IL31444A - Pesticidal preparations containing trifluoromethyl-phenyl-(thio)ureas and certain new such compounds - Google Patents
Pesticidal preparations containing trifluoromethyl-phenyl-(thio)ureas and certain new such compoundsInfo
- Publication number
- IL31444A IL31444A IL31444A IL3144469A IL31444A IL 31444 A IL31444 A IL 31444A IL 31444 A IL31444 A IL 31444A IL 3144469 A IL3144469 A IL 3144469A IL 31444 A IL31444 A IL 31444A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- composition according
- active ingredient
- compounds
- group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 20
- 230000000361 pesticidal effect Effects 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 7
- 235000013877 carbamide Nutrition 0.000 title description 4
- 150000003672 ureas Chemical class 0.000 title description 3
- 241000196324 Embryophyta Species 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- -1 2-me hylpropynyl Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 230000002363 herbicidal effect Effects 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 241000894006 Bacteria Species 0.000 claims description 3
- 241000233866 Fungi Species 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 244000068988 Glycine max Species 0.000 claims description 2
- 235000010469 Glycine max Nutrition 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 240000008042 Zea mays Species 0.000 claims description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 235000009973 maize Nutrition 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 230000003032 phytopathogenic effect Effects 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 241000219146 Gossypium Species 0.000 claims 1
- 240000007594 Oryza sativa Species 0.000 claims 1
- 235000007164 Oryza sativa Nutrition 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 235000013339 cereals Nutrition 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 235000009566 rice Nutrition 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000080 wetting agent Substances 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- 241000223602 Alternaria alternata Species 0.000 description 1
- 241000213004 Alternaria solani Species 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000339490 Brachyachne Species 0.000 description 1
- ASMZBOYDOWEBKG-UHFFFAOYSA-L Cl(=O)(=O)[O-].[Na+].[Na+].Cl(=O)(=O)[O-] Chemical compound Cl(=O)(=O)[O-].[Na+].[Na+].Cl(=O)(=O)[O-] ASMZBOYDOWEBKG-UHFFFAOYSA-L 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000801118 Lepidium Species 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000003559 chemosterilizing effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125961 compound 24 Drugs 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 229910052571 earthenware Inorganic materials 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/18—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/16—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms
- C07D203/20—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms by carbonic acid, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
preparations containing and certain new euoh oompounde AO Oi29736 2 The present invention provides herbicidal positions which as active at least one compound of the general formula in which X and represents an oxygen or a sulphur represents a or methoxy grou phenyl group which may he or by or or phon lalkyl group having 1 to carbon atoms in the alkyl and represents hydrogen or a alkyl or and together with nitrogen atom to they are attached form a to 7 saturated monocyclic heterocycle or a or pholino and an alkoxyalkyl or alkylthioalkyl group with 1 to 4 carbon atoms in eaoh alkyl together with a suitable The new preparations may contain one or more o the following a a a an a an adhesive and other pesticidal Israeli Patent Specification 21685 discloses anthelmintic urea and thiourea derivatives in which one of the phenyl rings carries a trifluoromethyl 5 in each case possibly with a further of a primary amino group further in the phenyl to obtain the desired phenylurea formula The new compounds above a selective activity against weeds in cultures of useful This activity can be produced by the and post method and is primarily observed in important scale cultures for example soybeans or A total herbicidal activity is produced when applying larger amounts of the This is always advantageous when the cultured soil is to be prepared for fresh while residues of a previous still remain in Some of the compounds act also as When used in very minor the new phenylureas display a good microbicidal activity against bacteria and for example against Aspergillus Staphylococcus Escherichia coli or Rhizoctonia for which purpose the compounds and 24 in the following Table I are especially They also display good activity against for example Alternaria tenuis or Alternaria solani or against the soil fungus which can be especially successfully combated with the compound Compound 9 for fu thermore displays a chemosterilizing action against The new ureas of the formula I may be formulated into pesticidal preparations in dry or liquid form as Specification 3 British 1 047 and Swiss In many