JPS6150940B2 - - Google Patents
Info
- Publication number
- JPS6150940B2 JPS6150940B2 JP56163544A JP16354481A JPS6150940B2 JP S6150940 B2 JPS6150940 B2 JP S6150940B2 JP 56163544 A JP56163544 A JP 56163544A JP 16354481 A JP16354481 A JP 16354481A JP S6150940 B2 JPS6150940 B2 JP S6150940B2
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- naphthoxy
- hydrogen
- urea
- carbon atoms
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 60
- 239000001257 hydrogen Substances 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical group 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 18
- 239000004202 carbamide Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- -1 chloro, bromo, methyl Chemical group 0.000 claims description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 229910052727 yttrium Inorganic materials 0.000 claims description 14
- 230000000749 insecticidal effect Effects 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000006684 polyhaloalkyl group Chemical group 0.000 claims description 10
- 125000001246 bromo group Chemical group Br* 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- OCJCYPHQCOKFRH-UHFFFAOYSA-N 4-(sulfamoylamino)morpholine Chemical compound NS(=O)(=O)NN1CCOCC1 OCJCYPHQCOKFRH-UHFFFAOYSA-N 0.000 claims description 5
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 5
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical compound NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 claims description 4
- 230000000895 acaricidal effect Effects 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 239000000642 acaricide Substances 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 3
- QBSJUWMQKAFHCL-UHFFFAOYSA-N 2-chloro-n-[[3,5-dichloro-4-(4-methoxynaphthalen-1-yl)oxyphenyl]carbamoyl]benzamide Chemical compound C12=CC=CC=C2C(OC)=CC=C1OC(C(=C1)Cl)=C(Cl)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl QBSJUWMQKAFHCL-UHFFFAOYSA-N 0.000 claims description 2
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 20
- 125000004429 atom Chemical group 0.000 claims 2
- 125000006333 difluoro benzoyl group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000006332 fluoro benzoyl group Chemical group 0.000 claims 1
- PPOSFCNLNROPTA-UHFFFAOYSA-N n-carbamoyl-2,6-difluorobenzamide Chemical compound NC(=O)NC(=O)C1=C(F)C=CC=C1F PPOSFCNLNROPTA-UHFFFAOYSA-N 0.000 claims 1
- ZGOLQMOPAHHQCC-UHFFFAOYSA-N n-carbamoyl-2-chlorobenzamide Chemical compound NC(=O)NC(=O)C1=CC=CC=C1Cl ZGOLQMOPAHHQCC-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 238000012360 testing method Methods 0.000 description 28
- 239000000243 solution Substances 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 235000013877 carbamide Nutrition 0.000 description 17
- 239000007787 solid Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- 241000712024 Brassica rapa var. perviridis Species 0.000 description 7
- 241000462639 Epilachna varivestis Species 0.000 description 7
