CS243488B2 - Herbicide and method of efficient substance production - Google Patents

Herbicide and method of efficient substance production Download PDF

Info

Publication number: CS243488B2
Authority: CS; Czechoslovakia
Prior art keywords: active ingredient; acid; formula; alkyl; salt
Prior art date: 1983-05-18

Application number

CS843771A

Other languages

Czech (cs)

English (en)

Other versions

CS377184A2 (en

Inventor

Hans-Georg Brunner

Original Assignee

Ciba Geigy Ag

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.)

1983-05-18

Filing date

1984-05-18

Publication date

1986-06-12

1984-05-18 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1985-08-15 Publication of CS377184A2 publication Critical patent/CS377184A2/cs

1986-06-12 Publication of CS243488B2 publication Critical patent/CS243488B2/cs

Links

230000002363 herbicidal effect Effects 0.000 title claims description 8
238000000034 method Methods 0.000 title claims description 6
239000000126 substance Substances 0.000 title claims description 4
238000004519 manufacturing process Methods 0.000 title description 4
239000004009 herbicide Substances 0.000 title description 3
239000000203 mixture Substances 0.000 claims description 46
-1 C1-C4 alkyl ammonium salt Chemical class 0.000 claims description 40
239000002253 acid Substances 0.000 claims description 38
239000004480 active ingredient Substances 0.000 claims description 37
150000001875 compounds Chemical class 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000002091 cationic group Chemical group 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
150000001408 amides Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 3
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
125000000129 anionic group Chemical group 0.000 claims 1
238000003776 cleavage reaction Methods 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 claims 1
UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
230000007017 scission Effects 0.000 claims 1
241000196324 Embryophyta Species 0.000 description 40
239000013543 active substance Substances 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
239000003921 oil Substances 0.000 description 17
235000019198 oils Nutrition 0.000 description 17
239000000243 solution Substances 0.000 description 17
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 14
230000012010 growth Effects 0.000 description 13
239000004094 surface-active agent Substances 0.000 description 13
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
239000000839 emulsion Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
235000013339 cereals Nutrition 0.000 description 8
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
239000002689 soil Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
150000003863 ammonium salts Chemical class 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000007787 solid Substances 0.000 description 7
239000005995 Aluminium silicate Substances 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
235000012211 aluminium silicate Nutrition 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000008187 granular material Substances 0.000 description 6
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 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
244000038559 crop plants Species 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
230000008635 plant growth Effects 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
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 4
241000209504 Poaceae Species 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
239000012267 brine Substances 0.000 description 4
239000000969 carrier Substances 0.000 description 4
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 4
150000002367 halogens Chemical group 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
238000003756 stirring Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
244000025254 Cannabis sativa Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
239000003480 eluent Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000002736 nonionic surfactant Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000005648 plant growth regulator Substances 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000004576 sand Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene Substances 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
102100037651 AP-2 complex subunit sigma Human genes 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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240000005979 Hordeum vulgare Species 0.000 description 2
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235000019738 Limestone Nutrition 0.000 description 2
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241000209056 Secale Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
244000061456 Solanum tuberosum Species 0.000 description 2
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101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 2
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230000009471 action Effects 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
125000005210 alkyl ammonium group Chemical group 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 2
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239000011575 calcium Substances 0.000 description 2
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235000014113 dietary fatty acids Nutrition 0.000 description 2
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150000002191 fatty alcohols Chemical class 0.000 description 2
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230000009036 growth inhibition Effects 0.000 description 2
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WVYSWPBECUHBMJ-UHFFFAOYSA-N 2-methylprop-1-en-1-ol Chemical compound CC(C)=CO WVYSWPBECUHBMJ-UHFFFAOYSA-N 0.000 description 1
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ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
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229910052740 iodine Inorganic materials 0.000 description 1
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150000002576 ketones Chemical class 0.000 description 1
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238000002156 mixing Methods 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
DHCHPYKGDUYCEB-UHFFFAOYSA-N n-(2-chloroethyl)hydroxylamine Chemical compound ONCCCl DHCHPYKGDUYCEB-UHFFFAOYSA-N 0.000 description 1
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ODHYIQOBTIWVRZ-UHFFFAOYSA-N n-propan-2-ylhydroxylamine Chemical compound CC(C)NO ODHYIQOBTIWVRZ-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
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AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
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239000011591 potassium Substances 0.000 description 1
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239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
239000008262 pumice Substances 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
238000004904 shortening Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
238000004162 soil erosion Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
238000004381 surface treatment Methods 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
239000003760 tallow Substances 0.000 description 1
230000008719 thickening Effects 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical compound CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
238000009966 trimming Methods 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
- 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
- A01N37/42—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 within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
- 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
- A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids

Landscapes

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

CS843771A 1983-05-18 1984-05-18 Herbicide and method of efficient substance production CS243488B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH269383		1983-05-18

Publications (2)

Publication Number	Publication Date
CS377184A2 CS377184A2 (en)	1985-08-15
CS243488B2 true CS243488B2 (en)	1986-06-12

Family

ID=4239451

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS843771A CS243488B2 (en)	1983-05-18	1984-05-18	Herbicide and method of efficient substance production

Country Status (6)

