PH26301A - N-phenylalkylbenzamide fungicides - Google Patents
N-phenylalkylbenzamide fungicides Download PDFInfo
- Publication number
- PH26301A PH26301A PH37724A PH37724A PH26301A PH 26301 A PH26301 A PH 26301A PH 37724 A PH37724 A PH 37724A PH 37724 A PH37724 A PH 37724A PH 26301 A PH26301 A PH 26301A
- Authority
- PH
- Philippines
- Prior art keywords
- compound
- test
- composition
- chloro
- disease
- Prior art date
Links
- 239000000417 fungicide Substances 0.000 title claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 160
- 239000000203 mixture Substances 0.000 claims description 67
- 241000221785 Erysiphales Species 0.000 claims description 44
- 230000000694 effects Effects 0.000 claims description 35
- SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 31
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 25
- 230000000855 fungicidal effect Effects 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 239000005747 Chlorothalonil Substances 0.000 claims description 8
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical group ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 4
- 229930182558 Sterol Natural products 0.000 claims description 3
- 150000003432 sterols Chemical class 0.000 claims description 3
- 235000003702 sterols Nutrition 0.000 claims description 3
- 230000017858 demethylation Effects 0.000 claims description 2
- 238000010520 demethylation reaction Methods 0.000 claims description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 2
- FVLVBVSILSHUAF-UHFFFAOYSA-N n-benzyl-3,5-dimethyl-n-propan-2-ylbenzamide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N(C(C)C)CC1=CC=CC=C1 FVLVBVSILSHUAF-UHFFFAOYSA-N 0.000 claims description 2
- 229940054066 benzamide antipsychotics Drugs 0.000 claims 3
- 150000003936 benzamides Chemical class 0.000 claims 3
- 206010008583 Chloroma Diseases 0.000 claims 1
- 230000002411 adverse Effects 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000004464 cereal grain Substances 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 abstract description 16
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 79
- 238000012360 testing method Methods 0.000 description 79
- 201000010099 disease Diseases 0.000 description 77
- 241000209140 Triticum Species 0.000 description 44
- 235000021307 Triticum Nutrition 0.000 description 36
- 241000196324 Embryophyta Species 0.000 description 32
- 238000011081 inoculation Methods 0.000 description 26
- 238000011282 treatment Methods 0.000 description 25
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 19
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 19
- 239000005822 Propiconazole Substances 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 244000052769 pathogen Species 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 240000005979 Hordeum vulgare Species 0.000 description 10
- 239000005820 Prochloraz Substances 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000007900 aqueous suspension Substances 0.000 description 10
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 10
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 235000007340 Hordeum vulgare Nutrition 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 8
- 241001480061 Blumeria graminis Species 0.000 description 8
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 8
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 8
- 229920001285 xanthan gum Polymers 0.000 description 8
- 239000000230 xanthan gum Substances 0.000 description 8
- 229940082509 xanthan gum Drugs 0.000 description 8
- 235000010493 xanthan gum Nutrition 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- -1 triademefon Chemical compound 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 6
- 206010039509 Scab Diseases 0.000 description 5
- 241001533598 Septoria Species 0.000 description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 5
- 229940093499 ethyl acetate Drugs 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 230000002195 synergetic effect Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 208000031888 Mycoses Diseases 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 244000070406 Malus silvestris Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 229920001213 Polysorbate 20 Polymers 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 229960001701 chloroform Drugs 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 230000001717 pathogenic effect Effects 0.000 description 3
- 229920001983 poloxamer Polymers 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 2
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical class NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 description 2
- 241000895523 Blumeria graminis f. sp. hordei Species 0.000 description 2
- 241000895502 Blumeria graminis f. sp. tritici Species 0.000 description 2
- 241000221787 Erysiphe Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical class F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241000233679 Peronosporaceae Species 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 241000540505 Puccinia dispersa f. sp. tritici Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 241001360088 Zymoseptoria tritici Species 0.000 description 2
- 150000003974 aralkylamines Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 2
- 235000021028 berry Nutrition 0.000 description 2
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical class F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- CVTFNNJUXOBPMI-UHFFFAOYSA-N (1,2-dichloro-2-diphenylphosphanylethyl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(Cl)C(Cl)P(C=1C=CC=CC=1)C1=CC=CC=C1 CVTFNNJUXOBPMI-UHFFFAOYSA-N 0.000 description 1
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- OPUPBQQWLWFCPU-UHFFFAOYSA-N 2-benzylbenzamide Chemical class NC(=O)C1=CC=CC=C1CC1=CC=CC=C1 OPUPBQQWLWFCPU-UHFFFAOYSA-N 0.000 description 1
- OXNDXWTURCMXJF-UHFFFAOYSA-N 2-chloro-n-hydroxybenzenecarboximidoyl chloride Chemical compound ON=C(Cl)C1=CC=CC=C1Cl OXNDXWTURCMXJF-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- DYBIGIADVHIODH-UHFFFAOYSA-N 2-nonylphenol;oxirane Chemical compound C1CO1.CCCCCCCCCC1=CC=CC=C1O DYBIGIADVHIODH-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 241000530549 Cercospora beticola Species 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 240000004244 Cucurbita moschata Species 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009852 Cucurbita pepo Nutrition 0.000 description 1
- 241000510928 Erysiphe necator Species 0.000 description 1
- 239000005778 Fenpropimorph Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 206010061217 Infestation Diseases 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- 244000237986 Melia azadirachta Species 0.000 description 1
- 235000013500 Melia azadirachta Nutrition 0.000 description 1
- 101100314580 Mus musculus Trim2 gene Proteins 0.000 description 1
- 101150107587 Narf gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000283283 Orcinus orca Species 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 241000682843 Pseudocercosporella Species 0.000 description 1
- 241001281802 Pseudoperonospora Species 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 240000003864 Ulex europaeus Species 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 101100305528 Xenopus laevis rnf138 gene Proteins 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 239000013066 combination product Substances 0.000 description 1
- 229940127555 combination product Drugs 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- CRPOUZQWHJYTMS-UHFFFAOYSA-N dialuminum;magnesium;disilicate Chemical compound [Mg+2].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] CRPOUZQWHJYTMS-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 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 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 235000011475 lollipops Nutrition 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- NWJUMMHVDMNYMJ-UHFFFAOYSA-N n-benzyl-1,1,1-trifluoromethanamine Chemical compound FC(F)(F)NCC1=CC=CC=C1 NWJUMMHVDMNYMJ-UHFFFAOYSA-N 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
- 229920001206 natural gum Polymers 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 244000000003 plant pathogen Species 0.000 description 1
- 238000012809 post-inoculation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- UKHVLWKBNNSRRR-TYYBGVCCSA-M quaternium-15 Chemical compound [Cl-].C1N(C2)CN3CN2C[N+]1(C/C=C/Cl)C3 UKHVLWKBNNSRRR-TYYBGVCCSA-M 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-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
- 238000010792 warming Methods 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso 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
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
-
- 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
- A01N37/52—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 groups, e.g. carboxylic acid amidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11265787A | 1987-10-26 | 1987-10-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26301A true PH26301A (en) | 1992-04-29 |
Family
ID=22345154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH37724A PH26301A (en) | 1987-10-26 | 1988-10-26 | N-phenylalkylbenzamide fungicides |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0314422B1 (es) |
| JP (1) | JPH01151546A (es) |
| KR (1) | KR890006573A (es) |
| CN (1) | CN1033797A (es) |
| AT (1) | ATE92040T1 (es) |
| AU (1) | AU618560B2 (es) |
| BR (1) | BR8805502A (es) |
| CA (1) | CA1301188C (es) |
| DE (1) | DE3882646T2 (es) |
| DK (1) | DK592688A (es) |
| ES (1) | ES2058308T3 (es) |
| HU (1) | HUT49847A (es) |
| IL (1) | IL88133A0 (es) |
| NZ (1) | NZ226693A (es) |
| PH (1) | PH26301A (es) |
| PT (1) | PT88846B (es) |
| SU (1) | SU1760983A3 (es) |
| ZA (1) | ZA887978B (es) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW575562B (en) * | 1998-02-19 | 2004-02-11 | Agrevo Uk Ltd | Fungicides |
| DE19931116A1 (de) * | 1999-07-06 | 2001-01-11 | Bayer Ag | Verfahren zur Herstellung von Phenethylaminen und neue chemische Verbindungen |
| TW200306155A (en) * | 2002-03-19 | 2003-11-16 | Du Pont | Benzamides and advantageous compositions thereof for use as fungicides |
| EP1888535B1 (en) * | 2005-05-03 | 2008-11-19 | Bayer CropScience S.A. | New heterocyclylethylbenzamide derivatives |
| TWI435863B (zh) * | 2006-03-20 | 2014-05-01 | Nihon Nohyaku Co Ltd | Ｎ-２-（雜）芳基乙基甲醯胺衍生物及含該衍生物之蟲害防治劑 |
| WO2007145221A1 (ja) * | 2006-06-13 | 2007-12-21 | Nissan Chemical Industries, Ltd. | 水性懸濁状農薬組成物 |
| US20100063155A1 (en) * | 2007-02-22 | 2010-03-11 | Pierre-Yves Coqueron | N-(3-phenylpropyl)benzamide derivatives |
| BRPI0915387B8 (pt) | 2008-06-26 | 2021-05-25 | Kaken Pharma Co Ltd | agente para a regeneração da membrana timpânica ou canal auditivo externo e uso de uma esponja de gelatina que carrega o fator de crescimento fibroblástico básico e uma cola de fibrina |
| US9447042B2 (en) | 2011-03-02 | 2016-09-20 | The University Of Tokyo | Endoparasite control agent |
| AR092381A1 (es) | 2012-08-30 | 2015-04-15 | Univ Tokyo | Agente de control de endoparasitos y metodo para usarlo |
| JP6218734B2 (ja) | 2012-08-30 | 2017-10-25 | 国立大学法人 東京大学 | 内部寄生虫防除剤 |
| CN102827022A (zh) * | 2012-09-21 | 2012-12-19 | 西华大学 | 2-乙酰氧基-n-(4-甲氧基苯基)苯甲酰胺及其制备方法和用途 |
| JP6410790B2 (ja) | 2013-03-14 | 2018-10-24 | ザ ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティー | ミトコンドリアアルデヒドデヒドロゲナーゼ−２調節因子およびその使用方法 |
| US20160367532A1 (en) | 2014-03-05 | 2016-12-22 | The University Of Tokyo | Endoparasite control agent |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1581075A (es) * | 1968-07-15 | 1969-09-12 | ||
| MC1329A1 (fr) * | 1979-05-17 | 1981-04-21 | Wellcome Found | Aryloxy-et arylamino-alcane-thiocarboxamides,leur preparation et leur application en tant que matieres actives de produits pesticides |
| JPS5758657A (en) * | 1980-09-26 | 1982-04-08 | Showa Denko Kk | N-alpha,alpha-dimethylbenzylamide derivative and herbicide |
| US4835181A (en) * | 1987-02-18 | 1989-05-30 | Eli Lilly And Company | Anticonvulsant agents using cyano dimethylphenyl benzamides |
| DK5489A (da) * | 1988-01-11 | 1989-07-12 | Duphar Int Res | Anvendelse af substituerede amidforbindelser til fremstilling af farmaceutiske praeparater til behandling af haematologiske sygdomme |
-
1988
- 1988-10-24 KR KR1019880013849A patent/KR890006573A/ko not_active Application Discontinuation
- 1988-10-24 IL IL88133A patent/IL88133A0/xx unknown
- 1988-10-25 PT PT88846A patent/PT88846B/pt not_active IP Right Cessation
- 1988-10-25 CA CA000581224A patent/CA1301188C/en not_active Expired - Lifetime
- 1988-10-25 NZ NZ226693A patent/NZ226693A/en unknown
- 1988-10-25 BR BR8805502A patent/BR8805502A/pt not_active Application Discontinuation
- 1988-10-25 ZA ZA887978A patent/ZA887978B/xx unknown
- 1988-10-25 HU HU885583A patent/HUT49847A/hu unknown
- 1988-10-25 ES ES88309998T patent/ES2058308T3/es not_active Expired - Lifetime
- 1988-10-25 AU AU24314/88A patent/AU618560B2/en not_active Ceased
- 1988-10-25 SU SU884356787A patent/SU1760983A3/ru active
- 1988-10-25 DK DK592688A patent/DK592688A/da not_active Application Discontinuation
- 1988-10-25 AT AT88309998T patent/ATE92040T1/de not_active IP Right Cessation
- 1988-10-25 DE DE88309998T patent/DE3882646T2/de not_active Expired - Fee Related
- 1988-10-25 EP EP88309998A patent/EP0314422B1/en not_active Expired - Lifetime
- 1988-10-26 CN CN88107356A patent/CN1033797A/zh active Pending
- 1988-10-26 PH PH37724A patent/PH26301A/en unknown
- 1988-10-26 JP JP63270615A patent/JPH01151546A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01151546A (ja) | 1989-06-14 |
| IL88133A0 (en) | 1989-06-30 |
| DK592688D0 (da) | 1988-10-25 |
| BR8805502A (pt) | 1989-07-04 |
| AU618560B2 (en) | 1992-01-02 |
| DE3882646T2 (de) | 1994-04-28 |
| ES2058308T3 (es) | 1994-11-01 |
| DK592688A (da) | 1989-04-27 |
| CA1301188C (en) | 1992-05-19 |
| KR890006573A (ko) | 1989-06-14 |
| SU1760983A3 (ru) | 1992-09-07 |
| NZ226693A (en) | 1990-12-21 |
| CN1033797A (zh) | 1989-07-12 |
| ZA887978B (en) | 1989-08-30 |
| EP0314422B1 (en) | 1993-07-28 |
| EP0314422A3 (en) | 1991-02-06 |
| PT88846B (pt) | 1993-01-29 |
| ATE92040T1 (de) | 1993-08-15 |
| HUT49847A (en) | 1989-11-28 |
| EP0314422A2 (en) | 1989-05-03 |
| DE3882646D1 (de) | 1993-09-02 |
| AU2431488A (en) | 1989-04-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR0129754B1 (ko) | 퀴나졸린 유도체 | |
| JP3242140B2 (ja) | ジヒドロピリダジノン類および／またはピリダジノン類と殺菌剤との組み合わせ組成物 | |
| PH26301A (en) | N-phenylalkylbenzamide fungicides | |
| US4957533A (en) | N-phenylalkylbenzamide fungicides | |
| DE2734365A1 (de) | Heterocyclische verbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende fungizide zusammensetzungen | |
| US4113465A (en) | Herbicidal formulations | |
| US4250179A (en) | Metal complex imidazole fungicides, and methods of controlling fungi with them | |
| US4013447A (en) | Compositions containing herbicidal thiatriazinone derivatives and use thereof | |
| JPH058161B2 (es) | ||
| AU596436B2 (en) | Novel fungicidal compositions | |
| JPS6270364A (ja) | イミダゾ−ル、それらの調製方法およびそれらの殺菌剤としての用途 | |
| JP2832482B2 (ja) | 殺虫殺菌剤組成物 | |
| US4906650A (en) | N-sulphenylated 2-amino-4-chloro-thiazole-sulphonamides, their use, process for their preparation, and the intermediates 2,4-dichlorothiazole-sulphonyl chloride and 2-amino-4-chloro-thiazole-sulphonamides | |
| WO2021053136A1 (en) | Method for controlling fungus | |
| AU619934B2 (en) | Substituted guanidine and amidine compounds, their production and fungicidal use | |
| US5041154A (en) | Benzoxazine compounds useful as herbicides | |
| CS195717B2 (en) | Herbicide and method of producing the same | |
| US4879314A (en) | Dihaloformaldoxime | |
| US4767446A (en) | Trifluoromethanesulfonanilides, and their production and use | |
| US4213775A (en) | Diphenyl ether derivatives and herbicidal compositions containing the same | |
| JP2901667B2 (ja) | 農園芸用殺菌剤組成物 | |
| AU616223B2 (en) | 2-cyano-2-aryl-1-(azole-1-yl)- ethane derivatives | |
| US4767443A (en) | Antifungal and antibacterial diazine derivatives compositions, intermediates, and method of use therefor | |
| US4228178A (en) | Combating fungi with novel N-sulphenylated carbamoyl compounds | |
| KR810000200B1 (ko) | 아실화 이미다졸일-o, n-아세탈 유도체의 제조방법 |