DE3204365A1 - Substituierte phenylcarbamoylbenzimidate - Google Patents
Substituierte phenylcarbamoylbenzimidateInfo
- Publication number
- DE3204365A1 DE3204365A1 DE19823204365 DE3204365A DE3204365A1 DE 3204365 A1 DE3204365 A1 DE 3204365A1 DE 19823204365 DE19823204365 DE 19823204365 DE 3204365 A DE3204365 A DE 3204365A DE 3204365 A1 DE3204365 A1 DE 3204365A1
- Authority
- DE
- Germany
- Prior art keywords
- chloro
- ethyl
- carbonyl
- nitrophenoxy
- dichloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- ZIEOTAZTRSLSDH-UHFFFAOYSA-N phenylcarbamoyl benzenecarboximidate Chemical class C=1C=CC=CC=1C(=N)OC(=O)NC1=CC=CC=C1 ZIEOTAZTRSLSDH-UHFFFAOYSA-N 0.000 title claims description 6
- 239000000460 chlorine Substances 0.000 claims description 84
- -1 alkyl radical Chemical group 0.000 claims description 78
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 49
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- KXDAEFPNCMNJSK-UHFFFAOYSA-M benzenecarboximidate Chemical compound [NH-]C(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-M 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 241000238631 Hexapoda Species 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 241000607479 Yersinia pestis Species 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000002917 insecticide Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 9
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 2
- 150000002463 imidates Chemical class 0.000 claims 2
- AVRQBXVUUXHRMY-UHFFFAOYSA-N 2,6-difluorobenzamide Chemical compound NC(=O)C1=C(F)C=CC=C1F AVRQBXVUUXHRMY-UHFFFAOYSA-N 0.000 claims 1
- XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 38
- 238000004458 analytical method Methods 0.000 description 26
- 238000009472 formulation Methods 0.000 description 23
- 239000002904 solvent Substances 0.000 description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000012876 carrier material Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000001819 mass spectrum Methods 0.000 description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000428 dust Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 206010061217 Infestation Diseases 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- KZKYRHRAVGWEAV-UHFFFAOYSA-N 2,3-dichlorobenzamide Chemical compound NC(=O)C1=CC=CC(Cl)=C1Cl KZKYRHRAVGWEAV-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 3
- 230000002745 absorbent Effects 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- AGDGFRKBQPTFFA-UHFFFAOYSA-N ethyl 2-chloro-n-[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]carbamoyl]benzenecarboximidate Chemical compound C=1C=CC=C(Cl)C=1C(OCC)=NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C([N+]([O-])=O)C=C1 AGDGFRKBQPTFFA-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RBGDLYUEXLWQBZ-UHFFFAOYSA-N 2-chlorobenzamide Chemical compound NC(=O)C1=CC=CC=C1Cl RBGDLYUEXLWQBZ-UHFFFAOYSA-N 0.000 description 2
- FKRDYPAKVOATQY-UHFFFAOYSA-N 2-fluorosulfonyloxypropane Chemical compound CC(C)OS(F)(=O)=O FKRDYPAKVOATQY-UHFFFAOYSA-N 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 240000007049 Juglans regia Species 0.000 description 2
- 235000009496 Juglans regia Nutrition 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000008157 edible vegetable oil Substances 0.000 description 2
- SSTOHELFUZUDNP-UHFFFAOYSA-N ethyl n-[[3-chloro-4-(3-chloro-4-nitrophenoxy)phenyl]carbamoyl]-2-methylbenzenecarboximidate Chemical compound C=1C=CC=C(C)C=1C(OCC)=NC(=O)NC(C=C1Cl)=CC=C1OC1=CC=C([N+]([O-])=O)C(Cl)=C1 SSTOHELFUZUDNP-UHFFFAOYSA-N 0.000 description 2
