NO773034L - INSECTICIDES. - Google Patents
INSECTICIDES.Info
- Publication number
- NO773034L NO773034L NO773034A NO773034A NO773034L NO 773034 L NO773034 L NO 773034L NO 773034 A NO773034 A NO 773034A NO 773034 A NO773034 A NO 773034A NO 773034 L NO773034 L NO 773034L
- Authority
- NO
- Norway
- Prior art keywords
- synergist
- agent according
- nitro
- ether
- formula
- Prior art date
Links
- 239000002917 insecticide Substances 0.000 title claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 60
- 241000238631 Hexapoda Species 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- -1 propylcarboxyl residues Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 230000000749 insecticidal effect Effects 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 230000000895 acaricidal effect Effects 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- BNWJOHGLIBDBOB-UHFFFAOYSA-N myristicin Chemical compound COC1=CC(CC=C)=CC2=C1OCO2 BNWJOHGLIBDBOB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- UXPPDBVMSPAPCL-UHFFFAOYSA-N 1-prop-1-ynoxyprop-1-yne Chemical compound CC#COC#CC UXPPDBVMSPAPCL-UHFFFAOYSA-N 0.000 claims description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
- 150000001241 acetals Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- SBLJHJFELRVSEP-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) thiocyanate Chemical compound C1CC2(C)C(SC#N)CC1C2(C)C SBLJHJFELRVSEP-UHFFFAOYSA-N 0.000 claims description 3
- MCBMNHUQBBSTKY-UHFFFAOYSA-N 4-chloro-2-nitro-1-prop-2-ynoxybenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1OCC#C MCBMNHUQBBSTKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 3
- JLSPXOVSIVYMCY-UHFFFAOYSA-N (2,4-dichlorophenyl)methyl thiocyanate Chemical compound ClC1=CC=C(CSC#N)C(Cl)=C1 JLSPXOVSIVYMCY-UHFFFAOYSA-N 0.000 claims description 2
- HUUXUYOEJOMTMM-UHFFFAOYSA-N 1,3-dichloro-2-[4-[4-(2,6-dichlorophenyl)but-2-ynoxy]but-2-ynyl]benzene Chemical compound ClC1=CC=CC(Cl)=C1CC#CCOCC#CCC1=C(Cl)C=CC=C1Cl HUUXUYOEJOMTMM-UHFFFAOYSA-N 0.000 claims description 2
- SQUJYDFTMPTTLT-UHFFFAOYSA-N 1-prop-2-ynoxynaphthalene Chemical compound C1=CC=C2C(OCC#C)=CC=CC2=C1 SQUJYDFTMPTTLT-UHFFFAOYSA-N 0.000 claims description 2
- ZYVTYOMVFLAPLX-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl 1,3-benzodioxole-5-carboxylate Chemical compound CCCCOCCOCCOC(=O)C1=CC=C2OCOC2=C1 ZYVTYOMVFLAPLX-UHFFFAOYSA-N 0.000 claims description 2
- LYWGAMBMZYPENL-UHFFFAOYSA-N 4-bromo-6-(ethoxymethyl)-1,3-benzodioxole Chemical compound BrC1=CC(=CC2=C1OCO2)COCC LYWGAMBMZYPENL-UHFFFAOYSA-N 0.000 claims description 2
- VSBPRBXTUAKKSY-UHFFFAOYSA-N 5-(5-methyl-1,3-dioxan-4-yl)-1,3-benzodioxole Chemical compound CC1COCOC1C1=CC=C(OCO2)C2=C1 VSBPRBXTUAKKSY-UHFFFAOYSA-N 0.000 claims description 2
- PSDYVDORVSBOQW-UHFFFAOYSA-N 5-methoxy-6-nitro-1,3-benzodioxole Chemical compound C1=C([N+]([O-])=O)C(OC)=CC2=C1OCO2 PSDYVDORVSBOQW-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 claims description 2
- VUTJOFRTSPCQKH-UHFFFAOYSA-N [O-][N+](C1=C(CC#CCOCC#CCC(C=CC=C2)=C2[N+]([O-])=O)C=CC=C1)=O Chemical compound [O-][N+](C1=C(CC#CCOCC#CCC(C=CC=C2)=C2[N+]([O-])=O)C=CC=C1)=O VUTJOFRTSPCQKH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000006365 alkylene oxy carbonyl group Chemical group 0.000 claims description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 2
- PDBLJVROGRYXEU-UHFFFAOYSA-N benzo[g][1,3]benzodioxole Chemical compound C1=CC=CC2=C(OCO3)C3=CC=C21 PDBLJVROGRYXEU-UHFFFAOYSA-N 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- RYZZMYXTNUJGMU-UHFFFAOYSA-N dodecyl thiocyanate Chemical compound CCCCCCCCCCCCSC#N RYZZMYXTNUJGMU-UHFFFAOYSA-N 0.000 claims description 2
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical class N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 claims description 2
- IILYTGRXMMACQA-UHFFFAOYSA-N n,n-dimethyl-6-nitro-1,3-benzodioxol-5-amine Chemical compound C1=C([N+]([O-])=O)C(N(C)C)=CC2=C1OCO2 IILYTGRXMMACQA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 2
- VZVRUCLAELDOGW-UHFFFAOYSA-N 2-octylsulfinylpropylbenzene Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=CC=C1 VZVRUCLAELDOGW-UHFFFAOYSA-N 0.000 claims 1
- YNZIPXLLPFYDGM-UHFFFAOYSA-N 2-pent-4-ynylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCC#C)C(=O)C2=C1 YNZIPXLLPFYDGM-UHFFFAOYSA-N 0.000 claims 1
- HRDCVMSNCBAMAM-UHFFFAOYSA-N 3-prop-2-ynoxyprop-1-yne Chemical compound C#CCOCC#C HRDCVMSNCBAMAM-UHFFFAOYSA-N 0.000 claims 1
- CIFFBTOJCKSRJY-UHFFFAOYSA-N 3α,4,7,7α-tetrahydro-1h-isoindole-1,3(2h)-dione Chemical compound C1C=CCC2C(=O)NC(=O)C21 CIFFBTOJCKSRJY-UHFFFAOYSA-N 0.000 claims 1
- SNWQAKNKGGOVMO-UHFFFAOYSA-N 5-nitro-1,3-benzodioxole Chemical compound [O-][N+](=O)C1=CC=C2OCOC2=C1 SNWQAKNKGGOVMO-UHFFFAOYSA-N 0.000 claims 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 claims 1
- 239000000642 acaricide Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 15
- 239000013543 active substance Substances 0.000 description 14
- 241000255925 Diptera Species 0.000 description 12
- 238000010998 test method Methods 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 241000254173 Coleoptera Species 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 6
- 235000021186 dishes Nutrition 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 241000238657 Blattella germanica Species 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 241001124076 Aphididae Species 0.000 description 4
- 241001674044 Blattodea Species 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 241000238662 Blatta orientalis Species 0.000 description 3
- 229920000298 Cellophane Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- 241000721621 Myzus persicae Species 0.000 description 3
- 241000238675 Periplaneta americana Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000254113 Tribolium castaneum Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 244000052616 bacterial pathogen Species 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000256593 Brachycaudus schwartzi Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 2
