SK67894A3 - Pyrazole carboxanilide fungicides - Google Patents

Pyrazole carboxanilide fungicides Download PDF

Info

Publication number: SK67894A3
Authority: SK; Slovakia
Prior art keywords: methyl; pyrazole; carboxamide; phenyl; compound
Prior art date: 1991-12-06

Application number

SK678-94A

Other languages

English (en)

Slovak (sk)

Inventor

Jim I Mcloughlin

Suzanne Metz

Original Assignee

Monsanto Co

Priority date (The priority date 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 date listed.)

1991-12-06

Filing date

1992-12-04

Publication date

1995-02-08

1992-12-04 Application filed by Monsanto Co filed Critical Monsanto Co

1995-02-08 Publication of SK67894A3 publication Critical patent/SK67894A3/sk

Links

239000000417 fungicide Substances 0.000 title abstract description 13
WMZYZYFPPQOFKY-UHFFFAOYSA-N n-phenyl-1h-pyrazole-3-carboxamide Chemical compound C1=CNN=C1C(=O)NC1=CC=CC=C1 WMZYZYFPPQOFKY-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 72
239000000203 mixture Substances 0.000 claims abstract description 48
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 45
238000000034 method Methods 0.000 claims abstract description 18
230000000855 fungicidal effect Effects 0.000 claims abstract description 11
-1 methylethyl Chemical group 0.000 claims description 142
239000001257 hydrogen Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims description 6
208000031888 Mycoses Diseases 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
239000002671 adjuvant Substances 0.000 claims description 3
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
125000004970 halomethyl group Chemical group 0.000 claims description 3
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
150000001602 bicycloalkyls Chemical group 0.000 claims 4
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
235000019439 ethyl acetate Nutrition 0.000 description 31
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 22
239000003921 oil Substances 0.000 description 22
235000019198 oils Nutrition 0.000 description 22
239000007787 solid Substances 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
125000001028 difluoromethyl group Chemical class [H]C(F)(F)* 0.000 description 19
239000000047 product Substances 0.000 description 19
235000019441 ethanol Nutrition 0.000 description 18
201000010099 disease Diseases 0.000 description 17
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 17
241000196324 Embryophyta Species 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
229960001866 silicon dioxide Drugs 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000460 chlorine Substances 0.000 description 12
239000000725 suspension Substances 0.000 description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 11
125000004432 carbon atom Chemical group C* 0.000 description 10
230000001629 suppression Effects 0.000 description 10
238000010992 reflux Methods 0.000 description 8
ZVXKYWHJBYIYNI-UHFFFAOYSA-N 1h-pyrazole-4-carboxamide Chemical class NC(=O)C=1C=NNC=1 ZVXKYWHJBYIYNI-UHFFFAOYSA-N 0.000 description 7
238000003556 assay Methods 0.000 description 7
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 7
239000007788 liquid Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
239000005746 Carboxin Substances 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
239000000843 powder Substances 0.000 description 6
241001465180 Botrytis Species 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
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239000004480 active ingredient Substances 0.000 description 5
239000000969 carrier Substances 0.000 description 5
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239000002552 dosage form Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
JHAHAUYJIIKYIC-UHFFFAOYSA-N 1-methylpyrazole-4-carboxamide Chemical compound CN1C=C(C(N)=O)C=N1 JHAHAUYJIIKYIC-UHFFFAOYSA-N 0.000 description 4
FZAUAPKYBFEFKJ-UHFFFAOYSA-N 2-cyclooctylaniline Chemical compound NC1=CC=CC=C1C1CCCCCCC1 FZAUAPKYBFEFKJ-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
241000123650 Botrytis cinerea Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
229910021589 Copper(I) bromide Inorganic materials 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000001448 anilines Chemical class 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
238000011156 evaluation Methods 0.000 description 4
239000006260 foam Substances 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
FZNKJQNEJGXCJH-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound CN1C=C(C(O)=O)C(C(F)(F)F)=N1 FZNKJQNEJGXCJH-UHFFFAOYSA-N 0.000 description 3
ICFGFAUMBISMLR-UHFFFAOYSA-N 1h-pyrazole-5-carbaldehyde Chemical class O=CC=1C=CNN=1 ICFGFAUMBISMLR-UHFFFAOYSA-N 0.000 description 3
241000235349 Ascomycota Species 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
FBWADIKARMIWNM-UHFFFAOYSA-N N-3,5-dichloro-4-hydroxyphenyl-1,4-benzoquinone imine Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1N=C1C=CC(=O)C=C1 FBWADIKARMIWNM-UHFFFAOYSA-N 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
244000061458 Solanum melongena Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
230000009471 action Effects 0.000 description 3
125000004183 alkoxy alkyl group Chemical group 0.000 description 3
125000000304 alkynyl group Chemical group 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
235000021028 berry Nutrition 0.000 description 3
239000012267 brine Substances 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000004927 clay Substances 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 3
