CN1151738A - 烷基亚磺酰基与烷基磺酰基-1，2，4-噻二唑基氧乙酰胺及其作为除莠剂的应用 - Google Patents
烷基亚磺酰基与烷基磺酰基-1，2，4-噻二唑基氧乙酰胺及其作为除莠剂的应用 Download PDFInfo
- Publication number
- CN1151738A CN1151738A CN95193810A CN95193810A CN1151738A CN 1151738 A CN1151738 A CN 1151738A CN 95193810 A CN95193810 A CN 95193810A CN 95193810 A CN95193810 A CN 95193810A CN 1151738 A CN1151738 A CN 1151738A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- methyl
- thiadiazoles
- base
- oxygen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 alkyl sulphonyl-1,2,4-thiadiazolyloxy acetamides Chemical class 0.000 title claims abstract description 50
- 125000004644 alkyl sulfinyl group Chemical group 0.000 title claims abstract description 10
- 239000004009 herbicide Substances 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 32
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000005605 benzo group Chemical group 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 42
- 239000001301 oxygen Substances 0.000 claims description 35
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- 239000013543 active substance Substances 0.000 claims description 32
- 241000196324 Embryophyta Species 0.000 claims description 29
- 239000000460 chlorine Substances 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 239000011737 fluorine Substances 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 229960001413 acetanilide Drugs 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 claims description 5
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 claims description 5
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 4
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 230000002363 herbicidal effect Effects 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 125000006170 pentacyclic group Chemical group 0.000 claims description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 2
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000005981 pentynyl group Chemical group 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 claims 5
- OJHNOEXAECSREP-UHFFFAOYSA-N 5-chloro-3-methylsulfonyl-1,2,4-thiadiazole Chemical class CS(=O)(=O)C1=NSC(Cl)=N1 OJHNOEXAECSREP-UHFFFAOYSA-N 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000006193 alkinyl group Chemical group 0.000 abstract 2
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 244000025254 Cannabis sativa Species 0.000 description 31
- 235000021331 green beans Nutrition 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 244000013123 dwarf bean Species 0.000 description 15
- 229920000742 Cotton Polymers 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 240000007087 Apium graveolens Species 0.000 description 12
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 12
- 235000010591 Appio Nutrition 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000002994 raw material Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000005660 chlorination reaction Methods 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 240000008866 Ziziphus nummularia Species 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229940023569 palmate Drugs 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
