IE46905B1 - Sulfurous diurethanes - Google Patents

Sulfurous diurethanes

Info

Publication number: IE46905B1
Authority: IE; Ireland
Prior art keywords: carbon atoms; diurethane; formula; phenyl; alkyl
Prior art date: 1977-06-03

Application number

IE1065/78A

Other languages

English (en)

Other versions

IE781065L (en

Original Assignee

Basf 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.)

1977-06-03

Filing date

1978-05-29

Publication date

1983-11-02

1978-05-29 Application filed by Basf Ag filed Critical Basf Ag

1978-12-03 Publication of IE781065L publication Critical patent/IE781065L/xx

1983-11-02 Publication of IE46905B1 publication Critical patent/IE46905B1/en

Links

125000004432 carbon atom Chemical group C* 0.000 claims abstract description 52
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 44
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 11
150000002367 halogens Chemical class 0.000 claims abstract description 10
125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
239000011593 sulfur Substances 0.000 claims abstract description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004122 cyclic group Chemical group 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract description 3
125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
150000001602 bicycloalkyls Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 36
241000196324 Embryophyta Species 0.000 claims description 26
150000002148 esters Chemical class 0.000 claims description 18
239000004480 active ingredient Substances 0.000 claims description 16
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 12
230000002363 herbicidal effect Effects 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
238000011282 treatment Methods 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
235000010469 Glycine max Nutrition 0.000 claims description 6
244000068988 Glycine max Species 0.000 claims description 6
239000004009 herbicide Substances 0.000 claims description 5
241000221079 Euphorbia <genus> Species 0.000 claims description 4
244000098338 Triticum aestivum Species 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
235000003276 Apios tuberosa Nutrition 0.000 claims description 2
235000010777 Arachis hypogaea Nutrition 0.000 claims description 2
244000105624 Arachis hypogaea Species 0.000 claims description 2
235000010744 Arachis villosulicarpa Nutrition 0.000 claims description 2
241000219312 Chenopodium Species 0.000 claims description 2
241000208296 Datura Species 0.000 claims description 2
235000021307 Triticum Nutrition 0.000 claims description 2
240000008042 Zea mays Species 0.000 claims description 2
235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
241000219318 Amaranthus Species 0.000 claims 1
240000007087 Apium graveolens Species 0.000 claims 1
235000015849 Apium graveolens Dulce Group Nutrition 0.000 claims 1
235000010591 Appio Nutrition 0.000 claims 1
244000020518 Carthamus tinctorius Species 0.000 claims 1
235000003255 Carthamus tinctorius Nutrition 0.000 claims 1
241000132570 Centaurea Species 0.000 claims 1
235000007516 Chrysanthemum Nutrition 0.000 claims 1
240000005250 Chrysanthemum indicum Species 0.000 claims 1
244000192528 Chrysanthemum parthenium Species 0.000 claims 1
244000000626 Daucus carota Species 0.000 claims 1
235000002767 Daucus carota Nutrition 0.000 claims 1
235000017945 Matricaria Nutrition 0.000 claims 1
235000007232 Matricaria chamomilla Nutrition 0.000 claims 1
241000221024 Mercurialis Species 0.000 claims 1
241000220261 Sinapis Species 0.000 claims 1
240000006694 Stellaria media Species 0.000 claims 1
NLKPMUCEBRRUOK-UHFFFAOYSA-N ethyl n-anilinocarbamate Chemical compound CCOC(=O)NNC1=CC=CC=C1 NLKPMUCEBRRUOK-UHFFFAOYSA-N 0.000 claims 1
-1 methoxycarbonylmethyl Chemical group 0.000 description 95
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 48
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 22
150000003839 salts Chemical class 0.000 description 19
230000006378 damage Effects 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 11
239000003921 oil Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
244000038559 crop plants Species 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000006185 dispersion Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
150000001408 amides Chemical class 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
238000003756 stirring Methods 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 5
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 5
VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical class CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
210000000056 organ Anatomy 0.000 description 5
239000002689 soil Substances 0.000 description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
235000004357 Mentha x piperita Nutrition 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
125000001246 bromo group Chemical group Br* 0.000 description 4
JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
