので
ある。
本発明害虫忌避剤の有効成分とする上記一般式
〔〕で表わされるチオシアネートは、公知の化
合物であり、該化合物における酸部〔NCS（―
CH2）―oCOO〕はｎの値に応じてチオシアノ酢
酸、チオシアノプロピオン酸、チオシアノ酪酸、
チオシアノ吉草酸及びチオシアノカプロン酸より
選択される。また該化合物におけるアルコール部
分〔Ｒ〕は、炭素数３〜６の直鎖状アルケニルも
しくはアルキニル基であり、該基としては、例え
ばプロペニル、ブテニル、ペンテニル、ヘキセニ
ル、プロパルギル、ブチニル、ペンチニル、ヘキ
シニル、ペント―２，４―ジエニル、ペント―
２，４―ジイニル、ヘキサ―２，４―ジエニル、
ヘキサ―２―イン―５―エニル、ヘキサ―２，５
―ジイニル基等の炭化水素鎖中に１以上の二重結
合及び（又は）三重結合を有する基を例示でき
る。上記一般式〔〕で表わされるチオシアネー
トのうちで特に好ましい化合物を例示すれば次の
通りである。
チオシアノ酢酸２―ブテニル、チオシアノ酢酸
３―ブテニル、チオシアノ酢酸２―ペンテニル、
チオシアノ酢酸３―ペンテニル、チオシアノ酢酸
４―ペンテニル、チオシアノ酢酸２―ヘキセニ
ル、チオシアノ酢酸３―ヘキセニル、チオシアノ
酢酸４―ヘキセニル、チオシアノ酢酸５―ヘキセ
ニル、チオシアノ酢酸プロパルギル、チオシアノ
酢酸２―ブチニル、チオシアノ酢酸３―ブチニ
ル、チオシアノ酢酸２―ペンチニル、チオシアノ
酢酸３―ペンチニル、チオシアノ酢酸ヘキサ―
２，４―ジエニル、チオシアノプロピオン酸２―
プロペニル、チオシアノプロピオン酸２―ブテニ
ル、チオシアノプロピオン酸３―ブテニル、チオ
シアノプロピオン酸２―ペンテニル、チオシアノ
プロピオン酸３―ペンテニル、チオシアノプロピ
オン酸４―ペンテニル、チオシアノプロピオン酸
２―ヘキセニル、チオシアノプロピオン酸３―ヘ
キセニル、チオシアノプロピオン酸４―ヘキセニ
ル、チオシアノプロピオン酸５―ヘキセニル、チ
オシアノプロピオン酸プロパルギル、チオシアノ
プロピオン酸２―ブチニル、チオシアノプロピオ
ン酸３―ブチニル、チオシアノプロピオン酸２―
ペンチニル、チオシアノプロピオン酸３―ペンチ
ニル、チオシアノ酪酸２―ブテニル、チオシアノ
酪酸３―ブテニル、チオシアノ酪酸２―ペンテニ
ル、チオシアノ酪酸３―ペンテニル、チオシアノ
酪酸２―ヘキセニル、チオシアノ酪酸２―プロパ
ルギル、チオシアノ酪酸３―ブチニル、チオシア
ノ酪酸３―ペンチニル等。
本発明の害虫忌避剤は、上記有効成分化合物を
そのまま害虫忌避を要求される区域等に適用する
こともできるが、通常好ましくは適当な担体その
他の配合剤を用いて適用区域、適用方法等に適し
た各種の形態例えば液剤、固剤等に調製して利用
される。液剤の形態に調製するに当り用いられる
担体としては例えば水、メチルアルコール、エチ
ルアルコール等のアルコール類、アセトン、メチ
ルエチルケトン等のケトン類、テトラヒドロフラ
ン、ジオキサン等のエーテル類、ヘキサン、ケロ
シン、パラフイン、石油ベンジン等の脂肪族炭化
水素類、ベンゼン、トルエン等の芳香族炭化水素
類、酢酸エチル等のエステル類、ジクロロエタン
等のハロゲン化炭化水素類等を例示できる。之等
液剤の形態の本発明害虫忌避剤には更に通常の塗
膜形成剤、乳化剤、分散剤、展着剤、湿潤剤、安
定剤、噴射剤等の添加剤を配合することができ、
塗料形態、接着剤形態、乳剤、分散剤、懸濁剤、
ローシヨン、クリーム、噴霧剤、エアゾール剤等
の形態で利用することができる。之等の添加剤と
しては、例えばニトロセルロース、アセチルセル
ロース、アセチルブチリルセルロース、メチルセ
ルロース等のセルロース誘導体、酢酸ビニル樹脂
等のビニル系樹脂、アルキツド系樹脂、ユリア系
樹脂、エポキシ系樹脂、ポリエステル系樹脂、ウ
レタン系樹脂、シリコン系樹脂、アクリル系樹
脂、塩化ゴム、ポリビニルアルコール等の塗膜形
成剤、石けん類、ポリオキシエチレンオレイルエ
ーテルなどのポリオキシエチレン脂肪アルコール
エーテル、ポリオキシエチレンノニルフエニルエ
ーテルなどのポリオキシエチレンアルキルアリル
エーテル、ポリオキシエチレン脂肪酸エステル、
脂肪酸グリセリド、ソルビタン脂肪酸エステル、
高級アルコールの硫酸エステル、ドデシルベンゼ
ンスルホン酸ソーダなどのアルキルアリルスルホ
ン酸塩等の界面活性剤、液化石油ガス、ジメチル
エーテル、フルオロカーボン等の噴射剤、カゼイ
ン、ゼラチン、アルギン酸、CMC等を例示でき
る。
また固剤の形態に調製するに当り用いられる担
体としては、例えばケイ酸、カオリン、活性炭、
ベントナイト、珪藻土、タルク、クレー、炭酸カ
ルシウム、陶磁器粉等の鉱物質粉末や、木粉、大
豆粉、小麦粉、でん粉やシクロデキストリン等の
包接化合物等の植物質粉末等を例示できる。更に
該固剤の形態に調製するに当つては、例えばトリ
シクロデカン、シクロドデカン、２，４，６―ト
リイソプロピル―１，３，５―トリオキサン、ト
リメチレンノルボルネン等の昇華性担体やパラジ
クロロベンゼン、ナフタリン、樟脳等の昇華性防
虫剤を用い、上記有効成分化合物を溶融混合又
は、擂潰混合後成型して、昇華性固剤とすること
もできる。また上記固剤には、有効成分化合物を
プラスチツクスに練り込んだ樹脂成型物の形態も
包含される。
また本発明の害虫忌避剤は、例えばポリビニル
アルコールやCMC等を用いたスプレードライ法、
ゼラチン、ポリビニルアルコール、アルギン酸等
を用いた液中硬化法、コアセルベーシヨン法等に
従いマイクロカプセル化した形態に調製したり、
ベンジリデン―Ｄ―ソルビトール、カラギ―ナン
等のゲル化剤を用いてゲルの形態に調製すること
もできる。
更に本発明の害虫忌避剤は、公知の害虫忌避
剤、効力増強剤、酸化防止剤、殺虫剤、げつ歯動
物駆除及び忌避剤、殺菌剤、防徴剤、除草剤、肥
料、着香料、着色料等を配合することができる。
配合可能な他の害虫忌避剤としては、Ｎ，Ｎ―ジ
エチル―メタ―トルアミド、２，３，４，５―ビ
ス（Δ2―ブチレン）―テトラヒドロフルフラー
ル、ジ―ｎ―プロピル イソシンコメロネート、
ジ―ｎ―ブチルサクシネート、２―ヒドロキシエ
チルオクチルサルフアイド等を、効力増強剤とし
てはＮ―（２―エチルヘキシル）―ビシクロ―
〔２，２，１〕―５―ヘプテン―２，３―ジカル
ボキシイミド、６―（プロピルピペロニル）―ブ
チルカルビチルエーテル等を、酸化防止剤として
はブチルヒドロキシアニソール、ジブチルヒドロ
キシトルエン、トコフエロール、γ―オリザノー
ル等を、殺虫剤としては一般名アレスリン及びそ
の幾何及び（又は）光学異性体等のピレスロイド
類を、げつ歯動物駆除及び忌避剤としてはα―ナ
フチルチオウレア、シクロヘキシミド等を、殺菌
剤としてはサリチル酸、ｐ―クロロ―ｍ―キシレ
ノール、２―（4′―チアゾイル）ベンズイミダゾ
ール等を、防徴剤としてはα―ブロモシンナミツ
クアルデヒド、Ｎ―ジメチル―Ｎ―フエニル―
N′―（フルオロジクロロメチル）チオスルフア
ミド等を夫々例示できる。
かくして調製される各種形態を有する本発明の
害虫忌避剤は、その使用に当り忌避効果を要求さ
れる害虫の侵入区域例えば農作物栽培畑、果樹園
等、一般家庭、穀物倉庫、食堂の厨房、家具、押
入れ、玄関、洗面所等に載置、撒布、噴霧、塗
布、貼り付け等により、また動植物体自体に撒
布、噴霧、塗布等により適用できる。
また本発明の害虫忌避剤は、これを予め適当な
シート状基材に塗布、含浸、滴下、混練等により
保持させ、該形態で目的とする箇所に載置したり
貼り合せることにより利用することもできる。こ
の際用いられるシート状基材としては、例えばポ
リエチレン、ポリプロピレン、ナイロン、ポリ塩
化ビニル、ポリ塩化ビニリデン、ポリエステル等
の合成樹脂シート、動植物質又は無機質繊維体シ
ート（紙、布、不織布、皮革等）、之等合成樹脂
と無機質繊維または粉体との混合シートまたは混
紡布、上記合成樹脂と動植物繊維との混紡布また
は不織布、アルミニウム、ステンレス、亜鉛等の
金属の箔乃至フイルム及び上記各種シートの種層
シートを例示できる。更に本発明の害虫忌避剤
は、これを家具部材とする天然材料例えばキリ、
ペンシルシダ、クス等やプラスチツクス例えば塩
化ビニル樹脂、塩素化ポリエチレン、ポリエチレ
ン、ポリプロピレン等に予め塗布、含浸、滴下、
混練等により保持させて利用することも可能であ
る。
本発明害虫忌避剤中の有効成分化合物量及び該
忌避剤の適用量は、その剤型や適用方法、適用場
所等に応じて適宜に決定すればよく、限定的では
ないが、通常分散剤や水和剤等の液剤の形態で用
いる場合、有効成分化合物を１〜80重量％好まし
くは５〜40重量％含有させればよく、粉剤等の固
剤の形態とする場合１〜50重量％好ましくは２〜
20重量％含有させればよく、またシート状基材や
家具部材に保持させた形態とする場合には、基材
等の飽和含浸量のほぼ1/2倍量を保持させればよ
い。また本発明害虫忌避剤の適用量としては、例
えば塗布使用の場合、塗布すべき面積１cm2当りに
有効成分化合物を約0.001mg以上好ましくは約
0.001〜0.05mgとするのがよく、固剤その他の形
態で用いる場合、適用空間１m3当り有効成分化合
物を約１mg以上存在させるのが適当である。
以下本発明を更に詳しく説明するため実施例を
挙げる。
実施例 １
下記一般式〔〕で表わされる各化合物につ
き、そのチヤバネゴキブリに対する忌避効果を次
の方法により調べる。即ち各供試化合物の0.05