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
UYBPRXVMPROPHE-UHFFFAOYSA-N ethyl 1-methyl-3-methylsulfanylpyrazole-4-carboxylate Chemical compound CCOC(=O)C1=CN(C)N=C1SC UYBPRXVMPROPHE-UHFFFAOYSA-N 0.000 description 3
XTHPZTBDQIWSFA-UHFFFAOYSA-N ethyl 5-(difluoromethyl)-1h-pyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NNC=1C(F)F XTHPZTBDQIWSFA-UHFFFAOYSA-N 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
230000007246 mechanism Effects 0.000 description 3
239000002609 medium Substances 0.000 description 3
210000003470 mitochondria Anatomy 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000002689 soil Substances 0.000 description 3
238000009331 sowing Methods 0.000 description 3
239000003643 water by type Substances 0.000 description 3
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
YFUGARBDWJUHFV-UHFFFAOYSA-N 1-(cyclohexylidenemethyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1C=C1CCCCC1 YFUGARBDWJUHFV-UHFFFAOYSA-N 0.000 description 2
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
KWLGFSHSTADSKH-UHFFFAOYSA-N 1h-pyrazole-4-carbonyl chloride Chemical compound ClC(=O)C=1C=NNC=1 KWLGFSHSTADSKH-UHFFFAOYSA-N 0.000 description 2
HKHXJNHHRULHOH-UHFFFAOYSA-N 2-(1-cyclopentylethenyl)aniline Chemical compound NC1=CC=CC=C1C(=C)C1CCCC1 HKHXJNHHRULHOH-UHFFFAOYSA-N 0.000 description 2
NUEWNKNUKRYSLA-UHFFFAOYSA-N 2-(1-cyclopentylideneethyl)aniline Chemical compound C=1C=CC=C(N)C=1C(C)=C1CCCC1 NUEWNKNUKRYSLA-UHFFFAOYSA-N 0.000 description 2
JZOYKZLNRLBDGT-UHFFFAOYSA-N 2-(1-methylcyclopentyl)oxyaniline Chemical compound C=1C=CC=C(N)C=1OC1(C)CCCC1 JZOYKZLNRLBDGT-UHFFFAOYSA-N 0.000 description 2
MUPRNQRVTAMDOU-UHFFFAOYSA-N 2-(cyclohexen-1-yl)aniline Chemical compound NC1=CC=CC=C1C1=CCCCC1 MUPRNQRVTAMDOU-UHFFFAOYSA-N 0.000 description 2
GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
CDEGDZUMZIYNRD-UHFFFAOYSA-N 2-cyclohexylaniline Chemical compound NC1=CC=CC=C1C1CCCCC1 CDEGDZUMZIYNRD-UHFFFAOYSA-N 0.000 description 2
IMBBXSASDSZJSX-UHFFFAOYSA-N 4-Carboxypyrazole Chemical class OC(=O)C=1C=NNC=1 IMBBXSASDSZJSX-UHFFFAOYSA-N 0.000 description 2
KWZDGXNAUOZDOT-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyrazole-4-carboxamide Chemical compound NC(=O)C1=CNN=C1C(F)(F)F KWZDGXNAUOZDOT-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
241000221198 Basidiomycota Species 0.000 description 2
108091003079 Bovine Serum Albumin Proteins 0.000 description 2
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 2
101710088194 Dehydrogenase Proteins 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
241000233866 Fungi Species 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-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
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
241000219094 Vitaceae Species 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
239000011324 bead Substances 0.000 description 2
229920001400 block copolymer Polymers 0.000 description 2
229940098773 bovine serum albumin Drugs 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 2
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
239000013078 crystal Substances 0.000 description 2
150000001925 cycloalkenes Chemical class 0.000 description 2
125000000392 cycloalkenyl group Chemical group 0.000 description 2
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000006622 cycloheptylmethyl group Chemical group 0.000 description 2
WVSCRRLWRRANJY-UHFFFAOYSA-N cyclohexen-1-yl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CCCCC1 WVSCRRLWRRANJY-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
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238000001914 filtration Methods 0.000 description 2
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125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 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
150000002576 ketones Chemical class 0.000 description 2
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 2
UHXMGCKDFJDAHS-UHFFFAOYSA-N n-[2-(1-cyclopentylethyl)phenyl]-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C=1C=CC=C(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)C=1C(C)C1CCCC1 UHXMGCKDFJDAHS-UHFFFAOYSA-N 0.000 description 2
VYYUDVYKOHJJAC-UHFFFAOYSA-N n-[2-(3-bicyclo[2.2.1]heptanyl)phenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carbothioamide Chemical compound FC(F)C1=NN(C)C=C1C(=S)NC1=CC=CC=C1C1C(C2)CCC2C1 VYYUDVYKOHJJAC-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
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238000000746 purification Methods 0.000 description 2
230000000241 respiratory effect Effects 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000011734 sodium Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000001384 succinic acid Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
ROZNFIBJJLDHJM-UHFFFAOYSA-N tert-butyl n-[2-(cyclohexen-1-yl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC=C1C1=CCCCC1 ROZNFIBJJLDHJM-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
235000013311 vegetables Nutrition 0.000 description 2
239000000230 xanthan gum Substances 0.000 description 2
235000010493 xanthan gum Nutrition 0.000 description 2
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238000009736 wetting Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
- C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D233/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
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)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