- 238000007865 diluting Methods 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 150000008047 benzoylureas Chemical class 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 235000013601 eggs Nutrition 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RTYDKESMWNGDJB-UHFFFAOYSA-N 2-chloro-n-[[4-[(4-chloro-5,6,7,8-tetrahydronaphthalen-1-yl)oxy]-3,5-dimethylphenyl]carbamoyl]benzamide Chemical compound C=1C(C)=C(OC=2C=3CCCCC=3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=CC=CC=C1Cl RTYDKESMWNGDJB-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241001477931 Mythimna unipuncta Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 241000256244 Heliothis virescens Species 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- SSABAIUCBWJKMS-UHFFFAOYSA-N 1-(2-methyl-4-nitrophenoxy)naphthalene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1OC1=CC=CC2=CC=CC=C12 SSABAIUCBWJKMS-UHFFFAOYSA-N 0.000 description 2
- ZRJSABISRHPRSB-UHFFFAOYSA-N 2,6-difluorobenzoyl isocyanate Chemical compound FC1=CC=CC(F)=C1C(=O)N=C=O ZRJSABISRHPRSB-UHFFFAOYSA-N 0.000 description 2
- BEDBKXPDLSNXLZ-UHFFFAOYSA-N 2-chloro-N-[[3,5-dichloro-4-[(4-chloro-2,2-dimethyl-3H-1-benzofuran-7-yl)oxy]phenyl]carbamoyl]benzamide Chemical compound O1C(C)(C)CC(C(=CC=2)Cl)=C1C=2OC(C(=C1)Cl)=C(Cl)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl BEDBKXPDLSNXLZ-UHFFFAOYSA-N 0.000 description 2
- AEXYNFUGMURXDE-UHFFFAOYSA-N 2-chloro-n-[[4-[(4-chloro-5,6,7,8-tetrahydronaphthalen-1-yl)oxy]-3,5-dimethylphenyl]carbamoyl]-6-fluorobenzamide Chemical compound C=1C(C)=C(OC=2C=3CCCCC=3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=C(F)C=CC=C1Cl AEXYNFUGMURXDE-UHFFFAOYSA-N 0.000 description 2
- IVKRGQOBLBLKCF-UHFFFAOYSA-N 3,5-dichloro-4-[(4-chloro-5,6,7,8-tetrahydronaphthalen-1-yl)oxy]aniline Chemical compound ClC1=CC(N)=CC(Cl)=C1OC1=CC=C(Cl)C2=C1CCCC2 IVKRGQOBLBLKCF-UHFFFAOYSA-N 0.000 description 2
- AZPLDWUVJDZSRT-UHFFFAOYSA-N 3-chloro-4-(4-chloronaphthalen-1-yl)oxy-5-methylaniline Chemical compound CC1=CC(N)=CC(Cl)=C1OC1=CC=C(Cl)C2=CC=CC=C12 AZPLDWUVJDZSRT-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 235000008744 Brassica perviridis Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 101000834981 Homo sapiens Testis, prostate and placenta-expressed protein Proteins 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- IDCBOTIENDVCBQ-UHFFFAOYSA-N TEPP Chemical compound CCOP(=O)(OCC)OP(=O)(OCC)OCC IDCBOTIENDVCBQ-UHFFFAOYSA-N 0.000 description 2
- 244000204900 Talipariti tiliaceum Species 0.000 description 2
- 102100026164 Testis, prostate and placenta-expressed protein Human genes 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000013020 final formulation Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- USHNBYAESHYOTF-UHFFFAOYSA-N n-[[3,5-dichloro-4-[(4-chloro-5,6,7,8-tetrahydronaphthalen-1-yl)oxy]phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C(Cl)C2=C1CCCC2 USHNBYAESHYOTF-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- HHLCSFGOTLUREE-UHFFFAOYSA-N 1,2,3-trichloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C(Cl)=C1 HHLCSFGOTLUREE-UHFFFAOYSA-N 0.000 description 1
- NTBYINQTYWZXLH-UHFFFAOYSA-N 1,2-dichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1 NTBYINQTYWZXLH-UHFFFAOYSA-N 0.000 description 1
- CAKUTMRWSRMBOD-UHFFFAOYSA-N 1,6-dibromo-2-(2-chloro-4-nitrophenoxy)naphthalene Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(C=C(Br)C=C2)C2=C1Br CAKUTMRWSRMBOD-UHFFFAOYSA-N 0.000 description 1
- ZVCXPVRMAMOLPZ-UHFFFAOYSA-N 1-(2,6-dichloro-4-nitrophenoxy)-4-methoxynaphthalene Chemical compound C12=CC=CC=C2C(OC)=CC=C1OC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl ZVCXPVRMAMOLPZ-UHFFFAOYSA-N 0.000 description 1
- TVRWTDNWNBEWRF-UHFFFAOYSA-N 1-(2,6-dichloro-4-nitrophenoxy)naphthalene Chemical compound ClC1=CC([N+](=O)[O-])=CC(Cl)=C1OC1=CC=CC2=CC=CC=C12 TVRWTDNWNBEWRF-UHFFFAOYSA-N 0.000 description 1