mg／cm2を円形紙（径11cm）に含浸させ、その中
央及び何ら供試化合物を含浸させない対照紙の
中央に夫々角砂糖１個を置き、これら各１対を、
チヤバネゴキブリ成虫雄雌各25頭を飼育している
飼育箱内に重ならないように並べ、３日間放置後
の各紙上角砂糖の重量減少量（喫食量）（Ｘmg
とする）を測定する。各供試化合物の忌避効果
は、対照紙上の角砂糖の減少量（喫食量）（Ａ
mgとする）を基準とし、下式に従い算出される。
忌避効果（％）＝Ａ（mg）−Ｘ（mg）／Ａ（mg）×
100
得られた結果を次の基準により判定し、下記第
１表に示す。
…忌避効果 90％以上
… 〃 70〜90％
＋… 〃 50〜70％
±… 〃 30〜50％
−… 〃 30％以下It has been reported that acetate represented by the formula has a repellent effect against mosquitoes. However, according to research conducted by the present inventors, the mosquito repellent effect of acetate tends to decrease sharply as its concentration decreases, and therefore, the compound has the drawback that it cannot be used at low concentrations. Moreover, as a result of tests on the durability of the repellent efficacy of the above compounds against various insect pests, it has been confirmed that the efficacy is lost in a short period of time and the sustainability is poor (see Comparative Examples below). In view of the above-mentioned current situation, the present inventors have demonstrated an excellent pest repellent effect, can almost certainly prevent the invasion of pests, are effective against various pests even at low concentrations, and have an excellent pest repellent effect. Demonstrates a lasting effect. Various studies have been conducted with the aim of providing a repellent. As a result, it has been found that a specific thiocyanate compound represented by the following general formula [] can exhibit pest repellent effects that meet the above objectives. The present invention was completed based on this new knowledge. That is, the present invention is based on the general formula NCS(-CH 2 )- o COOR [] [where n is an integer of 1 to 5 and R is a carbon number of 3 to 6]
represents a linear alkenyl or alkynyl group. ] This invention relates to an insect repellent characterized by containing a compound represented by the following as an active ingredient. The pest repellent of the present invention can exhibit extremely excellent pest repellent effects because it contains the specific thiocyanate compound represented by the above general formula [] as its active ingredient. Its repellent effects include not only sanitary pests and blood-sucking pests such as cockroaches, flies, mosquitoes, horseflies, fleas, and bed bugs, but also clothing pests such as burrs and carp moths, grain storage pests such as brown weevils, and even ants and slugs. It is also powerful against the like. Therefore, the pest repellent of the present invention can be used in specific areas of the home such as entrances, kitchens, dining rooms, livestock sheds, agricultural and gardening houses, inside storage furniture such as chests of drawers, food storages, clothing cases, doll cases, etc. By applying it to the human body, animal body, plant body, etc., it can reliably prevent pests from flying, approaching, contacting, or invading such places, and can also prevent pests from living in the specified areas, etc. Feeding damage and bites of animals and plants,
Blood-sucking and even contamination can be successfully avoided. The thiocyanate represented by the above general formula [], which is the active ingredient of the pest repellent of the present invention, is a known compound, and the acid moiety [NCS (-
CH 2 ) - o COO] is thiocyanoacetic acid, thiocyanopropionic acid, thiocyanobutyric acid,
selected from thiocyanovaleric acid and thiocyanocaproic acid. The alcohol moiety [R] in the compound is a linear alkenyl or alkynyl group having 3 to 6 carbon atoms, such as propenyl, butenyl, pentenyl, hexenyl, propargyl, butynyl, pentynyl, hexynyl, pentyl, -2,4-dienyl, pento-
2,4-diynyl, hexa-2,4-dienyl,
hex-2-yn-5-enyl, hex-2,5
Examples include groups having one or more double bonds and/or triple bonds in the hydrocarbon chain, such as -diynyl groups. Among the thiocyanates represented by the above general formula [], particularly preferred compounds are as follows. 2-butenyl thiocyanoacetate, 3-butenyl thiocyanoacetate, 2-pentenyl thiocyanoacetate,
