DK157679B - N-benzoyl-n'-phenoxyphenylurinstoffer, skadedyrsbekaempelsesmiddel og fremgangsmaade til bekaempelse af skadelige organismer - Google Patents
N-benzoyl-n'-phenoxyphenylurinstoffer, skadedyrsbekaempelsesmiddel og fremgangsmaade til bekaempelse af skadelige organismer Download PDFInfo
- Publication number
- DK157679B DK157679B DK049482A DK49482A DK157679B DK 157679 B DK157679 B DK 157679B DK 049482 A DK049482 A DK 049482A DK 49482 A DK49482 A DK 49482A DK 157679 B DK157679 B DK 157679B
- Authority
- DK
- Denmark
- Prior art keywords
- chlorine
- fluorine
- bromine
- methyl
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 239000000575 pesticide Substances 0.000 title description 5
- 239000004615 ingredient Substances 0.000 title 1
- 239000000460 chlorine Substances 0.000 claims abstract description 54
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 38
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 33
- 239000011737 fluorine Substances 0.000 claims abstract description 33
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 31
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 20
- 229910052794 bromium Inorganic materials 0.000 claims abstract 20
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 11
- 239000001257 hydrogen Substances 0.000 claims abstract 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 150000002367 halogens Chemical class 0.000 claims abstract 6
- 150000002431 hydrogen Chemical group 0.000 claims abstract 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 6
- QDEQNQGUBLZMEC-UHFFFAOYSA-N n-(phenoxycarbamoyl)-n-phenylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(C=1C=CC=CC=1)C(=O)NOC1=CC=CC=C1 QDEQNQGUBLZMEC-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 5
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 3
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 239000013543 active substance Substances 0.000 description 34
- -1 2-methyl-benzoyl Chemical group 0.000 description 28
- 239000000203 mixture Substances 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 235000013312 flour Nutrition 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000254173 Coleoptera Species 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- LLMLSUSAKZVFOA-UJURSFKZSA-N (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(O)=O LLMLSUSAKZVFOA-UJURSFKZSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- XLOPRKKSAJMMEW-SFYZADRCSA-M (R,R)-chrysanthemate Chemical compound CC(C)=C[C@@H]1[C@@H](C([O-])=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-M 0.000 description 3
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000122098 Ephestia kuehniella Species 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 241001674048 Phthiraptera Species 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009395 breeding Methods 0.000 description 3
- 230000001488 breeding effect Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical compound ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 241000238662 Blatta orientalis Species 0.000 description 2
- 241000255579 Ceratitis capitata Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000191839 Chrysomya Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241001425477 Dysdercus Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 241000256602 Isoptera Species 0.000 description 2
- 241000255777 Lepidoptera Species 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 241001402070 Sappaphis piri Species 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 241000897276 Termes Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 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
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- YOSCIBHNIINXGQ-UHFFFAOYSA-N (2,2-dimethyl-3H-1-benzofuran-7-yl) N-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2.CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 YOSCIBHNIINXGQ-UHFFFAOYSA-N 0.000 description 1
- ZAGNMMRDHSEOPE-UHFFFAOYSA-N (2-chlorophenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1Cl ZAGNMMRDHSEOPE-UHFFFAOYSA-N 0.000 description 1
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 description 1
- WBEJYOJJBDISQU-UHFFFAOYSA-N 1,2-Dibromo-3-chloropropane Chemical compound ClCC(Br)CBr WBEJYOJJBDISQU-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- KKFBZUNYJMVNFV-UHFFFAOYSA-N 1,2-bis(2-methylpropyl)naphthalene Chemical compound C1=CC=CC2=C(CC(C)C)C(CC(C)C)=CC=C21 KKFBZUNYJMVNFV-UHFFFAOYSA-N 0.000 description 1
- 229940100682 1,2-dibromo-3-chloropropane Drugs 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- WZXXZHONLFRKGG-UHFFFAOYSA-N 2,3,4,5-tetrachlorothiophene Chemical compound ClC=1SC(Cl)=C(Cl)C=1Cl WZXXZHONLFRKGG-UHFFFAOYSA-N 0.000 description 1
- QZEDXQFZACVDJE-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 QZEDXQFZACVDJE-UHFFFAOYSA-N 0.000 description 1
- 125000004098 2,6-dichlorobenzoyl group Chemical group O=C([*])C1=C(Cl)C([H])=C([H])C([H])=C1Cl 0.000 description 1
- ZRJSABISRHPRSB-UHFFFAOYSA-N 2,6-difluorobenzoyl isocyanate Chemical compound FC1=CC=CC(F)=C1C(=O)N=C=O ZRJSABISRHPRSB-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 1
- FSTQDWCIBNUNGP-UHFFFAOYSA-N 3-bromo-4-(4-fluorophenoxy)aniline Chemical compound BrC1=CC(N)=CC=C1OC1=CC=C(F)C=C1 FSTQDWCIBNUNGP-UHFFFAOYSA-N 0.000 description 1
- LLKFNPUXQZHIAE-UHFFFAOYSA-N 5-(3-aminopropyl)-8-bromo-3-methyl-2h-pyrazolo[4,3-c]quinolin-4-one Chemical compound O=C1N(CCCN)C2=CC=C(Br)C=C2C2=C1C(C)=NN2 LLKFNPUXQZHIAE-UHFFFAOYSA-N 0.000 description 1
- 241000238818 Acheta domesticus Species 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000253988 Acyrthosiphon Species 0.000 description 1
- 241000917225 Adelges laricis Species 0.000 description 1
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241000256176 Aedes vexans Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241001470785 Agrilus sinuatus Species 0.000 description 1
- 241001136249 Agriotes lineatus Species 0.000 description 1
- 241001031864 Agriotes obscurus Species 0.000 description 1
- 241000566547 Agrotis ipsilon Species 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 241001136525 Anastrepha ludens Species 0.000 description 1
- 241001256085 Anisandrus dispar Species 0.000 description 1
- 241000132163 Anopheles maculipennis Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241001600408 Aphis gossypii Species 0.000 description 1
- 241001095118 Aphis pomi Species 0.000 description 1
- 241000496365 Aphis sambuci Species 0.000 description 1
- 241000626570 Aporia Species 0.000 description 1
- 241001340598 Argyresthia conjugella Species 0.000 description 1
- 241001503477 Athalia rosae Species 0.000 description 1
- 241001174347 Atomaria Species 0.000 description 1
- 241001166626 Aulacorthum solani Species 0.000 description 1
- 241001367053 Autographa gamma Species 0.000 description 1
- 241001490249 Bactrocera oleae Species 0.000 description 1
- 241001629132 Blissus leucopterus Species 0.000 description 1
- 241000273316 Brachycaudus Species 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 241001414203 Bruchus lentis Species 0.000 description 1
- 241001414201 Bruchus pisorum Species 0.000 description 1
- 241001388466 Bruchus rufimanus Species 0.000 description 1
- 241001491664 Bupalus Species 0.000 description 1
- 241000259719 Byctiscus betulae Species 0.000 description 1
- RCGLOBFLNVGBBC-UHFFFAOYSA-N CCOCC(C)(C1=C(C(=CS1)C)C)OP(=O)(N)O Chemical compound CCOCC(C)(C1=C(C(=CS1)C)C)OP(=O)(N)O RCGLOBFLNVGBBC-UHFFFAOYSA-N 0.000 description 1
- 241000776777 Cacopsylla mali Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241001350371 Capua Species 0.000 description 1
- 241001130355 Cassida nebulosa Species 0.000 description 1
- 241001087583 Chaetocnema tibialis Species 0.000 description 1
- 241000426497 Chilo suppressalis Species 0.000 description 1
- 241001525905 Choristoneura murinana Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241001663467 Contarinia tritici Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000902369 Crioceris asparagi Species 0.000 description 1
- 241000256059 Culex pipiens Species 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- 241001634817 Cydia Species 0.000 description 1
- 241000969022 Dasineura Species 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 241000084475 Delia antiqua Species 0.000 description 1
- 241001585354 Delia coarctata Species 0.000 description 1
- 241001631712 Dendrolimus pini Species 0.000 description 1
