IL25486A - Derivatives of 2,6-dichlorothiobenzamide,their preparation and use - Google Patents
Derivatives of 2,6-dichlorothiobenzamide,their preparation and useInfo
- Publication number
- IL25486A IL25486A IL25486A IL2548666A IL25486A IL 25486 A IL25486 A IL 25486A IL 25486 A IL25486 A IL 25486A IL 2548666 A IL2548666 A IL 2548666A IL 25486 A IL25486 A IL 25486A
- Authority
- IL
- Israel
- Prior art keywords
- dichlorothiobenzimidate
- toluenesulphonate
- methyl
- alkyl
- compounds
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 15
- KGKGSIUWJCAFPX-UHFFFAOYSA-N 2,6-dichlorothiobenzamide Chemical class NC(=S)C1=C(Cl)C=CC=C1Cl KGKGSIUWJCAFPX-UHFFFAOYSA-N 0.000 title claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 26
- -1 alkaryl sulphate Chemical compound 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 14
- 239000004094 surface-active agent Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 241000196324 Embryophyta Species 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 230000002363 herbicidal effect Effects 0.000 claims description 7
- 239000012429 reaction media Substances 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 5
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 239000004563 wettable powder Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- PNBZRWNZOYWPEF-UHFFFAOYSA-N CS(=O)(=O)O.C(CCC)SC(C1=C(C=CC=C1Cl)Cl)=N Chemical compound CS(=O)(=O)O.C(CCC)SC(C1=C(C=CC=C1Cl)Cl)=N PNBZRWNZOYWPEF-UHFFFAOYSA-N 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims description 2
- 239000000428 dust Substances 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- IBYWXHXYSXXXSX-UHFFFAOYSA-N methyl 2,6-dichlorobenzenecarboximidothioate methyl hydrogen sulfate Chemical compound S(=O)(=O)(OC)O.CSC(C1=C(C=CC=C1Cl)Cl)=N IBYWXHXYSXXXSX-UHFFFAOYSA-N 0.000 claims description 2
- OSEWOKHOLUGDES-UHFFFAOYSA-N 2-chloroethyl 2,6-dichlorobenzenecarboximidothioate 4-methylbenzenesulfonic acid Chemical compound C1(=CC=C(C=C1)S(=O)(=O)O)C.ClCCSC(C1=C(C=CC=C1Cl)Cl)=N OSEWOKHOLUGDES-UHFFFAOYSA-N 0.000 claims 1
- BGUJALDZOYDCEP-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)SC(C1=C(C=CC=C1Cl)Cl)=N Chemical compound C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)SC(C1=C(C=CC=C1Cl)Cl)=N BGUJALDZOYDCEP-UHFFFAOYSA-N 0.000 claims 1
- CPJKUTHBUBQPIO-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)O)C.C(CC)SC(C1=C(C=CC=C1Cl)Cl)=N Chemical compound C1(=CC=C(C=C1)S(=O)(=O)O)C.C(CC)SC(C1=C(C=CC=C1Cl)Cl)=N CPJKUTHBUBQPIO-UHFFFAOYSA-N 0.000 claims 1
- DRXYNMGQJQRONW-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)O)C.C(CCC)SC(C1=C(C=CC=C1Cl)Cl)=N Chemical compound C1(=CC=C(C=C1)S(=O)(=O)O)C.C(CCC)SC(C1=C(C=CC=C1Cl)Cl)=N DRXYNMGQJQRONW-UHFFFAOYSA-N 0.000 claims 1
- RWOURSOGGAYDHU-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)O)C.ClCCCSC(C1=C(C=CC=C1Cl)Cl)=N Chemical compound C1(=CC=C(C=C1)S(=O)(=O)O)C.ClCCCSC(C1=C(C=CC=C1Cl)Cl)=N RWOURSOGGAYDHU-UHFFFAOYSA-N 0.000 claims 1
- QQBCGGJJWIPJMI-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)O.C(CCC)SC(C1=C(C=CC=C1Cl)Cl)=N Chemical compound C1(=CC=CC=C1)S(=O)(=O)O.C(CCC)SC(C1=C(C=CC=C1Cl)Cl)=N QQBCGGJJWIPJMI-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- TYKUNHIUCWPJHW-UHFFFAOYSA-N benzenesulfonic acid methyl 2,6-dichlorobenzenecarboximidothioate Chemical compound C1(=CC=CC=C1)S(=O)(=O)O.CSC(C1=C(C=CC=C1Cl)Cl)=N TYKUNHIUCWPJHW-UHFFFAOYSA-N 0.000 claims 1
- QULJGQSJZXYPPZ-UHFFFAOYSA-N ethanesulfonic acid methyl 2,6-dichlorobenzenecarboximidothioate Chemical compound C(C)S(=O)(=O)O.CSC(C1=C(C=CC=C1Cl)Cl)=N QULJGQSJZXYPPZ-UHFFFAOYSA-N 0.000 claims 1
- WBBVEZYWYGLWMF-UHFFFAOYSA-N ethyl 2,6-dichlorobenzenecarboximidothioate ethyl hydrogen sulfate Chemical compound S(=O)(=O)(OCC)O.C(C)SC(C1=C(C=CC=C1Cl)Cl)=N WBBVEZYWYGLWMF-UHFFFAOYSA-N 0.000 claims 1
- HKXBQMXNWFVXQS-UHFFFAOYSA-N ethyl 2,6-dichlorobenzenecarboximidothioate methanesulfonic acid Chemical compound CS(=O)(=O)O.C(C)SC(C1=C(C=CC=C1Cl)Cl)=N HKXBQMXNWFVXQS-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 241000482268 Zea mays subsp. mays Species 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 239000004615 ingredient Substances 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
- 239000007788 liquid Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- ZXNMIUJDTOMBPV-UHFFFAOYSA-N 2-chloroethyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCCl)C=C1 ZXNMIUJDTOMBPV-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- MKKXPYBWCIOEJK-UHFFFAOYSA-N C[SH2]C(C(C(Cl)=CC=C1)=C1Cl)=N Chemical compound C[SH2]C(C(C(Cl)=CC=C1)=C1Cl)=N MKKXPYBWCIOEJK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- LFLBHTZRLVHUQC-UHFFFAOYSA-N butyl methanesulfonate Chemical compound CCCCOS(C)(=O)=O LFLBHTZRLVHUQC-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 125000001145 hydrido group Chemical class *[H] 0.000 description 1
- KETHQOOVMIVLCH-UHFFFAOYSA-N hydron;nonyl sulfate Chemical compound CCCCCCCCCOS(O)(=O)=O KETHQOOVMIVLCH-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- YLJRCXSSKLWCDE-UHFFFAOYSA-N methyl ethanesulfonate Chemical compound CCS(=O)(=O)OC YLJRCXSSKLWCDE-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- IVNFTPCOZIGNAE-UHFFFAOYSA-N propan-2-yl hydrogen sulfate Chemical compound CC(C)OS(O)(=O)=O IVNFTPCOZIGNAE-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 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
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/06—Hydrogenosulfates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/04—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
- C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/58—Derivatives of thiocarboxylic acids, the doubly-bound oxygen atoms being replaced by nitrogen atoms, e.g. imino-thio ethers
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB13845/65A GB1039459A (en) | 1965-04-01 | 1965-04-01 | Novel derivatives of 2,6-dichlorothiobenzamide, methods for their preparation, and herbicidal compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL25486A true IL25486A (en) | 1969-07-30 |
Family
ID=10030383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL25486A IL25486A (en) | 1965-04-01 | 1966-03-30 | Derivatives of 2,6-dichlorothiobenzamide,their preparation and use |
Country Status (10)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4131449A (en) * | 1977-10-17 | 1978-12-26 | Shell Oil Company | Propanimidothioic acid derivatives |
| BR9804865B1 (pt) * | 1997-04-24 | 2011-08-23 | pesticida 3-(fenil substituìdo)-5-(tienil ou furil)-1,2,4-triazóis, composição para controlar insetos ou ácaros, bem como processo para controlar insetos, ácaros, moscas brancas e afìdios, para proteger plantas de afìdios, ácaros ou insetos. | |
| EP1123291B1 (en) * | 1998-10-23 | 2007-07-18 | Dow Agrosciences LLC | Process for preparing 3-(substituted phenyl)-5-thienyl or furyl)-1,2,4-triazoles and novel intermediates utilized therein |
-
1965
- 1965-04-01 GB GB13845/65A patent/GB1039459A/en not_active Expired
-
1966
- 1966-03-30 SE SE04244/66A patent/SE325873B/xx unknown
- 1966-03-30 BE BE678687D patent/BE678687A/xx unknown
- 1966-03-30 ES ES0324901A patent/ES324901A1/es not_active Expired
- 1966-03-30 CH CH461066A patent/CH489997A/de not_active IP Right Cessation
- 1966-03-30 DK DK166066AA patent/DK120128B/da unknown
- 1966-03-30 FI FI660815A patent/FI44605C/fi active
- 1966-03-30 DE DE19661567130 patent/DE1567130A1/de active Pending
- 1966-03-30 IL IL25486A patent/IL25486A/en unknown
- 1966-03-31 NL NL6604251A patent/NL6604251A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1039459A (en) | 1966-08-17 |
| NL6604251A (US06486227-20021126-C00005.png) | 1966-10-03 |
| SE325873B (US06486227-20021126-C00005.png) | 1970-07-13 |
| CH489997A (de) | 1970-05-15 |
| FI44605B (US06486227-20021126-C00005.png) | 1971-08-31 |
| DE1567130A1 (de) | 1970-07-23 |
| DK120128B (da) | 1971-04-13 |
| BE678687A (US06486227-20021126-C00005.png) | 1966-09-30 |
| ES324901A1 (es) | 1967-04-01 |
| FI44605C (fi) | 1971-12-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NL8300193A (nl) | 5-methylthiopyrimidinederivaten, werkwijze voor het bereiden daarvan en fungicide preparaten, die genoemde derivaten als aktieve bestanddelen bevatten. | |
| US3326663A (en) | Herbicidal phenylureas | |
| EP0013581B1 (en) | Tetrahydrofuran derivatives, a process for their preparation, herbicidal compositions containing them and a method of controlling undesired plant growth using them | |
| US4149872A (en) | N-pyridinyl urea and cyclopropanecarboxamide herbicides | |
| NL8303808A (nl) | Gesubstitueerde heteroarylverbindingen als fungiciden. | |
| GB2173791A (en) | Fungicidal cyano oximes | |
| IL25486A (en) | Derivatives of 2,6-dichlorothiobenzamide,their preparation and use | |
| EP0008145B1 (en) | Use of phenyliminomethylpyridine derivatives as fungicides and plant growth regulants compositions containing such derivatives and phenyliminomethylpyridine derivatives and their preparation | |
| AU657022B2 (en) | Sulphonamide herbicides | |
| US3424723A (en) | 2,6-dihalobenzthiohydrazides | |
| EP0174046A2 (en) | Ether herbicides | |
| HU198168B (en) | Herbicides comprising diphenyl ether isoxazoline derivatives as active ingredient and process for producing the active ingredient | |
| US3418331A (en) | 2-(2,6-dihalophenyl)-4-hydroxy-thiazole-5-acetic acid and derivatives thereof | |
| US4441911A (en) | Herbicidal heterocyclic pentalenes | |
| CA1088089A (en) | Phenylalanine oxime esters | |
| US3296292A (en) | Esters and amides of 2, 3, 5, 6-tetrachloromonothioterephthalic acid | |
| EP0152131B1 (en) | Carboxamide derivatives, their preparation and their use as fungicides | |
| JPS5946923B2 (ja) | 除草剤 | |
| IL24261A (en) | Pesticides containing phenazine compounds and new phenazine compounds | |
| US4199346A (en) | Herbicides based on 2-dibenzofuranyloxyalkanecarboxylic acid derivatives | |
| US3790677A (en) | Control of phytopathogenic fungi with 3-arylimino-1,2-dithiols | |
| GB2096897A (en) | Fungicides | |
| CA1058207A (en) | Thioacylalanine derivatives | |
| US3119735A (en) | Method for combatting plant-parasitic nematodes | |
| CS208667B2 (en) | Herbicide means and method of making the active substances |