CH623202A5 - Herbicide containing N,N-disubstituted alanine derivatives - Google Patents

Herbicide containing N,N-disubstituted alanine derivatives Download PDF

Info

Publication number: CH623202A5
Authority: CH; Switzerland
Prior art keywords: group; corresponds; compounds; weight; carbon atoms
Prior art date: 1975-06-30

Application number

CH826476A

Other languages

German (de)

English (en)

Inventor

Ernest Haddock

William John Hopwood

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.)

1975-06-30

Filing date

1976-06-28

Publication date

1981-05-29

1976-06-28 Application filed by Shell Int Research filed Critical Shell Int Research

1981-05-29 Publication of CH623202A5 publication Critical patent/CH623202A5/de

Links

239000004009 herbicide Substances 0.000 title description 8
230000002363 herbicidal effect Effects 0.000 title description 6
150000001294 alanine derivatives Chemical class 0.000 title description 5
150000001875 compounds Chemical group 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
125000004432 carbon atom Chemical group C* 0.000 description 12
-1 Magnesium aluminum silicates Chemical class 0.000 description 11
239000004480 active ingredient Substances 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
241000196324 Embryophyta Species 0.000 description 10
239000003795 chemical substances by application Substances 0.000 description 10
239000002689 soil Substances 0.000 description 10
239000000460 chlorine Substances 0.000 description 9
239000007788 liquid Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
125000002252 acyl group Chemical group 0.000 description 7
239000007787 solid Substances 0.000 description 7
125000000217 alkyl group Chemical group 0.000 description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
238000000034 method Methods 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
239000000243 solution Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
125000004414 alkyl thio group Chemical group 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
244000075850 Avena orientalis Species 0.000 description 3
235000007319 Avena orientalis Nutrition 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
230000035515 penetration Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000002791 soaking Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000005507 spraying Methods 0.000 description 3
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
240000006240 Linum usitatissimum Species 0.000 description 2
235000004431 Linum usitatissimum Nutrition 0.000 description 2
240000003768 Solanum lycopersicum Species 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
239000013543 active substance Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
229910052794 bromium Inorganic materials 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
229910052799 carbon Inorganic materials 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000000969 carrier Substances 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
239000012141 concentrate 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
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000012024 dehydrating agents‎ Substances 0.000 description 2
125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
125000003107 substituted aryl group Chemical group 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000004546 suspension concentrate Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
239000010455 vermiculite Substances 0.000 description 2
229910052902 vermiculite Inorganic materials 0.000 description 2
235000019354 vermiculite Nutrition 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
ZVJBPHMCBRHVEV-UHFFFAOYSA-N 2-hydroxyiminopentan-3-one Chemical compound CCC(=O)C(C)=NO ZVJBPHMCBRHVEV-UHFFFAOYSA-N 0.000 description 1
DGXRGGUNBXNJRI-UHFFFAOYSA-N 2-methyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(C)=C1 DGXRGGUNBXNJRI-UHFFFAOYSA-N 0.000 description 1
NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
235000021533 Beta vulgaris Nutrition 0.000 description 1
241000335053 Beta vulgaris Species 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
235000003351 Brassica cretica Nutrition 0.000 description 1
244000056139 Brassica cretica Species 0.000 description 1
235000003343 Brassica rupestris Nutrition 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
244000089409 Erythrina poeppigiana Species 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
235000007340 Hordeum vulgare Nutrition 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
240000004296 Lolium perenne Species 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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
235000009776 Rathbunia alamosensis Nutrition 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
235000002560 Solanum lycopersicum Nutrition 0.000 description 1
244000062793 Sorghum vulgare Species 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
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
235000007244 Zea mays Nutrition 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 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
235000004279 alanine Nutrition 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
239000010426 asphalt Substances 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 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
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
239000002361 compost Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000007865 diluting Methods 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
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
150000002148 esters Chemical class 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
235000004426 flaxseed Nutrition 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 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
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000011344 liquid material 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
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
239000012184 mineral wax 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
235000010460 mustard Nutrition 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000003415 peat Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
229910052814 silicon oxide Inorganic materials 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
239000000600 sorbitol Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000002426 superphosphate Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH826476A 1975-06-30 1976-06-28 Herbicide containing N,N-disubstituted alanine derivatives CH623202A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB2748275A GB1509034A (en)	1975-06-30	1975-06-30	Herbicides