- 241000489975 Diabrotica Species 0.000 description 1
- PGJBQBDNXAZHBP-UHFFFAOYSA-N Dimefox Chemical compound CN(C)P(F)(=O)N(C)C PGJBQBDNXAZHBP-UHFFFAOYSA-N 0.000 description 1
- SDKQRNRRDYRQKY-UHFFFAOYSA-N Dioxacarb Chemical compound CNC(=O)OC1=CC=CC=C1C1OCCO1 SDKQRNRRDYRQKY-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241001080889 Dociostaurus maroccanus Species 0.000 description 1
- 241001274799 Dreyfusia nordmannianae Species 0.000 description 1
- 241001274798 Dreyfusia piceae Species 0.000 description 1
- 241001425472 Dysdercus cingulatus Species 0.000 description 1
- 241000353522 Earias insulana Species 0.000 description 1
- 241000995027 Empoasca fabae Species 0.000 description 1
- 241001301805 Epilachna Species 0.000 description 1
- 241000060469 Eupoecilia ambiguella Species 0.000 description 1
- 241000515837 Eurygaster integriceps Species 0.000 description 1
- 241000953886 Fannia canicularis Species 0.000 description 1
- 241000720914 Forficula auricularia Species 0.000 description 1
- 241000255896 Galleria mellonella Species 0.000 description 1
- 241000257323 Glossina morsitans Species 0.000 description 1
- 241001232715 Granaria Species 0.000 description 1
- 241001441330 Grapholita molesta Species 0.000 description 1
- 241000241125 Gryllotalpa gryllotalpa Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241001466007 Heteroptera Species 0.000 description 1
- 241000291719 Hoplocampa minuta Species 0.000 description 1
- 241000257176 Hypoderma <fly> Species 0.000 description 1
- 241000546120 Ips typographus Species 0.000 description 1
- 241001300668 Jatropha integerrima Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000218194 Laurales Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 241000540210 Leucoptera coffeella Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 241000673175 Limonius californicus Species 0.000 description 1
- 241001261104 Lobesia botrana Species 0.000 description 1
- 241000254022 Locusta migratoria Species 0.000 description 1
- 241000193981 Loxostege sticticalis Species 0.000 description 1
- 241000257166 Lucilia cuprina Species 0.000 description 1
- 241000736227 Lucilia sericata Species 0.000 description 1
- 241001492180 Lygus pratensis Species 0.000 description 1
- 241000721696 Lymantria Species 0.000 description 1
- 241000721703 Lymantria dispar Species 0.000 description 1
- 241000255685 Malacosoma neustria Species 0.000 description 1
- 241000555300 Mamestra Species 0.000 description 1
- 241001422926 Mayetiola hordei Species 0.000 description 1
- 241000171293 Megoura viciae Species 0.000 description 1
- 241001478965 Melanoplus femurrubrum Species 0.000 description 1
- 241001394950 Melanotus communis (Gyllenhal, 1817) Species 0.000 description 1
- 241000254099 Melolontha melolontha Species 0.000 description 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- YNEVBPNZHBAYOA-UHFFFAOYSA-N Mexacarbate Chemical compound CNC(=O)OC1=CC(C)=C(N(C)C)C(C)=C1 YNEVBPNZHBAYOA-UHFFFAOYSA-N 0.000 description 1
- 241000952627 Monomorium pharaonis Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241001477931 Mythimna unipuncta Species 0.000 description 1
- 241000512856 Myzus ascalonicus Species 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- GASLMYXRWKVRNT-UHFFFAOYSA-N N-[[3-bromo-4-(4-fluorophenoxy)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound FC1=C(C(=O)NC(=O)NC2=CC(=C(C=C2)OC2=CC=C(C=C2)F)Br)C(=CC=C1)F GASLMYXRWKVRNT-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 241001671709 Nezara viridula Species 0.000 description 1
- 241001556089 Nilaparvata lugens Species 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000219830 Onobrychis Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241000975417 Oscinella frit Species 0.000 description 1
- 241001147397 Ostrinia Species 0.000 description 1
- 241001160353 Oulema melanopus Species 0.000 description 1
- 241000604373 Ovatus Species 0.000 description 1
- 241000118205 Ovicides Species 0.000 description 1
- 241000486438 Panolis flammea Species 0.000 description 1
- 241000562493 Pegomya Species 0.000 description 1
- 241000609952 Pemphigus bursarius Species 0.000 description 1
- 241001253326 Perkinsiella saccharicida Species 0.000 description 1
- 241001608567 Phaedon cochleariae Species 0.000 description 1
- 241001579681 Phalera bucephala Species 0.000 description 1
- 241001401863 Phorodon Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 241001439019 Phthorimaea operculella Species 0.000 description 1
- 241001227717 Phyllopertha horticola Species 0.000 description 1
- 241000517946 Phyllotreta nemorum Species 0.000 description 1
- 241000255969 Pieris brassicae Species 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 241000500439 Plutella Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241000254101 Popillia japonica Species 0.000 description 1
- 241000526145 Psylla Species 0.000 description 1
- 241000157279 Rhagoletis cerasi Species 0.000 description 1
- 241001136903 Rhagoletis pomonella Species 0.000 description 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- 241000254026 Schistocerca Species 0.000 description 1
- SZKKRCSOSQAJDE-UHFFFAOYSA-N Schradan Chemical compound CN(C)P(=O)(N(C)C)OP(=O)(N(C)C)N(C)C SZKKRCSOSQAJDE-UHFFFAOYSA-N 0.000 description 1
- 241001168723 Sitona lineatus Species 0.000 description 1
- 241000254181 Sitophilus Species 0.000 description 1
- 241000753145 Sitotroga cerealella Species 0.000 description 1
- 241000517830 Solenopsis geminata Species 0.000 description 1
- 241000277984 Sparganothis pilleriana Species 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000255626 Tabanus <genus> Species 0.000 description 1
- 241000255588 Tephritidae Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241000131345 Tipula <genus> Species 0.000 description 1
- 241001240492 Tipula oleracea Species 0.000 description 1
- 241000511627 Tipula paludosa Species 0.000 description 1
- 241001271990 Tomicus piniperda Species 0.000 description 1
- 241001238451 Tortrix viridana Species 0.000 description 1
- 241000254113 Tribolium castaneum Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 241001274787 Viteus Species 0.000 description 1
- 241001466330 Yponomeuta malinellus Species 0.000 description 1
- 241001136529 Zeugodacus cucurbitae Species 0.000 description 1
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002506 adulticidal effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000012615 aggregate Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- XEGGRYVFLWGFHI-UHFFFAOYSA-N bendiocarb Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)O2 XEGGRYVFLWGFHI-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- MDIQXIJPQWLFSD-NJGYIYPDSA-N cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(O)=O MDIQXIJPQWLFSD-NJGYIYPDSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical class CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007653 larval development Effects 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229960002809 lindane Drugs 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- YFBPRJGDJKVWAH-UHFFFAOYSA-N methiocarb Chemical compound CNC(=O)OC1=CC(C)=C(SC)C(C)=C1 YFBPRJGDJKVWAH-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- FPIMWYDJGNNHAF-UHFFFAOYSA-N methylcarbamoyloxy ethanimidothioate Chemical compound CNC(=O)OSC(C)=N FPIMWYDJGNNHAF-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000010742 number 1 fuel oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000017448 oviposition Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- 229940070846 pyrethrins Drugs 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 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
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
-
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
DK 157679B
Opfindelsen angår hidtil ukendte N-benzoyl-N'-phenoxy-phenylurinstoffer, bekæmpelsesmidler til skadelige organismer, der indeholder disse forbindelser som aktive stoffer, og en fremgangsmåde til bekæmpelse af skadelige 5 organismer.
Det er allerede kendt, at N-benzoyl-N1-phenylurinstoffer kan anvendes som insekticider (J. Agr. Food Chem. 21, 348 (1973); DE offentliggørelsesskrift nr. 25 31 202).
Den insekticide aktivitet af disse kendte N-benzoyl-N1 -10 phenylurinstoffer er dog utilfredsstillende.
Det er således opfindelsens formål at tilvejebringe N-benzoyl-N'-phenylurinstoffer, der udviser bedre insekticid aktivitet end de kendte N-benzoyl-N'-phenylurinstof fer.