it is advantageous to use granulates to ensure that the active substance is given off uniformly over a prolonged period of Such granulates can be prepared by dissolving the active substance in an organic absorbing this solution a granulated for example attapulgite or and removing the Whatever form of application of the preparations is it may be distributed dusting or the over a large area by The various forms of application of such preparations can be adapted to the particular use by admixture of known substances that improve the stability to rain and possibly the such substances for fatty wetting casein or For the manufacture of herbicidal numerous components may further be The most important of these are mentioned dimethylurea trichloroacetic 2 2 3 2 2 isopropylcarbanilate acid and salts different sodium sodium chlorate and sulphamic The preparations of this invention may also be used in combination with fungicides or The following Examples illustrate the the parts being by EXAMPLE 1 A solution of 33 parts of phenylisocyanate in 50 cc of acetonitrile is added drop by drop to a solution of 20 cc of dimethylamine aqueous in 100 cc of whilst vigorously The reaction product is precipitated with water and filtered it melts at In an identical manner the following compounds were TABLE 1 R 86 89 o 129 oil 16 89 then also the following Compound Compound 0 124 of finely divided Si02 marketed under the trade name of a condensation product of 1 mol of with 12 moles of ethylene oxide of a condensation product of with 9 nols of ethylene The finely ground mixture can be diluted with water in any desired proportion to form a spray broth ready for EXAMPLE 3 In a greenhouse earthenware pots were filled with earth and seeded with several of the following kinds of Triticum Hordeum Beta Sinapis Lepidium Cynodon Galium and The post emergent treatment of the plants mentioned was carried out with a and an aqueous solution of one of the compounds described in Example 1 some 10 to 12 days after in the leaf in an amount of 2 kg of active substance per Evaluation was carried out about 20 days after the treatment and revealed the results shown in Table The treatment was carried out with the same amount of active substance before 24 hours after seedinga 1 plant at most only slightly affected 4 6 medium damage 7 8 heavy damage 9 plant From the test it is seen that compounds 1 and 24 are suitable for use as weed control agents in wheat cultures both in the pre and the Oompoundo havo a broador they and also tolerates but destroy the weeds whioh Compound 24 is a typical selective herbicide for the protection of cotton cultures by the pre Compound 26 is suitable as a weed control agent in maize it is especially advantageous in cases where the application of triazine derivatives over many years have failed to destroy all the because types of weeds that had once been unimportant have now come into the and are hardly attacked by EXAMPLE 4 A special field test in which compound 1 was teste in winter wheat revealed the following results During tillering in a field of winter whea was treated with 1 kg of active substance per the field was infested with the natural weeds Poa Apera Stellaria and The evaluation was carried out namely after 4 and 8 weeks and revealed that all weed mentioned had been EXAMPLE 5 The new ureas and thioureas of the formula have a strong action against especially against staphylococci and The antibacterial activity in the dilution test was determined as Bacteriostasis 20 mg of active substance are dissolved in 1 0 ml of ml of this solution is added to ml of sterile glucose broth and then further diluted in the tubes 1 1 These solutions are then inoculated with Staphylococcus aureus and incubated for 48 hours at After this the following values in ppm inhibitory of the effect were Compound aureus Bakteriostasis 3 5 6 17 5 EXAMPLE 6 In a greenhouse e pots were filled with earth and seeded with the following kinds of The reatment of the plants mentioned was carried out with a aqueous solution of each the pounds 2 to 29 described in Example some 10 to 12 days after in the leaf an amount of 2 kg of active substance per Evaluation was carried out about 20 days the treatment and svealed the results shown in Table The treatment was oarried out with the same amount of active substance before 24 hours after 1 3 plant at most only slightly affected medium damage 7 8 heavy damage 18 t 19 insufficientOCRQuality
Claims (8)
1. Herbicidal compositions which contain as active ingredient, at least one compound of the general formula in which X and Y eaoh represents an oxygen or a sulphur atom; R. represents a CL-C. alkyl* allyl, 2-me hylpropynyl, 2,2- dimethoxyethyl or methoxy group, a phenyl group which may be mono- or disubstltuted by . chlorine, -CF^, -CH^ or -OCH^; or v ■ «eie4¾H and Rg represents hydroge or a C^- ^ aikyl group,, or R^ and Rg together with the nitrogen atom to which they are attached form a 3 to 7 membered saturated monocyclic hetero- cycle or a morpholino, methylmorpholino or dimethylmorpholino group; and a kenyl» an alkoxyalkyl or alkylthioalkyl group with 1 to 4 carbon alaas in each alkyl moiety, together with a suitable carrier.
