CS254967B2 - Herbicide and method of its efficient component production - Google Patents

Herbicide and method of its efficient component production Download PDF

Info

Publication number: CS254967B2
Authority: CS; Czechoslovakia
Prior art keywords: group; formula; methyl; active ingredient; urea derivative
Prior art date: 1982-06-25

Application number

CS834635A

Other languages

Czech (cs)

English (en)

Other versions

CS463583A2 (en

Inventor

Helden Robert Van

Johannes L M Syrier

Frank Baardmann

Original Assignee

Shell Int Research

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.)

1982-06-25

Filing date

1983-06-23

Publication date

1988-02-15

1983-06-23 Application filed by Shell Int Research filed Critical Shell Int Research

1987-07-16 Publication of CS463583A2 publication Critical patent/CS463583A2/cs

1988-02-15 Publication of CS254967B2 publication Critical patent/CS254967B2/cs

Links

230000002363 herbicidal effect Effects 0.000 title claims abstract description 20
238000000034 method Methods 0.000 title claims description 20
239000004009 herbicide Substances 0.000 title claims 2
238000004519 manufacturing process Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 35
-1 R3 represents H Chemical group 0.000 claims abstract description 34
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
239000001257 hydrogen Substances 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
125000005843 halogen group Chemical group 0.000 claims abstract description 5
239000000203 mixture Substances 0.000 claims description 45
239000004480 active ingredient Substances 0.000 claims description 18
150000003672 ureas Chemical class 0.000 claims description 14
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000001118 alkylidene group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
239000004927 clay Substances 0.000 claims 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 8
125000001424 substituent group Chemical group 0.000 abstract description 7
150000002148 esters Chemical class 0.000 abstract description 3
150000001298 alcohols Chemical class 0.000 abstract description 2
150000004703 alkoxides Chemical class 0.000 abstract 1
125000004429 atom Chemical group 0.000 abstract 1
150000004292 cyclic ethers Chemical class 0.000 abstract 1
150000002009 diols Chemical class 0.000 abstract 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000002689 soil Substances 0.000 description 14
239000007787 solid Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
241000196324 Embryophyta Species 0.000 description 9
239000000047 product Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
238000005984 hydrogenation reaction Methods 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
230000003197 catalytic effect Effects 0.000 description 7
238000001914 filtration Methods 0.000 description 7
239000007788 liquid Substances 0.000 description 7
239000003921 oil Substances 0.000 description 7
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
239000000843 powder Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000012876 carrier material Substances 0.000 description 6
HHGRETZRHZRXQQ-UHFFFAOYSA-N 2-(2-methyl-4-nitrophenyl)propane-1,3-diol Chemical compound CC1=CC([N+]([O-])=O)=CC=C1C(CO)CO HHGRETZRHZRXQQ-UHFFFAOYSA-N 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000004094 surface-active agent Substances 0.000 description 5
HOJIBSGTGYEHGS-UHFFFAOYSA-N 2-(4-amino-2-methylphenyl)propane-1,3-diol Chemical compound CC1=CC(N)=CC=C1C(CO)CO HOJIBSGTGYEHGS-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000000654 additive Substances 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000007859 condensation product Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
239000012047 saturated solution Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
229930040373 Paraformaldehyde Natural products 0.000 description 3
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
229960000892 attapulgite Drugs 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
229910052625 palygorskite Inorganic materials 0.000 description 3
229920002866 paraformaldehyde Polymers 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000010455 vermiculite Substances 0.000 description 3
229910052902 vermiculite Inorganic materials 0.000 description 3
235000019354 vermiculite Nutrition 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical class NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
VXUUTOSGQSJWAV-UHFFFAOYSA-N 4-(1,5-dioxaspiro[5.5]undecan-3-yl)-3-methylaniline Chemical compound CC1=CC(N)=CC=C1C1COC2(CCCCC2)OC1 VXUUTOSGQSJWAV-UHFFFAOYSA-N 0.000 description 2
DQMMOSANDJRVCU-UHFFFAOYSA-N 5-(2-methyl-4-nitrophenyl)-1,3-dioxane Chemical compound CC1=CC([N+]([O-])=O)=CC=C1C1COCOC1 DQMMOSANDJRVCU-UHFFFAOYSA-N 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
235000007319 Avena orientalis Nutrition 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
150000007514 bases Chemical class 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
238000007865 diluting Methods 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001030 gas--liquid chromatography Methods 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000012433 hydrogen halide Substances 0.000 description 2
229910000039 hydrogen halide Inorganic materials 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
150000004760 silicates Chemical class 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
241000894007 species Species 0.000 description 2
239000007921 spray Substances 0.000 description 2
238000005507 spraying Methods 0.000 description 2
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AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
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SJAMUIJYIGYHGZ-UHFFFAOYSA-N 3-(2-methyl-4-nitrophenyl)-1,5-dioxaspiro[5.5]undecane Chemical compound CC1=CC([N+]([O-])=O)=CC=C1C1COC2(CCCCC2)OC1 SJAMUIJYIGYHGZ-UHFFFAOYSA-N 0.000 description 1
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239000004215 Carbon black (E152) Substances 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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244000060234 Gmelina philippensis Species 0.000 description 1
101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 1
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239000005909 Kieselgur Substances 0.000 description 1
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240000006240 Linum usitatissimum Species 0.000 description 1
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NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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244000088461 Panicum crus-galli Species 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
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229910006124 SOCl2 Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
229920013817 TRITON X-155 Polymers 0.000 description 1
102100029645 UBX domain-containing protein 11 Human genes 0.000 description 1
235000007244 Zea mays Nutrition 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
XIZDZULXFFHQTJ-UHFFFAOYSA-N [2-(4-amino-2-methylphenyl)-3-hydroxypropyl] hydrogen sulfite Chemical compound S(=O)(O)OCC(CO)C1=C(C=C(C=C1)N)C XIZDZULXFFHQTJ-UHFFFAOYSA-N 0.000 description 1
UTTLAJSRXYTQIM-UHFFFAOYSA-N [3-hydroxy-2-(2-methyl-4-nitrophenyl)propyl] hydrogen sulfite Chemical compound CC1=CC([N+]([O-])=O)=CC=C1C(CO)COS(O)=O UTTLAJSRXYTQIM-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007798 antifreeze agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000010426 asphalt Substances 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical class [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
PWAPCRSSMCLZHG-UHFFFAOYSA-N cyclopentylidene Chemical group [C]1CCCC1 PWAPCRSSMCLZHG-UHFFFAOYSA-N 0.000 description 1
101150047356 dec-1 gene Proteins 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000004426 flaxseed Nutrition 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
235000012243 magnesium silicates Nutrition 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
239000008268 mayonnaise Substances 0.000 description 1
235000010746 mayonnaise Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
239000003607 modifier Substances 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000002426 superphosphate Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000004546 suspension concentrate Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/19—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/34—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/10—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms two oxygen atoms and one sulfur atom, e.g. cyclic sulfates

