IL120970A - Acetonylbenzamides, or nicotinamides, their preparations and fungicides containing them - Google Patents
Acetonylbenzamides, or nicotinamides, their preparations and fungicides containing themInfo
- Publication number
- IL120970A IL120970A IL12097097A IL12097097A IL120970A IL 120970 A IL120970 A IL 120970A IL 12097097 A IL12097097 A IL 12097097A IL 12097097 A IL12097097 A IL 12097097A IL 120970 A IL120970 A IL 120970A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- halo
- alkenyl
- alkynyl
- independently selected
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 20
- 239000000203 mixture Substances 0.000 title claims description 59
- 238000002360 preparation method Methods 0.000 title description 17
- ZTONKKHCXJTROW-UHFFFAOYSA-N n-(2-oxopropyl)benzamide Chemical class CC(=O)CNC(=O)C1=CC=CC=C1 ZTONKKHCXJTROW-UHFFFAOYSA-N 0.000 title description 5
- 235000005152 nicotinamide Nutrition 0.000 title description 4
- 150000005480 nicotinamides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 28
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- -1 halo (C1-C6) alkyl Chemical group 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 125000005843 halogen group Chemical group 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- KCOPAESEGCGTKM-UHFFFAOYSA-N 1,3-oxazol-4-one Chemical compound O=C1COC=N1 KCOPAESEGCGTKM-UHFFFAOYSA-N 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 238000007142 ring opening reaction Methods 0.000 claims description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- 150000001263 acyl chlorides Chemical class 0.000 claims description 2
- 150000002148 esters Chemical group 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000001963 growth medium Substances 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 239000000575 pesticide Substances 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 230000035040 seed growth Effects 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000417 fungicide Substances 0.000 description 13
- 201000010099 disease Diseases 0.000 description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 241000227653 Lycopersicon Species 0.000 description 5
- 241000219095 Vitis Species 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- GCHPUFAZSONQIV-UHFFFAOYSA-N isovaline Chemical compound CCC(C)(N)C(O)=O GCHPUFAZSONQIV-UHFFFAOYSA-N 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- VANLOTTWWVKJHY-SSDOTTSWSA-N (2r)-2-[(2-chloroacetyl)amino]-2-methylbutanoic acid Chemical compound CC[C@](C)(C(O)=O)NC(=O)CCl VANLOTTWWVKJHY-SSDOTTSWSA-N 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 235000009754 Vitis X bourquina Nutrition 0.000 description 4
- 235000012333 Vitis X labruscana Nutrition 0.000 description 4
- 235000014787 Vitis vinifera Nutrition 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- HVPPPARGXDTDEY-RGMNGODLSA-N methyl (2s)-2-amino-2-methylbutanoate;hydrochloride Chemical compound Cl.CC[C@](C)(N)C(=O)OC HVPPPARGXDTDEY-RGMNGODLSA-N 0.000 description 4
- 239000001965 potato dextrose agar Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 241000123650 Botrytis cinerea Species 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000918584 Pythium ultimum Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- GCHPUFAZSONQIV-RXMQYKEDSA-N d-isovaline Chemical compound CC[C@@](C)(N)C(O)=O GCHPUFAZSONQIV-RXMQYKEDSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- LYSVZYUJIMIKEB-LURJTMIESA-N methyl (2s)-2-amino-2-methylbutanoate Chemical compound CC[C@](C)(N)C(=O)OC LYSVZYUJIMIKEB-LURJTMIESA-N 0.000 description 3
