OA11130A - Fungicidal compositions based on (N-phenylacetyl-N-2,6-xylyl)methal alaninate - Google Patents
Fungicidal compositions based on (N-phenylacetyl-N-2,6-xylyl)methal alaninate Download PDFInfo
- Publication number
- OA11130A OA11130A OA9900132A OA9900132A OA11130A OA 11130 A OA11130 A OA 11130A OA 9900132 A OA9900132 A OA 9900132A OA 9900132 A OA9900132 A OA 9900132A OA 11130 A OA11130 A OA 11130A
- Authority
- OA
- OAPI
- Prior art keywords
- group
- methyl
- formula
- fungicidal compositions
- compositions according
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 74
- 230000000855 fungicidal effect Effects 0.000 title claims description 70
- QNAYBMKLOCPYGJ-UHFFFAOYSA-M alaninate Chemical compound CC(N)C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-M 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims description 109
- 230000000875 corresponding effect Effects 0.000 claims description 58
- -1 ( 4 - methoxyphenyl)-ethyl Chemical group 0.000 claims description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 35
- 239000000417 fungicide Substances 0.000 claims description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 150000007529 inorganic bases Chemical class 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 239000005802 Mancozeb Substances 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 150000007530 organic bases Chemical class 0.000 claims description 10
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 208000015181 infectious disease Diseases 0.000 claims description 8
- DWKPPFQULDPWHX-VKHMYHEASA-N l-alanyl ester Chemical compound COC(=O)[C@H](C)N DWKPPFQULDPWHX-VKHMYHEASA-N 0.000 claims description 8
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 8
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 claims description 7
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 claims description 7
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 7
- 239000005761 Dimethomorph Substances 0.000 claims description 7
- XFOXDUJCOHBXRC-UHFFFAOYSA-N N-Ethyl-N-methyl-4-(trifluoromethyl)-2-(3,4-dimethoxyphenyl)benzamide Chemical compound CCN(C)C(=O)C1=CC=C(C(F)(F)F)C=C1C1=CC=C(OC)C(OC)=C1 XFOXDUJCOHBXRC-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 150000004702 methyl esters Chemical class 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 239000005790 Fosetyl Substances 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 239000003849 aromatic solvent Substances 0.000 claims description 5
- 230000001276 controlling effect Effects 0.000 claims description 5
- 230000007613 environmental effect Effects 0.000 claims description 5
- VUERQRKTYBIULR-UHFFFAOYSA-N fosetyl Chemical compound CCOP(O)=O VUERQRKTYBIULR-UHFFFAOYSA-N 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical group CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 claims description 5
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000005747 Chlorothalonil Substances 0.000 claims description 4
- 239000005772 Famoxadone Substances 0.000 claims description 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005821 Propamocarb Substances 0.000 claims description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 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 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 244000052769 pathogen Species 0.000 claims description 4
- 229960003424 phenylacetic acid Drugs 0.000 claims description 4
- 239000003279 phenylacetic acid Substances 0.000 claims description 4
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 claims description 3
- SACFASUHQGNXOD-UHFFFAOYSA-N 4,6-dichloro-n-phenyl-1,3,5-triazin-2-amine Chemical compound ClC1=NC(Cl)=NC(NC=2C=CC=CC=2)=N1 SACFASUHQGNXOD-UHFFFAOYSA-N 0.000 claims description 3