15 N-benzoyl-N'-phenoxyphenylurinstofferne ifølge opfindel sen er ejendommelige ved det i den kendtegnende del af krav 1 angivne.
Opfindelsen angår endvidere et skadedyrsbekæmpelses-middel, der er ejendommeligt ved det i den kendeteg-20 nende del af krav 4 angivne.
Endelig angår opfindelsen en fremgangsmåde til bekæmpelse af skadelige organismer, hvilken fremgangsmåde er ejendommelig ved det i den kendetegnende del af krav 5 angivne.
25 Det har vist sig, at forbindelserne ifølge opfindelsen opfylder opfindelsens formål, idet de kan bekæmpe skadelige organismer, især insekter, på mere virksom måde end kendte N-benzoyl-N'-phenoxyphenylurinstoffer. Dette vil blive dokumenteret ved sammenlignings forsøg, der 30 figurerer senere i denne beskrivelse og som omfatter 2
DK 157679B
et stort antal urinstofderivater ifølge opfindelsen med stor variationsbredde hvad angår substituenterne R, Z, X og Y. Ued disse sammenligningsforsøg er der anvendt følgende sammenligningsforbindelser, der repræ-5 senterer den kendte teknik: A N-(2-methyl-benzoyl)-N'-[3-chor-4- Eksempel 3 fra (4-chlorphenoxy)-phenyl]-urinstof DE-A-25 31 302 B N-(2-chlor-benzoyl)-N1-[3-chlor-4- Eksempel 2 fra (4-chlorphenoxy)-phenyl]-urinstof DE-A-25 31 202 10 C N-(2,6-dichlorbenzoyl)-N'-[4- Eksempel 14 fra (4-chlorphenoxy)-phenyl]--urinstof Tabel III i J. Agr. Food, Chem. side 353
Som eksempler på den betydning af R, der omfatter en med chlor og/eller fluor substitueret alkoxygruppe med 1-4 carbonatomer, kan anføres: trifluormethoxy, 1,1,2,2-15 tetrafluorethoxy, difluormethoxy, 2-chlor2,1,1-trifluor- ethoxy og 1,1,2,3,3,3-hexafluorpropoxy, som eksempler på den betydning af R, der omfatter en alkylgruppe med 1-3 carbonatomer, skal anføres: methyl, ethyl, n-propyl og isopropyl, fortrinsvis methyl, og som eksempler på 20 den betydning af R, der omfatter en 2-hydroxyhexahalo- genisopropylgruppe, skal anføres: 2-hydroxyhexafluor-isopropylgruppen, 2-hydroxychlorpenta-fluorisopropyl-gruppen, 2-hydroxy-dichlortetrafluorisopropylgruppen og 2-hydroxytrichlortrifluorisopropylgruppen.
25 Foretrukne forbindelser med formel (I) er sådanne, i hvilke X er chlor i o-stilling og n er 1 eller X er chlor eller fluor i o-stilling og n er 2.
3
DK 157679B
N-benzoyl-N'-phenoxyphenylurinstofferne med formel I fremstilles ved, at man a) omsætter en forbindelse med formlen
__ R
(li)
Y Z
hvori Y, Z og R har de i krav 1 angivne betydninger, 5 med et benzoylisocyanat med formlen j^~^-CO-NCO (III)
Xn _ hvori X og n har de i krav 1 angivne betydninger, eller b) at man omsætter en forbindelse med formlen
R
QCN-^~^-0-^^ · (IV)
Y Z
hvori Y, Z og R har de i krav 1 angivne betydninger, med et benzamid med formlen (V)
V
10 hvori X og n har de i krav 1 angivne betydninger.
4
DK 157679B
Begge omsætninger gennemføres fortrinsvis i opløsningseller fortyndingsmidler. Som sådanne kommer praktisk talt alle indifferente organiske opløsningsmidler i betragtning. Hertil hører især aliphatiske og aromatiske, 5 eventuelt chlorerede eller nitrerede carbonhydrider, såsom benzen, chlorbenzener, benzin, carbontetrachlorid, 1,2-dichlorethan, methylenchlorid, nitromethan, cycliske og acycliske ethere, såsom diethylether, dibutylether, tetrahydrofuran og dioxan, acycliske og cycliske ketoner, 10 såsom acetone, methylethylketon, methylisopropylketon, cyclohexanon, desuden nitriler, såsom acetonitril og benzonitril. Også blandinger af disse opløsningsmidler kan anvendes.
Ved omsætning a) kan reaktionstemperaturen varieres 15 inden for et større område. Den ligger i reglen mel lem 0 og 80 °C, fortrinsvis mellem 20 og 60 °C. I dette foretrukne område forløber omsætningen uden yderligere afkøling. Ved omsætning b) kan temperaturen varieres mellem 20 og 160 °C, og fortrinsvis arbejder man ved 20 en temperatur mellem 80 og 130 °C.
Man lader i almindelighed omsætningen forløbe under normalt tryk.
Reaktionskomponenterne anvendes fortrinsvis i ækvimolært forhold. Et overskud af den ene eller den anden komponent 25 frembringer ingen væsentlige fordele. Omsætningen forløber praktisk talt kvantitativt.
Forbindelserne ifølge opfindelsen fremkommer sædvanligvis- i analyseren tilstand; i modsat fald kan de renses yderligere ved omkrystallisation. Elementæranalyse og 30 smeltepunkt tjener til karakterisering deraf.
Ved gennemførelse af fremgangsmådevarianten a) bringer
DK 157679 B
5 man hensigtsmæssigt det substituerede anilin med formel II til at foreligge sammen med opløsnings- eller fortyndingsmidlet, og derpå tilsættes en ækvimolær mængde af isocyanat med formlen III. Efter en reaktionstid 5 på flere timer, i reglen to timer, frasuges produktet,
eller reakt »ionsopløsningen befries fra opløsningsmiddel på en rotationsfordamper. Derpå tørres produktet under reduceret tryk. Ved fremgangsmådevariant b) andrager reaktionsvarigheden 2 til 6 timer. Pehoxyanilinerne 10 med formel II og benzoylisocyanaterne med formel III
lader sig fremstille i henhold til kendte metoder (J.
Org. Chem. 2J3, 1805 til 1811 (1963)); Weygand-Hilgetag, Organisch-Chemische Experimentierkunst, 4. oplag, J.A. Barth-Verlag, Leipzig, 1970, s. 374, 510 (ff). Amin-15 grupperne i forbindelserne med formel II kan i henhold til kendte metoder, f.eks. ved omsætning med phosgen, omdannes til isocyanatgruppen, hvorved man opnår forbindelserne med formel IV.
Fremstillinqseksempel 20 7,1 g 3-brom-4-(4-fluorphenoxy)-anilin opløses ved stue temperatur i 50 ml toluen. Derpå tildryppes 4,9 g 2,6-difluorbenzoylisocyanat, hvorved temperaturen stiger 15 °C. Derpå omrører man en time ved 50 QC, afkøler og suger bundfaldet fra. Man opnår 8,5 g N-(2,6-difluor-25 benzoyl)-N'-[4-(4-fluorphenoxy)-3-bromphenyl]-urinstof, smp. 162-164 °C (aktivt stof nr. 1).
