JPH044310B2 - - Google Patents

Info

Publication number: JPH044310B2
Authority: JP; Japan
Prior art keywords: group; formula; general formula; morpholino; compound
Prior art date: 1982-05-14
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

JP8007082A

Other languages

English (en)

Japanese (ja)

Other versions

JPS58198472A (ja

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.)

1982-05-14

Filing date

1982-05-14

Publication date

1992-01-27

1982-05-14 Application filed filed Critical

1982-05-14 Priority to JP8007082A priority Critical patent/JPS58198472A/ja

1983-11-18 Publication of JPS58198472A publication Critical patent/JPS58198472A/ja

1992-01-27 Publication of JPH044310B2 publication Critical patent/JPH044310B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 38
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 12
-1 ethyleneimino group Chemical group 0.000 claims description 12
239000004480 active ingredient Substances 0.000 claims description 11
239000000417 fungicide Substances 0.000 claims description 10
125000003277 amino group Chemical group 0.000 claims description 7
230000000855 fungicidal effect Effects 0.000 claims description 7
DDWBEROMBZXLNB-UHFFFAOYSA-N 2,4,6-trichloro-5-methylsulfanylpyrimidine Chemical compound CSC1=C(Cl)N=C(Cl)N=C1Cl DDWBEROMBZXLNB-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
SEYKEMHUCORTTB-UHFFFAOYSA-N 4-chloro-2,6-dimethoxy-5-methylsulfanylpyrimidine Chemical compound COC1=NC(Cl)=C(SC)C(OC)=N1 SEYKEMHUCORTTB-UHFFFAOYSA-N 0.000 claims description 5
IBMKUYMVNFUNOW-UHFFFAOYSA-N 5-methylsulfanylpyrimidine Chemical class CSC1=CN=CN=C1 IBMKUYMVNFUNOW-UHFFFAOYSA-N 0.000 claims description 5
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims 2
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 claims 2
125000004103 aminoalkyl group Chemical group 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
125000004181 carboxyalkyl group Chemical group 0.000 claims 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 15
230000015572 biosynthetic process Effects 0.000 description 14
238000003786 synthesis reaction Methods 0.000 description 13
238000012360 testing method Methods 0.000 description 13
239000002904 solvent Substances 0.000 description 12
239000000243 solution Substances 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
230000003902 lesion Effects 0.000 description 9
238000000034 method Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000007921 spray Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
241000196324 Embryophyta Species 0.000 description 4
241000233866 Fungi Species 0.000 description 4
244000141359 Malus pumila Species 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000004927 clay Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
MXZJUUJULRVWJC-UHFFFAOYSA-N 2,6-dimethoxy-n-methyl-5-methylsulfanylpyrimidin-4-amine Chemical compound CNC1=NC(OC)=NC(OC)=C1SC MXZJUUJULRVWJC-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
241001465180 Botrytis Species 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
244000061456 Solanum tuberosum Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical compound N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
238000005406 washing Methods 0.000 description 3
239000004563 wettable powder Substances 0.000 description 3
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
GWSKXEUCQCCJPS-UHFFFAOYSA-N 2,6-dimethoxy-5-methylsulfanyl-n-phenylpyrimidin-4-amine Chemical compound COC1=NC(OC)=NC(NC=2C=CC=CC=2)=C1SC GWSKXEUCQCCJPS-UHFFFAOYSA-N 0.000 description 2
FOEMIZSFFWGXHX-UHFFFAOYSA-N 2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC=N1 FOEMIZSFFWGXHX-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229940126657 Compound 17 Drugs 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000233622 Phytophthora infestans Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
235000002595 Solanum tuberosum Nutrition 0.000 description 2
WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 2
239000003905 agrochemical Substances 0.000 description 2
238000007605 air drying Methods 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
239000008116 calcium stearate Substances 0.000 description 2
235000013539 calcium stearate Nutrition 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
229940125758 compound 15 Drugs 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
229940126214 compound 3 Drugs 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
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 2
229940079593 drug Drugs 0.000 description 2
238000010410 dusting Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
235000013312 flour Nutrition 0.000 description 2
238000003958 fumigation Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
230000001766 physiological effect Effects 0.000 description 2
244000000003 plant pathogen Species 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000002689 soil Substances 0.000 description 2
238000005507 spraying Methods 0.000 description 2
238000003892 spreading Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
GIKMWFAAEIACRF-UHFFFAOYSA-N 2,4,5-trichloropyrimidine Chemical compound ClC1=NC=C(Cl)C(Cl)=N1 GIKMWFAAEIACRF-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
241000251468 Actinopterygii Species 0.000 description 1
241000235349 Ascomycota Species 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
240000008384 Capsicum annuum var. annuum Species 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
241000221785 Erysiphales Species 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241000692870 Inachis io Species 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
241000233614 Phytophthora Species 0.000 description 1
241001600434 Plectroglyphidodon lacrymatus Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
240000003768 Solanum lycopersicum Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000003945 anionic surfactant Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000005667 attractant Substances 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
238000009739 binding Methods 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
235000013330 chicken meat Nutrition 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
229910052570 clay Inorganic materials 0.000 description 1
230000035613 defoliation Effects 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
150000004659 dithiocarbamates Chemical class 0.000 description 1
GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
244000013123 dwarf bean Species 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
230000012010 growth Effects 0.000 description 1
239000010440 gypsum Substances 0.000 description 1
229910052602 gypsum Inorganic materials 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000007654 immersion Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000002563 ionic surfactant Substances 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
238000002955 isolation Methods 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
229910052622 kaolinite Inorganic materials 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
231100000956 nontoxicity Toxicity 0.000 description 1
239000012053 oil suspension Substances 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000015192 vegetable juice Nutrition 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

JP8007082A 1982-05-14 1982-05-14 ２，４−ジメトキシ−５−メチルチオピリミジン誘導体とその製造法と農園芸用殺菌剤 Granted JPS58198472A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP8007082A JPS58198472A (ja)	1982-05-14	1982-05-14	２，４−ジメトキシ−５−メチルチオピリミジン誘導体とその製造法と農園芸用殺菌剤

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP8007082A JPS58198472A (ja)	1982-05-14	1982-05-14	２，４−ジメトキシ−５−メチルチオピリミジン誘導体とその製造法と農園芸用殺菌剤

Publications (2)

Publication Number	Publication Date
JPS58198472A JPS58198472A (ja)	1983-11-18
JPH044310B2 true JPH044310B2 (hu)	1992-01-27

Family

ID=13707958

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP8007082A Granted JPS58198472A (ja)	1982-05-14	1982-05-14	２，４−ジメトキシ−５−メチルチオピリミジン誘導体とその製造法と農園芸用殺菌剤

Country Status (1)

Country	Link
JP (1)	JPS58198472A (hu)

1982
- 1982-05-14 JP JP8007082A patent/JPS58198472A/ja active Granted

Also Published As

Publication number	Publication date
JPS58198472A (ja)	1983-11-18

Publication	Publication Date	Title
JPH0378383B2 (hu)	1991-12-13
JPS6139941B2 (hu)	1986-09-06
JPH0543706B2 (hu)	1993-07-02
JPH0635450B2 (ja)	1994-05-11	チオシアノピリミジン誘導体、その製造法および農園芸用殺菌剤
JPH044310B2 (hu)	1992-01-27
JPS6345264A (ja)	1988-02-26	新規ピラゾ−ル誘導体、その製造法およびそれらを含有する農園芸用殺菌剤
JPS6229433B2 (hu)	1987-06-25
JPH0543705B2 (hu)	1993-07-02
JPS6237001B2 (hu)	1987-08-10
JPH0373544B2 (hu)	1991-11-22
JPH0410470B2 (hu)	1992-02-25
JP2000103784A (ja)	2000-04-11	５−アルコキシピラゾール−３−カルボキサミド誘導体およびこれを有効成分とする農薬
JPS62106093A (ja)	1987-05-16	Ｎ−（α−シアノフルフリル）ニコチン酸アミド誘導体、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
JP2639428B2 (ja)	1997-08-13	置換テニルスルホンアミド誘導体、その製法及び選択性除草剤
JPH0346469B2 (hu)	1991-07-16
JP2000186089A (ja)	2000-07-04	５−アゾリルピリミジン誘導体、その製法及び農園芸用の殺菌剤
JPH0587067B2 (hu)	1993-12-15
JPS6028967A (ja)	1985-02-14	クロルピリミジン誘導体および農園芸用殺菌剤
JPS60255765A (ja)	1985-12-17	ピロ−ル誘導体、製造法及びそれらを含む除草及び殺菌剤
JPH0759559B2 (ja)	1995-06-28	新規ピラゾ−ル誘導体、その製造法および農園芸用殺菌剤
JPH0655703B2 (ja)	1994-07-27	α−アシルアミノ−（１−シアノエトキシ）アセトニトリル誘導体、その製造法およびそれらを有効成分とする農園芸用殺菌剤
JPH0737449B2 (ja)	1995-04-26	新規ピラゾール誘導体、その製造法および農園芸用殺菌剤
JPH0655704B2 (ja)	1994-07-27	アシルアミノプロピオニトリル誘導体、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
JPS6251673A (ja)	1987-03-06	ジアルコキシチオシアノピリミジン誘導体、その製造法および農園芸用殺菌剤
JPH03261760A (ja)	1991-11-21	ベンジリデンアミノオキシアルカン酸チオアミド誘導体、その製造法及び除草剤