HU184777B - Fungicide compositions containing 3-/n-acyl-n-arylamino/- and 3-/n-thionoacyl-n-arylamino/-gamma-butyrolactones and -gamma-thiobutyrolactones - Google Patents

Fungicide compositions containing 3-/n-acyl-n-arylamino/- and 3-/n-thionoacyl-n-arylamino/-gamma-butyrolactones and -gamma-thiobutyrolactones Download PDF

Info

Publication number: HU184777B
Authority: HU; Hungary
Prior art keywords: formula; compound; alkyl; oxygen; hydrogen
Prior art date: 1979-06-01

Application number

HU801365A

Other languages

English (en)

Hungarian (hu)

Inventor

King Chan David Cheong

Original Assignee

Chevron Res

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.)

1979-06-01

Filing date

1980-05-30

Publication date

1984-10-29

1979-06-01 Priority claimed from US06/044,740 external-priority patent/US4440780A/en

1979-12-12 Priority claimed from US06/102,793 external-priority patent/US4269849A/en

1980-05-30 Application filed by Chevron Res filed Critical Chevron Res

1984-10-29 Publication of HU184777B publication Critical patent/HU184777B/hu

Links

230000000855 fungicidal effect Effects 0.000 title claims abstract description 32
239000000203 mixture Substances 0.000 title claims description 52
239000000417 fungicide Substances 0.000 title description 21
150000001875 compounds Chemical class 0.000 claims description 102
-1 hydroxylmethyl Chemical group 0.000 claims description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 40
229910052760 oxygen Inorganic materials 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 28
239000001301 oxygen Substances 0.000 claims description 28
239000004480 active ingredient Substances 0.000 claims description 27
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 27
229910052717 sulfur Inorganic materials 0.000 claims description 27
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
239000011593 sulfur Chemical group 0.000 claims description 23
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
150000002431 hydrogen Chemical class 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
125000001624 naphthyl group Chemical class 0.000 claims description 14
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
239000002518 antifoaming agent Substances 0.000 claims description 3
239000003963 antioxidant agent Substances 0.000 claims description 3
230000003078 antioxidant effect Effects 0.000 claims description 3
239000003945 anionic surfactant Substances 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
125000001309 chloro group Chemical group Cl* 0.000 claims 2
125000004430 oxygen atom Chemical group O* 0.000 claims 2
125000004434 sulfur atom Chemical group 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
125000000129 anionic group Chemical group 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
239000002736 nonionic surfactant Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
239000000047 product Substances 0.000 description 22
239000000243 solution Substances 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 20
241000196324 Embryophyta Species 0.000 description 18
150000002596 lactones Chemical class 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
229910052943 magnesium sulfate Inorganic materials 0.000 description 12
235000019341 magnesium sulphate Nutrition 0.000 description 12
239000003208 petroleum Substances 0.000 description 12
240000003768 Solanum lycopersicum Species 0.000 description 11
239000002270 dispersing agent Substances 0.000 description 11
238000009472 formulation Methods 0.000 description 11
239000000843 powder Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
235000007688 Lycopersicon esculentum Nutrition 0.000 description 9
208000031888 Mycoses Diseases 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
206010017533 Fungal infection Diseases 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000005995 Aluminium silicate Substances 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
235000012211 aluminium silicate Nutrition 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
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 6
239000011541 reaction mixture Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 5
239000012875 nonionic emulsifier Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000002245 particle Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
229920002554 vinyl polymer Polymers 0.000 description 5
239000004563 wettable powder Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
101150065749 Churc1 gene Proteins 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
241000233866 Fungi Species 0.000 description 4
239000005909 Kieselgur Substances 0.000 description 4
102100038239 Protein Churchill Human genes 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
238000004364 calculation method Methods 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
238000002156 mixing Methods 0.000 description 4
WOQPIIAJLDWJCH-UHFFFAOYSA-N oxolane-2-thione Chemical compound S=C1CCCO1 WOQPIIAJLDWJCH-UHFFFAOYSA-N 0.000 description 4
244000052769 pathogen Species 0.000 description 4
239000011550 stock solution Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
240000007087 Apium graveolens Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
241000233679 Peronosporaceae Species 0.000 description 3
241000233622 Phytophthora infestans Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
244000061456 Solanum tuberosum Species 0.000 description 3
235000002595 Solanum tuberosum Nutrition 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
235000008504 concentrate Nutrition 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
230000001717 pathogenic effect Effects 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 2
241000223600 Alternaria Species 0.000 description 2
240000007124 Brassica oleracea Species 0.000 description 2
235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
239000004322 Butylated hydroxytoluene Substances 0.000 description 2
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241000221785 Erysiphales Species 0.000 description 2
241000510928 Erysiphe necator Species 0.000 description 2
206010061217 Infestation Diseases 0.000 description 2
244000046052 Phaseolus vulgaris Species 0.000 description 2
241001281803 Plasmopara viticola Species 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
235000014787 Vitis vinifera Nutrition 0.000 description 2
