DK157294B - N-benzoyl-n'-phenylurinstoffer, insekticidt middel og fremgangsmaade til bekaempelse af insekter - Google Patents
N-benzoyl-n'-phenylurinstoffer, insekticidt middel og fremgangsmaade til bekaempelse af insekter Download PDFInfo
- Publication number
- DK157294B DK157294B DK010782A DK10782A DK157294B DK 157294 B DK157294 B DK 157294B DK 010782 A DK010782 A DK 010782A DK 10782 A DK10782 A DK 10782A DK 157294 B DK157294 B DK 157294B
- Authority
- DK
- Denmark
- Prior art keywords
- dimethyl
- methyl
- benzoyl
- diethyl
- phenyl
- Prior art date
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 241001671709 Nezara viridula Species 0.000 description 1
- 241001556089 Nilaparvata lugens Species 0.000 description 1
- 241000916006 Nomadacris septemfasciata Species 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
- 241001491877 Operophtera brumata Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241001147397 Ostrinia Species 0.000 description 1
- 241000604373 Ovatus Species 0.000 description 1
- 241000486438 Panolis flammea Species 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 241000562493 Pegomya Species 0.000 description 1
- 241000721454 Pemphigus Species 0.000 description 1
- 241000238675 Periplaneta americana Species 0.000 description 1
- 241001253326 Perkinsiella saccharicida Species 0.000 description 1
- 241001608568 Phaedon Species 0.000 description 1
- 241001579681 Phalera bucephala Species 0.000 description 1
- 241001401861 Phorodon humuli Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-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
- 241000255972 Pieris <butterfly> Species 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 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
- 241000382353 Pupa Species 0.000 description 1
- 241000157279 Rhagoletis cerasi Species 0.000 description 1
- 241001136903 Rhagoletis pomonella Species 0.000 description 1
- 241001198112 Rhyacionia buoliana 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
- 241000753143 Sitotroga Species 0.000 description 1
- 241000517830 Solenopsis geminata Species 0.000 description 1
- 241000277984 Sparganothis pilleriana Species 0.000 description 1
- 241000256247 Spodoptera exigua Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 241000255626 Tabanus <genus> Species 0.000 description 1
- 241001240492 Tipula oleracea Species 0.000 description 1
- 241001271990 Tomicus piniperda Species 0.000 description 1
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 1
- ANIAQSUBRGXWLS-UHFFFAOYSA-N Trichloronat Chemical compound CCOP(=S)(CC)OC1=CC(Cl)=C(Cl)C=C1Cl ANIAQSUBRGXWLS-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 241001466330 Yponomeuta malinellus Species 0.000 description 1
- 241001136529 Zeugodacus cucurbitae Species 0.000 description 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000003998 acyclic ketones Chemical class 0.000 description 1
- 239000012615 aggregate Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 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
- 150000005215 alkyl ethers 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
- JLYXXMFPNIAWKQ-SHFUYGGZSA-N alpha-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-SHFUYGGZSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000005415 aminobenzoic acids Chemical class 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
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 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
- 238000003556 assay 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
- 150000008047 benzoylureas Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 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
- 239000003054 catalyst Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 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
- 239000007859 condensation product Substances 0.000 description 1
- 150000003997 cyclic ketones Chemical class 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
- 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
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- VJYFKVYYMZPMAB-UHFFFAOYSA-N ethoprophos Chemical compound CCCSP(=O)(OCC)SCCC VJYFKVYYMZPMAB-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- KVGLBTYUCJYMND-UHFFFAOYSA-N fonofos Chemical compound CCOP(=S)(CC)SC1=CC=CC=C1 KVGLBTYUCJYMND-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000417 fungicide 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 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
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000009740 moulding (composite fabrication) Methods 0.000 description 1
- VLULCTRMGOAZNB-UHFFFAOYSA-N n-(3-chloro-2-methylphenyl)-n,n'-dimethylmethanimidamide Chemical compound CN=CN(C)C1=CC=CC(Cl)=C1C VLULCTRMGOAZNB-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 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
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 102000040430 polynucleotide Human genes 0.000 description 1
- 108091033319 polynucleotide Proteins 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000019617 pupation Effects 0.000 description 1
- 229940059835 pyrethrines Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
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
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Opfindelsen angâr hidtil ukendte N-benzoyl-N'-phenyl-urinstoffer, insekticide midler, der indeholder disse forbindelser sont aktive stoffer og en fremgangsmâde til bekærapelse af insekter.
5
Det er kendt, at N-benzoyl-N'-tert.-alkoxycarbonyl-phe-nylurinstoffer har insekticid aktivitet (DE-OS 28 43 851). Den insekticide aktivitet af disse forbindelser er dog ikke altid tilfredsstillende.
10
Det har if0lge opfindelsen vist sig, at N-benzoyl-N'-phenylurinstoffer, der er ejendommelige ved det i den kendetegnende del af krav 1 angivne, har meget h0j insekticid aktivitet. De er overlegne i sammenligning med 15 de fra DE-OS 28 43 851 kendte benzoylurinstoffer i hvil-ke R er en tertiær alkylgruppe, især en tærtiær butyl-gruppe, hvad angâr virkningen deraf.
Den foreliggende opfindelse angâr endvidere et insekti-20 cidt middel, som er ejendommeligt ved det i den kendetegnende del af krav 3 angivne.
Endelig angâr den foreliggende opfindelse en fremgangs-mâde til bekæmpelse af insekter, som er ejendommelig ved 25 det i den kendetegnende del af krav 5 angivne.
Som alkylgrupper til R i formel I kommer sekundære al-kylgrupper med 3 til 12 carbonatomer, sâsom isopropyl, sek.butyl, pentyl-(3), 2,4-dimethyl-pentyl-(3), 2,6-di-30 methyl-heptyl-(4), 2,2,4,4-tetramethyl-pentyl-(3), 1-me-thyl-7-ethyl-nonyl-(4) og 2,8-dimethyl-nonyl-(5) i be-tragtning.
