CS268690B2 - Fungicide - Google Patents

Fungicide Download PDF

Info

Publication number: CS268690B2
Authority: CS; Czechoslovakia
Prior art keywords: compound; plants; methyl; hydrogen; active ingredient
Prior art date: 1986-05-02

Application number

CS873071A

Other languages

Czech (cs)

English (en)

Other versions

CS307187A2 (en

Inventor

Don R Baker

Keith H Brownell

Original Assignee

Stauffer Chemical 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.)

1986-05-02

Filing date

1987-04-30

Publication date

1990-04-11

1987-04-15 Priority claimed from US07/036,542 external-priority patent/US4766134A/en

1987-04-30 Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co

1989-07-12 Publication of CS307187A2 publication Critical patent/CS307187A2/cs

1990-04-11 Publication of CS268690B2 publication Critical patent/CS268690B2/cs

Links

230000000855 fungicidal effect Effects 0.000 title claims abstract description 21
239000000417 fungicide Substances 0.000 title description 10
150000001875 compounds Chemical class 0.000 claims abstract description 41
150000003839 salts Chemical class 0.000 claims abstract description 11
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims description 25
239000004480 active ingredient Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
150000007522 mineralic acids Chemical class 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
239000003701 inert diluent Substances 0.000 claims description 2
125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
150000002825 nitriles Chemical group 0.000 claims 1
-1 CYCLOPROPANE CARBOXAMIDES Chemical class 0.000 abstract description 10
230000002538 fungal effect Effects 0.000 abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 abstract 1
241000196324 Embryophyta Species 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
239000007921 spray Substances 0.000 description 12
238000012360 testing method Methods 0.000 description 12
238000011081 inoculation Methods 0.000 description 11
241000209140 Triticum Species 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
235000021307 Triticum Nutrition 0.000 description 9
239000000843 powder Substances 0.000 description 9
239000000725 suspension Substances 0.000 description 9
201000010099 disease Diseases 0.000 description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
239000002689 soil Substances 0.000 description 8
239000002270 dispersing agent Substances 0.000 description 7
239000003995 emulsifying agent Substances 0.000 description 7
239000007788 liquid Substances 0.000 description 7
230000003449 preventive effect Effects 0.000 description 7
238000009736 wetting Methods 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
240000005979 Hordeum vulgare Species 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
229940125904 compound 1 Drugs 0.000 description 5
230000007423 decrease Effects 0.000 description 5
238000011161 development Methods 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
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238000005507 spraying Methods 0.000 description 5
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101100016026 Drosophila melanogaster GstE14 gene Proteins 0.000 description 4
239000000654 additive Substances 0.000 description 4
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238000010790 dilution Methods 0.000 description 4
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238000011156 evaluation Methods 0.000 description 4
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239000011541 reaction mixture Substances 0.000 description 4
238000010561 standard procedure Methods 0.000 description 4
208000024891 symptom Diseases 0.000 description 4
239000000080 wetting agent Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241001480061 Blumeria graminis Species 0.000 description 3
235000007340 Hordeum vulgare Nutrition 0.000 description 3
240000007594 Oryza sativa Species 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
241000228452 Venturia inaequalis Species 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
230000006378 damage Effects 0.000 description 3
238000000034 method Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
230000001629 suppression Effects 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical class NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
241000123650 Botrytis cinerea Species 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
206010061217 Infestation Diseases 0.000 description 2
244000141359 Malus pumila Species 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000736122 Parastagonospora nodorum Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920001213 Polysorbate 20 Polymers 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
239000004927 clay Substances 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
SGNYPHONOMEXHF-UHFFFAOYSA-N cyclopropene-1-carbonyl chloride Chemical class ClC(=O)C1=CC1 SGNYPHONOMEXHF-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
239000003085 diluting agent Substances 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
239000000428 dust Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
208000014674 injury Diseases 0.000 description 2
239000002054 inoculum Substances 0.000 description 2
230000002262 irrigation Effects 0.000 description 2
238000003973 irrigation Methods 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
239000003350 kerosene Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
239000008096 xylene Substances 0.000 description 2
125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 1
HMFKFHLTUCJZJO-UHFFFAOYSA-N 2-{2-[3,4-bis(2-hydroxyethoxy)oxolan-2-yl]-2-(2-hydroxyethoxy)ethoxy}ethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOCC(OCCO)C1OCC(OCCO)C1OCCO HMFKFHLTUCJZJO-UHFFFAOYSA-N 0.000 description 1
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
235000001674 Agaricus brunnescens Nutrition 0.000 description 1
241000221785 Erysiphales Species 0.000 description 1
206010017533 Fungal infection Diseases 0.000 description 1
241000233866 Fungi Species 0.000 description 1
241000223218 Fusarium Species 0.000 description 1
241000223194 Fusarium culmorum Species 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
208000031888 Mycoses Diseases 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical class OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
241000221300 Puccinia Species 0.000 description 1
241000221301 Puccinia graminis Species 0.000 description 1
241001123569 Puccinia recondita Species 0.000 description 1
206010037888 Rash pustular Diseases 0.000 description 1
241000109463 Rosa x alba Species 0.000 description 1
235000005073 Rosa x alba Nutrition 0.000 description 1
241000109329 Rosa xanthina Species 0.000 description 1
235000004789 Rosa xanthina Nutrition 0.000 description 1
VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 description 1
206010039509 Scab Diseases 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
240000003768 Solanum lycopersicum Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
240000006365 Vitis vinifera Species 0.000 description 1
235000014787 Vitis vinifera Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
MOFCYHDQWIZKMY-UHFFFAOYSA-N chloromethylphosphonic acid Chemical class OP(O)(=O)CCl MOFCYHDQWIZKMY-UHFFFAOYSA-N 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
235000021186 dishes Nutrition 0.000 description 1
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
CWWXKUHOHSBFFZ-UHFFFAOYSA-N dodecanoic acid;n-(6-methoxypyridin-3-yl)cyclopropanecarboxamide Chemical compound CCCCCCCCCCCC(O)=O.C1=NC(OC)=CC=C1NC(=O)C1CC1 CWWXKUHOHSBFFZ-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
235000019674 grape juice Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000007970 homogeneous dispersion Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
239000003621 irrigation water Substances 0.000 description 1
230000003902 lesion Effects 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
239000003595 mist Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
FJZVZSQPGHVJQL-UHFFFAOYSA-N n-(6-methoxypyridin-3-yl)cyclopropanecarbothioamide Chemical compound C1=NC(OC)=CC=C1NC(=S)C1CC1 FJZVZSQPGHVJQL-UHFFFAOYSA-N 0.000 description 1
JPLCQHHISLYGRA-UHFFFAOYSA-N n-(6-methoxypyridin-3-yl)cyclopropanecarboxamide Chemical compound C1=NC(OC)=CC=C1NC(=O)C1CC1 JPLCQHHISLYGRA-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
230000001338 necrotic effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
208000029561 pustule Diseases 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
241000894007 species Species 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000004562 water dispersible granule Substances 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Pyridine Compounds (AREA)

CS873071A 1986-05-02 1987-04-30 Fungicide CS268690B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US85915286A	1986-05-02	1986-05-02
US07/036,542 US4766134A (en)	1987-03-23	1987-04-15	Fungicidal pyridyl cyclopropane carboxamides

Publications (2)

Publication Number	Publication Date
CS307187A2 CS307187A2 (en)	1989-07-12
CS268690B2 true CS268690B2 (en)	1990-04-11

Family

ID=26713255

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS873071A CS268690B2 (en)	1986-05-02	1987-04-30	Fungicide

Country Status (2)

Country	Link
CA (1)	CA1293973C (fr)
CS (1)	CS268690B2 (fr)

1987
- 1987-04-30 CS CS873071A patent/CS268690B2/cs not_active IP Right Cessation
- 1987-05-01 CA CA000536162A patent/CA1293973C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA1293973C (fr)	1992-01-07
CS307187A2 (en)	1989-07-12

Legal Events

Date	Code	Title	Description
2000-06-30	IF00	In force as of 2000-06-30 in czech republic
2001-01-17	MM4A	Patent lapsed due to non-payment of fee	Effective date: 20000430

Publication	Publication Date	Title
EP0243970A1 (fr)	1987-11-04	Imidates de pyridyle fongicides
WO1993019054A1 (fr)	1993-09-30	Nitro-anilines n-heterocycliques utilisees comme fongicides
RO109941B1 (ro)	1995-07-28	Derivati de 4-benzilizoxazol, procedee pentru prepararea acestora, compozitii erbicide si metoda pentru controlul cresterii buruienilor
JP2010538029A (ja)	2010-12-09	新規殺菌剤
US4831044A (en)	1989-05-16	Fungicidal pyridyl cyclopropane carboxamidines
CS236864B2 (en)	1985-05-15	Fungicide agent and processing of active component
JP2006507338A (ja)	2006-03-02	殺真菌剤
US4767771A (en)	1988-08-30	Fungicidal pyridyl imidates
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EP0243972A2 (fr)	1987-11-04	Pyridine cyclopropanecarboximides fongicides
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