CA2474354A1 - Phenylalanine derivatives as herbicides - Google Patents
Phenylalanine derivatives as herbicides Download PDFInfo
- Publication number
- CA2474354A1 CA2474354A1 CA002474354A CA2474354A CA2474354A1 CA 2474354 A1 CA2474354 A1 CA 2474354A1 CA 002474354 A CA002474354 A CA 002474354A CA 2474354 A CA2474354 A CA 2474354A CA 2474354 A1 CA2474354 A1 CA 2474354A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- alkoxy
- hydrogen
- formula
- compounds
- 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.)
- Abandoned
Links
- 150000002993 phenylalanine derivatives Chemical class 0.000 title claims abstract description 53
- 239000004009 herbicide Substances 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 340
- 230000008635 plant growth Effects 0.000 claims abstract description 14
- 230000001105 regulatory effect Effects 0.000 claims abstract description 12
- -1 C2-C6-haloalkynyl Chemical group 0.000 claims description 354
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 328
- 239000000460 chlorine Substances 0.000 claims description 267
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 168
- 229910052739 hydrogen Inorganic materials 0.000 claims description 144
- 239000001257 hydrogen Substances 0.000 claims description 140
- 125000001424 substituent group Chemical group 0.000 claims description 102
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 96
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 84
- 150000002367 halogens Chemical class 0.000 claims description 77
- 229910052736 halogen Inorganic materials 0.000 claims description 73
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 71
- 239000000203 mixture Substances 0.000 claims description 62
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 56
- 229910052731 fluorine Inorganic materials 0.000 claims description 49
- 239000011737 fluorine Substances 0.000 claims description 49
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 44
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 43
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 42
- 229910052801 chlorine Inorganic materials 0.000 claims description 42
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 31
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 31
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 30
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 30
- 229920005989 resin Polymers 0.000 claims description 30
- 239000011347 resin Substances 0.000 claims description 30
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 29
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 20
- 239000003960 organic solvent Substances 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- 125000006239 protecting group Chemical group 0.000 claims description 18
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 17
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 12
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 229910052757 nitrogen Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 230000001276 controlling effect Effects 0.000 claims description 6
- 150000005690 diesters Chemical class 0.000 claims description 5
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004970 halomethyl group Chemical group 0.000 claims description 4
- 239000002952 polymeric resin Substances 0.000 claims description 4
- 229920003002 synthetic resin Polymers 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 30
- 238000004519 manufacturing process Methods 0.000 claims 6
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 22
- 229910052794 bromium Inorganic materials 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 230000012010 growth Effects 0.000 description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 13
- 240000006995 Abutilon theophrasti Species 0.000 description 13
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 13