3-pentenyl thiocyanoacetate, 4-pentenyl thiocyanoacetate, 2-hexenyl thiocyanoacetate, 3-hexenyl thiocyanoacetate, 4-hexenyl thiocyanoacetate, 5-hexenyl thiocyanoacetate, propargyl thiocyanoacetate, 2-butynyl thiocyanoacetate, 3-hexenyl thiocyanoacetate Butynyl, 2-pentynyl thiocyanoacetate, 3-pentynyl thiocyanoacetate, hexyl thiocyanoacetate
2,4-dienyl, thiocyanopropionic acid 2-
propenyl, 2-butenyl thiocyanopropionate, 3-butenyl thiocyanopropionate, 2-pentenyl thiocyanopropionate, 3-pentenyl thiocyanopropionate, 4-pentenyl thiocyanopropionate, 2-hexenyl thiocyanopropionate, 3-hexenyl thiocyanopropionate, 4-hexenyl thiocyanopropionate, 5-hexenyl thiocyanopropionate, propargyl thiocyanopropionate, 2-butynyl thiocyanopropionate, 3-butynyl thiocyanopropionate, thiocyanopropionic acid 2-
Pentynyl, 3-pentynyl thiocyanopropionate, 2-butenyl thiocyanobutyrate, 3-butenyl thiocyanobutyrate, 2-pentenyl thiocyanobutyrate, 3-pentenyl thiocyanobutyrate, 2-hexenyl thiocyanobutyrate, 2-propargyl thiocyanobutyrate, 3-thiocyanobutyrate Butynyl, 3-pentynyl thiocyanobutyrate, etc. In the pest repellent of the present invention, the above-mentioned active ingredient compound can be applied as it is to areas where pest repellency is required, but it is usually preferable to use a suitable carrier or other compounding agent to adjust the application area, application method, etc. It is prepared and used in various suitable forms, such as liquids and solids. Examples of carriers used in preparing liquid preparations include water, alcohols such as methyl alcohol and ethyl alcohol, ketones such as acetone and methyl ethyl ketone, ethers such as tetrahydrofuran and dioxane, hexane, kerosene, paraffin, and petroleum benzine. Examples include aliphatic hydrocarbons such as benzene and toluene, aromatic hydrocarbons such as benzene and toluene, esters such as ethyl acetate, and halogenated hydrocarbons such as dichloroethane. The insect repellent of the present invention in the form of a liquid may further contain conventional additives such as film forming agents, emulsifiers, dispersants, spreading agents, wetting agents, stabilizers, propellants, etc.
Paint form, adhesive form, emulsion, dispersant, suspending agent,
It can be used in the form of lotion, cream, spray, aerosol, etc. Examples of such additives include cellulose derivatives such as nitrocellulose, acetylcellulose, acetylbutyrylcellulose, and methylcellulose, vinyl resins such as vinyl acetate resin, alkyd resins, urea resins, epoxy resins, and polyester resins. , urethane resins, silicone resins, acrylic resins, chlorinated rubber, coating film forming agents such as polyvinyl alcohol, soaps, polyoxyethylene fatty alcohol ethers such as polyoxyethylene oleyl ether, polyoxyethylene nonyl phenyl ether, etc. polyoxyethylene alkyl allyl ether, polyoxyethylene fatty acid ester,
fatty acid glyceride, sorbitan fatty acid ester,
Examples include surfactants such as sulfuric esters of higher alcohols, alkylaryl sulfonates such as sodium dodecylbenzenesulfonate, propellants such as liquefied petroleum gas, dimethyl ether, and fluorocarbons, casein, gelatin, alginic acid, and CMC. In addition, examples of carriers used for preparation in solid form include silicic acid, kaolin, activated carbon,
Examples include mineral powders such as bentonite, diatomaceous earth, talc, clay, calcium carbonate, and ceramic powder, and vegetable powders such as wood flour, soybean flour, wheat flour, and clathrate compounds such as starch and cyclodextrin. Furthermore, in preparing the solid form, sublimable carriers such as tricyclodecane, cyclododecane, 2,4,6-triisopropyl-1,3,5-trioxane, trimethylene norbornene, and paradichlorobenzene are used. It is also possible to use a sublimable insect repellent such as , naphthalene, or camphor to form a sublimable solid agent by melt-mixing the above-mentioned active ingredient compounds or by mashing and molding. The above-mentioned solid agent also includes the form of a resin molded product in which the active ingredient compound is kneaded into plastic. In addition, the pest repellent of the present invention can be obtained by spray drying using polyvinyl alcohol, CMC, etc.
