CN1032005A - 除草剂 - Google Patents

除草剂 Download PDF

Info

Publication number: CN1032005A
Authority: CN; China
Prior art keywords: compound; och; chf; group; alkyl
Prior art date: 1986-08-20
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.): Pending

Application number

CN87105742A

Other languages

English (en)

Chinese (zh)

Inventor

乔治·奥西多里斯

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

FMC Corp

Original Assignee

FMC Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-08-20

Filing date

1987-08-20

Publication date

1989-03-29

1987-08-20 Application filed by FMC Corp filed Critical FMC Corp

1989-03-29 Publication of CN1032005A publication Critical patent/CN1032005A/zh

Status Pending legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 65
239000000460 chlorine Substances 0.000 claims description 91
239000000203 mixture Substances 0.000 claims description 36
238000000034 method Methods 0.000 claims description 33
-1 nitro, amino Chemical group 0.000 claims description 32
238000009333 weeding Methods 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 22
125000003545 alkoxy group Chemical group 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
125000001188 haloalkyl group Chemical group 0.000 claims description 7
125000003282 alkyl amino group Chemical group 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
230000008635 plant growth Effects 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000000033 alkoxyamino group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
125000006323 alkenyl amino group Chemical group 0.000 claims description 2
125000003302 alkenyloxy group Chemical group 0.000 claims description 2
125000005133 alkynyloxy group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 23
230000002363 herbicidal effect Effects 0.000 abstract description 8
125000004104 aryloxy group Chemical group 0.000 abstract 1
FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 abstract 1
229910052799 carbon Inorganic materials 0.000 description 15
238000009472 formulation Methods 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 10
241000196324 Embryophyta Species 0.000 description 9
238000012360 testing method Methods 0.000 description 9
240000006995 Abutilon theophrasti Species 0.000 description 8
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
150000001345 alkine derivatives Chemical group 0.000 description 8
125000001309 chloro group Chemical group Cl* 0.000 description 8
239000006185 dispersion Substances 0.000 description 8
239000000843 powder Substances 0.000 description 8
241000219146 Gossypium Species 0.000 description 7
239000007788 liquid Substances 0.000 description 7
239000002245 particle Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 7
239000007787 solid Substances 0.000 description 7
244000058871 Echinochloa crus-galli Species 0.000 description 6
244000068988 Glycine max Species 0.000 description 6
235000010469 Glycine max Nutrition 0.000 description 6
235000003403 Limnocharis flava Nutrition 0.000 description 6
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
241000209140 Triticum Species 0.000 description 6
235000021307 Triticum Nutrition 0.000 description 6
240000008042 Zea mays Species 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
230000000694 effects Effects 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
239000004563 wettable powder Substances 0.000 description 6
229920000742 Cotton Polymers 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
240000007594 Oryza sativa Species 0.000 description 5
235000007164 Oryza sativa Nutrition 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
244000046109 Sorghum vulgare var. nervosum Species 0.000 description 5
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
235000002017 Zea mays subsp mays Nutrition 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
235000005822 corn Nutrition 0.000 description 5
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 5
229910003446 platinum oxide Inorganic materials 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
239000007921 spray Substances 0.000 description 5
239000004575 stone Substances 0.000 description 5
239000004577 thatch Substances 0.000 description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
235000015320 potassium carbonate Nutrition 0.000 description 4
235000009566 rice Nutrition 0.000 description 4
239000003643 water by type Substances 0.000 description 4
239000000080 wetting agent Substances 0.000 description 4
244000024671 Brassica kaber Species 0.000 description 3
235000004977 Brassica sinapistrum Nutrition 0.000 description 3
235000001543 Corylus americana Nutrition 0.000 description 3
240000007582 Corylus avellana Species 0.000 description 3
235000007466 Corylus avellana Nutrition 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
229960001413 acetanilide Drugs 0.000 description 3
239000003513 alkali Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000004009 herbicide Substances 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 description 3
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
235000009438 Gossypium Nutrition 0.000 description 2
239000005639 Lauric acid Substances 0.000 description 2
231100000674 Phytotoxicity Toxicity 0.000 description 2
240000003461 Setaria viridis Species 0.000 description 2