Foretrukne N-benzoyl-N'-phenylurinstoffer er forbindel-35 ser med formel I, hvori X er fluor eller chlor og Y er fluor eller hydrogen og gruppen -COOR befinder sig i p-
DK 157294 B
2 stilling. R er fortrinsvis en sekundær alkylgruppe med 4 til 9 carbonatomer.
Forbindelserne med formel I kan fremstilles ved, at man 5 omsætter et benzoylisocyanat med formlen II
X
10 ^V-CONCO (II)i \ Y .....
hvori
15 X og Y har de f0r angivne betydninger, med en aminoben-zoesyreester med formel III
(m)’
N—'^COOR
hvori Z og R har de f0r angivne betydninger, i nærværelse af 25 et inert, organisk oplpsningsmiddel ved en temperatur mellem 0 og 80 °C.
Især kan forbindelserne med formel I fremstilles ved, at man omsætter et amid med formlen IV 30
X
/7~\ (IV) » // \y_G0NK2 35 \
Y
DK 157294 B
3 hvori X og Y har de f0r angivne betydninger, med et isocyanat med formel 5
'—-'^v.COOR
10 hvori Z og R har de f0r angivne betydninger, eventuelt i nær-værelse af et inert, organisk opl0sningsmiddel, ved en temperatur mellem 0 og 140 °C.
15
Fremgangsmàden til fremstilling af forbindelserne if0lge opfindelsen gennemf0res i nærværelse af velegnede opl0s~ nings- og fortyndingsmidler. Som sâdanne kommer praktisk tait aile indifferente organiske opl0sningsmidler i be-20 tragtning. Hertil h0rer især alifatiske og aromatiske, eventuelt chlorerede eller nitrerede carbonhydrider, sâ-som benzen, toluen, xylener, chlorbenzener, benzin, te-trachlorkulstof, 1,2-dichlorethan, methylenchlorid, chloroform, nitromethan; cycliske og acycliske ethere, 25 sâsom diethylether, dibutylether, tetrahydrofuran, di- oxan; acycliske og cycliske ketoner, sâsom acetone, me-thylethylketon, methylisopropylketon, cyclohexanon; ni-triler, sâsom acetonitril, benzonitril. Ogsâ blandinger af disse opl0sningsmidler kan anvendes.
30
Reaktionstemperaturen kan variere inden for et st0rre omrâde. Den ligger i reglen mellem 0 og 80 °C. Omsæt-ningen forl0ber pâ grund af den.exotherme reaktion sæd-vanligvis ved en temperatur i omrâdet mellem 20 og 60 35 °C.
DK 157294 B
4
Man lader sædvanligvis omsætningen forl0be under normal-tryk. Den kan gennemf0res kontinuerligt eller diskonti-nuerligt.
5 Til gennemf0relse af fremgangsmâden anvender man for- trinsvis reaktionskomponenterne i ækvimolært forhold. Et overskud af den ene eller den anden komponent medf0rer ingen væsentlige fordele. Omsætningen forl0ber praktisk tait kvantitativt.
10 ürinstofferne med formel I fremkommer som faste produk-ter, der i reglen er analyserene, men som eller kan ren-ses ved omkrystallisation. De kan karakteriseres ved elementæranalÿse og smeltepunkt.
15
Hensigtsmæssigt bringer man f0rst den substituerede ami-nobenzoesyreester med formel III sammen med opl0snings-eller fortyndingsmidlet til at foreligge, og derpâ til-sætter man isocyanatet med formel II. Efter flere timers 20 reaktionsvarighed, i reglen 2 timer, bliver produktet derpâ frasuget og t0rret under reduceret tryk.
Metoder til fremstilling af benzoylisocyanaterne med formel II og aminobenzoesyreesterne med formel III er 25 kendt (J. Org. Chem. 28, 1805-1811 (1963); Organicum, 9. oplag 1969, s. 446, 576, VEB Deutscher Verlag der Wis-senschaften).
Reaktionspartnerne omsættes ved den ovenfor angivne sær-30 ligt foretrukne fremgangsmâde i ækvimolære mængder, eventuelt i nærværelse af et indifferent, organisk op-l0sningsmiddel. Reaktionstemperaturen ligger derved mel-lem 0 og 140 °C, fortrinsvis mellem 60 og 100 °C. Eventuelt kan man tilsætte en katalysator, sâsom triethyl-35 amin. Som opl0sningsmiddel kommer de samme opl0snings- midler i betragtning, som kunne anvendes ved omsætningen
DK 157294 B
5 af forbindelserne med formel II med forbindelserne med formel III.
5 Fremstillingseksempel 6,75 g 4-amino-2-chlorbenzoesyre-(2,4-dimethylpentyl-3)-ester opl0ses i 80 ml absolut toluen og blandes drâbevis med 4,6 g 2,6-difluorbenzoylisocyanat. Derpâ lader man 10 reaktionsblandingen henstâ i 2 timer ved 50 °C og frasu-ger ved 0 °C. Derpâ t0rrer man i t0rreskab under reduce-ret tryk ved 40 °C. Man opnâr 8,1 g N-(2,6-difluorbenzo-yl)-N'-[3-chlor-4-(2,4-dimethyl-pentoxy-3-carbonyl)-phe-nyl]-urinstof (forbindelse nr. 1). Smp. 135-140 °C.