Prepared in microencapsulated form using gelatin, polyvinyl alcohol, alginic acid, etc. according to liquid curing method, coacervation method, etc.
It can also be prepared in the form of a gel using a gelling agent such as benzylidene-D-sorbitol or carrageenan. Furthermore, the pest repellent of the present invention may contain known pest repellents, efficacy enhancers, antioxidants, insecticides, rodent control and repellents, fungicides, repellents, herbicides, fertilizers, flavoring agents, Colorants and the like can be added.
Other pest repellents that can be blended include N,N-diethyl-meth-toluamide, 2,3,4,5-bis(Δ 2 -butylene)-tetrahydrofurfural, di-n-propyl isocincomeronate,
Di-n-butyl succinate, 2-hydroxyethyl octylsulfide, etc., and N-(2-ethylhexyl)-bicyclo- as the potency enhancer.
[2,2,1]-5-heptene-2,3-dicarboximide, 6-(propylpiperonyl)-butyl carbityl ether, etc., butylhydroxyanisole, dibutylhydroxytoluene, tocopherol as antioxidants. , γ-oryzanol, etc., as insecticides, pyrethroids such as the common name allethrin and its geometric and/or optical isomers, and as rodent extermination and repellents, α-naphthylthiourea, cycloheximide, etc., and disinfectants. The agents include salicylic acid, p-chloro-m-xylenol, 2-(4'-thiazoyl)benzimidazole, etc., and the preventive agents include α-bromosinnamic aldehyde, N-dimethyl-N-phenyl-
Examples include N'-(fluorodichloromethyl)thiosulfamide and the like. The pest repellent of the present invention in various forms thus prepared can be used in areas infested by pests where a repellent effect is required, such as crop cultivation fields, orchards, general households, grain warehouses, cafeteria kitchens, and furniture. It can be applied by placing, scattering, spraying, coating, pasting, etc. in closets, entrances, washrooms, etc., or by scattering, spraying, coating, etc. on animals and plants themselves. In addition, the insect repellent of the present invention can be used by coating, impregnating, dropping, kneading, etc. on a suitable sheet-like base material in advance, and then placing or pasting it on the desired location. You can also do it. Examples of sheet-like substrates used in this case include synthetic resin sheets such as polyethylene, polypropylene, nylon, polyvinyl chloride, polyvinylidene chloride, and polyester, animal and vegetable or inorganic fiber sheets (paper, cloth, nonwoven fabric, leather, etc.) , mixed sheets or blended fabrics of synthetic resins and inorganic fibers or powders, blended fabrics or nonwoven fabrics of the above synthetic resins and animal and plant fibers, foils or films of metals such as aluminum, stainless steel, zinc, etc., and seeds of the various sheets mentioned above. An example is a layered sheet. Furthermore, the pest repellent of the present invention can be applied to natural materials such as awls, furniture parts, etc.
Pre-coating, impregnating, dripping,
It is also possible to use it by retaining it by kneading or the like. The amount of the active ingredient compound in the pest repellent of the present invention and the amount of the repellent to be applied may be appropriately determined depending on the dosage form, application method, application location, etc., and are not limited to the above. When used in the form of a liquid such as a wettable powder, the active ingredient compound may be contained in an amount of 1 to 80% by weight, preferably 5 to 40% by weight, and preferably 1 to 50% by weight when used in the form of a solid such as a powder. is 2~
It is sufficient that the content is 20% by weight, and in the case of holding it in a sheet-like base material or furniture member, it is sufficient that the content is approximately 1/2 of the saturated impregnated amount of the base material, etc. In addition, as for the application amount of the pest repellent of the present invention, for example, in the case of application, the amount of the active ingredient compound per 1 cm 2 of area to be applied is about 0.001 mg or more, preferably about
The amount is preferably 0.001 to 0.05 mg, and when used as a solid or other form, it is appropriate that the active ingredient compound is present in an amount of about 1 mg or more per 1 m 3 of application space. Examples will be given below to explain the present invention in more detail. Example 1 The repellent effect of each compound represented by the following general formula [] against German cockroaches was investigated by the following method. i.e. 0.05 of each test compound
mg/cm 2 was impregnated into a circular piece of paper (diameter 11 cm), and one sugar cube was placed in the center of the circular paper (diameter 11 cm) and in the center of a control paper that was not impregnated with any test compound.
The amount of weight loss (edible amount) of each paper sugar cube after 3 days of placing them in a rearing box where 25 male and female adult German cockroaches are kept so as not to overlap each other (X mg
) is measured. The repellent effect of each test compound was determined by the amount of sugar cube reduction (edible amount) on the control paper (A
mg) as the standard, and is calculated according to the formula below. Repellent effect (%) = A (mg) - X (mg) / A (mg) ×
100 The results obtained were judged according to the following criteria and are shown in Table 1 below. …Repellent effect 90% or more… 〃 70-90% +… 〃 50-70% ±… 〃 30-50% −… 〃 30% or less
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
上記第１表より本発明において有効成分とする
化合物（供試化合物No.１〜130）は、いずれも優
れた忌避効果を有することが明らかである。
実施例 ２
上記有効成分化合物を用いて下記組成のローシ
ヨンの形態を有する本発明害虫忌避剤を製造す
る。
有効成分化合物 10ｇ
プロピレングリコール ５ｇ
ミリスチン酸イソプロピル ２ｇ
精製水 15ｇ
香料 微量
エタノール 全体を100ｇとする量
また上記有効成分化合物を配合しない以外は上
記と同様にして対照ローシヨンを製造する。更に
比較のため上記において有効成分化合物に代え前
記第１表記載の供試化合物No.ｗ及びｙの夫々を用
い同様にして比較ローシヨンを作成する。
得られた各ローシヨンにつき、アカイエカ雌成
虫の忌避効力試験を次の通り行なう。即ち本発明
ローシヨン又は比較ローシヨンを一方の腕に均一
に塗布（１ml）し、他方の腕に対照ローシヨンを
同様に塗布後、１時間及び６時間経過後に夫々の
腕をそれぞれアカイエカ雌成虫各20頭を入れたケ
ージに入れ、30分間静止吸血させ、その後各ケー
ジ内の蚊を麻酔後紙上で押しつぶし紙上血痕
の数で吸血虫の判定を行ない、対照ローシヨンを
用いた場合の血痕数を基準として、下式に従い各
供試ローシヨンの忌避効力を判断する。