SK678-94A 1991-12-06 1992-12-04 Pyrazole carboxanilide fungicides SK67894A3 (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US80297891A	1991-12-06	1991-12-06
US87790792A	1992-05-01	1992-05-01
US07/967,417 US5223526A (en)	1991-12-06	1992-11-05	Pyrazole carboxanilide fungicides and use
PCT/US1992/010509 WO1993011117A1 (fr)	1991-12-06	1992-12-04	Fongicides a base de carboxanilide de pyrazole

Publications (1)

Publication Number	Publication Date
SK67894A3 true SK67894A3 (en)	1995-02-08

Family

ID=27419994

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK678-94A SK67894A3 (en)	1991-12-06	1992-12-04	Pyrazole carboxanilide fungicides

Country Status (22)

Country	Link
US (1)	US5223526A (fr)
EP (1)	EP0623113B1 (fr)
JP (1)	JPH07501549A (fr)
CN (1)	CN1078234A (fr)
AR (1)	AR248397A1 (fr)
AT (1)	ATE149490T1 (fr)
AU (1)	AU657598B2 (fr)
BR (1)	BR9206869A (fr)
CA (1)	CA2123122A1 (fr)
CZ (1)	CZ126094A3 (fr)
DE (1)	DE69217997T2 (fr)
HU (1)	HUT67795A (fr)
IL (1)	IL103988A0 (fr)
MD (1)	MD940085A (fr)
MX (1)	MX9207038A (fr)
MY (1)	MY131288A (fr)
NZ (1)	NZ246269A (fr)
SI (1)	SI9200352A (fr)
SK (1)	SK67894A3 (fr)
TR (1)	TR26592A (fr)
WO (1)	WO1993011117A1 (fr)
ZW (1)	ZW18792A1 (fr)

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CN108059614B (zh) *	2016-11-09	2020-09-01	沈阳中化农药化工研发有限公司	吡唑酰胺类化合物及其应用
CN108409684B (zh) *	2018-04-26	2022-04-12	上海晓明检测技术服务有限公司	一种n-(2-环己氧基苯基)酰胺类化合物及其制备方法和应用
CN108383791A (zh) *	2018-04-27	2018-08-10	上海泰禾国际贸易有限公司	一种酰胺类化合物及其制备方法和用途