15 F0lgende forbindelser lader sig f.eks. fremstille i hen-hold til en af de ovenfor angivne metoder:
X Z
20 / _/
L Λ—CONHCONH-/ X-COOR
\
/ Y
25 nr. X Y z_R_Smp. [°C] 2 Cl H Cl 2,4-dimethyl-pentyl-(3) 152-154 3F F Cl 2,6-dimethyl-heptyl-(4) 140-142 4 Cl Cl Cl " 145-147 5 Cl H Cl " 144-146 30 6 CH3 H Cl " 104-106 7F F Cl pentyl-(3) 150-152 8 Cl Cl Cl " 160-165 9 Cl H Cl " 149-150 10 F F Cl l-methyl-7-ethyl-nonyl-(4) 97- 99 35 11 Cl Cl Cl " olie (n25D=l,5541) 12 Cl H Cl " 90- 95
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6 13 CH3 H Cl " 50- 53 14 F F Br 2,4-dimethyl-pentyl-(3) 140-150 15 F F H 2,6-dimethyl-heptyl-(4) 154-156 5 nr. X Y Z_R_Smp. [°C] 16 Cl Cl H 2,6-dimethyl-heptyl-(4) 167-169 17 Cl H H 2,6-dimethyl-heptyl-(4) 18 F F H 2,4-dimethyl-pentyl-(3) 155-159 19 F Cl H " 10 20 Cl Cl H " 172-177 21 Cl H H " 163-165 22 F F Cl sek.-butyl 168-172 23 Cl Cl Cl " 165-169 24 Cl H Cl " 155-157 15
X
ά Λ-CONHCONH—U Λ-Ζ 20 \ \
Y COOR
25 nr. X_Y_Z_R_Smp, [ QC] 25 F F Cl 2,4-dimethyl-pentyl-(3) 172-174 26 Cl Cl Cl " 155-158 27 Cl H Cl " 195-198 30 28 F F Cl 2,6-dimethy1-n-hepty1-(4) 180-182 29 Cl Cl Cl " 178-181 30 Cl H Cl " 146-150 31 F F Cl 2,8-dimethyl-nonyl-{5) 130-134 32 Cl Cl Cl " 100-104 35 33 Cl H Cl " 110-112
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7 N-benzoyl-N'-phenylurinstofferne if0lge opfindelsen med formel I er velegnet til at bekæmpe skadedyr fra klassen omfattende insekter. De kan anvendes til plantebeskyt-telse samt som bekæmpelsesmiddel til skadelige organis-5 mer pâ hygiejne-, forrâdsbeskyttelses- og veterinærsek-toren.
Til disse skadelige insekter h0rer fra ordenen omfattende sommerfuglene (Lepidoptera) Plutella maculipennis, 10 Leucoptera coffeella, Hyponomeuta malinellus, Argyres- thia conjugella, Sitotroga ceraelella, Phthorimaea oper-culella, Capua reticulana, Sparganothis pilleriana, Ca-coecia murinana, Tortrix viridana, Clysia ambiguella,
Evetria buoliana, Polychrosis botrana, Cydia pomonella, 15 Laspeyresia molesta, Laspeyresia funebrana, Ostrinia nu-bilalis, Loxostege sticticalis, Ephestia kuehniella,
Chilo suppressalis, Galleria Mellonella, Malacosoma neu-stria, Dendrolimus pini, Thaumatopoea pitycampa, Phalera bucephala, Cheimatobia brumata, Hibernia defoliaria, Bu-20 palus piniarus, Hyphantria cunea, Agrotis segetum, Agro-tus ypsilôn, Barathra brassicae, Cirphis unipuncta, Pro-denia litura, Laphygma exigua, Panolis flammea, Earies insulana, Plusia gamma, Alabama argillacea, Lymantria dispar, Lymantria monacha, Pieris brassicea, Aporia cra-25 taegi; fra ordenen omfattende biller (Coleoptera) f.eks. Blito-phaga undata, Melanotus communis, Limonius californicus,
Agriotes lineatus, Agricotes obscurus, Agrilus sinuatus, 30 Meligethes aeneus, Atomaria linearis, Epilachna vari- cestris, Phyllopertha horticola, Popillia japonica, Me-lolontha melolontha, Melolontha hippocastani, Amphimal-lus solstitialis,- Crioceris asparagi, Lema melanopus,
Leptinotarsa decemlineata, Phaedon cochlearia, Phyllo-35 treta nemorum, Chaetocnema tibialis, Phylloides chryso- cephala, Diabrotica 12-punctata, Cassida nebulosa, Bru-
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8 chus lentis, Bruchus rufimanus, Bruchus pisorum, Sitona lineatus, Otiorrhychus sulcatus, Otiorrhynchus ovatus,
Hylobies abietis, Byctiscus betulae, Anthonomus pomorum,
Anthonomus grandis, Ceuthorrhynchus assimilis, Ceuthorr-5 hynchus napi, Sitophilus granaria, Anisandrus dispar,
Ips typographus, Blastophagus piniperda; fra ordenen omfattende tovingede (Diptera) f.eks. Lyco-ria pectoralis, Mayetiola destructor, Dasineura brassi-10 cae, 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 brassicae, Pegomya 15 hyoscyami, Anopheles maculipennis, Culex pipiens, Aedes aegypti, Aedes vexans, Tabanus bovinus, Tipula paludosa,
Musca domestica, Fannia canicularis, Huscina stabulans,
Glossina morsitans, Oestrus ocis, Chrysomya macellaria,
Chrysomya hominivorax, Lucilia cuprina, Lucilia 20 sericata, Hypoderma lineata; fra ordenen omfattende ârevingede (Hymenoptera) f.eks.
Athalia rosae, Hoplocampa minuta, Monomorium pharaonis,
Solenopsis geminata, atta sexdens; 25 fra ordenen omfattende væggelus (Heteroptera) f.eks. Ne-zara viridula, Eurygaster integriceps, Blissus leucopte-rus, Dysdercus cingulatus, Dysderus intermedius, Piesma quadrata, Lygus pratensis; 30 fra ordenen omfattende plantesugere (Homoptera) f.eks.
