IL43282A - N,n,n'-trimethyl-n'-(5-substituted-1,3,4-thiadiazol-2-yl)-ureas having selective herbicidal activity - Google Patents
N,n,n'-trimethyl-n'-(5-substituted-1,3,4-thiadiazol-2-yl)-ureas having selective herbicidal activityInfo
- Publication number
- IL43282A IL43282A IL43282A IL4328273A IL43282A IL 43282 A IL43282 A IL 43282A IL 43282 A IL43282 A IL 43282A IL 4328273 A IL4328273 A IL 4328273A IL 43282 A IL43282 A IL 43282A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- general formula
- urea
- tr1methyl
- th1ad1azol
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 64
- 238000000034 method Methods 0.000 claims description 25
- 239000004202 carbamide Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 241000196324 Embryophyta Species 0.000 claims description 11
- -1 azol -2-yl Chemical group 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000010410 dusting Methods 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 150000007530 organic bases Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000005507 spraying Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 2
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 150000001726 carbonic acid ester halides Chemical class 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000002432 hydroperoxides Chemical class 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 9
- 244000061456 Solanum tuberosum Species 0.000 description 7
- 235000002595 Solanum tuberosum Nutrition 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 241000205407 Polygonum Species 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 235000012015 potatoes Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000009333 weeding Methods 0.000 description 3
- HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- QWRKJGZSKUIQDA-UHFFFAOYSA-N 4,4-dimethyl-2-methylidenecyclohexan-1-one Chemical compound CC1(C)CCC(=O)C(=C)C1 QWRKJGZSKUIQDA-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZBVXYFSFFTWFPF-UHFFFAOYSA-N C1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)O.[Ca] Chemical compound C1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)O.[Ca] ZBVXYFSFFTWFPF-UHFFFAOYSA-N 0.000 description 1
- JYDBRPNBUACOAC-UHFFFAOYSA-N C=C(Cl)Cl.CC1=CC=CC=C1 Chemical compound C=C(Cl)Cl.CC1=CC=CC=C1 JYDBRPNBUACOAC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
- 235000019738 Limestone Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 244000042664 Matricaria chamomilla Species 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 241000722118 Thlaspi Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004651 carbonic acid esters Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- YEXIGDOOPPENOC-UHFFFAOYSA-N phenyl hydrogen carbonate;hydrochloride Chemical compound Cl.OC(=O)OC1=CC=CC=C1 YEXIGDOOPPENOC-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2246461A DE2246461C2 (de) | 1972-09-21 | 1972-09-21 | 1,1,3-Trimethyl-3-(5-Butylsulfonyl-1,3,4-thiadiazol-2-yl)-harnstoff und herbizide Mittel enthaltend diese Verbindung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43282A0 IL43282A0 (en) | 1973-11-28 |
| IL43282A true IL43282A (en) | 1976-07-30 |
Family
ID=5857018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43282A IL43282A (en) | 1972-09-21 | 1973-09-21 | N,n,n'-trimethyl-n'-(5-substituted-1,3,4-thiadiazol-2-yl)-ureas having selective herbicidal activity |
Country Status (28)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2607481A1 (de) * | 1976-02-20 | 1977-08-25 | Schering Ag | 2-dimethylcarbamoylimino-1,3,4- thiadiazolin-3-id-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
| ZA775225B (en) * | 1977-08-29 | 1978-03-29 | Lilly Co Eli | Herbicidal combinations |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1195672A (en) * | 1968-02-01 | 1970-06-17 | Mobil Oil Corp | Novel Urea Derivatives and Herbicides containing the same |
| CH513585A (de) * | 1969-07-18 | 1971-10-15 | Agripat Sa | Herbizides Mittel |
| DE2028778A1 (en) * | 1970-06-06 | 1971-12-23 | Thiadiazolyl-urea herbicides - 5 - substd by sulphinyl or sulphonyl | |
| ES393478A1 (es) * | 1970-09-03 | 1974-10-01 | Schering Ag | Procedimiento para la preparacion de herbicidas. |
| DE2044442C2 (de) * | 1970-09-03 | 1983-11-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1,1,3-Trimethyl-3-(-5-Äthylsulfonyl-1,3,4-Thiadiazol-2-yl)-Harnstoff mit herbizider Wirkung |
-
1972
- 1972-09-21 DE DE2246461A patent/DE2246461C2/de not_active Expired
-
1973
- 1973-07-19 TR TR18582A patent/TR18582A/xx unknown
- 1973-08-06 DD DD172728A patent/DD105111A5/xx unknown
- 1973-08-08 CS CS5617A patent/CS169847B2/cs unknown
- 1973-08-20 GB GB3928973A patent/GB1454796A/en not_active Expired
- 1973-08-21 DK DK461073A patent/DK132024C/da not_active IP Right Cessation
- 1973-08-27 YU YU2283/73A patent/YU34885B/xx unknown
- 1973-08-29 BG BG025350A patent/BG22783A3/xx unknown
- 1973-08-29 BG BG024413A patent/BG22780A3/xx unknown
- 1973-08-30 IE IE01539/73A patent/IE39006B1/xx unknown
- 1973-09-03 HU HUSE000442 patent/HU167875B/hu unknown
- 1973-09-04 ES ES418476A patent/ES418476A1/es not_active Expired
- 1973-09-17 FI FI2891/73A patent/FI56177C/fi active
- 1973-09-19 CA CA181,436A patent/CA1008454A/en not_active Expired
- 1973-09-19 LU LU68455A patent/LU68455A1/xx unknown
- 1973-09-20 NO NO3685/73A patent/NO139605C/no unknown
- 1973-09-20 SE SE7312828A patent/SE396384B/xx unknown
- 1973-09-20 FR FR7333734A patent/FR2200272B1/fr not_active Expired
- 1973-09-20 PL PL1973165325A patent/PL84425B1/pl unknown
- 1973-09-20 SU SU1961452A patent/SU559616A3/ru active
- 1973-09-21 CH CH1361673A patent/CH586009A5/xx not_active IP Right Cessation
- 1973-09-21 IT IT29215/73A patent/IT995462B/it active
- 1973-09-21 RO RO7376133A patent/RO78370A/ro unknown
- 1973-09-21 BE BE135913A patent/BE805165A/xx not_active IP Right Cessation
- 1973-09-21 JP JP10682073A patent/JPS565722B2/ja not_active Expired
- 1973-09-21 AT AT815073A patent/AT326945B/de not_active IP Right Cessation
- 1973-09-21 IL IL43282A patent/IL43282A/en unknown
- 1973-09-21 ZA ZA737492*A patent/ZA737492B/xx unknown
- 1973-09-21 NL NL7313046A patent/NL7313046A/xx not_active Application Discontinuation
-
1974
- 1974-05-07 SU SU2021991A patent/SU559645A3/ru active
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