- ZAGRGDBCCKLLHX-UHFFFAOYSA-N ethyl n-[[3-chloro-4-(4-nitrophenoxy)phenyl]carbamoyl]-2,6-difluorobenzenecarboximidate Chemical compound FC=1C=CC=C(F)C=1C(OCC)=NC(=O)NC(C=C1Cl)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 ZAGRGDBCCKLLHX-UHFFFAOYSA-N 0.000 description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 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
- 239000003350 kerosene Substances 0.000 description 2
- DVPHQZIPXYJHEN-UHFFFAOYSA-N methyl n-[[3-chloro-4-(4-nitrophenoxy)phenyl]carbamoyl]-2-methylbenzenecarboximidate Chemical compound C=1C=CC=C(C)C=1C(OC)=NC(=O)NC(C=C1Cl)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 DVPHQZIPXYJHEN-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 150000007530 organic bases Chemical group 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000020234 walnut Nutrition 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- XUXUUURPTHYGBU-UHFFFAOYSA-N 1,3,5-oxadiazine-2,4-dione Chemical class O=C1N=COC(=O)N1 XUXUUURPTHYGBU-UHFFFAOYSA-N 0.000 description 1
- LNGMHNWZUQMDPT-UHFFFAOYSA-N 1,3-dichloro-5-isocyanato-2-(4-nitrophenoxy)benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=C(Cl)C=C(N=C=O)C=C1Cl LNGMHNWZUQMDPT-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- KGGHWIKBOIQEAJ-UHFFFAOYSA-N 2-fluorobenzamide Chemical compound NC(=O)C1=CC=CC=C1F KGGHWIKBOIQEAJ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000000073 Amphicarpaea bracteata Nutrition 0.000 description 1
- 240000002470 Amphicarpaea bracteata Species 0.000 description 1
- 241000239223 Arachnida Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 108010011438 H 77 Proteins 0.000 description 1
- 241000256244 Heliothis virescens Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- WFBHRSAKANVBKH-UHFFFAOYSA-N N-hydroxyguanidine Chemical class NC(=N)NO WFBHRSAKANVBKH-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241000255993 Trichoplusia ni Species 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- DEDLMUPSQBVPGV-UHFFFAOYSA-N carbonochloridoyl benzenecarboximidate Chemical compound ClC(=O)OC(=N)C1=CC=CC=C1 DEDLMUPSQBVPGV-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- MMCNSCJDASKPPT-UHFFFAOYSA-N ethyl n-[[3,5-dichloro-4-(3-chloro-4-nitrophenoxy)phenyl]carbamoyl]-2,6-difluorobenzenecarboximidate Chemical compound FC=1C=CC=C(F)C=1C(OCC)=NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C([N+]([O-])=O)C(Cl)=C1 MMCNSCJDASKPPT-UHFFFAOYSA-N 0.000 description 1
- YRSCAUCSMBQPKV-UHFFFAOYSA-N ethyl n-[[3,5-dichloro-4-(3-chloro-4-nitrophenoxy)phenyl]carbamoyl]-2-fluorobenzenecarboximidate Chemical compound C=1C=CC=C(F)C=1C(OCC)=NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C([N+]([O-])=O)C(Cl)=C1 YRSCAUCSMBQPKV-UHFFFAOYSA-N 0.000 description 1
- HZMBNYUPCQQUIO-UHFFFAOYSA-N ethyl n-[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]carbamoyl]-2,6-difluorobenzenecarboximidate Chemical compound FC=1C=CC=C(F)C=1C(OCC)=NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C([N+]([O-])=O)C=C1 HZMBNYUPCQQUIO-UHFFFAOYSA-N 0.000 description 1
- CHQGWBVTSNWGHO-UHFFFAOYSA-N ethyl n-[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]carbamoyl]-2-fluorobenzenecarboximidate Chemical compound C=1C=CC=C(F)C=1C(OCC)=NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C([N+]([O-])=O)C=C1 CHQGWBVTSNWGHO-UHFFFAOYSA-N 0.000 description 1
- LHTIHZXHEJMKBE-UHFFFAOYSA-N ethyl n-[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]carbamoyl]-2-methylbenzenecarboximidate Chemical compound C=1C=CC=C(C)C=1C(OCC)=NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C([N+]([O-])=O)C=C1 LHTIHZXHEJMKBE-UHFFFAOYSA-N 0.000 description 1
