CA1154783A - 3-(n-cycloalkylcarbonyl-n-arylamino)-lactones et thiolactones, agents fongicides - Google Patents

3-(n-cycloalkylcarbonyl-n-arylamino)-lactones et thiolactones, agents fongicides

Info

Publication number: CA1154783A
Authority: CA; Canada
Prior art keywords: carbon atoms; compound; phenyl; methyl; alkyl
Prior art date: 1979-06-01
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000415236A

Other languages

English (en)

Inventor

David C.K. Chan

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chevron USA Inc

Original Assignee

Chevron Research and Technology 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.)

1979-06-01

Filing date

1982-11-09

Publication date

1983-10-04

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

1982-11-09 Application filed by Chevron Research and Technology Co filed Critical Chevron Research and Technology Co

1982-11-09 Priority to CA000415236A priority Critical patent/CA1154783A/fr

1983-10-04 Application granted granted Critical

1983-10-04 Publication of CA1154783A publication Critical patent/CA1154783A/fr

Status Expired legal-status Critical Current

Links

230000000855 fungicidal effect Effects 0.000 title abstract description 20
150000001875 compounds Chemical class 0.000 claims description 51
-1 bromo, hydroxy Chemical group 0.000 claims description 33
125000004432 carbon atom Chemical group C* 0.000 claims description 32
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
125000001309 chloro group Chemical group Cl* 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
241000233866 Fungi Species 0.000 claims description 12
125000001246 bromo group Chemical group Br* 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
238000000034 method Methods 0.000 claims description 9
125000001624 naphthyl group Chemical group 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000001153 fluoro group Chemical group F* 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 6
230000012010 growth Effects 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
241001281803 Plasmopara viticola Species 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
241000233622 Phytophthora infestans Species 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 38
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
239000000047 product Substances 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 20
241000196324 Embryophyta Species 0.000 description 19
239000000417 fungicide Substances 0.000 description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
240000003768 Solanum lycopersicum Species 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
235000007688 Lycopersicon esculentum Nutrition 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000003208 petroleum Substances 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
201000010099 disease Diseases 0.000 description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
240000007087 Apium graveolens Species 0.000 description 7
208000031888 Mycoses Diseases 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000007787 solid Substances 0.000 description 7
235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 6
235000010591 Appio Nutrition 0.000 description 6
206010017533 Fungal infection Diseases 0.000 description 6
241000233679 Peronosporaceae Species 0.000 description 6
235000014787 Vitis vinifera Nutrition 0.000 description 6
239000002585 base Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
241000219095 Vitis Species 0.000 description 5
235000009754 Vitis X bourquina Nutrition 0.000 description 5
235000012333 Vitis X labruscana Nutrition 0.000 description 5
239000002270 dispersing agent Substances 0.000 description 5
238000010828 elution Methods 0.000 description 5
239000012875 nonionic emulsifier Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
231100000167 toxic agent Toxicity 0.000 description 5
239000003440 toxic substance Substances 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
235000010627 Phaseolus vulgaris Nutrition 0.000 description 4
244000046052 Phaseolus vulgaris Species 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000376 reactant Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000002904 solvent 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
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
229940125782 compound 2 Drugs 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
230000007613 environmental effect Effects 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
150000002596 lactones Chemical class 0.000 description 3
244000052769 pathogen Species 0.000 description 3
230000001717 pathogenic effect Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
239000007921 spray Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 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
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 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
241000233614 Phytophthora Species 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
244000061456 Solanum tuberosum Species 0.000 description 2
235000002595 Solanum tuberosum Nutrition 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
229930188620 butyrolactone Natural products 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000000428 dust Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
230000002538 fungal effect Effects 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-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
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
239000002245 particle Substances 0.000 description 2
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000005270 trialkylamine group Chemical group 0.000 description 2
239000000080 wetting agent Substances 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
DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 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
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
241000213004 Alternaria solani Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
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BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
240000007124 Brassica oleracea Species 0.000 description 1
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235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
235000012905 Brassica oleracea var viridis Nutrition 0.000 description 1
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238000009631 Broth culture Methods 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
241000984642 Cura Species 0.000 description 1
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241000221785 Erysiphales Species 0.000 description 1
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239000004606 Fillers/Extenders Substances 0.000 description 1
241000549404 Hyaloperonospora parasitica Species 0.000 description 1
239000007836 KH2PO4 Substances 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
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239000002250 absorbent Substances 0.000 description 1
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150000001340 alkali metals Chemical class 0.000 description 1
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239000001506 calcium phosphate Substances 0.000 description 1
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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
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ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
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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
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235000019796 monopotassium phosphate Nutrition 0.000 description 1
ICCGRYZWPCURPJ-UHFFFAOYSA-N n-(2-methoxyphenyl)-n-(5-oxooxolan-3-yl)cyclopropanecarboxamide Chemical compound COC1=CC=CC=C1N(C(=O)C1CC1)C1CC(=O)OC1 ICCGRYZWPCURPJ-UHFFFAOYSA-N 0.000 description 1
KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
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WOQPIIAJLDWJCH-UHFFFAOYSA-N oxolane-2-thione Chemical compound S=C1CCCO1 WOQPIIAJLDWJCH-UHFFFAOYSA-N 0.000 description 1
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230000035515 penetration Effects 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 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
235000012015 potatoes Nutrition 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000011182 sodium carbonates Nutrition 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
239000002689 soil Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 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
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 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

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)

CA000415236A 1979-06-01 1982-11-09 3-(n-cycloalkylcarbonyl-n-arylamino)-lactones et thiolactones, agents fongicides Expired CA1154783A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000415236A CA1154783A (fr)	1979-06-01	1982-11-09	3-(n-cycloalkylcarbonyl-n-arylamino)-lactones et thiolactones, agents fongicides

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US44,740		1979-06-01
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
US102,793		1979-12-12
CA000353065A CA1147340A (fr)	1979-06-01	1980-05-30	3-(n-acyl-n-arylamino)- et 3-(n-thionoacyl-n-arylamino)-gamma- butyrolactones et gamma-thiobutyro-lactones fongicides
CA000415236A CA1154783A (fr)	1979-06-01	1982-11-09	3-(n-cycloalkylcarbonyl-n-arylamino)-lactones et thiolactones, agents fongicides

Publications (1)

Publication Number	Publication Date
CA1154783A true CA1154783A (fr)	1983-10-04

Family

ID=26721942

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CA000353065A Expired CA1147340A (fr)	1979-06-01	1980-05-30	3-(n-acyl-n-arylamino)- et 3-(n-thionoacyl-n-arylamino)-gamma- butyrolactones et gamma-thiobutyro-lactones fongicides
CA000415236A Expired CA1154783A (fr)	1979-06-01	1982-11-09	3-(n-cycloalkylcarbonyl-n-arylamino)-lactones et thiolactones, agents fongicides
CA000415235A Expired CA1158654A (fr)	1979-06-01	1982-11-09	3-(n-thionoacyl-n-arylamino) lactones et thiolactones fongicides

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CA000353065A Expired CA1147340A (fr)	1979-06-01	1980-05-30	3-(n-acyl-n-arylamino)- et 3-(n-thionoacyl-n-arylamino)-gamma- butyrolactones et gamma-thiobutyro-lactones fongicides

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CA000415235A Expired CA1158654A (fr)	1979-06-01	1982-11-09	3-(n-thionoacyl-n-arylamino) lactones et thiolactones fongicides

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
HU184777B (en)	1984-10-29
SE8004056L (sv)	1980-12-02
IT1148867B (it)	1986-12-03
DK230880A (da)	1980-12-02
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

Legal Events

Date	Code	Title	Description
2000-10-04	MKEX	Expiry

Publication	Publication Date	Title
EP0256503B1 (fr)	1992-12-02	Dérivés de pyridinecarboxamide et leur utilisation comme fongicides
US3933860A (en)	1976-01-20	3-(N-acyl-N-arylamino) lactones
US4672065A (en)	1987-06-09	N-substituted phenoxyacetamide fungicides
KR20010034505A (ko)	2001-04-25	살균제로서 유용한 2-피리딜메틸아민 유도체
US4616004A (en)	1986-10-07	1-iodopropargyl-3,4-disubstituted-Δ2 -1,2,4-triazolidin-5-one fungicides
US4440780A (en)	1984-04-03	Fungicidal 3-(N-acyl-N-arylamino)-and 3-(N-thionoacyl-N-arylamino)-gamma-butyrolactones and gamma-thiobutyrolactones
US5310747A (en)	1994-05-10	Benzimidazole derivatives, agricultural and horticultural fungicides containing the same as an active ingredient and intermediate compounds thereof
US4728669A (en)	1988-03-01	Fungicidal 3-(N-acyl-N-arylamino)-gamma-butyrolactones and gamma-butyrothiolactones
US4504486A (en)	1985-03-12	3-Isoxazolin-5-one fungicides
US4012519A (en)	1977-03-15	Fungicidal 3-(N-acyl-N-arylamino) lactones and lactams
CA1154783A (fr)	1983-10-04	3-(n-cycloalkylcarbonyl-n-arylamino)-lactones et thiolactones, agents fongicides
US4477462A (en)	1984-10-16	Fungicidal 1-methyl-3,4-dihalo-5-alkylthiopyrazoles
US4244959A (en)	1981-01-13	Fungicidal O-acyl (alpha-nitro-formaldoxime) and (alpha-halo-formaldoxime)-pyridines
US4460603A (en)	1984-07-17	1-(2'-Haloalkyl)-amidomethyl-substituted acetanilide fungicides
US4269849A (en)	1981-05-26	Fungicidal 3-(N-cycloalkylcarbonyl-N-arylamino)-gamma-butyrolactones and gamma-butyrothiolactones
US4152460A (en)	1979-05-01	3-Chloro-2,6-dinitro-N-(substituted phenyl)-4-(trifluoromethyl)benzenamines
US4241078A (en)	1980-12-23	Fungicidal 3-(N-acyl-N-arylamino)-gamma-butyrolactones and gamma-butyrothiolactones
US4151279A (en)	1979-04-24	Fungicidal N-carbamyloxy-2,3-disubstituted 4-trihalomethyl-6-oxotetrahydro-1,3-oxazines
GB2046249A (en)	1980-11-12	Fungicidal 3-(N-acyl or thioacyl- N-arylamino)-gamma-butyrolactones and butyrothiolactones
US4382954A (en)	1983-05-10	Fungicidal N-1-substituted cyclopropyl-N-acyl-2,6-dialkylaniline
US4049820A (en)	1977-09-20	Substituted urazole and thiourazole compounds as agricultural fungicidal agents
CA1253517A (fr)	1989-05-02	N-(CARBAMYLMETHYL)-.alpha.-HALOGENO-ACETANILIDES
JPS63150269A (ja)	1988-06-22	置換アミンのサツカリン塩
US4230711A (en)	1980-10-28	Fungicidal n-substituted 4,4-dialkyl homophthalimides
US4599351A (en)	1986-07-08	Fungicidal 3-(N-acyl-N-arylamino) lactones