2. A Composition according to Claim 1, wherein there is alap present one or more of the following additives: a vehicle a solvent, a diluent, a dispersant, an emulsi ier, a wetting agent, an adhesive or further pesticidal agents.
3. Compounds of the formula I in Claim 1, in which X, Y, g and ^ have the same meaning as in Claim 1 and ^ represent a O^-C^ alkyl, allyl, 2-methylpropynyl, 2, 2~diraetnpxyethyV»/ or 31444/3 - 21 -
4. 8. Th© compound of the formula 0 CH2CH2-0-C2H5 Compounds according to Claim 3 and substantially described in Example 1 herein. 31444/2 j - 22 - AV. A composition acoording to Olaim 1 or 2, wherein the active ingredient is a compound as claimed in Claim 3* ti» A composition according to Claim 1 or 2, wherein the active ingredient is a compound as claimed in Claim 4· A composition according to Claim 1 or 2, wherein the active ingredient is a compound as claimed in Claim
5. A composition according to Claim 1 or 2, wherein the active ingredient is the compound as claimed in Claim
6. A composition according to Claim 1 or 2, wherein the active Ingredient is a compound as claimed in Claim 7* $» A composition according to Claim 1 or.2, wherein the active ingredient is the compound as claimed in Claim 8. ti* A composition according to Claim 1 and substantially as described in any one of Examples 2 - 6 herein. %$* A method of selectively, treating weeds in a crop area which oomprlses applying to the crop area a compound according to Claim 3, using either the pre-emergent or post-emergent process* %· A method of selectively treating weds in a cro area, which comprises applying to the crop area a composition according to Olaim 1, using either the pre-emergent or post-emergent process. 7 8 2*0· A method according to Claim 1$ or 1 , wherein the crop area contains cereals, rice, maize, soybeans or cotton. 31444/3 - 23 -
20. A method of controlling phytopathogenic fungi and "bacteria, which comprises applying thereto a compound according to Claim 3.
21. . A method of controlling phytopathogenic fungi and bacteria, which comprises applying thereto a composition according to Claim 1, For the Applicants ND/ru
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH102268A CH493195A (en) | 1968-01-23 | 1968-01-23 | Pesticides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL31444A0 IL31444A0 (en) | 1969-03-27 |
| IL31444A true IL31444A (en) | 1973-03-30 |
Family
ID=4200614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31444A IL31444A (en) | 1968-01-23 | 1969-01-19 | Pesticidal preparations containing trifluoromethyl-phenyl-(thio)ureas and certain new such compounds |
Country Status (15)
| Country | Link |
|---|---|
| BE (1) | BE727286A (en) |
| BG (1) | BG17267A3 (en) |
| CH (1) | CH493195A (en) |
| CS (1) | CS158236B2 (en) |
| DE (1) | DE1901501C3 (en) |
| DK (1) | DK124443B (en) |
| FR (1) | FR2000570A1 (en) |
| GB (1) | GB1260386A (en) |
| IE (1) | IE32624B1 (en) |
| IL (1) | IL31444A (en) |
| NL (1) | NL159091B (en) |
| RO (1) | RO54785A (en) |
| SE (1) | SE375095B (en) |
| SU (1) | SU404191A3 (en) |
| YU (1) | YU34874B (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3222974A1 (en) * | 1982-06-19 | 1983-12-22 | Basf Ag, 6700 Ludwigshafen | NEW 5-PHENOXYBENZISOTHIAZOL-4'-UREA DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES |
| EP0427963B1 (en) * | 1989-11-10 | 1994-03-30 | Agrolinz Agrarchemikalien Gesellschaft M.B.H. | Process for the preparation of pure asymmetric disubstituted urea |
| DE10029564A1 (en) | 2000-06-22 | 2002-01-03 | Continental Ag | elastomeric bearings |
| AU2003243921B2 (en) | 2002-06-27 | 2009-05-07 | Novo Nordisk A/S | Aryl carbonyl derivatives as therapeutic agents |
| WO2005066145A1 (en) | 2004-01-06 | 2005-07-21 | Novo Nordisk A/S | Heteroaryl-ureas and their use as glucokinase activators |
| ES2382815T3 (en) | 2005-07-08 | 2012-06-13 | Novo Nordisk A/S | Dicycloalkylcarbamoyl ureas as glucokinase activators |
| US7884210B2 (en) | 2005-07-14 | 2011-02-08 | Novo Nordisk A/S | Ureido-thiazole glucokinase activators |
| US8138185B2 (en) | 2007-01-09 | 2012-03-20 | Novo Nordisk A/S | Urea glucokinase activators |
| US8318778B2 (en) | 2007-01-11 | 2012-11-27 | Novo Nordisk A/S | Urea glucokinase activators |
| KR20210020866A (en) | 2018-06-12 | 2021-02-24 | 브이티브이 테라퓨틱스 엘엘씨 | The therapeutic use of glucokinase activators in combination with insulin or insulin analogues |
| WO2021167840A1 (en) | 2020-02-18 | 2021-08-26 | Vtv Therapeutics Llc | Sulfoxide and sulfone glucokinase activators and methods of use thereof |
| EP4161640A4 (en) | 2020-06-08 | 2024-01-17 | vTv Therapeutics LLC | SALTS OR COCRYSTALS OF {2-[3-CYCLOHEXYL-3-(TRANS-4-PROPOXY-CYCLOHEXYL)-UREIDO)-THIAZOLE-5-YLSULFANYL}-ACETIC ACID AND USES THEREOF |
-
1968
- 1968-01-23 CH CH102268A patent/CH493195A/en not_active IP Right Cessation
-
1969
- 1969-01-14 DE DE1901501A patent/DE1901501C3/en not_active Expired
- 1969-01-16 FR FR6900613A patent/FR2000570A1/fr not_active Withdrawn
- 1969-01-19 IL IL31444A patent/IL31444A/en unknown
- 1969-01-21 SE SE6900757A patent/SE375095B/xx unknown
- 1969-01-21 IE IE80/69A patent/IE32624B1/en unknown
- 1969-01-22 BE BE727286D patent/BE727286A/xx unknown
- 1969-01-22 YU YU154/69A patent/YU34874B/en unknown
- 1969-01-22 NL NL6901066.A patent/NL159091B/en not_active IP Right Cessation
- 1969-01-22 DK DK34469AA patent/DK124443B/en unknown
- 1969-01-23 GB GB3873/69A patent/GB1260386A/en not_active Expired
- 1969-01-23 SU SU1300475A patent/SU404191A3/ru active
- 1969-01-23 CS CS45669*#A patent/CS158236B2/cs unknown
- 1969-01-23 RO RO58846A patent/RO54785A/ro unknown
- 1969-01-23 BG BG011505A patent/BG17267A3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE32624L (en) | 1969-07-23 |
| YU15469A (en) | 1979-10-31 |
| CH493195A (en) | 1970-07-15 |
| YU34874B (en) | 1980-04-30 |
| NL6901066A (en) | 1969-07-25 |
| IE32624B1 (en) | 1973-10-03 |
| NL159091B (en) | 1979-01-15 |
| SU404191A3 (en) | 1973-10-26 |
| DK124443B (en) | 1972-10-23 |
| RO54785A (en) | 1973-05-17 |
| BG17267A3 (en) | 1973-07-25 |
| FR2000570A1 (en) | 1969-09-12 |
| CS158236B2 (en) | 1974-10-15 |
| DE1901501A1 (en) | 1969-08-28 |
| DE1901501B2 (en) | 1977-09-22 |
| DE1901501C3 (en) | 1978-05-03 |
| IL31444A0 (en) | 1969-03-27 |
| BE727286A (en) | 1969-07-22 |
| SE375095B (en) | 1975-04-07 |
| GB1260386A (en) | 1972-01-19 |
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