Publications (1)

Publication Number	Publication Date
CH623202A5 true CH623202A5 (en)	1981-05-29

Family

ID=10260316

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH826476A CH623202A5 (en)	1975-06-30	1976-06-28	Herbicide containing N,N-disubstituted alanine derivatives

Country Status (12)

Country	Link
JP (1)	JPS6058745B2 (ja)
AU (1)	AU510514B2 (ja)
CA (1)	CA1088089A (ja)
CH (1)	CH623202A5 (ja)
DE (1)	DE2628901C2 (ja)
ES (1)	ES449308A1 (ja)
FR (1)	FR2316221A1 (ja)
GB (1)	GB1509034A (ja)
IT (1)	IT1071489B (ja)
NL (1)	NL183398C (ja)
SU (1)	SU803844A3 (ja)
ZA (1)	ZA763841B (ja)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2837863A1 (de) *	1978-09-04	1980-03-13	Ciba Geigy Ag	Oxim-derivate zum schutz von pflanzenkulturen
JP4716091B2 (ja) *	2005-03-28	2011-07-06	コクヨ株式会社	収納装置
CN107954898A (zh) *	2017-12-01	2018-04-24	西北农林科技大学	水杨醛肟酯类化合物及其制备方法、用途

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1289042B (de) *	1965-10-28	1969-02-13	Bayer Ag	Carbamidoxime
DE2234816A1 (de) *	1972-07-13	1974-01-31	Schering Ag	Dichlorbenzaldehydoximcarbonate
DE2262402A1 (de) *	1972-12-15	1974-08-01	Schering Ag	Herbizide phenoxycarbonsaeureoximester

1975
- 1975-06-30 GB GB2748275A patent/GB1509034A/en not_active Expired
1976
- 1976-06-11 CA CA254,661A patent/CA1088089A/en not_active Expired
- 1976-06-28 DE DE19762628901 patent/DE2628901C2/de not_active Expired
- 1976-06-28 IT IT2482376A patent/IT1071489B/it active
- 1976-06-28 ES ES449308A patent/ES449308A1/es not_active Expired
- 1976-06-28 ZA ZA763841A patent/ZA763841B/xx unknown
- 1976-06-28 CH CH826476A patent/CH623202A5/de not_active IP Right Cessation
- 1976-06-28 NL NL7607051A patent/NL183398C/xx not_active IP Right Cessation
- 1976-06-28 JP JP7566776A patent/JPS6058745B2/ja not_active Expired
- 1976-06-28 AU AU15368/76A patent/AU510514B2/en not_active Expired
- 1976-06-28 FR FR7619585A patent/FR2316221A1/fr active Granted
- 1976-06-28 SU SU762376123A patent/SU803844A3/ru active

Also Published As

Publication number	Publication date
IT1071489B (it)	1985-04-10
NL7607051A (nl)	1977-01-03
DE2628901A1 (de)	1977-01-20
NL183398B (nl)	1988-05-16
AU510514B2 (en)	1980-07-03
ZA763841B (en)	1977-05-25
SU803844A3 (ru)	1981-02-07
FR2316221A1 (fr)	1977-01-28
NL183398C (nl)	1988-10-17
DE2628901C2 (de)	1986-01-09
CA1088089A (en)	1980-10-21
GB1509034A (en)	1978-04-26
JPS525726A (en)	1977-01-17
FR2316221B1 (ja)	1979-04-06
ES449308A1 (es)	1977-12-01
AU1536876A (en)	1978-01-05
JPS6058745B2 (ja)	1985-12-21

Legal Events

Date	Code	Title	Description
1991-02-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

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