- 239000005947 Dimethoate Substances 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 241000238834 Nauphoeta cinerea Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241000131101 Oryzaephilus surinamensis Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000016127 added sugars Nutrition 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000002688 persistence Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- 235000013618 yogurt Nutrition 0.000 description 2
- NUMYTLIHYKESKM-UHFFFAOYSA-N (4-nitrophenyl)methyl thiocyanate Chemical compound [O-][N+](=O)C1=CC=C(CSC#N)C=C1 NUMYTLIHYKESKM-UHFFFAOYSA-N 0.000 description 1
- LNXLNFVKXMCUCX-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1.C1OC=CO1 LNXLNFVKXMCUCX-UHFFFAOYSA-N 0.000 description 1
- XSXVIRBOVQWYMH-UHFFFAOYSA-N 2,4-dioxabicyclo[3.3.1]nona-1(9),5,7-triene Chemical class C1=CC(OCO2)=CC2=C1 XSXVIRBOVQWYMH-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- SPAMRUYRVYMHPV-UHFFFAOYSA-N 3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical class C1=CCCC2C(=O)NC(=O)C21 SPAMRUYRVYMHPV-UHFFFAOYSA-N 0.000 description 1
- JJKSMDWICYGRFR-UHFFFAOYSA-N 5-(1-ethoxy-2-nitropropyl)-1,3-benzodioxole Chemical compound C(C)OC(C(C)[N+](=O)[O-])C1=CC2=C(C=C1)OCO2 JJKSMDWICYGRFR-UHFFFAOYSA-N 0.000 description 1
- URSGPNDFPZJSGG-UHFFFAOYSA-N 5-(2-butan-2-yloxyethoxymethyl)-6-propyl-1,3-benzodioxole Chemical compound C1=C(COCCOC(C)CC)C(CCC)=CC2=C1OCO2 URSGPNDFPZJSGG-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
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- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- VIRNWPPPATVJEC-UHFFFAOYSA-N n-methyl-n-(trichloromethylsulfanyl)carbamoyl chloride Chemical compound ClC(=O)N(C)SC(Cl)(Cl)Cl VIRNWPPPATVJEC-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000010815 organic waste Substances 0.000 description 1
- 125000005543 phthalimide group Chemical class 0.000 description 1
- 229940081310 piperonal Drugs 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Insekticid middelInsecticide agent
Den foreliggende oppfinnelse vedrører et insekticid og akaricid middel som erkarakterisert vedat det inneholder forbindelsen med formel I The present invention relates to an insecticide and acaricidal agent which is characterized in that it contains the compound of formula I
og en eller flere forbindelser som synergiserer denne forbindelsen med formel I i sin insekticide virkning. and one or more compounds which synergize this compound with formula I in its insecticidal action.
Det er funnet et stort antall forskjellige forbindelser som synergiserer forbindelsen med formel I enten alene eller i blanding med andre forbindelser i dens insekticide virkning. Viktige grupper av slike synergister er: a) Metylendioksyforbindelser, særlig 1,3-metylendioksybenzoler som kan ha en eller flere substituenter. A large number of different compounds have been found which synergize the compound of formula I either alone or in admixture with other compounds in its insecticidal action. Important groups of such synergists are: a) Methylenedioxy compounds, especially 1,3-methylenedioxybenzenes which may have one or more substituents.
Foretrukne forbindelser av denne typen er metylendioksyforbinde-lsen med den generelle formelen II der R-^betyr hydrogen, lavere alkyl, lavere alkoksy, lavere alkenyl, lavere alkinyl, halogen eller nitro, R2hydrogen, Preferred compounds of this type are the methylenedioxy compound with the general formula II where R-^ denotes hydrogen, lower alkyl, lower alkoxy, lower alkenyl, lower alkynyl, halogen or nitro, R 2 hydrogen,
lavere alkenyl, lavere alkoksy, di-lavere alkylaraino, lavere alkoksy- lavere alkyl, poly-lavere alkylenoksy med 3-6 oksygen atomer i kjeden som kan være rettlinjet eller forgrenet og inneholde minst 4 karbonatomer, poly-lavere alkylenoksykarbonyl med 2 til 6 oksygenatomer i kjeden som kan være rettkjedet eller forgrenet inneholde minst 4 karbonatomer, eller lavere alkyl-sulfoksy-lavere alkyl og og R_ sammen med karbonatomene hvortil de er bundet danner en mettet seksring som kan ha et eller to oksygenatomer og kan være substituert med en eller to propylkarboksylrester og/eller lavere alkylrester. lower alkenyl, lower alkoxy, di-lower alkylaraino, lower alkoxy- lower alkyl, poly-lower alkyleneoxy with 3-6 oxygen atoms in the chain which may be straight or branched and contain at least 4 carbon atoms, poly-lower alkyleneoxycarbonyl with 2 to 6 oxygen atoms in the chain which may be straight-chain or branched contain at least 4 carbon atoms, or lower alkyl-sulfoxy-lower alkyl and and R_ together with the carbon atoms to which they are attached form a saturated six-ring which may have one or two oxygen atoms and may be substituted with one or two propyl carboxyl residues and/or lower alkyl residues.
Foretrukne forbindelser med formel II er eksempelvis: Acetaldehyd[2-(2-etoksyetoksy)-3,4-metylendioksyfenyl]acetal; 5,6,7,8-tetrahydro-7-metylnafto(2,3-d)1,3-dioksol]-5,6-dikarbon-syredipropylester; Preferred compounds of formula II are, for example: Acetaldehyde [2-(2-ethoxyethoxy)-3,4-methylenedioxyphenyl]acetal; 5,6,7,8-tetrahydro-7-methylnaphtho(2,3-d)1,3-dioxole]-5,6-dicarboxylic acid dipropyl ester;
piperonal-bis-[2-(2<1->n-butoksyetoksy)etyl]acetal; piperonal bis-[2-(2<1->n-butoxyethoxy)ethyl]acetal;
4-(3,4-metylendioksyfenyl)-5-metyl-l,3-dioksan; 4-(3,4-methylenedioxyphenyl)-5-methyl-1,3-dioxane;
1,2-metylendioksynaftalin; 1,2-methylenedioxynaphthalene;
4-nitro-l,2-metylendioskybenzol; 4-nitro-1,2-methylenedioscybenzene;
4-metoksy-5-nitro-l,2-metylendioksybenzol; 4-methoxy-5-nitro-1,2-methylenedioxybenzene;
4-dimetylamino-5-nitro-l,2-metylendioksybenzol; 4-dimethylamino-5-nitro-1,2-methylenedioxybenzene;
6-brom-4-etoksymetyl-l,2-metylendioksybenzol; 6-bromo-4-ethoxymethyl-1,2-methylenedioxybenzene;
4-(l-etoksy-2-nitropropyl)-1,2-metylendioksybenzol; 4-(1-ethoxy-2-nitropropyl)-1,2-methylenedioxybenzene;
myristicin (=5-allyl-l-metoksy-2,3-metylendioksybenzol); 4,5-metylendioksy-benzosyre-2-(2-butoksyetoksy)-etylester. myristicin (=5-allyl-1-methoxy-2,3-methylenedioxybenzene); 4,5-Methylenedioxy-benzoic acid 2-(2-butoxyethoxy)-ethyl ester.
