JPH0333157B2 - - Google Patents
Info
- Publication number
- JPH0333157B2 JPH0333157B2 JP14547286A JP14547286A JPH0333157B2 JP H0333157 B2 JPH0333157 B2 JP H0333157B2 JP 14547286 A JP14547286 A JP 14547286A JP 14547286 A JP14547286 A JP 14547286A JP H0333157 B2 JPH0333157 B2 JP H0333157B2
- Authority
- JP
- Japan
- Prior art keywords
- linear
- compound
- branched lower
- group
- formula
- 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
- 230000002363 herbicidal effect Effects 0.000 claims description 18
- 239000004009 herbicide Substances 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- LYJBVRVJQXVVPI-UHFFFAOYSA-N 1-thiophen-2-ylethanamine Chemical class CC(N)C1=CC=CS1 LYJBVRVJQXVVPI-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 28
- 241000196324 Embryophyta Species 0.000 description 15
- 239000002689 soil Substances 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 240000003173 Drymaria cordata Species 0.000 description 4
- 241001076438 Oxya japonica Species 0.000 description 4
- 230000000887 hydrating effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGVJVOMCMITTGH-UHFFFAOYSA-N 4-fluoro-n-(1-thiophen-2-ylethyl)benzamide Chemical compound C=1C=CSC=1C(C)NC(=O)C1=CC=C(F)C=C1 QGVJVOMCMITTGH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CYESCLHCWJKRKM-UHFFFAOYSA-N DCPU Natural products NC(=O)NC1=CC=C(Cl)C(Cl)=C1 CYESCLHCWJKRKM-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000208422 Rhododendron Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000009333 weeding Methods 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
- JPMLPXRTVIEZQQ-UHFFFAOYSA-N 3,5-dinitro-n-(1-thiophen-2-ylethyl)benzamide Chemical compound C=1C=CSC=1C(C)NC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 JPMLPXRTVIEZQQ-UHFFFAOYSA-N 0.000 description 1
- QPNBLMWPCLFANK-UHFFFAOYSA-N 4-[[4-(2,4-dichlorobenzoyl)-2,5-dimethylpyrazol-3-yl]methyl]benzenesulfonic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1CC1=CC=C(S(O)(=O)=O)C=C1 QPNBLMWPCLFANK-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- ILOZECIQNMSVCK-UHFFFAOYSA-N 4-methyl-n,n-dipropylaniline Chemical compound CCCN(CCC)C1=CC=C(C)C=C1 ILOZECIQNMSVCK-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 244000301850 Cupressus sempervirens Species 0.000 description 1
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 244000207740 Lemna minor Species 0.000 description 1
- 235000006439 Lemna minor Nutrition 0.000 description 1
- 241000039951 Lithocarpus glaber Species 0.000 description 1
- 108010088249 Monogen Proteins 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- WOZQBERUBLYCEG-UHFFFAOYSA-N SWEP Chemical compound COC(=O)NC1=CC=C(Cl)C(Cl)=C1 WOZQBERUBLYCEG-UHFFFAOYSA-N 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
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003048 aphrodisiac agent Substances 0.000 description 1
- 230000002509 aphrodisiac effect Effects 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- GQDAQMBBGHMTQX-UHFFFAOYSA-N dihydroxy-propylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCSP(O)(O)=S GQDAQMBBGHMTQX-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002063 effect on algae Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- OXHDYFKENBXUEM-UHFFFAOYSA-N glyphosine Chemical compound OC(=O)CN(CP(O)(O)=O)CP(O)(O)=O OXHDYFKENBXUEM-UHFFFAOYSA-N 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- RAIMHFJVWCMCBU-UHFFFAOYSA-N n-(1-thiophen-2-ylethyl)benzamide Chemical compound C=1C=CSC=1C(C)NC(=O)C1=CC=CC=C1 RAIMHFJVWCMCBU-UHFFFAOYSA-N 0.000 description 1
- LKQUCICFTHBFAL-UHFFFAOYSA-N n-benzylbenzamide Chemical class C=1C=CC=CC=1C(=O)NCC1=CC=CC=C1 LKQUCICFTHBFAL-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14547286A JPS632987A (ja) | 1986-06-21 | 1986-06-21 | 新規ｎ−〔１−（チエニル）エチル〕アミン誘導体およびこれを有効成分として含有する除草剤 |
| CN 87108381 CN1033627A (zh) | 1986-06-21 | 1987-12-21 | 新的-n-[1-(噻嗯基)乙基]胺衍生物及含此化合物为有效成份的除草剂 |
| EP19880900125 EP0348505A4 (en) | 1986-06-21 | 1987-12-21 | NOVEL N- (1-THIENYLETHYL) AMINE DERIVATIVES AND HERBICIDES CONTAINING THEM AS ACTIVE INGREDIENTS. |
| PCT/JP1987/001004 WO1989005807A1 (en) | 1986-06-21 | 1987-12-21 | Novel n-(1-thienylethyl)amine derivatives and herbicides containing the same as effective ingredient |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14547286A JPS632987A (ja) | 1986-06-21 | 1986-06-21 | 新規ｎ−〔１−（チエニル）エチル〕アミン誘導体およびこれを有効成分として含有する除草剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS632987A JPS632987A (ja) | 1988-01-07 |
| JPH0333157B2 true JPH0333157B2 (enrdf_load_stackoverflow) | 1991-05-16 |
Family
ID=15386036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14547286A Granted JPS632987A (ja) | 1986-06-21 | 1986-06-21 | 新規ｎ−〔１−（チエニル）エチル〕アミン誘導体およびこれを有効成分として含有する除草剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS632987A (enrdf_load_stackoverflow) |
-
1986
- 1986-06-21 JP JP14547286A patent/JPS632987A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS632987A (ja) | 1988-01-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6141485B2 (enrdf_load_stackoverflow) | ||
| GB1572573A (en) | Organophosphorus herbicidal agents | |
| JPS6127955A (ja) | アリ−ルスルホニル脂肪酸アミド誘導体、その製造法および除草剤 | |
| GB2038814A (en) | Benzamide derivatives and hericidal composition containing the same | |
| JPS62252755A (ja) | 新規ｎ−ベンジルベンズアミド誘導体およびこれを有効成分として含有する除草剤 | |
| JPS6150922B2 (enrdf_load_stackoverflow) | ||
| JPH0333157B2 (enrdf_load_stackoverflow) | ||
| CA1091686A (en) | Thiophosphorylguanidines for combating pests | |
| JPH0655705B2 (ja) | 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 | |
| JPS599521B2 (ja) | 除草剤 | |
| US3832155A (en) | N-alkoxyalkylidenesulfonamide compounds as herbicides | |
| JPS621921B2 (enrdf_load_stackoverflow) | ||
| JPH01186849A (ja) | ジフェニルアミン誘導体、その製造法およびそれを有効成分とする有害生物防除剤 | |
| KR910003713B1 (ko) | 신규의 n-[1-(티에닐)에틸]아민 유도체 및 이 유도체를 활성 성분으로 함유하는 제초제 | |
| JPS585900B2 (ja) | 新規ジフェニルエ−テル系化合物と殺草剤 | |
| US3786048A (en) | Sulfilimine compounds | |
| JPH0368865B2 (enrdf_load_stackoverflow) | ||
| US3909235A (en) | Substituted sulfanilyl sulfilimine compounds as herbicides | |
| JPS62103056A (ja) | アシルアミノブテニルニトリル誘導体、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 | |
| JPH0643422B2 (ja) | 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 | |
| JPH01165503A (ja) | 除草剤組成物 | |
| JPS62255458A (ja) | 新規含フツ素カルボン酸誘導体及びこれを有効成分として含有する除草剤 | |
| JPS6023105B2 (ja) | α，α−ジメチルフエニル酢酸アニリド誘導体、その製造法及びそれを含有する除草剤 | |
| JPS60246352A (ja) | アミド化合物，製造法および除草剤 | |
| JPS60255759A (ja) | アミド置換フルオロ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除草剤および農園芸用殺菌剤 |