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- 150000003839 salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
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- 150000003568 thioethers Chemical class 0.000 description 1
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- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
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- 229920002554 vinyl polymer Polymers 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及式(1)表示的新型烷基亚磺酰基与烷基磺酰基-1，2，4-噻二唑基氧乙酰胺。式中的n为1或2，R1为氢或烷基、烯基、炔基或芳烷基可取代或未取代，R2为烷基、烯基、炔基、环烷基、环烯基、芳烷基、芳基、烷氧基、烯氧基或炔氧基可取代或未取代，或R1及R2与氮原子一起结合形成取代或未取代的饱和的或不和的氮杂环、它还可含别的杂原子和与苯并基稠合，R3烷基、芳基或芳烷基可取代或未取代(其中某些现有技术的个别化合物不包括在内)，其制法及制备新化合物的新的中间体以及其在除莠剂方面的应用。
Description
本发明涉及新型烷基亚磺酰基与烷基磺酰基-1，2，4-噻二唑基氧乙酰胺，其制造方法及所使用的新的中间体以及它们在除莠剂方面的应用。
某些烷基亚磺酰基与烷基磺酰基-1，2，4-噻二唑基氧乙酰胺，如N-异丙基-α-(3-甲基亚磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰苯胺已知其具有除莠剂的性能(参阅如EP-A 348737及在先但未公开的德国母专利申请4317323的说明，1993年5月25申请)。这种已公开发表的化合物的活性作用在各方面的使用中都不完全令人满意，特别是在剂量小及浓度低时更是这样。
现已发现了一种可用通式(I)表示的新型烷基亚磺酰基与烷基磺酰基-1，2，4-噻二唑基氧乙酰胺式中
n为1或2，
R1为氢或为烷基，烯基，炔基或芳烷基，它们可以是取代或未取代的，
R2为烷基，烯基，炔基，环烷基，环烯基，芳烷基，芳基，烷氧基，烯氧基，炔氧基，它们可以是取代或未取代的，或
R1及R2与氮原子一起结合成取代或未取代的，饱和的或不饱和的氮杂环，它还可含其他杂原子和与苯并基稠合，
R3为烷基，芳基或芳烷基，它们可以是取代或未取代的。
必须指出，下列化合物由于已提出过(参见EP-A-348737和1993年5月25日提交的德国专利申请4317323说明书)而不包括在本发明上述通式化合物之内： N-异丙基-α-(3-甲基亚磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰苯胺，N-异丙基-α-(3-甲基磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰苯胺，N-异丙基-α-(3-乙基亚磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰苯胺，N-异丙基-α-(3-乙基磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰苯胺，N-异丙基-α-(3-丙基亚磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰苯胺，N-异丙基-α-(3-丙基磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰苯胺，(参阅EP-A348737)以及化合物N-甲基-N-(4-氟-苯基)-α-(3-甲基亚磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰胺，N-甲基-N-(4-氟-苯基)-α-(3-甲基磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰胺，N-甲基-N-(4-氟-苯基)-α-(3-乙基磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰胺，N-乙基-N-(4-氟-苯基)-α-(3-甲基亚磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰胺，N-乙基-N-(4-氟-苯基)-α-(3-甲基磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰胺及N-乙基-N-(4-氟-苯基)-α-(3-乙基磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰胺，(参阅德国专利说明书4317323，1993年5月25日)。
另外，还发现采用下列方法(a)及(b)可以获得这种通式(I)表示的新型烷基亚磺酰基与烷基磺酰基-1，2，4-噻二唑基氧乙酰胺。
(a)用通式(II)表示的1，2，4-噻二唑衍生物为原料
式中
X为卤素或原子团-S(O)n-R3，和其中的n及R3的含义如前述，与通式(III)表示的羟基乙酰胺反应；
式中R1及R2的含义如前述，并如需要可在稀释剂及酸结合剂以及催化剂存在下反应；
(b)用通式(IV)表示的烷基(芳基-，芳烷基-)硫-1，2，4-噻二唑基氧乙酰胺
式中R1、R2、R3的含义如前述，与氧化剂，如需要可加入催化剂及稀释剂进行反应。
最后还发现这些通式(I)表示的新型烷基亚磺酰基与烷基磺酰基-1，2，4-噻二唑基氧乙酰胺具有不平常的消灭杂草的性质。
令人惊异的是所发明的式(I)表示的新化合物一方面与农作物例如棉花能很好适应相安无事，而对某些较难对付的杂草则非常有效，与化学成份很接近的已知化合物如N-异丙基-α-(3-甲基亚磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰苯胺对比效果好得多。
本发明的优选的式(I)表示的化合物，是式中
n为1或2
R1为氢或C1-C8-烷基(可以任选地被氟、氯、氰或C1-C4-烷氧基取代)，C2-C8-烯基(可任选地被氟和/或氯取代)，C2-C8-炔基或苯基，
R2为C1-C8-烷基(可任选地被氟、氯、氰或C1-C4-烷氧基取代)，C2-C8-烯基(可任选地被氟和/或氯取代)，C2-C8-炔基，C3-C6-环烷基(可任选地被氯和/或C1-C3-烷基取代)C5-或C6-环烯基，苯甲基(可任选被氟、氯和/或C1-C4-烷基取代)，苯基(可任选被氟、氯、溴、碘、氰、硝基、C1-C4-烷基、三氟甲基、C1-C4-烷氧基和/或C1-C4-烷硫基取代)，C1-C8-烷氧基(可任选被C1-C4-烷氧基取代)或C3-C4-烯氧基，或