忌避効果（％）＝（対照ローシヨン使用時血痕数）−
（供試ローシヨン使用時血痕数）／（対照ローシヨン使
用時血痕数）×100
得られた結果を下記基準により、第２表に表記
する。
…忌避効果 90％以上
… 〃 70〜90％
＋… 〃 50〜70％
±… 〃 30〜50％
−… 〃 30％以下[Table] From Table 1 above, it is clear that the compounds used as active ingredients in the present invention (test compounds No. 1 to 130) all have excellent repellent effects. Example 2 A pest repellent of the present invention in the form of a lotion having the following composition is produced using the above active ingredient compound. Active ingredient compound 10g Propylene glycol 5g Isopropyl myristate 2g Purified water 15g Fragrance Trace amount of ethanol Amount to make the whole 100g A control lotion is produced in the same manner as above except that the above active ingredient compound is not blended. Furthermore, for comparison, comparative lotions were prepared in the same manner as described above using test compounds Nos. w and y listed in Table 1 above in place of the active ingredient compounds. Each of the obtained lotions was tested for repellency against adult female Culex pipiens as follows. That is, the lotion of the present invention or the comparison lotion was uniformly applied (1 ml) to one arm, and the control lotion was similarly applied to the other arm. After 1 hour and 6 hours had elapsed, each arm was treated with 20 adult Culex pipiens. The mosquitoes in each cage were placed in a cage containing a lotion and allowed to suck blood for 30 minutes, and then the mosquitoes in each cage were anesthetized and crushed on paper to determine whether they were blood sucking insects based on the number of bloodstains on the paper. Determine the repellent efficacy of each test lotion according to the formula below. Repellent effect (%) = (number of bloodstains when using control lotion) -
(Number of bloodstains when using the test lotion)/(Number of bloodstains when using the control lotion) x 100 The obtained results are shown in Table 2 according to the following criteria. …Repellent effect 90% or more… 〃 70-90% +… 〃 50-70% ±… 〃 30-50% −… 〃 30% or less
【表】【table】
【表】
実施例 ３
純毛の布（10cm×10cm）に下記供試化合物を
0.01mg／cm2の割合で含浸させ、これを無含浸布と
１対として、コイガ幼虫30頭を入れた直径30cmの
シヤーレ内に並べて入れ、７日間放置後、各布の
食害の程度を調べ、無含浸布の喫食量を基準とし
て各供試化合物の忌避効果を次式により算出す
る。
忌避効果（％）＝対照布喫食量（mg）−供
試布喫食量（mg）／対照布喫食量（mg）×100
得られた結果を第１表と同様の基準に従い、下
記第３表に示す。[Table] Example 3 The following test compound was applied to a pure wool cloth (10cm x 10cm).
Impregnated at a rate of 0.01 mg/cm 2 , this was paired with an unimpregnated cloth and placed side by side in a 30 cm diameter shear containing 30 carp moth larvae, and after being left for 7 days, the degree of feeding damage on each cloth was examined. The repellent effect of each test compound is calculated using the following formula based on the amount of food consumed on unimpregnated cloth. Repellent effect (%) = Control fabric consumption (mg) - Sample fabric consumption (mg) / Control fabric consumption (mg) x 100 The obtained results are summarized in Table 3 below according to the same criteria as Table 1. Shown below.
【表】【table】
【表】
実施例 ４
円形紙（径５cm）に、下記各供試化合物を
0.05mg／cm2の割合で含浸させ、これを無含浸紙
と１対としその夫々に角砂糖各１個をのせ、アミ
メアリ200匹を入れたシヤーレ（径30cm）内に並
べ、10分間放置後、各紙上のアリ数を計数し、
無含浸紙上における数を基準として、下式に従
い各供試化合物の忌避効果を判定する。
忌避効果（％）＝無含浸紙上アリ数（匹）−
供試紙上アリ数（匹）／無含浸紙上アリ数（匹）×
100
得られた結果を第１表と同様の基準に従い、下
記第４表に示す。[Table] Example 4 Each of the following test compounds was placed on a circular paper (5 cm in diameter).
Impregnated at a rate of 0.05mg/cm 2 , pair this with non-impregnated paper, place one sugar cube on each, arrange them in a shear dish (diameter 30cm) containing 200 red-eared ants, and leave for 10 minutes. Count the number of ants on each paper,
Based on the number on non-impregnated paper, the repellent effect of each test compound is determined according to the following formula. Repellent effect (%) = Number of ants on unimpregnated paper (number of ants) -
Number of ants on test paper (number of ants) / Number of ants on non-impregnated paper (number of ants) ×
100 The results obtained are shown in Table 4 below according to the same criteria as in Table 1.
【表】【table】
【表】
実施例 ５
イエバエの餌に下記各供試化合物の0.1％及び
殺虫剤（「スミチオン」、住友化学工業株式会社製
有機リン系殺虫剤）の0.01％又は上記殺虫剤のみ
を夫々配合し、之等をイエバエ成虫雌雄各100頭
を入れた二つの飼育箱に夫々別々に入れ、１時間
後各箱内の誘殺ハエ数を計数し、殺虫剤のみを配
合した毒餌における結果（対照）を基準として、
各供試化合物の忌避効果を次式により算出する。
忌避効果（％）＝対照死虫数（頭）−
検体死虫数（頭）／対照死虫数（頭）×100
得られた結果を第１表と同様の基準に従い、下
記第５表に示す。[Table] Example 5 House fly bait was mixed with 0.1% of each of the following test compounds and 0.01% of an insecticide ("Sumithion", an organophosphorus insecticide manufactured by Sumitomo Chemical Co., Ltd.), or only the above insecticide, respectively. , etc. were placed separately in two breeding boxes containing 100 male and 100 male and female house flies, and after 1 hour, the number of attracted flies in each box was counted, and the results were compared with the poisoned bait containing only insecticide (control). As a standard,
The repellent effect of each test compound is calculated using the following formula. Repellent effect (%) = Control number of dead insects (heads) -
Number of dead insects in specimen (heads)/number of dead insects in control (heads) x 100 The results obtained are shown in Table 5 below, according to the same criteria as in Table 1.
【表】
実施例 ６
円形紙（径５cm）に下記各供試化合物0.01
mg／cm2を含浸させ、これと無含浸紙とを１対と
し、これらの夫々中央に白米をのせ、コクヌスト
モドキ成虫雄雌各10頭を入れてあるシヤーレ（直
径30cm）内に並べ、１時間放置後各紙上のコク
ヌストモドキの数を計え、無含浸紙における結
果を標準として実施例４と同様にして各供試化合
物を用いた場合の忌避効果を算出する。
得られた結果を下記第６表に示す。[Table] Example 6 0.01 of each of the following test compounds on circular paper (diameter 5 cm)
mg/cm 2 , make a pair of this and unimpregnated paper, place white rice in the center of each pair, arrange them in a siere (diameter 30 cm) containing 10 male and 10 male and female Coconut flora adults, and After standing for a period of time, the number of brown fleas on each paper was counted, and the repellent effect when each test compound was used was calculated in the same manner as in Example 4 using the results on non-impregnated paper as a standard. The results obtained are shown in Table 6 below.