Følgende forbindelser lader sig f.eks. fremstille analogt med ovennævnte fremgangsmåde a) eller i henhold til fremgangsmåde b): ~n y z 6
DK 157679B
nr. Y Z R smp. [°C] 2 2-F, 6-F Cl H 4-0CHF2 148-153 3 2-F, 6-F Cl H 4-0CD2CHClF 156-159 4 2-C1, 6-C1 Cl H 4-0CHF2 f 171-174 5 2-C1, 6-C1 Cl H 4-0CF2CHClF 129-139 6 2-C1 Cl H 4-0CF2CHClF 128-130 7 2-C1, 6-C1 Cl 3-C1 4-C1 240-242 8 2-C1 Cl 3-C1 4-C1 200-202 9 2-F, 6-F Cl 3-C1 4-C1 217-220 10 2-F Cl 3-C1 4-C1 186-187 11 2-F, 6-F Cl H 4-C(0H)(CC^)2170-185 12 2-C1 Cl H 4-C(0H)(CF3)2165-177 13 2-C1 Η H 4-0CF2-CHClF2169-173 14 2-F, 6-F Η H 4-0CF2-CHClF2184-186 15 2-C1 Cl H 4-Br 155-156 16 2-C1 Br H 4-F 162-164 17 2-C1, 6-C1 F H 4-CH^ 212-217 18 2-C1 F H 4-CH3 168-173 19 2-F, 6-F D H 4-CH? 195-200 20 2-F, 6-F N02 H 4-C1 196-200 21 2-C1 N02 H 4-C1 186-191 22 2-F, 6-F HH 4-0CHF2 214-216 23 2-F, 6-F Cl H 4-0CF2CHFCF3 144-146 24 2-F, 6-F H 3-C1 5-C1 220-225 25 2-C1, 6-C1 H 3-C1 5-C1 231-234 26 2-C1 H 3-C1 5-C1 223-226 27 2-C1, 6-F Cl H 4-0CHF2 125-133 28 2-F, 6-F Cl H 4-0CF2CF2H 140-142 29 2-C1 Cl H 4-0CF2CF2H 136-138 N-benzoyl-N'-phenoxyphenylurinstofferne med formel I ifølg-e opfindelsen er velegnede til på effektiv måde at bekæmpe skadelige organismer fra klassen omfattende insekter. De er velegnede adulticider og ovicider og 5 kan anvendes til plantebeskyttelse samt i hygiejne-, 7
DK 157679B
forrådsbeskyttelses- og veterinærsektoren som bekæmpelsesmidler til skadelige organismer.
Til de skadelige insekter hører fra ordenen omfattende sommerfugle (Lepidoptera) f.eks. Plutella maculi-5 pennis, Leucoptera coffeella, Hyponomeuta malinellus,
Argyresthia conjugella, Sitotroga cerealella, Phtho-rimaea operculella, Capua reticulana, Sparganothis pil-leriana, Cacoecia murinana, Tortrix viridana, Clysia ambiguella, Evetria buolina, Polychrosis botrana, Cydia 10 pomonella, Laspeyresia molesta, Laspeyresia funebrana,
Ostrinia nibilalis, Loxostege sticticalis, Ephestia kuehniella, Chilo suppressalis, Galleria Mellonella, Malacosoma neustria, Dendrolimus pini, Thaumatopoea pityocapa, Phalera bucephala, Chemimatobia brumata, 15 Hibernia defoliria, Bupalus piniarus, Agrotis segetum,
Agrotis ypsilon, Barathra brassica, Cirphis unipuncta, Prodenia litura, Laphygma exigu, Panolis flammea, Earias insulana, Plusia gamma, Albama argillacea, Lymantria dispar, Lymantria monocha, Pieris brassicae, Aporia 20 crataegi; fra ordenen omfattende biller (Coleoptera) f.eks. Bli-tophaga undata, Melanotus communis, Limonius californicus, Agriotes lineatus, Agriotes obscurus, Agrilus sinuatus, Meligthes aeneus, Atomaria linearis, Epilachna varives-25 tris, Phyllopertha horticola, Popillia japonica, Me- lolontha melolontha, Melolontha hippocastani, Amphi-mallus solstitialis, Crioceris asparagi, Lema melanopus, Leptinotarsa decemlineata, Phaedon cochleariae, Phyllo-treta nemorum, Chaetocnema tibialis, Phylloides chry-, 30 socephala, Diabrotica 12-punctata, Cassida nebulosa,
Bruchus lentis, Bruchus rufimanus, Bruchus pisorum,
Sitona lineatus, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Hylobies abietis, Byctiscus betulae, Athonomus grandia, Ceuthorrhyncnus assimilis, Ceuthorrhynchus
DK 157679 B
8 napi, Sitophilus granaria, Anisandrus dispar, Ips typographus, Blastophagus piniperda; fra ordenen omfattende de tovingede (Diptera) f.eks.
Lycoria pectoralis, Mayetiola destructor, Dasineura 5 brassicae, Contarinia tritici, Haplodiplosis equestris, Tipula paludosa, Tipula oleracea, Dacus cucurbitae,
Dacus oleae, Ceratitis capitata, Rhagoletis cerasi, Rhagoletis pomonella, Anastrepha ludens, Oscinella frit, Phorbia coarctata, Phorbia antiqua, Phorbia 10 brassicae, Pegomya hyoscyami, Anopheles maculipennis,
Culex pipiens, Aedes aegypti, Aedes vexans, Tabanus bovinus, Tipula paludose, Musca domestica, Fannia canicularis, Muscian stabulans, Glossina morsitans,
Oestrus ocis, Chrysomya macellaria, Chrysomya homini-15 vorax, Lucilia cuprina, Lucilia sericata, Hypoderma lineata; fra ordenen omfattende de årevingede (Hymenoptera) f.eks. Athalia rosae, Hoplocampa minuta, Monomorium pharaonis, Solenopsis geminata, atta sexdens; 20 fra ordenen omfattende væggelus (Heteroptera) f.eks.
Nezara viridula, Eurygaster integriceps, Blissus leu-copterus, Dysdercus cingulatus, Dysdercus intermedium, Piesma quadrata, Lygus pratensis; fra ordenen omfattende plantesugere (Homoptera) f.eks.
25 Perkinsiella saccharicida, Nilaparvata lugens, Empoa-sca fabae, Psylla mali, Psylla piri, Trialeurodos vapo-r-ar iorum, Aphis fabae, Aphis pomi, Aphis sambuci, Aphidula nastrutii, Cerosipha gossypii, Sappaphis mali, Sappaphis mala, Dysaphis radicola, Brachycaudus 30 cardui, Brevisoryne brassicae, Phorodon humili, Rhopa-lomyzus ascalonicus, Myzodes persicae, Hyzus cerasi, Dysaulacorthum pseudosolani, Acyrthosiphon onobrychis, 9
DK 157679B
Mscrosiphon rosae, Megoura viciae, Schizoneura lanuginosa, Pemphigus bursarius, Dreyfusia nordmannianae, Dreyfusia piceae, Adelges laricis, Viteus vitifolii; fra ordenen omfattende termitter (Isoptera) f.eks. Re-5 ticulitermes lucifugus, Calotermes flavicollis, Leuco- termes flavipes, Termes natalensis; og fra ordenen omfattende de retvingede (Orthoptera) f.eks. Forficula auricularia, Acheta domestica, Gryllotalpa gryllotalpa, Tachycines, asynamorus, Locusta migratoria, 10 Stauronotus maroccanus, Schistocerca peregrina, Nomodacris septemfasciata, Melanopuls spretus, Melano plus femur-rubrum, Blatta orientalis, Blattella germanica, Peri-planeta americana, Blabera gigantea.
De aktive stoffer kan anvendes som sådanne, i form af 15 formuleringer deraf eller i overensstemmelse med de dertil svarende anvendelsesmuligheder, f.eks. i form af direkte udsprøjtelige opløsninger, pulvere, suspensioner eller dispersioner, emulsioner, oliedispersioner, pastaer, pudringsmidler, udstrømningsmidler, granulater, 20 ved udsprøjtning, tågedannelse, forstøvning, udstrøning eller udhældning. Anvendelsesmulighederne retter sig helt efter anvendelsesformålene; de skal i hvert tilfælde sikre den finest mulige fordeling af de aktive stoffer ifølge opfindelsen.
25 Til fremstilling af direkte udsprøjtelige opløsninger, emulsioner, pastaer eller oliedispersioner kommer mineraloliefraktioner med middehøjt til højt kogepunkt, såsom petroleum eller dieselolie, desuden kultjæreolier samt olier af vegetabilsk eller animalsk oprindelse, 30 aliphatiske, cycliske og aromatiske carbonhydrider f.eks.
benzen, toluen, xylen, paraffin, tetrahydroriaphthalen, alkylerede napthaiener eller disses derivater, f.eks.
