CN87100152A - 除草的化合物 - Google Patents
除草的化合物 Download PDFInfo
- Publication number
- CN87100152A CN87100152A CN198787100152A CN87100152A CN87100152A CN 87100152 A CN87100152 A CN 87100152A CN 198787100152 A CN198787100152 A CN 198787100152A CN 87100152 A CN87100152 A CN 87100152A CN 87100152 A CN87100152 A CN 87100152A
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- CN
- China
- Prior art keywords
- alkyl
- compound
- group
- carbonyl
- low
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 79
- 238000009333 weeding Methods 0.000 title claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 45
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 23
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 19
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims description 59
- 238000000034 method Methods 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 241000196324 Embryophyta Species 0.000 claims description 23
- 240000007594 Oryza sativa Species 0.000 claims description 22
- 235000007164 Oryza sativa Nutrition 0.000 claims description 21
- 235000009566 rice Nutrition 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 244000068988 Glycine max Species 0.000 claims description 15
- 235000010469 Glycine max Nutrition 0.000 claims description 15
- 229910020008 S(O) Inorganic materials 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 241000209140 Triticum Species 0.000 claims description 14
- 235000021307 Triticum Nutrition 0.000 claims description 14
- 240000008042 Zea mays Species 0.000 claims description 14
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 13
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 13
- 235000005822 corn Nutrition 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
- OSQBFLZKVLCVGI-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-1-carbonyl 1,2,3,4-tetrahydronaphthalene-1-carboxylate Chemical compound C1CCC2=CC=CC=C2C1C(=O)OC(=O)C1C2=CC=CC=C2CCC1 OSQBFLZKVLCVGI-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000006354 carbonyl alkylene group Chemical group 0.000 claims 4
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 238000009331 sowing Methods 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- -1 aryl tetrahydro-phthalimide class Chemical class 0.000 description 68
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 239000002904 solvent Substances 0.000 description 42
- 238000009834 vaporization Methods 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 24
- 239000003921 oil Substances 0.000 description 24
- 239000007787 solid Substances 0.000 description 21
- 238000000605 extraction Methods 0.000 description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 238000002329 infrared spectrum Methods 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 230000002194 synthesizing effect Effects 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229960001866 silicon dioxide Drugs 0.000 description 15
- 238000005406 washing Methods 0.000 description 15
- 240000006995 Abutilon theophrasti Species 0.000 description 14
- 244000058871 Echinochloa crus-galli Species 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 241000219146 Gossypium Species 0.000 description 12
- 235000003403 Limnocharis flava Nutrition 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 229920000742 Cotton Polymers 0.000 description 11
- 240000002439 Sorghum halepense Species 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 241000628997 Flos Species 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 240000001549 Ipomoea eriocarpa Species 0.000 description 10
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 239000003643 water by type Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- 238000005194 fractionation Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- 230000002363 herbicidal effect Effects 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 239000004563 wettable powder Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical class BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 6