【表】
実施例 ７
第７表記載の各供試化合物を夫々用いて下記組
成の油剤の形態を有する本発明害虫忌避剤を製造
する。
有効成分化合物 ５ｇ
エチルセロソルブ 20ｇ
無臭灯油 全量を100ｇとする量
同様にして有効成分化合物を含有しない対照油
剤及び有効成分化合物に代え前記第１表記載の供
試化合物No.ｅ及びｎの夫々同量を含有する比較油
剤を製造する。
かくして得られた各油剤を、入口内寸４cm×30
cmのベニヤ板製箱（内寸20×30×４cm）の各内壁
５面に供試化合物量約３mg／cm2となる量（対照油
剤にあつてはこれに相当する量）を噴霧塗布し、
得られた各箱を、チヤバネゴキブリ400匹を飼育
しているケース内に一夜（12時間）放置し、チヤ
バネゴキブリの上記箱内への侵入居住数を計数す
る。得られた結果より下記基準に従い、各油剤の
忌避効果を判定する。
〇…居住数 ０
＋… 〃 １〜４匹
… 〃 ５〜９匹
… 〃 10匹以上
結果を下記第７表に示す。[Table] Example 7 Using each of the test compounds listed in Table 7, an pest repellent of the present invention in the form of an oil having the composition shown below is produced. Active ingredient compound 5g Ethyl cellosolve 20g Odorless kerosene Amount to make the total amount 100g Similarly, in place of the control oil containing no active ingredient compound and the active ingredient compound, the same amount of each of test compounds No. e and n listed in Table 1 above. A comparative oil containing the following is produced. Each of the oils obtained in this way was
Spray and apply the test compound in an amount of approximately 3 mg/cm 2 (an equivalent amount for the control oil) on each of the five inner walls of a cm plywood box (inner dimensions 20 x 30 x 4 cm).
Each box obtained is left overnight (12 hours) in a case housing 400 German cockroaches, and the number of German cockroaches that have invaded and resided in the box is counted. Based on the obtained results, the repellent effect of each oil agent was judged according to the following criteria. 〃…Number of residents: 0 +… 〃 1 to 4 animals… 〃 5 to 9 animals… 〃 10 or more animals The results are shown in Table 7 below.
【表】
実施例 ８
上記第７表記載の各供試化合物を夫々用いて下
記組成の製剤の形態を有する本発明害虫忌避剤を
製造する。
有効成分化合物 ５ｇ
ポリオキシエチレンオレイルエーテル（15モ
ル） 10ｇ
水 全量を100ｇとする量
同様にして有効成分化合物を含有しない対照製
剤及び有効成分化合物に代え、前記第１表記載の
供試化合物No.ａ及びｕの夫々同量を含有する比較
製剤を製造する。
これらを直径15cmの円形紙に２ml滴下含浸さ
せ風乾し、本発明試料、対照試料及び比較試料を
得る。
縦30cm×横40cm×高さ20cmのベニヤ板製箱内に
ナメクジ50匹を放飼し、上記本発明試料又は比較
試料と対照試料とのそれぞれ２枚を上記ベニヤ板
製箱の底に並べて載置し、夫々の試料上に野菜ク
ズを入れたプラスチツク製シヤーレ（直径５cm×
高さ１cm）を夫々設置し、設置１日目及び３日目
の野菜クズ上のナメクジの数を計測する。
その結果ナメクジは本発明試料上に載置した野
菜クズの入つたシヤーレには全く近づかず、すべ
て、対照試料上に載置した野菜クズの入つたシヤ
ーレ内に存在しており、本発明試料がナメクジ忌
避効果を有することが明らかであつた。
実施例 ９
上記実施例８で用いた本発明の供試化合物の
夫々10ｇに香料微量、エチルセロソルブ20ml及び
無臭灯油の全体を150mlとする量を加え、これと
液化石油ガス及びジメチルエーテル混合物（50：
50容積比）の150mlとをエアゾール用耐圧缶（内
容400ml）に充填して噴射装置に取り付け密封し
てエアゾール剤の形態の本発明害虫忌避剤を得
る。
かくして得られた各エアゾール剤を用い、実施
例７と同様にしてチヤバネゴキブリに対する忌避
効果試験を行なつた所、第７表記載の結果と同等
の結果を得た。
実施例 10
実施例７で用いた本発明化合物夫々５ｇ、ニト
ロセルロース25ｇ、シンナー25ｇ及びジブチルフ
タレート２ｇを混合溶解して、塗料形態の本発明
害虫忌避剤を得る。
かくして得られた各塗料を用い、実施例７と同
様に忌避効果試験を行なつた所、第７表記載の結
果と同様の結果を得た。
実施例 11
実施例７で用いた本発明の供試化合物の夫々５
ｇ及び効力増強剤としてＮ―（２―エチルヘキシ
ル）―ビシクロ―〔２，２，１〕―５―ヘプテン
―２，３―ジカルボキシイミド５ｇをｎ―ヘキサ
ン１に希釈し、不織布（ポリエチレン―木綿
（３：１重量比）製、厚さ300μ、面積１m2）に、
供試化合物が30ｇとなるように含浸後乾燥して、
シート状形態の本発明害虫忌避剤を得る。
得られたシートを、入口内寸40cm×30cmのベニ
ヤ板製箱（内寸20×30×４cm）の各内壁５面に合
つた大きさに切断後貼り合せ、実施例７と同様に
忌避効果試験に供した所、第７表記載の結果とほ
ぼ同等の結果を得た。
実施例 12
実施例７で用いた本発明の供試化合物３重量
部、酸化ケイ素１重量部及びシクロドデカン96重
量部を充分に擂潰混合後、300Kg／cm2の加圧下に
10ｇ／錠に打錠し、錠剤の形態を有する本発明害
虫忌避剤を得る。
得られた錠剤を実施例７記載のベニヤ板製箱内
に各箱２錠づつ入れ、同様の忌避効果試験を行な
つた所略々同様の結果を得た。
実施例 13
実施例７で用いた本発明の供試化合物の夫々を
酸化ケイ素の同重量と充分撹拌混合後粉状化し
て、粉末状形態の本発明害虫忌避剤を得る。
得られた粉末各３ｇを布製袋に充填しその各１
袋を実施例12と同様にベニヤ板製箱内に入れ同様
の忌避効果試験に供した所、ほぼ同様の結果を得
た。
実施例 14
実施例７で用いた本発明の供試化合物６重量部
を２，４，６―トリイソプロピル―１，３，５―
トリオキサン94重量部と混合後約90℃で加熱溶解
した液中に、桐製板（15cm×150cm×２cm厚さ）
を浸漬し、15Kg／cm2で加圧処理して、木材重量の
約25％となる量の液を含浸させて害虫忌避剤保持
木材の形態の本発明害虫忌避剤を得る。
得られた各木材を用いて実施例７記載の箱と同
一寸法の箱を貼合せ作成し、この箱（有効成分保
持量約15ｇにつき同様の害虫忌避効果試験を行な
つた所ほぼ同様の結果を得た。
実施例15及び比較例
本発明有効成分化合物とISRAEL JOURNAL
OF ENTOMOLLGY，vol.XI，p25（1976）第５
表に記載の化合物（Code No.AP―228）［以下こ
れを単に比較化合物という］との害虫忌避効果を
次の通り比較した。
(1) チヤバネゴキブリに対する忌避効果の持続性
実施例１において、円形紙を40日間室温に放
置する以外は同様にして試験を行なつた。得られ
た結果は下記第８表の通りであり、本発明供試化
合物は40日後にも忌避効果が持続するのに対し、
比較化合物は持続性がないことが明らかである。[Table] Example 8 Using each of the test compounds listed in Table 7 above, a pest repellent of the present invention in the form of a formulation having the following composition is produced. Active ingredient compound 5g Polyoxyethylene oleyl ether (15 mol) 10g Water Amount to bring the total amount to 100g Similarly, in place of the control preparation containing no active ingredient compound and the active ingredient compound, test compound No. listed in Table 1 above was used. Comparative formulations containing the same amounts of each of a and u are prepared. A circular paper with a diameter of 15 cm is impregnated with 2 ml of these drops and air-dried to obtain a sample of the present invention, a control sample, and a comparative sample. Fifty slugs were released in a plywood box measuring 30 cm long x 40 cm wide x 20 cm high, and two samples each of the above-mentioned inventive sample or comparison sample and control sample were placed side by side on the bottom of the plywood box. , a plastic shear dish (diameter 5 cm x