- 230000003032 phytopathogenic effect Effects 0.000 description 3
- CYBOBNODYVJFNM-JEDNCBNOSA-N (2s)-2-amino-2-methylbutanoic acid;hydrochloride Chemical compound Cl.CC[C@](C)(N)C(O)=O CYBOBNODYVJFNM-JEDNCBNOSA-N 0.000 description 2
- SOUGWDPPRBKJEX-AWEZNQCLSA-N (S)-zoxamide Chemical compound ClCC(=O)[C@](C)(CC)NC(=O)C1=CC(Cl)=C(C)C(Cl)=C1 SOUGWDPPRBKJEX-AWEZNQCLSA-N 0.000 description 2
- VANLOTTWWVKJHY-UHFFFAOYSA-N 2-[(2-chloroacetyl)amino]-2-methylbutanoic acid Chemical compound CCC(C)(C(O)=O)NC(=O)CCl VANLOTTWWVKJHY-UHFFFAOYSA-N 0.000 description 2
- UKKKGCZFKPKTPL-AWEZNQCLSA-N 3,5-dichloro-4-methyl-n-[(3s)-3-methyl-2-oxopentan-3-yl]benzamide Chemical compound CC[C@@](C)(C(C)=O)NC(=O)C1=CC(Cl)=C(C)C(Cl)=C1 UKKKGCZFKPKTPL-AWEZNQCLSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000005156 Dehydration Diseases 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000233679 Peronosporaceae Species 0.000 description 2
- 241000233622 Phytophthora infestans Species 0.000 description 2
- 241001281803 Plasmopara viticola Species 0.000 description 2
- 241000233639 Pythium Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
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- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- HVPPPARGXDTDEY-FYZOBXCZSA-N methyl (2r)-2-amino-2-methylbutanoate;hydrochloride Chemical compound Cl.CC[C@@](C)(N)C(=O)OC HVPPPARGXDTDEY-FYZOBXCZSA-N 0.000 description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
- 229960003966 nicotinamide Drugs 0.000 description 2
- 239000011570 nicotinamide Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000007164 v-8 juice agar Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- GCHPUFAZSONQIV-YFKPBYRVSA-N (2s)-2-azaniumyl-2-methylbutanoate Chemical compound CC[C@](C)([NH3+])C([O-])=O GCHPUFAZSONQIV-YFKPBYRVSA-N 0.000 description 1
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 1
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 1
- HZJKXKUJVSEEFU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 HZJKXKUJVSEEFU-UHFFFAOYSA-N 0.000 description 1
- OWDLFBLNMPCXSD-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)C1C(=O)OCC1 OWDLFBLNMPCXSD-UHFFFAOYSA-N 0.000 description 1
- LQAQMOIBXDELJX-UHFFFAOYSA-N 2-methoxyprop-2-enoic acid Chemical class COC(=C)C(O)=O LQAQMOIBXDELJX-UHFFFAOYSA-N 0.000 description 1
- XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 description 1
- GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical class NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-UHFFFAOYSA-N 0.000 description 1
- UNONPWRUIRVAIG-UHFFFAOYSA-N 3,5-dichloro-4-methylbenzoyl chloride Chemical compound CC1=C(Cl)C=C(C(Cl)=O)C=C1Cl UNONPWRUIRVAIG-UHFFFAOYSA-N 0.000 description 1
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 description 1
- VSJRBQDMBFFHMC-UHFFFAOYSA-N 5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound CCC1(C)NC(=O)NC1=O VSJRBQDMBFFHMC-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 101100020619 Arabidopsis thaliana LATE gene Proteins 0.000 description 1
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- 239000005734 Benalaxyl Substances 0.000 description 1
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- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 102000011045 Chloride Channels Human genes 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- KRZUZYJEQBXUIN-UHFFFAOYSA-N Cyprofuram Chemical compound ClC1=CC=CC(N(C2C(OCC2)=O)C(=O)C2CC2)=C1 KRZUZYJEQBXUIN-UHFFFAOYSA-N 0.000 description 1