Særlig foretrukne metylendioksyforbindelser er: Particularly preferred methylenedioxy compounds are:
a-[2-(2-butoks yetoksy)-etoksy]-4,5-(metylendioksy)-2-propyl-toluen og 1,2-(metylendioksy)-4-[2-(oktylsulfinyl)-propyl]-benzol. b) Propinyleter, særlig propinyloksyfenyl-, propinyloksybenzyl-og propinyloksynaftyl-etere som kan ha en eller flere substituenter. Foretrukket er propinyletere med den generelle formel III hvori R^betyr hydrogen, halogen eller nitro, R^og R,- hydrogen eller halogen, R^og R,, sammen med karbonatomet som det er bundet til danner en umettet seksring og X betyr gruppene -CH2- eller -N=CH-, hvorved i sistnevnte tilfelle'nitrogenatomet er forbundet med oksygenatomet og n betyr 0 eller 1. α-[2-(2-butoxy)-ethoxy]-4,5-(methylenedioxy)-2-propyl-toluene and 1,2-(methylenedioxy)-4-[2-(octylsulfinyl)-propyl]-benzene . b) Propynyl ethers, especially propynyloxyphenyl, propynyloxybenzyl and propynyloxynaphthyl ethers which may have one or more substituents. Preferred are propynyl ethers of the general formula III in which R^ means hydrogen, halogen or nitro, R^ and R, - hydrogen or halogen, R^ and R, together with the carbon atom to which it is bound form an unsaturated six-ring and X means the groups -CH2- or -N=CH-, whereby in the latter case the nitrogen atom is connected to the oxygen atom and n means 0 or 1.
Særlig foretrukne propinyletere er: 2-nitro-4-klorfenyl-2-propinyleter; Particularly preferred propynyl ethers are: 2-nitro-4-chlorophenyl-2-propynyl ether;
2,4,5-triklorfenyl-2-propinyleter; 2,4,5-trichlorophenyl-2-propynyl ether;
1- naftyl-2-propinyleter; 1-naphthyl-2-propynyl ether;
2- nitrobenzyl-2-propinyleter; 2-nitrobenzyl-2-propynyl ether;
a-naftylmetyl-2-propinyleter; α-naphthylmethyl-2-propynyl ether;
2,6-diklorbenzyl-2-propinyleter; 2,6-dichlorobenzyl-2-propynyl ether;
2,4-diklorbenzaldoksimin-2-propinyleter; 2,4-dichlorobenzaldoximine-2-propynyl ether;
1- naftaldoksimin-2-propinyleter; 1- naphthaldoximine-2-propynyl ether;
2- nitrobenzaldoksimin-2-propinyleter.2- nitrobenzaldoximine-2-propynyl ether.
i i c) Tiocyanater særlig substituerte metylentiocyanater som eksempelvis _J i i c) Thiocyanates especially substituted methylene thiocyanates such as _J
p-nitrobenzyltiocyanat isobornyltiocyanat isobornyltiocyanat p-nitrobenzyl thiocyanate isobornyl thiocyanate isobornyl thiocyanate
lauryltiocyanat oglauryl thiocyanate and
2,4-diklorbenzyltiocyanat.2,4-dichlorobenzyl thiocyanate.
d) Ftalimider og tetrahydroftalimider som for eksempel N-(2-etylheksyl)-5-norbornen-2,3-dikarboksimid, N-(2-butyl-heksyl)-(l-metyl-4-isopropyl-5-norbornen)-2,3-dikarboksimid og N-(4-fentinyl)-ftalimid. e) Polyklordialkyleter som for eksempel 3,3<1->heksaklor-2,2-diklor-dipropyleter. f) Arylproinylfosforsyreestere, særlig fenylpropinylalkyl-fosforsyreestere som for eksempel propyl-2-propinylfenylfosfat d) Phthalimides and tetrahydrophthalimides such as N-(2-ethylhexyl)-5-norbornene-2,3-dicarboximide, N-(2-butyl-hexyl)-(1-methyl-4-isopropyl-5-norbornene)- 2,3-dicarboximide and N-(4-fentinyl)-phthalimide. e) Polychlorodialkyl ether such as 3,3<1->hexachloro-2,2-dichloro-dipropyl ether. f) Arylproynyl phosphoric acid esters, especially phenylpropynylalkyl phosphoric acid esters such as propyl-2-propynylphenyl phosphate
og isobutyl-2-propinylfenylfosfonat.and isobutyl-2-propynylphenylphosphonate.
I de foran-stående formler omfatter de lavere alkylgrupper fortrinnsvis opptil 6 karbonatomer, hvorved alkylgruppene kan være rettlinjede eller forgrenede.. Særlig fortrukne alkylgrupper er metyl- og etylgrupper. De lavere alkylgrupper i de lavere alkenyl-, alkinyl-, alkylamino- og alkoksygrupper har likeledes opptil 6 karbonatomer. Foretrukne lavere alkylgrupper i disse restene er metyl- og etylgruppen. Uttrykket halogen omfatter de fire halogenatomer fluor~, klor, brom og jod når ikke annet er spesielt angitt. In the above formulas, the lower alkyl groups preferably comprise up to 6 carbon atoms, whereby the alkyl groups can be linear or branched. Particularly preferred alkyl groups are methyl and ethyl groups. The lower alkyl groups in the lower alkenyl, alkynyl, alkylamino and alkoxy groups likewise have up to 6 carbon atoms. Preferred lower alkyl groups in these residues are the methyl and ethyl groups. The term halogen includes the four halogen atoms fluorine, chlorine, bromine and iodine unless otherwise specifically stated.
Forbindelsen med formelen I er ny. Fremgangsmåten for fremstilling av denne forbindelsen erkarakterisert vedat man omsetter 2,2-dimetyl-4-hydroksyl-l,3-benzodioksyl med formelen med en forbindelse med den generelle formel The connection with formula I is new. The method for producing this compound is characterized by reacting 2,2-dimethyl-4-hydroxyl-1,3-benzodioxyl with the formula with a compound of the general formula
hvori Z beytr klor, brom eller jod, i nærvær av en base. wherein Z beytr chlorine, bromine or iodine, in the presence of a base.