- OZFULEFWNGEJPB-UHFFFAOYSA-N 1-(2-chloro-4-nitrophenoxy)-4-methoxynaphthalene Chemical compound C12=CC=CC=C2C(OC)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1Cl OZFULEFWNGEJPB-UHFFFAOYSA-N 0.000 description 1
- ICUAYKKPVLQPRD-UHFFFAOYSA-N 1-(2-chloro-4-nitrophenoxy)naphthalene Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC2=CC=CC=C12 ICUAYKKPVLQPRD-UHFFFAOYSA-N 0.000 description 1
- OAGXKEOTRBGZAD-UHFFFAOYSA-N 1-(2-chloro-6-methyl-4-nitrophenoxy)-4-methoxynaphthalene Chemical compound C12=CC=CC=C2C(OC)=CC=C1OC1=C(C)C=C([N+]([O-])=O)C=C1Cl OAGXKEOTRBGZAD-UHFFFAOYSA-N 0.000 description 1
- SEGARSYGUBYPOK-UHFFFAOYSA-N 1-(4-nitrophenoxy)naphthalene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC2=CC=CC=C12 SEGARSYGUBYPOK-UHFFFAOYSA-N 0.000 description 1
- YPECNVBQNYHRLT-UHFFFAOYSA-N 1-[4-nitro-2-(trifluoromethyl)phenoxy]naphthalene Chemical compound FC(F)(F)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC2=CC=CC=C12 YPECNVBQNYHRLT-UHFFFAOYSA-N 0.000 description 1
- BMRZGYNNZTVECK-UHFFFAOYSA-N 1-benzothiophen-4-ol Chemical compound OC1=CC=CC2=C1C=CS2 BMRZGYNNZTVECK-UHFFFAOYSA-N 0.000 description 1
- IBRWLEYNCGRJLX-UHFFFAOYSA-N 1-chloro-2-(isocyanatomethyl)benzene Chemical compound ClC1=CC=CC=C1CN=C=O IBRWLEYNCGRJLX-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- MTAYXWYDFAVWNS-UHFFFAOYSA-N 1-chloro-4-(2,5-dimethyl-4-nitrophenoxy)naphthalene Chemical compound CC1=CC([N+]([O-])=O)=C(C)C=C1OC1=CC=C(Cl)C2=CC=CC=C12 MTAYXWYDFAVWNS-UHFFFAOYSA-N 0.000 description 1
- RXSMLBWJRMZIKZ-UHFFFAOYSA-N 1-chloro-4-(2,6-dibromo-4-nitrophenoxy)naphthalene Chemical compound BrC1=CC([N+](=O)[O-])=CC(Br)=C1OC1=CC=C(Cl)C2=CC=CC=C12 RXSMLBWJRMZIKZ-UHFFFAOYSA-N 0.000 description 1
- JSRVQLFAYPUINX-UHFFFAOYSA-N 1-chloro-4-(2,6-dimethyl-4-nitrophenoxy)naphthalene Chemical compound CC1=CC([N+]([O-])=O)=CC(C)=C1OC1=CC=C(Cl)C2=CC=CC=C12 JSRVQLFAYPUINX-UHFFFAOYSA-N 0.000 description 1
- GOJYNTBYLKVEHG-UHFFFAOYSA-N 1-chloro-4-(2-chloro-3,6-dimethyl-4-nitrophenoxy)naphthalene Chemical compound CC1=CC([N+]([O-])=O)=C(C)C(Cl)=C1OC1=CC=C(Cl)C2=CC=CC=C12 GOJYNTBYLKVEHG-UHFFFAOYSA-N 0.000 description 1
- ZGLWUHHCIGPNPK-UHFFFAOYSA-N 1-chloro-4-(2-chloro-4-nitrophenoxy)naphthalene Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C2=CC=CC=C12 ZGLWUHHCIGPNPK-UHFFFAOYSA-N 0.000 description 1
- ZXBUAMOYKGUYMS-UHFFFAOYSA-N 1-chloro-4-(2-chloro-5-methyl-4-nitrophenoxy)naphthalene Chemical compound C1=C([N+]([O-])=O)C(C)=CC(OC=2C3=CC=CC=C3C(Cl)=CC=2)=C1Cl ZXBUAMOYKGUYMS-UHFFFAOYSA-N 0.000 description 1
- MEYLVPCYDKRADV-UHFFFAOYSA-N 1-chloro-4-(2-chloro-6-methyl-4-nitrophenoxy)naphthalene Chemical compound CC1=CC([N+]([O-])=O)=CC(Cl)=C1OC1=CC=C(Cl)C2=CC=CC=C12 MEYLVPCYDKRADV-UHFFFAOYSA-N 0.000 description 1
- AJINYMKFYBKLHD-UHFFFAOYSA-N 1-chloro-4-(2-methoxy-4-nitrophenoxy)naphthalene Chemical compound COC1=CC([N+]([O-])=O)=CC=C1OC1=CC=C(Cl)C2=CC=CC=C12 AJINYMKFYBKLHD-UHFFFAOYSA-N 0.000 description 1
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- KTIAKBDLIZEUDF-UHFFFAOYSA-N 4-[(4-chloro-5,6,7,8-tetrahydronaphthalen-1-yl)oxy]-3-methoxyaniline Chemical compound COC1=CC(N)=CC=C1OC1=CC=C(Cl)C2=C1CCCC2 KTIAKBDLIZEUDF-UHFFFAOYSA-N 0.000 description 1
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- FAQOVTCZCJCNMG-UHFFFAOYSA-N 5-(2,6-dichloro-4-nitrophenoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound ClC1=CC([N+](=O)[O-])=CC(Cl)=C1OC1=CC=CC2=C1CCCC2 FAQOVTCZCJCNMG-UHFFFAOYSA-N 0.000 description 1
