CN100491338C - Substituted amide herbicides - Google Patents
Substituted amide herbicides Download PDFInfo
- Publication number
- CN100491338C CN100491338C CNB03143374XA CN03143374A CN100491338C CN 100491338 C CN100491338 C CN 100491338C CN B03143374X A CNB03143374X A CN B03143374XA CN 03143374 A CN03143374 A CN 03143374A CN 100491338 C CN100491338 C CN 100491338C
- Authority
- CN
- China
- Prior art keywords
- alkyl
- chr
- halo
- compound
- chloro
- 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 - Lifetime
Links
- 150000001408 amides Chemical class 0.000 title abstract description 5
- 239000004009 herbicide Substances 0.000 title description 2
- -1 amide compound Chemical class 0.000 claims abstract description 98
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 241000196324 Embryophyta Species 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000000460 chlorine Substances 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000002585 base Substances 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 230000002363 herbicidal effect Effects 0.000 claims description 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 229910004013 NO 2 Inorganic materials 0.000 claims description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 2
- 230000012010 growth Effects 0.000 claims description 2
- 239000001963 growth medium Substances 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 239000004480 active ingredient Substances 0.000 claims 1
- 240000007594 Oryza sativa Species 0.000 abstract description 7
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 7
- 241000209140 Triticum Species 0.000 abstract description 7
- 235000021307 Triticum Nutrition 0.000 abstract description 7
- 240000008042 Zea mays Species 0.000 abstract description 7
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 7
- 235000005822 corn Nutrition 0.000 abstract description 7
- 235000009566 rice Nutrition 0.000 abstract description 7
- 238000006467 substitution reaction Methods 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- 125000005843 halogen group Chemical group 0.000 description 39
- 125000000217 alkyl group Chemical group 0.000 description 22
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 18
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000001072 heteroaryl group Chemical group 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 description 9
- 239000000470 constituent Substances 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 238000002156 mixing Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000007726 management method Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003217 pyrazoles Chemical class 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- 244000237956 Amaranthus retroflexus Species 0.000 description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- 240000003592 Panicum antidotale Species 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 235000002594 Solanum nigrum Nutrition 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 125000004475 heteroaralkyl group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000002769 thiazolinyl group Chemical group 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 238000009333 weeding Methods 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical class C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- 150000000177 1,2,3-triazoles Chemical class 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 1
- UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VKRGLHLCUMMXHA-UHFFFAOYSA-N 2,3-dihydro-1,3,4-thiadiazole Chemical class C1NN=CS1 VKRGLHLCUMMXHA-UHFFFAOYSA-N 0.000 description 1
- JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 description 1
- CWVHWBUTCVHIGY-UHFFFAOYSA-N 4-propan-2-ylidene-1,3-oxazole Chemical compound CC(C)=C1COC=N1 CWVHWBUTCVHIGY-UHFFFAOYSA-N 0.000 description 1
- DROGIPGCZNKFML-UHFFFAOYSA-N 6-(difluoromethyl)-1-methylcyclohex-3-ene-1,3-dicarboxylic acid Chemical compound FC(C1C(CC(C(=O)O)=CC1)(C(=O)O)C)F DROGIPGCZNKFML-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 240000006928 Persicaria lapathifolia Species 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 244000061457 Solanum nigrum Species 0.000 description 1
- 240000002307 Solanum ptychanthum Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000005277 alkyl imino group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000002243 cyclohexanonyl group Chemical class *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 150000001941 cyclopentenes Chemical class 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000002473 indoazoles Chemical class 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007226 seed germination Effects 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a substituted amide compound as shown in a general formula I. The general formula I compound and a composition thereof can be used for preventing and removing weed in This invention relates to a substitution amide category compound show by general formula I, general formula I compound can be used to prevent and removing weeds in wheat, corn and paddy rice fields. Tfields with wheat, corn and rice. The substituted amide compound also discloses a method for preventing and removing weed for the general formula I compound and the composition thereof. his invention also discloses the application method of general formula I compound and its combination.
Description
Technical field
The invention belongs to the agricultural herbicide field.What relate to is a class new substituted amides and with method of these compound managements of weeds and preparation and the application that contains the herbicidal composition of these compounds.
Background technology
Weeds especially for satisfying agricultural-food such as necessary grain of human primary demand and fiber, are caused very big infringement as cotton, paddy rice, corn, wheat, soybean etc. to crop.The infringement of avoiding when killing or suppressing weed growth or reducing crop is a kind of effective way of improving agriculture production.Although existing many weedicides, but still need more effective, safer weedicide.
The compound general formula following (i) that EUROPEAN PATENT OFFICE announces in EP 0 083 055 A2 on July nineteen eighty-three 6
Wherein:
R
1Be H, alkyl, low cycloalkyl, low cycloalkyl, low alkyl (low) cycloalkyl, low cycloalkyl (low) alkyl, low thiazolinyl, low cycloalkenyl group, low cycloalkenyl group (low) alkyl, phenyl, cyano group (low) alkyl, low alkynyl, low alkyl imino, low alkylthio (low) alkyl, benzyl, halo (low) alkyl or low cycloalkyl imino-;
R
2Be H, low alkyl, low-alkoxy; The X chlorine or bromine; Y is oxygen or imido; Z is oxygen or sulphur.