Omsetningen av forbindelsen med formel II med en forbindelseThe reaction of the compound of formula II with a compound
med formel III skjer i og for seg ved kjente metoder, hensiktsmessig i nærvær av et overskudd av forbindelsen med formel III. Man arbeider gjerne i et inert organisk løsningsmiddel som hydro-karboner, for eksempel benzen eller toluen, klorerte hydro-karboner, for eksempel metylenklorid, etere, for eksempel di-etyleter-og liknende. Som katalysator kan anvendes baser, for eksempel kaliumkarbonat, natriumkarbonat, trietylamin, pyridin og liknende. Temperatur og trykk er ikke kritisk og man arbeider gjerne ved en temperatur mellom ca. 0° og tilbakeløpstemperaturen for reaksjonsblandingen, fortrinnsvis mellom romtemperatur og 130°C. with formula III takes place in and of itself by known methods, suitably in the presence of an excess of the compound of formula III. One usually works in an inert organic solvent such as hydrocarbons, for example benzene or toluene, chlorinated hydrocarbons, for example methylene chloride, ethers, for example diethyl ether and the like. Bases can be used as a catalyst, for example potassium carbonate, sodium carbonate, triethylamine, pyridine and the like. Temperature and pressure are not critical and you usually work at a temperature between approx. 0° and the reflux temperature for the reaction mixture, preferably between room temperature and 130°C.
1 detalj kan denne forbindelsen fremstilles som følger:1 detail, this compound can be prepared as follows:
5 g natriumhydrid (50%dispersjon i olje) utvaskes to ganger petroleter og oppslemmes så i en firehalsrundkolbe i 75 ml absolutt benzen. Hertil settes under" røring porsjonsvis 16,6 g (0/1 mol) 2,3-(iospropylidendioksy)fenol og blandingen røres 3 0 minutter ved romtemperatur. Deretter tildryppes 26,7 g N-triklormetyltio-N-metylkarbaminsyreklorid (friskt fremstilt) over et tidsrom på 1 time i benzenløsning (20 ml benzen).. Nå røres videre ved romtemperatur 4 timer under nitro-gen som beskyttelsesgass. Blandingen helles på isvann (200 ml) og ekstraheres 3 ganger med benzen. Benzenekstraktet vaskes 2 ganger med vann, tørkes over natriumsulfat, filtreres og inndampes. Man får 2,3-(isopropylidendioksy)fenylmetyl[tri-klormetyl)tio]karbamat i form av gule krystaller som etter omkrystallisasjon fra høytkokende petroleter smeltes ved 88 - 89°C. 5 g of sodium hydride (50% dispersion in oil) is washed out twice with petroleum ether and then suspended in a four-necked round flask in 75 ml of absolute benzene. 16.6 g (0/1 mol) of 2,3-(isopropylidenedioxy)phenol are added in portions while stirring and the mixture is stirred for 30 minutes at room temperature. Then 26.7 g of N-trichloromethylthio-N-methylcarbamic acid chloride (freshly prepared) are added dropwise over a period of 1 hour in benzene solution (20 ml benzene).. Now stir further at room temperature for 4 hours under nitrogen as protective gas. The mixture is poured onto ice water (200 ml) and extracted 3 times with benzene. The benzene extract is washed 2 times with water , dried over sodium sulfate, filtered and evaporated.2,3-(isopropylidenedioxy)phenylmethyl[trichloromethyl)thio]carbamate is obtained in the form of yellow crystals which, after recrystallization from high-boiling petroleum ether, melt at 88 - 89°C.
Det har vist seg at den insekticide virkning av forbindelsenIt has been shown that the insecticidal effect of the compound
med formel Iøkes vesentlig ved kombinasjon ifølge oppfinnelsen med synergister. Det resulterer i så vel en kvantitativ som kvalitativ forbedring av de insekticide egenskapene til forbindelsen med formel I. De ifølge oppfinnelsen synergiste insekticide midler og akaricide midler bevirker en raskere lammelse og en raskere og større dødelighet, slik at det nå with formula Is significantly increased by combination according to the invention with synergists. It results in both a quantitative and qualitative improvement of the insecticidal properties of the compound of formula I. The synergistic insecticidal agents and acaricidal agents according to the invention cause a faster paralysis and a faster and greater mortality, so that now
er mulig å bekjempe insekter med større hell enn tidligere.it is possible to fight insects with greater success than before.
Videre har de insekticide midler og akaricide midler ifølge oppfinnelsen den egenskap at de også besitter full virksom- Furthermore, the insecticidal agents and acaricidal agents according to the invention have the property that they also possess full activity
het mot i og for seg resistente insektstammer. En særlig fordel ved middelet i henhold til oppfinnelsen er den relativt lavt toksisitet overfor varmblodige dyr, særlig overfor patte-dyr. hot against inherently resistant strains of insects. A particular advantage of the agent according to the invention is its relatively low toxicity towards warm-blooded animals, especially towards mammals.
Mengdeforholdene av komponentene av de insekticide og akaricide midlene ifølge oppfinnelsen kan variere avhengig av anvendelses-formålet, anvendelsestypen, insektene som skal bekjempes og andre faktorer innen vide grenser. Det er dog hensiktsmessig å anvende 0,1 - 10 vektdeler synergist på en vektdel av forbindelsen med formel I. Fortrinnsvis anvendes et forhold på The quantity ratios of the components of the insecticidal and acaricidal agents according to the invention can vary depending on the purpose of application, the type of application, the insects to be combated and other factors within wide limits. However, it is appropriate to use 0.1 - 10 parts by weight of synergist on one part by weight of the compound of formula I. Preferably a ratio of
1:1 vektdeler.1:1 parts by weight.
Den totale konsentrasjonen av komponentene i det bruksferdige insekticide og akaricide midlet avhenger av applikasjonsformen og anvendelsestypen. De insekticide og akaricide midler ifølge oppfinnelsen kan finne anvendelse i form av konsentrater, granu-later eller sammen med bæremidler som sprayer,aerosoler eller pulvere. For visse formål kan det være fordelaktig å anvende emulsjoner, suspensjoner eller løsninger sammen med emulgerings-eller fuktemidler. Som bæremidler kommer for eksemple på tale: kritt, talkum, bentonit, kaolin, diatomjord, kiseljord, fullers-jord, kalk, gips, pulver eller mel av organiske avfallsprodukter etc. Generelt kan man fremstille de synergistiske insekticide og akaricide midler ifølge foreliggende oppfinnelse etter frem-gangsmåter som er beskrevet i Farm Chemicals, bind 128, side 52 og følgende. De insekticide og akaricide midler ifølge oppfinnelsen kan også inneholde andre tilsetninger som emulgatorer eller maskeringsreagenser og/eller ytterligere kjente insekticide aktive substaner. The total concentration of the components in the ready-to-use insecticidal and acaricidal agent depends on the form of application and the type of application. The insecticidal and acaricidal agents according to the invention can be used in the form of concentrates, granules or together with carriers such as sprays, aerosols or powders. For certain purposes, it may be advantageous to use emulsions, suspensions or solutions together with emulsifying or wetting agents. Examples of carriers include: chalk, talc, bentonite, kaolin, diatomaceous earth, diatomaceous earth, fuller's earth, lime, gypsum, powder or flour from organic waste products, etc. In general, the synergistic insecticidal and acaricidal agents according to the present invention can be prepared according to methods described in Farm Chemicals, volume 128, page 52 et seq. The insecticidal and acaricidal agents according to the invention may also contain other additives such as emulsifiers or masking reagents and/or further known insecticidal active substances.