10
DK 157679B
methanol, ethanol, propanol, butanol, chloroform, te-trachlorkulstof, cyclohexanol, cyclohexanon, chlorbenzen, isophoron, stærkt polære opløsningsmidler, f.eks. di-methylformamid, dimethylsulfoxid , N-methylpyrrolidon, 5 vand, i betragtning.
Vandige anvendelsesformer kan fremstilles af emulsions-koncentrater, pastaer eller befugtelige pulvere (sprøjtepulvere, oliedispersioner) ved tilsætning af vand.
Til fremstilling af emulsioner, pastaer eller oliedis-10 persioner kan stofferne som sådanne eller opløst i en olie eller et opløsningsmiddel, homogeniseres i vand ved hjælp af befugtnings-, adhæsions-, dispergerings-eller emulgeringsmidler. Men man kan også fremstille koncentrater, der består af aktivt stof, befugtnings-, 15 adhæsions-, dispergerings- eller emulgeringsmiddel og eventuelt opløsningsmiddel eller olie, hvilke koncentrater er velegnede til fortynding med vand.
Som overfladeaktive stoffer kommer alkalimetal-, jord-alkalimetal-, ammoniumsalte af ligninsulfonsyre, naph-20 thalensulfonsyre, phenolsulfonsyre, alkylarylsulfona- ter, alkylsulfater, alkylsulfonater, alkalimetal- og jordalkalimetalsalte af dibutylnaphtalensulfonsyre, laurylethersulfat, fedtalkoholsulfater, fedtsyre, alkalimetal- og jordalkalimetalsalte, salte af sulfaterede 25 hexadecanoler, heptadecanoler, octadecanoler, salte af sulfaterede fedtalkoholglycolethere, kondensations-produkter af sulfoneret naphtalen og naphtalenderivater med formaldehyd, kondensationsprodukter af naphthalen eller naphthalensulfonsyrer med phenol og formaldehyd, 30 polyoxethylenoctylphenolether, ethoxyleret isooctylphenol, octylphenol, nonylphenol, alkylphenolpolyglycolether, tributylphenylpolyglycolether,alkylarylpolyetheralkoholer, isotridecylalkohol, fedt-alkoholethylenoxidkon-densator, ethoxyleret ricinusolie, polyoxyethylenal- 11
DK 157679B
kylethere, ethoxyleret polyoxypropylen, laurylalkohol-polyglycolertheracetal, sorbitester, lignin, sulfitaffaldslud og methylcellulose i betragtning.
Pulver-, udstrønings- og pudringsmidler kan fremstilles 5 ved blanding eller fælles formaling af de aktive stof fer med et fast bærestof.
Eksempler på formuleringer er: I. 3 vægtdele af forbindelse nr. 1 blandes grundigt med 97 vægtdele findelt kaolin. Man opnår på denne 10 måde et pu.dringsmiddel, der indeholder 3 vægt-% af det aktive stof.
II. 20 vægtdele af forbindelse nr. 14 opløses i en blanding, der består af 60 vægtdele cyclohexanon, 30 vægtdele isobutanol, 5 vægtdele af tillejrings- 13 produktet af 7 mol ethylenoxid til 1 mol isooc- tylphenol og 5 vægtdele af tillejringsproduktet af 40 mol ethylenoxid til 1 mol ricinusolie.
III. 80 vægtdele af forbindelse nr. 17 blandes godt med 3 vægtdele af natriumsaltet af diisobutyl- 20 naphthalen-alfa-sulfonsyre, 10 vægtdele af na triumsaltet af en ligninsulfonsyre fra en sulfitaffaldslud og 7 vægtdele pulverformig kisel-syregel og formales i en hammermølle.
Granulater, f.eks. omhyllings-, imprægnerings- og ho- 25 mogengranulater, kan fremstilles ved binding af de aktive stoffer til faste bærestoffer. Faste bærestoffer er f.eks. mineraljorder, såsom silicagel, kiselsyrer, kiselgeler, silicater, talkum, kaolin, attaler, kalksten, kalk, kridt, bolus, løss, ler, dolomit, diatomerjord, 30 calcium- og magnesiumoxid, formalede formstoffer, gød- 12
DK 157679B
ningsmidler, såsom f.eks. ammoniumsulfat, ammoniumphos-phat, ammoniumnitrat, urinstoffer og vegetabilske produkter, såsom kornmel, træbark-, træ- og nøddeskallemel, cellulosepulver og andre faste bærestoffer.
5 Formuleringerne indeholder i almindelighed mellem 0,1 og 95 vægt-?i aktivt stof, fortrinsvis mellem 0,5 og 90 vægt-?i.
Koncentrationen af aktivt stof i de anvendelsesfærdige præparater kan varieres inden for større områder. I 10 almindelighed ligger de mellem 0,0001 og 10 %, fortrinsvis mellem 0,01 og 1 %.
De aktive stoffer kan også med godt resultat anvendes ved ultra-lav-volumen-metoden (ULV), hvorved det muliggøres at udbringe formuleringer med over 95 vægt-15 % aktivt, stof eller endog det aktive stof uden addi tiver .
Den anvendte mængde af aktivt stof andrager under frilandsbetingelser mellem 0,02 og 10 kg/ha, fortrinsvis mellem 0,5 og 2,0 kg/ha.
20 Til de aktive stoffer kan man tilsætte olier af for skellig type, herbicider, fungicider, andre bekæmpelsesmidler mod skadevoldende organismer, baktericider, eventuelt også først umiddelbart før anvendelsen (tank-mix). Disse midler kan tilvejebringes til midlerne ifølge 25 opfindelsen i vægtforhold mellem 1:10 og 10:1.
F.eks. kan man tilblande følgende midler: 1,2-dibrom-3-chlorpropan, 1,3-dichlorpropen, 1,3-di-chlorpropen + 1,2-dichlorpropan, 1,2-dibrom-ethan, 2-sek.-butylphenyl-N-methylcarbamat, o-chlorphenyl-N-me-30 thylcarbamat, 3-isopropyl-5-methylphenol-N-methylcar-
DK 157679B
13 bamat, o-isopropoxypheny1-N-methylcarbamat, 3,5-dime-thyl-4-methylmercapto-phenyl-N-methylcarbamat, 4-di-methylamino-3,5-xylyl-N-methylcarbamat, 2-(l,3-dioxo-lan-2-yl)-pheny1-N-methy1-carbamat, 1-naphthyl-N-me-5 thylcarbamat, 2,3-dihydro-2,2-dimethyl-benzofuran-7-yl-N-methylcarbamat, 2,2-dimethyl-l,3-benzodioxol-4-yl-N-methylcarbamat, 2-dimethylamino-5,6-dimethyl-4-pyrimidinyl-dimethylcarbamat, 2-methyl-2-(methylthio)-proplonaldehyd-0-(methylcarbamoyl)-oxim, S-methyl-N-10 [(methylcarbamoyl)-oxy]-thio-acetimidat, methy1-N',N'- dimethyl-N-[(methylcarbamoyl)oxy]-1-thiooxamidat, N-(2-methyl-chlor-phenyl)-N',N'-dimethylformamidin, te-trachlorthiophen, l(2,6-difluor-benzoyl)-3-(4-chlor-phenyl)-urinstof, 0,0-dimethyl-0-(p-nitrophenyl)-phos-15 phorthioat, 0,0-diethyl-0-(p-nitropheny1)-phosphorthioat, 0-ethyl-0-(p~nitrophenyl)-phenyl-phosphonothioat, 0,0-dimethyl-0-(3-methyl-4-nitrophenyl)-phosphorthioat, 