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- 238000012360 testing method Methods 0.000 description 12
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- 230000006181 N-acylation Effects 0.000 description 11
- 230000002363 herbicidal effect Effects 0.000 description 11
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
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- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 9
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 9
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- 238000002360 preparation method Methods 0.000 description 9
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- 239000013543 active substance Substances 0.000 description 8
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 8
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- LBRKWOMVQVHPGL-UHFFFAOYSA-N methyl 4,6-dichloro-6-(difluoromethyl)cyclohexa-2,4-diene-1-carboxylate Chemical compound COC(=O)C1C=CC(Cl)=CC1(Cl)C(F)F LBRKWOMVQVHPGL-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QSRAHRDVKZPGGE-UHFFFAOYSA-N n-(2,6-dimethyl-4-phenylmethoxyphenyl)-2-pyrrolidin-1-ylacetamide Chemical compound C=1C(C)=C(NC(=O)CN2CCCC2)C(C)=CC=1OCC1=CC=CC=C1 QSRAHRDVKZPGGE-UHFFFAOYSA-N 0.000 description 1
- RJUPHOSGURUYLR-UHFFFAOYSA-N n-[2,6-dimethyl-4-(2-phenylethoxy)phenyl]-2-pyrrolidin-1-ylacetamide Chemical compound C=1C(C)=C(NC(=O)CN2CCCC2)C(C)=CC=1OCCC1=CC=CC=C1 RJUPHOSGURUYLR-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WNPVAXLJVUXYFU-UHFFFAOYSA-N n-cyclohex-2-en-1-ylidenehydroxylamine Chemical compound ON=C1CCCC=C1 WNPVAXLJVUXYFU-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000002412 n-penten-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002504 n-penten-4-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 235000002252 panizo Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 150000008048 phenylpyrazoles Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 235000021039 pomes Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000013138 pruning Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- 235000013526 red clover Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
- 101150050926 sla1 gene Proteins 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 230000036435 stunted growth Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- IRYJRGCIQBGHIV-UHFFFAOYSA-N trimethadione Chemical compound CN1C(=O)OC(C)(C)C1=O IRYJRGCIQBGHIV-UHFFFAOYSA-N 0.000 description 1
- 150000003667 tyrosine derivatives Chemical class 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10204951A DE10204951A1 (de) | 2002-02-06 | 2002-02-06 | Phenylalaninderivate als Herbizide |
| DE10204951.3 | 2002-02-06 | ||
| PCT/EP2003/000926 WO2003066576A1 (de) | 2002-02-06 | 2003-01-30 | Phenylalaninderivate als herbizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2474354A1 true CA2474354A1 (en) | 2003-08-14 |
Family
ID=27588444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002474354A Abandoned CA2474354A1 (en) | 2002-02-06 | 2003-01-30 | Phenylalanine derivatives as herbicides |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20050215435A1 (enExample) |
| EP (1) | EP1474381B1 (enExample) |
| JP (1) | JP4713833B2 (enExample) |
| AT (1) | ATE305448T1 (enExample) |
| AU (1) | AU2003205712A1 (enExample) |
| CA (1) | CA2474354A1 (enExample) |
| DE (2) | DE10204951A1 (enExample) |
| WO (1) | WO2003066576A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7687435B2 (en) | 2003-12-19 | 2010-03-30 | Basf Aktiengesellschaft | Benzoyl-substituted phenylalanineamides |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1716120A1 (de) * | 2003-12-19 | 2006-11-02 | Basf Aktiengesellschaft | Herbizide heteroaroyl-substituierte phenylalanin-amide |
| CN101023069A (zh) * | 2004-09-16 | 2007-08-22 | 巴斯福股份公司 | 苯甲酰基取代的丝氨酸酰胺 |