Country	Link
AU (1)	AU583256B2 (es)
CS (1)	CS243488B2 (es)
MX (1)	MX5738A (es)
PA (1)	PA6009501A1 (es)
SU (1)	SU1400503A3 (es)
ZA (1)	ZA843727B (es)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0149588A3 (en) *	1984-01-13	1986-05-07	Sandoz Ag	N-(naphthyl-alkyl)-hydroxylamines
RU2513621C2 (ru) *	2012-07-27	2014-04-20	Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Саратовский государственный университет имени Н.Г. Чернышевского" (СГУ)	Средство, проявляющее росторегулирующую и иммуномодулирующую активность

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2232730A1 (de) *	1972-07-04	1974-01-24	Bayer Ag	Substituierte cyclohexan-2,6-dion-1carbonsaeureanilide und -thioanilide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und fungizide
JPS58164543A (ja) *	1982-03-25	1983-09-29	Ihara Chem Ind Co Ltd	シクロヘキサン誘導体、その製法及びこれを含む植物生長調整剤

1984
- 1984-05-17 SU SU843740550A patent/SU1400503A3/ru active
- 1984-05-17 ZA ZA843727A patent/ZA843727B/xx unknown
- 1984-05-17 MX MX573884A patent/MX5738A/es unknown
- 1984-05-18 CS CS843771A patent/CS243488B2/cs unknown
- 1984-11-14 AU AU35417/84A patent/AU583256B2/en not_active Expired
1992
- 1992-02-11 PA PA19926009501A patent/PA6009501A1/es unknown

Also Published As

Publication number	Publication date
PA6009501A1 (es)	1999-10-25
ZA843727B (en)	1985-01-30
MX5738A (es)	1993-10-01
SU1400503A3 (ru)	1988-05-30
AU3541784A (en)	1986-05-22
AU583256B2 (en)	1989-04-27
CS377184A2 (en)	1985-08-15

Publication	Publication Date	Title
DK166775B1 (da)	1993-07-12	Cyclohexandioncarboxylsyrederivater, fremgangsmaade til deres fremstilling samt deres anvendelse som plantevaekstregulatorer
KR910000524B1 (ko)	1991-01-26	N-알릴설포닐-n'-피리미디닐우레아의 제조방법
AU593097B2 (en)	1990-02-01	Sulfur containing cyclohexanedione derivatives and intermediates thereof
JPS59205368A (ja)	1984-11-20	殺微生物剤
BG60335B2 (bg)	1994-07-25	N-фенилсулфонил-n'-триазинил карбамиди
JPH0228159A (ja)	1990-01-30	複素環式２―アルコキシフエノキシスルホニル尿素類、それらの製造方法およびそれらを含有する除草剤
EP0103537B1 (de)	1987-07-08	N-Arylsulfonyl-N'-triazolylharnstoffe
EP0177450A1 (de)	1986-04-09	Verfahren zur Herstellung von Cyclohexandion-carbonsäurederivaten mit herbizider und das Pflanzenwachstum regulierender Wirkung
EP0156773B1 (de)	1989-09-06	Cyclohexenon-carbonsäurederivate mit herbizider und das Pflanzenwachstum regulierender Wirkung
HU202846B (en)	1991-04-29	Herbicidal and plant growth regulating compositions comprising alkyl- and alkenylsulfonylurea derivatives substituted by heterocyclic group and process for producing the active ingredients
JPS61229890A (ja)	1986-10-14	リン含有官能性酢酸誘導体、その製造方法およびそれらを含有する除草剤および植物生長調整剤
EP0169815A1 (de)	1986-01-29	N-Arylsulfonyl-N'-triazinyl- und -pyrimidinylharnstoffe
CS243488B2 (en)	1986-06-12	Herbicide and method of efficient substance production
SK136493A3 (en)	1994-11-09	Herbicides
EP0046069A1 (en)	1982-02-17	Herbicidal and plant growth regulant diphenylpyridazinones
SK94795A3 (en)	1995-12-06	Pyrazolyl acrylic acid derivatives, intermediates in this method and their use as microbicides
JPH02225472A (ja)	1990-09-07	置換スルホニル尿素および該化合物を含有する除草剤
HU201531B (en)	1990-11-28	Compositions comprising 1,5-diphenyl-1,2,4-triazole-3-carboxylic acid derivatives for the protection of plants against phytotoxic effect of herbicides and process for producing the active ingredients
AU643744B2 (en)	1993-11-25	Pyrimidin-2-ylphenylhydroxylamine derivatives
CH677664A5 (es)	1991-06-14
CS214753B2 (en)	1982-05-28	Fungicide means and method of making the active component
FI56919B (fi)	1980-01-31	Tillvaextregulatorer
EP0476761A1 (en)	1992-03-25	4-substituted isoxazoles
JPH02279677A (ja)	1990-11-15	３―置換アルキルサリチレートを基礎としたフエノキシスルホニル尿素、それらの製造方法およびそれらの除草剤および植物生長調整剤としての使用方法
JPS5940830B2 (ja)	1984-10-03	アニリン誘導体、その製造方法および該化合物を含有する殺微生物剤並びにそれによる防除方法