Perkinsiella saccharicida, Nilaparvata lugens, Empoasca fabae, Psylla mali, Psylla piri, Trialeurodes vaporario-rum, Aphis fabae, Aphis pomi, Aphis sambuci, Aphidula 35 nastrutii, Cerosipha gossypii, Sappaphis mali, Sappaphis mala, Dysphis radicola, Brachycaudus cardui, Brevicoryne
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9 brassicae, Phorodon humuli, Rhopalomyzus ascalonicus,
Myzodes persicae, Myzus cerasi, Dysaulacorthum pseudoso-lani, Acyrthoriphon onobrychis, Macrosiphon rasae, Me-goura viciae, Schizoneura lanuginosa, Pemphigus bursa-5 rius, Dreyfusia nordmannianae, Dreyfusia piceae, Adelges laricis, Viteus vitifolii; fra ordenen omfattende termitterne (Isoptera) f.eks. Re-ticulitermes lucifugus, Calotermes flavicollis/ Leuco-10 termes flavipes. Termes natalensis; og fra ordenen omfattende retvingede (Orthoptera) f.eks.
Forficula auricularia, Acheta domestica, Gryllotalpa gryllotalpa/ Tachycines asynamorus, Locusta migratoria, 15 Stauronotus maroccanus, Schistocera peregrina, Nomada- cris septemfasciata, Melanoplus spretus, Melano plus fe-mur-rubrum, Blatta orientalis, Blattella germanica,
Periplaneta americana, Blabera gigantea.
20 De aktive stoffer kan anvendes som sâdanne, i form af deres formuleringer eller af de pâ basis af disse frem-stillede dispergeringsformer, f.eks. i form af direkte udspr0jtelige opl0sninger, pulvere, suspensioner eller dispersioner, emulsioner, oliedispersioner, pastaer, 25 pudringsmidler/ udstr0mningsmidler, granulater ved ud- spr0jtni'ng, tâgedannelse, forst0vning, udstr0ning eller udhældning. Anvendelsesformerne retter sig helt efter anvendelsesformâlene; de skal i hvert tilfælde sikre den finest mulige fordeling af de aktive stoffer if0lge op-30 findelsen.
Til fremstilling af direkte udspr0jtelige opl0sninger, emulsioner, pastaer eller oliedispersioner kommer mi-neraloliefraktioner med middelh0jt til h0jt kogepunkt, 35 sâsom petroleum eller dieselolie, desuden kultjæreolier samt olier af vegetabilsk eller animalsk oprindelse,
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10 alifatiske, cycliske og aromatiske carbonhydrider, f.eks. benzen, toluen, xylen, paraffin, tetrahydronaph-thalen, alkylerede naphthalener eller disses derivater, f.eks. methanol, éthanol, propanol, butanol, chloroform, 5 tetrachlorkulstof, cyclohexanol, cyclohexanon, chlorben-zen, isophoron, stærkt polære opl0sningsmidler, f.eks. dimethylformamid, dimethylsulfoxid, N-methylpyrrolidon og vand, i betragtning.
10 Vandige anvendelsesformer kan fremstilles af emulsions-koncentrater, pastaer eller befugtelige pulvere (spr0j-tepulvere, oliedispersioner) ved tilsætning af vand. Til fremstilling af emulsioner, pastaer eller oliedispersioner kan stofferne som sâdanne eller stofferne opl0st i 15 en olie eller et opl0sningsmiddel homogeniseres i vand ved hjælp af befugtnings-, adhæsions-, dispergerings-eller emulgeringsmidler. Man man kan ogsâ fremstille koncentrater, der bestâr af aktivt stof, befugtnings-, adhæsions-, dispergerings-- eller emulgeringsmiddel og 20 eventuelt opl0sningsmiddel eller olie, hvilke koncentrater er velegnet til fortynding med vand.
Som overfladeaktive· stoffer kommer alkalimetal-, jord-alkalimetal- eller ammoniumsalte af ligninsulfonsyre, 25 naphthalensulfonsyre, phenolsulfonsyre, alkylarylsulfo- nater, alkylsulfater, alkylsulfonater, alkalimetal- og jordalkali'metaïsalte af dibutylnaphthalensulfonsyre, laurylethersulfat, fedtalkoholsulfater, fedtsure alkalimetal- og jordalkalimetalsalte, salte af sulfaterede he-30 xadecanoler, heptadecanoler, octadecanoler, salte af sulfaterede fedtalkoholglycolethere, kondensationspro-dukter af sulfoneret naphthalen og naphthalenderivater med formaldehyd, kondensationsprodukter af naphthalen eller naphthalensulfonsyrer med phénol og formaldehyd, 35 polyoxyethylenoctylphenolether, ethoxyleret isooctylphe- nol, octylphenol, nonylphenon, alkylphenolpolyglycol-
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11 ether, tributylphenylpolyglycolether, alkylarylpoly-etheralkoholer, isotridecylalkohol, fedtalkoholethylen-oxid-kondensater, ethoxyleret ricinusolie, polyoxyethy-lenalkylether, ethoxyleret polyoxypropylen, laurylalko-5 holpolyglycoletheracetal, sorbitester, lignin, sulfitaf- faldslud og methylcellulose i betragtning.
Pulver-, udstr0nings- og pudringsmidler kan fremstilles ved blanding eller fælles formaling af de aktive stoffer 10 med et fast bærestof.
Granulater, f.eks. omhyllings-, imprægnerings- og homo-gengranulater, kan fremstilles ved binding af de aktive stoffer til faste bærestoffer. Faste bærestoffer er 15 f.eks. mineraijorder, sâsom silicagel, kiselsyrer, ki-selgeler, silicater, talkum, kaolin, attaler, kalksten, kalk, kridt, bolus, l0ss, 1er, dolomit, diatomejord, calcium- og magnesiumsulfat, magnesiumoxid, formalede formstoffer, g0dningsmidler, sâsom f.eks. ammoniumsul-20 fat, ammoniumphosphat, ammoniumnitrat, urinstoffer og vegetabilske produkter, sâsom kornmel, træbark-, træ- og n0ddeskallemel, cellulosepulver og andre faste bærestof-fer.
