CH638500A5 - 1-(mono-o-substituierte-benzoyl)-3-(substituierte-pyrazinyl)-harnstoffe sowie diese verbindungen enthaltende insektizide. - Google Patents

1-(mono-o-substituierte-benzoyl)-3-(substituierte-pyrazinyl)-harnstoffe sowie diese verbindungen enthaltende insektizide. Download PDF

Info

Publication number: CH638500A5
Authority: CH; Switzerland
Prior art keywords: halogen; methyl; alkyl; substituted; pyrazinyl
Prior art date: 1977-06-22

Application number

CH677078A

Other languages

German (de)

English (en)

Inventor

John Louis Miesel

Riaz Fazal Abdulla

Norman Henry Terando

Original Assignee

Lilly Co Eli

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-06-22

Filing date

1978-06-21

Publication date

1983-09-30

1977-07-27 Priority claimed from US05/819,639 external-priority patent/US4133956A/en

1978-06-21 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1983-09-30 Publication of CH638500A5 publication Critical patent/CH638500A5/de

Links

150000001875 compounds Chemical class 0.000 title claims description 99
-1 MONO-O-SUBSTITUTED-BENZOYL Chemical class 0.000 title claims description 78
150000003672 ureas Chemical class 0.000 title claims description 15
239000002917 insecticide Substances 0.000 title claims description 8
239000000203 mixture Substances 0.000 claims description 78
229910052736 halogen Inorganic materials 0.000 claims description 57
150000002367 halogens Chemical class 0.000 claims description 56
229910052739 hydrogen Inorganic materials 0.000 claims description 45
239000001257 hydrogen Substances 0.000 claims description 43
238000000034 method Methods 0.000 claims description 43
150000002431 hydrogen Chemical class 0.000 claims description 35
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 32
239000004480 active ingredient Substances 0.000 claims description 32
235000013877 carbamide Nutrition 0.000 claims description 32
239000002904 solvent Substances 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 31
238000002360 preparation method Methods 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
241000238631 Hexapoda Species 0.000 claims description 24
239000000460 chlorine Substances 0.000 claims description 20
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
229910052801 chlorine Inorganic materials 0.000 claims description 19
239000004202 carbamide Substances 0.000 claims description 18
241000196324 Embryophyta Species 0.000 claims description 16
125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims description 15
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
229910052794 bromium Inorganic materials 0.000 claims description 15
230000008569 process Effects 0.000 claims description 15
241000254173 Coleoptera Species 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 12
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 11
230000000749 insecticidal effect Effects 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000001624 naphthyl group Chemical group 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
241000255925 Diptera Species 0.000 claims description 5
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
125000004098 2,6-dichlorobenzoyl group Chemical group O=C([*])C1=C(Cl)C([H])=C([H])C([H])=C1Cl 0.000 claims description 4
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
239000003995 emulsifying agent Substances 0.000 claims description 3
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 claims description 2
240000004658 Medicago sativa Species 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
239000002270 dispersing agent Substances 0.000 claims description 2
239000000428 dust Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
239000004563 wettable powder Substances 0.000 claims description 2
239000000080 wetting agent Substances 0.000 claims description 2
235000010624 Medicago sativa Nutrition 0.000 claims 1
241000257226 Muscidae Species 0.000 claims 1
241000607479 Yersinia pestis Species 0.000 claims 1
150000008047 benzoylureas Chemical class 0.000 claims 1
239000004305 biphenyl Substances 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
239000013057 ectoparasiticide Substances 0.000 claims 1
238000003898 horticulture Methods 0.000 claims 1
230000001988 toxicity Effects 0.000 claims 1
231100000419 toxicity Toxicity 0.000 claims 1
230000036642 wellbeing Effects 0.000 claims 1
239000000243 solution Substances 0.000 description 60
239000007787 solid Substances 0.000 description 48
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
238000002844 melting Methods 0.000 description 36
230000008018 melting Effects 0.000 description 36
239000011541 reaction mixture Substances 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
ZTUIVBFRTPPWEZ-UHFFFAOYSA-N 2-chlorobenzoyl isocyanate Chemical compound ClC1=CC=CC=C1C(=O)N=C=O ZTUIVBFRTPPWEZ-UHFFFAOYSA-N 0.000 description 27