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1992
- 1992-11-05 US US07/967,417 patent/US5223526A/en not_active Expired - Fee Related
- 1992-12-01 SI SI19929200352A patent/SI9200352A/sl unknown
- 1992-12-04 CA CA002123122A patent/CA2123122A1/fr not_active Abandoned
- 1992-12-04 NZ NZ246269A patent/NZ246269A/en unknown
- 1992-12-04 CZ CZ941260A patent/CZ126094A3/cs unknown
- 1992-12-04 MX MX9207038A patent/MX9207038A/es unknown
- 1992-12-04 JP JP5510373A patent/JPH07501549A/ja active Pending
- 1992-12-04 ZW ZW187/92A patent/ZW18792A1/xx unknown
- 1992-12-04 EP EP93900895A patent/EP0623113B1/fr not_active Expired - Lifetime
- 1992-12-04 AT AT93900895T patent/ATE149490T1/de active
- 1992-12-04 IL IL103988A patent/IL103988A0/xx unknown
- 1992-12-04 MY MYPI92002233A patent/MY131288A/en unknown
- 1992-12-04 WO PCT/US1992/010509 patent/WO1993011117A1/fr not_active Ceased
- 1992-12-04 TR TR92/1170A patent/TR26592A/xx unknown
- 1992-12-04 DE DE69217997T patent/DE69217997T2/de not_active Expired - Fee Related
- 1992-12-04 HU HU9401693A patent/HUT67795A/hu unknown
- 1992-12-04 AU AU32407/93A patent/AU657598B2/en not_active Ceased
- 1992-12-04 AR AR92323828A patent/AR248397A1/es active
- 1992-12-04 SK SK678-94A patent/SK67894A3/sk unknown
- 1992-12-04 BR BR9206869A patent/BR9206869A/pt not_active Application Discontinuation
1993
- 1993-01-02 CN CN93100017A patent/CN1078234A/zh active Pending
- 1993-12-30 MD MD94-0085A patent/MD940085A/ro not_active Application Discontinuation

Also Published As

Publication number	Publication date
AU657598B2 (en)	1995-03-16
CN1078234A (zh)	1993-11-10
MY131288A (en)	2007-07-31
NZ246269A (en)	1995-07-26
IL103988A0 (en)	1993-05-13
EP0623113B1 (fr)	1997-03-05
BR9206869A (pt)	1995-11-28
WO1993011117A1 (fr)	1993-06-10
TR26592A (tr)	1995-03-15
ZW18792A1 (en)	1993-05-12
DE69217997T2 (de)	1997-09-04
CA2123122A1 (fr)	1993-06-10
ATE149490T1 (de)	1997-03-15
MD940085A (ro)	1995-06-30
HU9401693D0 (en)	1994-09-28
HUT67795A (en)	1995-04-28
AR248397A1 (es)	1995-08-18
US5223526A (en)	1993-06-29
DE69217997D1 (de)	1997-04-10
EP0623113A1 (fr)	1994-11-09
AU3240793A (en)	1993-06-28
JPH07501549A (ja)	1995-02-16
MX9207038A (es)	1993-06-01
SI9200352A (en)	1993-06-30
CZ126094A3 (en)	1995-02-15

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JPS62164669A (ja)	1987-07-21	１−アリ−ルピラゾ−ル
JPS6117565A (ja)	1986-01-25	５‐アミノ‐４‐複素環‐１‐フエニルピラゾール
DD144350A5 (de)	1980-10-15	Mittel zur verhuetung von herbizidschaeden an kulturpflanzen
HU183082B (en)	1984-04-28	Fungicide compositions containing alpha-phenoxy-alpha-triazolyl-acetic acid derivatives and process for preparing alpha-phenoxy-alpha-triazolyl-acetic acid derivatives
DE3831430A1 (de)	1990-03-22	Substituierte 4-heterocyclyloximino-pyrazolin-5-one, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel
EP1263734B1 (fr)	2006-09-20	Pesticides 3-thiomethylpyrazoliques
JPH02180866A (ja)	1990-07-13	複素環式置換α―アリール―アクリル酸メチルエステル、ならびに該化合物を含有する殺菌剤および殺虫剤
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JPS62226979A (ja)	1987-10-05	５−アシルアミノ−ピラゾ−ル誘導体
JPS62283961A (ja)	1987-12-09	５−オキシ（チオ）ビラゾ−ル誘導体
US4685957A (en)	1987-08-11	1-aryl-5-iminoaminopyrazoles, compositions containing them, and herbicidal method of using them
DE2828222A1 (de)	1980-01-10	Gegenmittel zum schutz von kulturpflanzen vor schaedigungen durch herbizide
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