AP131A - Fungicides. - Google Patents
Fungicides. Download PDFInfo
- Publication number
- AP131A AP131A APAP/P/1989/000137A AP8900137A AP131A AP 131 A AP131 A AP 131A AP 8900137 A AP8900137 A AP 8900137A AP 131 A AP131 A AP 131A
- Authority
- AP
- ARIPO
- Prior art keywords
- compound
- hydrogen
- ring
- acid
- optionally substituted
- Prior art date
Links
- 239000000417 fungicide Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 239000000203 mixture Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 241000233866 Fungi Species 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 230000000361 pesticidal effect Effects 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 241000607479 Yersinia pestis Species 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000005864 Sulphur Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- HETSDWRDICBRSQ-UHFFFAOYSA-N 3h-quinolin-4-one Chemical group C1=CC=C2C(=O)CC=NC2=C1 HETSDWRDICBRSQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 239000007787 solid Substances 0.000 description 16
- -1 amino, carboxy Chemical group 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LGPVTNAJFDUWLF-UHFFFAOYSA-N 2-amino-4-fluorobenzoic acid Chemical compound NC1=CC(F)=CC=C1C(O)=O LGPVTNAJFDUWLF-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010410 dusting Methods 0.000 description 3
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- UBFRSTYHLYPSND-UHFFFAOYSA-N methyl 2-amino-4-fluorobenzoate Chemical compound COC(=O)C1=CC=C(F)C=C1N UBFRSTYHLYPSND-UHFFFAOYSA-N 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- CWVFOAVBTUHQCZ-UHFFFAOYSA-N 6-fluoro-1h-indole-2,3-dione Chemical compound FC1=CC=C2C(=O)C(=O)NC2=C1 CWVFOAVBTUHQCZ-UHFFFAOYSA-N 0.000 description 2
- JEVWCMDHSLNNDR-UHFFFAOYSA-N 7-fluoro-1h-3,1-benzoxazine-2,4-dione Chemical compound N1C(=O)OC(=O)C=2C1=CC(F)=CC=2 JEVWCMDHSLNNDR-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241000233679 Peronosporaceae Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000813090 Rhizoctonia solani Species 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241001617088 Thanatephorus sasakii Species 0.000 description 2
- 241000228452 Venturia inaequalis Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000005553 drilling Methods 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- 238000003359 percent control normalization Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
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- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical class C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical compound CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
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Abstract
Compounds of formula
Description
This invention relates to compounds having pesticidal and especially fungicidal activity.
3,l-Benzoxazin-4-ones, which can be considered as ring-closed derivatives of anthranilic acids, have been disclosed as having pesticictel activity (eg DE 2241012 and EP 17 931) but none of these describe 7-fluoro substituted compounds. It will be appreciated that the 7-position on the 3,l-benzoxazin-4-one ring corresponds to the 4position of the parent anthranilic acid. Certain
7-fluoro substituted quinolones have been disclosed as having pharmaceutical activity (eg EP 135 367, GB 2047691 and 2111975) but no agricultural uses are described for these compounds. 4-Fluoroanthranilic acid itself and certain other derivatives are known but we are not aware that any agricultural pesticidal use has been disclosed for these compounds. We have now found that
4-fluroanthranilic acid and certain derivatives have pesticidal activity and especially activity against phytopathogenic fungi.
Thus, according to the invention there is provided a pesticidal composition which comprises a compound of formula I
R1 where
R1 is hydrogen, optionally substituted alkyl, cycloalkyl, alkenyl or alkynyl;
and either (i) A is hydroxy, XR2, NR3R4 or NHNR3R4, and
a) B is hydrogen, alkyl, cycloalkyl, alkenyl or alkynyl, each of which is optionally 5 substituted, non-aromatic heterocyclyl or the group COR4, COOR2, CXNR2R3, SO2R2, SO2NR5R6,
PX(OR2)2 or PX(NR5R6)2, or
b) B and R1 together represent =CR2R3, where
R2 and R3 are as defined below or together are alkylene; or (ii) A and B together with the atoms to which they are attached can form a ring, in which case R1 can also represent a bond between the nitrogen to which it is attached and B;
R2 is alkyl, cycloalkyl, alkenyl or alkynyl, each of which is optionally substituted, or is aryl or a non-aromatic heterocyclyl group;
R3 is hydrogen, alkyl, cycloalkyl, alkenyl or alkynyl, each of which is optionally substituted, or is -SO2R4;
R4 has the same meaning as R2 or is hydrogen;
R5 and R6 are the same or different optionally substituted alkyl or alkenyl groups;
X is oxygen or sulphur;
and where -NR2R3, -NR3R4 and -NR5R6 can form a ring; and agiculturally acceptable salts with an organic or inorganic base of any compound which is an acid or with an organic or inorganic acid of any compound which is a base; said compound being in admixture with an agriculturally acceptable diluent or carrier.