Landscapes

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

CS834635A 1982-06-25 1983-06-23 Herbicide and method of its efficient component production CS254967B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8218455		1982-06-25
GB8220141		1982-07-12

Publications (2)

Publication Number	Publication Date
CS463583A2 CS463583A2 (en)	1987-07-16
CS254967B2 true CS254967B2 (en)	1988-02-15

Family

ID=26283178

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS834635A CS254967B2 (en)	1982-06-25	1983-06-23	Herbicide and method of its efficient component production

Country Status (14)

Country	Link
US (1)	US4533379A (pl)
EP (1)	EP0097980B1 (pl)
AU (1)	AU558119B2 (pl)
BR (1)	BR8303346A (pl)
CS (1)	CS254967B2 (pl)
DD (1)	DD209960A5 (pl)
DE (1)	DE3375012D1 (pl)
DK (1)	DK291483A (pl)
ES (1)	ES8503647A1 (pl)
GR (1)	GR77520B (pl)
HU (1)	HU191857B (pl)
NZ (1)	NZ204682A (pl)
PL (1)	PL140009B1 (pl)
TR (1)	TR21867A (pl)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8411326D0 (en) *	1984-05-03	1984-06-06	Shell Int Research	Anilide herbicides

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2655444A (en) *	1952-02-14	1953-10-13	Du Pont	3-(halophenyl)-1, 1-dialkyl ureas and weed control compositions and methods
US2655447A (en) *	1952-02-14	1953-10-13	Du Pont	Composition and method
DE1214473B (de) *	1963-10-18	1966-04-14	Basf Ag	Herbizid
DE1545820A1 (de) *	1965-06-03	1969-12-11	Hoechst Ag	Verfahren zur Herstellung von 3,1-Benzothiazin-Derivaten
US3781305A (en) *	1971-10-26	1973-12-25	Stauffer Chemical Co	Substituted ureido dioxolanes and dioxanes and their utility as herbicides
US4063025A (en) *	1975-02-05	1977-12-13	Yamanouchi Pharmaceutical Co., Ltd.	4-Substituted amino-α-aminomethylbenzyl alcohol derivatives
JPS54122252A (en) *	1978-03-13	1979-09-21	Sumitomo Chem Co Ltd	Substitued phenylurea derivative, its preparation, and herbicide containing the same