- 229910003446 platinum oxide Inorganic materials 0.000 description 6
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- GAUUDQVOPUKGJD-UHFFFAOYSA-N 1-(bromomethyl)-2-chloro-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C(Cl)=C1 GAUUDQVOPUKGJD-UHFFFAOYSA-N 0.000 description 5
- 229960004756 ethanol Drugs 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 230000001771 impaired effect Effects 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- KMQWNQKESAHDKD-UHFFFAOYSA-N 2-chloro-4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C(Cl)=C1 KMQWNQKESAHDKD-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- 244000024671 Brassica kaber Species 0.000 description 4
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 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
- 239000000047 product Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- AAJNBHMHFXIMJE-UHFFFAOYSA-N 2-[4-bromo-5-(ethoxymethyl)-2-fluorophenyl]-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(Br)C(COCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F AAJNBHMHFXIMJE-UHFFFAOYSA-N 0.000 description 3
- XDTIEVSJCJJDHD-UHFFFAOYSA-N 2-[4-chloro-2-fluoro-5-(hydroxymethyl)phenyl]-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(Cl)C(CO)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F XDTIEVSJCJJDHD-UHFFFAOYSA-N 0.000 description 3
- TZDGXJQHRMBJOL-UHFFFAOYSA-N 2-[4-chloro-2-fluoro-5-(phenoxymethyl)phenyl]-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(N2C(C3=C(CCCC3)C2=O)=O)C(F)=CC(Cl)=C1COC1=CC=CC=C1 TZDGXJQHRMBJOL-UHFFFAOYSA-N 0.000 description 3
- UZDOGMHOYWOBDY-UHFFFAOYSA-N 2-[4-chloro-5-(ethoxymethyl)-2-fluorophenyl]-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(Cl)C(COCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F UZDOGMHOYWOBDY-UHFFFAOYSA-N 0.000 description 3
- QPLUIZXBWYUFMY-UHFFFAOYSA-N 2-bromo-1-(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C(Br)=C1 QPLUIZXBWYUFMY-UHFFFAOYSA-N 0.000 description 3
- HNOIAPRHNXBCAE-UHFFFAOYSA-N 2-chloro-4-fluoro-5-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC(C=O)=C(Cl)C=C1F HNOIAPRHNXBCAE-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- IDNUEBSJWINEMI-UHFFFAOYSA-N ethyl nitrate Chemical compound CCO[N+]([O-])=O IDNUEBSJWINEMI-UHFFFAOYSA-N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000002045 lasting effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- FSWLWXDRKJHXJP-UHFFFAOYSA-N n-acetyl-n-(4-chloro-2-fluoro-5-methylphenyl)acetamide Chemical compound CC(=O)N(C(C)=O)C1=CC(C)=C(Cl)C=C1F FSWLWXDRKJHXJP-UHFFFAOYSA-N 0.000 description 3
- ZFKDEBMPLHIKKC-UHFFFAOYSA-N n-acetyl-n-[5-(bromomethyl)-4-chloro-2-fluorophenyl]acetamide Chemical compound CC(=O)N(C(C)=O)C1=CC(CBr)=C(Cl)C=C1F ZFKDEBMPLHIKKC-UHFFFAOYSA-N 0.000 description 3
- 239000012434 nucleophilic reagent Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000004323 potassium nitrate Substances 0.000 description 3
- 235000010333 potassium nitrate Nutrition 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- SHTSRGNCCVQHEK-UHFFFAOYSA-N 1-(5-acetamido-2-chloro-4-fluorophenyl)ethyl nitrate Chemical compound [O-][N+](=O)OC(C)C1=CC(NC(C)=O)=C(F)C=C1Cl SHTSRGNCCVQHEK-UHFFFAOYSA-N 0.000 description 2
- YXVJHZWHPLOEAP-UHFFFAOYSA-N 1-chloro-5-fluoro-2-methyl-4-nitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=C(F)C=C1Cl YXVJHZWHPLOEAP-UHFFFAOYSA-N 0.000 description 2
- DIMPXPFOEFDMPO-UHFFFAOYSA-N 2-[4-chloro-2-fluoro-5-(1-methoxyethyl)phenyl]-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(Cl)C(C(C)OC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F DIMPXPFOEFDMPO-UHFFFAOYSA-N 0.000 description 2
- QJJUGVSLXVYOBL-UHFFFAOYSA-N 4-chloro-2-fluoro-5-(1-methoxyethyl)aniline Chemical compound COC(C)C1=CC(N)=C(F)C=C1Cl QJJUGVSLXVYOBL-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 244000285774 Cyperus esculentus Species 0.000 description 2
- 235000005853 Cyperus esculentus Nutrition 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
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- 150000001345 alkine derivatives Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 2
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- 238000002474 experimental method Methods 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
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- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
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- WVQVZIXHZKYARN-UHFFFAOYSA-N n-[4-chloro-2-fluoro-5-(1-methoxyethyl)phenyl]acetamide Chemical compound COC(C)C1=CC(NC(C)=O)=C(F)C=C1Cl WVQVZIXHZKYARN-UHFFFAOYSA-N 0.000 description 2
- BEFJYDMWFYEPSJ-UHFFFAOYSA-N n-[[2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)-4-fluorophenyl]methyl]-n-methylmethanesulfonamide Chemical compound C1=C(Cl)C(CN(C)S(C)(=O)=O)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F BEFJYDMWFYEPSJ-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- PNPIRSNMYIHTPS-UHFFFAOYSA-N nitroso nitrate Chemical class [O-][N+](=O)ON=O PNPIRSNMYIHTPS-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 230000007096 poisonous effect Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- MYEUMUCLVULHAU-UHFFFAOYSA-N (2-chloro-4-fluoro-5-nitrophenyl)methanol Chemical compound OCC1=CC([N+]([O-])=O)=C(F)C=C1Cl MYEUMUCLVULHAU-UHFFFAOYSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- QEXZLRPDTPQYHC-UHFFFAOYSA-N (5-amino-2-chloro-4-fluorophenyl)methanol Chemical compound NC1=CC(CO)=C(Cl)C=C1F QEXZLRPDTPQYHC-UHFFFAOYSA-N 0.000 description 1
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-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
- 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
- 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
- CIFFBTOJCKSRJY-UHFFFAOYSA-N 3α,4,7,7α-tetrahydro-1h-isoindole-1,3(2h)-dione Chemical compound C1C=CCC2C(=O)NC(=O)C21 CIFFBTOJCKSRJY-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 241000748223 Alisma Species 0.000 description 1
- 241000509537 Alisma canaliculatum Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
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- 244000106835 Bindesalat 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
- 244000025254 Cannabis sativa Species 0.000 description 1
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- 235000002848 Cyperus flabelliformis Nutrition 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
- 239000005533 Fluometuron Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 235000009438 Gossypium Nutrition 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 240000000178 Monochoria vaginalis Species 0.000 description 1
- 241000209094 Oryza Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 244000104677 Peltiphyllum peltatum Species 0.000 description 1
- 235000014968 Peltiphyllum peltatum Nutrition 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000009132 Sagittaria sagittifolia Species 0.000 description 1
- 244000080395 Sagittaria subulata Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 244000046109 Sorghum vulgare var. nervosum Species 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- BBOPZLFBGQCZHF-UHFFFAOYSA-N [Br].C[Mg] Chemical compound [Br].C[Mg] BBOPZLFBGQCZHF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 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
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 244000046738 asparagus lettuce Species 0.000 description 1
- 235000006705 asparagus lettuce Nutrition 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
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 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
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 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
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010413 gardening Methods 0.000 description 1
- 230000002650 habitual effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000005457 ice water Substances 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
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 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
- 239000006210 lotion Substances 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
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical class [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- 125000005245 nitryl group Chemical class [N+](=O)([O-])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical class BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 1
- 239000004577 thatch Substances 0.000 description 1
- 244000082735 tidal marsh flat sedge Species 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
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/32—Cyclic imides of polybasic carboxylic acids or thio analogues thereof
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Indole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81864786A | 1986-01-10 | 1986-01-10 | |
| US818,647 | 1986-01-10 | ||
| US91455586A | 1986-10-03 | 1986-10-03 | |
| US914,555 | 1986-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN87100152A true CN87100152A (zh) | 1987-08-12 |
Family
ID=27124289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN198787100152A Pending CN87100152A (zh) | 1986-01-10 | 1987-01-09 | 除草的化合物 |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN87100152A (it) |
| IT (1) | IT1201113B (it) |
| WO (1) | WO1987004049A1 (it) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1067214C (zh) * | 1996-03-07 | 2001-06-20 | 苏春明 | 复合型稻田除草剂及制法 |
| CN105777733A (zh) * | 2014-12-16 | 2016-07-20 | 沈阳中化农药化工研发有限公司 | 一种含异恶唑啉的四氢邻苯二甲酰亚胺类化合物及其用途 |
| CN111848406A (zh) * | 2019-04-26 | 2020-10-30 | 沈阳中化农药化工研发有限公司 | 一种2-氯-4-氟-5-硝基苯甲醛的制备方法 |
| CN112225664A (zh) * | 2020-10-19 | 2021-01-15 | 南通江山农药化工股份有限公司 | 一种硝基苯甲醛、2-氯-4-氟-5-硝基苯甲醛的制备方法及应用 |
| CN114364655A (zh) * | 2019-09-12 | 2022-04-15 | 巴斯夫农业公司 | 硝酸α-甲基-[4-(硝基)-2-(三氟甲基)]-苄酯的制备方法 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5162583A (en) * | 1987-03-10 | 1992-11-10 | Kureha Kagaku Kogyo Kabushiki Kaisha | Benzylether derivatives |
| JPH0778047B2 (ja) * | 1987-03-10 | 1995-08-23 | 呉羽化学工業株式会社 | １，５−ジフエニル−１ｈ−１，２，４−トリアゾ−ル−３−カルボン酸アミド誘導体及び該誘導体を含有する除草剤 |
| EP0323271A1 (en) * | 1987-12-30 | 1989-07-05 | Tosoh Corporation | Tetrahydrophthalimide derivative and herbicide composition containing the same |
| US5169428A (en) * | 1987-12-30 | 1992-12-08 | Tosoh Corporation | Tetrahydrophthalimide derivative and herbicide composition containing same |
| DE3905916A1 (de) * | 1989-02-25 | 1990-08-30 | Basf Ag | Verwendung von derivaten des n-phenyl-3,4,5,6-tetrahydrophthalimids zur desikkation und abszission von pflanzenorganen |
| USRE37664E1 (en) * | 1989-02-25 | 2002-04-16 | Basf Aktiengessellschaft | Use of derivatives of N-phenl-3,4,5,6-tetrahydrophthalimide for the desiccation and abscission of plant organs |
| CN1192737A (zh) * | 1995-07-06 | 1998-09-09 | 巴斯福股份公司 | 苄基羟基胺及制备其的中间产物 |
| US7449481B2 (en) | 2004-04-13 | 2008-11-11 | Cephalon, Inc. | Thio-substituted biaryl-methanesulfinyl derivatives |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734073A (en) * | 1956-02-07 | Alpha- | ||
| US2192271A (en) * | 1937-08-20 | 1940-03-05 | Cie Nat Matieres Colorantes | Azo dyestuffs |
| GB881588A (en) * | 1959-02-16 | 1961-11-08 | Francesco Angelini | New alkyl-aryl carbinols |
| NL125434C (it) * | 1961-11-20 | 1900-01-01 | ||
| US3313700A (en) * | 1962-07-18 | 1967-04-11 | Armour Pharmacentical Company | Method of treating the central nervous system with substituted phenethyl carbamates and compositions therefor |
| DE1567204B1 (de) * | 1963-04-02 | 1971-10-14 | Union Carbide Corp | Chlorbenzyl-N-methylcarbamate und diese enthaltende Herbizide |
| US3299127A (en) * | 1964-01-02 | 1967-01-17 | Miles Lab | Hydrogenation of aldehyde dioxolone derivatives of lactic acid |
| CH429291A (de) * | 1964-12-17 | 1966-10-15 | Ciba Geigy | Verfahren zum Schützen von Textilien gegen Schädlinge |
| GB1095359A (it) * | 1964-12-21 | |||
| US3856857A (en) * | 1970-02-13 | 1974-12-24 | En Nom Collectif Science Union | Amino acids and their derivatives |
| DE2334601A1 (de) * | 1973-07-07 | 1975-02-06 | Basf Ag | Thiolcarbamate |
| GB1479297A (en) * | 1974-07-04 | 1977-07-13 | Beecham Group Ltd | 4-substituted butan-2-ones but-3-en-2-ones butan-2-ols and but-3-en-2-ols and pharmaceutical compositions containing them |
| SE412384B (sv) * | 1975-09-04 | 1980-03-03 | Astra Laekemedel Ab | Analogiforfarande for framstellning av antidepressivt verkande trifluormetylsubstituerade aralkylestrar av alanin |
| US3992189A (en) * | 1975-10-31 | 1976-11-16 | E. I. Du Pont De Nemours & Company | Herbicidal isoindol-1-one derivatives |
| GB1576841A (en) * | 1977-01-22 | 1980-10-15 | Beecham Group Ltd | Substituted n-acyl phenylamine compounds having hypolipidaemic activity |
| US4168388A (en) * | 1978-03-23 | 1979-09-18 | Eli Lilly And Company | Trifluoromethylphenyl benzyl ethers |
| US4292070A (en) * | 1979-04-13 | 1981-09-29 | Mitsubishi Chemical Industries, Ltd. | N-Substituted tetrahydrophthalimide and herbicidal composition |
| US4430114A (en) * | 1979-07-25 | 1984-02-07 | American Cyanamid Company | 2,6-Dinitroaniline herbicides, and use thereof |
| DE3036967A1 (de) * | 1980-10-01 | 1982-05-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 3-brom-4-fluor-benzylalkohol und neue zwischenprodukte hierfuer |
| DE3166862D1 (en) * | 1980-11-13 | 1984-11-29 | Rhone Poulenc Spec Chim | Bromopolyfluoralkylthioethers and process for their preparation |
| US4339461A (en) * | 1980-12-29 | 1982-07-13 | Chevron Research Company | N-Substituted 3-nitro-benzylamines |
| US4431822A (en) * | 1981-03-30 | 1984-02-14 | Sumitomo Chemical Company, Limited | Tetrahydrophthalimides, and their production and use |
| JPS58103350A (ja) * | 1981-12-10 | 1983-06-20 | Sumitomo Chem Co Ltd | Ｎ−（α−メチルベンジル）−Ｔ−ブチルハロアセトアミド誘導体、その製造法およびこれらを有効成分として含有する農園芸用殺菌剤 |
| US4552585A (en) * | 1984-10-04 | 1985-11-12 | Fmc Corporation | Herbicidal 2-(aminophenyl)methyl derivatives of 3-isoxazolidinones or 3-oxazinones |
-
1987
- 1987-01-08 IT IT19024/87A patent/IT1201113B/it active
- 1987-01-09 WO PCT/US1987/000056 patent/WO1987004049A1/en not_active Ceased
- 1987-01-09 CN CN198787100152A patent/CN87100152A/zh active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1067214C (zh) * | 1996-03-07 | 2001-06-20 | 苏春明 | 复合型稻田除草剂及制法 |
| CN105777733A (zh) * | 2014-12-16 | 2016-07-20 | 沈阳中化农药化工研发有限公司 | 一种含异恶唑啉的四氢邻苯二甲酰亚胺类化合物及其用途 |
| CN111848406A (zh) * | 2019-04-26 | 2020-10-30 | 沈阳中化农药化工研发有限公司 | 一种2-氯-4-氟-5-硝基苯甲醛的制备方法 |
| CN111848406B (zh) * | 2019-04-26 | 2022-03-29 | 沈阳中化农药化工研发有限公司 | 一种2-氯-4-氟-5-硝基苯甲醛的制备方法 |
| CN114364655A (zh) * | 2019-09-12 | 2022-04-15 | 巴斯夫农业公司 | 硝酸α-甲基-[4-(硝基)-2-(三氟甲基)]-苄酯的制备方法 |
| CN112225664A (zh) * | 2020-10-19 | 2021-01-15 | 南通江山农药化工股份有限公司 | 一种硝基苯甲醛、2-氯-4-氟-5-硝基苯甲醛的制备方法及应用 |
| CN112225664B (zh) * | 2020-10-19 | 2023-03-24 | 南通江山农药化工股份有限公司 | 一种硝基苯甲醛、2-氯-4-氟-5-硝基苯甲醛的制备方法及应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1987004049A1 (en) | 1987-07-16 |
| IT1201113B (it) | 1989-01-27 |
| IT8719024A0 (it) | 1987-01-08 |
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