CS262676B2 - Fungicide - Google Patents

Fungicide Download PDF

Info

Publication number: CS262676B2
Authority: CS; Czechoslovakia
Prior art keywords: снз; alkyl; compound; formula; hydrogen
Prior art date: 1985-08-31

Application number

CS866312A

Other languages

Czech (cs)

English (en)

Other versions

CS631286A2 (en

Inventor

Hideo Takaishi

Hiroshi Hamaguchi

Akira Nishimura

Kuniaki Taninaka

Original Assignee

Nihon Nohyaku Co Ltd

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.)

1985-08-31

Filing date

1986-08-29

Publication date

1989-03-14

1986-08-29 Application filed by Nihon Nohyaku Co Ltd filed Critical Nihon Nohyaku Co Ltd

1988-08-16 Publication of CS631286A2 publication Critical patent/CS631286A2/cs

1989-03-14 Publication of CS262676B2 publication Critical patent/CS262676B2/cs

Links

230000000855 fungicidal effect Effects 0.000 title claims description 12
239000000417 fungicide Substances 0.000 title description 9
-1 methylenedioxy Chemical group 0.000 claims abstract description 31
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 6
125000003118 aryl group Chemical group 0.000 claims abstract description 5
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
150000002367 halogens Chemical class 0.000 claims abstract description 5
239000000203 mixture Substances 0.000 claims description 25
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
239000004480 active ingredient Substances 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 7
150000003217 pyrazoles Chemical class 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000003944 tolyl group Chemical group 0.000 claims description 3
125000005023 xylyl group Chemical group 0.000 claims description 3
125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims description 2
150000002923 oximes Chemical class 0.000 claims description 2
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 3
125000003545 alkoxy group Chemical group 0.000 abstract description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 37
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
241000209094 Oryza Species 0.000 description 14
235000007164 Oryza sativa Nutrition 0.000 description 14
235000009566 rice Nutrition 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
239000000463 material Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
238000009472 formulation Methods 0.000 description 5
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
230000001105 regulatory effect Effects 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
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CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000002671 adjuvant Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000005507 spraying Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000440 bentonite Substances 0.000 description 3
229910000278 bentonite Inorganic materials 0.000 description 3
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000004927 clay Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
235000013312 flour Nutrition 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000002917 insecticide Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000000376 reactant Substances 0.000 description 3
229960004029 silicic acid Drugs 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
240000007472 Leucaena leucocephala Species 0.000 description 2
235000010643 Leucaena leucocephala Nutrition 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000003905 agrochemical Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000000428 dust Substances 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000003337 fertilizer Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
230000012010 growth Effects 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
230000003902 lesion Effects 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
238000010899 nucleation Methods 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
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239000004033 plastic Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
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239000007787 solid Substances 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical class ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
244000045561 useful plants Species 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
DYGWMDGJMIQAFE-UHFFFAOYSA-N 1,3-dimethyl-5-[3-(trifluoromethyl)phenoxy]pyrazole-4-carbaldehyde Chemical compound CC1=NN(C)C(OC=2C=C(C=CC=2)C(F)(F)F)=C1C=O DYGWMDGJMIQAFE-UHFFFAOYSA-N 0.000 description 1
WCLPDOWYSKMISR-UHFFFAOYSA-N 1,3-dimethyl-5-phenoxypyrazole-4-carbaldehyde Chemical compound CC1=NN(C)C(OC=2C=CC=CC=2)=C1C=O WCLPDOWYSKMISR-UHFFFAOYSA-N 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
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239000005745 Captan Substances 0.000 description 1
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NMKSBNZBSLHAKW-UHFFFAOYSA-N Cl.ClO Chemical compound Cl.ClO NMKSBNZBSLHAKW-UHFFFAOYSA-N 0.000 description 1
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MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
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239000005949 Malathion Substances 0.000 description 1
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MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
239000003245 coal Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
239000010881 fly ash Substances 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000010903 husk Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate 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
UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
239000010871 livestock manure Substances 0.000 description 1
229960000453 malathion Drugs 0.000 description 1
YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
229920000940 maneb Polymers 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
229940043265 methyl isobutyl ketone Drugs 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
NZMAJUHVSZBJHL-UHFFFAOYSA-N n,n-dibutylformamide Chemical compound CCCCN(C=O)CCCC NZMAJUHVSZBJHL-UHFFFAOYSA-N 0.000 description 1
BQVIYHDWJSYSKP-UHFFFAOYSA-N n-[1-(1,3-dimethyl-5-phenoxypyrazol-4-yl)ethylidene]hydroxylamine Chemical compound CC1=NN(C)C(OC=2C=CC=CC=2)=C1C(=NO)C BQVIYHDWJSYSKP-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
239000000123 paper Substances 0.000 description 1
238000005453 pelletization Methods 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
MQHNKCZKNAJROC-UHFFFAOYSA-N phthalic acid dipropyl ester Natural products CCCOC(=O)C1=CC=CC=C1C(=O)OCCC MQHNKCZKNAJROC-UHFFFAOYSA-N 0.000 description 1
239000000419 plant extract Substances 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
239000001205 polyphosphate Substances 0.000 description 1
235000011176 polyphosphates Nutrition 0.000 description 1
239000008262 pumice Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
239000008165 rice bran oil Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000004455 soybean meal Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members

Landscapes

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

CS866312A 1985-08-31 1986-08-29 Fungicide CS262676B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP60192688A JPH0657698B2 (ja)	1985-08-31	1985-08-31	ピラゾ−ルオキシム誘導体及びその製造方法

Publications (2)

Publication Number	Publication Date
CS631286A2 CS631286A2 (en)	1988-08-16
CS262676B2 true CS262676B2 (en)	1989-03-14

Family

ID=16295389

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS866312A CS262676B2 (en)	1985-08-31	1986-08-29	Fungicide

Country Status (5)

Country	Link
JP (1)	JPH0657698B2 (ja)
KR (1)	KR920004933B1 (ja)
CS (1)	CS262676B2 (ja)
ES (1)	ES2001627A6 (ja)
HU (1)	HU200328B (ja)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU611014B2 (en) *	1988-05-06	1991-05-30	Sumitomo Chemical Company, Limited	A pyrazole compound and its production and use
AU616564B2 (en) *	1988-09-29	1991-10-31	Sumitomo Chemical Company, Limited	Novel pyrazole compounds, method for production thereof, use thereof and intermediates for production thereof
JP2018510155A (ja) *	2015-03-19	2018-04-12	イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．ＤｕＰｏｎｔＤｅＮｅｍｏｕｒｓＡｎｄＣｏｍｐａｎｙ	殺菌・殺カビ性ピラゾール
EP4644388A1 (en) *	2022-12-28	2025-11-05	Nippon Soda Co., Ltd.	Five-membered heteroaryl compound and agricultural and horticultural bactericide

1985
- 1985-08-31 JP JP60192688A patent/JPH0657698B2/ja not_active Expired - Lifetime
1986
- 1986-08-29 CS CS866312A patent/CS262676B2/cs not_active IP Right Cessation
- 1986-08-29 ES ES8601512A patent/ES2001627A6/es not_active Expired
- 1986-08-29 HU HU863745A patent/HU200328B/hu not_active IP Right Cessation
- 1986-08-30 KR KR1019860007265A patent/KR920004933B1/ko not_active Expired

Also Published As

Publication number	Publication date
HUT43931A (en)	1988-01-28
HU200328B (en)	1990-05-28
CS631286A2 (en)	1988-08-16
JPS6253969A (ja)	1987-03-09
KR870002081A (ko)	1987-03-30
JPH0657698B2 (ja)	1994-08-03
ES2001627A6 (es)	1988-06-01
KR920004933B1 (ko)	1992-06-22

Legal Events

Date	Code	Title	Description
2000-06-30	IF00	In force as of 2000-06-30 in czech republic
2001-10-17	MK4A	Patent expired	Effective date: 20010829

Publication	Publication Date	Title
US5093364A (en)	1992-03-03	5-fluoroanthranilic fungicides
EP0532022B1 (en)	1995-05-17	Acrylate compound, preparation process thereof and fungicide using the same
EP0104532B1 (en)	1986-12-03	O-halobenzoic acid derivatives, process for their preparation, herbicidal compositions and their use
US4592773A (en)	1986-06-03	Substituted propargyloxyacetonitrile derivatives, process for production thereof, and herbicide and agricultural-horticultural fungicide comprising said derivatives as active ingredients
EP0124154A2 (en)	1984-11-07	Aniline compositions, their preparation, compositions containing them, and method of combating fungus and/or combating or regulating plant growth
US5178663A (en)	1993-01-12	3-alkoxyalkanoic acid derivative, process for preparing the same and herbicide using the same
KR900001196B1 (ko)	1990-02-28	피라졸 유도체의 제조방법
EP0072238B1 (en)	1985-11-06	Pyridazinone derivatives, their preparation and their use in agricultural compositions and the treatment of seed and plants
US5262388A (en)	1993-11-16	Herbicidal compounds
JPH02289559A (ja)	1990-11-29	チアジアゾール置換されたアクリル酸エステル及び中間体
US4221584A (en)	1980-09-09	Herbicidal and plant-growth-regulating N-(heterocyclyl)-methylacetanilides
US4146646A (en)	1979-03-27	Bis-amide fungicidal compounds
EP0185401B1 (en)	1990-06-06	Heterocyclic herbicides
CS262676B2 (en)	1989-03-14	Fungicide
RU2130021C1 (ru)	1999-05-10	Производные пиколинамида, способ их получения, производные пиридин-6-карбонитрила, гербицидная композиция, способ борьбы с нежелательной растительностью
US4072495A (en)	1978-02-07	5-Benzofuranyl esters as herbicides and plant growth regulants
KR920004934B1 (ko)	1992-06-22	피라졸 유도체의 제조방법
JP3110145B2 (ja)	2000-11-20	Ｎ−置換−３−（置換ヒドラジノ）ベンゼンスルホンアミド誘導体、その製造方法及び除草剤
KR890003834B1 (ko)	1989-10-05	치환된 말레이미드의 제조방법
EP0196570B1 (en)	1990-06-13	Benzoaxazine derivatives and herbicidal composition
CS224622B2 (en)	1984-01-16	Microbicide
JP2503547B2 (ja)	1996-06-05	カルバモイルトリアゾ―ル誘導体、その製造法およびそれを有効成分とする除草剤
US4068081A (en)	1978-01-10	Δ-Triazine-2,6-dione
JPH05202038A (ja)	1993-08-10	アゾール誘導体、その製造法およびそれを有効成分とする除草剤
JPH0655705B2 (ja)	1994-07-27	アシルアミノバレロニトリル誘導体、その製造法およびそれらを含有する除草剤および農園芸用殺菌剤