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- 238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 description 1
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- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
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- FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
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- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052806 inorganic carbonate Inorganic materials 0.000 description 1
- 229910052909 inorganic silicate Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- LYSVZYUJIMIKEB-ZCFIWIBFSA-N methyl (2r)-2-amino-2-methylbutanoate Chemical compound CC[C@@](C)(N)C(=O)OC LYSVZYUJIMIKEB-ZCFIWIBFSA-N 0.000 description 1
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 1
- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 230000000063 preceeding effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 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
- 238000003892 spreading Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003679 valine derivatives Chemical class 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/76—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL13593897A IL135938A (en) | 1996-06-28 | 1997-06-02 | Process for preparing a racemic mixture of n-acetonylbenzamides or nicotinamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2051696P | 1996-06-28 | 1996-06-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL120970A0 IL120970A0 (en) | 1997-11-20 |
| IL120970A true IL120970A (en) | 2001-05-20 |
Family
ID=21799041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12097097A IL120970A (en) | 1996-06-28 | 1997-06-02 | Acetonylbenzamides, or nicotinamides, their preparations and fungicides containing them |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0816330B1 (cs) |
| JP (1) | JP4236712B2 (cs) |
| KR (1) | KR100473534B1 (cs) |
| CN (1) | CN1089549C (cs) |
| AR (1) | AR007419A1 (cs) |
| AT (1) | ATE198318T1 (cs) |
| AU (1) | AU2488997A (cs) |
| BR (1) | BR9703757A (cs) |
| CA (1) | CA2207865A1 (cs) |
| CO (1) | CO4790129A1 (cs) |
| CZ (1) | CZ205197A3 (cs) |
| DE (1) | DE69703764T2 (cs) |
| HU (1) | HUP9701115A3 (cs) |
| ID (1) | ID17574A (cs) |
| IL (1) | IL120970A (cs) |
| PL (1) | PL320821A1 (cs) |
| SK (1) | SK87497A3 (cs) |
| TR (1) | TR199700547A3 (cs) |
| TW (1) | TW327598B (cs) |
| ZA (1) | ZA974950B (cs) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4143700A (en) * | 1999-04-28 | 2000-11-17 | Ihara Chemical Industry Co. Ltd. | Process for the preparation of amides |
| JP2000319241A (ja) * | 1999-04-28 | 2000-11-21 | Ihara Chem Ind Co Ltd | フェニルアルカン酸アミド化合物の製造方法 |
| JP4799744B2 (ja) * | 2000-02-16 | 2011-10-26 | 石原産業株式会社 | フェナシルアミン誘導体、それらの製造方法及びそれらを含有する有害生物防除剤 |
| EP1256569B1 (en) | 2000-02-16 | 2010-07-07 | Ishihara Sangyo Kaisha, Ltd. | Phenacylamine derivatives, production thereof and pest controllers containing the derivatives |
| WO2003027059A1 (en) * | 2001-09-18 | 2003-04-03 | Ishihara Sangyo Kaisha, Ltd. | Acid amide derivatives, process for producing these, and pest control agent containing these |
| US7375093B2 (en) | 2002-07-05 | 2008-05-20 | Intrexon Corporation | Ketone ligands for modulating the expression of exogenous genes via an ecdysone receptor complex |
| CN104513175A (zh) * | 2013-09-30 | 2015-04-15 | 华东师范大学 | 一种光学活性α-氨基酸酯衍生物的制备方法 |