25 Formuleringerne indeholder i almindelighed mellem 0,1 og 95 vægt-% aktivt stof, fortrinsvis mellem 0,5 og 90 vægt-%.
Koncentrationerne af det aktive stof i de anvendelses-30 klare præparater kan varieres indenfor st0rre omrâder. I almindelighed ligger de mellem 0,0001 og 10%, fortrinsvis mellem 0,Q1 og 1%.
Eksempler pâ formuleringer er: I. 5 vægtdele af forbindelse nr. 6 blandes grundigt 35
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12 med 95 vægtdele findelt kaolin. Man opnâr pâ denne mâde et pudringsmiddel, der indeholder 5 vægt-% af det aktive stof.
5 II. 30 vægtdele af forbindelse nr. 7 blandes grundigt med en blanding af 92 vægtdele pulverformig kiselsyregel og 8 vægtdele paraffinolie, der var spr0jtet pâ overfladen af denne kiselsyregel. Man opnâr pâ denne mâde et præparat af det aktive stof med god adhæsion.
10 III. 80 vægtdele af forbindelse nr. 25 blandes godt med 3 vægtdele af natriumsaltet af diisobutylnaphthalen-a-sulfonsyre, 10 vægtdele af natriumsaltet af en lignin-sulfonsyre fra en sulfit-affaldslud og 7 vægtdele pul-15 verformig kiselsyregel og formales i en hammerm0lle.
De aktive stoffer kan ogsâ med godt résultat anvendes ved ultra-lav-volumen-metoden (ULV), hvorved det er mu-ligt at udbringe formuleringer med over 95 vægt-% aktivt 20 stof eller endog det aktive stof uden additiver.
Den anvendte mængde af aktivt stof andrager under fri-landsbetingelser mellem 0,2 og 10 kg/ha, fortrinsvis mellem 0,5 og 2,0 kg/ha.
25
Til de aktive stoffer kan man tilsætte olier af forskel-lige typer, herbicider, fungicider, andre bekæmpelses-midler mod skadevoldende organismer, baktericider, even-tuelt ogsâ f0rst umiddelbart f0r anvendelsen (tankmix).
30 Disse midler kan tilblandes til midlerne if0lge opfind-elsen i vægtforhold mellem 1:10 og 10:1.
Eksempelvis kan man tilblande f0lgende midler: 35 l,2-dibrom-3-chlorpropan, 1,3-dichlorpropen, 1,3-di-chlorpropen + 1,2-dichlorpropan, 1,2-dibrom-ethan, 2-
DK 157294 B
13 sek.-buty1-phenyl-N-methylcarbaraat, o-chlorphenyl-N-me-thylcarbamat, 3-isopropyl-5-methylphenyl-N-methylcarba-mat o-isopropoxyphenyl-N-methylcarbamat, 3,5-dimethyl-4-methylmercapto-phenyl-N-methylcarbamat, 4-dimethylamino-5 3,5-xylyl-N-methylcarbamat, 2-(l,3-dioxolan-2-yl)-phe-nyl-N-methylcarbamat, 1-naphthyl-N-methylcarbamat, 2,3-dihydro-2,2-dimethyl-benzofuran-7-yl-lSI-methylcarbamat, 2,2-dimethyl-l,3-benzodioxol-4-yl-N-methylcarbamat, 2-dimethylamino-5,6-dimethyl-4-pyrimidinyl-dimethylcarba-10 mat, 2-methyl-2-(methylthio)-propionaldehyd-0-(methyl- carbamoyl)-oxim, S-methyl-N-[(methylcarbamoyl)-oxy]-thio-acetimidat, methyl-N',N'-dimethyl-N-[(methylcarba-moyl)oxy]-1-thiooxamidat, N-(2-methyl-chlor-phenyl)-N',N1-dimethylformamidin, tetrachlorthiophen, 1-(2,6-15 difluor-benzoyl)-3-(4-chlor-phenyl)-urinstof, 0,0-dime- thy1-0-(p-nitropheny1)-phosphorthioat, O,O-diethy1-0-(p-nitrophenyl)-phosphorthioat, O-ethyl-O-(p-nitrophenyl)-phenyl-phosphorthioat, 0-0-dimethyl-0-(3-methyl-4-nitro-phenyl)-phosphorthioat, 0,0-diethy1-0-(2,4-dichlorphe-20 nyl)-phosphorthioat, O-ethyl-O-(2,4-dichlorphenyl)- phenyl-phosphonothioat, 0,O-dimethyl-O-(2,4,5-trichlor-phenyl)-phosphorthioat, O-ethyl-O-(2,4,5-trichlorphe-nyl)-ethyl-phosphonothioat, O,O-dimethyl-O-(4-brom-2,5-dichlorpheny1)-phosphorthioat, 0,O-dimethyl-O-(2,5-di-25 chlor-4-iodphenyl)-phosphorthioat, 0,0-dimethy1-0-(3- methyl-4-methylthiophenyl)-phosphorthioat, O-ethyl-O-(3-methyl-4-methylthiophenyl)-isopropyl-phosphoramidat, 0,0-diethyl-0-[p-methylsulfinyl-phenyl]-phosphorthioat, O-ethyl-S-phenyl-ethyl-phosphonodithioat, 0,0-diethyl-30 [2-chlor-l-(2,4-dichlorphenyl)-vinyl]-phosphat, 0,0-di- methyl-[-2-chlor-l-(2,4,5-trichlorphenyl)]-vinyl-phos-phat, 0,0-dimethyl-S-(1'-phenyl)-ethylacetat-phosphor-dithioat, bis-(dimethylamino)-£luorphosphinoxid, octa-methyl-pyrophosphoramid, 0,0,0,0-tetraethyldithio-py-35 rophosphat, S-chlormethyl-0,0-diethyl-phosphordithioat, O-ethyl-S,S-dipropyl-phosphordithioat, 0,0-dimethy1-0-