R1-及R2与氮原子一起结合，可任选地一次到三次被C1-C3-烷基取代，并形成饱和或不饱和五到七节的氮杂环以及任选地与苯并基稠合及
R3为C1-C8-烷基(可任选地被氟、氯、溴、氰、C1-C4-烷氧基、二氧杂戊环基或二氧杂己环基取代)或为苯基或苯基-C1-C2-烷基(可任选被氟、氯、溴、氰、硝基、C1-C4-烷基或C1-C4-烷氧基取代)，上述已不包括在本发明式(I)化合物之内的化合物仍排除在外。
本发明特别优选涉及这样的式(1)表示的化合物，其中
n为1或2，
R1为甲基，乙基，正或异丙基，正、异或另丁基，正、异或另戊基(可任选被氟、氯、氰、甲氧基或乙氧基取代)丙烯基，丁烯基，丙炔基或丁炔基，
R2为甲基，乙基，正或异丙基，正、异或另丁基，正、异或另戊基，正、异或另己基(可任选被氟、氯、氰、甲氧基或乙氧基取代)，丙烯基，丁烯基，戊烯基，丙炔基，丁炔基或戊炔基，环戊基或环己基(可任选地被甲基和/或乙基取代)，环己烯基，苯甲基(可任选被氟，氯和/或甲基取代)或苯基(可任选被氟、氯、溴、氰、硝基、甲基、乙基、三氟甲基，甲氧基或乙氧基取代)，甲氧基、乙氧基、正或异丙氧基、正、异或另丁氧基、正、异或另戊氧基(可任选被甲氧基，乙氧基取代)或
R1及R2与氮原子一起结合成任选一次到三次被甲基和/或乙基取代的哌啶(Piperidinyl)基，任选一次或二次被甲基和/或乙基取代的吡咯烷基，全氢化氮杂基(Perhydroazepinyl)或1，2，3，4-四氢(异)喹啉基。
R3为甲基，乙基，正或异丙基，正、异、另或特丁基，正、异、另或特戊基(可任选被氟、氯、氰、甲氧基或乙氧基取代)，苯基或苯甲基(可任选被氟、氯、氰、甲基或甲氧基取代)。
前面已指明的不包括在本发明式I化合物之内的化合物仍排除在外。
式(1)中的原子团
可能出现的含义举例列入表1中表1：原子团含义的实例 
表1(续)表1(续)表1(续)表1(续)表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
前面列举的原子团的一般性以及优选范围的含义既适用于式(I)表示的最终产物也适用于制造该产物所需的相应原料及中间体。
这些基团的表示式可以互相任意组合，这也在优选化合物的给定的范围内。
例如，可用3-甲基亚磺酰基-5-氯-1，2，4-噻二唑与N-甲基-羟乙酰胺为原料按照本发明的制造方法(a)通过下述反应流程进行反应：
又例如，可用N-环己基-N-甲基-α-(3-甲基硫-1，2，4-噻二唑-5-基-氧)-乙酰胺与过氧化氢为原料按照本发明的制造方法(b)通过下述反应流程进行反应：
按照本发明的制造方法(a)制造通式(I)表示的化合物所用的原料1，2，4-噻二唑衍生物可用通式(II)表示。式(II)中的n及R3优选或特别优选的含义在前面描述式(I)表示的化合物时已经指明。
式(II)表示的原料除化合物，除了5-氯-3-甲基磺酰基-1，2，4-噻二唑及3，5-双甲基磺酰基-1，2，4-噻二唑(参阅Chem.Ber.97(1964)，225-237；德国公开说明书1544505)外尚未见之于已有文献中，因而除上述两个化合物外都属于本专利申请要求保护主题的一部分。
如果用式(V)表示的相应烷基硫代化合物，
式中R3及X同前面已指出的含义，与一种氧化剂如过氧化氢进行反应，根据需要可加入一种反应辅助剂如钨酸钠或硫酸，及稀释剂如水，甲醇、蚁酸和/或醋酸，反应温度在0℃与150℃之间，即可生成式(II)表示的1，2，4-噻二唑衍生物(参阅制造实例)。
式(V)表示的前体为已知的化合物和/或可按已知的方法制造(参阅Chem.Ber.90(1957)，892-901；loc.cit.97(1964)，225-237；东德专利说明书221060；制造实例)。
按本发明的制造方法(a)制造式(I)表示的化合物还可使用原料羟基乙酰胺，它可用通式(III)表示。
式(III)中的R1及R2的优选和特别优选的含义已在描述本发明的式(I)表示的化合物时予以指明。
式(III)表示的羟基乙酰胺为已知化合物和/或可按已知的方法制造(参阅US-P 4509971及US-P 4645525；以及US-P 4334073，DE-OS 3038598，DE-OS 3038636，EP-A 37526，EP-A348737，DE-OS 3819477)。
按照本发明的制造方法(b)制造通式(I)表示的化合物所用的原料烷基(芳基，芳烷基)硫-1，2，4-噻二唑基氧乙酰胺可用通式(IV)表示。式(IV)中的R1，R2，R3的优选及特别优选的含义同于已在描述式(I)表示的化合物时对R1，R2，R3所指明的。
式(IV)表示的原料化合物是已知的和/或可按已知的方法制造(参阅EP-A 018497，EP-A 029171)。
按照本发明的方法(a)制造式(I)表示的新型化合物烷基亚磺酰基及烷基磺酰基-1，2，4-噻二唑基氧乙酰胺时应优选使用稀释剂。这些稀释剂优选包括碳氢化合物如甲苯，二甲苯或环己烷；卤化碳氢化合物如氯代甲烷，氯代乙烷，氯仿或氢化苯；醚类如乙醚，丙醚，二异丙醚，丁醚，二异丁醚，乙二醇二甲醚，四氢呋喃及二噁烷；醇类如甲醇，乙醇，丙醇，异丙醇，丁醇，异丁醇，另丁醇特丁醇；酮类如丙酮，甲基乙基甲酮，甲基异丙基甲酮，甲基异丁基甲酮；酯类如醋酸甲酯及醋酸乙酯；酰胺类如二甲基甲酰胺、二甲基乙酰胺及N-甲基吡咯烷酮；腈类如乙腈及丙腈；亚砜类如二甲基亚砜以及水或各种盐类的水溶液。
作为盐类可优选使用碱金属或碱土金属的氯化物或硫酸盐，例如氯化钠，氯化钾，氯化钙。氯化钠特别被优选采用。
本发明的方法(a)中使用酸结合剂是有利的。作为酸结合剂可使用强碱性的碱金属及碱土金属的化合物例如氧化物如氧化钠，氧化钾，氧化镁，氧化钙；氢氧化物如氢氧化钠，氢氧化钾，氢氧化镁，氢氧化钙；醇化物如特丁醇钠，特丁醇钾和/或碳酸盐如碳酸钠，碳酸钾，碳酸镁，碳酸钙等。
在某些情况下加入0.01到10重量％(按使用的式(III)表示的乙二醇酰胺重量计算)的相转移催化剂是有利的。下面列举一些这种催化剂例子：
氯化四丁基铵，溴化四丁基铵，溴化三丁基甲基膦，氯化三甲基-C13/C15-烷基铵，甲基硫酸化二苯甲基-二甲基铵，氯化二甲基-C12/C14-烷基苯甲基铵，氢氧化四丁基铵，18-蔻-6，氯化三乙基苯甲基铵，氯化三甲基苯甲基铵，氯化四乙基铵。
本发明的方法(a)的操作温度可在较大范围内变化。一般情况是在-50℃及+110℃之间的温度下进行，优选在-20℃到+80℃之间的温度。
本发明的方法(a)一般在常压下操作，但是也可以增压或减压，约在0.1到10巴之间是可能的。
按照本发明方法(a)进行操作时一般可对每Mol式(II)表示的1，2，4-噻二唑衍生物加0.5到5Mol，优选0.8到1.5Mol式(III)表示的羟基乙酰胺。各种反应成份的加入顺序可以随意。反应混合物必须自始至终进行搅拌。反应生成物按常规的方法处理(参阅制造实例)。
按本发明的方法(b)制造式(I)表示的化合物要用氧化剂进行操作。这里可采用通常将有机硫化物(硫醚)氧化成相应的硫氧化物或砜(Sulphone)适用的化学药品。适用的氧化剂举例如下：过氧化氢、过蚁酸，过醋酸，过丙酸，过苯甲酸及3-氯过苯甲酸以及氯，次氯酸及其碱金属或碱土金属盐。
本发明的方法(b)有时要用催化剂。作为催化剂这里可用元素周期表中的IV，V，VI副族元素的金属盐，例如(偏)钒酸钠，钼酸钠及钨酸钠等。
