JPH0216749B2 - - Google Patents
Info
- Publication number
- JPH0216749B2 JPH0216749B2 JP142684A JP142684A JPH0216749B2 JP H0216749 B2 JPH0216749 B2 JP H0216749B2 JP 142684 A JP142684 A JP 142684A JP 142684 A JP142684 A JP 142684A JP H0216749 B2 JPH0216749 B2 JP H0216749B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrazolidinone
- thiocarbamoyl
- methyl
- chlorophenyl
- hydrogen atom
- Prior art date
- 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
Links
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 29
- -1 1-(2-bromophenyl)thiocarbamoyl-2-(4-chlorophenyl)-3-pyrazolidinone Chemical compound 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 230000001069 nematicidal effect Effects 0.000 claims description 10
- 229910052801 chlorine Chemical group 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- QCBAONYDKCPRBY-UHFFFAOYSA-N n,2-bis(4-chlorophenyl)-3-oxopyrazolidine-1-carbothioamide Chemical compound C1=CC(Cl)=CC=C1NC(=S)N1N(C=2C=CC(Cl)=CC=2)C(=O)CC1 QCBAONYDKCPRBY-UHFFFAOYSA-N 0.000 claims description 6
- GWXVBAJAVWBWDV-UHFFFAOYSA-N n-(4-chlorophenyl)-3-oxo-2-phenylpyrazolidine-1-carbothioamide Chemical compound C1=CC(Cl)=CC=C1NC(=S)N1N(C=2C=CC=CC=2)C(=O)CC1 GWXVBAJAVWBWDV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- BBQCDZIWHBVFPJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(4-ethoxyphenyl)-3-oxopyrazolidine-1-carbothioamide Chemical compound C1=CC(OCC)=CC=C1NC(=S)N1N(C=2C=CC(Cl)=CC=2)C(=O)CC1 BBQCDZIWHBVFPJ-UHFFFAOYSA-N 0.000 claims 4
- DFWODYSZDFWUJC-UHFFFAOYSA-N N-(5-chloro-2-methylphenyl)-2-(4-methylphenyl)-3-oxopyrazolidine-1-carbothioamide Chemical compound C1=CC(C)=CC=C1N1C(=O)CCN1C(=S)NC1=CC(Cl)=CC=C1C DFWODYSZDFWUJC-UHFFFAOYSA-N 0.000 claims 4
- XXSWCNZZOQDZGF-UHFFFAOYSA-N n-(2,5-dichlorophenyl)-2-(4-methylphenyl)-3-oxopyrazolidine-1-carbothioamide Chemical compound C1=CC(C)=CC=C1N1C(=O)CCN1C(=S)NC1=CC(Cl)=CC=C1Cl XXSWCNZZOQDZGF-UHFFFAOYSA-N 0.000 claims 4
- RLUKCRXFQOIHLD-UHFFFAOYSA-N n-(2,5-dichlorophenyl)-4-methyl-3-oxo-2-phenylpyrazolidine-1-carbothioamide Chemical compound O=C1C(C)CN(C(=S)NC=2C(=CC=C(Cl)C=2)Cl)N1C1=CC=CC=C1 RLUKCRXFQOIHLD-UHFFFAOYSA-N 0.000 claims 4
- CLSQVCCVYDRJHA-UHFFFAOYSA-N n-(2-chlorophenyl)-2-(4-chlorophenyl)-3-oxopyrazolidine-1-carbothioamide Chemical compound C1=CC(Cl)=CC=C1N1C(=O)CCN1C(=S)NC1=CC=CC=C1Cl CLSQVCCVYDRJHA-UHFFFAOYSA-N 0.000 claims 4
- QOFGYDZJISORNQ-UHFFFAOYSA-N n-(2-chlorophenyl)-2-(4-methylphenyl)-3-oxopyrazolidine-1-carbothioamide Chemical compound C1=CC(C)=CC=C1N1C(=O)CCN1C(=S)NC1=CC=CC=C1Cl QOFGYDZJISORNQ-UHFFFAOYSA-N 0.000 claims 4
- SLHMLGWBPNNQED-UHFFFAOYSA-N n-(2-chlorophenyl)-4-methyl-3-oxo-2-phenylpyrazolidine-1-carbothioamide Chemical compound O=C1C(C)CN(C(=S)NC=2C(=CC=CC=2)Cl)N1C1=CC=CC=C1 SLHMLGWBPNNQED-UHFFFAOYSA-N 0.000 claims 4
- BUEAOJGGJNOGQU-UHFFFAOYSA-N n-(2-iodophenyl)-4-methyl-3-oxo-2-phenylpyrazolidine-1-carbothioamide Chemical compound O=C1C(C)CN(C(=S)NC=2C(=CC=CC=2)I)N1C1=CC=CC=C1 BUEAOJGGJNOGQU-UHFFFAOYSA-N 0.000 claims 4
- KOACOLFHRGVYMZ-UHFFFAOYSA-N n-(3-bromophenyl)-2-(4-methylphenyl)-3-oxopyrazolidine-1-carbothioamide Chemical compound C1=CC(C)=CC=C1N1C(=O)CCN1C(=S)NC1=CC=CC(Br)=C1 KOACOLFHRGVYMZ-UHFFFAOYSA-N 0.000 claims 4
- GECGHYZZLPKGKI-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(4-chlorophenyl)-3-oxopyrazolidine-1-carbothioamide Chemical compound C1=CC(Cl)=CC=C1N1C(=O)CCN1C(=S)NC1=CC=CC(Cl)=C1 GECGHYZZLPKGKI-UHFFFAOYSA-N 0.000 claims 4
- NLSIDBWIQIGNFA-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(4-methylphenyl)-3-oxopyrazolidine-1-carbothioamide Chemical compound C1=CC(C)=CC=C1N1C(=O)CCN1C(=S)NC1=CC=CC(Cl)=C1 NLSIDBWIQIGNFA-UHFFFAOYSA-N 0.000 claims 4
- BFZWLSJXNXQJFS-UHFFFAOYSA-N n-(4-bromophenyl)-2-(4-chlorophenyl)-3-oxopyrazolidine-1-carbothioamide Chemical compound C1=CC(Cl)=CC=C1N1C(=O)CCN1C(=S)NC1=CC=C(Br)C=C1 BFZWLSJXNXQJFS-UHFFFAOYSA-N 0.000 claims 4
- PAPBUUMADVWKRL-UHFFFAOYSA-N n-(4-bromophenyl)-2-(4-methylphenyl)-3-oxopyrazolidine-1-carbothioamide Chemical compound C1=CC(C)=CC=C1N1C(=O)CCN1C(=S)NC1=CC=C(Br)C=C1 PAPBUUMADVWKRL-UHFFFAOYSA-N 0.000 claims 4
- SRVHQDSZGZLMNG-UHFFFAOYSA-N n-(4-bromophenyl)-4-methyl-3-oxo-2-phenylpyrazolidine-1-carbothioamide Chemical compound O=C1C(C)CN(C(=S)NC=2C=CC(Br)=CC=2)N1C1=CC=CC=C1 SRVHQDSZGZLMNG-UHFFFAOYSA-N 0.000 claims 4
- IYDVOJYBRSLVCL-UHFFFAOYSA-N n-(4-chlorophenyl)-2-(4-methylphenyl)-3-oxopyrazolidine-1-carbothioamide Chemical compound C1=CC(C)=CC=C1N1C(=O)CCN1C(=S)NC1=CC=C(Cl)C=C1 IYDVOJYBRSLVCL-UHFFFAOYSA-N 0.000 claims 4
- IIVMXAIJZGTTNA-UHFFFAOYSA-N n-(4-chlorophenyl)-4-methyl-3-oxo-2-phenylpyrazolidine-1-carbothioamide Chemical compound O=C1C(C)CN(C(=S)NC=2C=CC(Cl)=CC=2)N1C1=CC=CC=C1 IIVMXAIJZGTTNA-UHFFFAOYSA-N 0.000 claims 4
- KOHRJSRDOPFSOO-UHFFFAOYSA-N n-(4-ethoxyphenyl)-2-(4-methylphenyl)-3-oxopyrazolidine-1-carbothioamide Chemical compound C1=CC(OCC)=CC=C1NC(=S)N1N(C=2C=CC(C)=CC=2)C(=O)CC1 KOHRJSRDOPFSOO-UHFFFAOYSA-N 0.000 claims 4
- VDYHFMCUFNUOCT-UHFFFAOYSA-N 5-methyl-3-oxo-n,2-diphenylpyrazolidine-1-carbothioamide Chemical compound CC1CC(=O)N(C=2C=CC=CC=2)N1C(=S)NC1=CC=CC=C1 VDYHFMCUFNUOCT-UHFFFAOYSA-N 0.000 claims 3
- SIYVWPDSRSKXRK-UHFFFAOYSA-N n-(2-bromophenyl)-2-(4-methylphenyl)-3-oxopyrazolidine-1-carbothioamide Chemical compound C1=CC(C)=CC=C1N1C(=O)CCN1C(=S)NC1=CC=CC=C1Br SIYVWPDSRSKXRK-UHFFFAOYSA-N 0.000 claims 3
- DAVPNSGFHZTVQF-UHFFFAOYSA-N n-(3-bromophenyl)-2-(4-chlorophenyl)-3-oxopyrazolidine-1-carbothioamide Chemical compound C1=CC(Cl)=CC=C1N1C(=O)CCN1C(=S)NC1=CC=CC(Br)=C1 DAVPNSGFHZTVQF-UHFFFAOYSA-N 0.000 claims 2
- BITLUVMYPUFZRQ-UHFFFAOYSA-N n-(3-fluorophenyl)-4-methyl-3-oxo-2-phenylpyrazolidine-1-carbothioamide Chemical compound O=C1C(C)CN(C(=S)NC=2C=C(F)C=CC=2)N1C1=CC=CC=C1 BITLUVMYPUFZRQ-UHFFFAOYSA-N 0.000 claims 2
- GZCWYPZKTVIWKC-UHFFFAOYSA-N n-(4-chlorophenyl)-5-methyl-3-oxo-2-phenylpyrazolidine-1-carbothioamide Chemical compound CC1CC(=O)N(C=2C=CC=CC=2)N1C(=S)NC1=CC=C(Cl)C=C1 GZCWYPZKTVIWKC-UHFFFAOYSA-N 0.000 claims 2
- BQVQTBHBHAITPF-UHFFFAOYSA-N 1-methyl-2-phenylpyrazolidin-3-one Chemical compound CN1CCC(=O)N1C1=CC=CC=C1 BQVQTBHBHAITPF-UHFFFAOYSA-N 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 claims 1
- 238000009472 formulation Methods 0.000 description 26
- 239000004480 active ingredient Substances 0.000 description 20
- 239000007788 liquid Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 9
- 241000244206 Nematoda Species 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000969 carrier Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000005645 nematicide Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 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
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 230000008961 swelling Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- KBUPEOGJLVJYOC-UHFFFAOYSA-N 2-(4-chlorophenyl)pyrazolidin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)CCN1 KBUPEOGJLVJYOC-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000013270 controlled release Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- MZZVFXMTZTVUFO-UHFFFAOYSA-N 1-chloro-4-isothiocyanatobenzene Chemical compound ClC1=CC=C(N=C=S)C=C1 MZZVFXMTZTVUFO-UHFFFAOYSA-N 0.000 description 2
- DFJAJOBXRZEBAQ-UHFFFAOYSA-N 2-phenylpyrazolidin-3-one Chemical class O=C1CCNN1C1=CC=CC=C1 DFJAJOBXRZEBAQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 241000243785 Meloidogyne javanica Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical class S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- YQVZREHUWCCHHX-UHFFFAOYSA-N (4-chlorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(Cl)C=C1 YQVZREHUWCCHHX-UHFFFAOYSA-N 0.000 description 1
- BWVQIBKUGHYXLO-UHFFFAOYSA-N 1-(3-methylphenyl)pyrazolidin-3-one Chemical compound CC1=CC=CC(N2NC(=O)CC2)=C1 BWVQIBKUGHYXLO-UHFFFAOYSA-N 0.000 description 1
- LBZPFGXJKJZTRS-UHFFFAOYSA-N 4-methyl-2-phenylpyrazolidin-3-one Chemical compound O=C1C(C)CNN1C1=CC=CC=C1 LBZPFGXJKJZTRS-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241001057636 Dracaena deremensis Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000243786 Meloidogyne incognita Species 0.000 description 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241000193943 Pratylenchus Species 0.000 description 1
- 241000332477 Scutellonema bradys Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 235000001465 calcium Nutrition 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229940060367 inert ingredients Drugs 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-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
- 239000003350 kerosene Substances 0.000 description 1
- 229920005611 kraft lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP142684A JPS60146874A (ja) | 1984-01-10 | 1984-01-10 | 殺線虫性１−（アリ−ル）チオカ−バモイル−２−（アリ−ル）−３−ピラゾリジノン類 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP142684A JPS60146874A (ja) | 1984-01-10 | 1984-01-10 | 殺線虫性１−（アリ−ル）チオカ−バモイル−２−（アリ−ル）−３−ピラゾリジノン類 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60146874A JPS60146874A (ja) | 1985-08-02 |
| JPH0216749B2 true JPH0216749B2 (enrdf_load_stackoverflow) | 1990-04-18 |
Family
ID=11501126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP142684A Granted JPS60146874A (ja) | 1984-01-10 | 1984-01-10 | 殺線虫性１−（アリ−ル）チオカ−バモイル−２−（アリ−ル）−３−ピラゾリジノン類 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60146874A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH053142U (ja) * | 1991-06-28 | 1993-01-19 | 勝弘 斎藤 | 買物用ビニール袋の提手具 |
| JP3029660U (ja) * | 1996-04-01 | 1996-10-01 | 秀和 広瀬 | 荷物及び荷物袋持運び時の、手のひら保護具 |
-
1984
- 1984-01-10 JP JP142684A patent/JPS60146874A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH053142U (ja) * | 1991-06-28 | 1993-01-19 | 勝弘 斎藤 | 買物用ビニール袋の提手具 |
| JP3029660U (ja) * | 1996-04-01 | 1996-10-01 | 秀和 広瀬 | 荷物及び荷物袋持運び時の、手のひら保護具 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60146874A (ja) | 1985-08-02 |
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