Alkyl groups are preferably of 1 to 4 carbon atoms, especially methyl. Alkenyl and alkynyl groups are preferably of 2 to 4 carbon atoms. Cycloalkyl groups are preferably of 3 to 8 carbon atoms. Substituents, when present on any alkyl, cycloalkyl, alkenyl or alkynyl
APO0013 1
BAD ORIGINAL group, include halogen, alkoxy (e.g. of 1 to 4 carbon atoms), haloalkoxy, hydroxy, alkylthio, nitro, optionally substituted amino, carboxy, alkoxycarbonyl, acyloxy, aryl and trialkylsilyl. Cycloalkyl groups may also be substituted by alkyl. Aryl groups are usually phenyl, optionally substituted, e.g. by halogen, alkyl, haloalkyl, alkoxy, optionally substituted amino or nitro. The term aryl may include heteroaryl groups. The terms heteroaryl and heterocyclyl include groups such as thienyl, furyl, pyridyl, pyrimidinyl, pyrazolyl, thiazolyl, thiazolinyl, thiazolidinyl, oxazolyl, benzimidazolyl, tetrazolyl, benzoxazolyl, thiadiazolyl, dioxolanyl, imidazopyridinyl,
1,3-benzoxazinyl, 1,3-benzothiazinyl, oxazolopyridinyl, tetrahydropyranyl, triazolyl, triazinyl, imidazolyl, morpholino, benzofuranyl, pyrazolinyl, quinolinyl, quinazolinyl, dihydroquinazolinyl or benzothiazolyl, which themselves may be substituted, e.g. as for phenyl. The term acyl includes the residue of sulphonic and phosphorus containing acids as well as carboxylic acids. Acyl groups are preferably alkanoyl, e.g. of 1 to 4 carbon atoms.
Amino groups may be substituted, e.g. by one or two alkyl groups or two substituents can form a ring, e.g.
morpholine ... piperidine.
When -NR2R3, -NR3R4 and -NR5R6 form a ring this is generally a 5 to 7 membered ring which may be substituted and may contain other hetero atoms, e.g. morpholine, thiomorpholine, piperidine or imidazole.
When A and B form part of a ring this is generally a 5 or 6 membered ring which besides the nitrogen can contain other hetero atoms, such as nitrogen, oxygen, phosphorus or sulphur, and can be further substituted. R1 can represent a bond between the nitrogen atom and the adjacent atom which is not part of the fused benzo ring.
BAD original
Examples of compounds of formula of this type are
APO 00 1 3 1
Many of the compounds of formula I are novel and the invention thus include all such novel compounds and especially those where the groups are as defined above with the proviso (i) when A is hydroxy or alkoxy and R1 is hydrogen, then
B is not hydrogen or acetyl, (ii) when R1 is hydrogen and if A and B form a ring then it is not one in which the group Y is CO or COO, (iii) when A is alkoxy and R1 is hydrogen, then B is not methyl, or (iv) if A and B form a ring then it is not a 4-quinolone ring .
Some novel compounds of activity but still have formula I have weak pesticidal utility as intermediates and such
BAD ORIGINAL Oi compounds also form one aspect of the invention.
The compounds of the invention have activity as fungicides, especially against soil-borne fungal diseases of plants, e.g. Rhizoctonia solani and Pythium ultlmum.
They may however have activity against other fungi, for example e.g. vine downy mildew (Plasmopara vltlcola), rice sheath blight (Pellicularia sasakii), grey mould (Botrytis cinerea), and apple scab (Venturia inaequalis). Other fungi against which the compounds may be active include other general pathogens of Deuteromycete, Ascomycete, Phycomycete or Basidiomycete origin.
