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)
Description
'JHUJI }713 ΤϊΙΠΓ'Ί m PATENT ATTORNEYS · O ' D I D S ' 3111) PATENTS AND DESIGNS ORDINANCE SPECIFICATION Novel derivatives of 2,6-dic lorothiobenaaa.ide, their preparation and use I (we) SHELL IKTEHHATIONALE RISEAKCH MAATSCHAPPIJ N.V., of , Carel van Bylandtlaan, The Hague, a Netherlands Company do hereby declare the nature of this invention and in what manner the same is to "be performed, to he particularly described and ascertained in and by the following statement: - This invention relates to novel herbicidal derivatives of 2,6-dichlorothiobenzamide, methods for their preparation, herbicidal compositions containing them, and to a method for combating weeds.
The novel derivatives of 2, 6-dichlorothiobenzamide ac-cording to the invention have the general formula: - wherein R represents an alkyl or haloalkyl group, said group preferably containing 1-6 carbon atoms, and X represents an alkyl, aryl or alkaryl sulphate or sulphonate ion. Examples of the sul-phonate ion are the methanesulphonate, ethanesulphonate, benzene-sulphonate and toluenesulphonate, for example the p-toluenesulphonate ion. Examples of the sulphate ion are the methyl sulphate, ethyl sulphate, isopropyl sulphate and nonyl sulphate ion.
The haloalkyl group which R may represent is preferably a chloro or bromoalkyl group, for example a 2-chloroethyl, 3-bromopropyl or 2-chlo obutyl group.
The compounds of the invention are active pre-emergence herbicides. The methyl sulphate salt of S-methyl-2, 6-dichloro-thiobenzimidate combines a high herbicidal activity with a low mammalian toxicity. Accordingly, it is the preferred compound of the invention.
The compounds of the invention may be used in the manner known for herbicides, that is to say, they may be applied in admixture with an inert diluent which may contain a surface-active agent. The invention also includes therefore a herbicidal composition which comprises a compound of the invention and a carrier, or a surface -active agent, or both a carrier and a surface-active agent .
The carrier may be a solid, a liquid or a compressed gas. Examples of suitable solid carriers are clays, silicates, synthetic hydrated silicon oxides, resins, waxes, synthetic polymeric materials, carbon and sulphur. Examples of suitable liquid carriers are water, alcohols, ketones, aromatic hydrocarbons, chlorinated hydro of suitable compressed gases are those normally employed in aerosols, for example trichloromonofluoromethane or dichlorodifluoromethane.
The surface-active agent may be anionic, cationic or nonionic and may take the form of an emulsifier, wetting agent, dispersing agent or a sticker. Examples of suitable surface-active agents are alkyl aryl sulphonates alkyl sulphates containing more than 10 carbon atoms, alkylphenol/ethylene oxide condensates, sor-bitan esters of fatty acids, alkylamide sulphonates and ethylene oxide/fatty acid ester condensates.
The compositions of the invention may be formulated as a wettable powder, a dust, granules, a concentrate, a solution, an emulsifiable concentrate, a conventional emulsion, an invert emulsion, an aerosol, or an encapsulated material.
The novel compounds of the invention may also be used in combination with each other or with other substances, for example, known pesticides and/or fertilizers.
The invention also contemplates a method of combating weeds which comprises applying to said weeds and/or their habitat a compound of the invention or a herbicidal composition containing it.
The novel compounds of the invention may be prepared by techniques known to the chemical art. They may be prepared, for example, by reacting 2, 6-dichlorothiobenzamide with the appropriate ester cf an oxy-sulphur acid. According to the invention, the novel compounds having the general formula:- may be prepared by reacting 2, 6-dichlorothiobenzamide with a compound of the formula HX wherein R and X have the meanings hereinbefore specified. Thus when, for example, dimethyl sulphate is reacted with 2, 6-dichlorothiobenzamide, the following compound is obtained:- The reaction may be carried out in the absence of a reaction medium but is preferably carried out in the presence of an inert reaction medium which may be organic or inorganic, for example acetone or water. In some cases better yields are obtained when the reaction is carried out at elevated temperature, suitably in the range 6θ°- 100°C for example at the reflux temperature of the reaction mixture.
All aspects of the invention are further illustrated in the Examples that follow in which parts by weight (w) and parts by volume (v) bear the same relation as the kilogram to the litre.
EXAMPLE I Preparation of S-methyl-2,6-dichlorothio- benzimidate methyl sulphate CI © Θ CH S0 SCH.
CI (i) Without a reaction medium 2, 6-Dichlorothiobenzamide ( 20.6 w) and dimethyl sulphate ( 1 2.6 w) were heated together at 100°C for three hours and then left at room temperature for sixteen hours. The mixture was ground up with acetone ( 50 v) and filtered. The desired product ( 28 w), .p. 1 88°- 1 89°C, was obtained in 85$ yield. ( ii ) With water as reaction medium 2, 6-Dichlorothiobenzamide ( 20.6 w), dimethyl sulphate ( 1 .6 w) and distilled water (80 w) were stirred at 80°-90°C until a solution was formed. The hot solution was filtered and the filtrate was allowed to cool. The resulting solid was filtered off, washed with acetone ( 50 v) and dried. The desired product ( l 8.5 w), m.p. l 89°- 190°C, was obtained in 6 yield. (iii) With acetone as reaction medium and acetone ( 150 v) were mixed together and refluxed for one hour. A white solid was obtained which was filtered, washed firstly with acetone and then with ether. The desired product ( 28 w), m.p. 189°- 190°C was obtained in 85$ yield.
Analysis Found : C 32.2; H 3.4; N 4.5; S 19 -0; CI 2^.^ C.Hl1Cl N0.,S requires: C 32.5 H 3-3; N 4. 2; S 19-3; CI 21 . # 9 1 I . 4 EXAMPLE II Preparation of S-ethyl-2, 6-dichlorothiobenzitnidate ethyl sulphate 2, 6-Dichlorothiobenzamide (20 w), diethyl sulphate (20 w) and acetone (100 v) were mixed together and refluxed for 12 hours. The acetone was evaporated from the reaction mixture and the residue was crystallized from ethyl acetate affording the desired product, m.p. 149°-1 51°C.
Analysis Pound : C 36. H . ; N .9; S 17-8; CI 19· 5# EXAMPLE III Preparation of S-ethyl-2, 6-dichlorothiobenzimidate methanesulphonate 2, 6-Dichlorothiobenzamide ( 21 w) and ethyl methanesulphonate ( 1 2.5 w) were heated together on a water bath for three hours. The mixture was cooled, acetone added, and a white solid crystallized on standing. The solid (22 w) was filtered and washed with acetone and then with ether. Yield 66%, m.p. 176°-178°C.
Analysis Found : C .4 H 4.0; S 19.2; CI 21 .5# C H N0 S C1 requires: C 36.4; H 3-9; S 19.4; CI 21 .556 In the same way the following compounds were prepared:- m.p. 166°-168°C (68j6) Pound : C 47-1; H 4.4; 3-4; S 15-7; CI 17-7$ C16H17N0^S2C12 requires: C 47-3; H 4.2; N 3-4; S 15-8; CI 17-5$ 1¾°-134°C (6 £) Pound : C 49-5 H 4.9; S l4.3; CI ΐ6.¾ί EXAMPLE IV Preparation of S-n-butyl-2, 6-dichlorothiobenzimidate methanesulphonate 2., 6-Dichlorothiobenzamide (20.6 w) and butyl methanesulphonate (15-2 w) were heated together at 100°C for 2 hours. The mixture was dissolved in acetone (50 v) and allowed to crystallize overnight. The white crystals were filtered and washed giving the product (15 w) m.p. 110O-112°C. A further quantity (8 w) of material was obtained by pouring the filtrate into ether (100 v). Total yield 64$.
Analysis Found : C 40 H 4-5; N 3-9 S 17-9; CI 20.0$ requires: C 40.2; H 4.7; N 5-9 S 17-9; CI 19.8# In the same way the following compound was prepared:- m.p. 141°-143°C Found : C 48.4; H 4.4; N 3-2; S 15-2 C17HigCl2Nt3S2 requires: C 48.6; H 4.5; N 3-3; S 15-2$ EXAMPLE V Preparation of S-methyl- 2, 6-diehlorothio- benzimidate ethane sulphonate 2, 6-Dichlorothiobenzamide (21 w), methyl ethanesulphonate (12.5 w) and acetone (150 v) were refluxed together for 20 hours. The reaction mixture was then cooled and a white solid crystallized from the mixture. It was filtered and the residue washed with acetone and then ether. Yield 17 w, m.p. 174 -176 C.
Analysis Found : C 36.4; H 4.0; N 4.2; S 19-2; CI 21.7 C1£)H.^C12N0^S2 requires: C 36.4; H 3-9; N 4.2; S 19-4; CI 21.
In the same way the following compound was prepared :- m.p. 178°-l80°C Found : C 44-3; H 3-4; N 3-7; S 17-2; CI 19-0$ requires: C 44.4; H 3-4; N 3-7; S 16·9; CI 18.85G EXAMPLE VI Preparation of S-n-propyl-2, 6-dichlorothio- benzimidate p-toluenesulphonate 2, 6-Dichlorothiobenzamide ( 21 w) and n-propyl p_-toluene-sulphonate (22 w) were heated together on a water bath for 2 hours. The reaction mixture was cooled and washed with ether yielding a sticky solid. A small amount of acetone was added and a white solid separated out; this was filtered and then washed with acetone. Yield 1 5 w, m.p. 1410- 143°C.
Analysis Pound : C 48.7 H 4.7; S 14.9; CI l6.9?6 Cl7H19Cl2N0 32 requires: C 48.6; H 4.5; S 1 5- 2; CI l6.9# In the same way the following compound was prepared:- m.p. 1 29°- 131°C Found : C 45. 2; H 4.2; S 1 4.2; CI 2J>.J> C17H18C12N05S2 requires: C 44- 9; H 3,9; S 14. 1 ; CI 2J. % EXAMPLE VII Preparation of S-methyl-2, 6-dichlorothio benzimidate p-toluenesulphonate 2, 6-Dichlorothiobenzamide (20 w), methyl p-toluenesulphonate ( 18 w) and acetone (100 v) were refluxed together for 6 hours. The reaction mixture was left at room temperature for 16 solution. Yield 12 w.
Analysis Found : C 5.6; H 3-7; S 16.6; CI l8.0# C1t-H.cCl_N0-.S requires: C 5.9; H 3-8; S 16.3; CI 18.1$ EXAMPLE VIII Preparation of S-(2-chloroethyl)-2,6- dichlorothiobenzimidate p-toluenesulphonate 2, 6-Dichlorothiobenzamide (21 w) and 2-chloroethyl p-toluenesulphonate ( · 5 ) were heated on a water bath for 6 hours. The reaction mixture was cooled and ether was added; a small amount of solid precipitated which was filtered off. The filtrate was allowed to stand overnight; pale yellow crystals were obtained. They were filtered, combined with the first portion, and washed with acetone. Yield 6 w, m.p. 1 4°-156°C.
Analysis Found : C 3-8 H -9 CI 24.5$ requires: C 43-6; H 3-6; CI 24.2$ EXAMPLE IX Preparation of an Emulsifiable Concentrate An emulsifiable concentrate was prepared by mixing the following ingredients :- S-methyl-2, 6-dichlorothiobenz- imidate methyl sulphate (Example I) 20.2$ w/v Surface-active agent (Tensiofix D 120) 5-0$ w/v Carrier (N-methyl pyrrollidone) to 100 v (Tensiofix D 1 0 is a commercially available surface-active agent and comprises an alkyl aryl polyether alcohol).
EXAMPLE X Preparation of a Wettable Powder A wettable powder was prepared by mixing the following ingredients :- S-methyl-2, 6-dichlorothiobenz- imidate methyl sulphate 0. w/w Carrier (Clay GTY) 39 - 5$ w/w (Nonipol CS 50 s a water-soluble, non-ionic surface-active agent and comprises a polyethylene glycol ether; Aerosol OT/B is a surface-active and wetting agent and comprises sodium dioctyl sulpho succinate; Clay GTY is a kaolinite china clay).
EXAMPLE XI Herbicidal Activity The compounds of the invention are essentially pre-emergence herbicides and their degree of activity was determined by the following method.
Seeds of Oat ( 0) , ryegrass (RCJ), sweet corn (SC), pea (P), sugar beet (SB), linseed (L) and mustard (M) were sown arid allowed to germinate in sterile John Innes compost. The soil was sprayed at a volume equivalent to 50 gallons per acre with the following compositions : - Acetone 0# by volume Water 60$ by volume Surface-active agent (Triton X- 1 55) 0· 5¾ by weight Active ingredient varying amounts (Triton X- 1 55 is a commercially available surface-active agent and comprises an alkyl aryl polyether alcohol). Control tests were also carried out.
After 1 2 days the phytotoxic effect of the compound applied was assessed by determining the reduction in fresh weight of stem and leaf of the emerging plants over the control plants and plotting a regression curve relating the growth inhibition (CI) and the dosage of compound applied. The dosage required for 90 growth inhibition (i.e. that weight of compound required to give a reduction in the fresh weight of plants leaf and stem of 90$) is given in the following Table in pounds per acre.
TABLE TABLE (cont'd)
Claims (26)
1. ΗΑ'νΙΚΠ- ΟΎ particularly described and ascertained nature of our said invention and in what manner the s^me in be performed, we declare that ¾rhat we claiw is Compounds having the general formula:- CI CI wherein R represents an alkyl or haloalkyl group and X represents an alkyl, aryl or alkaryl sulphate or sulphonate ion.
2. Compounds as claimed in claim \, wherein R represents an alkyl or haloalkyl group containing 1-6 carbon atoms.
3. · Compounds as claimed in claim 1 or 2, wherein R represents a chloro- or bromo-alkyl group.
4. S-methyl-2, 6-dichlorothiobenzimidate methyl sulphate.
5. · S-methyl-2, 6-dichlorothiobenzimidate ethanesulphonate.
6. S-methyl-2, 6-dichlorothiobenzimidate benzenesulphonate.
7. - S-methyl-2, 6-dichlorothiobenzimidate p-toluenesulphonate.
8. S-ethyl-2, 6-dichlorothiobenzimidate methanesulphonate .
9. · S-ethyl-2, 6-dichlorothiobenzimidate ethyl sulphate.
10. S-ethyl-2, 6-dichlorothiobenzimidate p-toluenesulphonate.
11. S-(2-chloroethyl)-2, 6-dichlorothiobenzimidate p-toluenesulphonate.
12. S-(n-propyl)-2, 6-dichlorothiobenzimidate p-toluenesulphonate.
13. · S- (3-chloropropyl)-2, 6-dichlorothiobenzimidate p-toluenesulphonate.
14. 1 . S-(n-butyl) -2, 6-dichlorothiobenzimidate methanesulphonate.
15. S-(n-butyl) -2, 6-dichlorothiobenzimidate benzenesulphonate.
16. S-(n-butyl) -2, 6-dichlorothiobenzimidate p-toluenesulphonate.
17. any one of claims 1 - 16, wherein 2, 6-dichlorothiobenzamide is reacted with a compound of the formula RX wherein R represents an alkyl or haloalkyl group and X represents an alkyl, aryl or alkaryl sulphate or sulphonate ion*
18. A process as claimed in claim 17, wherein the reaction is carried out in an inert reaction medium.
19. · A process as claimed in claim 18, wherein the inert reaction medium is acetone or water.
20. A process as claimed in claim 17* 18 or 19* wherein the reaction is carried out at an elevated temperature.
21. A process or the preparation of compounds specif ed in any one of claims 1 - 16, substantially as hereinbefore described
22. A process for the preparation of compounds specified in any one of claims 1 -16, substantially as hereinbefore described with reference to any of Examples I-VIII.
23. 3- A herbicidal composition comprising a compound as specified in any one of claims 1 -16, a carrier, a surface-active agent, or both a carrier and a surf ce-active agent.
24. A composition as claimed in claim 23, formulated as a wettable powder, a dust, granules, a concentrate, a solution, an emulsifiable concentrate, a conventional emulsion, an invert emulsion, or an encapsulated material.
25. · A composition as claimed in claim 23, substantially as hereinbefore described.
26. A composition as claimed in any one of claims 23-2 * substantially as hereinbefore described in Examples IX and X. 27· A method of combating weeds which comprises applying to said weeds and/or their habitat a compound as claimed in any one of claims 1 -16 or a composition as claimed in any one of claims 23-26. Dated this 29th day of ¾rch, 1966 R11
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 |
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IL25486A true IL25486A (en) | 1969-07-30 |
Family
ID=10030383
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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IL25486A IL25486A (en) | 1965-04-01 | 1966-03-30 | Derivatives of 2,6-dichlorothiobenzamide,their preparation and use |
Country Status (10)
Country | Link |
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BE (1) | BE678687A (en) |
CH (1) | CH489997A (en) |
DE (1) | DE1567130A1 (en) |
DK (1) | DK120128B (en) |
ES (1) | ES324901A1 (en) |
FI (1) | FI44605C (en) |
GB (1) | GB1039459A (en) |
IL (1) | IL25486A (en) |
NL (1) | NL6604251A (en) |
SE (1) | SE325873B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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US4131449A (en) * | 1977-10-17 | 1978-12-26 | Shell Oil Company | Propanimidothioic acid derivatives |
CN100357290C (en) * | 1997-04-24 | 2007-12-26 | 道农业科学公司 | Pesticidal 3-(substituted phenyl)-5-(thienyl or furyl)-1,2,4-triazoles |
HU228839B1 (en) * | 1998-10-23 | 2013-06-28 | 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 DK DK166066AA patent/DK120128B/en unknown
- 1966-03-30 ES ES0324901A patent/ES324901A1/en not_active Expired
- 1966-03-30 DE DE19661567130 patent/DE1567130A1/en active Pending
- 1966-03-30 FI FI660815A patent/FI44605C/en active
- 1966-03-30 IL IL25486A patent/IL25486A/en unknown
- 1966-03-30 BE BE678687D patent/BE678687A/xx unknown
- 1966-03-30 CH CH461066A patent/CH489997A/en not_active IP Right Cessation
- 1966-03-31 NL NL6604251A patent/NL6604251A/xx unknown
Also Published As
Publication number | Publication date |
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DK120128B (en) | 1971-04-13 |
NL6604251A (en) | 1966-10-03 |
DE1567130A1 (en) | 1970-07-23 |
CH489997A (en) | 1970-05-15 |
BE678687A (en) | 1966-09-30 |
FI44605B (en) | 1971-08-31 |
FI44605C (en) | 1971-12-10 |
SE325873B (en) | 1970-07-13 |
ES324901A1 (en) | 1967-04-01 |
GB1039459A (en) | 1966-08-17 |
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