0,0-diethyl-0-(2,4-dichlorphenyl)-phosphortioat, 0-ethyl-0-(2,4-dichlorphenyl)-phenyl-phosphonothioat, 20 0,0-dimethyl-0-(2,4,5-trichlorphenyl)-ethyl-phospho- nothioat, 0,0-dimethyl-0-(4-brom-2,5-dichlorphenyl)-phosphorthioat, 0,0-dimethyl-0-(2,5-dichlor-4-jodphe-nyl)-phosphorthioat, 0,0-dimethyl-0-(3-methyl-4-methyl-thiophenyl)-phosphorthioat, 0-ethyl-0-(3-methyl-4-me-25 thylthiophenyl)-isopropyl-phosphoramidat, 0,0-diethyl- 0- [p-methylsulfinyl-phenyl]-phorphorthioat, 0-ethyl-S-phenyl-ethyl-phosphonodithioat, 0,0-diethyl-[2- chlor- 1- (2,4-dichlorphenyl)-vinyl]-phosphat, 0,0-di-methyl-[-2-chlor-l-(2,4,5-trichlorphenyl)]-vinyl-phosphat, 30 0,0-dimethyl-S-Cl'-phenyl)-ethylacetat-phosphordithioat, bis-(dimethylamino)-fluorphosphinoxid, octamethyl-pyro-phosphoramid,0,0-0,0-tetraethyldithio-pyrophosphat, S-chlormethyl-0,0-diethyl-phosphordithioat, 0-ethyl-S,S-dipropyl-phosphordithioat, 0,0-dimethyl0-2,2-di-35 chlorvinyl-phosphat, 0,0-dimethyl-l,2-dibrom2,2-dichlor- ethylphosphat, 0,0-dimethyl-2,2,2-trichlor-l-hydroxy- 14
DK 157679B
ethylphosphonat, 0,0-dimethyl-S-[l,2-biscarbethoxyethyl-(l)]phosphordithioat, 0-0-dimethyl-0-(l-methyl-2-carb-methoxy-vinyl)-phosphat, 0,0-dimethyl-5-(N-methyl-car-bamoyl-methyl)-phosphordithioat, 0,0-dimethyl-S-(N-5 methylcarbamoyl-methyl)-phosphorthioat, 0,0-dimethy1- S-(N-methoxyethyl-carbamoyl-methyl)-phosphordithioat, 0,0-dimethyl-S-(N-formyl-N-methyl-carbamoylmethyl)-phos-phordithioat, 0,Q-dimethyl-0-[l-methyl-2-(methyl-car-bamoyl)-vinyl]-phosphat, 0,0-dimethyl-0-[(l-methyl-2-10 dimethylcarbamoyl)vinyl]-phosphat, 0,0-dimethyl-0-[(l- methyl-2-chlor-2-diethylcarbamoyl)-vinyl]-phosphat, 0,0-diethyl-S-(ethylthio-methyl)-phosphordithioat, 0,0-diethyl-S-[(p-chlor-phenylthio)-methyl]-phosphordithioat, 0,0-dimethyl-S-(2-ethylthioethyl)phosphorthioat, 0,0-15 dimethyl-S-(2-ethylthioethy1)-phosphordithioat, 0,0- dimethyl-S-(2-ethylsulfinyl-ethy1)-phosphorthioat, 0,0-diethyl-S-(2-ethylthio-ethyl)-phosphordithioat, 0,0-diethyl-S-(2-ethylsulfinyl-ethyl)-phosphorthioat, 0,0-diethyl-thiophosphoryliminophenyl-acetonitril, 0,0-20 diethyl-S-(2-chlor-l.-phthalimidoethyl)-phosphor-dithioat, 0,0-diethyl-S-[6-chlor-benzoxazolon-(2)-yl-(3)]-methyl-dithiophosphat, 0,0-dimethyl-S-[2-methoxy-l,3,4-thia-diazol-5-[4H]-onyl-(4)-methyl]-phosphordithioat, 0,0-diethyl-0-[3,5,é-trichlorpyridyl-(2)]-phosphorthioat, 25 0,0-diethyl-0-(2-pyrazinyl)-phosphorthioat, 0,0-diethyl- 0-[2-isopropyl-4-methyl-pyrimidinyl-(6)]-phosphorthioat, 0,0-diethyl-0-[2-(diethylamino)-6-methyl-4-pyrimidi-nyl]-thionophosphat, 0,0-dimethyl-S-(4-oxo-l,2,3-ben-zotriazin-3-[4H]-yl-methyl)-phosphordithioat, 0,0-di-30 methyl-S-[(4,6-diamino-l,3,5-triazin-2-yl)-methyl]- phosphordithioat, 0,0-diethyl-(l-phenyl-l,2,4-triazol- 3-yl)-thionphosphat, 0,S-dimethyl-phosphor-amido-thioat, 0,S-dimethyl-N-acetyl-phosphor-amidothioat-hexachlor-cyclohexan, l,l-di(p-methoxyphenyl)-2,2,2-trichlor-ethan, 35 6,7,8,9,10,l0-hexachloro-l,5,5a,6,9,9a-hexahydro-6,9- 15
DK 157679B
methano-2,4-3-benzodioxa-thiepen-3-oxid, pyrethriner, DL-2-allyl-3-methyl-cyclopenten-(2)-on-(l)-yl-(4)-DL-cis,trans-chrysanthemat, 5-benzyl-furyl-(3)-methyl-DL-cis, trans-chrysanthemat, 3-phenoxybenzyl (+)-cis, trans-5 2,2-dimethyl-3-(2,2-dichlorvinyl)-cyclopropancarboxylat, a-cyano-3-phenoxybenzyl(+)-cis, trans-2,2-dimethyl-3-(2,2-dichlorvinyl)-cyclopropancarboxylat, (s)-a-cyano-3-phenoxybenzyl-cis(lR,3R)-2,2-dimethyl-3-(2,2-dibrom-vinyl)-cyclopropancarboxylat, 3,4,5,6-tetrahydrophthal-10 imidoethyl-DL-cis, trans-chrysanthemat, 2-methyl-5- (2-propiny1)-3-furylmethyl-chrysanthemat og (a-cyano- 3-phenoxybenzyl)-a-isopropyl-4-chlorphenylacetat.
De følgende eksempler dokumenterer den biologiske virkning af de nye forbindelser.
15 Nummereringen af de aktive stoffer svarer til den tabel lariske opstilling.
Eksempel 1
Opdrætningsforsøg med moskito-larver (Aedes aegypti).
200 ml ledningsvand blandes med præparater af aktivt 20 stof, der indeholder 10 vægt-% aktivt stof og 90 vægt-% af en emulgatorblanding af 10 vægt-% ethoxyleret ricinusolie, 20 vægt-% ethoyleret isooctylphenyl og 70 vægt-% cyclohexanon, og derpå pålægger man 30 til 40 aedes-larver i 4' stadium.
25 Forsøgstemperaturen andrager 25 °C. Man bedømmer for pupningen og de voksne individers udkrænkning fra puppel-hylsteret, hvorved en ubehandlet kontrol tjener som målestok. Under forsøgets varighed på 10 til 12 dage fodrer man en gang med et sædvanligt, pulverformigt 30 fiskefoder.
DK 157679 B
16
Ved dette forsøg viser de aktive stoffer nr. 1, 2, 3, 4, 6, 9, 11, 12, 14, 15, 16, 18, 19, 20, 22, 24, 26 og 27 en bedre virkning end sammenligningsmidlerne.
Dette fremgår af den følgende tabel.
Aktivt stof Koncentration af det Mortalitetsrate nr. aktive stof [ppm] [%] 1 0,05 100 2 0,01 100 3 0,1 100 4 0,02 100 6 0,1 100 9 0,04 100 11 0,02 100 12 0,08 100 14 0,02 100 15 0,05 100 16 0,1 100 18 0,5 100 19 0,2 100 20 0,2 100 22 0,02 100 24 0,004 100 26 0,4 100 27 0,1 100 A 1,0 100 A 0,5 4.50 B 0,1 100 B 0,04 <180 5 Eksempel 2
Opdrætningsforsøg med med stuefluer (Musca domestica) 50 g af et substrat af 100 dele vand 17
DK 157679B
10 dele bagerigær 10 dele tørmælk 1 del agar gennemblandes grundigt i varm tilstand med det vandige 5 præparat af en blanding af 10 vægt-% af det aktive stof og 90 vægt-?0 af en blanding af befugtningsmiddel og indifferent bæremateriale.
Efter afkølingen belægger man substratet med ca. 0,1 ml flueæg og iagttager udviklingen deraf over en uge.
10 Forsøgstemperaturen ligger ved 20 °C.
Ued dette forsøg viser de aktive stoffer nr. 11, 14, 22 og 27 en udmærket virkning, mens sammenligningsmidlerne er uvirksomme. Dette fremgår af den følgende tabel.