Some of the compounds also have other pesticidal activity, especially herbicidal and insecticidal activity.
The invention thus also provides a method of combating 15 pests, and especially fungi, particularly soil-borne fungi at a locus infested or liable to be infested therewith, which comprises applying to the pest or its locus a compound of formula I.
The composition of the invention may of course include 20 more than one compound of the invention.
In addition the composition can comprise one or more additional active ingredients, for example compounds known to possess plant-growth regulant, herbicidal, fungicidal, insecticidal or acaricidal properties. Alternatively the compounds of the invention can be used in sequence with the other active ingredient.
The diluent or carrier in the composition of the invention can be a solid or a liquid optionally in association with a surface-active agent, for example a dispersing agent,
BAD original $ emulsifying agent or wetting agent. Suitable surface-active agents include anionic compounds such as a carboxylate, for example a metal carboxylate of a long chain fatty acid; an N-acylsarcosinate; mono- or di-esters of phosphoric acid with fatty alcohol ethoxylates or salts of such esters; fatty alcohol sulphates such as sodium dodecyl sulphate, sodium octadecyl sulphate or sodium cetyl sulphate; ethoxylated fatty alcohol sulphates; ethoxylated alkylphenol sulphates; lignin sulphonates;
petroleum sulphonates; alkyl-aryl sulphonates such as alkyl-benzene sulphonates or lower alkylnaphthalene sulphonates, e.g. butyl-naphthalene sulphonate; salts of sulphonated naphthalene-formaldehyde condensates; salts of sulphonated phenol-formaldehyde condensates; or more complex sulphonates such as the amide sulphonates, e.g. the sulphonated condensation product of oleic acid and N-methyl taurine or the dialkyl sulphosuccinates, e.g. the sodium sulphonate of dioctyl succinate. Nonionic agents include condensation products of fatty acid esters, fatty alcohols, fatty acid amides or fatty-alkyl- or alkenyl-substituted phenols with ethylene oxide, fatty esters of polyhydric alcohol ethers, e.g. sorbitan fatty acid esters, condensation products of such esters with ethylene oxide, e.g. polyoxyethylene sorbitan fatty acid esters, block copolymers of ethylene oxide and propylene oxide, acetylenic glycols such as 2,4,7,9-tetramethyl-5decyne-4,7-diol, or ethoxylated acetylenic glycols.
Examples of a cationic surface-active agent include, for instance, an aliphatic mono-, di-, or polyamine as an 30 acetate, naphthenate or oleate; an oxygen-containing amine such as an amine oxide or polyoxyethylene alkylamine; an amide-linked amine prepared by the condensation of a carboxylic acid with a di- or polyamine; or a quaternary ammonium salt. ____—'
AP 0 0 0 1 3 1
BAD ORIGINAL ft
The compositions of the invention can take any form known in the art for the formulation of agrochemicals, for example, a solution, a dispersion, an aqueous emulsion, a dusting powder, a seed dressing, a fumigant, a smoke, a dispersible powder, an emulsifiable concentrate or granules. Moreover it can be in a suitable form for direct application or as a concentrate or primary composition which requires dilution with a suitable quantity of water or other diluent before application.
An emulsifiable concentrate comprises a compound of the invention dissolved in a water-immiscible solvent which is formed into an emulsion with water in the presence of an emulsifying agent.
A dusting powder comprises a compound of the invention intimately mixed and ground with a solid pulverulent diluent, for example, kaolin.
A granular solid comprises a compound of the invention associated with similar diluents to those which may be employed in dusting powders, but the mixture is granulated by known methods. Alternatively it comprises the active ingredient absorbed or adsorbed on a pre-granular diluent, for example, Fuller's earth, attapulgite or limestone grit.
Wettable powders, granules or grains usually comprise the active ingredient in admixture with a suitable surfactant and an inert powder diluent such as china clay.
Another suitable concentrate is a flowable suspension concentrate which is formed by grinding the compound with water or other liquid, a wetting agent and a suspending ' ^ORIGINAL agent.
The concentration of the active ingredient in the composition of the present invention, as applied to the target locus is preferably within the range of 0.01 to 3.0 per cent by weight, especially 0.01 to 1.0 per cent by weight. In a primary composition the amount of active ingredient can vary widely and can be, for example, from 5 to 95 per cent by weight of the composition.