| CA2577181A1 (en) * | 2004-09-16 | 2006-03-23 | Basf Aktiengesellschaft | Heteroaroyl-substituted serine amides utilized as herbicides |
| CN101228133A (zh) * | 2005-05-25 | 2008-07-23 | 巴斯福股份公司 | 杂芳酰基取代的丝氨酸酰胺 |
| US7786046B2 (en) * | 2005-05-25 | 2010-08-31 | Basf Aktiengesellschaft | Benzoyl-substituted serineamides |
| RU2394560C2 (ru) | 2005-07-19 | 2010-07-20 | Дайити Санкио Компани, Лимитед | Замещенное пропанамидное производное и фармацевтическая композиция, содержащая такое производное |
| US8097712B2 (en) | 2007-11-07 | 2012-01-17 | Beelogics Inc. | Compositions for conferring tolerance to viral disease in social insects, and the use thereof |
| US20110318470A1 (en) * | 2008-10-31 | 2011-12-29 | Klaus Grossmann | Method For Improving Plant Health |
| RU2011121521A (ru) * | 2008-10-31 | 2012-12-10 | Басф Се | Способ улучшения жизнеспособности растения |
| US8962584B2 (en) | 2009-10-14 | 2015-02-24 | Yissum Research Development Company Of The Hebrew University Of Jerusalem, Ltd. | Compositions for controlling Varroa mites in bees |
| CN102822350B (zh) | 2010-03-08 | 2015-05-06 | 孟山都技术公司 | 用于植物基因调控的多核苷酸分子 |
| AR085467A1 (es) | 2011-03-23 | 2013-10-02 | Syngenta Participations Ag | Metodos y composiciones para un mayor rendimiento de las plantas |
| US10829828B2 (en) | 2011-09-13 | 2020-11-10 | Monsanto Technology Llc | Methods and compositions for weed control |
| WO2013040033A1 (en) | 2011-09-13 | 2013-03-21 | Monsanto Technology Llc | Methods and compositions for weed control |
| US10806146B2 (en) | 2011-09-13 | 2020-10-20 | Monsanto Technology Llc | Methods and compositions for weed control |
| US10760086B2 (en) | 2011-09-13 | 2020-09-01 | Monsanto Technology Llc | Methods and compositions for weed control |
| EP2755988B1 (en) | 2011-09-13 | 2018-08-22 | Monsanto Technology LLC | Methods and compositions for weed control |
| AU2012308686B2 (en) | 2011-09-13 | 2018-05-10 | Monsanto Technology Llc | Methods and compositions for weed control |
| AU2012308660B2 (en) | 2011-09-13 | 2017-05-25 | Monsanto Technology Llc | Methods and compositions for weed control |
| CA2848689A1 (en) | 2011-09-13 | 2013-03-21 | Monsanto Technology Llc | Methods and compositions for weed control targeting pds |
| US10240161B2 (en) | 2012-05-24 | 2019-03-26 | A.B. Seeds Ltd. | Compositions and methods for silencing gene expression |
| CA2896762A1 (en) | 2013-01-01 | 2014-07-10 | A.B. Seeds Ltd. | Methods of introducing dsrna to plant seeds for modulating gene expression |
| US10683505B2 (en) | 2013-01-01 | 2020-06-16 | Monsanto Technology Llc | Methods of introducing dsRNA to plant seeds for modulating gene expression |
| AU2014249015B2 (en) | 2013-03-13 | 2020-04-16 | Monsanto Technology Llc | Methods and compositions for weed control |
| CA2905104A1 (en) | 2013-03-13 | 2014-10-09 | Monsanto Technology Llc | Control of lolium species by topical application of herbicidal composition comprising dsrna |
| US10568328B2 (en) | 2013-03-15 | 2020-02-25 | Monsanto Technology Llc | Methods and compositions for weed control |
| PL3030663T3 (pl) | 2013-07-19 | 2020-04-30 | Monsanto Technology Llc | Kompozycje i sposoby kontroli leptinotarsa |
| US9850496B2 (en) | 2013-07-19 | 2017-12-26 | Monsanto Technology Llc | Compositions and methods for controlling Leptinotarsa |
| PL3066200T3 (pl) | 2013-11-04 | 2025-03-31 | Greenlight Biosciences, Inc. | Kompozycje i sposoby do zwalczania inwazji pasożytów i szkodników stawonogów |
| UA119253C2 (uk) | 2013-12-10 | 2019-05-27 | Біолоджикс, Інк. | Спосіб боротьби із вірусом у кліща varroa та у бджіл |
| AR099092A1 (es) | 2014-01-15 | 2016-06-29 | Monsanto Technology Llc | Métodos y composiciones para el control de malezas utilizando polinucleótidos epsps |
| EP3420809A1 (en) | 2014-04-01 | 2019-01-02 | Monsanto Technology LLC | Compositions and methods for controlling insect pests |
| CN106795515B (zh) | 2014-06-23 | 2021-06-08 | 孟山都技术公司 | 用于经由rna干扰调控基因表达的组合物和方法 |