本发明的方法(b)应优选加入稀释剂进行操作。这里可用的稀释剂除水外还可用通常氧化反应所用的有机溶剂，属于优选采用的有氯化的碳氢化物如氯代甲烷，氯代乙烷，氯仿，四氯甲烷，1，1，2-三氯乙烷，氯苯及邻二氯苯；醇类如甲醇，乙醇，丙醇，异丙醇，丁醇，异丁醇及另丁醇；酸类如蚁酸，醋酸及丙酸。
本发明的方法(b)的操作温度可在较大范围内变化。一般的操作温度在-20℃与+60℃之间，优选采用0℃到40℃之间。
本发明的方法(b)一般在常压下操作。但也可以在较高压或减压而一般在0.1巴及10巴之间进行操作。
本发明的方法(b)操作时对1Mol式(II)表示的原料一般用1到10Mol，优选用1到5Mol氧化剂，根据需要可用0.001到0.1Mol，优选用0.01到0.05Mol之间的催化剂。
本发明的方法(b)在一种优选采用的操作形式为先将式(II)表示的原料及按需要加入一种催化剂放在反应器中，在搅拌中缓慢加入氧化剂。反应混合物必须到反应进行完毕不断搅拌，最后按常规方法处理反应生成物(参阅制造实例)。
本发明的活性物质可用作脱叶剂，干燥剂，除莠剂，特别用作消除杂草的药物。所谓杂草，最广义人们理解为在指定土地上不希望生长的各种植物。本发明的活性物质是用作全面或有选择地消除杂草主要由使用的剂量决定。
本发明的活性物质可用于例如下列植物。双子叶杂草品种：
芥子，鳞皮草，格利草，繁缕，母菊，春黄菊，格林豆，藜，荨麻，千里光，鸡冠花，马齿苋，黄叶草，旋花，甘薯属杂草，多角豆，色斑豆，土荆芥，蘇，刺蓟，茄科植物，罗利白，白藤，林得草，拉明，婆婆纳，亚布提龙，伊米斯，曼陀罗，堇菜，格罗西，罂粟，三叶草，矢车菊，兰克鲁斯，塔克萨斯库等。双子叶农作物品种：
葛麻，紫藤，倍达花，飞燕草，菜豆，比苏，茄子，亚麻，甘薯，野菀豆，烟草，石松，花生，布拉西卡，山莴苣，古枯密，葫芦等，单子叶杂草品种：
棘皮草，狗尾草，刺芹，掌状草，布罗姆，豌豆草，爱洛草，臂形草，洛里草，雀麦，燕麦，莎草，高粱，随谷草，犬牙草，绒毛草，流苏草，箭头草，埃利草，锯齿草，旋叶草，伊莎草，蝶形草，指头草，剪股颖，脱毛草，无花草等。单子叶农作物品种：
欧鲁沙，玉米，三叶草，大麦，燕麦，西卡拉，高粱，黍，甘蔗，菠萝，天门冬，大蒜等。
可是本发明的活性物质的应用范围并不局限于上述植物品种，而是按照同一方式也可在别的植物上应用。
这些化合物按照不同的浓度可用来全部消除杂草，例如在工厂区，铁路沿线，道路及广场栽种树木或没有树木的地方。化合物也可用于永久性的苗圃的消除杂草工作，如森林，观赏植物，果木林，葡萄园，柑桔林，以及核桃，香焦，茶，橡胶，油棕，可可，浆果，酒花等栽培的场所，观赏及运动场地，牧场以及一年生农作物培养区的有选择的除草。
本发明式(I)表示的化合物特别适用于双子叶农作物栽培区有选择性的消除单子叶及双子叶杂草，主要是在生长期之前进行。
活性物质可制成通常采用的形式，如溶液，乳化液，喷洒粉末，悬浮液，粉状，尘状，膏状，可溶细末，粒状，制造悬浮液或乳化液的浓缩物，将活性物质浸渍在天然及合成的物料中以及包在聚合的塑料细粒内。
这些成形制品可按已知的方法制造，如将活性物质与液态溶剂和/或固态载体混合。根据要求加入表面活性剂，如乳化剂和/或分散剂和/或发泡剂之类。
用水作为稀释剂时也可用例如有机溶剂助溶。作为液态溶剂主要有芳香类如二甲苯，甲苯或烷基萘；氯化芳香族及氯化脂肪族碳氢化合物如氯苯，氯乙烯，氯甲烷；脂肪族碳氢化合物如环己烷或石蜡如石油分馏物，植物油等；醇类如丁醇或乙二醇以及醚类，脂类，酮类如丙酮，甲基乙基甲酮，甲基异丁基甲酮或环己酮；强极性的溶剂如二甲基甲酰胺，二甲亚砜及水等。
作为固态的载体可用：
铵盐，天然石粉如瓷土，陶土，滑石，白垩，石英，蛭石，蒙脱石及硅藻土等及合成石粉如高度分散的氧化硅，氧化铝，硅酸盐。制粒用的固态载体有粉碎及分级过的天然石料如方解石，大理石，浮石，海泡石，白云石等以及由无机物及有机物制造的粒状物质，如用锯末，椰子壳，玉米芯及烟草杆等；作为乳化剂及/或发泡剂例如非离子化及离子化的乳化剂，如聚氧乙烯的脂肪酸酯，聚氧乙烯的脂肪醇醚如烷基芳基聚甘醇醚，烷基磺酸盐，烷基硫酸盐，芳基磺酸盐以及蛋白质水解物；作为分散剂如木质素亚硫酸废液及甲基纤维素。
还可加些成型助剂如羧甲基纤维素，天然及合成粉状，粒状或乳胶状聚合物如阿拉伯胶，聚乙烯醇，聚乙烯乙酯以及磷脂类如脑磷脂，卵磷脂及合成脑磷脂。也可加矿物油及植物油作为添加剂。
还可加些颜料例如无机颜料如氧化铁，氧化钛，亚铁氰兰以及有机染料如茜素，偶氮及酞花青染料和少量营养物如铁，锰，硼，铜，钴，钼及锌的盐类。
成型后的物料中一般可含活性物质0.1到95重量％，优选采用0.5到90％。
本发明的活性物质可用原物或成型后的物料或与已知的除莠剂混合用来消除杂草。可以供应一定形状的成型物料或罐装混合物。
用来混合的已知除莠剂列举如下：
酰替苯胺如Diflufenican及Propanil；芳基碳酸如二氯皮考啉酸，Dicamba及Picloram；芳氧烷基酸如2，4-D，2，4-DB，2，4-DP，Fluroxypyr，MCPA，MCPP及Triclopyr；芳氧基-酚烷酸酯如Diclofop-甲基，Fenoxaprop-乙基，Fluazifop-丁基，Haloxyfop-甲基及Quizalofop-乙基；连氮酮如Chloridazon及Norflurazon；氨基甲酸酯如Chlorpropham，Desmedipham，Phenmedipham及Propham；氯乙酰苯胺如Alachlor，Acetochlor，Butachlor，Metazachlor，Metolachlor，Pretilachlor及Propachlor；二硝基苯胺如Oryzalin，Pendimethalin及Trifluralin；二苯醚如Acifluorfen，Bifenox，Fluoroglycofen，Formesafen，Halosafen，Lactofen及Oxyfluorfen；尿素如Chlortoluron，Diuron，Fluometuron，Isoproturon，Linuron及Methabenzthiazaron；羟胺如Alloxydim，Clethodim，Cycloxydim，Sethoxydim及Tralkoxydim；咪唑啉酮如Imazethapyr，Imazamethabenz，Imazapyr及Imazaquin；腈如Bromoxynil，Dichlobenil及Ioxynil；氧乙酰胺如Mefenacet；磺酰尿素如Amidosulfuron，Bensulfuron-甲基，Chlorimuron-乙基，Chlorsulfuron，Cinosulfuron，Metsulfuron-甲基，Nicosulfuron，Primisulfuron，Pyrazosulfuron-乙基，Thifensulfuron-甲基，Triasulfuron及Tribenuron-甲基；硫代氨基甲酸酯如Butylate，Cycloate，Diallate，EPTC，Esprocarb，Molinate，Prosulfocarb，Thiobencarb及Triallate；三氮杂苯如Atrazin，Cyanazin，Simazin，Simetryne，Terbutryne及Terbutylazin；三连氮酮如Hexazinon，Metamitron及Metribuzin；其他如Aminotriazol，Benfuresate，Bentazone，Cinmethylin，Clomazone，Clopyralid，Difenzoquat，Dithiopyr，Ethofumesate，Fluorochloridone，Glufosinate，Glyphosate，Isoxaben，Pyridate，Quinchlorac，Quinmerac，Sulphosate及Tridiphane。
还可与别的已知活性物质混合，例如灭菌剂，杀虫剂，灭丝虫剂，消灭寄生虫的以及防鸟害的物质，植物营养剂，土壤改良剂等。
活性物质可以原物或成型为各种形状或稀释后使用如常用的溶液，悬浮液，乳化液，粉末，浸膏以及制成颗粒。用时可以通过一般的方式，如浇灌，喷洒，喷射，散布等。
本发明的活性物质可在植物的生长期前也可在生长后期使用，还可以在播种之前耕进土壤里去。
使用的活性物质量也可在较大范围内变化。主要是根据所预期的效果选择。一般情况每公顷的活性物质使用量在10g到10kg之间，优选采用每公顷50g到5kg。
下面列举一些实施例来说明本发明的活性物质的制造及其使用情况。制造实施例：实例1
3.6g(15mMol)3，5-双甲苯磺酰基-1，2，4-噻二唑与2.6g(15mMol)羟基乙酰-2-乙基哌啶(piperidide)共同溶解在40ml丙酮中。然后在-20℃滴入0.6g氢氧化钠溶解在3.3ml水中的溶液。反应混合物在-15℃搅拌12小时后加水稀释到原来容积的两倍再加氯仿摇匀。分离出的有机物相用硫酸钠干燥后过滤。滤液在水喷射泵的真空中仔细蒸馏除去溶剂。
得到4.8g(理论值77％的)α-(3-甲基磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰-2-乙基哌啶(piperidide)油状物，其折射率为nD 20＝1.5329。实例2
29.5g(0.10Mol)α-(3-甲基硫-1，2，4-噻二唑-5-基-氧)-乙酰-N-甲基苯胺溶解在50ml氯甲烷中。加入100ml水后在搅拌中约3小时内导入17.75g(0.25Mol)氯气。接着将生成的有机物相分离出来。用水洗净后用硫酸钠吸去水份和过滤。在水喷射泵的真空中将滤液内的溶剂蒸馏出去，馏剩的物料加少量甲醇拌匀然后用吸滤法分离出结晶的产品。
获得7.0g(理论值的21％)α-(3-甲基磺酰-1，2，4-噻二唑-5-基-氧)-乙酰-N-甲基酰苯胺。其熔点为82℃。
用类似于制造实例1及2的方法按照本发明通用的制造方法描述还可制成例如下列表2中列举的式(I)表示的化合物。表2：式(I)表示的化合物的实例
表2：表2：
表2：表2：表2：表2：表2：
表2：
表2：
表2：
表2：表2：表2：
表2：表2：
表2：
表2：表2：
表2：
表2：表2：
表2：
表2：
表2：表2：
表2：
表2：
表2：
表2：表2：表2：
表2：表2：表2：表2：表2：
表2：
表2：
表2：表2：表2：
表2：
表2：表2：式(II)表示的原料化合物：实例(II-1)
148g(0.73Mol)5-氯-3-甲基硫-1，2，4-噻二唑溶解在500ml甲醇与23g浓硫酸的混合物中并装上回流装置加热。然后滴入90.6g(0.8Mol H2O2)的30％过氧化氢水溶液。反应混合物在回流条件下加热3小时后浓缩。剩余物加氯仿及水摇匀。分离出的有机物相先用碳酸氢钠溶液，后用水洗涤，然后用硫酸钠吸去水份再过滤。在水喷射泵真空中仔细将滤液中的溶剂蒸馏出去。
获得113g(理论值的85％)5-氯-3-甲基亚磺酰基-1，2，4-噻二唑的结晶产物，其熔点为72℃。
用类似于实例II-1的方法可制造例如下列化合物：
3-乙基亚磺酰基-，3-正丙基亚磺酰基-，3-异丙基亚磺酰基-，3-正丁基亚磺酰基-，3-异丁基亚磺酰基-，3-另丁基亚磺酰基-，3-苯甲基亚磺酰基-，3-(2-氯苯甲基)-亚磺酰基-，3-(3-氯苯甲基)-亚磺酰基-，3-(4-氯苯甲基)-亚磺酰基-，3-(3-三氟甲基苯甲基)-亚磺酰基-及3-(4-三氟甲基苯甲基)-亚磺酰基-5-氯-1，2，4-噻二唑。实例II-2
105g(0.5Mol)2，5-双乙基硫-1，2，4-噻二唑及3.5g钨酸钠加在260ml醋酸中。在20℃到30℃的温度下约90分钟的时间内滴入475ml(5.5Mol H2O2)30％的过氧化氢水溶液。反应混合物在20℃搅拌5小时后缓慢用2.5升水稀释。沉淀出的结晶物用吸滤法分离出。
获得100g(理论值的74％)2，5-双乙基硫酰基-1，2，4-噻二唑，熔点为42℃。
用类似实例(II-2)的方法可制成下列表3中列举的式(II)表示的化合物。
表3：式(II)表示的化合物实例
使用实例：
下面给出的使用实例中以下列化合物作为对比物质：N-异丙基-N-苯基-α-(3-甲基亚磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰胺(发表在EP-A 348737/LeA 26031，参阅实例28)。实例A前期显现(Pre-emergence)试验
溶剂：5份(重量)丙酮
乳化剂：1份(重量)烷芳基聚乙二醇醚
为了制备符合使用目的的活性化合物制剂，将1份(重量)活性物质与上述溶剂混合物。然后加入乳化剂，再用水稀释到所需浓度。
将试验用植物的种子播在普通的土壤中。24小时后将制备好的活性化合物制剂浇灌在土壤上并保持单位面积的水份适当而恒定。制备的活性化合物制剂的浓度并不重要，起决定性的主要是单位面积上活性物质的用量。三星期后将植物被损害的情况与未加处理的对照土壤的情况对比用损害百分数表示出来。
0％＝不起作用(与未处理的对照试样相同)
100％＝完全将植物消灭。
在这些试验中，按照制造实例号1，5，6，7，8，9，11，12，14，17，19，20，21，22，23，24，25，26，27，28，29，30，31，32，33，34，35，36，37，38，39，41，42制成的化合物与栽培的农作物如黄豆相安无事，而对于杂草与已知化合物(A)对比效果要强得多(参阅表A)。
本发明的另一些活性化合物及其使用量，试验用植物及试验结果在后面的表B中列出。其中的实例号均取自表2中的制造实例。表A：前期显现试验/温室大棚活性物质 使用量 棉花 洛里草 刺芹 豌豆草 格林豆
(g/ha)
250 0 20 0 50 20 250 0 90 95 95 95 250 0 80 95 90 100表A：(续)活性物质 使用量 棉花 洛里草 刺芹 豌豆草 格林豆
(g/ha)
250 0 70 80 80 100 250 0 50 90 80 100 250 0 40 90 70 100表A：(续)活性物质 使用量 棉花 洛里草 刺芹 豌豆草 格林豆
(g/ha)
250 0 95 100 95 95 250 0 95 90 95 100
250 0 70 30 70 100表A：(续)活性物质 使用量 棉花 洛里草 刺芹 豌豆草 格林豆
(g/ha)
250 0 95 90 70 100 250 0 90 90 95 100
250 10 70 95 80 100表A：(续)活性物质 使用量 棉花 洛里草 刺芹 豌豆草 格林豆
(g/ha) 250 40 70 95 95 100 250 20 80 95 95 100
250 0 95 95 100 95表A：(续)活性物质 使用量 棉花 洛里草 刺芹 豌豆草 格林豆
(g/ha)
250 0 80 95 100 95
250 20 95 95 100 95
250 0 95 90 100 95表A：(续)活性物质 使用量 棉花 洛里草 刺芹 豌豆草 格林豆
(g/ha)
250 0 95 90 95 95
250 0 95 90 100 95 250 20 95 95 100 95表A：(续)活性物质 使用量 棉花 洛里草 刺芹 豌豆草 格林豆
(g/ha)
250 0 40 90 90 95 250 20 95 95 95 95 250 0 95 95 95 95表A：(续)活性物质 使用量 棉花 洛里草 刺芹 豌豆草 格林豆
(g/ha) 250 0 90 95 95 100 250 0 95 95 100 95 250 0 90 95 100 100表A：(续)活性物质 使用量 棉花 洛里草 刺芹 豌豆草 格林豆
(g/ha)
250 0 40 95 95 95
250 20 50 95 95 95
250 0 95 95 100 100表A：(续)活性物质 使用量 棉花 洛里草 刺芹 豌豆草 格林豆
(g/ha)
250 0 70 95 95 95 250 0 95 95 95 100 250 0 100 90 95 90表A：(续)活性物质 使用量 棉花 洛里草 刺芹 豌豆草 格林豆
(g/ha) 250 0 95 50 95 50 表B：前期显现试验/温室大棚活性物 使用量 掌状草 棘皮 豌豆草 狗尾 鸡冠花 格林豆 马齿苋质号 草 草
(kg/ha)2 500 100 100 100 100 100 - 10046 500 95 80 80 90 100 70 -49 250 100 80 80 100 80 95 1001 500 100 100 95 100 100 100 1005 500 95 100 100 100 100 100 1006 500 100 100 95 100 100 100 1007 500 95 100 95 95 80 100 958 500 100 100 95 90 90 100 1009 500 95 100 80 100 50 100 10011 500 95 100 95 100 95 100 9512 500 95 100 80 95 - 100 -19 250 95 95 80 95 - 100 7014 500 95 100 90 100 100 100 10016 500 95 95 80 70 80 100 10017 500 100 80 95 95 95 100 9520 250 95 95 95 95 95 100 80 表B：(续)活性物质 使用量 掌状草 棘皮 豌豆草 狗尾 鸡冠花 格林豆 马齿苋号 草 草
(kg/ha)21 250 95 95 80 95 80 100 -22 500 95 95 100 95 80 95 10023 500 100 100 100 95 70 95 10024 500 100 100 100 100 100 95 10025 500 95 100 100 95 - 95 -26 500 95 100 100 95 - 95 -27 500 95 95 100 95 70 95 9528 500 100 100 100 100 70 95 10029 500 95 95 90 90 70 95 9530 500 100 95 100 100 80 95 10031 500 100 100 100 100 70 95 10032 500 100 95 95 100 70 100 10033 500 100 100 100 100 100 95 10034 500 100 100 100 95 95 100 10035 500 100 100 100 100 95 100 9036 500 100 100 95 100 95 95 100表B：(续)活性物 使用量 掌状草 棘皮草 豌豆 狗尾草 鸡冠花 格林豆 马齿苋质号 草
(kg/ha)37 500 100 100 100 100 90 100 10038 500 100 100 100 100 95 95 10039 500 100 100 100 100 95 100 10040 500 95 95 95 95 - - -41 500 100 100 95 100 - 90 -42 500 95 100 100 95 - 95 -190 250 100 100 100 95 95 95 95191 250 95 100 95 95 80 80 60194 500 100 95 100 100 100 95 100196 250 95 100 100 100 95 100 9553 250 95 100 95 95 - 95 70198 250 100 100 100 95 90 100 95199 250 95 100 100 100 60 95 9555 250 95 100 100 100 100 90 9556 250 100 100 100 100 100 95 9557 250 100 100 100 100 100 100 100表B：(续)活性物质 使用量 掌状草 棘皮草 豌豆 狗尾草 鸡冠花 格林豆 马齿苋号 草
(kg/ha)58 250 100 100 100 100 100 95 90201 250 100 100 100 100 95 95 60203 250 100 100 100 95 100 95 9075 500 100 95 100 100 70 95 95207 500 100 100 100 95 100 95 100208 500 95 100 100 100 100 95 10078 500 100 100 100 100 100 100 10079 500 100 100 100 100 100 100 10080 500 100 100 100 100 100 100 10087 500 95 50 95 95 80 100 95210 500 95 100 95 100 100 100 95212 500 95 60 95 95 100 100 100213 500 95 90 95 95 100 95 50310 250 100 100 95 95 100 95 95216 250 95 95 100 100 95 100 100219 250 100 100 100 95 - 100 100表B：(续)活性物 使用量 掌状草 棘皮草 豌豆 狗尾草 鸡冠花 格林豆 马齿苋质号 草
(kg/ha)220 250 100 100 100 100 100 100 100221 250 95 95 100 100 60 100 95103 250 100 100 100 100 50 100 100116 250 95 95 100 100 - 90 -222 250 95 100 100 95 - 100 70225 250 100 100 100 100 100 100 100226 250 95 80 100 100 100 100 100227 250 100 70 100 95 100 100 100228 250 100 100 100 100 100 95 100229 250 100 90 80 95 - 95 60230 250 95 95 100 95 95 60 -235 250 100 95 100 95 95 95 95236 250 95 80 90 90 - - -237 250 95 95 100 95 95 95 60240 250 100 95 100 100 90 95 95243 500 100 - 100 95 100 100 100表B：(续)活性 使用量 掌状 棘皮 豌豆 狗尾 鸡冠 格林 马齿物质号 (kg/ha) 草 草 草 草 花 豆 苋247 250 100 100 100 100 100 95 100251 250 100 95 100 90 100 100 95
Claims (9)
1.烷基亚磺酰基-和烷基磺酰基-1，2，4-噻二唑基氧乙酰胺，如下通式(I)所示
式中
n为1或2，
R1为氢或为烷基，烯基，炔基或芳烷基，它们可以是取代或未取代的，
R2为烷基，烯基，炔基，环烷基，环烯基，芳烷基，芳基，烷氧基，烯氧基或炔氧基，它们可以是取代或未取代的，或
R1与R2和氮原子一起结合成取代或未取代的，饱和的或不饱和的氮杂环，它还可含其他杂原子和与一个苯并基稠合，
R3为烷基，芳基或芳烷基，它们可以是取代或未取代的，其中：化合物N-异丙基-α-(3-甲基亚磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰苯胺，N-异丙基-α-(3-甲基磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰苯胺， N-异丙基-α-(3-乙基亚磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰苯胺，N-异丙基-α-(3-乙基磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰苯胺，N-异丙基-α-(3-丙基亚磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰苯胺，N-异丙基-α-(3-丙基磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰苯胺，和化合物：N-甲基-N-(4-氟-苯基)-α-(3-甲基亚磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰胺，N-甲基-N-(4-氟-苯基)-α-(3-甲基磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰胺，N-甲基-N-(4-氟-苯基)-α-(3-乙基磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰胺，N-乙基-N-(4-氟-苯基)-α-(3-甲基亚磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰胺，N-乙基-N-(4-氟-苯基)-α-(3-甲基磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰胺和N-乙基-N-(4-氟-苯基)-α-(3-乙基磺酰基-1，2，4-噻二唑-5-基-氧)-乙酰胺排除在外。
2.按照权利要求1中式(I)的化合物，其特征在于，
n为1或2
R1为氢或C1-C8-烷基(可任选被氟，氯，氰或C1-C4-烷氧基取代)，C2-C8-烯基(可任选被氟和/或氯取代)，C2-C8-炔基或苯基，
R2为C1-C8-烷基(可任选地被氟，氰或C1-C4-烷氧基取代)，C2-C8-烯基(可任选被氟和/或氯取代)，C2-C8-炔基，C3-C6-环烷基(可任选被氯及/或C1-C3-烷基取代)C5-或C6-环烯基，苯甲基(可任选被氟，氯及/或C1-C4-烷基取代)，苯基(可任选被氟，氯，溴，碘，氰，硝基，C1-C4-烷基，三氟甲基，C1-C4-烷氧基和/或C1-C4-烷硫基取代)，C1-C8-烷氧基(可任选被C1-C4-烷氧基取代)或C3-C4-烯氧基或
R1与R2与氮原子一起结合，可任选地一到三次被C1-C3-烷基取代，形成饱和或不饱和五到六节的氮杂环以及与苯并基稠合，
R3为C1-C8-烷基(可任选被氟，氯，溴，氰，C1-C4-烷氧基，二氧杂戊环基，二氧杂己环基取代)或为苯基或苯基-C1-C2-烷基(可任选被氟，氯，溴，氰，硝基，C1-C4-烷基或C1-C4-烷氧基取代)，如权利要求1中已指明的放弃的那些化合物排除在外。
3.按照权利要求1式(I)的化合物，其特征在于式中
n为1或2，
R1为甲基，乙基，正或异丙基，正、异或另丁基，正、异或另戊基(可任选被氟，氯，氰，甲氧基或乙氧基取代)丙烯基，丁烯基，丙炔基或丁炔基，
R2为甲基，乙基，正或异丙基，正、异或另丁基，正、异或另戊基，正、异或另己基(可任选被氟、氯、氰、甲氧基或乙氧基取代)，丙烯基，丁烯基，戊烯基，丙炔基，丁炔基，戊炔基，环戊基或环己基(可任选被甲基及/或乙基取代)，环己烯基，苯甲基(可任选被氟，氯及/或甲基取代)或苯基(可任选被氟、氯、溴、氰、硝基、甲基、乙基、三氟甲基、甲氧基或乙氧基取代)，甲氧基，乙氧基，正或异丙氧基，正、异或另丁氧基，正、异或另戊氧基(可任选被甲氧基或乙氧基取代)或
R1与R2与氮原子一起结合成任选一次到三次被甲基和/或乙基取代的哌啶基，任选一或二次被甲基和/或乙基取代的吡咯烷基，全氢化氮杂基或1，2，3，4-四氢(异)喹啉基及
R3为甲基，乙基，正或异丙基，正、异、另或特丁基，正、异、另或特戊基(可任选被氟、氯、氰、甲基或乙基取代)，苯基或苯甲基(可任选被氟、氯、氰、甲基或甲氧基取代)，如权利要求1中已指明的放弃的那些化合物排除在外。
4.权利要求1式(I)的烷基亚磺酰基及烷基磺酰基-1，2，4-噻二唑基氧乙酰胺的制造方法，其特征在于
(a)通式(II)表示的1，2，4-噻二唑的衍生物式中
X为卤素或原子团-S(O)n-R3和其中
n及R3具有权利要求1中的规定的含义，与通式(III)表示羟基乙酰胺进行反应
式中
R1及R2具有权利要求1中规定的含义，如果需要可在一种稀释剂，一种酸结合剂及一种催化剂的存在下反应或
(b)由通式(IV)表示的烷基(芳基-，芳烷基-)硫-1，2，4-噻二唑基氧乙酰胺
式中
R1，R2及R3具有权利要求1中规定的含义，与一种氧化剂，如需要可在一种催化剂及一种稀释剂参加条件下进行反应。
5.除莠剂，其特征在于最少含有一种权利要求1中提出的式(I)表示的化合物。
6.权利要求1中提出的通式(I)表示的化合物在控制不希望出现的植物的生长方面的应用。
7.控制杂草的方法，其特征在于用权利要求1中提出的通式(I)表示的化合物直接作用于杂草或其生存的空间。
8.除莠剂的制造方法，其特征在于将权利要求1中提出的通式(I)表示的化合物与稀释剂和/或表面活性剂混合。
9.通式(II)表示的1，2，4-噻二唑衍生物，式中
X为卤素或原子团-S(O)n-R3，
n为1或2和
R3为烷基，芳基或芳烷基可以是取代或未取代，以下化合物除外：5-氯-3-甲基磺酰基-1，2，4-噻二唑及3，5-双甲基磺酰基-1，2，4-噻二唑。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4415338.4 | 1994-05-02 | ||
| DE4415338A DE4415338A1 (de) | 1994-05-02 | 1994-05-02 | Alkylsulfinyl- und Alkylsulfonyl-1,2,4-thiadiazolyloxyacetamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1151738A true CN1151738A (zh) | 1997-06-11 |
| CN1073561C CN1073561C (zh) | 2001-10-24 |
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| CN95193810A Expired - Fee Related CN1073561C (zh) | 1994-05-02 | 1995-04-19 | 烷基亚磺酰基与烷基磺酰基－1,2,4－噻二唑基氧乙酰胺及其作为除莠剂的应用 |
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|---|---|
| US (1) | US5827800A (zh) |
| EP (1) | EP0758326B1 (zh) |
| JP (1) | JPH09512281A (zh) |
| KR (1) | KR100369704B1 (zh) |
| CN (1) | CN1073561C (zh) |
| AU (1) | AU2406995A (zh) |
| DE (2) | DE4415338A1 (zh) |
| WO (1) | WO1995029905A1 (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1321117C (zh) * | 2002-10-11 | 2007-06-13 | 住友化学株式会社 | 噻二唑化合物及其用途 |
| CN103113322A (zh) * | 2013-02-05 | 2013-05-22 | 浙江省诸暨合力化学对外贸易有限公司 | 噻二唑酰胺衍生物合成方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1475374A4 (en) * | 2002-01-17 | 2005-05-04 | Sumitomo Chemical Co | THIADIAZONE COMPOUNDS AND THEIR USE |
| DE60227714D1 (de) * | 2002-11-08 | 2008-08-28 | Sumitomo Chemical Co | 1,2,4-thiadiazolverbindungen und deren anwendung |
| CN108117528B (zh) * | 2018-01-29 | 2021-04-30 | 贵州大学 | 2,5-取代基-1,3,4-噁二唑砜类衍生物、其制备方法及应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0018497B1 (de) * | 1979-04-06 | 1982-04-28 | Bayer Ag | Azolyloxy-essigsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
| DE2946524A1 (de) * | 1979-11-17 | 1981-06-11 | Bayer Ag, 5090 Leverkusen | Azolyloxy-carbonsaeure-n-oxy-amide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3821600A1 (de) * | 1988-06-27 | 1989-12-28 | Bayer Ag | Heteroaryloxyessigsaeure-n-isopropylanilide |
| DE4317323A1 (de) * | 1993-05-25 | 1994-12-01 | Bayer Ag | N-(4-Fluor-phenyl)-heteroaryloxyacetamide |
-
1994
- 1994-05-02 DE DE4415338A patent/DE4415338A1/de not_active Withdrawn
-
1995
- 1995-04-19 WO PCT/EP1995/001472 patent/WO1995029905A1/de active IP Right Grant
- 1995-04-19 AU AU24069/95A patent/AU2406995A/en not_active Abandoned
- 1995-04-19 JP JP7527963A patent/JPH09512281A/ja active Pending
- 1995-04-19 US US08/732,239 patent/US5827800A/en not_active Expired - Fee Related
- 1995-04-19 CN CN95193810A patent/CN1073561C/zh not_active Expired - Fee Related
- 1995-04-19 KR KR1019960706128A patent/KR100369704B1/ko not_active IP Right Cessation
- 1995-04-19 EP EP95917938A patent/EP0758326B1/de not_active Expired - Lifetime
- 1995-04-19 DE DE59509781T patent/DE59509781D1/de not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1321117C (zh) * | 2002-10-11 | 2007-06-13 | 住友化学株式会社 | 噻二唑化合物及其用途 |
| CN103113322A (zh) * | 2013-02-05 | 2013-05-22 | 浙江省诸暨合力化学对外贸易有限公司 | 噻二唑酰胺衍生物合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE4415338A1 (de) | 1995-11-09 |
| CN1073561C (zh) | 2001-10-24 |
| WO1995029905A1 (de) | 1995-11-09 |
| US5827800A (en) | 1998-10-27 |
| EP0758326B1 (de) | 2001-10-31 |
| KR100369704B1 (ko) | 2003-04-16 |
| AU2406995A (en) | 1995-11-29 |
| JPH09512281A (ja) | 1997-12-09 |
| EP0758326A1 (de) | 1997-02-19 |
| DE59509781D1 (de) | 2001-12-06 |
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