1 cm in height), and the number of slugs on the vegetable scraps was counted on the first and third day of installation. As a result, the slugs did not approach the dish containing vegetable scraps placed on the sample of the present invention at all, and all slugs were present in the dish containing vegetable scraps placed on the control sample. It was clear that it had a slug repellent effect. Example 9 To 10 g of each of the test compounds of the present invention used in Example 8 above, a trace amount of fragrance, 20 ml of ethyl cellosolve, and an amount of odorless kerosene to bring the total to 150 ml were added, and this was mixed with a mixture of liquefied petroleum gas and dimethyl ether (50:
50 volume ratio) into an aerosol pressure-resistant can (content: 400 ml), which is attached to an injection device and sealed to obtain the pest repellent of the present invention in the form of an aerosol. Using each of the aerosols thus obtained, a repellent effect test against German cockroaches was conducted in the same manner as in Example 7, and results equivalent to those shown in Table 7 were obtained. Example 10 5 g of each of the compounds of the present invention used in Example 7, 25 g of nitrocellulose, 25 g of thinner, and 2 g of dibutyl phthalate are mixed and dissolved to obtain an insect repellent of the present invention in the form of a paint. Using each of the paints thus obtained, a repellent effect test was conducted in the same manner as in Example 7, and results similar to those shown in Table 7 were obtained. Example 11 5 of each of the test compounds of the present invention used in Example 7
g and 5 g of N-(2-ethylhexyl)-bicyclo-[2,2,1]-5-heptene-2,3-dicarboximide as a potency enhancer were diluted in 1 part of n-hexane, and a nonwoven fabric (polyethylene-cotton (3:1 weight ratio), thickness 300 μ, area 1 m 2 ),
After impregnation with 30g of the test compound, dry it.
A sheet-like pest repellent of the present invention is obtained. The obtained sheet was cut into a size that matched each of the five inner walls of a plywood box (inner dimensions 20 x 30 x 4 cm) with an entrance inner dimension of 40 cm x 30 cm, and then pasted, and a repellent effect test was conducted in the same manner as in Example 7. When subjected to the test, results almost equivalent to those shown in Table 7 were obtained. Example 12 3 parts by weight of the test compound of the present invention used in Example 7, 1 part by weight of silicon oxide, and 96 parts by weight of cyclododecane were thoroughly ground and mixed, and then placed under a pressure of 300 kg/cm 2
The pest repellent of the present invention in tablet form is obtained by compressing into 10 g/tablet. The obtained tablets were placed in the plywood boxes described in Example 7, 2 tablets in each box, and the same repellent effect test was conducted, and almost the same results were obtained. Example 13 Each of the test compounds of the present invention used in Example 7 is sufficiently stirred and mixed with the same weight of silicon oxide, and then pulverized to obtain a powdered pest repellent of the present invention. Fill 3g of each of the obtained powders into cloth bags and
The bag was placed in a plywood box in the same manner as in Example 12 and subjected to the same repellent effect test, and almost the same results were obtained. Example 14 6 parts by weight of the test compound of the present invention used in Example 7 was added to 2,4,6-triisopropyl-1,3,5-
A paulownia wood board (15cm x 150cm x 2cm thick) was mixed with 94 parts by weight of trioxane and heated to about 90°C.
The pest repellent of the present invention in the form of pest repellent-retaining wood is obtained by soaking the wood and applying a pressure treatment at 15 kg/cm 2 to impregnate the wood with a liquid in an amount of about 25% of the weight of the wood. A box with the same dimensions as the box described in Example 7 was laminated using each piece of wood obtained, and a similar pest repellent effect test was conducted on this box (approximately 15 g of active ingredient), and almost the same results were obtained. Example 15 and Comparative Example Active ingredient compound of the present invention and ISRAEL JOURNAL
OF ENTOMOLLGY, vol.XI, p25 (1976) No. 5
The pest repellent effect with the compound listed in the table (Code No. AP-228) [hereinafter simply referred to as the comparative compound] was compared as follows. (1) Sustainability of repellent effect against German cockroach A test was conducted in the same manner as in Example 1, except that the circular paper was left at room temperature for 40 days. The results obtained are shown in Table 8 below, and the test compound of the present invention maintains its repellent effect even after 40 days.
It is clear that the comparison compound is not persistent.