The compound general formula that EUROPEAN PATENT OFFICE announced among EP 0 273 417 A1 on June 6th, 1988 is (ii) following:
Wherein:
X and Y are H or halogen; Z is-SCH (R) COOR
1
R is H, alkyl; R
1Be alkyl, cycloalkyl, or epoxy alkyl, perhaps Q is an alkyl in COOQ, or Y all links to each other with phenyl ring with Z,
Wherein, R
2Be H or alkyl; R
3Be alkyl; Alkenyl or alkynyl.
More than all reported compound in two pieces of patents with weeding activity.Yet, do not see the report of substituted amide compounds of the present invention.
Summary of the invention
In order to satisfy the requirement on the agricultural, the invention provides a kind of new substituted amide compounds and on agricultural management of weeds application and contain the using method of the weedicide of these compounds.As weedicide, substituted amide compounds provided by the invention can effectively be controlled the weeds in wheat, corn and the rice terrace, and these crops are had security.
Substituted amide compounds structure of the present invention is shown in general formula I:
Wherein: R
1Be H, F, Br, Cl, NO
2Or CN;
R
2Be F, Cl, Br, H or CN;
R
3Be H, CN, CO
2R
3, CONHR
3, CHR
3CO
2R
3, CHR
3CONR
3R
7, NR
3R
7, SO
2NR
3R
7, C
1-C
12Alkyl, ring C
3-C
8Alkyl, C
2-C
12Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
12Alkynyl, halo C
1-C
12Alkyl, halo C
2-C
12Thiazolinyl, halo C
2-C
12Alkynyl, C
1-C
12Alkoxyl group, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl C
1-C
12Alkyl, C
1-C
12Alkyl sulphinyl C
1-C
12Alkyl, C
1-C
12Alkyl sulfonyl basic ring C
3-C
8Alkyl, C
1-C
12Alkyl sulfenyl ring C
3-C
8Alkyl, cyano group C
1-C
12Alkoxyl group, cyano group C
1-C
12Alkyl, cyano group ring C
3-C
8Alkyl, halo C
1-C
12Alkoxyl group, halo C
1-C
12Alkylthio, halo ring C
3-C
8Alkane, aryl or heteroaryl, and these aryl or heteroaryl might be undertaken 1-3 time by following radicals and replace: bromine, chlorine, fluorine, C
1-C
12Alkyl, ring C
3-C
8Alkyl, C
2-C
12Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
12Alkynyl, halo C
1-C
12Alkyl, halo C
2-C
12Thiazolinyl, halo C
2-C
12Alkynyl, C
1-C
12Alkoxyl group, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl, C
1-C
12Alkyl sulphinyl, phenyl, benzene is for C
1-C
12Alkyl, benzene is for C
2-C
12Thiazolinyl, benzene is for C
2-C
12Alkynyl, cyano group, halo C
1-C
12Alkoxyl group, 1,3-dioxan-2-base or nitro;
R
4With R
5Can be identical or different; Be respectively H, CO
2R
3, CONHR
3, CHR
3CO
2R
3, CHR
3CONR
3R
7, halogen, C
1-C
12Alkyl, ring C
3-C
8Alkyl, halo C
1-C
12Alkyl, C
1-C
12Alkoxyl group, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl C
1-C
12Alkyl, C
1-C
12Alkyl sulphinyl C
1-C
12Alkyl, C
1-C
12Alkyl sulfonyl basic ring C
3-C
8Alkyl, C
1-C
12Alkyl sulfenyl basic ring C
3-C
8Alkyl, cyano group C
1-C
12Alkoxyl group, cyanogen is for C
1-C
12Alkyl, cyanogen is for ring C
3-C
8Alkyl, halo C
1-C
12Alkoxyl group, halo C
1-C
12Alkylthio, halo ring C
3-C
8Alkyl, aryl or heteroaryl, and these aryl or heteroaryl might be undertaken 1-3 times by following radicals and replace: bromine, chlorine, fluorine, C
1-C
12Alkyl, ring C
3-C
8Alkyl, C
2-C
12Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
12Alkynyl, halo C
1-C
12Alkyl, halo C
2-C
12Thiazolinyl, halo C
2-C
12Alkynyl, C
1-C
12Alkoxyl group, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl, C
1-C
12Alkyl sulphinyl, phenyl, benzene is for C
1-C
12Alkyl, benzene is for C
2-C
12Thiazolinyl, benzene is for C
2-C
12Alkynyl, cyano group, halo C
1-C
12Alkoxyl group, 1,3-dioxan-2-base or nitro;
R
6Be H, halogen, CN, CO
2R
3, CONR
3R
7, OR
3, SR
3, SO
2R
3, NR
3R
7, SO
2NR
3R
7, C
1-C
12Alkyl, C
1-C
12Alkyl sulphonyl C
1-C
12Alkyl, C
1-C
12Alkyl sulphinyl C
1-C
12Alkyl, C
1-C
12Alkyl sulfonyl basic ring C
3-C
8Alkyl, C
1-C
12Alkyl sulfenyl basic ring C
3-C
8Alkyl, cyanogen is for C
1-C
12Alkoxyl group, cyanogen is for C
1-C
12Alkyl, cyanogen is for ring C
3-C
8Alkyl, halo C
1-C
12Alkoxyl group, halo C
1-C
12Alkylthio, halo ring C
3-C
8Alkyl, aryl or aryl C
1-C
12Alkyl;
R
7Be H, C
1-C
12Alkyl, ring C
3-C
8Alkyl, halo C
1-C
12Alkyl, C
1-C
12Alkyl sulphonyl C
1-C
12Alkyl, C
1-C
12Alkyl sulphinyl C
1-C
12Alkyl, C
1-C
1Alkyl sulfonyl ring C
3-C
8Alkyl, C
1-C
12Alkyl sulfenyl ring C
3-C
8Alkyl, cyanogen is for C
1-C
12Alkoxyl group, cyanogen is for C
1-C
12Alkyl, cyanogen is for ring C
3-C
8Alkyl, halo C
1-C
12Alkoxyl group, halo C
1-C
12Alkylthio, halo ring C
3-C
8Alkyl or COR
3
X-Z is CH=C (halogen), CH
2CH (halogen), CH=C (halogen) CONH, CH
2CH (halogen) CONH;
When X is O, S, NR
7Or CO
2The time, Z is CHR
3Or CHR
3CONH;
Q is Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11 or Q12;
Q1 is 4,5,6,7-tetrahydric phthalimide-2-base,
Q2 is 5,6,7,8-tetrahydrochysene-1,2, and 4-triazole [4,3-a] pyridines-3 (2H)-ketone-1-base,
Q3 is 5,6,7,8-tetrahydrochysene-1H, 3H-[1,3,4] thiadiazoles [3,5-a] pyridazine imines-1-base,
Q4 is 4,5,6,7-tetrahydrochysene-imidazoles [1,5-a] pyridine-1,3 (2H, 5H)-diketone-2-base,
Q5 is 1,6,8-triazole dicyclo [4,3,0]-nonane-7, and 9-diketone-8-base,
Q6 is 5-(1-methyl ethylidene)-2,4-oxazoline diketone-3-base,
Q7 is 5-(1, the 1-dimethyl ethyl)-1,3,4-oxadiazoles-2 (3H)-ketone-3-base,
Q8 is a 4-difluoromethyl-4,5-dihydro-3-methyl isophthalic acid, and 2,4-triazole-5 (1H)-ketone-1-base,
Q9 is 5-methyl-4-(trifluoromethyl)-pyridazine-6H-ketone-1-base,
Q10 is 4-chloro-1-methyl-5-difluoro-methoxy-1H-pyrazole-3-yl,
Q11 is 4-bromo-1-methyl-5-Trifluoromethyl-1 H-pyrazole-3-yl,
Q12 is 1-methyl-6-trifluoromethyl-2,4-pyrimidine dione-3-base;
And the salt that can on agricultural, use.
The structural formula of the above-mentioned ＂ Q ＂ heterocyclic group of mentioning is as follows:
Each substituent definition is expressed as respectively among the present invention:
" alkyl " comprises the alkyl group of side chain and straight chain.Typical alkyl has methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, iso-octyl, nonyl, decyl, undecyl, dodecyl and other.
" cycloalkyl " refers to the compound of fatty family ring structure, as cyclopropane, tetramethylene, pentamethylene, hexanaphthene, suberane, cyclooctane and other.
" haloalkane " refers to the alkyl that is replaced by one or more halogen groups.
" halogen " refers to fluorine, chlorine, bromine or iodine.
" alkyl sulfonyl alkyl " refers to alkyl sulphonyl (alkyl-SO
2) substituted alkyl, as the sulfonyloxy methyl methyl.
" alkyl sulfenyl alkyl " refers to alkyl sulphinyl, and (substituted alkyl of alkyl-SO) is as methyl sulfinyl methyl.
" thiazolinyl " refers to undersaturated hydrocarbon group, contains one or two pair key on the straight or branched.
" cycloalkenyl group " refers to the aliphatics ring and contains one or two pair key, as cyclopentenes, tetrahydrobenzene, and 1,4-tetrahydrobenzene and other.
" haloalkene " refers to one or more halogen substituted alkenyls." alkynyl " refers to undersaturated hydrocarbon group, contains one or two triple bond in the straight or branched.
" aryl " refers to monocycle or polynuclear compound, as benzene, and naphthalene, indenes, anthracene, dicyclopentadiene and, fluorenes, acenaphthene, phenanthrene and azulene to dihydrobenzene.
" heteroaryl " refers to monocycle or polycyclic furans, thiophene, pyrroles, isoxzzole, oxazole, different thiadiazoles, thiazole, pyrazoles, imidazoles, 1,2,3-triazoles, 1,2, the 4-triazole, tetrazolium, 1,2,3-thiadiazoles, 1,2, the 4-thiadiazoles, 1,3,4-thiadiazoles, 1,2, the 3-thiadiazoles, 1,2,4-thiadiazoles, 1,3, the 4-thiadiazoles, pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-tetrazine, cumarone, thionaphthene, indoles, the benzisoxa oxazole, benzoxazoles, benzisothiazole, benzothiazole, benzopyrazoles, benzoglyoxaline, benzotriazole, 1,2-methylenedioxyphenyl, ethylene dioxy base benzene, quinoline and isoquinoline 99.9.
The alkyl that " alkoxyl group " refers in side chain or the straight chain is connected with Sauerstoffatom, and typical alkoxyl group has methoxyl group, oxyethyl group, positive propoxy, isopropoxy, tert.-butoxy and other.
" halogenated alkoxy " refers to one or more halogen atom substituted alkoxies.
The alkyl that " alkylthio " refers in side chain or the straight chain is connected with sulphur atom.
" halogenated alkylthio " refers to one or more halogen atom substituted alkane sulphur bases.
" aralkyl " refers in alkyl group side chain or the straight chain and is called aralkyl by the formed part that contains aryl of aryl replacement.
" heteroaralkyl " refers in alkyl group side chain or the straight chain and is called heteroaralkyl by the formed part that contains heteroaryl of heteroaryl replacement.
The salt of The compounds of this invention is as salt of being formed by organic or inorganic alkali etc.
Among the present invention more preferably compound be, among the general formula compound I:
R
1Be H, F or Cl;
R
2Be Cl;
R
3Be H, CN, CO
2R
3, CONHR
3, CHR
3CO
2R
3, CHR
3CONR
3R
7, NR
3R
7, SO
2NR
3R
7, C
1-C
6Alkyl, ring C
5-C
6Alkyl, C
2-C
6Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
6Alkynyl, halo C
1-C
6Alkyl, halo C
2-C
6Thiazolinyl, halo C
2-C
6Alkynyl, C
1-C
6Alkoxyl group, C
1-C
6Alkylthio, aryl or heteroaryl, wherein aryl or heteroaryl are furans, naphthalene, phenyl, pyrazoles, pyridine, pyrimidine, thiophene or triazole, and might be carried out 1-3 replacement by following radicals: bromine, chlorine, fluorine, C
1-C
12Alkyl, ring C
3-C
8Alkyl, C
2-C
12Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
12Alkynyl, halo C
1-C
12Alkyl, halo C
2-C
12Thiazolinyl, halo C
2-C
12Alkynyl, C
1-C
12Alkoxyl group, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl, C
1-C
12Alkyl sulphinyl, phenyl, benzene is for C
1-C
12Alkyl, benzene is for C
2-C
12Thiazolinyl, benzene is for C
2-C
12Alkynyl, cyano group, halo C
1-C
12Alkoxyl group, 1,3-dioxan-2-base or nitro;
R
4And R
5Be respectively H, CO
2R
3, CONHR
3, CHR
3CO
2R
3, CHR
3CONR
3R
7, bromine, chlorine, fluorine, C
1-C
6Alkyl, ring C
5-C
6Alkyl, halo C
1-C
6Alkyl, C
1-C
6Alkoxyl group, C
1-C
6Alkylthio, aryl, heteroaryl, wherein aryl or heteroaryl are furans, naphthalene, phenyl, pyrazoles, pyridine, pyrimidine, thiophene and triazole, and might be carried out 1-3 replacement by following radicals: bromine, chlorine, fluorine, C
1-C
12Alkyl, ring C
3-C
8Alkyl, C
2-C
12Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
12Alkynyl, halo C
1-C
12Alkyl, halo C
2-C
12Thiazolinyl, halo C
2-C
12Alkynyl, C
1-C
12Alkoxyl group, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl, C
1-C
12Alkyl sulphinyl, phenyl, benzene is for C
1-C
12Alkyl, benzene is for C
2-C
12Thiazolinyl, benzene is for C
2-C
12Alkynyl, cyano group, halo C
1-C
12Alkoxyl group, 1,3-dioxan-2-base or nitro;
R
6Be H, bromine, chlorine, fluorine, CN, CO
2R
3, CONR
3R
7, OR
3, SR
3, SO
2R
3, NR
3R
7, SO
2NR
3R
7, C
1-C
12Alkyl, aryl or aryl C
1-C
6Alkyl, wherein aryl is naphthyl or phenyl;
R
7Be H, C
1-C
12Alkyl, ring C
3-C
8Alkyl, halo C
1-C
12Alkyl or COR
3
X-Z is CH=C (halogen), CH
2CH (halogen), CH=C (halogen) CONH, CH
2CH (halogen) CONH;
When X is O, S, NR
7Or CO
2The time, Z is CHR
3Or CHR
3CONH;
Q is Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11 or Q12;
And by the formed salt that can on agricultural, use of organic or inorganic alkali.
Further preferred compound is among the present invention, among the general formula compound I
R
1Be H, F or Cl;
R
2Be Cl;
R
3Be H, CN, CO
2R
3, CONHR
3, CHR
3CO
2R
3, CHR
3CONR
3R
7, NR
3R
7, SO
2NR
3R
7C
1-C
6Alkyl, ring C
5-C
6Alkyl, C
2-C
6Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
6Alkynyl, halo C
1-C
6Alkyl, halo C
2-C
6Thiazolinyl, halo C
2-C
6Alkynyl, C
1-C
6Alkoxyl group, C
1-C
6Alkylthio, 3-furyl, 4-chloro-2-furyl, 5-chloro-2-furyl, 5-chloro-3-furyl, 2,5-two chloro-3-furyls, 1-naphthyl, 2-naphthyl, phenyl, 4-methylbenzene, 4-p-methoxy-phenyl, the 4-nitrophenyl, 4-fluorophenyl, 4-chloro-phenyl-, the 4-trifluoromethyl, 4-bromophenyl, 4-chloro-phenyl-, the 3-fluorophenyl, 4-Trifluoromethoxyphen-l, 4-benzonitrile base, 3-(1,3-dioxan-2-yl) phenyl, the 2-fluorophenyl, the 2-chloro-phenyl-, 2-Trifluoromethoxyphen-l, 3, the 5-difluorophenyl, 3, the 5-dichlorophenyl, the 2,4 difluorobenzene base, 2, the 5-difluorophenyl, 3-chloro-4-fluorophenyl, 3, the 4-difluorophenyl, 3-chloro-5-trifluoromethyl, 3,4,5-trifluorophenyl, 2-pyridyl, 4-chloro-2-pyridyl, 6-chloro-2-pyridyl, 4,6-two chloro-2-pyridyl, 3-pyridyl, 5-bromo-3-pyridyl, 5,6-two chloro-3-pyridyl, 5-chloro-3-pyridyl, 5-fluoro-3-pyridyl, 4-pyridyl, 2-fluoro-4-pyridyl, 2-chloro-4-pyridyl, 2-chloro-6-methyl-4-pyridyl, 2-methyl-4-pyridyl, 2-methoxyl group-4-pyridyl, 2-cyanogen-4-pyridyl, 2,6-two fluoro-4-pyridyl, 2,6-two chloro-4-pyridyl, the 2-thienyl, the 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl or 2,5-two chloro-3-thienyls;
R
4And R
5Be respectively H, CO
2R
3, CONHR
3, CHR
3CO
2R
3, CHR
3CONR
3R
7, bromine, chlorine, fluorine, C
1-C
6Alkyl, cyanogen is for C
5-C
6Alkyl, halo C
1-C
6Alkyl, C
1-C
6Alkoxyl group, C
1-C
6Alkylthio, 3-furyl, 4-chloro-2-furyl, 5-chloro-2-furyl, 5-chloro-3-furyl, 2,5-two chloro-3-furyls, 1-naphthyl, 2-naphthyl, phenyl, 4-tolyl, 4-p-methoxy-phenyl, the 4-nitrophenyl, 4-fluorophenyl, 4-chloro-phenyl-, the 4-trifluoromethyl, 4-bromophenyl, 4-chloro-phenyl-, the 3-fluorophenyl, 4-Trifluoromethoxyphen-l 4-benzonitrile base, 3-(1,3-dioxan-2-yl) phenyl, 2-fluorophenyl, 2-chloro-phenyl-, the 2-Trifluoromethoxyphen-l, 3, the 5-difluorophenyl, 3,5-dichlorophenyl, 2, the 4-difluorophenyl, 2, the 5-difluorophenyl, 3-chloro-4-fluorophenyl, 3, the 4-difluorophenyl, 3-fluoro-5-Trifluoromethoxyphen-l, 3,4, the 5-trifluorophenyl, 2-pyridyl, 4-chloro-2-pyridyl, 6-chloro-2-pyridyl, 4,6-two chloro-2-pyridyl, the 3-pyridyl, 5-bromo-3-pyridyl, 5,6-two chloro-3-pyridyl, 5-chloro-3-pyridyl, 5-fluoro-3-pyridyl, the 4-pyridyl, 2-fluoro-4-pyridyl, 2--4-pyridyl, 2-chloro-6-methyl-4-pyridyl, 2-methyl-4-pyridyl, 2-methoxyl group-4-pyridyl, 2-cyanogen-4-pyridyl, 2,6-two fluoro-4-pyridyl 2,6-two chloro-4-pyridyl, the 2-thienyl, the 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl or 2,5-two chloro-3-three thienyls;
R
6Be H, bromine, chlorine, fluorine, CN, CO
2R
3, CONR
3R
7, OR
3, SR
3, SO
2R
3, NR
3R
7, SO
2NR
3R
7, C
1-C
6Alkyl, 1-naphthyl, 2-naphthyl, phenyl, the 4-aminomethyl phenyl, 4-p-methoxy-phenyl, 4-nitrophenyl, 4-fluorophenyl, the 4-chloro-phenyl-, 4-trifluoromethyl, 4-bromophenyl, 4-chloro-phenyl-, the 3-fluorophenyl, 4-Trifluoromethoxyphen-l, 4-cyanogen are for phenyl, and 3-(1,3-dioxan-2-yl) phenyl, 2-fluorophenyl, 2-chloro-phenyl-, the 2-Trifluoromethoxyphen-l, 3, the 5-difluorophenyl, 3,5-dichlorophenyl, 2, the 4-difluorophenyl, 2, the 5-difluorophenyl, 3-chloro-4-fluorophenyl, 3, the 4-difluorophenyl, 3-fluoro-5-trifluoromethyl or 3,4, the 5-trifluorophenyl;
R
7Be H, C
1-C
6Alkyl, ring C
3-C
8Alkyl, halo C
1-C
6Alkyl and COR
3
When X was O or S, Z was CHR
3
Q is Q1, Q3, Q8, Q9, Q10, Q11 or Q12;
And form sodium salt, sylvite, triethylamine salt or the pyridinium salt that on agricultural, to use by organic or inorganic alkali.
The further preferred compound of the present invention is, among the general formula compound I
R
1Be F;
R
2Be Cl;
R
3Be H;
R
4And R
5Be respectively H or C
1-C
6Alkyl;
R
6Be CN or CO
2C
2H
5
X is O;
Z is CH
2
Q is Q
1
Compound of Formula I of the present invention can prepare by following method:
Method 1, reaction formula is as follows:
Among above-mentioned intermediate II and the III, X is O, S, NR
7Or CO
2Z is CH (R
3), CH (R
3) CONH; Y is Br, Cl, CH
3SO
3Or 4-CH
3C
6H
5SO
3, other substituting groups as previously mentioned.With chloroform, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, tetrahydrofuran (THF), dioxane, acetone or butanone are solvent, under alkaline condition, as triethylamine, pyridine, NaOH, KOH, Na
2CO
3, K
2CO
3Or NaHCO
3Exist down, control reaction temperature was reacted 30 minutes-8 hours at-40 ℃～reaction solution reflux temperature, can generate the represented compound of general formula I.
Intermediate II can be made by currently known methods.
Intermediate III can make by following known response:
Method 2, reaction formula is as follows:
In the intermediate compound IV, X-Z is CH=C (halogen), CH
2CH (halogen), CH=C (halogen) CONH or CH
2CH (halogen) CONH; M is COCl; Or X-Z-M is CH=C (halogen) COCl, CH
2CH (halogen) COCl, CH=C (halogen) CONCO or CH
2CH (halogen) CONCO; Other substituting groups as previously mentioned.
Intermediate compound IV is at solvent such as methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, tetrahydrofuran (THF), dioxane, in ethyl acetate, acetone or the butanone with intermediate V reaction, at alkali such as triethylamine, pyridine, NaOH, KOH, Na
2CO
3, K
2CO
3Or NaHCO
3Exist down, control reaction temperature was reacted 5 minutes-8 hours at-40 ℃～reaction solution reflux temperature, got the represented compound of general formula I.
The compound of part general formula I sees Table 1.In these tables, " Pri " represents sec.-propyl, and ＂ Ph ＂ represents phenyl, and ＂ Ph-4-Cl ＂ represents the 4-chloro-phenyl-, ＂ CH
2Ph ＂ represents benzyl, ＂ CH
2Ph-4-Cl ＂ represents 4-benzyl chloride base, and ＂ 3-Py ＂ represents the 3-pyridyl, and 2-FUR represents the 2-furyl.
Table 1
The present invention also comprises by general formula I represented substituted amide compounds with weeding activity and the agriculture formed herbicidal composition of applicable carrier of.
Other embodiments of the present invention are that prevention target crop field is (as wheat, corn and paddy rice) in method for weed, this method comprises that the substituted amide class herbicidal composition with compound shown in the general formula I of herbicidally effective amount and acceptable carrier composition imposes on the surface of growth medium of the places of described weeds, described weeds or described weeds.
The expressed compound of general formula I is useful as the effective constituent of weedicide.When the compound of general formula I of the present invention during as weedicide, the formulation that effective constituent is fit to depends on specific purposes and suitable application process.In general, effective constituent is dissolved or dilution with inert solvent or solid carrier, and applied formulation has pulvis, wettable powder, and missible oil, aqua and oil suspending agent, granula, capsules etc. need to add tensio-active agent and other auxiliary agent usually.In these weedicides, acceptable inert thinner or tensio-active agent such as solid carrier or liquid vehicle are mixed on the agricultural of activeconstituents and routine.Carrier not only can dissolve, disperse effective constituent but also not influence the activity of effective constituent, and itself does not have the obvious damage effect to soil, equipment, crop or agricultural environment.Auxiliary agent is generally tensio-active agent, stablizer, defoamer or dispersion agent.Weedicide of the present invention comprises that also its purpose is to enlarge the field of activity of preparation and improves drug effect with being mixed of known agricultural chemical compound.For example The compounds of this invention can with sterilant, nematocides, sterilant and other weedicide, plant-growth regulator, fertilizer etc. are used with.
Active constituent content in the preparation (weight percentage) from 0.1% to 95%, and contain at least 0.1% to 20% tensio-active agent and 1% to 99% solid or liquid diluent.
The effective dosage ranges of The compounds of this invention is generally the 1g/ hectare to the 3kg/ hectare, suitable effective dosage ranges for the 5g/ hectare to the 500g/ hectare.
Substituted amide compounds of the present invention and composition thereof have the effect of fabulous management of weeds, can effectively prevent and kill off multiple weeds in farm crop Tanaka, particularly wheat, corn and the rice terrace, and to these crop safeties.
Embodiment
Below with the preparation and examples of formulations the present invention will be described in more detail.But should point out that the present invention never only limits to these concrete examples.In the example of preparation, " part " expression parts by weight, consistent in compound number and the table 1.
Preparation example 1 (No. 1 compound)
2-(4-chloro-2-fluoro-5-hydroxy phenyl)-4,5,6,7-tetrahydrochysene-2H-isoindole-1,3-diketone 0.5 gram (making), 0.4 gram K by the method among EP 0 083 055 A2
2CO
3With 0.8 gram bromoacetamide guanidine-acetic acid ethyl ester reflux 8 hours in the 50ml butanone, after the cooling, to filter, filtrate concentrates.Add water and ethyl acetate in the residuum, tell organic layer, and water and salt water washing, dry back concentrates.Residuum gets 0.6 gram object with purification by silica gel column chromatography, and fusing point is 142～145 ℃.
1H?NMR(300MHz，CDCl
3)：7.31(d，1H)，6.82(d，1H)，4.55(s，2H)，4.24(t，2H)，4.15(d，2H)，2.43(bs，4H)，1.83(bs，4H)，1.28(q，3H)。
Preparation example 2 (No. 15 compound)
2-(4-chloro-2-fluoro-5-hydroxy phenyl)-4,5,6,7-tetrahydrochysene-2H-isoindole-1,3-diketone 0.5 gram (making), 0.3 gram K by the method among EP 0 083 055 A2
2CO
3With 0.4 gram acetobrom amido acetonitrile reflux 8 hours in the 50ml butanone, after the cooling, to filter, filtrate concentrates.Add water and ethyl acetate in the residuum, tell organic layer, and water and salt water washing, dry back concentrates.Residuum gets 0.58 gram object with purification by silica gel column chromatography, and fusing point is 206～208 ℃.
1HNMR(300MHz，CDCl
3)：7.35(d，1H)，6.81(d，1H)，4.57(s，2H)，4.31(t，2H)，2.43(bs，4H)，1.83(bs，4H)。
Preparation example 3 (No. 22 compound)
2-(4-chloro-2-fluoro-5-hydroxy phenyl)-4,5,6,7-tetrahydrochysene-2H-isoindole-1,3-diketone 0.5 gram (making), 0.3 gram K by the method among EP 0 083 055 A2
2CO
3The bromoacetamide that replaces with 0.5 gram reflux 4 hours in the 50ml butanone after the cooling, is filtered, and filtrate concentrates.Add water and ethyl acetate in the residuum, tell organic layer, and water and salt water washing, dry back concentrates.Residuum gets 0.44 gram object with purification by silica gel column chromatography, and fusing point is 139～143 ℃.
1H?NMR(300MHz，CDCl
3)：7.32(d，1H)，6.95(bs，1H)，6.81(d，1H)，4.51(s，2H)，2.44(bs，4H)，2.40(m，1H)，1.83(bs，4H)，1.71(s，3H)，1.18(d，3H)，1.12(d，3H)。
The synthetic method of other compounds is the same in the table 1.
Formulation examples 1a-c
Take by weighing 50 parts of the 1st, 15, No. 22 compounds respectively, 5 parts of polyoxyethylene alkane aryl oxides, 5 parts of pelopon A parts, 40 parts of levigate and abundant mixings of artificial hydrated SiO 2 promptly get 50% wettable powder.
Formulation examples 2
10 parts of No. 1 compounds, 6 parts of polyoxyethylene alkane aryl oxides, 4 parts of pelopon As, 50 parts of 30 parts of dimethylbenzene and cyclohexanones, fully mixing dissolving promptly gets 10% missible oil.
Formulation examples 3
20 parts of No. 1 compounds, 2 parts of artificial hydrated SiO 2s, 3 parts of the pure monooleates of polyoxyethylene dehydration sorb (sugar), 5 parts of carboxymethyl celluloses are levigate and and 70 parts of abundant mixings of water, and make the effective constituent particle less than 5 microns, promptly get 20% water suspending agent.
Formulation examples 4
5 parts of No. 1 compounds, 1 part of isopropyl acid phosphoric acid salt, 64 parts and 30 parts levigate and abundant mixings of talcum powder of kaolin, and make the effective constituent particle less than 5 microns, promptly get 5% pulvis.
Formulation examples 5
25 parts of No. 1 compounds, 3 parts of the pure monooleates of polyoxyethylene dehydration sorb (sugar), 2 parts of polyvinyl alcohol are levigate and and 70 parts of abundant mixings of water, and the effective constituent particle promptly gets 25% water suspending agent less than 5 microns.
Biological assay
With weeds Amaranthus retroflexus (Amaranthus retroflexus), black nightshade (Solanum nigrum), Herb polygoni Lapathifolii (Polygonumlapathifolium), piemarker (Abutilon theophrasti), Panicum antidotale (PA) and crop such as wheat, corn, paddy rice, soybean and cotton are measured this compound.
According to follow procedure each compound is measured.
Measure behind the seedling, seed germination also grew 10-21 days, made the examination material that has a series of growing stages before the processing, selected size, the consistent examination material of growing stage then, handled, and handled to place the greenhouse and water.The examination material with compound treatment does not compare.
Testing compound dissolves with suitable solvent (generally using acetone), and its preparation is directly used water dissolution, the processing of spraying then, and spouting liquid is 187 or 468 liters/hectare, dosage is gram/hectare.2 weeks or the investigation of 4 weeks after processing, with 0-100 classifications, 0 represents non-activity to medicament to each activity of trying material, 100 expressions suppress fully.Partial test the results are shown in Table 4 and 5:
Table 4
Table 5
Claims (7)
1, substituted amide compounds, shown in general formula I:
Wherein:
R
1Be H, F, Br, Cl, NO
2Or CN;
R
2Be F, Cl, Br, H or CN;
R
3Be H, CN, CO
2R
3, CONHR
3, CHR
3CO
2R
3, CHR
3CONR
3R
7, C
1-C
6Alkyl or halo C
1-C
6Alkyl;
R
4And R
5Can be identical or different, be respectively H, CO
2R
3, CONHR
3, CHR
3CO
2R
3, CHR
3CONR
3R
7, halogen, C
1-C
6Alkyl, halo C
1-C
6Alkyl, C
1-C
6Alkoxyl group or C
1-C
6Alkylthio;
R
6Be H, halogen, CN, CO
2R
3, CONR
3R
7, OR
3, SR
3, SO
2R
3, NR
3R
7, SO
2NR
3R
7Or C
1-C
6Alkyl;
R
7Be H, C
1-C
6Alkyl, halo C
1-C
6Alkyl or COR
3
X-Z is CH=C (halogen) or CH
2CH (halogen);
When X is O, S, NR
7Or CO
2The time, Z is CHR
3Or CHR
3CONH;
Q is Q1, that is: 4,5,6, and 7-tetrahydric phthalimide-2-base;
And on agricultural applicable salt.
2, according to the described compound of claim 1, it is characterized in that: among the general formula compound I
R
1Be H, F or Cl;
R
2Be Cl;
R
3Be H, CN, CO
2R
3, CONHR
3, CHR
3CO
2R
3, CHR
3CONR
3R
7, C
1-C
6Alkyl or halo C
1-C
6Alkyl;
R
4And R
5Can be identical or different, be respectively H, CO
2R
3, CONHR
3, CHR
3CO
2R
3, CHR
3CONR
3R
7, bromine, chlorine, fluorine, C
1-C
6Alkyl, halo C
1-C
6Alkyl, C
1-C
6Alkoxyl group or C
1-C
6Alkylthio;
R
6Be H, bromine, chlorine, fluorine, CN, CO
2R
3, CONR
3R
7, OR
3, SR
3, SO
2R
3, NR
3R
7, SO
2NR
3R
7Or C
1-C
6Alkyl;
R
7Be H, C
1-C
6Alkyl, halo C
1-C
6Alkyl or COR
3
X-Z is CH=CCl or CH
2CHCl;
When X was O or S, Z was CHR
3
Q is Q1;
And by the formed sodium salt that can on agricultural, use of organic or inorganic alkali, sylvite, triethylamine salt or pyridinium salt.
3, according to the described compound of claim 2, it is characterized in that: among the general formula compound I
R
1Be F;
R
2Be Cl;
R
3Be H;
R
4And R
5Be respectively H or C
1-C
6Alkyl;
R
6Be CN or CO
2C
2H
5
X is O;
Z is CH
2
Q is Q1.
4, a kind of herbicidal composition is characterized in that: with the compound of Formula I described in the claim 1 is active ingredient, and its content is 0.1% to 95%.
5, according to the described herbicidal composition of claim 4, it is characterized in that: also contain agricultural in the composition and go up acceptable carrier and tensio-active agent.
6, the purposes of the described compound of claim 1 aspect management of weeds.
7, the method for a kind of management of weeds is characterized in that: weeds, weed growth ground or weed growth medium to farm crop Tanaka are used herbicidal composition as claimed in claim 4.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB03143374XA CN100491338C (en) | 2003-09-29 | 2003-09-29 | Substituted amide herbicides |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB03143374XA CN100491338C (en) | 2003-09-29 | 2003-09-29 | Substituted amide herbicides |
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|---|---|
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| CN100491338C true CN100491338C (en) | 2009-05-27 |
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ID=34659395
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| CN106831618B (en) * | 2015-12-04 | 2019-11-12 | 沈阳中化农药化工研发有限公司 | A kind of quaternary ammonium compound and its application |
| CN117402121A (en) * | 2022-07-14 | 2024-01-16 | 武汉智汇农耀科技有限公司 | Triazolinone structure-containing compound, and preparation method and application thereof |
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