150000008061 acetanilides Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000004849 alkoxymethyl group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
229960000892 attapulgite Drugs 0.000 description 2
229940095259 butylated hydroxytoluene Drugs 0.000 description 2
235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
235000010216 calcium carbonate Nutrition 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
238000007865 diluting Methods 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000011534 incubation Methods 0.000 description 2
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
239000010410 layer Substances 0.000 description 2
ZCBVLWCRILLHDA-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-n-(5-oxooxolan-3-yl)cyclopropanecarboxamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)C1CC1)C1CC(=O)OC1 ZCBVLWCRILLHDA-UHFFFAOYSA-N 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
229910052625 palygorskite Inorganic materials 0.000 description 2
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
229920002451 polyvinyl alcohol Polymers 0.000 description 2
235000019422 polyvinyl alcohol Nutrition 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000003449 preventive effect Effects 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
125000005270 trialkylamine group Chemical group 0.000 description 2
HZDNNJABYXNPPV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) acetate Chemical compound CC(=O)OCC(Cl)=O HZDNNJABYXNPPV-UHFFFAOYSA-N 0.000 description 1
ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 1
AIYPGRCNJCZMFK-UHFFFAOYSA-N 2-methoxy-n-(2-methylnaphthalen-1-yl)-n-(5-oxooxolan-3-yl)acetamide Chemical compound CC=1C=CC2=CC=CC=C2C=1N(C(=O)COC)C1COC(=O)C1 AIYPGRCNJCZMFK-UHFFFAOYSA-N 0.000 description 1
VNDWQCSOSCCWIP-UHFFFAOYSA-N 2-tert-butyl-9-fluoro-1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one Chemical compound C1=2C=CNC(=O)C=2C2=CC(F)=CC=C2C2=C1NC(C(C)(C)C)=N2 VNDWQCSOSCCWIP-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
OROGUZVNAFJPHA-UHFFFAOYSA-N 3-hydroxy-2,4-dimethyl-2H-thiophen-5-one Chemical compound CC1SC(=O)C(C)=C1O OROGUZVNAFJPHA-UHFFFAOYSA-N 0.000 description 1
JYCQQPHGFMYQCF-UHFFFAOYSA-N 4-tert-Octylphenol monoethoxylate Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCO)C=C1 JYCQQPHGFMYQCF-UHFFFAOYSA-N 0.000 description 1
ZDLBJWZOXYHCPZ-UHFFFAOYSA-N 4-tert-butylsulfanyl-2-[n-(cyclopropanecarbonyl)-2,6-dimethylanilino]butanoic acid Chemical compound CC1=CC=CC(C)=C1N(C(CCSC(C)(C)C)C(O)=O)C(=O)C1CC1 ZDLBJWZOXYHCPZ-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
241000213004 Alternaria solani Species 0.000 description 1
235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
235000010591 Appio Nutrition 0.000 description 1
235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
235000012905 Brassica oleracea var viridis Nutrition 0.000 description 1
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
206010050337 Cerumen impaction Diseases 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
208000015943 Coeliac disease Diseases 0.000 description 1
KMSNYNIWEORQDJ-UHFFFAOYSA-N Dihydro-2(3H)-thiophenone Chemical compound O=C1CCCS1 KMSNYNIWEORQDJ-UHFFFAOYSA-N 0.000 description 1
241000896222 Erysiphe polygoni Species 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241000549404 Hyaloperonospora parasitica Species 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
241000233614 Phytophthora Species 0.000 description 1
235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
235000011613 Pinus brutia Nutrition 0.000 description 1
241000018646 Pinus brutia Species 0.000 description 1
206010035148 Plague Diseases 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
102000001708 Protein Isoforms Human genes 0.000 description 1
108010029485 Protein Isoforms Proteins 0.000 description 1
241000233639 Pythium Species 0.000 description 1
ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
SEQDDYPDSLOBDC-UHFFFAOYSA-N Temazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 SEQDDYPDSLOBDC-UHFFFAOYSA-N 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
241000219094 Vitaceae Species 0.000 description 1
241000219095 Vitis Species 0.000 description 1
235000009754 Vitis X bourquina Nutrition 0.000 description 1
235000012333 Vitis X labruscana Nutrition 0.000 description 1
244000272739 Vitis cinerea Species 0.000 description 1
240000006365 Vitis vinifera Species 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
125000005090 alkenylcarbonyl group Chemical group 0.000 description 1
125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
229930188620 butyrolactone Natural products 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
210000002939 cerumen Anatomy 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000011362 coarse particle Substances 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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 1
WEPUZBYKXNKSDH-UHFFFAOYSA-N cyclopentanecarbonyl chloride Chemical compound ClC(=O)C1CCCC1 WEPUZBYKXNKSDH-UHFFFAOYSA-N 0.000 description 1
ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000000428 dust Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000010685 fatty oil Substances 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
230000002464 fungitoxic effect Effects 0.000 description 1
235000002532 grape seed extract Nutrition 0.000 description 1
235000021021 grapes Nutrition 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000001282 iso-butane Substances 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical group C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
239000004571 lime Substances 0.000 description 1
235000014666 liquid concentrate Nutrition 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
235000011160 magnesium carbonates Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
239000005445 natural material Substances 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
210000002445 nipple Anatomy 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
229920002113 octoxynol Polymers 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
230000035515 penetration Effects 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
239000001965 potato dextrose agar Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
241000894007 species Species 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
238000002255 vaccination Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-membered rings
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms

Landscapes

Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

HU801365A 1979-06-01 1980-05-30 Fungicide compositions containing 3-/n-acyl-n-arylamino/- and 3-/n-thionoacyl-n-arylamino/-gamma-butyrolactones and -gamma-thiobutyrolactones HU184777B (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/044,740 US4440780A (en)	1979-06-01	1979-06-01	Fungicidal 3-(N-acyl-N-arylamino)-and 3-(N-thionoacyl-N-arylamino)-gamma-butyrolactones and gamma-thiobutyrolactones
US06/102,793 US4269849A (en)	1979-02-22	1979-12-12	Fungicidal 3-(N-cycloalkylcarbonyl-N-arylamino)-gamma-butyrolactones and gamma-butyrothiolactones

Publications (1)

Publication Number	Publication Date
HU184777B true HU184777B (en)	1984-10-29

Family

ID=26721942

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU801365A HU184777B (en)	1979-06-01	1980-05-30	Fungicide compositions containing 3-/n-acyl-n-arylamino/- and 3-/n-thionoacyl-n-arylamino/-gamma-butyrolactones and -gamma-thiobutyrolactones

Country Status (14)

Country	Link
AT (1)	AT376427B (fr)
AU (1)	AU543718B2 (fr)
BG (1)	BG36195A3 (fr)
CA (3)	CA1147340A (fr)
DK (1)	DK230880A (fr)
ES (1)	ES492022A0 (fr)
GR (1)	GR68379B (fr)
HU (1)	HU184777B (fr)
IL (1)	IL60158A (fr)
IT (1)	IT1148867B (fr)
PL (1)	PL126303B1 (fr)
PT (1)	PT71339B (fr)
SE (1)	SE8004056L (fr)
YU (2)	YU145580A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4596595A (en) *	1984-06-22	1986-06-24	Chevron Research Company	Herbicidal 5-amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrothiophene and derivatives thereof

1980
- 1980-05-26 IL IL60158A patent/IL60158A/xx unknown
- 1980-05-28 AU AU58844/80A patent/AU543718B2/en not_active Ceased
- 1980-05-28 DK DK230880A patent/DK230880A/da not_active Application Discontinuation
- 1980-05-30 AT AT0289980A patent/AT376427B/de not_active IP Right Cessation
- 1980-05-30 SE SE8004056A patent/SE8004056L/xx not_active Application Discontinuation
- 1980-05-30 YU YU01455/80A patent/YU145580A/xx unknown
- 1980-05-30 HU HU801365A patent/HU184777B/hu unknown
- 1980-05-30 IT IT22452/80A patent/IT1148867B/it active
- 1980-05-30 ES ES492022A patent/ES492022A0/es active Granted
- 1980-05-30 GR GR62080A patent/GR68379B/el unknown
- 1980-05-30 CA CA000353065A patent/CA1147340A/fr not_active Expired
- 1980-05-30 BG BG047973A patent/BG36195A3/xx unknown
- 1980-05-31 PL PL1980224658A patent/PL126303B1/pl unknown
- 1980-06-02 PT PT71339A patent/PT71339B/pt unknown
1982
- 1982-11-09 CA CA000415236A patent/CA1154783A/fr not_active Expired
- 1982-11-09 CA CA000415235A patent/CA1158654A/fr not_active Expired
1983
- 1983-03-15 YU YU00627/83A patent/YU62783A/xx unknown