Aktivt stof Koncentration af det Virkning nr ._aktive stof [ppm]_[?□]_ s 11 25,0 Total hæmning 14 2,5 Total hæmning 22 5,0 Total hæmning 27 2,0 Total hæmning A 25,0 Uvirksom C 50,0 Uvirksom
Eksempel 3 15 Opdrætningsforsøg med middelhavsfrugtfluer (Ceratitis capitata) .
Forsøgene gennemføres i 100 ml formstofbægere, der er fyldt med 40 g af et substrat af gulerodspulver og vand (1:3) med gærtilsætning. Det aktive stof indføres som 20 vandigt præparat i den færdige grød, og denne podes med 100 til 200 friske æg. Bægrene opbevares i lukket tilstand ved 24 til 26 °C; efter ca. en uges forløb 18
DK 157679B
kan man bedømme udviklingen.
Ved dette forsøg viser de aktive stoffer nr. 2, 4 og 22 en stærkere virkning end sammenligningsmiddel A.
Eksempel 4 5 Opdrætningsforsøg med rismelbiller (Tribolium castaneum) 10 g hvedemel, der var grundigt blandet med 0,02 eller 0,5 mg aktivt stof, fyldes i 250 ml formstofflasker og belægges med 20 rismelbiller. Efter æglægningen (efter 14 dages forløb) sigter man billerne fra. Melet fyldes 10 tilbage i flaskerne og oplagres indtil udkrængningen af puppehylstret af den næste billegeneration ved +24°C.
Ved dette forsøg viser de aktive stoffer nr. 2, 4 og 6 en bedre virkning end sammenligningsmiddel A.
Eksempel 5 15 OpdTætnings forsøg med bomuldsvægge lus (Dysdercus inter- medius) 50 g bomuldssåsæd indføres med henblik på kvældning i 24 timer i det vandige præparat af aktivt stof af 10 vægt-% aktivt stof og 90 vægt-% af en emulgatorblan-20 ding af 10 vægt-% ethoxyleret ricinusolie, 20 vægt-% ethoxyleret isooctylphenol og 70 vægt-% cyclohexanon.
Den ovenstående væske hældes bort.
Derpå indfører man 20 væggelus i det næstsidste larvestadium i 1 liter glas, hvis bund er dækket med fugtigt 25 sand. Disse dyr får i 7 dage de forbehandlede frø som den eneste næring. Derpå tilbyder man dem ubehandlet foder.
19
DK 157679B
Man iagttager, om dyrene a) overlever og b) skifter hud, så de bliver voksne individer.
Ued dette forsøg viser det aktive stof nr. 38 en bedre 5 virkning end sammenligningsmidlerne. Dette fremgår af den følgende tabel.
Aktivt stof Koncentration af det Mortalitetsrate nr. aktive stof (ppm) (%) 22 1 100 A 25 100 A 1 Uvirksom B 10 100 B 4 Uvirksom C 25 Uvirksom
Eksempel 6
Opdrætningsforsøg med larver af melmøl (Ephestia kueh-niella) 10 Hvedemel, der i høj grad var belagt med æg af melmøl, blandes grundigt med de aktive stoffer. 10 g af dette mel indfyldes derpå i 250 ml glasflasker og oplagres ved 22 0C. Efter 4 ugers forløb bedømmer man larvernes udvikling.
15 Ved dette forsøg viser de aktive stoffer nr. 2, 4, 6 og 22 en stærk virkning.
Claims (5)
1. N-benzoyl-N'-phenoxyphenylurinstoffer, kendetegnet ved, at de har den almene formel B- /^^G0-NH-C0-NH-/^-0-^^ (I), η Y Z hvori 5. er chlor i 3-stilling, R er fluor, chlor, brom, en med chlor og/eller fluor substitueret alkoxygruppe med 1 til 4 carbonatomer, en alkylgruppe med 1 til 3 carbonatomer eller en 2-hy-droxyhexahalogenisopropylgruppe, hvorved halogen er 10 fluor og/eller chlor, Y er hydrogen, fluor, chlor eller brom, X er fluor, chlor eller brom, og n er 2 eller 3, hvorved substituenterne X er ens eller forskellige, 15 hvori Z desuden er hydrogen, når R er en med chlor og/eller fluor substitueret alkoxygruppe med 1 til 4 carbonatomer, en alkylgruppe med 1 til 3 carbonatomer eller en 2-hydroxyhexahalogenisopropylgruppe, 20 hvorved halogen er fluor og/eller chlor, Y er hydrogen, fluor eller chlor, X er fluor, chlor eller brom, og n er 1, 2 eller 3, hvorved substituenterne X er ens eller forskellige, 25 hvori Z desuden er hydrogen når DK 157679B R er fluor eller brom, V er chlor X er fluor, chlor eller brom, og n er 1, 5 hvori Y desuden er brom eller nitro, når R er fluor, chlor, brom, en med chlor og/eller fluor substitueret alkoxygruppe med 1 til 4 carbonatomer, en alkylgruppe med 1 til 3 carbonatomer eller en 2-hy-10 droxyhexahalogenisopropylgruppe, hvorved halogen er fluor og/eller chlor, Z er hydrogen eller chlor i m-stilling X er fluor, chlor eller brom, og n er 1, 2 eller 3, hvorved substituenterne X er ens 13 eller forskellige.
2. N-benzoyl-N'-phenoxyphenylurinstoffer med formel I ifølge krav 1, kendetegnet ved, at Z er hydrogen, X er chlor i o-stilling og n er 1.
3. N-benzoyl-N'-phenoxyphenylurinstoffer med formel 20 I ifølge krav 1, kendetegnet ved, at X er fluor eller chlor i o-stilling og at n er 2.
4. Skadedyrsbekæmpelsesmiddel, kendetegnet ved, at det indeholder et fast eller flydende bærestof og et N-benzoyl-N'-phenoxyphenylurinstof med formel 25. ifølge krav 1-3.