【表】
(2) アカイエカ雌成虫に対する低濃度での忌避効
果
実施例２において有効成分化合物の使用量を５
ｇとする以外は同様にして10時間後の忌避効果を
調べた。結果は第９表に示す通りであり、本発明
供試化合物は濃度が1/2になつても高い忌避効果
を奏するのに対し、比較化合物は低濃度では忌避
効果を奏し得ないことが判る。[Table] (2) Repellent effect on Culex female adults at low concentrations In Example 2, the amount of active ingredient compound used was 5
The repellent effect after 10 hours was examined in the same manner except that g. The results are shown in Table 9, and it can be seen that the test compound of the present invention exhibits a high repellent effect even at a concentration of 1/2, whereas the comparative compound cannot exhibit a repellent effect at a low concentration. .
【表】
(3) コイガ幼虫に対する忌避効果の持続性
実施例３において純毛の布を20日間室温に放置
する以外は同様にして忌避効果を調べた。結果は
第10表に示す通りであり、本発明供試化合物は20
日後も忌避効果が持続するのに対し、比較化合物
は忌避効果の持続性がないことが判る。[Table] (3) Sustainability of repellent effect against carp moth larvae The repellent effect was examined in the same manner as in Example 3, except that the pure wool cloth was left at room temperature for 20 days. The results are shown in Table 10, and the test compound of the present invention was 20
It can be seen that the repellent effect persists even after several days, whereas the comparative compound does not have a sustained repellent effect.
【表】
(4) アミメアリに対する忌避効果の持続性
実施例４において円形紙を10日間室温に放置
する以外は同様にして試験を行なつた。得られた
結果は第11表の通りであり、本発明供試化合物は
10日後にも忌避効果が持続するのに対し、比較化
合物は持続性がないことが判る。[Table] (4) Sustainability of repellent effect against red-eared ants A test was conducted in the same manner as in Example 4, except that the circular paper was left at room temperature for 10 days. The results obtained are shown in Table 11, and the test compound of the present invention is
It can be seen that the repellent effect persists even after 10 days, whereas that of the comparative compound does not persist.
【表】
(5) イエバエに対する忌避効果の持続性
実施例５において試料を７日間室温に放置する
以外は同様にして忌避効果を調べた。結果は第12
表に示す通りであり、本発明供試化合物は７日後
も忌避効果が持続するのに対し、比較化合物は忌
避効果の持続性がないことが判る。[Table] (5) Persistence of repellent effect against house flies The repellent effect was investigated in the same manner as in Example 5, except that the sample was left at room temperature for 7 days. The result is number 12
As shown in the table, it can be seen that the repellent effect of the test compound of the present invention continues even after 7 days, whereas the repellent effect of the comparative compound does not persist.
【表】
(6) コクヌストモドキ成虫に対する忌避効果の持
続性
実施例６において円形紙を10日間室温に放置
する以外は同様にして試験を行なつた。得られた
結果は第13表の通りであり、本発明供試化合物は
10日後にも忌避効果が持続するのに対し、比較化
合物は持続性がないことが判る。[Table] (6) Sustainability of repellent effect against adult shorthorn beetles A test was conducted in the same manner as in Example 6, except that the circular paper was left at room temperature for 10 days. The results obtained are shown in Table 13, and the test compound of the present invention is
It can be seen that the repellent effect persists even after 10 days, whereas that of the comparative compound does not persist.
【表】
(7) ナメクジに対する忌避効果の持続性
実施例８において円形紙を７日間室温に放置
後、試験する以外は同様にして忌避効果を調べ
た。
本発明供試化合物No.７と比較化合物とを試験し
た結果、ナメクジは本発明試料上に載置した野菜
クズ入シヤーレには全く近付かず、全て比較化合
物試料上及び対照試料上に載置した野菜クズ入シ
ヤーレ内に存在していた。
このことから、本発明供試化合物は７日後にお
いても忌避効果が持続するのに対し、比較化合物
では忌避効果に持続性のないことが判る。[Table] (7) Sustainability of repellent effect against slugs The repellent effect was examined in the same manner as in Example 8 except that the circular paper was left at room temperature for 7 days and then tested. As a result of testing the present invention test compound No. 7 and the comparative compound, the slugs did not approach the vegetable scraps-containing shear dish placed on the present invention sample at all, and all slugs were placed on the comparative compound sample and the control sample. It was present in a sialet with vegetable scraps. From this, it can be seen that the repellent effect of the test compound of the present invention continues even after 7 days, whereas the repellent effect of the comparative compound does not persist.
Claims (1)
の直鎖状アルケニル基もしくはアルキニル基を示
す。〕 で表わされる化合物を有効成分として含有するこ
とを特徴とする害虫忌避剤。[Claims] 1 General formula NCS(-CH 2 )- o COOR [In the formula, n is an integer of 1 to 5 and R is a carbon number of 3 to 6]
represents a linear alkenyl group or alkynyl group. ] An insect repellent characterized by containing a compound represented by the following as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1507380A JPS56110604A (en) | 1980-02-08 | 1980-02-08 | Injurious insect repellent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1507380A JPS56110604A (en) | 1980-02-08 | 1980-02-08 | Injurious insect repellent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56110604A JPS56110604A (en) | 1981-09-01 |
| JPH0134964B2 true JPH0134964B2 (en) | 1989-07-21 |
Family
ID=11878672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1507380A Granted JPS56110604A (en) | 1980-02-08 | 1980-02-08 | Injurious insect repellent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56110604A (en) |
-
1980
- 1980-02-08 JP JP1507380A patent/JPS56110604A/en active Granted
Non-Patent Citations (1)
| Title |
|---|
| ISRAEL JOURNAL OF ENTOMOLLGY=1976 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56110604A (en) | 1981-09-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2849826B2 (en) | Pest control composition | |
| JPS59204102A (en) | Insect pest repellent | |
| JP5404188B2 (en) | Pest repellent | |
| JPH0161081B2 (en) | ||
| JPH0363527B2 (en) | ||
| JPH0113444B2 (en) | ||
| JPH0231683B2 (en) | ||
| JP3284592B2 (en) | Black cockroach attractant | |
| JPS6249242B2 (en) | ||
| JPH0134964B2 (en) | ||
| JPS6249243B2 (en) | ||
| JPS625401B2 (en) | ||
| JPS6412241B2 (en) | ||
| JP6539077B2 (en) | German cockroach attractant preparation | |
| JPS6228923B2 (en) | ||
| JPH024202B2 (en) | ||
| JPS6228921B2 (en) | ||
| JP3235911B2 (en) | Pest repellent | |
| JPS6228922B2 (en) | ||
| JPH02282308A (en) | Insect pest control agent composition | |
| JP3213816B2 (en) | Pest-feeding enhancer and pest-feeding enhancer | |
| JPH0258241B2 (en) | ||
| JP3096777B2 (en) | Pest control substances and pest control materials | |
| JPH0338241B2 (en) | ||
| JPH0560441B2 (en) |