Also Published As

Publication number	Publication date
YU145580A (en)	1983-10-31
GR68379B (fr)	1981-12-28
ES8105281A1 (es)	1981-05-16
BG36195A3 (en)	1984-09-14
CA1158654A (fr)	1983-12-13
PL126303B1 (en)	1983-07-30
SE8004056L (sv)	1980-12-02
IT1148867B (it)	1986-12-03
DK230880A (da)	1980-12-02
CA1154783A (fr)	1983-10-04
CA1147340A (fr)	1983-05-31
IL60158A0 (en)	1980-07-31
AU543718B2 (en)	1985-05-02
ES492022A0 (es)	1981-05-16
PT71339B (en)	1982-11-15
PL224658A1 (fr)	1981-09-04
YU62783A (en)	1983-10-31
AT376427B (de)	1984-11-26
IL60158A (en)	1986-04-29
ATA289980A (de)	1984-04-15
PT71339A (en)	1980-06-30
IT8022452A0 (it)	1980-05-30
AU5884480A (en)	1980-12-04

Publication	Publication Date	Title
US5093364A (en)	1992-03-03	5-fluoroanthranilic fungicides
EP0532022B1 (fr)	1995-05-17	Composés acryliques, procédé pour leur préparation et fongicides les contenant
KR0145295B1 (ko)	1998-07-15	살균제
US4672065A (en)	1987-06-09	N-substituted phenoxyacetamide fungicides
CS196415B2 (en)	1980-03-31	Fungicide and process for preparing effective compounds
EP0171768B1 (fr)	1988-11-17	Dérivés substitués du propargyloxy-acétonitrile, procédé de leur préparation, herbicides et fongicides pour l'argriculture et pour l'horticulture les contenant comme agents actifs
JPS6097962A (ja)	1985-05-31	１−置換イミダゾ−ル−５−カルボン酸誘導体，それらの製造方法ならびにそれらを含有する殺菌剤，除草剤および植物生長調整剤
US4535087A (en)	1985-08-13	N-Substituted phenoxyacetamide fungicides
US5310747A (en)	1994-05-10	Benzimidazole derivatives, agricultural and horticultural fungicides containing the same as an active ingredient and intermediate compounds thereof
US4144049A (en)	1979-03-13	N-(4-Benzyloxyphenyl)-N-methyl-N-methoxyurea
US4440780A (en)	1984-04-03	Fungicidal 3-(N-acyl-N-arylamino)-and 3-(N-thionoacyl-N-arylamino)-gamma-butyrolactones and gamma-thiobutyrolactones
EP0246507A1 (fr)	1987-11-25	Dérivés du N-cyanoalkylisonicotinamide
US4623377A (en)	1986-11-18	1,2,3,4-tetrahydroquinolin-1-ylcarbonylimidazoles and herbicidal use thereof
US4094985A (en)	1978-06-13	Fungicidal isothiazoles
US4284791A (en)	1981-08-18	Combating fungi with N-chloroacetyl-N-(2,6-di-substituted phenyl)-alanine esters
US4107323A (en)	1978-08-15	Fungicidal 3-(N-acyl-N-arylamino) lactones and lactams
JPS6033396B2 (ja)	1985-08-02	３−（ｎ−アシル−ｎ−アリ−ルアミノ）−ガンマ−ブチロチオラクトン及び該化合物を有効成物とする真菌防除組成物
EP0102163B1 (fr)	1987-04-01	Dérivés de triazole et compositions les contenant
US4460603A (en)	1984-07-17	1-(2'-Haloalkyl)-amidomethyl-substituted acetanilide fungicides
US4504486A (en)	1985-03-12	3-Isoxazolin-5-one fungicides
HU184777B (en)	1984-10-29	Fungicide compositions containing 3-/n-acyl-n-arylamino/- and 3-/n-thionoacyl-n-arylamino/-gamma-butyrolactones and -gamma-thiobutyrolactones
US5120346A (en)	1992-06-09	Substituted tetrazolinones for plant growth inhibition
US4151279A (en)	1979-04-24	Fungicidal N-carbamyloxy-2,3-disubstituted 4-trihalomethyl-6-oxotetrahydro-1,3-oxazines
US4382954A (en)	1983-05-10	Fungicidal N-1-substituted cyclopropyl-N-acyl-2,6-dialkylaniline
US4767446A (en)	1988-08-30	Trifluoromethanesulfonanilides, and their production and use