1983
- 1983-05-27 EP EP83200758A patent/EP0097980B1/en not_active Expired
- 1983-05-27 DE DE8383200758T patent/DE3375012D1/de not_active Expired
- 1983-06-14 US US06/504,349 patent/US4533379A/en not_active Expired - Fee Related
- 1983-06-20 DD DD83252168A patent/DD209960A5/de not_active IP Right Cessation
- 1983-06-23 HU HU832230A patent/HU191857B/hu not_active IP Right Cessation
- 1983-06-23 CS CS834635A patent/CS254967B2/cs unknown
- 1983-06-23 AU AU16174/83A patent/AU558119B2/en not_active Ceased
- 1983-06-23 NZ NZ204682A patent/NZ204682A/en unknown
- 1983-06-23 ES ES523537A patent/ES8503647A1/es not_active Expired
- 1983-06-23 PL PL1983242654A patent/PL140009B1/pl unknown
- 1983-06-23 BR BR8303346A patent/BR8303346A/pt unknown
- 1983-06-23 TR TR21867A patent/TR21867A/xx unknown
- 1983-06-23 GR GR71767A patent/GR77520B/el unknown
- 1983-06-23 DK DK291483A patent/DK291483A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
PL140009B1 (en)	1987-03-31
TR21867A (tr)	1985-01-01
EP0097980A3 (en)	1985-04-17
DE3375012D1 (en)	1988-02-04
DK291483D0 (da)	1983-06-23
PL242654A1 (en)	1985-03-12
AU558119B2 (en)	1987-01-22
EP0097980B1 (en)	1987-12-23
GR77520B (pl)	1984-09-24
NZ204682A (en)	1986-10-08
DK291483A (da)	1983-12-26
HU191857B (en)	1987-04-28
CS463583A2 (en)	1987-07-16
ES523537A0 (es)	1985-03-01
ES8503647A1 (es)	1985-03-01
DD209960A5 (de)	1984-05-30
AU1617483A (en)	1984-01-05
EP0097980A2 (en)	1984-01-11
US4533379A (en)	1985-08-06
BR8303346A (pt)	1984-02-07

Publication	Publication Date	Title
US4249937A (en)	1981-02-10	Cyclohexane derivatives
US4227009A (en)	1980-10-07	Phenoxyphenoxy-propionic acid derivatives
US4175947A (en)	1979-11-27	Phenoxy-phenoxypropionic acid esters
EP0161019A1 (en)	1985-11-13	Pesticidal benzoylurea compounds
BG61516B2 (bg)	1997-10-31	Пропинилов естер на 2-/4-(5-хлоро-3-флуоропиридин-2-илокси) фенокси/-пропионовата киселина и приложението й
US4927824A (en)	1990-05-22	Fungicidal trisubstituted 1,3,5-triazine-2,4,6-triones
CS223978B2 (en)	1983-11-25	Herbicide means
JPH01207281A (ja)	1989-08-21	イミノフエニルチアゾリジン、調製方法及び使用法
CS246090B2 (en)	1986-10-16	Insecticide and method of its efficient component production
CA1250588A (en)	1989-02-28	Diphenyl ether cyclic imine derivatives
CA1250300A (en)	1989-02-21	Ether herbicides
CS254967B2 (en)	1988-02-15	Herbicide and method of its efficient component production
US3981914A (en)	1976-09-21	N-alkylsulfonylperfluoroalkanesulfonanilides
CZ279452B6 (cs)	1995-05-17	Způsob výroby oximinoetherových sloučenin
KR920005411B1 (ko)	1992-07-03	치환된 테트라졸의 제법
EP0171853B1 (en)	1989-03-22	Pesticidal benzoylurea compounds
CS231991B2 (en)	1985-01-16	Herbceous agent and manufacturing process of active substances
US4358611A (en)	1982-11-09	Preparation of 2-phenylsemicarbazides
EP0103918B1 (en)	1987-07-29	Pesticidal benzoylurea compounds
US4108399A (en)	1978-08-22	Herbicidal semicarbazones
US4226612A (en)	1980-10-07	Certain herbicidal (2-oxo-3-oxazolidinyl)phenylureas
EP0216423B1 (en)	1993-05-12	Pesticidal benzoylurea compounds
EP0184256B1 (en)	1989-10-18	Diphenyl ether herbicides
EP0227157B1 (en)	1990-04-11	Herbicides
US4345077A (en)	1982-08-17	Certain herbicidal N-(meta-(6-chloro-3-pyridazinyloxy)phenyl)trifluoromethanesulfonamides