In the method of the invention the compound is generally 10 applied to seeds, plants or their habitat. Thus the compound can be applied directly to the soil before, at or after drilling so that the presence of active compound in the soil can control the growth of fungi which may attack seeds. When the soil is treated directly the active compound can be applied in any manner which allows it to be intimately mixed with the soil such as by spraying, by broadcasting a solid form of granules, or by applying the active ingredient at the same time as drilling by inserting it in the same drill as the seeds. A suitable application rate is within the range of from 0.05 to 20 kg per hectare, more preferably from 0.1 to 10 kg per hectare.
The compounds of the invention may be prepared in a variety of ways for example as shown in the following reaction schemes. Methods will also be apparent from the various Examples.
APO 0013 1
BAD ORIGINAL ft / J
BAD ORIGINAL
The invention is illustrated in the following Examples. Structures of isolated novel compounds were confirmed by elemental and/or other appropriate analyses.
Temperatures are in *C.
Example 1
A mixture of phthalic anhydride (4.8 g) and 4-fluoroanthranilic acid (5 g) in diphloromethane (100 ml) was stirred at room temperature for 48 hours and the solid collected and washed with dichloromethane to give
N-(2-carboxybenzoyl)-4-fluoroanthranilic acid,
m.p. 187-188’. (Compound 1)
Example 2
A mixture of acetyl chloride (4.6 ml) and 4-fluoroanthranilic acid (5 g) in acetic anhydride (100 ml) was heated under reflux for 48 hours, cooled and filtered. The filtrate was added to ice/water, stirred for 1 hour and extracted with ethyl acetate. The extract was dried and the solvent removed under reduced pressure to give 7-fluoro-2-methyl-3,l-benzoxazin-4-one, m.p. 159-160*.
(Compound 2)
Example 3
Sodium hydroxide (2 pellets; approx 0.15 g) was added to a mixture of phenol (1.08 g) and 7-fluoro1H-3,l-benzoxazine-2, 4-dione (2 g) followed by tetrahydrofuran (4 ml). The mixture was heated on a steam bath until gas evolution ceased. It was then cooled, diluted with ethyl acetate (100 ml), the liquid collected and washed with aqueous sodium carbonate, dried, treated with charcoal and evaporated. The crude product was recrystallised from diisopropyl ether/light petroleum to give phenyl 4-fluoroanthranilate, m.p. 69-70*. (Compound
3)
AP 0 0 0 1 3 1
BAD ORIGINAL ft
Example 4
A solution of aniline (1.77 g) in acetic acid (50 ml) was added to a solution of 7-fluoro-lH-3,1-benzoxazine2,4-dione (1 g) in acetic acid (100 ml) and the mixture heated at 100* for 20 minutes. It was then poured into water and the precipitate collected, dried and recrystallised from toluene fo give N1-phenyl4-fluoroanthranilamide, m.p. 120-122*. (Compound 4)
Example 5
A solution of phenyl isocyanate (2.98 g) in toluene (30 ml) was added dropwise to a stirred suspension of 4-fluoroanthranilic acid (3.88 g) in toluene (80 ml) at 50*. The mixture was stirred at 90* for 2 hours and the toluene evaporated under reduced pressure (30 ml). The residue was recrystallised from hexane/ethyl acetate to give 4-fluoro-N-phenylcarbamoylanthranilic acid, m.p. 163-166*. (Compound 5)
Example 6
A mixture of the product of Example 5 (2 g) and polyphosphoric acid (150 g) was heated at 150* for 5 hours. It was then added to ice, and extracted with ethyl acetate. The extract was dried, the solvent removed undet reduced pressure and the product recrystallised from aqueous ethanol to give 7-fluoro-3-phenylquinazoline2,4(1H,3H)-dione, m.p. 304-306*. (Compound 6)
Example 7
A mixture of 4-fluoroanthranilic acid (2 g), aqueous formaldehyde (37-40% w/v; 6.5 ml) and palladium on charcoal (1 g of 5%) in acetic acid (70 ml) was hydrogenated over 18 hours during which 570 ml hydrogen was taken up. The mixture was filtered, evaporated under reduced pressure and the residue recrystallised from toluene to give 4-fluoro-N-methylanthranilic acid, m.p. 180-181*. (Compound 7)
Example 8
A mixture of 7-fluoro-lH-3,l-benzoxazine-2,4-dione (13.5 g) and sodium methoxidp (0.2 g) in methanol (30 ml), was heated on a steam bath until vigorous bubbling ceased. It was then heated under reflux for 3| hours, cooled, added to aqueous sodium bicarbonate (10%; 300 ml) and extracted with ethyl acetate. The extract was washed with water dried and evaporated to give methyl 4-fluoroanthranilate, mp 68-70*. (Compound 8)
Example 9
Propionyl chloride (1.7 ml) was added to a solution of
4-fluoroanthranilic acid (1 g) and triethylamine (2.8 ml) in 1,4-dioxane (30 ml). The mixture was heated under reflux for 4 hours, cooled and concentrated under reduced pressure. The residue was suspended in ethyl acetate and extracted with water. The organic phase was dried and evaporated and the residue purified by silica gel chromatography to give 4-fluoro-N-propionylanthranilic acid, mp 170-171*. (Compound 9)
Example 10
Methyl chloroformate (1.22 g) was added dropwise at -3* to
1* (ice bath cooling) to a stirred solution of 4-fluoroanthranilic acid (2 g) and triethylamine (1.31 g) in dry tetrahydrofuran (30 ml). The mixture was then stirred at room temperature for 18 hours. The reaction mixture was diluted with ice-water and extracted with ethyl acetate.
BAD ORIGINAL
AP 0 0 0 1 3 1
The extract was washed with dilute hydrochloric acid, then with water and dried. Evaporation of the solvent gave a solid residue which was recrystallised from 1:1 ethyl acetate: hexane to give 4-fluoro-N-(methoxycarbonyl) anthranilic acid, mp 161.5-162.5*. (Compound 10)
Example 11 ,
Sodium hydride (80% in oil; 1.2 g) was added slowly to a stirred suspension of 7-fluoro-lH-3,1-benzoxazine2,4-dione (7 g). Effervescence occurred and a clear solution was produced. Ethyl bromoacetate (4.5 ml) was added and the mixture was stirred at room temperature for 18 hours. The solvent was evaporated and the residue was diluted with water. The solid (9.5 g) was filtered off and washed with water and hexane and dried. This solid (5.4 g) was added to a solution of sodium carbonate (5.3 g) in water (60 ml). After stirring for 6 hours the undissolved solid was filtered off. The filtrate was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The solid was purified by flash chromatography and recrystallised from diisopropyl ether to give 4-fluoro-N-(ethoxycarbonylmethyl)- anthranilic acid, mp. 123-125*. (Compound 11)
Example 12
Compound 11 (2.3 g) was stirred with IN sodium hydroxide (60 ml) for 24 hours. The solution was acidified to pH 4 with hydrochloric acid and the precipitated solid was filtered off, washed with a small amount of water and dried. Recrystallisation from ethyl acetate - hexane gave 4-fluoro-N-(carboxymethylJanthranilic acid, mp. 210* (dec.) (Compound 12)
Example 13
4-Fluoroanthranilic acid (1.0 g) and 4-methylbenzaldehyde (0.77 g) were added to ethanol (100 ml). The mixture was heated under reflux for 6 hours, cooled and evaporated under reduced pressure. The residue was recrystallised from toluene to give 4-fluoro-N-(4-methylbenzylidene)anthranilic acid, mp 144-5*., (Compound 13)
Example 14
4-Fluoroanthranilic acid (1.5 g) and sodium hydroxide 10 (0.4 g) were stirred in cold water (100 ml) at ca. 5*.
Benzenesulphonyl chloride (1.25 ml) was added and the mixture was stirred overnight, acidified and extracted with dichloromethane. The extracts were washed, dried and evaporated to give 4-fluoro-N-(phenylsulphonyl)anthranilic acid, mp 158-9*. (Compound 14)
Example 15
Sodium hydride (1.2 g of 80% suspension in oil) was added to a suspension of 7-fluoro-lH-3,l-benzoxazine-2,4-dione (7 g) in dimethylformamide (50 ml). After evolution of hydrogen had ceased, ethyl bromoacetate (4.5.ml) was added which caused an exothermic reaction and eventually a clear solution. After 18 hours, the solution was concentrated and water added. The resulting white solid was collected, washed with water and light petroleum and dried. The product was recrystallised from ethyl acetate/ diisopropyl ether to give l-(ethoxycarbonylmethyl)-7-fluoro1H-3,l-benzoxazine-2,4-dione, mp 167-168*. (Compound 15)
AP o 0 0 1 3 1
BAD ORIGINAL
Example 16
Sodium hydride (80% in oil; 0.36 g) was added portionwise to a stirred solution of 6-fluoro-lH-indole-2, 3-dione (2 g) in dry dimethylformamide (25 ml). After effervescence had ceased, ethyl bromoacetate (2 g) was added dropwise at 25* to the stirred solution. The orange mixture was stirred at room temperature for 18 hours and then poured into ice-water. The precipitated solid was filtered off, washed with water and dried.
Recrystallisation from ethyl acetate gave 6-fluorol-(ethoxycarbonylmethyl)-lH-indole-2,3-dione, mp 168-169*. (Compound 16)
Example 17
4-Fluoroanthranilic acid (2 g) was added portionwise to trifluoroacetic anhydride (16 ml). After stirring and refluxing for 4 hours, the mixture was cooled and excess trifluoroacetic anhydride was removed by evaporation under reduced pressure. The resultant light brown solid was stirred at room temperature with a mixture of tetrahydrofuran (50 ml) and water (10 ml) for 18 hours.
Solvent was removed by evaporation under reduced pressure to give a white solid. Recrystallisation from toluene gave 4-fluoro-N-(trifluoroacetyl)anthranilic acid, mp 166-167.5*. (Compound 17)
Example 18
A solution of methyl 4-fluoroanthranilate (1.8 g)
3,4-dihydro-2H-pyran (0.9 g) and pyridinium tosylate (0.1 g) in dichloromethane (20 ml) was left standing at
20* for 4 days. This solution was then washed with water (10 ml), dried with magnesium sulphate and evaporated. Column chromatography on silica gel, using diethyl ether as eluent, followed by recrystallisation of the product from ethyl acetate/diisopropyl ether gave methyl
4-fluoro-N-(tetrahydropyran-2-yl) anthranilate, mp 44-45*. (Compound 18).
Example 19
Methanesulphonyl chloride (0.68 g) was added dropwise to a stirred solution of methyl 4-fluoroanthranilate (1 g) in pyridine (dried over 4A sieves, 10 ml) at 0-5*. After 18 hours at room temperature, the mixture was cooled to 0-5* and further methanesulphonyl chloride (0.68 g) was added dropwise. The mixture was stirred for 24 hours at room temperature. Aqueous work up and recrystallisation from ethanol gave methyl N-(methylsulphonyl)-4-fluoroanthranilate , mp 115.5-116.5*. (Compound 19)
Example 20
7-Fluoro-lH-3,l-benzoxazine-2,4-dione (2.0 g), sodium hydroxide (0.05 g) and 2-(trimethylsilyl)ethanol (1.31 g) 25 were heated together at 100* for 30 minutes until effervescence ceased. After cooling, the residue was suspended in diisopropyl ether, then filtered and evaporated. The residue was recrystallisedfrom petroleum ether to give 2-(trimethylsilyl)ethyl 4-fluoro30 anthranilate, mp 43-44
APO η o13 1
BAD ORIGINAL ft
Example 21
Sodium hydride (0.41 g of 80% suspension in oil) was added to a solution of 7-fluoro-lH-3,l-benzoxazine-2,4-dione (2.5 g) in dimethylformamide (30 ml). The mixture was cooled to keep the temperature below 30* and then stirred, for 1 hour until a clear solution was obtained. A solution of allyl bromide (1.2 ml) in, dimethylformamide (30 ml) was added dropwise with cooling and the mixture stirred at room temperature overnight. The mixture was poured into water and extracted with dichloromethane. The extract was washed with water, dried and evaporated and the residue added to aqueous sodium carbonate (10%; 20 ml) and stirred for 3 hours, acidified with hydrochloric acid to pH 3, filtered and the solid washed with water and dried to give
N-allyl-4-fluoroanthranilic acid, mp 136-139*.
(Compound 21)
Compound 7 was also prepared using the method of this Example.
Example 22
In a similar manner to one of the processes disclosed in the previous Examples, the following were obtained
A
B
Cpd
m.p.(*)
10 | 22 23 | (4-N02-Ph)-0 (4-MeO-Ph)-O | H H | 159-160 97-8 |
24 | (4-COOH-Ph)-0 | H | >250 | |
25 | (3-F-Ph)-NH | H | 126-8 | |
26 | (EtO2C)2CH-NH | H | 134-5 | |
15 | 27 | OH | COPh | 206-7 |
28 | OH | CHjCOOPr* | 192-3 | |
29 | OH | CH2COOMe | 170-171 | |
30 | OH | CH2CONHEt | 228-230 | |
31 | OH | cocci3 | 214-215 | |
20 | 32 | OMe | CH2COOEt | 64-7 |
The | following were also | obtained: | ||
a) | 7-fluoro-2-phenyl-3,1 | -benzoxazin- | 4-one, m.p. | |
(Compound 33) | ||||
b) | 7-fluoro-2-ethyl-3,1- | benzoxazine- | 4-one, m.p. | |
25 | (Compound 34) | |||
c) | 1-( isopropoxycarbonyl | methyl)-7-fluoro- | ||
1H-3,l-benzoxazine-2, | 4-dione, mp | 163-164* |
140-142*
107-109
AP 0 0 0 1 3 1 (Compound 35)
d) methyl 4-fluoro-N-(2,2,2-trichloroethylidene)30 anthranilic acid. (compound 36)
c) 1-(ethylcarbamoylmethyl)-7-fluoro-lH-3,1-benzoxazine2,4-dione, mp 202-203* (Compound 37)
BAD ORIGINAL
Test Example
Compounds are assessed for activity against one or more of the following fungi:
a) Foliar tests
Plasmopara viticola: vine downy mildew (PV)
Pellicularia sasakii: rice sheath blight (PS)
Botrytis cinerea: grey mould of tomato (BC)
Venturia inaequalis: apple scab (VI)
Aqueous solutions or dispersions of the compounds at the 10 desired concentration, including a wetting agent, were applied by spray or by drenching the stem base of the test plants. These plants were then inoculated with appropriate test pathogens and kept under controlled environment conditions suitable for maintaining plant growth and development of the disease. After an appropriate time, the degree of infection of the leaf surface was visually estimated. Compounds were considered active if they gave greater than 50% control of the disease at a concentration of 125 ppm (w/v) or less.
b) Soil pathogen test
Rhizoctonia solani (RS)
Pythium ultimum (PU)
Flasks containing maize meal/sand were inoculated with the test fungus and then incubated. The maize meal/sand cultures were used to infest potting compost which was then put into plastic pots. Aqueous solutions or dispersions of the compounds, including a wetting agent, were added to the pots to give a desired concentration of compound in each pot. Control pots were set up by adding similar solutions or dispersions without the test compound. Immediately after application of the test compound each pot was sown with a number of cabbage or cotton seeds. The seeds are covered with the treated infested soil and the pots incubated at 22*C under humid conditions for 6-21 days depending on crop. The number of emerged seedlings is counted and percentage disease control calculated by comparison with the untreated infested pots. Compounds are considered active if they give greater than 50% control of the disease at a concentration of 100 parts by weight of compound or less per million parts by volume of soil.
The following known compounds were also tested:
Compound A: 4-fluoroanthranilic acid
Compound B: N-acetyl-4-fluoroanthranilic acid
Compound C: 7-fluoro-lH-3,l-benzoxazine-2,4-dione Compound D: 6-fluoro-lH-indole-2,3-dione Compound E: methyl 4-fluoro-N-methylanthranilate
AP 0 n 0 1 3 1
Activities were demonstrated as follows (+ = active)
Compound
No
PV PS BC VI RS PU
1
3
9
12 13 +
23
33
A
B
C
D +
+ +
+ +
+ +
+ +
+ +
+ +
+ +
+ + + + + +
+
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Claims (3)
1. A pesticidal composition which comprises a compound of formula I i
R1 where
10 R1 is hydrogen, optionally substituted alkyl cycloalkyl, alkenyl or alkynyl;
and either (i) A is hydroxy, XR2, NR3R4 or NHNR3R4, and
a) B is hydrogen, alkyl, cycloalkyl, alkenyl or
15 alkynyl, each of which is optionally substituted, non-aromatic heterocyclyl or the group COR4, COOR2, CXNR2R3, SO2R2,
SO2NR5R6, PX(OR2)
2 or PX(NR5R6)2, or
b) B and R1 together represent =CR2R3, where
20 r2 and R3 are as defined below or together are alkylene; or (ii) A and B together with the atoms to which they are attached can form a ring, in which case R1 can also represent a bond between the nitrogen to which
25 it is attached and B;
R2 is alkyl, cycloalkyl, alkenyl or alkynyl, each of which is optionally substituted, or is aryl or a non-aromatic heterocyclyl group;
R3 is hydrogen, alkyl, cycloalkyl, alkenyl or alkynyl, 30 each of which is optionally substituted, or is
AP 0 0 0 1 3 1
R5 and R6 are the same or different optionally substituted alkyl or alkenyl groups;
X is oxygen or sulphur;
and where -NR2R3, -NR3R4 and -NR5R6 can form a ring;
5 and agiculturally acceptable salts with an organic or inorganic base of any compound which is an acid or with an organic or inorganic acid of any compound which is a base; said compound being in admixture with an agriculturally acceptable diluent or carrier.
10 2. A compound of formula I as disclosed in claim 1, in which A, B and R1'6 are as defined in claim 1, with the proviso (i) when A is hydroxy or alkoxy and R1 is hydrogen, then B is not hydrogen or acetyl,
15 (ii) when R1 is hydrogen and if A and B form a ring then it is not one in which the group Y is CO or COO, (iii) when A is alkoxy and R1 is hydrogen, then B is not methyl, or
20 (iv) if A and B form a ring then it is not a
4-quinolone ring.
3. A method of combating pests, and especially fungi, particularly soil-borne fungi at a locus infested or liable to be infested therewith, which comprises
25 applying to the pest or its locus a compound of formula I as defined in claim 1.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB888820129A GB8820129D0 (en) | 1988-08-24 | 1988-08-24 | Fungicides |
Publications (2)
Publication Number | Publication Date |
---|---|
AP8900137A0 AP8900137A0 (en) | 1989-10-31 |
AP131A true AP131A (en) | 1991-04-20 |
Family
ID=10642659
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
APAP/P/1989/000137A AP131A (en) | 1988-08-24 | 1989-08-23 | Fungicides. |
Country Status (10)
Country | Link |
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US (1) | US5093364A (en) |
EP (1) | EP0360417A3 (en) |
JP (1) | JPH02149502A (en) |
KR (1) | KR900002703A (en) |
AP (1) | AP131A (en) |
AU (1) | AU4009589A (en) |
DK (1) | DK415189A (en) |
GB (1) | GB8820129D0 (en) |
IL (1) | IL91385A0 (en) |
ZA (1) | ZA896427B (en) |
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- 1989-08-21 EP EP19890308459 patent/EP0360417A3/en not_active Withdrawn
- 1989-08-22 IL IL91385A patent/IL91385A0/en unknown
- 1989-08-23 AP APAP/P/1989/000137A patent/AP131A/en active
- 1989-08-23 US US07/397,726 patent/US5093364A/en not_active Expired - Fee Related
- 1989-08-23 DK DK415189A patent/DK415189A/en not_active Application Discontinuation
- 1989-08-23 ZA ZA896427A patent/ZA896427B/en unknown
- 1989-08-24 KR KR1019890012148A patent/KR900002703A/en not_active Application Discontinuation
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Also Published As
Publication number | Publication date |
---|---|
AP8900137A0 (en) | 1989-10-31 |
IL91385A0 (en) | 1990-04-29 |
DK415189A (en) | 1990-02-25 |
KR900002703A (en) | 1990-03-23 |
EP0360417A2 (en) | 1990-03-28 |
US5093364A (en) | 1992-03-03 |
AU4009589A (en) | 1990-07-19 |
ZA896427B (en) | 1990-09-26 |
GB8820129D0 (en) | 1988-09-28 |
EP0360417A3 (en) | 1991-10-23 |
DK415189D0 (en) | 1989-08-23 |
JPH02149502A (en) | 1990-06-08 |
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