- VVPNTCPXOPQWQY-UHFFFAOYSA-N ethyl n-[[3-chloro-4-(3-chloro-4-nitrophenoxy)phenyl]carbamoyl]-2-fluorobenzenecarboximidate Chemical compound C=1C=CC=C(F)C=1C(OCC)=NC(=O)NC(C=C1Cl)=CC=C1OC1=CC=C([N+]([O-])=O)C(Cl)=C1 VVPNTCPXOPQWQY-UHFFFAOYSA-N 0.000 description 1
- AZYZEEBQNRJBLW-UHFFFAOYSA-N ethyl n-[[3-chloro-4-(4-nitrophenoxy)phenyl]carbamoyl]-2-fluorobenzenecarboximidate Chemical compound C=1C=CC=C(F)C=1C(OCC)=NC(=O)NC(C=C1Cl)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 AZYZEEBQNRJBLW-UHFFFAOYSA-N 0.000 description 1
- YIMYQLLCUOWFKA-UHFFFAOYSA-N ethyl n-[[3-chloro-4-(4-nitrophenoxy)phenyl]carbamoyl]-2-methylbenzenecarboximidate Chemical compound C=1C=CC=C(C)C=1C(OCC)=NC(=O)NC(C=C1Cl)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 YIMYQLLCUOWFKA-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- ZUUKCAGXFJISCO-UHFFFAOYSA-N methyl n-[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]carbamoyl]-2-fluorobenzenecarboximidate Chemical compound C=1C=CC=C(F)C=1C(OC)=NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C([N+]([O-])=O)C=C1 ZUUKCAGXFJISCO-UHFFFAOYSA-N 0.000 description 1
- IEHSWIOLRUGGAG-UHFFFAOYSA-N methyl n-[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]carbamoyl]-2-methylbenzenecarboximidate Chemical compound C=1C=CC=C(C)C=1C(OC)=NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C([N+]([O-])=O)C=C1 IEHSWIOLRUGGAG-UHFFFAOYSA-N 0.000 description 1
- GHNQTZJOHVZWPS-UHFFFAOYSA-N methyl n-[[3-chloro-4-(3-chloro-4-nitrophenoxy)phenyl]carbamoyl]-2-fluorobenzenecarboximidate Chemical compound C=1C=CC=C(F)C=1C(OC)=NC(=O)NC(C=C1Cl)=CC=C1OC1=CC=C([N+]([O-])=O)C(Cl)=C1 GHNQTZJOHVZWPS-UHFFFAOYSA-N 0.000 description 1
- KOQFKPFSEFBFHW-UHFFFAOYSA-N methyl n-[[3-chloro-4-(4-nitrophenoxy)phenyl]carbamoyl]-2,6-difluorobenzenecarboximidate Chemical compound FC=1C=CC=C(F)C=1C(OC)=NC(=O)NC(C=C1Cl)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 KOQFKPFSEFBFHW-UHFFFAOYSA-N 0.000 description 1
- IRFKBXILUFJTSP-UHFFFAOYSA-N methyl n-[[3-chloro-4-(4-nitrophenoxy)phenyl]carbamoyl]-2-fluorobenzenecarboximidate Chemical compound C=1C=CC=C(F)C=1C(OC)=NC(=O)NC(C=C1Cl)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 IRFKBXILUFJTSP-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- WURRQEISZWOWBD-UHFFFAOYSA-N n-[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(C(=C1)Cl)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F WURRQEISZWOWBD-UHFFFAOYSA-N 0.000 description 1
- GYNAVKULVOETAD-UHFFFAOYSA-N n-phenoxyaniline Chemical class C=1C=CC=CC=1NOC1=CC=CC=C1 GYNAVKULVOETAD-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- DIOCUWHZXCPFTP-UHFFFAOYSA-N propan-2-yl 2,6-dichloro-n-[[3-chloro-4-(4-nitrophenoxy)phenyl]carbamoyl]benzenecarboximidate Chemical compound ClC=1C=CC=C(Cl)C=1C(OC(C)C)=NC(=O)NC(C=C1Cl)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 DIOCUWHZXCPFTP-UHFFFAOYSA-N 0.000 description 1
- AGJWDYZXJKUIOR-UHFFFAOYSA-N propan-2-yl 2-chlorobenzenecarboximidate Chemical compound CC(C)OC(=N)C1=CC=CC=C1Cl AGJWDYZXJKUIOR-UHFFFAOYSA-N 0.000 description 1
- SXFDFVGXGDWJLR-UHFFFAOYSA-N propan-2-yl n-[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]carbamoyl]-2-fluorobenzenecarboximidate Chemical compound C=1C=CC=C(F)C=1C(OC(C)C)=NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C([N+]([O-])=O)C=C1 SXFDFVGXGDWJLR-UHFFFAOYSA-N 0.000 description 1
- RAAFOHLXLSCKJR-UHFFFAOYSA-N propan-2-yl n-[[3-chloro-4-(4-nitrophenoxy)phenyl]carbamoyl]-2-fluorobenzenecarboximidate Chemical compound C=1C=CC=C(F)C=1C(OC(C)C)=NC(=O)NC(C=C1Cl)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 RAAFOHLXLSCKJR-UHFFFAOYSA-N 0.000 description 1
- SYKSOZCIMBNPBS-UHFFFAOYSA-N propan-2-yl n-[[3-chloro-4-(4-nitrophenoxy)phenyl]carbamoyl]-2-methylbenzenecarboximidate Chemical compound C=1C=CC=C(C)C=1C(OC(C)C)=NC(=O)NC(C=C1Cl)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 SYKSOZCIMBNPBS-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000000926 separation method 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012749 thinning agent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/44—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups doubly-bound to carbon atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23300981A | 1981-02-09 | 1981-02-09 | |
| US06/326,895 US4357347A (en) | 1981-02-09 | 1981-12-04 | Pesticidal phenylcarbamoylbenzimidates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3204365A1 true DE3204365A1 (de) | 1983-01-20 |
Family
ID=26926546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823204365 Withdrawn DE3204365A1 (de) | 1981-02-09 | 1982-02-09 | Substituierte phenylcarbamoylbenzimidate |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4357347A (OSRAM) |
| CA (1) | CA1221705A (OSRAM) |
| CH (1) | CH653323A5 (OSRAM) |
| DE (1) | DE3204365A1 (OSRAM) |
| FR (1) | FR2499562A1 (OSRAM) |
| GB (1) | GB2092587B (OSRAM) |
| IT (1) | IT8247726A0 (OSRAM) |
| NL (1) | NL8200290A (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0109211A1 (en) * | 1982-11-05 | 1984-05-23 | Imperial Chemical Industries Plc | Pyridine derivatives |
| US4723015A (en) * | 1983-10-17 | 1988-02-02 | Ciba-Geigy Corporation | Certain insecticidal N-2-pyridyloxyphenylbenzimidates |
| EP0199945A3 (de) * | 1985-03-23 | 1988-08-03 | Hoechst Aktiengesellschaft | Neue Carbamoylarylcarboximidsäureester, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel |
Family Cites Families (7)
| 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. |
| DE2438747C2 (de) * | 1974-08-13 | 1982-10-14 | Bayer Ag, 5090 Leverkusen | Benzoylureido-diphenyläther, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
| DE2637947C2 (de) * | 1976-08-24 | 1985-09-19 | Bayer Ag, 5090 Leverkusen | Tetrafluor-1,3-benzodioxanyl-benzoylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
| US4160834A (en) * | 1977-03-09 | 1979-07-10 | Eli Lilly And Company | 1-(Substituted benzoyl)-3-(substituted pyrazinyl)ureas |
| US4170657A (en) * | 1977-05-13 | 1979-10-09 | The Dow Chemical Company | Substituted(((phenyl)amino)carbonyl)-benzamides |
| GB2025396A (en) * | 1978-06-02 | 1980-01-23 | Ici Ltd | Substituted benzoylimidates their preparation and compositions comprising them for insecticidal use |
| US4200653A (en) * | 1978-09-29 | 1980-04-29 | Imperial Chemical Industries Limited | Insecticidal compound and method of use |
-
1981
- 1981-12-04 US US06/326,895 patent/US4357347A/en not_active Expired - Fee Related
-
1982
- 1982-01-11 CA CA000393867A patent/CA1221705A/en not_active Expired
- 1982-01-27 NL NL8200290A patent/NL8200290A/nl not_active Application Discontinuation
- 1982-02-04 IT IT8247726A patent/IT8247726A0/it unknown
- 1982-02-05 CH CH722/82A patent/CH653323A5/de not_active IP Right Cessation
- 1982-02-08 FR FR8201980A patent/FR2499562A1/fr active Granted
- 1982-02-08 GB GB8203541A patent/GB2092587B/en not_active Expired
- 1982-02-09 DE DE19823204365 patent/DE3204365A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB2092587B (en) | 1985-04-03 |
| GB2092587A (en) | 1982-08-18 |
| US4357347A (en) | 1982-11-02 |
| NL8200290A (nl) | 1982-09-01 |
| IT8247726A0 (it) | 1982-02-04 |
| FR2499562A1 (fr) | 1982-08-13 |
| FR2499562B1 (OSRAM) | 1984-12-21 |
| CH653323A5 (de) | 1985-12-31 |
| CA1221705A (en) | 1987-05-12 |
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