- 239000005756 Cymoxanil Substances 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001263 acyl chlorides Chemical class 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 3
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 claims description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 claims description 2
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 239000005745 Captan Substances 0.000 claims description 2
- 239000005758 Cyprodinil Substances 0.000 claims description 2
- 239000005764 Dithianon Substances 0.000 claims description 2
- 239000005769 Etridiazole Substances 0.000 claims description 2
- 239000005780 Fluazinam Substances 0.000 claims description 2
- 239000005805 Mepanipyrim Substances 0.000 claims description 2
- 239000005807 Metalaxyl Substances 0.000 claims description 2
- 239000005814 Pencycuron Substances 0.000 claims description 2
- 239000005822 Propiconazole Substances 0.000 claims description 2
- 239000005823 Propineb Substances 0.000 claims description 2
- 239000005840 Tetraconazole Substances 0.000 claims description 2
- 239000005843 Thiram Chemical group 0.000 claims description 2
- 239000005846 Triadimenol Substances 0.000 claims description 2
- 125000006193 alkinyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 229940117949 captan Drugs 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 claims description 2
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 claims description 2
- PYZSVQVRHDXQSL-UHFFFAOYSA-N dithianon Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O PYZSVQVRHDXQSL-UHFFFAOYSA-N 0.000 claims description 2
- 239000012990 dithiocarbamate Substances 0.000 claims description 2
- 150000004659 dithiocarbamates Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- KQTVWCSONPJJPE-UHFFFAOYSA-N etridiazole Chemical compound CCOC1=NC(C(Cl)(Cl)Cl)=NS1 KQTVWCSONPJJPE-UHFFFAOYSA-N 0.000 claims description 2
- 239000003337 fertilizer Substances 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 239000004009 herbicide Substances 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 claims description 2
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 claims description 2
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 claims description 2
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 2
- 229960002447 thiram Drugs 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 2
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 claims description 2
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- 229910052725 zinc Chemical group 0.000 claims description 2
- 239000011701 zinc Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 claims 1
- 229950002475 mesilate Drugs 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000000575 pesticide Substances 0.000 description 20
- 230000004224 protection Effects 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000005734 Benalaxyl Substances 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 239000000243 solution Substances 0.000 description 9
- 230000002195 synergetic effect Effects 0.000 description 9
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 241000227653 Lycopersicon Species 0.000 description 5
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
- 241001281803 Plasmopara viticola Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229940073584 methylene chloride Drugs 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
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- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 210000000051 wattle Anatomy 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- 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
- A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT96MI002660 IT1290855B1 (it) | 1996-12-19 | 1996-12-19 | Composizioni fungicide a base di (n-fenilacetil-n-2,6-xilil)-alaninato di metile |
| IT97MI001198 IT1291373B1 (it) | 1997-05-22 | 1997-05-22 | Composizioni fungicide a base di (n-fenilacetil-n-2,6-xilil)- alaninato di metile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA11130A true OA11130A (en) | 2003-04-28 |
Family
ID=26331455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA9900132A OA11130A (en) | 1996-12-19 | 1999-06-18 | Fungicidal compositions based on (N-phenylacetyl-N-2,6-xylyl)methal alaninate |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6228885B1 (pl) |
| EP (2) | EP0946093B1 (pl) |
| CN (1) | CN1225972C (pl) |
| AU (1) | AU5756798A (pl) |
| BR (1) | BR9714423B1 (pl) |
| CU (1) | CU22888A3 (pl) |
| DE (2) | DE69715038T2 (pl) |
| ES (2) | ES2190425T3 (pl) |
| HK (1) | HK1043710B (pl) |
| HU (2) | HU227487B1 (pl) |
| IL (1) | IL130534A (pl) |
| OA (1) | OA11130A (pl) |
| PL (1) | PL189827B1 (pl) |
| PT (1) | PT946093E (pl) |
| WO (1) | WO1998026654A2 (pl) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6679922B1 (en) * | 1998-06-22 | 2004-01-20 | The Regents Of The University Of California | Pesticide protective articles |
| IT1303800B1 (it) * | 1998-11-30 | 2001-02-23 | Isagro Ricerca Srl | Composti dipeptidici aventi elevata attivita' fungicida e loroutilizzo agronomico. |
| EP1159273A1 (en) | 1999-03-02 | 2001-12-05 | Boehringer Ingelheim Pharmaceuticals Inc. | Compounds useful as reversible inhibitors of cathepsin s |
| ITMI991330A1 (it) * | 1999-06-15 | 2000-12-15 | Isagro Spa | Processo per la preparazione di fungicidi otticamente attivi costituiti da n-acil derivati del metil n-(2,6-dimetilfenil)-d-alaninato |
| US6420364B1 (en) | 1999-09-13 | 2002-07-16 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compound useful as reversible inhibitors of cysteine proteases |
| CN1283152C (zh) * | 2002-07-18 | 2006-11-08 | 巴斯福股份公司 | 杀真菌混合物 |
| KR20080000665A (ko) * | 2005-04-22 | 2008-01-02 | 알란토스 파마슈티컬즈 홀딩, 인코포레이티드 | 디펩티딜 펩티다아제-ⅳ 억제제 |
| ITMI20051558A1 (it) | 2005-08-09 | 2007-02-10 | Isagro Spa | Miscele e-o composizioni sinergiche cin elevata attivita'fungicida |
| WO2007031283A2 (de) | 2005-09-13 | 2007-03-22 | Basf Se | Verfahren zum schutz vor phytopathogenen mit kiralaxyl, entsprechende verwendung und mittel hierzu |
| KR20080070676A (ko) * | 2005-11-22 | 2008-07-30 | 이시하라 산교 가부시끼가이샤 | 농원예용 살균제 조성물 및 식물 병해의 방제 방법 |
| ITMI20052459A1 (it) | 2005-12-22 | 2007-06-23 | Isagro Spa | Sali quaternari e relativo uso per il controllo di fitopatogeni |
| CN1321567C (zh) * | 2005-12-30 | 2007-06-20 | 湖南万家丰科技有限公司 | 一种用于农作物的杀菌组合物 |
| US20070232693A1 (en) * | 2006-03-28 | 2007-10-04 | Novus International, Inc. | Compositions for treating infestation of plants by phytopathogenic microorganisms |
| US20110098177A1 (en) * | 2006-03-28 | 2011-04-28 | Novus International Inc. | Methods and compositions of plant micronutrients |
| EP2000028A1 (de) * | 2007-06-06 | 2008-12-10 | Bayer CropScience Aktiengesellschaft | Fungizide Wirkstoffkombinationen |
| CN102578130B (zh) * | 2007-10-09 | 2013-04-17 | 中国中化股份有限公司 | 一种杀真菌组合物 |
| MX2009002351A (es) * | 2008-03-07 | 2009-09-25 | Plant Protectants Llc | Metodos para proteger cultivos de la descomposicion microbiana de post cosecha. |
| US20090269517A1 (en) * | 2008-04-29 | 2009-10-29 | Kenneth Alan Karmie | Floor cleansing system and method for use thereof |
| US20100047412A1 (en) * | 2008-08-20 | 2010-02-25 | Plant Protectants, Llc | Post Harvest Treatment of Fruit |
| WO2010092014A2 (en) * | 2009-02-11 | 2010-08-19 | Basf Se | Pesticidal mixtures |