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- CJMCPWZBKQXHRM-UHFFFAOYSA-N 5-chloro-4-(4-chloronaphthalen-1-yl)oxy-2-methylaniline Chemical compound C1=C(N)C(C)=CC(OC=2C3=CC=CC=C3C(Cl)=CC=2)=C1Cl CJMCPWZBKQXHRM-UHFFFAOYSA-N 0.000 description 1
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- ZKGKTHNQAWJJOO-UHFFFAOYSA-N 5-chloro-8-(2-chloro-3,6-dimethyl-4-nitrophenoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound CC1=CC([N+]([O-])=O)=C(C)C(Cl)=C1OC1=CC=C(Cl)C2=C1CCCC2 ZKGKTHNQAWJJOO-UHFFFAOYSA-N 0.000 description 1
- IDCIJNOVKWOFLG-UHFFFAOYSA-N 5-chloro-8-(2-chloro-4-nitrophenoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C2=C1CCCC2 IDCIJNOVKWOFLG-UHFFFAOYSA-N 0.000 description 1
- ZDSUDOHXBRYNIV-UHFFFAOYSA-N 5-chloro-8-(2-chloro-5-methyl-4-nitrophenoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound C1=C([N+]([O-])=O)C(C)=CC(OC=2C=3CCCCC=3C(Cl)=CC=2)=C1Cl ZDSUDOHXBRYNIV-UHFFFAOYSA-N 0.000 description 1
- GBTZLCCCMCBBHN-UHFFFAOYSA-N 5-chloro-8-(2-chloro-6-methyl-4-nitrophenoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound CC1=CC([N+]([O-])=O)=CC(Cl)=C1OC1=CC=C(Cl)C2=C1CCCC2 GBTZLCCCMCBBHN-UHFFFAOYSA-N 0.000 description 1
- CLNKSTRRSYPETQ-UHFFFAOYSA-N 5-chloro-8-(2-methyl-4-nitrophenoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1OC1=CC=C(Cl)C2=C1CCCC2 CLNKSTRRSYPETQ-UHFFFAOYSA-N 0.000 description 1
- RYFXATWELZSPFI-UHFFFAOYSA-N 5-chloro-8-(4-nitrophenoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C2=C1CCCC2 RYFXATWELZSPFI-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241001388466 Bruchus rufimanus Species 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- 241000255967 Helicoverpa zea Species 0.000 description 1
- 241000256257 Heliothis Species 0.000 description 1
- 102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 241000819999 Nymphes Species 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 210000003278 egg shell Anatomy 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- WITXNXRFMINJJB-UHFFFAOYSA-N n-[4-(1-benzofuran-4-yloxy)-3,5-dichlorophenyl]-n-carbamoyl-2,6-difluorobenzamide Chemical compound C=1C(Cl)=C(OC=2C=3C=COC=3C=CC=2)C(Cl)=CC=1N(C(=O)N)C(=O)C1=C(F)C=CC=C1F WITXNXRFMINJJB-UHFFFAOYSA-N 0.000 description 1
- PUKSAIDWQFMGIQ-UHFFFAOYSA-N n-[[3,5-dibromo-4-[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxy]phenyl]carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=C1Br)=CC(Br)=C1OC1=CC=CC2=C1OC(C)(C)C2 PUKSAIDWQFMGIQ-UHFFFAOYSA-N 0.000 description 1
- BTQLULHYSPZZLH-UHFFFAOYSA-N n-[[3,5-dichloro-4-(1,6-dichloronaphthalen-2-yl)oxyphenyl]carbamoyl]-2,4-difluoropyridine-3-carboxamide Chemical compound FC1=CC=NC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C(C=C(Cl)C=C2)C2=C1Cl BTQLULHYSPZZLH-UHFFFAOYSA-N 0.000 description 1
- BWGFWFLTOYOZTO-UHFFFAOYSA-N n-[[3,5-dichloro-4-(4-chloronaphthalen-1-yl)oxyphenyl]carbamoyl]-2,4-difluoropyridine-3-carboxamide Chemical compound FC1=CC=NC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C(Cl)C2=CC=CC=C12 BWGFWFLTOYOZTO-UHFFFAOYSA-N 0.000 description 1
- MFESPQTXJWRQEB-UHFFFAOYSA-N n-[[3,5-dichloro-4-(4-methoxynaphthalen-1-yl)oxyphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C12=CC=CC=C2C(OC)=CC=C1OC(C(=C1)Cl)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F MFESPQTXJWRQEB-UHFFFAOYSA-N 0.000 description 1