235000002248 Setaria viridis Nutrition 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000003905 agrochemical Substances 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
238000013459 approach Methods 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
235000013877 carbamide Nutrition 0.000 description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
239000004927 clay Substances 0.000 description 2
229910000365 copper sulfate Inorganic materials 0.000 description 2
229960003280 cupric chloride Drugs 0.000 description 2
MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
231100000614 poison Toxicity 0.000 description 2
230000007096 poisonous effect Effects 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
238000009834 vaporization Methods 0.000 description 2
239000004562 water dispersible granule Substances 0.000 description 2
IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 description 1
XNJAYQHWXYJBBD-UHFFFAOYSA-N 1,4-difluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(F)=CC=C1F XNJAYQHWXYJBBD-UHFFFAOYSA-N 0.000 description 1
XVIRIXVOLLJIPF-UHFFFAOYSA-N 1-nitro-2-(2-nitrophenoxy)benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1=CC=CC=C1[N+]([O-])=O XVIRIXVOLLJIPF-UHFFFAOYSA-N 0.000 description 1
VRTZOSBFGAMKPD-UHFFFAOYSA-N 2-(3-hydroxypyridin-2-yl)oxypyridin-3-ol Chemical compound OC1=CC=CN=C1OC1=NC=CC=C1O VRTZOSBFGAMKPD-UHFFFAOYSA-N 0.000 description 1
JQULXIOYDDCNGR-UHFFFAOYSA-N 2-amino-2-methylpropanenitrile Chemical compound CC(C)(N)C#N JQULXIOYDDCNGR-UHFFFAOYSA-N 0.000 description 1
NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 1
ZXGHKJHRHVDMSW-UHFFFAOYSA-N 2-chloro-5-methoxypyridine Chemical compound COC1=CC=C(Cl)N=C1 ZXGHKJHRHVDMSW-UHFFFAOYSA-N 0.000 description 1
WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 1
VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
KSZQZUAJEWXGQM-UHFFFAOYSA-N 2-fluoro-5-methoxypyridine Chemical compound COC1=CC=C(F)N=C1 KSZQZUAJEWXGQM-UHFFFAOYSA-N 0.000 description 1
IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 description 1
XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-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
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
235000011331 Brassica Nutrition 0.000 description 1
241000219198 Brassica Species 0.000 description 1
FPVHTXASNQXRRV-UHFFFAOYSA-N C(CC)N(C1=CC=C(C=C1)C(F)(F)F)CCC.[N+](=O)([O-])C1=CC(=CC=C1)[N+](=O)[O-] Chemical compound C(CC)N(C1=CC=C(C=C1)C(F)(F)F)CCC.[N+](=O)([O-])C1=CC(=CC=C1)[N+](=O)[O-] FPVHTXASNQXRRV-UHFFFAOYSA-N 0.000 description 1
240000006555 Chamaerops humilis Species 0.000 description 1
241000207894 Convolvulus arvensis Species 0.000 description 1
WFKSADNZWSKCRZ-UHFFFAOYSA-N Diethatyl-ethyl Chemical group CCOC(=O)CN(C(=O)CCl)C1=C(CC)C=CC=C1CC WFKSADNZWSKCRZ-UHFFFAOYSA-N 0.000 description 1
239000005510 Diuron Substances 0.000 description 1
241000628997 Flos Species 0.000 description 1
239000005533 Fluometuron Substances 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
240000007049 Juglans regia Species 0.000 description 1
235000009496 Juglans regia Nutrition 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
241000209094 Oryza Species 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
240000002439 Sorghum halepense Species 0.000 description 1
235000007244 Zea mays Nutrition 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000005336 allyloxy group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000003321 amplification Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
HAVZTGSQJIEKPI-UHFFFAOYSA-N benzothiadiazine Chemical compound C1=CC=C2C=NNSC2=C1 HAVZTGSQJIEKPI-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
IZBNNCFOBMGTQX-UHFFFAOYSA-N etoperidone Chemical group O=C1N(CC)C(CC)=NN1CCCN1CCN(C=2C=C(Cl)C=CC=2)CC1 IZBNNCFOBMGTQX-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
125000003709 fluoroalkyl group Chemical group 0.000 description 1
238000010413 gardening Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000012010 growth Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
JYINMLPNDRBKKZ-UHFFFAOYSA-N hydroperoxybenzene Chemical compound OOC1=CC=CC=C1 JYINMLPNDRBKKZ-UHFFFAOYSA-N 0.000 description 1
230000008676 import Effects 0.000 description 1
230000008595 infiltration Effects 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
230000005764 inhibitory process Effects 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
235000012054 meals Nutrition 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
LOFYLIRHOUPKFX-UHFFFAOYSA-N n-(methoxymethyl)acetamide Chemical compound COCNC(C)=O LOFYLIRHOUPKFX-UHFFFAOYSA-N 0.000 description 1
YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
DQHUNQPOBFLPAH-UHFFFAOYSA-N n-benzyl-2-[4-chloro-5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-n-phenylacetamide Chemical compound CC1=C(Cl)C(C(F)(F)F)=NN1CC(=O)N(C=1C=CC=CC=1)CC1=CC=CC=C1 DQHUNQPOBFLPAH-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
NICDRCVJGXLKSF-UHFFFAOYSA-N nitric acid;trihydrochloride Chemical class Cl.Cl.Cl.O[N+]([O-])=O NICDRCVJGXLKSF-UHFFFAOYSA-N 0.000 description 1
238000003199 nucleic acid amplification method Methods 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
235000015170 shellfish Nutrition 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
229940001516 sodium nitrate Drugs 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Agronomy & Crop Science (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