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14 2,2-dichlorvinyl-phosphat, 0,O-dimethyl-1,2-dibrom-2,2-dichlorethylphosphat, 0,0-dimethyl-2,2,2-trichlor-l-hy-droxy-ethylphosphonat, 0,O-dimethyl-S-[1,2-biscarbetho-xy-ethyl-(l)]-phosphordithioat, 0,0-dimethyl-0-(l-me-5 thyl-2-carbmethoxy-vinyl)-phosphat, 0,0-dimethyl-S-(N-methyl-carbamoyl-methyl)-phosphordithioat, 0,0-dimethyl- S-(N-methyl-carbamoyl-methyl)-phosphorthioat, 0,0-dime-thyl-S-(N-methoxyethyl-carbamoy1-methy1)-phosphordi-thioat, 0,0-dimethyl-S-{N-formyl-N-methyl-carbamoylme-10 thyl-phosphordithioat/ 0/0-dimethyl-0-[l-methyl-2-(rae- thyl-carbamoyl)-vinyl]-phosphat, 0,0-dimethyl-0-[(1-me-thyl-2-dimethylcarbamoyl)"-vinyl ]-phosphat, 0,0-dimethyl- 0-[(l-methyl-2-chlor-2-diethylcarbamoyl)-vinyl]-phosphat , 0,0-diethy1-S-(ethylthio-methyl)-phosphordithioat, 15 0,0-diethyl-S-[(p-chlorphenylthio)-methyl]-phosphordi- thioat, 0/O-dimethyl-S-(2-ethylthioethyl)-phosphor-thioat, 0,O-dimethyl-S-(2-ethylthioethyl)-phosphordi-thioat/ 0/0-dimethyl-S-(2-ethylsulfinyl-ethyl)-phosphor-thioat, 0,0-diethyl-S-(2-ethylthio-ethyl)-phosphordi-20 thioat, 0/0-diethyl-S-(2-ethylsulfinyl-ethyl)-phosphor- thioat, O/O-diethyl-thiophosphoryliminophenyl-acetoni-tril/ 0/0-diethy1-S-(2-chlor-l-phthalimidoethyl)-phos-phordithioat, Ο,Ο-diethyl-S-[6-chlor-benzoxazolon-(2)-yl(3)]-methyldithiophosphat, 0,O-dimethyl-S-[2-methoxy-25 1/3/4-thiadiazol-5-[4H]-onyl-(4)-methyl]-phosphordi- thioat, 0,0-diethyl-0-[3,5/6-trichlor-pyridyl-(2)]-phosphorthioat, 0,0-diethy1-0-(2-pyrazinyl)-phosphor-thioat, 0/0-diethyl-0-[2-isopropyl-4-methy1-pyrimidi-nyl(6)]-phosphorthioat, O/O-diethyl-O-[2-(diethylamino)-30 6-methyl-4-pyrimidinyl]-thionophosphat, 0,0-dimethyl-S- (4-oxo-l/2,3-benzotriazin-3-[4H]-y1-methy1)-phosphordi-thioat/ O/O-dimethyl-S-£{4,6-diamino-l,3,5-triazin-2-yl)-methyl]-phosphordithioat, O,O-diethyl-(1-phenyl- 1,2,4-triazol-3-yl)-thionophosphat, O,S-dimethyl-phos-35 phor-amido-thioat, 0,S-dimethyl-N-acetyl-phosphoramido- thioat, α-hexachlor-cyclohexan, l,l-di-(p-methoxyphe-
, DK 157294 B
15 nyl)-2,2,2-trichlorethan, 6/7/8,9,10,10-hexachlor-1,5,53,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxa-thiepin-3-oxid, pyrethriner, DL-2-allyl-3-methyl-cyclo-penten-(2)-on-(1)-yl-(4)-DL-cis,-trans-chrysanthemat, 5~ 5 benzyl-furyl-(3)-methyl-DL-cis,-trans-chrysanthemat, 3- phenoxybenzyl(±)-cis,trans-2,2-dimethyl-3-(2,2-dichlor-vinyl)-cyclopropancarboxylat, a-cyano-3-phenoxybenzyl-(±)-cis,trans-2,2-dimethyl-3-(2,2-dicblorvinyl)-cyclopropancarboxylat , (s)-a-cyano-3-phenoxybenzyl-cis-10 (IR,3R)-2,2-dimethyl-3-(2,2-dibromvinyl)-cyclopropancar boxylat , 3,4,5,6-tetrahydrophthalimidoethyl-DL-cis,-trans-chrysanthemat, 2-methyl-5-(2-propinyl)-3-furylme-thyl-chrysanthemat, (a-cyano-3-phenoxybenzyl)-a-isopro-pyl-4-chlorphenylacetat.
15
De f0lgende eksempler dokumenterer de nye forbindelsers biologiske virkning. De kendte aktive stoffer N-(2,6-difluorbenzoyl)-N1-(3-chlor-4-tert.-butoxy-phenyl)-urin-stof, N-(2-chlorbenzoyl)-N'-(3-chlor-4-tert.-butoxycar-20 bonyl-phenyl)-urinstof og N-(2-methylbenzoyl)-N'-(3- chlor-4-tert.-butoxycarbonyl-phenyl)-urinstof (DE-OS 28 43 852) er sammenligningsstoffer.
Nummereringen af de aktive stoffer svarer til numraere-25 ringen i den tabellariske opstilling.
Eksempel A
Opdrætningsfors0g med moskitolarver (Aedes aegypti).