5. Fremgangsmåde til bekæmpelse af skadelige organismer, kendetegnet ved , at man lader en aktiv mængde af et N-benzoyl-N'-phenoxyphenylurinstof med formel I ifølge krav 1-3 påvirke de skadelige organismer eller 30 disses opholdssted.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3104407 | 1981-02-07 | ||
| DE19813104407 DE3104407A1 (de) | 1981-02-07 | 1981-02-07 | N-benzoyl-n'-phenoxyphenylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK49482A DK49482A (da) | 1982-08-08 |
| DK157679B true DK157679B (da) | 1990-02-05 |
| DK157679C DK157679C (da) | 1990-06-18 |
Family
ID=6124342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK049482A DK157679C (da) | 1981-02-07 | 1982-02-05 | N-benzoyl-n'-phenoxyphenylurinstoffer, skadedyrsbekaempelsesmiddel og fremgangsmaade til bekaempelse af skadelige organismer |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0057888B1 (da) |
| JP (1) | JPS57149261A (da) |
| AT (1) | ATE15892T1 (da) |
| DE (2) | DE3104407A1 (da) |
| DK (1) | DK157679C (da) |
| GR (1) | GR76991B (da) |
| IE (1) | IE52695B1 (da) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3217620A1 (de) * | 1982-05-11 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | 2,5-dihalogenbenzoyl-(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| ZA834768B (en) * | 1982-06-30 | 1984-03-28 | Union Carbide Corp | Novel pesticidal 1-(alkyl-phenoxyaryl)-3-benzoyl ureas and process for preparation |
| US4880838A (en) * | 1982-06-30 | 1989-11-14 | Rhone-Poulenc | Pesticidal 1-(4-Phenoxyphenyl)-5-Benzoyl urea compounds and process for preparation |
| DE3232265A1 (de) * | 1982-08-31 | 1984-03-01 | Basf Ag, 6700 Ludwigshafen | N-benzoyl-n'-phenoxyphenylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
| US5166179A (en) * | 1982-08-31 | 1992-11-24 | Arno Lange | N-benzoyl-N'-phenoxyphenylureas, their preparation and their use for controlling pests |
| US4540578A (en) * | 1982-12-30 | 1985-09-10 | Union Carbide Corporation | Pesticidal phenoxypyridyl benzoyl ureas |
| US4602109A (en) * | 1982-12-30 | 1986-07-22 | Union Carbide Corporation | Novel pesticidal phenoxyphenyl and phenoxypyridyl benzoyl ureas and process for preparation |
| AU572563B2 (en) * | 1983-02-09 | 1988-05-12 | Sumitomo Chemical Company, Limited | Benzoylureas |
| DK147084A (da) * | 1983-03-19 | 1984-09-20 | Bayer Ag | 1-phenyl-3-benzoyl-(thio)-urinstoffer, deres fremstilling og anvendelse som skadedyrsbekaempelsesmidler |
| US4873264A (en) * | 1983-05-20 | 1989-10-10 | Rhone-Poulenc Nederlands B.V. | Novel pesticidal 1-(alkyl-phenoxy-aryl)-3-benzoyl ureas and process for preparation |
| JPS6097949A (ja) * | 1983-10-31 | 1985-05-31 | Sumitomo Chem Co Ltd | ベンゾイル尿素誘導体，その製造法およびそれを有効成分として含有する殺虫剤 |
| CA1339745C (en) * | 1984-04-10 | 1998-03-17 | Martin Anderson | Pesticidal benzoylurea compounds |
| US4623658A (en) * | 1984-04-10 | 1986-11-18 | Shell Oil Company | Pesticidal benzoylurea compounds |
| DE3433152A1 (de) * | 1984-09-10 | 1985-04-11 | Celamerck Gmbh & Co Kg, 6507 Ingelheim | Insektizid wirksame kombinationen von benzoylharnstoff-derivaten mit 1,2-methylendioxybenzol-derivaten und gegebenenfalls pyrethrinen bzw. pyrethroiden |
| US4638088A (en) * | 1984-11-15 | 1987-01-20 | Union Carbide Corporation | Pesticidal biphenylyloxy and biphenylylalkoxy aryl acyl urea compounds |
| US5135953A (en) * | 1984-12-28 | 1992-08-04 | Ciba-Geigy | Use of acyl urea compounds for controlling endoparasites and ectoparasites of warm-blooded animals |
| JPS62502335A (ja) * | 1985-03-29 | 1987-09-10 | ユニオン カ−バイド コ−ポレ−シヨン | 農薬１−（４−フエノキシフエニル）−３−ベンゾイル尿素化合物と製造方法 |
| BR8606563A (pt) * | 1985-03-29 | 1987-08-04 | Union Carbide Corp | Compostos pesticidas de 1-(4-fenoxifenil)-3-benzoil-ureia e processo de preparacao dos mesmos |
| IL80174A0 (en) * | 1985-09-30 | 1986-12-31 | Union Carbide Corp | 1-(4-aryloxphenyl)-3-benzoyl urea derivatives,pesticidal compositions containing the same and process for the preparation thereof |
| DE3542201A1 (de) * | 1985-11-29 | 1987-06-04 | Basf Ag | N-benzoyl-,n'-phenoxyphenylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
| IT1215550B (it) * | 1987-06-05 | 1990-02-14 | Donegani Guido Ist | Benzoil-uree ad attivita'insetticida |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2531202C2 (de) * | 1975-07-12 | 1982-12-09 | Bayer Ag, 5090 Leverkusen | 2',4-Dichlor-4'-benzoylureido- diphenyläther, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
| DE3026825A1 (de) * | 1980-07-16 | 1982-02-18 | Basf Ag, 6700 Ludwigshafen | Substituierte n-benzoyl-n'-phenoxyphenylharnstoffe, ihre herstellung, ihre verwendung zur bekaempfung von bekaempfung von insekten und mittel dafuer |
-
1981
- 1981-02-07 DE DE19813104407 patent/DE3104407A1/de not_active Withdrawn
-
1982
- 1982-01-20 GR GR67060A patent/GR76991B/el unknown
- 1982-02-01 AT AT82100679T patent/ATE15892T1/de not_active IP Right Cessation
- 1982-02-01 DE DE8282100679T patent/DE3266596D1/de not_active Expired
- 1982-02-01 EP EP82100679A patent/EP0057888B1/de not_active Expired
- 1982-02-05 DK DK049482A patent/DK157679C/da active
- 1982-02-05 JP JP57016486A patent/JPS57149261A/ja active Pending
- 1982-02-05 IE IE261/82A patent/IE52695B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK49482A (da) | 1982-08-08 |
| IE820261L (en) | 1982-08-07 |
| EP0057888A2 (de) | 1982-08-18 |
| DE3266596D1 (en) | 1985-11-07 |
| DE3104407A1 (de) | 1982-08-19 |
| DK157679C (da) | 1990-06-18 |
| ATE15892T1 (de) | 1985-10-15 |
| EP0057888A3 (en) | 1983-01-26 |
| GR76991B (da) | 1984-09-04 |
| IE52695B1 (en) | 1988-01-20 |
| JPS57149261A (en) | 1982-09-14 |
| EP0057888B1 (de) | 1985-10-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0057888B1 (de) | N-Benzoyl-N'-phenoxyphenylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schädlingen | |
| US4508734A (en) | Substituted N-benzoyl-N-phenoxyphenylureas, the manufacture, and the use thereof for combating insects | |
| EP0008768B1 (de) | Aroylharnstoffe, Verfahren zu ihrer Herstellung sowie ihre Verwendung in insektiziden und akariziden Mitteln | |
| EP0056124B1 (de) | N-Benzoyl-N'-phenylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Insekten | |
| EP0074074B1 (de) | N-Benzoyl-N'-phenoxyphenylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Insekten | |
| EP0101990B1 (de) | N-Benzoyl-N'-phenoxyphenylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schädlingen | |
| EP0072438A2 (de) | N-Benzoyl-N'-phenylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Insekten und Spinnentieren | |
| US4855140A (en) | O-(O-ethyl-S-alkylphosphoryl)-O-(carbamyl)-pyrocatechol derivatives | |
| EP0084652B1 (de) | Oxadiazindione, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Insekten und Spinnentieren | |
| EP0069288B1 (de) | N-Benzoyl-N'-pyridylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schädlingen | |
| EP0073986B1 (de) | 3-Fluorphenyl-(di)thiophosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schädlingen | |
| US5166179A (en) | N-benzoyl-N'-phenoxyphenylureas, their preparation and their use for controlling pests | |
| DE3410543A1 (de) | Neue ester, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen | |
| US4405614A (en) | N-Sulfonylated thiolphosphoric ester amides and their use for controlling pests | |
| DE3542201A1 (de) | N-benzoyl-,n'-phenoxyphenylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen | |
| CA1305167C (en) | Bisthiolphosphates | |
| DE3722155A1 (de) | (n-benzoyl-n'-halogenalkoxycarbonylphenyl)-harnstoffe | |
| DE3519458A1 (de) | N-benzoyl-n'-(1,1-difluor-phenylmethyl)-phenylharnstoffe, verfahren zu ihrer herstellung und verwendung zur bekaempfung von schaedlingen | |
| DE3732541A1 (de) | N-benzoyl-n'-(4-(pyrazol-1-yl)-phenyl)- harnstoffe | |
| EP0037497A1 (de) | Pyrazol-5-yl-(thio)(thiol)phosphor(phosphon)säureester, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schädlingen | |
| DE3620021A1 (de) | Aldoximcarbamat, verfahren zu dessen herstellung und seine verwendung zur bekaempfung von schaedlingen | |
| DE3101956A1 (de) | N-alkyl-n-trialkylsilyl-carbamate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen | |
| DE3731561A1 (de) | N-benzoyl-n'-(2,3-dichlor-4-phenoxy)phenyl- harnstoffe | |
| DE3529126A1 (de) | Benzoesaeureester, verfahren zu ihrer herstellung und ihre verwendung zur schaedlingsbekaempfung | |
| DE3642466A1 (de) | N-benzoyl-n'-3,5-dichlor-2-fluor-4-(3-trifluormethyl)-phenoxyphenylharnstoffe, verfahren zu ihrer herstellung und verwendung zur bekaempfung von schaedlingen |