- XPDZDIIOLUDUIZ-UHFFFAOYSA-N n-[[3,5-dichloro-4-[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxy]phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C=12OC(C)(C)CC2=CC=CC=1OC(C(=C1)Cl)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F XPDZDIIOLUDUIZ-UHFFFAOYSA-N 0.000 description 1
- QPXDKZYLNXEKGM-UHFFFAOYSA-N n-[[3,5-dichloro-4-[(4-chloro-2,2-dimethyl-3h-1-benzofuran-7-yl)oxy]phenyl]carbamoyl]-2,6-dimethoxybenzamide Chemical compound COC1=CC=CC(OC)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C(Cl)C2=C1OC(C)(C)C2 QPXDKZYLNXEKGM-UHFFFAOYSA-N 0.000 description 1
- SCRUEOLDXICPQL-UHFFFAOYSA-N n-[[3-chloro-4-(4-chloronaphthalen-1-yl)oxy-2,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound CC=1C(Cl)=C(OC=2C3=CC=CC=C3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=C(F)C=CC=C1F SCRUEOLDXICPQL-UHFFFAOYSA-N 0.000 description 1
- KUIHEXLVCPKJPS-UHFFFAOYSA-N n-[[3-chloro-4-[4-(dimethylamino)naphthalen-1-yl]oxyphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C12=CC=CC=C2C(N(C)C)=CC=C1OC(C(=C1)Cl)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F KUIHEXLVCPKJPS-UHFFFAOYSA-N 0.000 description 1
- UYEGOSJNEGUNHJ-UHFFFAOYSA-N n-[[3-chloro-4-[[4-(dimethylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]oxy]-5-methylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C1=2CCCCC=2C(N(C)C)=CC=C1OC(C(=C1)Cl)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F UYEGOSJNEGUNHJ-UHFFFAOYSA-N 0.000 description 1
- IGSDYKAWCHNGNM-UHFFFAOYSA-N n-[[4-(4-chloronaphthalen-1-yl)oxy-3-methylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C=1C=C(OC=2C3=CC=CC=C3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=C(F)C=CC=C1F IGSDYKAWCHNGNM-UHFFFAOYSA-N 0.000 description 1
- BHFHZBRZXNSUHG-UHFFFAOYSA-N n-[[4-[(4-chloro-5,6,7,8-tetrahydronaphthalen-1-yl)oxy]-3,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C=1C(C)=C(OC=2C=3CCCCC=3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=C(F)C=CC=C1F BHFHZBRZXNSUHG-UHFFFAOYSA-N 0.000 description 1
- MPKRBINVMQZSBU-UHFFFAOYSA-N n-[[4-[(4-chloro-5,6,7,8-tetrahydronaphthalen-1-yl)oxy]-3-methylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C=1C=C(OC=2C=3CCCCC=3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=C(F)C=CC=C1F MPKRBINVMQZSBU-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19759580A | 1980-10-16 | 1980-10-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57158753A JPS57158753A (en) | 1982-09-30 |
| JPS6150940B2 true JPS6150940B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-11-06 |
Family
ID=22730015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56163544A Granted JPS57158753A (en) | 1980-10-16 | 1981-10-15 | Novel bicyclooxyphenylurea |
Country Status (4)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20060003055A (ko) * | 2003-04-30 | 2006-01-09 | 에프엠씨 코포레이션 | 살충성 (다이할로프로펜일)페닐알킬 치환된다이하이드로벤조퓨란 및 다이하이드로벤조피란 유도체 |
-
1981
- 1981-10-14 ZA ZA817110A patent/ZA817110B/xx unknown
- 1981-10-15 JP JP56163544A patent/JPS57158753A/ja active Granted
- 1981-10-16 MW MW4481A patent/MW4481A1/xx unknown
- 1981-10-16 ZM ZM8781A patent/ZM8781A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MW4481A1 (en) | 1983-02-09 |
| ZA817110B (en) | 1982-09-29 |
| ZM8781A1 (en) | 1983-02-21 |
| JPS57158753A (en) | 1982-09-30 |
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