30 I 200 ml ledningsvand, hvortil der blev tilsat et præpa-rat af aktivt stof af 10 vægt-% aktivt stof og 90 vægt-% af en eraulgatorblanding af 10% ethoxyleret ricinusolie, 20% ethoxyleret isooctylphenyl og 70% cyclohexanon, ind-35 f0rer man 30 til 40 Aedes-larver i 4' stadiura.
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16
Fors0gstemperaturen andrager 25 °C. Man bed0mmer forpup-ningen og de voksne dyrs frig0relse fra hylsteret, hvor-ved en ubehandlet blindpr0ve tjener soin mâlestok. ünder den 12 timer lange fors0gsperiode fodrer man en gang med 5 et sædvanligt, pulveriseret fiskefoder.
I dette fors0g viste de aktive stoffer 1, 2, 5 og 8 en bedre virkning end sammenligningsmidlerne.
10 Eksempel B
Opdrætsfors0g med bomuldsvæggelus (Dysdercus intermedi-us) 15 50 g bomuldssâsæd kvældes i 24 timer i det vandige præ- parat af 10 vægt-% aktivt stof og 90 vægt-% af en emul-gatorblanding af 10% ethoxyleret ricinusolie, 20% ethoxyleret isooctylphenyl og 70% cyclohexanon. Den ovenstâende væske bliver hældt væk.
20
Derpâ indfprer man 20 væggelus i det næstsidste larve-stadium i 1 liter glas, hvis bund er dækket med fugtigt sand. Disse dyr fâr i 7 dage de forbehandlede fr0 som den eneste næring. Derpâ tilbydes der ubehandlet foder.
25
Man iagttager, om dyrene a) overlever og b) skifter ham, sa de udvikler sig til voksne dyr.
30
Ved dette fors0g viser de aktive stoffer 1, 2, 3, 4, 5, 6, 7 og 8 en bedre virkning end sammenligningsmidlet.
Sammenligningsforspg
I de f0lgende eksempler valgte man de fra DE-OS
35
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17 28 43 851 kendte forbindelser A-C som sammenlignings-stoffer.
F ° 0 5 0J-„h-c~nh-Q^coo-c(ch3)3 Nr' ë-^za « 851 F Cl 0 0 Q-ü-NHi-«H-QM;00-C(CH3)3 Nr. 2|^28 „ 851
^C1 CI
10 0 0 ^3-C“NH-C-NH-(^-COO-C(CH3)3 Nr. 16_^a 2g 43 g51 <:h3 cl 15
De i de f0lgende eksempler 34 og 35 angivne forbindelser falder ind under hovedkravet i ans0gnimgen og er kende-tegnet ved f0lgende struktur 20
X Z
<ζ^>—lC0NHC0NH—^^>-C00R Y
25
Nr._X_Y_Z_R__ 34 F F Cl 2-methyl-6-ethyl-nonyl-(4) 35 Cl H Cl 30
De koncentrationer, ved hvilke de unders0gte forbindelser frembringer den i hvert tilfælde angivne mortalitet eller hæmning, er de pâgældende minimalkoncentrationer.
35 For hver koncentration gennemf0rte man mindst to fors0g.
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18
Eksempel l
Opdrætsfors0g med moskitolarver (Aedes aegypti) 5 Præparatet indeholdende det aktive stof blandes med 200 ml ledningsvand, og derpâ tilf0res der 30-40 Aedes-lar-ver i det 4' stadium. Fors0gstemperaturen andrager 25 °C. Man bed0mmer forpupningen og de voksne dyrs frig0-relse fra hylsteret, hvorved en ubehandlet blindpr0ve 10 tjener som mâlestok. ünder fors0get fodres der een gang med TETRAMIN. Resultaterne er sammenfattet i den f0lgen-de tabel:
Tabel 1 15
Eks. nr. koncentration af hæmning _ aktivt stof [ppm] [%] 1 0,04 100 26 0,4 100 20 14 0,04 100 7 0,1 100 8 0,5 100 3 0,04 100 4 0,25 100 25 34 0,2 100
Sammenligningseksempel
Al 0 30 B 1 0
Cl 0
Eks. II
Dyrknîngsfors0g med bomuldstæger (Dysdercus intermedius) 50 g bomuldsfr0 kvældes i 24 timer i det vandige præpa- 35 19
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rat af aktivt stof. Den ovenstâende væske afrystes.
Derpâ tilf0rer man 20 tæger i det næstsidste larvestadi-um i 1 liter glas, hvis bund er dækket med fugtigt sand.
5 Disse dyr fâr i 7 dage de forbehandlede fr0 soin den ene-ste næring. Derpâ tilbydes der ubehandiet foder.
Man bed0mmer mortaliteten. Resultatet er sammenfattet i tabel 2.
10
Tabel 2
Eks. nr. koncentration af mortalitet _ aktivt stof [ppm] [%]_ 15 1 0,2 100 26 2 100 14 10 100 9 10 100 7 0,05 100 20 5 25 100 6 25 100 3 5 100 4 25 100 25 25 100 25 35 10 100 34 2 100
Sammenligningseksempel 30 B 25 0 C 25 0 35
Claims (3)
1. N-benzoyl-N'-phenylurinstoffer, kendetegnet ved, at de har formlen I 5 X /^X-CONHCONH-^ N—^COOH U)» 10. hvori X er chlor, fluor eller methyl, Y er chlor, fluor eller hydrogen, 15. er brom, chlor, fluor eller hydrogen, og R er en sekundær alkylgruppe med 3 til 12 carbonatomer.
2. N-benzoyl-N'-phenylurinstoffer if0lge krav 1, kendetegnet ved, at de har formlen la X CONHCONH-^Jy-- COOR ( } ^ 25 ^ hvori X er chlor eller fluor, Y er fluor eller hydrogen, Z er brom, chlor, fluor eller hydrogen, og 30 R er en sekundær alkylgruppe med 4 til 9 carbonatomer.