| US9675080B2 (en) | 2009-03-20 | 2017-06-13 | Verdesian Life Sciences U.S., Llc | Methods for delaying maturity of crops |
| AR076224A1 (es) | 2009-04-22 | 2011-05-26 | Bayer Cropscience Ag | Uso de propineb como repelente de aves |
| CN101632383B (zh) * | 2009-05-27 | 2012-12-12 | 深圳诺普信农化股份有限公司 | 一种农药组合物及其应用 |
| PT106351B (pt) | 2012-06-01 | 2014-05-21 | Sapec Agro S A | Mistura fungicida sinérgica contendo dimetomorfe e propamocarbe-hidrocloreto |
| CN105379723B (zh) * | 2015-11-06 | 2018-02-16 | 南京华洲药业有限公司 | 一种含嘧菌胺和苯霜灵的杀菌组合物及其应用 |
| WO2023277590A1 (ko) * | 2021-06-29 | 2023-01-05 | 주식회사 엘지화학 | 알킬-d-알라니네이트의 제조방법, 알킬-d-알라니네이트, 알킬-d-알라니네이트 유도체, 및 이를 포함하는 의약품 또는 농업용품 |
| WO2023277587A1 (ko) * | 2021-06-29 | 2023-01-05 | 주식회사 엘지화학 | N-아실 유도체의 제조방법, 조성물 및 이를 포함하는 의약품 또는 농업용품 |
| CN115413672A (zh) * | 2022-09-09 | 2022-12-02 | 陕西美邦药业集团股份有限公司 | 一种用于治疗葡萄霜霉病的增效组合物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH687169A5 (de) * | 1994-07-11 | 1996-10-15 | Ciba Geigy Ag | Mikrobizide. |
| US5723491A (en) * | 1994-07-11 | 1998-03-03 | Novartis Corporation | Fungicidal composition and method of controlling fungus infestation |
-
1997
- 1997-12-06 CN CNB971814295A patent/CN1225972C/zh not_active Expired - Lifetime
- 1997-12-06 IL IL130534A patent/IL130534A/en not_active IP Right Cessation
- 1997-12-06 ES ES01203103T patent/ES2190425T3/es not_active Expired - Lifetime
- 1997-12-06 BR BRPI9714423-1A patent/BR9714423B1/pt not_active IP Right Cessation
- 1997-12-06 US US09/331,168 patent/US6228885B1/en not_active Expired - Lifetime
- 1997-12-06 DE DE69715038T patent/DE69715038T2/de not_active Expired - Lifetime
- 1997-12-06 WO PCT/EP1997/006968 patent/WO1998026654A2/en not_active Ceased
- 1997-12-06 CU CU1999077A patent/CU22888A3/es unknown
- 1997-12-06 PL PL97334184A patent/PL189827B1/pl unknown
- 1997-12-06 EP EP97953792A patent/EP0946093B1/en not_active Expired - Lifetime
- 1997-12-06 EP EP01203103A patent/EP1155616B1/en not_active Expired - Lifetime
- 1997-12-06 DE DE69718835T patent/DE69718835T2/de not_active Expired - Lifetime
- 1997-12-06 PT PT97953792T patent/PT946093E/pt unknown
- 1997-12-06 HU HU0000480A patent/HU227487B1/hu active Protection Beyond IP Right Term
- 1997-12-06 ES ES97953792T patent/ES2182147T3/es not_active Expired - Lifetime
- 1997-12-06 AU AU57567/98A patent/AU5756798A/en not_active Abandoned
-
1999
- 1999-06-18 OA OA9900132A patent/OA11130A/en unknown
-
2002
- 2002-05-21 HK HK02103821.7A patent/HK1043710B/en not_active IP Right Cessation
-
2011
- 2011-12-02 HU HUS1100025C patent/HUS1100025I1/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR9714423B1 (pt) | 2012-03-20 |
| HK1024385A1 (en) | 2000-10-13 |
| HK1043710B (en) | 2003-06-20 |
| DE69718835T2 (de) | 2003-12-24 |
| EP1155616B1 (en) | 2003-01-29 |
| HUS1100025I1 (hu) | 2016-10-28 |
| DE69715038T2 (de) | 2003-03-13 |
| WO1998026654A3 (en) | 1998-10-22 |
| EP0946093A2 (en) | 1999-10-06 |
| HU227487B1 (en) | 2011-07-28 |
| CU22888A3 (es) | 2004-01-23 |
| BR9714423A (pt) | 2000-07-04 |
| PL189827B1 (pl) | 2005-09-30 |
| HUP0000480A3 (en) | 2001-02-28 |
| ES2182147T3 (es) | 2003-03-01 |
| IL130534A0 (en) | 2000-06-01 |
| EP1155616A1 (en) | 2001-11-21 |
| AU5756798A (en) | 1998-07-15 |
| HK1043710A1 (en) | 2002-09-27 |
| US6228885B1 (en) | 2001-05-08 |
| HUP0000480A2 (hu) | 2000-06-28 |
| CN1244770A (zh) | 2000-02-16 |
| DE69715038D1 (de) | 2002-10-02 |
| IL130534A (en) | 2006-09-05 |
| PT946093E (pt) | 2002-12-31 |
| DE69718835D1 (de) | 2003-03-06 |
| WO1998026654A2 (en) | 1998-06-25 |
| PL334184A1 (en) | 2000-02-14 |
| ES2190425T3 (es) | 2003-08-01 |
| CN1225972C (zh) | 2005-11-09 |
| EP0946093B1 (en) | 2002-08-28 |
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