CN87105742A 1986-08-20 1987-08-20 除草剂 Pending CN1032005A (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US89845386A	1986-08-20	1986-08-20
US898,453		1986-08-20

Publications (1)

Publication Number	Publication Date
CN1032005A true CN1032005A (zh)	1989-03-29

Family

ID=25409480

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN87105742A Pending CN1032005A (zh)	1986-08-20	1987-08-20	除草剂

Country Status (8)

Country	Link
EP (1)	EP0322413A4 (de)
JP (1)	JPH02500271A (de)
KR (1)	KR880701527A (de)
CN (1)	CN1032005A (de)
BR (1)	BR8707779A (de)
HU (1)	HUT48799A (de)
WO (1)	WO1988001133A1 (de)
ZA (1)	ZA876179B (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN110072853A (zh) *	2016-12-16	2019-07-30	巴斯夫欧洲公司	除草的苯基三唑啉酮类

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US5262390A (en) *	1992-08-26	1993-11-16	Fmc Corporation	Herbicical 2-[(4-heterocyclic-phenoxymethyl)phenoxy]-alkanoates
UA57070C2 (uk) *	1997-03-14	2003-06-16	Іск Амерікас Інкорпорейтед	Діарилові ефіри, гербіциднa композиція та спосіб боротьби з бур'янами
DE19901846A1 (de) *	1999-01-19	2000-07-20	Bayer Ag	Substituierte Arylheterocyclen
CA2804593C (en)	2010-07-09	2015-11-24	Pfizer Limited	Biphenyloxybenzensulphonamide derivatives useful as sodium channel inhibitors
ES2526541T3 (es)	2010-07-12	2015-01-13	Pfizer Limited	N-sulfonilbenzamidas como inhibidores de canales de sodio dependientes de voltaje
WO2012007883A1 (en)	2010-07-12	2012-01-19	Pfizer Limited	Sulfonamide derivatives as nav1.7 inhibitors for the treatment of pain
CA2804716A1 (en)	2010-07-12	2012-01-19	Pfizer Limited	Chemical compounds
JP2013531030A (ja)	2010-07-12	2013-08-01	ファイザー・リミテッド	電位開口型ナトリウムチャネルの阻害剤としてのｎ−スルホニルベンズアミド
CA2801032A1 (en)	2010-07-12	2012-01-19	Pfizer Limited	N-sulfonylbenzamide derivatives useful as voltage gated sodium channel inhibitors
US12331027B2 (en)	2017-11-23	2025-06-17	Basf Se	Herbicidal pyridylethers

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2846038A1 (de) *	1978-10-23	1980-05-08	Basf Ag	1,2,4-triazolderivate, ihre herstellung und verwendung
US4318731A (en) *	1979-08-25	1982-03-09	Nihon Nohyaku Co., Ltd.	Δ2 -1,2,4-triazolin-5-one derivatives and herbicidal usage thereof
US4404019A (en) *	1980-12-24	1983-09-13	Sumitomo Chemical Company, Limited	3-Chloro-1-phenyl-1,2,4-triazolin-5-ones and their use as herbicides
CH651029A5 (de) *	1980-12-25	1985-08-30	Nihon Nohyaku Co Ltd	Triazolin-derivate, verfahren zu ihrer herstellung und sie enthaltende herbizide mittel.
DK348883A (da) *	1982-08-13	1984-02-14	Dow Chemical Co	Aryl(aryloxy eller arylthio)azolomethaner, deres fremstilling og anvendelse
US4636514A (en) *	1982-08-13	1987-01-13	The Dow Chemical Company	Aryl(aryloxy or arylthio)azolomethanes
PH18938A (en) *	1982-09-28	1985-11-11	Sumitomo Chemical Co	2-substituted phenyl-4,5,6,7-tetrahydro-2h-indazoles and their use
JPS59148785A (ja) *	1983-02-15	1984-08-25	Sumitomo Chem Co Ltd	ピリドトリアゾリウム誘導体、その製造法およびそれを有効成分とする除草剤
EP0177553A4 (de) *	1984-03-29	1986-08-21	Fmc Corp	Untkrautvertilgende 1-aryl-delta-1,2,4-triazolin-5-one.

1987
- 1987-08-05 EP EP19870905518 patent/EP0322413A4/de not_active Withdrawn
- 1987-08-05 JP JP62505029A patent/JPH02500271A/ja active Pending
- 1987-08-05 HU HU874354A patent/HUT48799A/hu unknown
- 1987-08-05 BR BR8707779A patent/BR8707779A/pt unknown
- 1987-08-05 WO PCT/US1987/001928 patent/WO1988001133A1/en not_active Ceased
- 1987-08-20 CN CN87105742A patent/CN1032005A/zh active Pending
- 1987-08-20 ZA ZA876179A patent/ZA876179B/xx unknown
1988
- 1988-04-19 KR KR1019880700414A patent/KR880701527A/ko not_active Withdrawn

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN110072853A (zh) *	2016-12-16	2019-07-30	巴斯夫欧洲公司	除草的苯基三唑啉酮类
CN110072853B (zh) *	2016-12-16	2023-07-25	巴斯夫欧洲公司	除草的苯基三唑啉酮类

Also Published As

Publication number	Publication date
BR8707779A (pt)	1989-08-15
WO1988001133A1 (en)	1988-02-25
KR880701527A (ko)	1988-11-03
EP0322413A1 (de)	1989-07-05
ZA876179B (en)	1988-02-23
EP0322413A4 (de)	1989-10-04
JPH02500271A (ja)	1990-02-01
HUT48799A (en)	1989-07-28

Legal Events

Date	Code	Title
1988-01-20	C10	Entry into substantive examination
1988-01-20	SE01	Entry into force of request for substantive examination
1989-03-29	C06	Publication
1989-03-29	PB01	Publication
1992-04-22	C01	Deemed withdrawal of patent application (patent law 1993)
1992-04-22	WD01	Invention patent application deemed withdrawn after publication

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