YSJKYAHYBFJVKV-UHFFFAOYSA-N ethyl n-nitrocarbamate Chemical class CCOC(=O)N[N+]([O-])=O YSJKYAHYBFJVKV-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
239000007787 solid Substances 0.000 description 4
235000013311 vegetables Nutrition 0.000 description 4
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 3
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 3
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 3
125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000335053 Beta vulgaris Species 0.000 description 3
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
240000006122 Chenopodium album Species 0.000 description 3
235000009344 Chenopodium album Nutrition 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
239000004359 castor oil Substances 0.000 description 3
235000019438 castor oil Nutrition 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
150000001913 cyanates Chemical class 0.000 description 3
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
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 3
239000008187 granular material Substances 0.000 description 3
235000012054 meals Nutrition 0.000 description 3
150000002790 naphthalenes Chemical class 0.000 description 3
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 3
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
239000006072 paste Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
241000894007 species Species 0.000 description 3
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
101001053401 Arabidopsis thaliana Acid beta-fructofuranosidase 3, vacuolar Proteins 0.000 description 2
101150065749 Churc1 gene Proteins 0.000 description 2
240000007154 Coffea arabica Species 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
244000299507 Gossypium hirsutum Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
240000003183 Manihot esculenta Species 0.000 description 2
240000004658 Medicago sativa Species 0.000 description 2
244000246386 Mentha pulegium Species 0.000 description 2
235000016257 Mentha pulegium Nutrition 0.000 description 2
241001479543 Mentha x piperita Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
235000002637 Nicotiana tabacum Nutrition 0.000 description 2
244000061176 Nicotiana tabacum Species 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
235000010617 Phaseolus lunatus Nutrition 0.000 description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
244000046052 Phaseolus vulgaris Species 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
235000010582 Pisum sativum Nutrition 0.000 description 2
240000004713 Pisum sativum Species 0.000 description 2
102100038239 Protein Churchill Human genes 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
241001506137 Rapa Species 0.000 description 2
240000006394 Sorghum bicolor Species 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
235000015724 Trifolium pratense Nutrition 0.000 description 2
229920001807 Urea-formaldehyde Polymers 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
159000000007 calcium salts Chemical class 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
239000000969 carrier Substances 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
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 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
235000001050 hortel pimenta Nutrition 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
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 2
229940018564 m-phenylenediamine Drugs 0.000 description 2
150000004988 m-phenylenediamines Chemical class 0.000 description 2
239000000155 melt Substances 0.000 description 2
239000001771 mentha piperita Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
239000004033 plastic Substances 0.000 description 2
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125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
229920000847 nonoxynol Polymers 0.000 description 1
231100001184 nonphytotoxic Toxicity 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
235000011197 perejil Nutrition 0.000 description 1
WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
IXRLLLRWRZSZLT-UHFFFAOYSA-N phenyl n-(3-aminophenyl)carbamate Chemical compound NC1=CC=CC(NC(=O)OC=2C=CC=CC=2)=C1 IXRLLLRWRZSZLT-UHFFFAOYSA-N 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
239000001739 pinus spp. Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
239000012256 powdered iron Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
150000004760 silicates Chemical class 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
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L25/00—Assemblies consisting of a plurality of semiconductor or other solid state devices
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C271/38—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/62—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing three- or four-membered rings
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00

Landscapes

Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Environmental Sciences (AREA)
Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Agronomy & Crop Science (AREA)
Plant Pathology (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Microelectronics & Electronic Packaging (AREA)
Physics & Mathematics (AREA)
Computer Hardware Design (AREA)
Power Engineering (AREA)
General Physics & Mathematics (AREA)
Condensed Matter Physics & Semiconductors (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Polyurethanes Or Polyureas (AREA)

IE1065/78A 1977-06-03 1978-05-29 Sulfurous diurethanes IE46905B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772725146 DE2725146A1 (de)	1977-06-03	1977-06-03	Diurethane und herbizide

Publications (2)

Publication Number	Publication Date
IE781065L IE781065L (en)	1978-12-03
IE46905B1 true IE46905B1 (en)	1983-11-02

Family

ID=6010672

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE1065/78A IE46905B1 (en)	1977-06-03	1978-05-29	Sulfurous diurethanes

Country Status (24)

Country	Link
EP (1)	EP0000030B1 (xx)
JP (1)	JPS543038A (xx)
AT (1)	AT358869B (xx)
AU (1)	AU519196B2 (xx)
BR (1)	BR7803528A (xx)
CA (1)	CA1110264A (xx)
CS (1)	CS196429B2 (xx)
DD (1)	DD135853A5 (xx)
DE (2)	DE2725146A1 (xx)
DK (1)	DK247278A (xx)
ES (1)	ES470367A1 (xx)
FI (1)	FI781762A (xx)
HU (1)	HU177551B (xx)
IE (1)	IE46905B1 (xx)
IL (1)	IL54779A (xx)
IT (1)	IT1104710B (xx)
NO (1)	NO781931L (xx)
NZ (1)	NZ187460A (xx)
PL (1)	PL106564B1 (xx)
PT (1)	PT68091A (xx)
SU (1)	SU725541A3 (xx)
TR (1)	TR20048A (xx)
YU (1)	YU132578A (xx)
ZA (1)	ZA783163B (xx)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3113449A1 (de) *	1981-04-03	1982-11-11	Hoechst Ag, 6000 Frankfurt	"thiocarbaminsaeureester, verfahren zu ihrer herstellung, sie enthaltende arzneimittel und ihre verwendung"
JPS5951205A (ja) *	1982-06-23	1984-03-24	Toyo Soda Mfg Co Ltd	カ−バメ−ト誘導体を含有する除草剤
DE19800531A1 (de) *	1998-01-09	1999-07-15	Bayer Ag	Verfahren zur Herstellung von N-(3-Amino-4-fluor-phenyl)-sulfonsäureamiden, N-(3-Amino-4-fluor-phenyl)-carbonsäureamiden und N-(3-Amino-4-fluor-phenyl)-carbamaten

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1037578B (it) *	1975-04-23	1979-11-20	Snam Progetti	Procedimento per la sintesi di esteri di acidi tiocarbammici
JPS537474A (en) *	1976-07-12	1978-01-23	Tsuneto Yoshii	Process for producing soil conditioner and fertilizers from waste woods of artificial bed log for shiitake* shiitake aseptic timber and other edible or medicinal fungi culture base

1977
- 1977-06-03 DE DE19772725146 patent/DE2725146A1/de not_active Withdrawn
1978
- 1978-05-24 IL IL54779A patent/IL54779A/xx unknown
- 1978-05-26 PT PT197868091A patent/PT68091A/pt unknown
- 1978-05-29 IE IE1065/78A patent/IE46905B1/en unknown
- 1978-05-29 AU AU36576/78A patent/AU519196B2/en not_active Expired
- 1978-05-29 CA CA304,279A patent/CA1110264A/en not_active Expired
- 1978-05-30 TR TR20048A patent/TR20048A/xx unknown
- 1978-05-31 ES ES470367A patent/ES470367A1/es not_active Expired
- 1978-06-01 DD DD78205730A patent/DD135853A5/xx unknown
- 1978-06-01 DE DE7878100050T patent/DE2860287D1/de not_active Expired
- 1978-06-01 EP EP78100050A patent/EP0000030B1/de not_active Expired
- 1978-06-01 CS CS783577A patent/CS196429B2/cs unknown
- 1978-06-01 PL PL1978207278A patent/PL106564B1/xx unknown
- 1978-06-01 SU SU782619253A patent/SU725541A3/ru active
- 1978-06-01 BR BR787803528A patent/BR7803528A/pt unknown
- 1978-06-02 YU YU01325/78A patent/YU132578A/xx unknown
- 1978-06-02 NO NO781931A patent/NO781931L/no unknown
- 1978-06-02 IT IT49686/78A patent/IT1104710B/it active
- 1978-06-02 AT AT403178A patent/AT358869B/de not_active IP Right Cessation
- 1978-06-02 HU HU78BA3662A patent/HU177551B/hu unknown
- 1978-06-02 ZA ZA00783163A patent/ZA783163B/xx unknown
- 1978-06-02 DK DK247278A patent/DK247278A/da not_active Application Discontinuation
- 1978-06-02 FI FI781762A patent/FI781762A/fi not_active Application Discontinuation
- 1978-06-02 NZ NZ187460A patent/NZ187460A/xx unknown
- 1978-06-02 JP JP6587678A patent/JPS543038A/ja active Granted

Also Published As

Publication number	Publication date
ES470367A1 (es)	1979-09-16
EP0000030B1 (de)	1980-12-10
DK247278A (da)	1978-12-04
YU132578A (en)	1983-01-21
PL207278A1 (pl)	1979-03-26
DE2725146A1 (de)	1978-12-14
IL54779A (en)	1982-12-31
AU519196B2 (en)	1981-11-19
CS196429B2 (en)	1980-03-31
JPS543038A (en)	1979-01-11
ATA403178A (de)	1980-02-15
DE2860287D1 (en)	1981-02-19
CA1110264A (en)	1981-10-06
PT68091A (fr)	1978-05-31
IE781065L (en)	1978-12-03
FI781762A (fi)	1978-12-04
ZA783163B (en)	1979-07-25
SU725541A1 (ru)	1980-03-30
EP0000030A1 (de)	1978-12-20
PL106564B1 (pl)	1979-12-31
BR7803528A (pt)	1979-02-20
SU725541A3 (en)	1980-03-30
IT7849686A0 (it)	1978-06-02
NZ187460A (en)	1980-11-28
NO781931L (no)	1978-12-05
TR20048A (tr)	1980-07-02
JPS6151583B2 (xx)	1986-11-10
DD135853A5 (de)	1979-06-06
IL54779A0 (en)	1978-07-31
AU3657678A (en)	1979-12-06
AT358869B (de)	1980-10-10
HU177551B (en)	1981-11-28
IT1104710B (it)	1985-10-28

Publication	Publication Date	Title
US4354031A (en)	1982-10-12	Substituted 3-aminopyrazoles
EP0559814B1 (de)	1998-09-09	Herbizide n- (1,3,5-triazin-2-yl)aminocarbonyl]benzolsulfonamide
US5071470A (en)	1991-12-10	Herbicidal 1,3,5-triazin-2-ylaminocarbonylamino-sulfonylbenzoic esters
US4500340A (en)	1985-02-19	Urea derivatives and their use for controlling undesirable plant growth
CA1120942A (en)	1982-03-30	.sup.m-anilide-urethanes
CS196228B2 (en)	1980-03-31	Herbicide
IE46905B1 (en)	1983-11-02	Sulfurous diurethanes
US4428766A (en)	1984-01-31	2N-1,2,4,6,Thiatriazine-1,1-dioxides and their use for controlling undesirable plant growth
US4566900A (en)	1986-01-28	Aniline derivatives and their use for controlling undesirable plant growth
CA2007394A1 (en)	1990-07-16	Thiophene-2-carboxylic acid derivatives, their preparation and their use for controlling undesirable plant growth
US4518414A (en)	1985-05-21	Thiadiazole derivatives and their use for controlling undesirable plant growth
US4426219A (en)	1984-01-17	2H-1,2,4,6-Thiatriazine-1-dioxides and their use for controlling undesirable plant growth
US4283547A (en)	1981-08-11	Parabanic acid derivatives
US5069710A (en)	1991-12-03	N-((6-trifluoromethylpyrimidin-2-yl)-aminocarbonyl)-2-carboalkoxybenzenesulfonamides
CA1269987A (en)	1990-06-05	Thiazolylamides, their preparation, and their use for controlling undesirable plant growth
US4472191A (en)	1984-09-18	1,2,4,6-Thiatriazine-1,1-dioxides and their use for controlling undesirable plant growth
US5001261A (en)	1991-03-19	Cyclohexenone derivatives and their use for controlling undesirable plant growth
CA2022332A1 (en)	1991-01-27	Cinnamic esters
US4226613A (en)	1980-10-07	Bisthiocarbamic acid esters and herbicidal use thereof
US4131751A (en)	1978-12-26	Diurethanes
US4124591A (en)	1978-11-07	Isoxazolylmethylthiol carbamates
AU644291B1 (en)	1993-12-02	Herbicidal N-{(1,3,5-triazin-2-yl)-aminocarbonyl}- benzenesulfonamides
US4588434A (en)	1986-05-13	Substituted ureas and their use for controlling undesirable plant growth
US4498922A (en)	1985-02-12	N-aminomethylhaloacetanilides and their use for controlling undesirable plant growth
US4889554A (en)	1989-12-26	Diphenyl ether derivatives, their preparation and their use for controlling undesirable plant growth