3. Insekticidt middel, kendetegnet ved, at det indeholder indifferente additiver og en forbindelse if0lge krav 1. 35
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3100911 | 1981-01-14 | ||
| DE19813100911 DE3100911A1 (de) | 1981-01-14 | 1981-01-14 | N-benzoyl-n'-phenylharnstoffe und ihre verwendung zur bekaempfung von insekten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK10782A DK10782A (da) | 1982-07-15 |
| DK157294B true DK157294B (da) | 1989-12-04 |
| DK157294C DK157294C (da) | 1990-08-27 |
Family
ID=6122592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK010782A DK157294C (da) | 1981-01-14 | 1982-01-13 | N-benzoyl-n'-phenylurinstoffer, insekticidt middel og fremgangsmaade til bekaempelse af insekter |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US4599356A (da) |
| EP (1) | EP0056124B1 (da) |
| JP (1) | JPS57140756A (da) |
| AT (1) | ATE8134T1 (da) |
| DE (2) | DE3100911A1 (da) |
| DK (1) | DK157294C (da) |
| GR (1) | GR75124B (da) |
| IE (1) | IE52512B1 (da) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5342958A (en) * | 1970-05-15 | 1994-08-30 | Solvay Duphar International Research B.V. | Organic compounds derived from urea or thiourea |
| US5245071A (en) * | 1970-05-15 | 1993-09-14 | Duphar International Research B.V. | Organic compounds derived from urea or thiourea |
| NL160809C (nl) * | 1970-05-15 | 1979-12-17 | Duphar Int Res | Werkwijze ter bereiding van benzoylureumverbindingen, alsmede werkwijze ter bereiding van insekticide prepara- ten op basis van benzoylureumverbindingen. |
| DE3100911A1 (de) * | 1981-01-14 | 1982-08-05 | Basf Ag, 6700 Ludwigshafen | N-benzoyl-n'-phenylharnstoffe und ihre verwendung zur bekaempfung von insekten |
| US4783485A (en) * | 1983-01-24 | 1988-11-08 | Duphar International Research B.V. | Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same |
| 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 |
| AU601145B2 (en) * | 1985-03-01 | 1990-09-06 | Duphar International Research B.V. | Benzoyl urea derivatives having anti-tumor activity |
| DK167280B1 (da) * | 1985-03-20 | 1993-10-04 | Ciba Geigy Ag | 3-aryluracilderivater, fremgangsmaade til fremstilling deraf, ukrudtsbekaempelsesmidler indeholdende disse derivater samt anvendelsen af derivaterne til ukrudtsbekaempelse |
| DE3722155A1 (de) * | 1987-07-04 | 1989-01-12 | Basf Ag | (n-benzoyl-n'-halogenalkoxycarbonylphenyl)-harnstoffe |
| HUT48880A (en) * | 1987-07-20 | 1989-07-28 | Sandoz Ag | Insecticides and acaricides comprising new n-benzoyl-n'-thienyl urea derivative as active ingredient and process for producing the active ingredients |
| US4859699A (en) * | 1987-07-20 | 1989-08-22 | Sandoz Ltd. | Substituted N-benzoyl-N'-thienylureas |
| DE10023430A1 (de) | 2000-05-12 | 2001-11-15 | Bayer Ag | Substituierte N-Benzoyl-N'-(tetrazolylphenyl)-harnstoffe |
| IL164249A0 (en) * | 2002-04-11 | 2005-12-18 | Aventis Pharma Gmbh | Acyl-3-carboxphenylurea derivatives, processes forpreparing them and their use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL160809C (nl) * | 1970-05-15 | 1979-12-17 | Duphar Int Res | Werkwijze ter bereiding van benzoylureumverbindingen, alsmede werkwijze ter bereiding van insekticide prepara- ten op basis van benzoylureumverbindingen. |
| DE2843851A1 (de) * | 1978-10-07 | 1980-04-17 | Bayer Ag | Substituierte n-benzoyl-n'-tert.-alkoxycarbonylphenyl-(thio)-harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| DE3100911A1 (de) * | 1981-01-14 | 1982-08-05 | Basf Ag, 6700 Ludwigshafen | N-benzoyl-n'-phenylharnstoffe und ihre verwendung zur bekaempfung von insekten |
-
1981
- 1981-01-14 DE DE19813100911 patent/DE3100911A1/de not_active Withdrawn
- 1981-12-08 GR GR66735A patent/GR75124B/el unknown
- 1981-12-11 AT AT81110349T patent/ATE8134T1/de not_active IP Right Cessation
- 1981-12-11 EP EP81110349A patent/EP0056124B1/de not_active Expired
- 1981-12-11 DE DE8181110349T patent/DE3164474D1/de not_active Expired
-
1982
- 1982-01-08 IE IE29/82A patent/IE52512B1/en unknown
- 1982-01-13 DK DK010782A patent/DK157294C/da not_active IP Right Cessation
- 1982-01-13 JP JP57002925A patent/JPS57140756A/ja active Pending
-
1983
- 1983-11-28 US US06/555,393 patent/US4599356A/en not_active Expired - Fee Related
-
1986
- 1986-03-27 US US06/844,501 patent/US4699923A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IE52512B1 (en) | 1987-11-25 |
| EP0056124A3 (en) | 1982-12-08 |
| EP0056124A2 (de) | 1982-07-21 |
| DK157294C (da) | 1990-08-27 |
| EP0056124B1 (de) | 1984-06-27 |
| ATE8134T1 (de) | 1984-07-15 |
| DE3164474D1 (en) | 1984-08-02 |
| US4699923A (en) | 1987-10-13 |
| US4599356A (en) | 1986-07-08 |
| GR75124B (da) | 1984-07-13 |
| JPS57140756A (en) | 1982-08-31 |
| DK10782A (da) | 1982-07-15 |
| DE3100911A1 (de) | 1982-08-05 |
| IE820029L (en) | 1982-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |