DE2229036A1 - - Google Patents
Info
- Publication number
- DE2229036A1 DE2229036A1 DE19722229036 DE2229036A DE2229036A1 DE 2229036 A1 DE2229036 A1 DE 2229036A1 DE 19722229036 DE19722229036 DE 19722229036 DE 2229036 A DE2229036 A DE 2229036A DE 2229036 A1 DE2229036 A1 DE 2229036A1
- Authority
- DE
- Germany
- Prior art keywords
- benzenediacetonitrile
- butyl
- nitro
- tert
- isopropyl
- 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.)
- Pending
Links
- -1 halogen radical Chemical class 0.000 claims description 401
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 64
- 239000000203 mixture Substances 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 32
- 239000004480 active ingredient Substances 0.000 claims description 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
- 150000003254 radicals Chemical class 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000004009 herbicide Substances 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
- LXILWCVDBPYYOP-UHFFFAOYSA-N 2-[4-(cyanomethyl)-2,5-bis(2-methylpropyl)phenyl]acetonitrile Chemical compound C(C(C)C)C1=C(C=C(C(=C1)CC#N)CC(C)C)CC#N LXILWCVDBPYYOP-UHFFFAOYSA-N 0.000 claims description 3
- 244000045561 useful plants Species 0.000 claims description 2
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- OWIGEBDDPPLDLE-UHFFFAOYSA-N 2-[2-tert-butyl-3-(cyanomethyl)-5-propan-2-ylphenyl]acetonitrile Chemical compound C(C)(C)(C)C1=C(C=C(C=C1CC#N)C(C)C)CC#N OWIGEBDDPPLDLE-UHFFFAOYSA-N 0.000 claims 1
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 claims 1
- 241000251730 Chondrichthyes Species 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- GRPFZJNUYXIVSL-UHFFFAOYSA-N 2-[3-(cyanomethyl)phenyl]acetonitrile Chemical compound N#CCC1=CC=CC(CC#N)=C1 GRPFZJNUYXIVSL-UHFFFAOYSA-N 0.000 description 32
- 241000196324 Embryophyta Species 0.000 description 31
- 239000008187 granular material Substances 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- 235000010469 Glycine max Nutrition 0.000 description 21
- 244000068988 Glycine max Species 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 244000025670 Eleusine indica Species 0.000 description 19
- 235000014716 Eleusine indica Nutrition 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000004615 ingredient Substances 0.000 description 18
- CSIFGMFVGDBOQC-UHFFFAOYSA-N 3-iminobutanenitrile Chemical compound CC(=N)CC#N CSIFGMFVGDBOQC-UHFFFAOYSA-N 0.000 description 17
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 16
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 16
- 235000005476 Digitaria cruciata Nutrition 0.000 description 16
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- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 16
- 244000062793 Sorghum vulgare Species 0.000 description 16
- 235000019713 millet Nutrition 0.000 description 16
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 15
- 241000219312 Chenopodium Species 0.000 description 15
- 240000007594 Oryza sativa Species 0.000 description 15
- 235000007164 Oryza sativa Nutrition 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 235000009566 rice Nutrition 0.000 description 15
- 239000002689 soil Substances 0.000 description 15
- 125000006839 xylylene group Chemical group 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 13
- 241000482268 Zea mays subsp. mays Species 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
- 241000287828 Gallus gallus Species 0.000 description 12
- UJVMDSLYYCDVGW-UHFFFAOYSA-N acetonitrile;benzene Chemical compound CC#N.CC#N.C1=CC=CC=C1 UJVMDSLYYCDVGW-UHFFFAOYSA-N 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 230000002363 herbicidal effect Effects 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 241000209140 Triticum Species 0.000 description 9
- 235000021307 Triticum Nutrition 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 240000001592 Amaranthus caudatus Species 0.000 description 8
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- GRJWOKACBGZOKT-UHFFFAOYSA-N 1,3-bis(chloromethyl)benzene Chemical compound ClCC1=CC=CC(CCl)=C1 GRJWOKACBGZOKT-UHFFFAOYSA-N 0.000 description 7
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 7
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 7
- 239000004495 emulsifiable concentrate Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
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- 238000003756 stirring Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical class ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 6
- 240000006122 Chenopodium album Species 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 240000002439 Sorghum halepense Species 0.000 description 6
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 6
- 238000013459 approach Methods 0.000 description 6
- 230000035784 germination Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 235000009973 maize Nutrition 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000004563 wettable powder Substances 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- FUQCKESKNZBNOG-UHFFFAOYSA-N 2-[4-(cyanomethyl)phenyl]acetonitrile Chemical compound N#CCC1=CC=C(CC#N)C=C1 FUQCKESKNZBNOG-UHFFFAOYSA-N 0.000 description 5
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 5
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 5
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 5
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 5
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 5
- 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 5
- 241001148659 Panicum dichotomiflorum Species 0.000 description 5
- 241001355178 Setaria faberi Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 229960000892 attapulgite Drugs 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 5
- 229910052625 palygorskite Inorganic materials 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 241000219318 Amaranthus Species 0.000 description 4
- 244000281762 Chenopodium ambrosioides Species 0.000 description 4
- 240000008853 Datura stramonium Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 241000320639 Leptochloa Species 0.000 description 4
- 239000005573 Linuron Substances 0.000 description 4
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- 235000017016 Setaria faberi Nutrition 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
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- 239000007921 spray Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- NNNQOSBFUYVHTG-UHFFFAOYSA-N 2-[4-(cyanomethyl)-2,5-di(propan-2-yl)phenyl]acetonitrile Chemical compound C(C)(C)C1=C(C=C(C(=C1)CC#N)C(C)C)CC#N NNNQOSBFUYVHTG-UHFFFAOYSA-N 0.000 description 3
- FVDFOPLANFYOJD-UHFFFAOYSA-N 2-ethylbenzene-1,3-dicarboxylic acid Chemical compound CCC1=C(C(O)=O)C=CC=C1C(O)=O FVDFOPLANFYOJD-UHFFFAOYSA-N 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
- C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
- C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/02—Monocyclic aromatic halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/02—Monocyclic aromatic halogenated hydrocarbons
- C07C25/125—Halogenated xylenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/02—Monocyclic aromatic halogenated hydrocarbons
- C07C25/13—Monocyclic aromatic halogenated hydrocarbons containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/14—Monocyclic dicarboxylic acids
- C07C63/15—Monocyclic dicarboxylic acids all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15342771A | 1971-06-15 | 1971-06-15 | |
| US15342971A | 1971-06-15 | 1971-06-15 | |
| US241800A US3877926A (en) | 1971-06-15 | 1972-04-06 | Herbicidal compounds, compositions and methods |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2229036A1 true DE2229036A1 (enExample) | 1972-12-21 |
Family
ID=27387444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722229036 Pending DE2229036A1 (enExample) | 1971-06-15 | 1972-06-14 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3877926A (enExample) |
| AR (1) | AR195169A1 (enExample) |
| DD (1) | DD105710A5 (enExample) |
| DE (1) | DE2229036A1 (enExample) |
| HU (1) | HU164730B (enExample) |
| IL (1) | IL39568A0 (enExample) |
| NL (1) | NL7208194A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5266723A (en) * | 1989-05-16 | 1993-11-30 | Medice, Ltd., Chem.-Pharm. Fabrik Putter Gmbh & Co. Kg | Process for the preparation of optically active 2-aryl-alkanoic acids, especially 2-aryl-propionic acids |
| CN112047804B (zh) * | 2020-09-10 | 2023-06-27 | 内蒙古永太化学有限公司 | 一种3,5-二氯-4-氟溴苯化合物的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1223608B (de) * | 1963-09-10 | 1966-08-25 | Bayer Ag | Totalherbizide Mittel |
| US3504001A (en) * | 1965-12-16 | 1970-03-31 | Du Pont | Synthesis of malononitriles and dimalononitriles and compounds produced therein |
| US3574594A (en) * | 1968-04-29 | 1971-04-13 | Mobil Oil Corp | Phenylacetonitriles as pre-emergence herbicides |
-
1972
- 1972-04-06 US US241800A patent/US3877926A/en not_active Expired - Lifetime
- 1972-05-29 IL IL39568A patent/IL39568A0/xx unknown
- 1972-06-13 DD DD163671A patent/DD105710A5/xx unknown
- 1972-06-13 HU HUDU186A patent/HU164730B/hu unknown
- 1972-06-14 DE DE19722229036 patent/DE2229036A1/de active Pending
- 1972-06-14 AR AR242531A patent/AR195169A1/es active
- 1972-06-15 NL NL7208194A patent/NL7208194A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3877926A (en) | 1975-04-15 |
| NL7208194A (enExample) | 1972-12-19 |
| AR195169A1 (es) | 1973-09-19 |
| HU164730B (enExample) | 1974-04-11 |
| IL39568A0 (en) | 1972-07-26 |
| DD105710A5 (enExample) | 1974-05-12 |
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