239000000047 product Substances 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 20
239000000543 intermediate Substances 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
239000000155 melt Substances 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
229920000742 Cotton Polymers 0.000 description 16
241000219146 Gossypium Species 0.000 description 16
238000002329 infrared spectrum Methods 0.000 description 15
239000003921 oil Substances 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
238000000921 elemental analysis Methods 0.000 description 12
239000000463 material Substances 0.000 description 11
238000010992 reflux Methods 0.000 description 11
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 10
235000021186 dishes Nutrition 0.000 description 10
238000009472 formulation Methods 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000004458 analytical method Methods 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
150000002923 oximes Chemical class 0.000 description 9
SJYCYRJOUJAQFB-UHFFFAOYSA-N 5-(4-bromophenyl)-6-methylpyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1=CC=C(Br)C=C1 SJYCYRJOUJAQFB-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
238000002474 experimental method Methods 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
241000255749 Coccinellidae Species 0.000 description 7
244000068988 Glycine max Species 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
235000013601 eggs Nutrition 0.000 description 6
239000007858 starting material Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000012085 test solution Substances 0.000 description 6
NHUFIOMPICRXFX-UHFFFAOYSA-N 5,6-dichloropyrazin-2-amine Chemical compound NC1=CN=C(Cl)C(Cl)=N1 NHUFIOMPICRXFX-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
239000000284 extract Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
JHSPCUHPSIUQRB-UHFFFAOYSA-N 2,6-dichlorobenzamide Chemical compound NC(=O)C1=C(Cl)C=CC=C1Cl JHSPCUHPSIUQRB-UHFFFAOYSA-N 0.000 description 4
RZMVHCYCUAKRMM-UHFFFAOYSA-N 2-methylbenzoyl isocyanate Chemical compound CC1=CC=CC=C1C(=O)N=C=O RZMVHCYCUAKRMM-UHFFFAOYSA-N 0.000 description 4
HWCKAMAVEWVBDO-UHFFFAOYSA-N 5-chloropyrazin-2-amine Chemical compound NC1=CN=C(Cl)C=N1 HWCKAMAVEWVBDO-UHFFFAOYSA-N 0.000 description 4
FMBKXKZEXQCCFM-UHFFFAOYSA-N 6-(trifluoromethyl)pyrazin-2-amine Chemical compound NC1=CN=CC(C(F)(F)F)=N1 FMBKXKZEXQCCFM-UHFFFAOYSA-N 0.000 description 4
241000256118 Aedes aegypti Species 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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240000000047 Gossypium barbadense Species 0.000 description 4
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241000255777 Lepidoptera Species 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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238000003359 percent control normalization Methods 0.000 description 4
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150000003216 pyrazines Chemical class 0.000 description 4
NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 3
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JVSDZAGCHKCSGR-UHFFFAOYSA-N 2,5-dichloropyrazine Chemical compound ClC1=CN=C(Cl)C=N1 JVSDZAGCHKCSGR-UHFFFAOYSA-N 0.000 description 3
OYCDPVNXUKEYBQ-UHFFFAOYSA-N 2-amino-2-hydroxybutanedinitrile;4-methylbenzenesulfonic acid Chemical compound N#CC(O)(N)CC#N.CC1=CC=C(S(O)(=O)=O)C=C1 OYCDPVNXUKEYBQ-UHFFFAOYSA-N 0.000 description 3
JTPXVCKCLBROOJ-UHFFFAOYSA-N 2-amino-6-chloropyrazine Chemical compound NC1=CN=CC(Cl)=N1 JTPXVCKCLBROOJ-UHFFFAOYSA-N 0.000 description 3
WGFILESHIVMXAY-UHFFFAOYSA-N 2-bromobenzoyl isocyanate Chemical compound BrC1=CC=CC=C1C(=O)N=C=O WGFILESHIVMXAY-UHFFFAOYSA-N 0.000 description 3
YLDOZTMPEJEYPW-UHFFFAOYSA-N 5-(4-bromophenyl)-6-chloropyrazin-2-amine Chemical compound ClC1=NC(N)=CN=C1C1=CC=C(Br)C=C1 YLDOZTMPEJEYPW-UHFFFAOYSA-N 0.000 description 3
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150000004665 fatty acids Chemical class 0.000 description 3
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JGAJCAJHSHUPGH-UHFFFAOYSA-N methyl 3-amino-6-chloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=CN=C1N JGAJCAJHSHUPGH-UHFFFAOYSA-N 0.000 description 3
INCSQLZZXBPATR-UHFFFAOYSA-N methyl 3-aminopyrazine-2-carboxylate Chemical compound COC(=O)C1=NC=CN=C1N INCSQLZZXBPATR-UHFFFAOYSA-N 0.000 description 3
150000004987 o-phenylenediamines Chemical class 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/16—Derivatives of isocyanic acid having isocyanate groups acylated
- 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
- 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<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/20—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (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)
Plural Heterocyclic Compounds (AREA)

CH677078A 1977-06-22 1978-06-21 1-(mono-o-substituierte-benzoyl)-3-(substituierte-pyrazinyl)-harnstoffe sowie diese verbindungen enthaltende insektizide. CH638500A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB2609377		1977-06-22
US05/819,639 US4133956A (en)	1977-07-27	1977-07-27	Preparation of benzoylureas

Publications (1)

Publication Number	Publication Date
CH638500A5 true CH638500A5 (de)	1983-09-30

Family

ID=26258071

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH677078A CH638500A5 (de)	1977-06-22	1978-06-21	1-(mono-o-substituierte-benzoyl)-3-(substituierte-pyrazinyl)-harnstoffe sowie diese verbindungen enthaltende insektizide.

Country Status (20)

Country	Link
JP (1)	JPS549288A (tr)
AT (1)	AT367046B (tr)
AU (1)	AU516505B2 (tr)
BG (2)	BG30174A4 (tr)
BR (1)	BR7803939A (tr)
CH (1)	CH638500A5 (tr)
DD (1)	DD141831A5 (tr)
DE (1)	DE2826893A1 (tr)
DK (1)	DK279378A (tr)
FR (1)	FR2398738A1 (tr)
GB (1)	GB2001053B (tr)
GR (1)	GR72967B (tr)
IT (1)	IT1096793B (tr)
NL (1)	NL7806678A (tr)
OA (1)	OA06108A (tr)
PT (1)	PT68189A (tr)
RO (1)	RO78069A (tr)
SE (1)	SE7807127L (tr)
TR (1)	TR20446A (tr)
YU (1)	YU144078A (tr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4281003A (en) *	1978-08-31	1981-07-28	Eli Lilly And Company	1-(2-6-Dihalobenzoyl)-3-(5-substituted-2-pyridinyl)urea insecticides and insecticidal method
JPS60117551A (ja) *	1983-11-28	1985-06-25	Shin Kobe Electric Mach Co Ltd	鉛蓄電池用陽極板の製造法
JPH0768205B2 (ja) *	1986-05-13	1995-07-26	住友化学工業株式会社	ベンゾイル尿素誘導体およびそれを有効成分とする殺虫剤
DE60114153T2 (de) *	2000-02-16	2006-07-06	Neurogen Corp., Branford	Substituierte arylpyrazine
EP2878198B1 (de)	2013-11-29	2016-09-14	Flügel GmbH	Verfahren zum Anlocken von kambiophagen, xylophagen und/oder myzetophagen Insekten
CN116023335A (zh) *	2022-12-28	2023-04-28	河北科技大学	一种苯甲酰脲衍生物及其制备方法和应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1525861A (fr) *	1963-10-28	1968-05-24	Boots Pure Drug Co Ltd	Nouveaux carbamates, leur procédé de préparation et leurs applications comme pesticides
US3933908A (en) *	1970-05-15	1976-01-20	U.S. Philips Corporation	Substituted benzoyl ureas
EG11837A (en) *	1974-09-19	1977-12-31	Lilly Co Eli	Novel 1-(substituted benzoyl)-3-(substituted pyrazinyl ureas used as insecticides

1978
- 1978-06-16 FR FR7818187A patent/FR2398738A1/fr active Granted
- 1978-06-19 AU AU37249/78A patent/AU516505B2/en not_active Expired
- 1978-06-19 PT PT68189A patent/PT68189A/pt unknown
- 1978-06-19 GB GB7827260A patent/GB2001053B/en not_active Expired
- 1978-06-19 AT AT0445678A patent/AT367046B/de not_active IP Right Cessation
- 1978-06-19 YU YU01440/78A patent/YU144078A/xx unknown
- 1978-06-19 DE DE19782826893 patent/DE2826893A1/de not_active Withdrawn
- 1978-06-20 TR TR20446A patent/TR20446A/tr unknown
- 1978-06-20 RO RO7894410A patent/RO78069A/ro unknown
- 1978-06-20 GR GR56554A patent/GR72967B/el unknown
- 1978-06-21 DK DK279378A patent/DK279378A/da not_active Application Discontinuation
- 1978-06-21 IT IT24809/78A patent/IT1096793B/it active
- 1978-06-21 SE SE7807127A patent/SE7807127L/xx unknown
- 1978-06-21 NL NL7806678A patent/NL7806678A/xx not_active Application Discontinuation
- 1978-06-21 CH CH677078A patent/CH638500A5/de not_active IP Right Cessation
- 1978-06-21 BR BR787803939A patent/BR7803939A/pt unknown
- 1978-06-22 BG BG041706A patent/BG30174A4/xx unknown
- 1978-06-22 BG BG040168A patent/BG30017A3/xx unknown
- 1978-06-22 JP JP7634378A patent/JPS549288A/ja active Pending
- 1978-06-22 DD DD78206203A patent/DD141831A5/de unknown
- 1978-06-22 OA OA56534A patent/OA06108A/xx unknown

Also Published As

Publication number	Publication date
OA06108A (fr)	1981-06-30
YU144078A (en)	1982-10-31
BG30174A4 (en)	1981-04-15
BG30017A3 (en)	1981-03-16
NL7806678A (nl)	1978-12-28
TR20446A (tr)	1981-07-14
JPS549288A (en)	1979-01-24
GB2001053A (en)	1979-01-24
PT68189A (en)	1978-07-01
AT367046B (de)	1982-05-25
FR2398738A1 (fr)	1979-02-23
IT7824809A0 (it)	1978-06-21
ATA445678A (de)	1981-10-15
BR7803939A (pt)	1979-02-20
IT1096793B (it)	1985-08-26
GR72967B (tr)	1984-01-20
RO78069A (ro)	1983-08-03
FR2398738B1 (tr)	1981-05-08
RO78069B (ro)	1983-07-30
GB2001053B (en)	1982-05-26
DE2826893A1 (de)	1979-01-18
AU516505B2 (en)	1981-06-04
DD141831A5 (de)	1980-05-21
SE7807127L (sv)	1978-12-23
AU3724978A (en)	1980-01-03
DK279378A (da)	1978-12-23

Legal Events

Date	Code	Title	Description
1987-02-27	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0306696B1 (de)	1994-02-16	Substituierte Guanidine
EP0303570A2 (de)	1989-02-15	Substituierte Isothioharnstoffe
EP0302833A2 (de)	1989-02-08	1-Nitro-2,2-diaminoäthylenderivate
EP0077759A2 (de)	1983-04-27	Phenylharnstoffe
DE2541116C2 (de)	1985-07-18	1-(Substituierte-benzoyl)-3-(substituierte-pyrazinyl)-harnstoffe, Verfahren zu ihrer Herstellung und sie enthaltendes insektizides Mittel
US4293552A (en)	1981-10-06	Novel 1-(mono-o-substituted benzoyl)-3-(substituted pyrazinyl) ureas
EP0320448B1 (de)	1994-12-28	3-Aminobenzoylphenylharnstoffe
DD219101A5 (de)	1985-02-27	Zusammensetzung mit insektizider und akarizider wirksamkeit
CH638500A5 (de)	1983-09-30	1-(mono-o-substituierte-benzoyl)-3-(substituierte-pyrazinyl)-harnstoffe sowie diese verbindungen enthaltende insektizide.
EP0175649A2 (de)	1986-03-26	Substituierte Carbodiimide
EP0282452A2 (de)	1988-09-14	Phenoxyphenyl-thioharnstoffe, -isothioharnstoffe und -carbodiimide und ihre Verwendung bei der Kontrolle von Schädlingen
DE2704288A1 (de)	1977-08-18	Thiadiazolylbenzamide, verfahren zu ihrer herstellung und insekticide
DE2732115A1 (de)	1978-01-19	Oxadiazinderivate, verfahren zu ihrer herstellung und solche verbindungen enthaltende insektizide
DD219102A5 (de)	1985-02-27	Zusammensetzung mit insektizider und akarizider wirksamkeit
DE3141232A1 (de)	1982-06-24	Harnstoffe mit heterozyclischer aether- oder thioaetherbindung
DD145220A5 (de)	1980-12-03	Insektizide mittel
DE2256275A1 (de)	1973-05-24	Neue substituierte harnstoffverbindungen und verfahren zu ihrer herstellung
EP0288432A1 (de)	1988-10-26	Schädlingsbekämpfungsmittel
DE2524578A1 (de)	1975-12-11	Barbitursaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide
DD143721A5 (de)	1980-09-10	Insektizides mittel
CH624406A5 (tr)	1981-07-31
CH625209A5 (en)	1981-09-15	Process for the preparation of novel aminothiocarbamates and their use as active ingredient in pesticides
EP0375613A2 (de)	1990-06-27	Nitroenamine
AT360800B (de)	1981-01-26	Insektizides mittel
EP0230863A2 (de)	1987-08-05	Oxadiazinone