De insekticide og akaricide midler ifølge oppfinnelsen kan fore-ligge i form av konsentrater som er egnet for lagring og trans-port. Slike konsentraterr.kan for eksempel inneholde 5 -. 90% The insecticidal and acaricidal agents according to the invention can be available in the form of concentrates which are suitable for storage and transport. Such concentrates can, for example, contain 5 -. 90%
av den synergistisk-virksomme kombinasjonen av virkestoffer. Disse konsentratene kan fortynnes med like eller forskjellige bærematerialer til konsentrasjonen som egner seg for praktisk bruk. I de bruksferdige midler kan for eksempel virkestoffkonsentrasjonen ligge på 2 - 75 vekt-% fortrinnsvis 5-50 vekt-%. Virkestoffkonsentrasjonen kan dog også være mindre eller større. of the synergistically effective combination of active substances. These concentrates can be diluted with the same or different carrier materials to the concentration suitable for practical use. In the ready-to-use agents, for example, the active ingredient concentration can be 2-75% by weight, preferably 5-50% by weight. However, the active ingredient concentration can also be lower or higher.
Midlene ifølge oppfinnelsen kan anvendes ifølge vanlige metoder mot insekter, skogmann og liknende, for eksempel ved hjelp av kontakt eller ved opptak med næringen. Midlene er virksomme mot de forskjelligste insekttyper, for eksempel mot Diptera, særlig mot representanter av familiene Muscidae, Culiciade, Simuliidae, Tabanidae>Calliphoridae, Oestridae, Ceratopogonidae som for eksempel Musea spp.,Stomoxys calcitrans, Haematobia irritans; Culec spp., Anopheles spp.; Simulium sppf; Tabanus spp.; Cochliomyia hominivorax, Lucilia spp. og Calliphora spp.; Hypoderma spp.; Culicoides spp.; Leptoconops spp.; Lepidoptera, for eksempel Plodia interpunctella, Ephestia kuehniella, Cadra cautell, Sitotroga cerealella, Heliothis virescens; eller Coleoptera, som Sitophilus granarius, Sitophilus oryzae, Oryzaephilus surinamensis, Oryzaephilus mercator, Tribolium con-fusus, Tribolium castaneum, Tribolium audax, Rhizopertha dominca, Trogoderma variabile; eller Orthoptera som Blattella germanica, Blatta orientalis, Periplaneta americana, Nauphoeta cinerea; The agents according to the invention can be used according to usual methods against insects, woodpeckers and the like, for example by means of contact or absorption with the food. The agents are effective against a wide variety of insect types, for example against Diptera, especially against representatives of the families Muscidae, Culiciade, Simuliidae, Tabanidae>Calliphoridae, Oestridae, Ceratopogonidae such as Musea spp., Stomoxys calcitrans, Haematobia irritans; Culec spp., Anopheles spp.; Simulium sppf; Tabanus spp.; Cochliomyia hominivorax, Lucilia spp. and Calliphora spp.; Hypoderma spp.; Culicoides spp.; Leptoconops spp.; Lepidoptera, for example Plodia interpunctella, Ephestia kuehniella, Cadra cautell, Sitotroga cerealella, Heliothis virescens; or Coleoptera, such as Sitophilus granarius, Sitophilus oryzae, Oryzaephilus surinamensis, Oryzaephilus mercator, Tribolium con-fusus, Tribolium castaneum, Tribolium audax, Rhizopertha dominca, Trogoderma variabile; or Orthoptera such as Blattella germanica, Blatta orientalis, Periplaneta americana, Nauphoeta cinerea;
•eller Hemiptera som Rhodnium prolixus, Cimex spp.; eller Homo-ptera som Myzus persicae; Psylla spp., Diaspididae som for eksempel Aonidiella aurantii, Coccidas som for eksempel Sais-setia coffeae, Pseudococciae som for eksempel Planococcus citri; eller Anoplura som for eksempel Haematopinus spp., Linognatus spp. og Pediculus humanum subspp.; eller Siphonaptera som for eksempel Xenopsylla cheopis, Ctenocephalides spp. Videre er •or Hemiptera such as Rhodnium prolixus, Cimex spp.; or Homo-ptera such as Myzus persicae; Psylla spp., Diaspididae such as Aonidiella aurantii, Coccidas such as Sais-setia coffeae, Pseudococciae such as Planococcus citri; or Anoplura such as Haematopinus spp., Linognatus spp. and Pediculus humanum subspp.; or Siphonaptera such as Xenopsylla cheopis, Ctenocephalides spp
midlene også virksommme mot forskjellige andre Arthropoder, for eksempel mot skogbjørn og midd. the agents are also effective against various other arthropods, for example against forest bears and mites.
I de følgende eksempler er resultatene fra biologiske forsøk oppstilt, slik de erholdes ved applikasjon av forskjellige kombinasjoner mot forsøksinsekter. In the following examples, the results from biological experiments are presented, as they are obtained when different combinations are applied against experimental insects.
Strukturformel og nomenklatur av de i påfølgende eksempler nevnte forbindelser: Structural formula and nomenclature of the compounds mentioned in subsequent examples:
EKSEMPEL 1 EXAMPLE 1
Forsøksinsekt: Musea domestica, husflué.Experimental insect: Musea domestica, house fly.
Forsøksmetode (enkel Adultizid-forsøk)Test method (simple Adultizid test)
Petriskåler (diameter 90 mm) behandles med en acetonisk løsning av preparater. Pr. petriskål plasseres ti 4 - 5 dager gamle hunnfluer av en multiresistent stamme og inkuberes ved 25°C og 60% relativ fuktighet. Ubehandlede og med acetonbehandlede petriskåler tjerner som kontroller. Forsøkets varighet: 24 timer. Petri dishes (diameter 90 mm) are treated with an acetone solution of preparations. Ten 4-5 day old female flies of a multiresistant strain are placed per petri dish and incubated at 25°C and 60% relative humidity. Untreated and acetone-treated Petri dishes ponds as controls. Duration of the experiment: 24 hours.
Resultatent uttrykkes som prosentuell reduksjon av antall overlevne fluer i sammenlikning med kontrollforsøkene. Results are expressed as a percentage reduction in the number of surviving flies compared to the control trials.
EKSEMPEL 2 EXAMPLE 2
Forsøksinsekt: Musea domestica, husflueExperimental insect: Musea domestica, house fly
Forsøksmetode (persistensforsøk på underlag som er vanlig Test method (persistence test on a surface that is common
i praksis., for eksempel i fjøs)in practice., for example in barns)
To plater av gips henholdsvis betong (grunnflate 70 cm 2) behandles med et som WP<X>med sukkertilsats formulert preparat (i praksis vanlig formulering, se eksempel 13 - 15) og inkuberes fra angitte tidsrom ved 26°C og 60% relativt luftfuktighet. Deretter plasseres på hvert plate 5 tre dager gamle hunnfluer av en multiresistent stamme og over-dekkes med en hullet plastikkpetriskål. Ubehandlede plater tjerner som kontroller. Two sheets of plaster or concrete (base area 70 cm 2 ) are treated with a preparation formulated as WP<X> with added sugar (in practice a common formulation, see examples 13 - 15) and are incubated from the specified time at 26°C and 60% relative humidity . Next, 5 three-day-old female flies of a multiresistant strain are placed on each plate and covered with a perforated plastic Petri dish. Untreated plates pond as controls.
Bedømmelsen skjer 24 timer etter begynnelsen. Resultatene uttrykkes som porsentuell reduksjon av overlevende antall fluer i sammenheng med kontrollforsøkene. The assessment takes place 24 hours after the beginning. The results are expressed as a percentage reduction of the surviving number of flies in the context of the control experiments.
EKSEMPEL 3 EXAMPLE 3
Forsøksinsekt: Musea domestica, husflueExperimental insect: Musea domestica, house fly
Forsøksmetode (Persistensforsøk i ammoniakkatmosfære som fore-kommer under praktiske betingelser i fjøs) Test method (Persistence test in an ammonia atmosphere that occurs under practical conditions in barns)
Filterpapir (100 cm 2 ) befuktes med et som WP x med sukkertilsats formulert preparat (eksempel 13 - 15), fuktes med 0,5 Filter paper (100 cm 2 ) is moistened with a preparation formulated as WP x with added sugar (examples 13 - 15), moistened with 0.5
ml vann og inkuberes 6 dager i en lukket flaske (1 000 cm 2) .ml of water and incubated for 6 days in a closed bottle (1,000 cm 2 ).
I flasken stilles dertil en liten boks med 5 ml i l%ig ammoni-akkløsning. Deretter legges filter<p>apirene i store skåler, A small box with 5 ml of 1% ammonia solution is placed in the bottle. Then the filter<p>apires are placed in large bowls,
og pr. skål plasseres ti 4 dager gamle hunnfluer av en multiresistent stamme. Skålene inkuberes ved romtemperatur. and per ten 4-day-old female flies of a multiresistant strain are placed in the dish. The dishes are incubated at room temperature.
Ubehandlede filterpapirer tjener som kontroller.Untreated filter papers serve as controls.
Bedømmelsen skjer etter 1 og 4 timer.The assessment takes place after 1 and 4 hours.
Resultatene uttrykkes som prosentuell reduksjon av antallet overlevende fluer i sammenlikning med kontrollforsøkene. The results are expressed as a percentage reduction in the number of surviving flies compared to the control experiments.
Xwetable powderXwetable powder
EKSEMPEL 4 EXAMPLE 4
Forsøksinsekt: Culex fatigans, husmyggTest insect: Culex fatigans, house mosquito
Forsøksmetode:Test method:
Filterpapier (100 cm 2 ) behandles med de som WP x formulerte preparater. Yoghurtbegere klees med de tørkede filterpapirene. Pr. beger plasseres 10 nylig forede hunnmygger, begerne lukkes med cellofan og inkuberes ved romtemperatur. Filter paper (100 cm 2 ) is treated with the preparations formulated as WP x. Line yogurt cups with the dried filter papers. 10 newly fed female mosquitoes are placed per cup, the cups are closed with cellophane and incubated at room temperature.
Ubehandlede filterpapir er tjener som kontroller. Bedømmelsen skjer 24 timer etter begynnelse. Untreated filter paper serves as a control. The assessment takes place 24 hours after the start.
Resultatene uttrykkes som prosentuell reduksjon av antallet overlevende mygg i s ammen likning_m.ed kontrollforsøkene. The results are expressed as a percentage reduction in the number of surviving mosquitoes in the combined comparison_with the control experiments.
X wetable powderX wettable powder
EKSEMPEL 5 EXAMPLE 5
Forsøksinsekt; Anopheles stephensi, malariamygg Forsøksmetode: Filterpapier (100 cm 2) behandles med de som WP formulerte preparater. Yoghurtbegere klees med de tørkede filterpapirene. Pr. beger plasseres 10 nylig forede hunnmygger, begrene dekkes med cellofan og inkuberes ved romtepmeratur. Experimental insect; Anopheles stephensi, malaria mosquito Test method: Filter paper (100 cm 2 ) is treated with the preparations formulated as WP. Line yogurt cups with the dried filter papers. 10 newly fed female mosquitoes are placed per cup, the cups are covered with cellophane and incubated at room temperature.
Ubehandlede filgerpapirer tjerner som kontroller.Untreated filter papers tarn as controls.
Bedømmelsen skjer 4 timer etter begynnelsen.The assessment takes place 4 hours after the start.
Resultatene uttrykkes som prosentuell reduksjon av antallet overlevne mygg sammenliknet med kontrollforsøkene. The results are expressed as a percentage reduction in the number of surviving mosquitoes compared to the control trials.
EKSEMPEL6 EXAMPLE 6
Forsøksinsekt: Blattella germanica, tysk kakerlakk Forsøksmetode: Test insect: Blattella germanica, German cockroach Test method:
Filterpapirruller (64 cm 2) behandles med et acetonisk løsning av preparat og legges i petriskåler. Pr. petriskål plasseres] 5 kakerlakkhanner og inkuberes ved 25°C og 60% relativ luftfuktighet. Ubehandlede og med acetonbehandlede filterpapirer tjener som kontroller. Forsøkets varighet: 24 timer. Filter paper rolls (64 cm 2 ) are treated with an acetone solution of preparation and placed in Petri dishes. 5 cockroach males are placed per Petri dish and incubated at 25°C and 60% relative humidity. Untreated and acetone-treated filter papers serve as controls. Duration of the experiment: 24 hours.
Resultatene uttrykkes som prosentuell reduksjon av antallet overlevne kakerlakker sammenliknet med kontrollforsøkene. The results are expressed as a percentage reduction in the number of surviving cockroaches compared to the control trials.
EKSEMPEL 7 EXAMPLE 7
Forsøksinsekter:Experimental insects:
Blattella germanica ( B. G.), tysk kakerlakkBlattella germanica ( B. G.), German cockroach
Blatta orientalis ( B. o.), orientalsk kakerlakk Periplaneta americana ( P. a.), amerikansk kakerlakk Neuphoeta cinerea ( N. c.), grå kakerlakk Blatta orientalis ( B. o.), Oriental cockroach Periplaneta americana ( P. a.), American cockroach Neuphoeta cinerea ( N. c.), gray cockroach
I IN
Forsøksmetode; Experimental method;
Filterpapier (200 cm 2) behandles med de som WP formulerte preparater. Tørre filterpapir legges i tefloniserté cellofan-bokser. Pr. boks plasseres av hver kakerlakktype 5 adulte (hunner og hanner i blanding) og inkuberes ved romtemperatur. Filter paper (200 cm 2 ) is treated with the preparations formulated as WP. Dry filter paper is placed in Teflon-lined cellophane boxes. 5 adults of each cockroach type are placed per box (mixed females and males) and incubated at room temperature.
Ubehandlede filterpapirer tjener som kontroller.Untreated filter papers serve as controls.
Bedømmelsen skjer 24 timer etter begynnelse.-The assessment takes place 24 hours after the start.-
Resultatene uttrykkes som prosentuell reduksjon av antall overlevne kakerlakker sammenliknet med kontrollforsøkene. The results are expressed as a percentage reduction in the number of surviving cockroaches compared to the control trials.