| ES2735924T3 (es) | 2015-04-17 | 2019-12-20 | Dow Agrosciences Llc | Moléculas que tienen utilidad plaguicida e intermediarios, composiciones y procesos, relacionados con ellas |
| CN109810016B (zh) * | 2019-02-25 | 2021-11-23 | 大连凯飞化学股份有限公司 | 一种对映体混合物及其制备方法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4822902A (en) * | 1984-07-26 | 1989-04-18 | Rohm And Haas Company | N-acetonylbenzamides and their use as fungicides |
| US4863940A (en) * | 1984-07-26 | 1989-09-05 | Rohm And Haas | N-acetonyl-substituted amides and phytopathogenic fungicidal use thereof |
| US5304572A (en) * | 1992-12-01 | 1994-04-19 | Rohm And Haas Company | N-acetonylbenzamides and their use as fungicides |
| US5254584A (en) * | 1992-12-18 | 1993-10-19 | Rohm And Haas Company | N-acetonylbenzamides and their use as fungicides |
-
1997
- 1997-06-02 IL IL12097097A patent/IL120970A/en not_active IP Right Cessation
- 1997-06-05 ZA ZA9704950A patent/ZA974950B/xx unknown
- 1997-06-16 AU AU24889/97A patent/AU2488997A/en not_active Abandoned
- 1997-06-16 DE DE69703764T patent/DE69703764T2/de not_active Expired - Fee Related
- 1997-06-16 AT AT97304190T patent/ATE198318T1/de not_active IP Right Cessation
- 1997-06-16 EP EP97304190A patent/EP0816330B1/en not_active Expired - Lifetime
- 1997-06-17 CA CA002207865A patent/CA2207865A1/en not_active Abandoned
- 1997-06-18 AR ARP970102680A patent/AR007419A1/es unknown
- 1997-06-26 CO CO97035747A patent/CO4790129A1/es unknown
- 1997-06-26 ID IDP972198A patent/ID17574A/id unknown
- 1997-06-26 CN CN97111861A patent/CN1089549C/zh not_active Expired - Fee Related
- 1997-06-27 BR BR9703757A patent/BR9703757A/pt not_active IP Right Cessation
- 1997-06-27 TR TR97/00547A patent/TR199700547A3/tr unknown
- 1997-06-27 HU HU9701115A patent/HUP9701115A3/hu unknown
- 1997-06-27 PL PL97320821A patent/PL320821A1/xx unknown
- 1997-06-27 KR KR1019970028323A patent/KR100473534B1/ko not_active Expired - Fee Related
- 1997-06-27 SK SK874-97A patent/SK87497A3/sk unknown
- 1997-06-27 CZ CZ972051A patent/CZ205197A3/cs unknown
- 1997-06-30 JP JP18724697A patent/JP4236712B2/ja not_active Expired - Fee Related
- 1997-07-01 TW TW086109244A patent/TW327598B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2207865A1 (en) | 1997-12-28 |
| SK87497A3 (en) | 1998-01-14 |
| JPH1143472A (ja) | 1999-02-16 |
| HU9701115D0 (en) | 1997-08-28 |
| HUP9701115A3 (en) | 1998-08-28 |
| JP4236712B2 (ja) | 2009-03-11 |
| KR980002023A (ko) | 1998-03-30 |
| BR9703757A (pt) | 1998-11-10 |
| TR199700547A2 (xx) | 1998-01-21 |
| IL120970A0 (en) | 1997-11-20 |
| ZA974950B (en) | 1997-12-29 |
| CN1089549C (zh) | 2002-08-28 |
| EP0816330A1 (en) | 1998-01-07 |
| AU2488997A (en) | 1998-01-15 |
| HUP9701115A2 (hu) | 1998-03-30 |
| EP0816330B1 (en) | 2000-12-27 |
| PL320821A1 (en) | 1998-01-05 |
| DE69703764D1 (de) | 2001-02-01 |
| ID17574A (id) | 1998-01-08 |
| AR007419A1 (es) | 1999-10-27 |
| DE69703764T2 (de) | 2001-05-23 |
| CN1173278A (zh) | 1998-02-18 |
| TW327598B (en) | 1998-03-01 |
| ATE198318T1 (de) | 2001-01-15 |
| KR100473534B1 (ko) | 2006-05-02 |
| CO4790129A1 (es) | 1999-05-31 |
| CZ205197A3 (cs) | 1998-01-14 |
| TR199700547A3 (tr) | 1998-01-21 |
| MX9704839A (es) | 1998-07-31 |
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| Date | Code | Title | Description |
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| FF | Patent granted | ||
| KB | Patent renewed | ||
| HP | Change in proprietorship | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |