CN1043504C - Plant protection agent for control of fungi and bacteria - Google Patents
Plant protection agent for control of fungi and bacteria Download PDFInfo
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- CN1043504C CN1043504C CN91109999A CN91109999A CN1043504C CN 1043504 C CN1043504 C CN 1043504C CN 91109999 A CN91109999 A CN 91109999A CN 91109999 A CN91109999 A CN 91109999A CN 1043504 C CN1043504 C CN 1043504C
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- Prior art keywords
- rice
- compound
- trimethyl
- ammonium
- benzisothiazole
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Links
- 241000894006 Bacteria Species 0.000 title abstract description 13
- 241000233866 Fungi Species 0.000 title abstract description 11
- 239000011814 protection agent Substances 0.000 title abstract 2
- 201000010099 disease Diseases 0.000 claims abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 241000209094 Oryza Species 0.000 claims description 47
- 235000007164 Oryza sativa Nutrition 0.000 claims description 45
- 235000009566 rice Nutrition 0.000 claims description 45
- 239000002689 soil Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 11
- 241000196324 Embryophyta Species 0.000 claims description 7
- 230000001580 bacterial effect Effects 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 3
- 241000790917 Dioxys <bee> Species 0.000 claims 2
- 239000002352 surface water Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 44
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 abstract description 4
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000012360 testing method Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000003814 drug Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 230000002265 prevention Effects 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000004476 plant protection product Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000011081 inoculation Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 206010039509 Scab Diseases 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 230000000740 bleeding effect Effects 0.000 description 4
- 229940075419 choline hydroxide Drugs 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 230000002538 fungal effect Effects 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- -1 tertiary amine salt Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229960001231 choline Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000003203 everyday effect Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 235000019743 Choline chloride Nutrition 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241000218211 Maclura Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
- 229960003178 choline chloride Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- MQVMJSWYKLYFIG-UHFFFAOYSA-N propane-1-sulfonic acid;sodium Chemical compound [Na].CCCS(O)(=O)=O MQVMJSWYKLYFIG-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
1,2-benzoisothiazol-3(2H)-one, 1,1-dioxide, ion(1-),2-hydroxy-N,N,N-trimethyl-ethanaminium represented by the following formula (I): is found to have great utility as an effective component in plant protection agents for control of fungi and bacteria. By the use of the compound, diseases or blights of plants can be effectively prevented.
Description
The present invention relates to a kind of new compound, 1,2-benzisothiazole-3 (2H)-ketone-1,1-dioxy-N, N, the N-trimethyl-using method of 2-hydroxyl second ammonium when controlling plant diseases.
Known in the prior art 1,2-benzisothiazole-3 (2H)-ketone-1,1-titanium dioxide compound (calling " asccharin " in the following text) and its salt, for example alkali salt and ammonium salt are effective as plant protection product control fungi and bacterium.(can disclose 21496/1967 and 9428/1972 with reference to Japan Patent when needing, examine Japan Patent and disclose 5936/1973,22624/1973,109535/1974,105216/1977,11083/1977 and 72602/1987 and United States Patent (USP) 3280137).Also known in the prior art, the tertiary amine salt of asccharin and quaternary ammonium salt have control fungi and bacterium, as the use of plant protection product.(when needing, can with reference to the Japan Patent of not examining disclose 204707/1985 and Japan Patent disclose 34765/1980).
But these known bleeding agents also are not actually used in vegetable plague protection, and perhaps because underlying cause, some bleeding agent is very big or plant growth had bad effect to the toxicity of fish.The shortcoming of other bleeding agents is to render a service significantly to reduce when they being administered to the rice field of percolation water, perhaps renders a service with soil regime to change significantly.
Known another kind control fungi and bacterium and the plant protection product that has been widely used in agricultural are the 3-allyloxys-1 that contains as active principle; 2-benzisothiazole-1; 1-dioxide (annotation of translation: thiophene is bought by bacterium) (Meiji Seikakaisha Ltd; trade name " ORYZEMATE ", Japan Patent disclose 38080/1970 and United States Patent (USP) 3629428 in disclose).But protectant that this is known and asccharin relatively are expensive and its control fungi and bacterium active or render a service not always satisfactory.
An object of the present invention is to provide a kind of new and useful compound, it can use long-term and stably, and cover crop avoids eqpidemic disease, simultaneously crop is safe from harm.
Another object of the present invention provides a kind of improved plant protection product that contains the control fungi and the bacterium of this compound.
N, N, N one trimethyl-2-hydroxyl second ammonium (calling " choline " in the following text) is a kind of compound of Cobastab group, it is widely used as a kind of additive of feed stripped.In recent years, it is found that the similar compound of choline has a kind of function that promotes plant growth.
By choline and asccharin are combined, we have prepared a kind of new compound.This noval chemical compound is effective as a kind of fungicide and/or bactericide for various fungies that cause crop pest or eqpidemic disease and bacterium.Particularly when this compound administration is to the surface of soil of planting paddy rice or paddy field water either, for example compound with per 10 are 2 to 2000 grams, preferably 10 to 300 grams can effectively prevent the rice blast of growth paddy rice in the rice field and the leaf blight of leaf site when using.Therefore compound of the present invention can stably not kept rendeing a service in for a long time by the soil that blows off, and produces favourable effect, for example hestening rooting and the effect of tillering, and prevention is stretched over the eqpidemic disease that occurs on the leaf on top, ground and shows effect significantly.Based on aforesaid discovery, the present invention is accomplished.
Therefore, the invention provides a kind of new compound with following chemical formula (I)
1 of expression, 2-benzisothiazole-3 (2H)-ketone-1,1-dioxy N, N, N-trimethyl-2-hydroxyl second ammonium.
The present invention also provides preparation following chemical formula (I)
1 of expression, 2-benzisothiazole-3 (2H)-ketone-1,1-dioxy N, N, the method for N-trimethyl-2-hydroxyl second ammonium, this method comprises following chemical formula (II)
1 of expression, 2-benzisothiazole-3 (2H)-ketone-1,1-titanium dioxide compound and following chemical formula (III)
(X wherein
-Be OH
-Or acidic group) Biao Shi N, N, the derivatives reaction of N-trimethyl-2-hydroxyl second ammonium.
Also comprise the plant protection product of control fungi and bacterium within the scope of the invention, it is characterized in that containing following chemical formula (I)
1 of expression, 2-benzisothiazole-3 (2H)-ketone-1,1-dioxy N, N, N-trimethyl-2-hydroxyl second ammonium is an active principle.
The method that the present invention also provides a kind of cover crop to avoid disease is characterized in that using 1 of effective dose, 2-benzisothiazole-3 (2H)-ketone-1,1-dioxy N, N, N-trimethyl-2-hydroxyl second ammonium.
To be described in detail the present invention below.
The prepared in reaction that compound of the present invention can be represented by following chemical equation:
X wherein
-Be OH
-Or acidic group.
Each choline derivative of general formula (III) expression and the X-group that can be used as every kind of choline derivative of initiation material at The compounds of this invention can be OH
-Or acidic group.The example of acid is inorganic acid (as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid and a nitric acid); Carboxylic acid (as acetate, propionic acid, lactic acid and citric acid) and sulfonic acid (as methanesulfonic acid and benzene sulfonic acid).
Work as X
-Be OH
-The time, the asccharin of chemical formula (II) expression and initiation material (III) reaction can high-purity ground preparation compounds of the present invention.Work as X
-When being acidic group, need a kind of alkali neutralization.The example of spendable alkali comprises alkali-metal hydroxide (as sodium hydroxide and potassium hydroxide); Hydroxide of alkaline earth metal (as slaked lime and magnesium hydroxide) and alkali-metal carbonate (as sodium carbonate and sodium bicarbonate).From economic point of view and reactivity, best alkali is sodium hydroxide.In other words, asccharin and alkali in conjunction with the time can use the sodium salt of asccharin.Work as X
-Be acidic group and use in the alkali and the time, generate a kind of corresponding salt as accessory substance.Therefore, need when preparing compound of the present invention, a kind of high-purity stage preferably use X
-Be OH
-Initiation material.
This reaction needed is used solvent.The solvent that is suitable for comprises proton solvent (as water, methyl alcohol, ethanol and propyl alcohol); Ketones solvent (as acetone and methyl ethyl ketone) and aprotic solvent (as acetonitrile, N, dinethylformamide, methyl-sulfoxide and N-Methyl pyrrolidone.But preferably use proton solvent.Usually reaction is carried out substantially at ambient temperature.But but add the thermal reaction mixture accelerated reaction or can in the solvent that uses, dissolve initiation material.X when initiation material (III)
-Be OH
-The time, can finish reaction in the sub-short time at ambient temperature.By concentrating, steaming desolventizes, the product that vacuum drying concentrates.By top step, obtain a kind of The compounds of this invention that hygroscopic crystallization is arranged with stoichiometric productive rate basically.
Compound of the present invention can be directly as plant protection product control fungi and bacterium.Yet, can be dissolved or suspended in it in the appropriate liquid carrier in actual use usually, organic solvent for example, or compound is mixed with solid carrier or absorb with solid carrier, for example thinner or filler are suitable for this purposes.If desired, can add various assistant agents, for example emulsifier, stabilizing agent, dispersant, suspending agent, wetting agent and bleeding agent are to generate emulsion, wetting powder, granule or pulvis.Generally, per 10 ares of amounts of using The compounds of this invention are 2 to 2000 grams, preferably 10 to 300 grams.In order when using, to reduce the labour or to prevent various fungies and bacterial other eqpidemic disease, also can mix other bactericide or insecticide.When rice transplanting before the rice field, compound of the present invention when use in seedling basin or seedbed, behind the rice field, can prevent the rice blast and the leaf blight of appearance at rice transplanting with 2 to 2000 gram active principles for a long time in.After compound of the present invention is applied directly to the paddy soil or paddy field water either of having transplanted paddy rice, can be in long time the eqpidemic disease of prevention of water rice plant.
Now be with reference to the present invention is carried out specific description with embodiment.Yet be noted that the present invention is not limited only to the following examples.Synthesizing of embodiment 1 The compounds of this invention
1.48g (8.1 mM) asccharin is added in the 10ml methyl alcohol, under agitation this mixture is added about 49% the choline hydroxide aqueous solution (containing 0.98g (8.1 mM) choline hydroxide) of 2g.After the stirring at room 10 minutes, the asccharin of all addings dissolves, and reaction is promptly accused and finished.Concentrating under reduced pressure removes and desolvates, and vacuum drying subsequently obtains 2.36g (containing some moisture) light brown hygroscopicity crystalline compounds of the present invention.Dissolving crystallized in acetone, in this solution, add activated carbon, then filtering mixt.Hexane is added in the filtrate, is settled out a kind of grease.Remove solvent by decant, the dry in a vacuum oily mater that obtains, obtaining compound 1.71g of the present invention is white hygroscopicity crystal.Crystal is worn into powder, in a vacuum finish-drying.The fusing point of product is 77 to 79 ℃ (in tube sealing).
Infrared absorption spectroscopy JKBr, cm
-1
3370,1630,1580,1475,1455,
1333,1260,1150,950
Nuclear magnetic resoance spectrum (D
2O) 6:
(interior mark): (3-(trimethyl silicon based) propane sulfonic acid sodium)
3.19(9H,S),3.53(2H,m),
4.50(2H,m), 7.74(4H,S)
Results of elemental analyses:
C49.3％,H6.5％,N9.6％
C
12H
18N
2O
4S0.3H
2The O calculated value:
C49.4%, H6.4%, N9.6% embodiment 2 The compounds of this invention synthetic
1.48g (8.1 mM) asccharin is added in the 10ml water, under agitation, in this mixture, adds the choline hydroxide aqueous solution (containing 0.98g (8.1 mM) choline hydroxide) of 2g about 49%.After the stirring at room 20 minutes, the dissolving of the asccharin of all addings, reaction are promptly accused and are finished.Under reduced pressure concentrate this reactant mixture, concentrated product is dissolved in the 30ml acetone.Activated carbon is added in this solution, filters this mixture then.Under agitation, hexane is added in the filtrate at leisure.When becoming muddiness a little, solution adds crystal seed, thus isolation of crystalline.Slowly add hexane again with complete isolation of crystalline.On glass filter, collect crystal and dry rapidly in a vacuum, obtain 1.07g white hygroscopicity crystal.Crystal is dissolved in the acetone again, under agitation drips hexane, obtain crystal.Collect crystal and dry in a vacuum, obtain the compound of the present invention (putting tube sealing) of 78 to 79 ℃ of fusing points.
Results of elemental analyses:
C49.5％,H6.6％,N9.6％
C
12H
18N
2O
4S0.3H
2The O calculated value:
C49.4%, H6.4%, N9.6% embodiment 3 The compounds of this invention synthetic:
The asccharin sodium salt of 2.05g (10 mM) is added in the 10ml methyl alcohol, in this solution, adds 1.40g (10 mM) choline chloride.Seethe with excitement after one hour, under reduced pressure reclaim most of methyl alcohol.Be added to the 15ml carrene in the residue and stir this mixture fully effectively.Leach insoluble sodium chloride, under reduced pressure concentrated filtrate removes and desolvates, and is dry in a vacuum subsequently, obtains the compound of the present invention of white hygroscopic lenticular.Output 2.80g.
The product pulverize is also fully dry in vacuum.The product fusing point is 76 to 78 ℃ (tube sealing).The preparation of embodiment 4 wetting powders:
30 parts of (" part " expression " weight portion ") compounds of the present invention are mixed with 2 parts of white carbon, and then mix with 3 parts of alkyl ether sodium sulfonates and 2 parts of Negels again as wetting agent.This mixture and then mix with 63 parts of clays again as filler.With this mixture mixed grinding, make wetting powder.The preparation of embodiment 5 granules
8 parts of compounds of the present invention are mixed with 62 parts of clays and 26 parts of bentonites, mix with 0.5 part of alkylbenzenesulfonate and 3.5 parts of sodium lignosulfonates, back two compounds are as disintegrant.The water that adds Sq constantly mixes in mixture simultaneously.With the mixture granulating that obtains, drying is sieved particle subsequently, makes granule.The test of embodiment 6 soil application effect evaluations
In the synthetic resin basin of each diameter 6.5cm, plant rice plants (kind: KOSHIHIKARI) until growing to for 3 leaf stages.Each experiment sub-district comprises 4 basins, plants 40 strain paddy rice.Use the dilution preparation that 10ml is diluted with water to the wetting powder preparation of giving the embodiment 4 that decides concentration at the soil surface of each basin.Used behind the medicament 14 days, and rice blast fungal spore suspension evenly was sprayed on the rice plants inoculates.Keep 25 ℃ of one night in wet chamber after, but basin moves on to the indoor of manual control environment.Inoculation rice fungal spore calculated disease lesion number after 7 days, calculated the prevention value by following formula:
The results are shown in table 1.
Table 1
Embodiment 7 uses the effectiveness of test and comments rank under water oozes out condition
| Test medicine | Active principle amount (g/10 are) | Prevention value (%) | Chemical damage to paddy rice |
| The compound of the present invention compound of the present invention compound allyl isothiazole of the present invention asccharin sodium salt district of being untreated | 100 60 15 100 100 - | 95 88 83 78 84 0 | To a certain degree infringement before not growing up to, nothing is arranged |
With 3 leaf phase paddy rice (kinds: KOS-HIHIKARI) migrate to 100cm
2Basin in test.The test region of each test comprises 5 basins, plants 30 strain paddy rice.Every basin is filled with water with the about 3cm of the degree of depth that causes water.The surface that a kind of thinner of the wetting powder of the embodiment 4 of dilute with water preparation is placed on water makes that the amount of medicament transfers to the value that shows in the following table 2 in the basin.Make the seepage in every basin, make water depth minimizing every day 1cm, during the whole test, replenish a water every day.Paddy growth 28 days is sprayed on the plant in the 29th day suspension with the rice blast fungal spore and inoculates.After the inoculation, immediately basin is moved on to wet chamber and kept 24 hours.After 24 hours, basin is moved on to the greenhouse.Behind the inoculating spores 7 days, calculate the scab number that on paddy rice, occurs.Similar example 6 calculates the prevention value.Simultaneously, check tiller number, calculate the tiller number in each treatment region, found ratio at the tiller number of the district's discovery of being untreated of not using medicament with a kind of medicament.
Table 2
Embodiment 8 seedling growing box rice test effect evaluations
| Test medicine | Use the amount (g/10 are) of active principle | Prevention value (%) | The ratio of tiller number (%) |
| Compound of the present invention compound allyl isothiazole of the present invention allyl isothiazole asccharin sodium salt saccharin sodium salt is untreated and distinguishes the district of being untreated | 60 15 60 15 60 15 - - | 92 76 51 48 27 10 0 0 | 115 103 102 98 76 89 100 100 |
(kind: KOSHIHIKARI) plantation is on the thin seedling case of a 20cm * 30cm, until growing to 3 leaf phases paddy rice.Drug concentration is transferred to predetermined concentration, is administered to the seedling case soil surface of plantation paddy rice.After 8 days paddy rice is extracted from the seedling case, cleaned the rice root, then they are transplanted to the 100cm that does not use any medicament
2In the soil of basin.Each test region comprises 4 basins of kind of 24 strain paddy rice.Transplant after 17 days, the suspension spray of rice blast fungal spore is inoculated to paddy rice.The inoculation back is placed on wet chamber to them stablized 24 hours, moved on to the greenhouse then.Inoculation was checked the number that occurs scab on the leaf after 7 days, and calculated the prevention value of every kind of medicament by the method for similar embodiment 6.
Test the results are shown in table 3.
Table 3
The sick test of embodiment 9 paddy rice leaf three-bristle cudranias effect evaluation
| Test medicine | Use the amount (g/10 are) of active principle | Prevention value (%) | The chemical damage of paddy rice |
| The sodium salt of the sodium salt asccharin of the sodium salt asccharin of compound of the present invention compound of the present invention compound asccharin of the present invention | 1000 100 10 1000 100 10 | 97 94 90 97 86 65 | Nothing is tillered, and the difference tiller is poor slightly slightly for the difference tiller |
Paddy rice (kind: KINNANPU) plantation 1 first quarter moon in 1/5000 are basin.8% granular preparation as preparation among the embodiment 5 of scheduled volume is applied in the water surface of basin.Use after 5 days, on the paddy rice leaf, inoculate leaf spot bacteria with pin.Behind the inoculation leaf spot bacteria the 21st day, measure the length of each scab on the paddy rice leaf.
Result of the test is shown in table 4
Table 4
| Test medicine | Active principle amount (g/10 are) | Scab average length (cm) | Chemical damage to paddy rice |
| The compound of the present invention compound of the present invention district of being untreated | 500 240 - | 1.2 1.2 10.1 | Do not have |
Chemical combination of the present invention prevention rice blast and bacterial leaf-blight are effectively, and they can hazard rice in for a long time, and bacterial leaf-blight and rice blast are serious problems in paddy growth.No matter be compound of the present invention to be applied to (comprise and be applied to water surface) and still be applied to seedling basin or seedbed that it all presents significant effectiveness in the paddy soil.Compound of the present invention only has mild toxicity to fish, thereby has a great deal of practical meanings.
Claims (4)
1. use effective dose by chemical formula (I) expression
1,2-benzisothiazole-3 (2H) ketone 1, the second ammonium is in plant corpus for 1-dioxy (N, N, N-trimethyl 2-hydroxyl), and cover crop avoids eqpidemic disease.
To wet rice cultivation soil or anthropogenic soil surface waterborne impose per 10 are 2 to 1 of 2000 grams, 2-benzisothiazole-3 (2H) ketone 1,1, dioxy (N, N, N-trimethyl-2-hydroxyl) second ammonium, the protection paddy rice avoids rice blast.
3. transplanting paddy rice to the rice field,, use 2 to 2000 gram 1,2 benzisothiazole-3 (2H)-ketone-1 for per 10 ares for the soil in seedling basin or seedbed, 1-dioxy (N, N, N-trimethyl-2-hydroxyl) second ammonium, the protection paddy rice avoids rice blast.
4. to the surface water of wet rice cultivation soil or anthropogenic soil, use 1 of 2 to 2000 grams for per 10 ares, 2-benzisothiazole-3 (2H)-ketone-1,1 dioxy (N, N, N-trimethyl-2-hydroxyl) second ammonium, the protection paddy rice avoids bacterial leaf-blight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN91109999A CN1043504C (en) | 1987-11-18 | 1991-10-28 | Plant protection agent for control of fungi and bacteria |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP290833/87 | 1987-11-18 | ||
| JP62290833A JPH01132571A (en) | 1987-11-18 | 1987-11-18 | Agricultural and horticultural fungicide |
| CN88104596A CN1019298B (en) | 1987-11-18 | 1988-07-26 | Plant protection agent for control of fungi and bacteria |
| CN91109999A CN1043504C (en) | 1987-11-18 | 1991-10-28 | Plant protection agent for control of fungi and bacteria |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN88104596A Division CN1019298B (en) | 1987-11-18 | 1988-07-26 | Plant protection agent for control of fungi and bacteria |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1060384A CN1060384A (en) | 1992-04-22 |
| CN1043504C true CN1043504C (en) | 1999-06-02 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN91109999A Expired - Fee Related CN1043504C (en) | 1987-11-18 | 1991-10-28 | Plant protection agent for control of fungi and bacteria |
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| Country | Link |
|---|---|
| CN (1) | CN1043504C (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106804158A (en) * | 2016-12-09 | 2017-06-09 | 河池市农业科学研究所 | A kind of rice blast prevention and controls |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3392115A (en) * | 1961-07-11 | 1968-07-09 | Hollichem Corp | High-viscosity quaternary ammonium benzosulfimides |
| JPS49117627A (en) * | 1973-03-15 | 1974-11-11 | ||
| US3970755A (en) * | 1973-05-10 | 1976-07-20 | Imperial Chemical Industries Limited | Biocidal compositions |
-
1991
- 1991-10-28 CN CN91109999A patent/CN1043504C/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3392115A (en) * | 1961-07-11 | 1968-07-09 | Hollichem Corp | High-viscosity quaternary ammonium benzosulfimides |
| JPS49117627A (en) * | 1973-03-15 | 1974-11-11 | ||
| US3970755A (en) * | 1973-05-10 | 1976-07-20 | Imperial Chemical Industries Limited | Biocidal compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1060384A (en) | 1992-04-22 |
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