EKSEMPEL 8 EXAMPLE 8
Forsøksinsekt: Rhodnium prolixus,Experimental insect: Rhodnium prolixus,
Forsøksmetode:Test method:
Filterpapirruller (64 cm 2) behandles med de som WP formulerte preparater og legges etter tørk i petriskålene. I hver skål plasseres 10 uforede adulte insekter og inkuberes ved romtemperatur . Filter paper rolls (64 cm 2 ) are treated with the preparations formulated as WP and, after drying, are placed in the Petri dishes. In each dish, 10 unlined adult insects are placed and incubated at room temperature.
Ubehandlede f ilterpapirer tjener som kontroller.Untreated filter papers serve as controls.
Bedømmelsen skjer 96 timer etter begynnelsen.The assessment takes place 96 hours after the beginning.
Resultatene uttrykkes som prosentuell reduksjon av antallet overlevne insekter sammenliknet med kontrollforsøkene. The results are expressed as a percentage reduction in the number of surviving insects compared to the control trials.
EKSEMPEL 9 EXAMPLE 9
Forsøksinsekt: Tribolium castaneum, rødbrun rismelbille Forsøksmetode:Petriskålebunner (diameter 90 mm) behandles med en acetonisk løsning av preparatet. Pr. skål plasseres 20 biller og inkuberes ved 25°C og 60% relativ luftfuktighet. Ubehandlede og med acetonbehandlede petriskåler tjerner som kontroller. For-søkets varighet: 48 timer. Test insect: Tribolium castaneum, reddish-brown rice flour beetle Test method: Petri dish bottoms (diameter 90 mm) are treated with an acetone solution of the preparation. 20 beetles are placed per dish and incubated at 25°C and 60% relative humidity. Untreated and acetone-treated Petri dishes ponds as controls. Duration of the pre-search: 48 hours.
Resultatene uttrykkes som prosentuell reduksjon av antall overlevne biller sammenliknet med kontrollforsøkene. The results are expressed as a percentage reduction in the number of surviving beetles compared to the control trials.
EKSEMPEL 10 EXAMPLE 10
Forsøksinsekter:Experimental insects:
Tribolium castaneum ( T. c.), rødbrun rismelbille Sitrophilus granarius ( S. g.), kornbille Tribolium castaneum ( T. c.), reddish-brown rice flour beetle Sitrophilus granarius ( S. g.), grain beetle
Sitrophilus oryzae (S.o.)/risbilleSitrophilus oryzae (S.o.)/rice beetle
Oryzaephilus surinamensis (O.s.), byggbilleOryzaephilus surinamensis (O.s.), barley beetle
Forsøksmetode:Test method:
Filterpapirruller (64 cm 2) behandles med en acetonisk løs-ning av.preparatet og legges etter tørking i petriskålen (diameter 90 mm). I hver skål plasseres 20 adulte midler (en skål for hver art) og inkuberes•ved 26°C og 55% relativ luftfuktighet. Filter paper rolls (64 cm 2 ) are treated with an acetone solution of the preparation and, after drying, are placed in the Petri dish (diameter 90 mm). In each dish, 20 adults are placed (one dish for each species) and incubated at 26°C and 55% relative humidity.
Ubehandlede og med acetonbehandlede filterpapirer tjener som kontroller. Untreated and acetone-treated filter papers serve as controls.
Bedømmelsen skjer 24 timer etter begynnelse.The assessment takes place 24 hours after the start.
Resultatene uttrykkes som prosentuell reduksjon av antallet overlevne biller sammenliknet med kontrollforsøkene. The results are expressed as a percentage reduction in the number of surviving beetles compared to the control trials.
EKSEMPEL 11 EXAMPLE 11
Forsøksinsekt: Myzus persicae, ferskenbladlusTest insect: Myzus persicae, peach aphid
Forsøksmetode: (enkel kurativforsøkmed ømfintlig bladlusstamme) Test method: (simple curative test with sensitive aphid strain)
Ertekim infiseres ved en blandingspopulasjon. De angrepene kimene behandles med en acetonisk løsning av preparatet og inkuberes ved 20°C og 60% relativ luftfuktighet. Pea germs are infected by a mixed population. The attacked germs are treated with an acetone solution of the preparation and incubated at 20°C and 60% relative humidity.
Ubehandlede og med aceton behandlede kimer tjener som kontroller. Forsøkets varighet: 48 timer. Untreated and acetone-treated germs serve as controls. Duration of the experiment: 48 hours.
Resultatene uttrykkes som prosentuell reduksjon av antallet overlevne bladlus sammenliknet med kontrollforsøkene. The results are expressed as a percentage reduction in the number of surviving aphids compared to the control trials.
EKSEMPEL. 12 EXAMPLE. 12
Forsøksinsekt: Myzus persicae, ferskenbladlusTest insect: Myzus persicae, peach aphid
Forsøksmetode: (kurativforsøk med ømfintlig og resistent Trial method: (curative trial with sensitive and resistant
bladlusstamme)aphid strain)
Kinesisk sennep infiseres med en blandingspopulasjon av ømfintlig (stamme 1), respektive en resistent bladlusstamme (stamme 2). De- angrepne plantene sprøytes med et sprøyte-brygg til de drypper. Inkubasjonen finner sted i et klimati-sert rom ved 20°C og 60% relativ luftfuktighet, 16 timer dag og 8 timer natt. Chinese mustard is infected with a mixed population of susceptible (strain 1) and a resistant aphid strain (strain 2). The infested plants are sprayed with a spray brew until they drip. Incubation takes place in an air-conditioned room at 20°C and 60% relative humidity, 16 hours day and 8 hours night.
Ubehandlede angrepne planter tjener som kontroller.Untreated infested plants serve as controls.
Etter 4 8 timer bedømmes forsøket.After 4-8 hours, the experiment is assessed.
Resultatene uttrykkes som prosentuell reduksjon av populsjonen i sammenlikning med kontrollforsøkene. The results are expressed as a percentage reduction of the population compared to the control trials.
EKSEMPEL 13 EXAMPLE 13
Virkestoffet med formel I og synergisten med formel A formuleres for biologiske prøver som følger: The active substance of formula I and the synergist of formula A are formulated for biological samples as follows:
EKSEMPEL 14 EXAMPLE 14
For den biologiske prøving anvendes handelspreparatet Sum v5^8 (virkestoffinnhold: 13% dimetoat, formel G) fra Dr. R. Maag AG, Dielsdorf. For the biological testing, the commercial preparation Sum v5^8 (active substance content: 13% dimethoate, formula G) from Dr. R. Maag AG, Dielsdorf is used.
EKSEMPEL 15EXAMPLE 15
Virkestoffet med formel H (klorpyrifos) formuleres som følge for biologisk prøving: The active substance with formula H (chlorpyrifos) is formulated as follows for biological testing:
EKSEMPEL 16 EXAMPLE 16
Virkestoff med formel I formuleres som følger for biologisk prøving: Active ingredient of formula I is formulated as follows for biological testing:
EKSEMPEL 17 EXAMPLE 17
Tilsvarende formulering i eksempel 16, men i stedet for 50% virkestoff med formel I anvendes 25% virkestoff med formel I + 25% synergist med formel A. Similar formulation in example 16, but instead of 50% active substance with formula I, 25% active substance with formula I + 25% synergist with formula A is used.
EKSEMPEL 18EXAMPLE 18
Tilsvarende formulering i eksempel 16, men i stedet for 50% virkestoff med formel I anvendes 50% synergist med formel A. Corresponding formulation in example 16, but instead of 50% active substance with formula I, 50% synergist with formula A is used.
EKSEMPEL 19EXAMPLE 19
Eor den biologiske prøving anvendes handelspreparatet Dedelo v5y(virkestoffinnehold: 75% DDT, formel i) fra Dr. R. Maag AG, Dielsdorf. For the biological testing, the commercial preparation Dedelo v5y (active substance content: 75% DDT, formula i) from Dr. R. Maag AG, Dielsdorf is used.
EKSEMPEL 20EXAMPLE 20
For den biologiske prøving anvendes handelspreparatet FamidV_y (virkestoffinnehold: 50% dioxakarb, formel J) fra Ciba- Geigy AG, Basel. For the biological testing, the commercial preparation FamidV_y (active ingredient content: 50% dioxacarb, formula J) from Ciba-Geigy AG, Basel is used.
EKSEMPEL 21 I EXAMPLE 21 I
Virkestoffet med formel I anvendes som følger for den biologiske prøving: The active ingredient of formula I is used as follows for the biological test:
EKSEMPEL 2 2 EXAMPLE 2 2
Tilsvarende formulering i eksempel 21, men i stedet for 250 g virkestoff med formel I anvendes 125 g virkestoff med formel I + 125 g synergist med formel A. Similar formulation in example 21, but instead of 250 g of active substance with formula I, 125 g of active substance with formula I + 125 g of synergist with formula A are used.
EKSEMPEL 2 3EXAMPLE 2 3
Tilsvarende formulering i eksempel 21, med i stedet for 250 g virkestoff med formel I anvendes 250 g synergist med formel A. Corresponding formulation in example 21, with instead of 250 g of active substance with formula I, 250 g of synergist with formula A is used.
EKSEMPEL 24EXAMPLE 24
For den bioloaiske prøvingen anvendes handelspreparatetPerfektion V_<y>(virkestoffinnhold: 40% dimetoat, formel G) fra Dr. R. Maag AG, Dielsdorf. For the biological testing, the commercial preparation Perfection V_<y> (active substance content: 40% dimethoate, formula G) from Dr. R. Maag AG, Dielsdorf is used.
EKSEMPEL 2 5 EXAMPLE 2 5
For fremstilling av et sprøytepulver (WP) som eksempelvis inneholder For the production of a spray powder (WP) which, for example, contains
25% 2,3-(isopropylidenoksy)fenyl-metyl[triklormetyl) tio]karbamat (virkestoff med formel I) 25% 2,3-(isopropylideneoxy)phenylmethyl[trichloromethyl)thio]carbamate (active substance with formula I)
25% 2-nitro-4-klorfenyl-2-propinyleter25% 2-nitro-4-chlorophenyl-2-propynyl ether
5% høydispergert kiselsyre,5% highly dispersed silicic acid,
1% natrium-laurylsulfat,1% sodium lauryl sulfate,
2% natrium-lignosulfonat (sulfat2% sodium lignosulphonate (sulphate
og and
42% kaolin42% kaolin
blandes disse komponentene og finmales i en egnet mølle. For fremstilling av den sprøyteferdige løsning røres pul-veret ut i den ønskede mengde vann. these components are mixed and finely ground in a suitable mill. To prepare the ready-to-spray solution, the powder is stirred into the desired amount of water.
Som foran beskrevet lar sprøytepulveret med alle virkestoff-blandinger seg fremstillg ifølge foreliggende oppfinnelse. As described above, the spray powder with all active ingredient mixtures can be prepared according to the present invention.
Claims (44)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CH1113276 | 1976-09-02 |
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NO773034L true NO773034L (en) | 1978-03-03 |
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NO773034A NO773034L (en) | 1976-09-02 | 1977-09-01 | INSECTICIDES. |
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JP (1) | JPS5352623A (en) |
AU (1) | AU2830377A (en) |
BE (1) | BE858327A (en) |
DE (1) | DE2738361A1 (en) |
DK (1) | DK390677A (en) |
FI (1) | FI772511A (en) |
FR (1) | FR2363283A1 (en) |
GB (1) | GB1585219A (en) |
IT (1) | IT1086007B (en) |
LU (1) | LU78067A1 (en) |
MC (1) | MC1163A1 (en) |
NL (1) | NL7709452A (en) |
NO (1) | NO773034L (en) |
NZ (1) | NZ185047A (en) |
SE (1) | SE7709863L (en) |
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EP0007398A1 (en) * | 1978-06-08 | 1980-02-06 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | N-thio-N-methyl carbamic acid derivative, process for its preparation, its application and pesticides containing it |
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1977
- 1977-08-18 IT IT26772/77A patent/IT1086007B/en active
- 1977-08-23 FI FI772511A patent/FI772511A/en not_active Application Discontinuation
- 1977-08-25 DE DE19772738361 patent/DE2738361A1/en not_active Withdrawn
- 1977-08-26 NL NL7709452A patent/NL7709452A/en not_active Application Discontinuation
- 1977-08-29 AU AU28303/77A patent/AU2830377A/en active Pending
- 1977-08-29 NZ NZ185047A patent/NZ185047A/en unknown
- 1977-08-30 FR FR7726302A patent/FR2363283A1/en active Granted
- 1977-09-01 BE BE180614A patent/BE858327A/en unknown
- 1977-09-01 MC MC771257A patent/MC1163A1/en unknown
- 1977-09-01 DK DK390677A patent/DK390677A/en unknown
- 1977-09-01 GB GB36550/77A patent/GB1585219A/en not_active Expired
- 1977-09-01 NO NO773034A patent/NO773034L/en unknown
- 1977-09-01 LU LU78067A patent/LU78067A1/xx unknown
- 1977-09-01 SE SE7709863A patent/SE7709863L/en unknown
- 1977-09-01 JP JP10537177A patent/JPS5352623A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
SE7709863L (en) | 1978-03-03 |
NL7709452A (en) | 1978-03-06 |
FI772511A (en) | 1978-03-03 |
JPS5352623A (en) | 1978-05-13 |
GB1585219A (en) | 1981-02-25 |
FR2363283A1 (en) | 1978-03-31 |
BE858327A (en) | 1978-03-01 |
DE2738361A1 (en) | 1978-03-09 |
MC1163A1 (en) | 1978-06-02 |
LU78067A1 (en) | 1978-10-17 |
IT1086007B (en) | 1985-05-28 |
AU2830377A (en) | 1979-03-08 |
FR2363283B1 (en) | 1980-06-13 |
NZ185047A (en) | 1980-08-26 |
DK390677A (en) | 1978-03-03 |
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