JPS60146874A - 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 - Google Patents
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Info
- Publication number
- JPS60146874A JPS60146874A JP142684A JP142684A JPS60146874A JP S60146874 A JPS60146874 A JP S60146874A JP 142684 A JP142684 A JP 142684A JP 142684 A JP142684 A JP 142684A JP S60146874 A JPS60146874 A JP S60146874A
- Authority
- JP
- Japan
- Prior art keywords
- pyrazolidinone
- thiocarbamoyl
- methyl
- hydrogen
- chlorophenyl
- 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.)
- Granted
Links
- 230000001069 nematicidal effect Effects 0.000 title claims description 8
- 239000000203 mixture Substances 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 150000002431 hydrogen Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical group 0.000 claims description 11
- 241000244206 Nematoda Species 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- -1 1-(2-bromophenyl)thiocarbamoyl-2-(4-chlorophenyl)-3-pyrazolidinone Chemical compound 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 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 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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
- 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 2
- 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 2
- 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 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
- 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 2
- 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 2
- 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 2
- 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 2
- QHBUOZZTUUIWDA-UHFFFAOYSA-N n-(5-chloro-2-methylphenyl)-4-methyl-3-oxo-2-phenylpyrazolidine-1-carbothioamide Chemical compound O=C1C(C)CN(C(=S)NC=2C(=CC=C(Cl)C=2)C)N1C1=CC=CC=C1 QHBUOZZTUUIWDA-UHFFFAOYSA-N 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 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 1
- 239000000843 powder Substances 0.000 description 38
- 238000009472 formulation Methods 0.000 description 27
- 239000004480 active ingredient Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000007788 liquid Substances 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000969 carrier Substances 0.000 description 7
- 238000002844 melting Methods 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
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- 230000008018 melting Effects 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000011541 reaction mixture 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation 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
- 239000003350 kerosene 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
- 239000000463 material Substances 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
- 239000002245 particle Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 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
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 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
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 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 true JPS60146874A (ja) | 1985-08-02 |
| JPH0216749B2 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) |
Families Citing this family (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
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0216749B2 (enrdf_load_stackoverflow) | 1990-04-18 |
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