| EP3161138A4 (en) | 2014-06-25 | 2017-12-06 | Monsanto Technology LLC | Methods and compositions for delivering nucleic acids to plant cells and regulating gene expression |
| AR101348A1 (es) | 2014-07-29 | 2016-12-14 | Monsanto Technology Llc | Composiciones y métodos para el control de pestes por insectos |
| UA124255C2 (uk) | 2015-01-22 | 2021-08-18 | Монсанто Текнолоджі Елелсі | Інсектицидна композиція та спосіб боротьби з leptinotarsa |
| UY36703A (es) | 2015-06-02 | 2016-12-30 | Monsanto Technology Llc | Composiciones y métodos para la administración de un polinucleótido en una planta |
| WO2016196782A1 (en) | 2015-06-03 | 2016-12-08 | Monsanto Technology Llc | Methods and compositions for introducing nucleic acids into plants |
| WO2021202134A1 (en) * | 2020-03-30 | 2021-10-07 | Verdesian Life Sciences U.S., Llc | Oxaloacetate and related compounds as herbicidal agents |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1062206B (it) * | 1974-02-01 | 1983-09-20 | Rotta Research Lab S P A A S | Derivati della tirosina attivi sulla muscolatura liscia |
| JPS50135339A (enExample) * | 1974-04-10 | 1975-10-27 | ||
| JPS5335130B2 (enExample) * | 1974-04-18 | 1978-09-26 | ||
| GB1547758A (en) * | 1975-07-29 | 1979-06-27 | Shell Int Research | Herbicidal composition |
| US4077998A (en) * | 1975-10-28 | 1978-03-07 | Morton-Norwich Products, Inc. | Phthaloyl amino acid hydroxamic acids |
| DE3917880A1 (de) * | 1989-06-01 | 1990-12-06 | Kali Chemie Ag | Neue acylaminosaeurederivate enthaltende arzneimittel und diaetetika |
| JP3929525B2 (ja) * | 1995-05-31 | 2007-06-13 | クミアイ化学工業株式会社 | フェニルアルカン酸アミド誘導体及び農園芸用殺菌剤 |
| ES2145459T3 (es) * | 1995-05-31 | 2000-07-01 | Kumail Chemical Industry Co Lt | Derivados de fenilalcanamidas y bactericidas agrohorticolas. |
| AR004980A1 (es) * | 1995-11-29 | 1999-04-07 | Nihon Nohyaku Co Ltd | Fungicida para la fruta de cultivo, derivado de fenilalanina comprendido como ingrediente activo en el mismo y metodo para controlar enfermedades enplantas aplicando dicho fungicida. |
| JPH09208541A (ja) * | 1995-11-29 | 1997-08-12 | Nippon Nohyaku Co Ltd | 新規フェニルアラニン誘導体、その光学活性体、その塩類又は錯化合物及びその用途並びにその使用方法 |
| DE60035204T2 (de) * | 1999-09-24 | 2008-02-21 | Genentech, Inc., South San Francisco | Tyrosinderivate |
| US6649638B1 (en) * | 2002-08-14 | 2003-11-18 | Ppd Discovery, Inc. | Prenylation inhibitors and methods of their synthesis and use |
| US6664277B1 (en) * | 2002-08-14 | 2003-12-16 | Ppd Discovery, Inc. | Prenylation inhibitors containing dimethylcyclobutane and methods of their synthesis and use |
-
2002
- 2002-02-06 DE DE10204951A patent/DE10204951A1/de not_active Withdrawn
-
2003
- 2003-01-30 JP JP2003565951A patent/JP4713833B2/ja not_active Expired - Fee Related
- 2003-01-30 EP EP03702568A patent/EP1474381B1/de not_active Expired - Lifetime
- 2003-01-30 US US10/503,762 patent/US20050215435A1/en not_active Abandoned
- 2003-01-30 DE DE50301261T patent/DE50301261D1/de not_active Expired - Lifetime
- 2003-01-30 WO PCT/EP2003/000926 patent/WO2003066576A1/de not_active Ceased
- 2003-01-30 AU AU2003205712A patent/AU2003205712A1/en not_active Abandoned
- 2003-01-30 CA CA002474354A patent/CA2474354A1/en not_active Abandoned
- 2003-01-30 AT AT03702568T patent/ATE305448T1/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7687435B2 (en) | 2003-12-19 | 2010-03-30 | Basf Aktiengesellschaft | Benzoyl-substituted phenylalanineamides |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1474381B1 (de) | 2005-09-28 |
| DE10204951A1 (de) | 2003-08-14 |
| WO2003066576A1 (de) | 2003-08-14 |
| ATE305448T1 (de) | 2005-10-15 |
| DE50301261D1 (de) | 2006-02-09 |
| JP4713833B2 (ja) | 2011-06-29 |
| JP2005525330A (ja) | 2005-08-25 |
| EP1474381A1 (de) | 2004-11-10 |
| AU2003205712A1 (en) | 2003-09-02 |
| US20050215435A1 (en) | 2005-09-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |