DE2650362A1 - HERBICIDAL AGENTS AND METHOD FOR ITS MANUFACTURING - Google Patents
HERBICIDAL AGENTS AND METHOD FOR ITS MANUFACTURINGInfo
- Publication number
- DE2650362A1 DE2650362A1 DE19762650362 DE2650362A DE2650362A1 DE 2650362 A1 DE2650362 A1 DE 2650362A1 DE 19762650362 DE19762650362 DE 19762650362 DE 2650362 A DE2650362 A DE 2650362A DE 2650362 A1 DE2650362 A1 DE 2650362A1
- Authority
- DE
- Germany
- Prior art keywords
- tert
- butyl
- active ingredients
- triazine
- isopropylamino
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 14
- 239000004009 herbicide Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000004480 active ingredient Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- VHXDHGALQPVNKI-UHFFFAOYSA-N thiadiazol-4-ylurea Chemical compound NC(=O)NC1=CSN=N1 VHXDHGALQPVNKI-UHFFFAOYSA-N 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 5
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims description 4
- 241000196324 Embryophyta Species 0.000 claims description 4
- 240000000111 Saccharum officinarum Species 0.000 claims description 3
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 3
- 231100001184 nonphytotoxic Toxicity 0.000 claims description 2
- 241001483078 Phyto Species 0.000 claims 2
- 239000004202 carbamide Substances 0.000 description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 239000012141 concentrate Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000007900 aqueous suspension Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 4
- 229920005552 sodium lignosulfonate Polymers 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- 239000007798 antifreeze agent Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- HBPDKDSFLXWOAE-UHFFFAOYSA-N Tebuthiuron Chemical compound CNC(=O)N(C)C1=NN=C(C(C)(C)C)S1 HBPDKDSFLXWOAE-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
- 239000000230 xanthan gum Substances 0.000 description 2
- 235000010493 xanthan gum Nutrition 0.000 description 2
- 229940082509 xanthan gum Drugs 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- UGDWWCJKEUBONY-UHFFFAOYSA-N 6-chloro-6-methylcyclohexa-1,3-dien-1-ol Chemical compound CC1(Cl)CC=CC=C1O UGDWWCJKEUBONY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- -1 alkyl succinates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- CRPOUZQWHJYTMS-UHFFFAOYSA-N dialuminum;magnesium;disilicate Chemical compound [Mg+2].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] CRPOUZQWHJYTMS-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- ZAQDQFFQEKUULQ-UHFFFAOYSA-N nitrooxy(phenyl)mercury;phenylmercury;hydrate Chemical compound O.[Hg]C1=CC=CC=C1.[O-][N+](=O)O[Hg]C1=CC=CC=C1 ZAQDQFFQEKUULQ-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
- A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/12—Powders or granules
- A01N25/14—Powders or granules wettable
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Description
Anmelder: Lilly Industries Limited Applicant : Lilly Industries Limited
Henrietta House, Henrietta Place London ¥.1 / EnglandHenrietta House, Henrietta Place London ¥ .1 / England
Mittel mit herbicider Wirkung und
Verfahren z,u seiner HerstellungMeans with herbicidal effects and
Process z, u its manufacture
Die Erfindung betrifft neue herbicide Mittel^ Verfahren zu ihrer Herstellung und Verfahren zur Kontrolle von Unkraut in Zuckerrohranbaugebieten mit diesen Mitteln oder die Behandlung von Unkraut getrennt mit den Komponenten des Mittels.The invention relates to new herbicidal agents ^ methods on their production and methods of controlling weeds in sugar cane growing areas by these means or the treatment of weeds separately with the components of the remedy.
709821 /0996709821/0996
Gegenstand der Erfindung ist ein neues Mittel, das dadurch gekennzeichnet ist, daß es enthält: einen Thiadiazolyl iiarnstoff der Formel (I)The invention relates to a new agent which is characterized in that it contains: a thiadiazolyl iurea of formula (I)
N NN N
Ii CH, t«Ii CH, t «
S NS N
^C- NHCH, η J O ^ C- NHCH, η J O
R Trifluormethyl, tert.-Butyl oder Äthylsulfonyl bedeutet, R is trifluoromethyl, tert-butyl or ethylsulfonyl,
2-Chlor-4-äthylamino-6-isopropylamino-1,3,5-triazin und einen nicht-phytotoxischen Träger. Das neue Mittel ist besonders zur Behandlung von Unkräutern geeignet, die in Zuckerrohranbaugebieten wachsen.2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine and a non-phytotoxic carrier. The new product is particularly suitable for treating weeds that grow in sugar cane growing areas.
Gegenstand der Erfindung ist weiterhin ein neues Mittel das enthält: einen Thiadiazolylharnstoff der Formel (I)The invention also relates to a new agent which contains: a thiadiazolylurea of the formula (I)
(D(D
NHGH3 NHGH 3
R Trifluormethyl, tert.-Butyl oder Äthylsulfonyl bedeutet,R is trifluoromethyl, tert-butyl or ethylsulfonyl,
zusammen mit Z-Chlor-^äthylamino-e-isopropylamino-i,3t5-triazin. together with Z-chloro- ^ äthylamino-e-isopropylamino-i, 3 t 5-triazine.
709821/0996709821/0996
STST
Die Thiadiazolylharnstoffe der Formel (I) sind bekannte Verbindungen, die z.B. nach dem in der GB-PS 1 266 beschriebenen Verfahren hergestellt werden können. Die Verbindung 2-Chlor-4-äthylamino-6-isopropylamino-1,3»5-triazin ist ebenfalls eine bekannte Verbindung und ist unter dem Generic Name "Atrazine"'bekannt (vergl. Herbicide Handbook of the Weed Science Society of America, 2. Edition, 1970, Seite 86).The thiadiazolylureas of formula (I) are known compounds which, for example, according to the method described in GB-PS 1,266 described method can be produced. The compound 2-chloro-4-ethylamino-6-isopropylamino-1,3 »5-triazine is also a well-known compound and is known by the generic name "Atrazine" '(see Herbicide Handbook of the Weed Science Society of America, 2nd Edition, 1970, p. 86).
Die Verbindung der Formel (i), worin R tert.-Butyl bedeutet, d.h. 1-(5-tert.-Butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylharnstoff, ist die in den erfindungsgemäßen Zubereitungen, Mitteln und bei den erfindungsgemäßen Verfahren bevorzugte Verbindung.The compound of formula (i) in which R is tert-butyl, i.e. 1- (5-tert-butyl-1,3,4-thiadiazol-2-yl) -1,3-dimethylurea, is that in the preparations according to the invention, Agents and compound preferred in the method according to the invention.
Das Verhältnis der Menge an Thiadiazolylharnstoff zu 2-Chlor-4-äthylamino-6-isopropylamino-1,3,5-triazin ist nicht kritisch. Es ist jedoch bevorzugt, die Verbindungen in Verhältnissen im Bereich von etwa 1:10 bis etwa 10:1, mehr bevorzugt von etwa 1:5 bis etwa 5:1 und am meisten bevorzugt von 1:3 bis 3s1» zu vermischen.The ratio of the amount of thiadiazolylurea to 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine is not critical. However, it is preferred to use the compounds in ratios ranging from about 1:10 to about 10: 1, more preferably from about 1: 5 to about 5: 1 and most preferably from 1: 3 to 3½.
Wie oben angegeben, wurde überraschenderweise gefunden, daß die erfindungsgemäßen Mittel besonders für die Kontrolle von Unkräutern auf Äckern und Feldern geeignet sind, wo Zuckerrohr angebaut wird. Der Thiadiazolylharnstoff und das Triazin werden bevorzugt gleichzeitig in Form eines Gemisches angewendet. In einigen Fällen kann auch die aufeinanderfolgende Anwendung der Komponenten des Gemisches bzw. des Mittels durchgeführt werden. " , Solche aufeinanderfolgende Anwendung sollte innerhalb kurzer Zeiten erfolgen.As indicated above, it has surprisingly been found that the agents according to the invention are particularly are suitable for the control of weeds in fields and fields where sugar cane is grown. The thiadiazolylurea and the triazine are preferably used simultaneously in the form of a mixture. In some cases the successive application of the components of the mixture or of the agent can also be carried out. ", Such successive applications should be made within a short period of time.
Unabhängig davon, ob die Anwendung nacheinander oder gleichzeitig erfolgt, werden 0,5 bis 2,5, bevorzugt 0,75 bis 1,5 kg/ha Harnstoff und 0,5 bis 5, bevorzugt 1 bis 2 kg/ha Triazin auf das zu behandelnde Land angewendet.Regardless of whether they are used consecutively or simultaneously, 0.5 to 2.5, preferably 0.75 to 1.5 kg / ha urea and 0.5 to 5, preferably 1 to 2 kg / ha triazine are applied to the land to be treated.
709821/0996709821/0996
Die erfindungsgemäßen Mittel nrtrden üblicherweise in Form herbicider Mittel verwendet, die einen inerten Träger enthalten. Gegenstand der Erfindung sind somit auch herbicide Mittel, die eine Verbindung der Formel (I), wie oben definiert, und Z-Chlor-^äthylamino-ö-isopropylamino-1,3 $5-triazin zusammen mit einem geeigneten inerten Träger für sie enthalten. Gegenstand der Erfindung ist weiterhin ein Verfahren zur Herstellung der oben beschriebenen Mittel durch Vermischen der Komponenten. The agents according to the invention are usually used in the form of herbicidal agents which contain an inert carrier. The invention thus also relates to herbicidal agents which contain a compound of the formula (I) as defined above and Z-chloro- ^ äthylamino-δ-isopropylamino-1,3 $ 5-triazine together with a suitable inert carrier for them . The invention also relates to a process for producing the compositions described above by mixing the components.
Ein erfindungsgemäßes Mittel, das erwähnt werden kann, ist eine wäßrige Suspension, die auf das zu behandelnde Gebiet versprüht werden kann. Eine solches Mittel kann hergestellt werden, indem man die aktiven Bestandteile in einem Sprühtank gerade vor der Verwendung vermischt. Bevorzugt werden jedoch die beiden aktiven Bestandteile in den gewünschten Verhältnissen miteinander formuliert, und diese Formulierung kann vor der Verwendung einfach verdünnt werden. Eine solche wäßrige Formulierung bzw. ein solches wäßriges Mittel wird 0,005 bis 2,5 Gew.%, bevorzugt 0,1 bis 1 Gew.%, Harnstoff und 0,005 bis 5 Gew.%, bevorzugt 0,1 bis 2 Gew.%, Triazin enthalten. J An agent according to the invention that can be mentioned is an aqueous suspension which can be sprayed onto the area to be treated. Such an agent can be made by mixing the active ingredients in a spray tank just prior to use. Preferably, however, the two active ingredients are formulated together in the desired proportions and this formulation can simply be diluted prior to use. Such an aqueous formulation or such an aqueous agent is 0.005 to 2.5% by weight , preferably 0.1 to 1% by weight, urea and 0.005 to 5% by weight, preferably 0.1 to 2% by weight, triazine contain. J
Wie oben angegeben, können die verdünnten erfindungsgemäßen Mittel hergestellt werden, indem man die aktiven Bestandteile gerade vor der Verwendung vermischt oder indem man die fertighergestellte Co-Formulierung aus den beiden aktiven Bestandteilen verdünnt. Im ersteren Fall werden die aktiven Bestandteile üblicherweise in Form eines konzentrierten Mittels bzw. eines Konzentrats vorliegen, das so formuliert ist, daß es für eine schnelle Dispersion in Wasser geeignet ist. Im allgemeinen können irgendwelche geeigneten Konzentrate verwendet werden, und sie werden etwa 1 bis 90 Gev.% der individuellen aktiven Bestandteile enthalten. As indicated above, the diluted compositions of the present invention can be prepared by mixing the active ingredients just prior to use, or by diluting the finished co-formulation from the two active ingredients. In the former case, the active ingredients will usually be in the form of a concentrated agent or concentrate formulated to be suitable for rapid dispersion in water. In general, any suitable concentrates can be used and they will contain from about 1 to 90% by weight of the individual active ingredients.
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-•5·-- • 5 · -
Die aktiven Bestandteile können zusammen als Konzentrate formuliert werden. Diese Konzentrate sind neu und Gegenstand der vorliegenden Erfindung. Diese Konzentrate werden üblicherweise insgesamt 5 bis 90 Gew.% aktive Bestandteile enthalten.The active ingredients can be used together as concentrates be formulated. These concentrates are new and the subject of the present invention. These concentrates will be usually 5 to 90 wt% total active ingredients contain.
Die erfindungsgemäßen Konzentrate enthalten üblicherweise die aktiven Bestandteile in den oben angegebenen Mengen und einen oder mehrere inerte Träger und gegebenenfalls ein oder mehrere oberflächenaktive Mittel, Verdickungsmittel, Antigefriermittel (Gefrierschutzmittel) und Konservierungsmittel. Die Konzentrate können Feststoffe sein, die üblicherweise als benetzbare Pulver oder Zerstäubungsmittel bekannt sind, oder Flüssigkeiten, die als wäßrige Suspensionen vorliegen können.The concentrates according to the invention usually contain the active ingredients in the amounts indicated above and one or more inert carriers and optionally one or more surface-active agents, thickeners, Anti-freezing agents (anti-freeze agents) and preservatives. The concentrates can be solids, commonly known as wettable powders or atomizers are, or liquids, which may be in the form of aqueous suspensions.
Benetzbare Zerstäubungsmittel enthalten ein inniges Gemisch aus aktiven Bestandteilen, einem oder mehreren inerten Trägern und geeigneten oberflächenaktiven Mitteln. Als inerte Träger kann man Attapulgittone, Montmorillonittone, Kieselgur, Kaolin, Glimmer, Talk und gereinigte Silikate verwenden. Wirksame oberflächenaktive Mittel sind z.B. sulfonierte Lignine, Naphthalinsulfonate und kondensierte ilaphthalinsulfonate, Alkylsuccinate, Alkylbenzolsulfonate, Alkylsulfäte und nichtionische oberflächenaktive Mittel, wie Äthylenoxidaddukte von Phenol. Benetzbare Zerstäübungsjnl'ttel, die Gegenstand der vorliegenden Erfindung sind, enthalten typischerweiseWettable atomizers contain an intimate mixture of active ingredients, one or more inert ones Carriers and suitable surfactants. Attapulgite clays, montmorillonite clays, Use kieselguhr, kaolin, mica, talc and purified silicates. Effective surfactants are, for example, sulfonated ones Lignins, naphthalene sulfonates and condensed ilaphthalene sulfonates, alkyl succinates, alkylbenzenesulfonates, Alkyl sulfates and nonionic surfactants, such as ethylene oxide adducts of phenol. Wettable atomizer sleeves, which are the subject of the present invention typically contain
Gew. Weight %%
Thiadiazolylharastoff 10-60Thiadiazolyl resin 10-60
Atrazine 20 - 60 oberflächenaktive(s) Mittel 1-7 Dispersionsmittel 1-7Atrazine 20-60 surfactant 1-7 dispersant 1-7
Anti-Zusammenbackmittel 0-10Anti-caking agents 0-10
inerter Träger bis 100inert carrier up to 100
709821/0996709821/0996
Die Gesamtmenge an aktiven Bestandteilen, d.h. Harnstoff und Atrazine, sollte 90% nicht überschreiten.The total amount of active ingredients, i.e. urea and atrazine, should not exceed 90%.
Wäßrige Suspensionen enthalten die aktiven Bestandteile suspendiert in Wasser zusammen mit irgendwelchen geeigneten oberflächenaktiven Mitteln, Verdickungsmittein, Gefrierschutzmitteln oder Konservierungsmitteln. Geeignete oberflächenaktive Mittel können unter denjenigen ausgewählt werden, die im Zusammenhang mit den benetzbaren Zerstäubungs- ■ mitteln erwähnt wurden. Verdickungsmittel werden üblicherwei- j se, sofern sie verwendet werden, unter geeigneten Cellulose- I materialien und natürlichen Gummis ausgewählt. Wird ein Gefrierschutzmittel verwendet, werden üblicherweise Glykole ! eingesetzt. Sehr viele Materialien können als Konservierungs- j mittel verwendet werden, wie z.B. die verschiedenen Paraben-Antibactericide, Phenol, o-Chlor-cresol, Phenyl-Quecksilber(ll)-nitrat und Formaldehyd. Wäßrige Suspensionen, die Gegenstand der vorliegenden Erfindung sind, enthalten typischerweise:Aqueous suspensions contain the active ingredients suspended in water together with any suitable surfactants, thickeners, antifreeze agents or preservatives. Suitable surfactants can be selected from among those mentioned agents in connection with the wettable atomization ■. Thickeners, if used, are usually selected from suitable cellulosic materials and natural gums. If an anti-freeze agent is used, glycols are usually used! used. A large number of materials can be used as preservatives, such as the various paraben antibactericides, phenol, o-chloro-cresol, phenyl-mercury (II) nitrate and formaldehyde. Aqueous suspensions which are the subject of the present invention typically contain:
Alternativ kann es bevorzugt sein, die neuen erfindungsgemäßen Mittel als granuläre Zubereitungen zu verwenden. Solche Mittel' enthalten typischerweise die aktiven Bestandteile dispergiert in einem granulären inerten Träger, wie grobgemahlenem Ton. Die Teilchengröße der Körnchen wird üblicherweise im Bereich von etwa 0,1 bis etwa 3 mm liegen. Bei den üblichen Verfahren zur Herstellung von Granulatzubereitungen wird die Verbindung in einem billigen Lösungsmittel gelöst und die Lösung auf einen Träger in einerAlternatively, it may be preferred to use the new invention Means to use as granular preparations. Such agents typically include the active ingredients dispersed in a granular inert carrier such as coarse ground clay. The particle size of the Granules will usually range from about 0.1 to about 3 mm. In the usual processes for the production of Granule preparations, the compound is dissolved in a cheap solvent and the solution on a carrier in a
709821/0.9 96709821 / 0.9 96
geeigneten Mischvorrichtung für Feststoffe angewendet. Bei einem anderen, weniger wirtschaftlichen Verfahren werden die Verbindungen in einem Teig dispergiert, der aus feuchtem Ton oder einem anderen inerten Träger besteht, der dann getrocknet und grob unter Herstellung des gewünschten granulären Produktes gemahlen wird.suitable mixing device for solids applied. at Another, less economical, method is to disperse the compounds in a dough made from moist clay or some other inert carrier which is then dried and coarse to produce the desired granular Product is ground.
Die erfindungsgemäßen Co-Zubereitungen können ebenfalls in Form emulgierbarer Konzentrate vorliegen, obgleich diese Art von Zubereitung keine große Bedeutung besitzt.The co-preparations according to the invention can likewise are in the form of emulsifiable concentrates, although this type of preparation is not of great importance.
Die folgenden Beispiele erläutern die Erfindung. In allen Fällen, in denen Harnstoff verwendet wird, ist dies 1-(5-tert.-Butyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylharnstoff. Dieser Harnstoff kann jedoch auch durch seine 5-Trifluormethyl- und 5-Äthylsulfonyl-Analogen ohne nachteilige Wirkung ersetzt werden.The following examples illustrate the invention. In all cases where urea is used, is this is 1- (5-tert-butyl-1,3,4-thiadiazol-2-yl) -1,3-dimethylurea. However, this urea can also be used without detrimental effects due to its 5-trifluoromethyl and 5-ethylsulfonyl analogues Effect to be replaced.
Dieses ist ein Beispiel für ein erfindungsgemäßes benetzbares Zerstäubungsmittel. . This is an example of a wettable atomizing agent according to the invention. .
Gev.%Gev.%
Harnstoff 30Urea 30
Atrazine 45Atrazine 45
Natriumlaurylsulfat 5Sodium Lauryl Sulphate 5
Natriumligninsulfonat 3Sodium lignosulfonate 3
Siliciumdioxid 8Silicon dioxide 8
Porzellanton bis 100Porcelain clay to 100
Die aktiven Bestandteile werden gemahlen und dann mit anderen Bestandteilen in einer an sich bekannten Mischvorrichtung vermischt. Das Gemisch wird dann in einer Fluidenergiemühle auf eine Größe im Bereich von 1 bis 10 Mikron vermählen, und dann wird das Gemisch nochmals vermischt und vor der Verpackung entgast.The active ingredients are ground and then mixed with other ingredients in a mixer known per se mixed. The mixture is then placed in a fluid energy mill ground to a size in the range of 1 to 10 microns and then the mixture is mixed again and degassed before packaging.
709821/0.9 98709821 / 0.9 98
709821 /0.996709821 /0.996
—· Iff —- Iff -
Das Folgende ist ein Beispiel einer wäßrigen erfindungsgemäßen Suspension:The following is an example of an aqueous suspension according to the invention:
Die Größe beider aktiver Bestandteile wird in an sich bekannter Weise, sofern erforderlich, vermindert. Dann werden sie in Wasser, das ein oberflächenaktives System, Konservierungsmittel und einen Teil eines Verdickungsmittels enthält, dispergiert. Die Teilchengröße wird weiter durch Flüssigkeitsvermahlen vermindert, der Rest des Verdickungsmittels wird zugegeben, anschließend wird hydratisiert und dann wird das Produkt mit Wasser verdünnt.The size of both active ingredients is reduced in a manner known per se, if necessary. then they are in water, which has a surfactant system, preservative and part of a thickener contains, dispersed. The particle size is further reduced by liquid milling, the remainder of the thickening agent is added followed by hydration and then the product is diluted with water.
Auf ähnliche Weise werden die folgenden wäßrigen Konzentrate hergestellt.The following aqueous concentrates are prepared in a similar manner.
709821/0.996709821 / 0.996
Harnstoff 5Urea 5
Atrazine 10Atrazine 10
Natriumnaphthalinsulfonat 3Sodium naphthalene sulfonate 3
Natriumligninsulfonat 2Sodium lignosulfonate 2
Äthylenglykol 4Ethylene glycol 4
Phenol 0,5Phenol 0.5
Gummiarabikum 1Gum arabic 1
Wasser bisWater up
Ein benetzbares Pulver aus den folgenden Bestandteilen wird unter Verwendung eines ähnlichen Verfahrens, wie in Beispiel 1 beschrieben, hergestellt.A wettable powder of the following ingredients is prepared using a method similar to that in FIG Example 1 described, produced.
Aus der obigen Beschreibung ist erkennbar, daß die erfindungsgemäßen Konzentrate nach an sich bekannten Verfahren durch Vermischen der aktiven Bestandteile in den gewünschten Anteilen mit einem geeigneten inerten Träger hergestellt werden. Diese Verfahren sind ebenfalls Gegenstand der vorliegenden Erfindung.From the above description it can be seen that the concentrates according to the invention according to methods known per se by mixing the active ingredients in the desired proportions with a suitable inert carrier will. These methods are also the subject of the present invention.
709821/0-996709821 / 0-996
Claims (6)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB45160/75A GB1561636A (en) | 1975-11-07 | 1975-11-07 | Herbicidal combinations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2650362A1 true DE2650362A1 (en) | 1977-05-26 |
Family
ID=10440106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762650362 Withdrawn DE2650362A1 (en) | 1975-11-07 | 1976-11-03 | HERBICIDAL AGENTS AND METHOD FOR ITS MANUFACTURING |
Country Status (32)
| Country | Link |
|---|---|
| JP (1) | JPS5261228A (en) |
| AR (1) | AR218231A1 (en) |
| AT (1) | AT353545B (en) |
| AU (1) | AU506364B2 (en) |
| BE (1) | BE848080A (en) |
| BG (1) | BG27529A3 (en) |
| BR (1) | BR7607372A (en) |
| CA (1) | CA1156851A (en) |
| CH (1) | CH601989A5 (en) |
| CS (1) | CS188295B2 (en) |
| DD (1) | DD127723A5 (en) |
| DE (1) | DE2650362A1 (en) |
| DK (1) | DK498876A (en) |
| EG (1) | EG12382A (en) |
| ES (1) | ES453080A1 (en) |
| FR (1) | FR2330320A1 (en) |
| GB (1) | GB1561636A (en) |
| GR (1) | GR61714B (en) |
| HU (1) | HU176128B (en) |
| IE (1) | IE44547B1 (en) |
| IL (1) | IL50818A (en) |
| IT (1) | IT1080520B (en) |
| MX (1) | MX4486E (en) |
| NL (1) | NL7612126A (en) |
| NZ (1) | NZ182485A (en) |
| OA (1) | OA05472A (en) |
| PL (1) | PL101274B1 (en) |
| PT (1) | PT65792B (en) |
| RO (1) | RO70593A (en) |
| SE (1) | SE7612198L (en) |
| SU (1) | SU694046A3 (en) |
| ZA (1) | ZA766626B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2741394A1 (en) * | 1977-08-29 | 1979-03-22 | Lilly Co Eli | Synergistic herbicidal compsns. - comprise inert carrier, aromatic amine and substd. nitrogen-sulphur heterocycle |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5995208A (en) * | 1982-11-25 | 1984-06-01 | Japan Carlit Co Ltd:The | Herbicide composition |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1816696A1 (en) * | 1967-12-27 | 1969-08-21 | Agripat Sa | New 1,3,4-thiadiazolyl ureas and processes for their preparation |
| DE1816568A1 (en) * | 1968-12-23 | 1970-11-05 | Bayer Ag | 1,3,4-Thiadiazoly (5) ureas, their use as herbicides and process for their preparation |
| CH513585A (en) * | 1969-07-18 | 1971-10-15 | Agripat Sa | Thiadiazolyl (2)- ureas prodn |
| DE2118520A1 (en) * | 1970-04-17 | 1971-10-28 | GuIf Research & Development Co., Pittsburgh, Pa. (V.StA.) | Herbicides |
| DE2028778A1 (en) * | 1970-06-06 | 1971-12-23 | Thiadiazolyl-urea herbicides - 5 - substd by sulphinyl or sulphonyl | |
| GB1266172A (en) * | 1968-03-13 | 1972-03-08 | ||
| DE2044442A1 (en) * | 1970-09-03 | 1972-03-09 | Schering Ag | 5-alkylsulphinyl or sulphonyl - 1,3,4-thiadiazolyl-ureas - as herbicides |
| GB1276925A (en) * | 1968-05-22 | 1972-06-07 | Bayer Ag | 0,3,4-thiadiazolyl ureas |
| DE2402421A1 (en) * | 1973-01-19 | 1974-07-25 | Ciba Geigy Ag | LIQUID HERBICIDAL PREPARATIONS AND METHODS OF DESTRUCTION OF DISAPPOINTING OR HARMFUL PLANTS |
| JPS49124230A (en) * | 1972-08-14 | 1974-11-28 |
-
1975
- 1975-11-07 GB GB45160/75A patent/GB1561636A/en not_active Expired
-
1976
- 1976-10-25 CA CA000264102A patent/CA1156851A/en not_active Expired
- 1976-10-29 IT IT51972/76A patent/IT1080520B/en active
- 1976-11-01 NZ NZ182485A patent/NZ182485A/en unknown
- 1976-11-01 RO RO7688275A patent/RO70593A/en unknown
- 1976-11-02 AR AR265311A patent/AR218231A1/en active
- 1976-11-02 NL NL7612126A patent/NL7612126A/en not_active Application Discontinuation
- 1976-11-02 GR GR52065A patent/GR61714B/en unknown
- 1976-11-02 IL IL50818A patent/IL50818A/en unknown
- 1976-11-02 DD DD7600195559A patent/DD127723A5/en unknown
- 1976-11-02 CH CH1377376A patent/CH601989A5/xx not_active IP Right Cessation
- 1976-11-02 SE SE7612198A patent/SE7612198L/en unknown
- 1976-11-03 DE DE19762650362 patent/DE2650362A1/en not_active Withdrawn
- 1976-11-03 IE IE2446/76A patent/IE44547B1/en unknown
- 1976-11-03 PT PT65792A patent/PT65792B/en unknown
- 1976-11-04 BR BR7607372A patent/BR7607372A/en unknown
- 1976-11-04 FR FR7633228A patent/FR2330320A1/en active Granted
- 1976-11-04 SU SU762416205A patent/SU694046A3/en active
- 1976-11-04 DK DK498876A patent/DK498876A/en unknown
- 1976-11-04 ZA ZA766626A patent/ZA766626B/en unknown
- 1976-11-04 HU HU76LI301A patent/HU176128B/en unknown
- 1976-11-04 MX MX765049U patent/MX4486E/en unknown
- 1976-11-04 CS CS767122A patent/CS188295B2/en unknown
- 1976-11-05 BG BG7634618A patent/BG27529A3/en unknown
- 1976-11-05 BE BE6045751A patent/BE848080A/en not_active IP Right Cessation
- 1976-11-05 JP JP51133120A patent/JPS5261228A/en active Pending
- 1976-11-05 OA OA55973A patent/OA05472A/en unknown
- 1976-11-05 AT AT823576A patent/AT353545B/en not_active IP Right Cessation
- 1976-11-05 AU AU19365/76A patent/AU506364B2/en not_active Expired
- 1976-11-05 ES ES453080A patent/ES453080A1/en not_active Expired
- 1976-11-05 PL PL1976193491A patent/PL101274B1/en unknown
- 1976-11-06 EG EG684/76A patent/EG12382A/en active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE1816696A1 (en) * | 1967-12-27 | 1969-08-21 | Agripat Sa | New 1,3,4-thiadiazolyl ureas and processes for their preparation |
| AT291670B (en) * | 1967-12-27 | 1971-07-26 | Agripat Sa | Herbicidal agent |
| GB1266172A (en) * | 1968-03-13 | 1972-03-08 | ||
| GB1276925A (en) * | 1968-05-22 | 1972-06-07 | Bayer Ag | 0,3,4-thiadiazolyl ureas |
| DE1816568A1 (en) * | 1968-12-23 | 1970-11-05 | Bayer Ag | 1,3,4-Thiadiazoly (5) ureas, their use as herbicides and process for their preparation |
| CH513585A (en) * | 1969-07-18 | 1971-10-15 | Agripat Sa | Thiadiazolyl (2)- ureas prodn |
| DE2118520A1 (en) * | 1970-04-17 | 1971-10-28 | GuIf Research & Development Co., Pittsburgh, Pa. (V.StA.) | Herbicides |
| DE2028778A1 (en) * | 1970-06-06 | 1971-12-23 | Thiadiazolyl-urea herbicides - 5 - substd by sulphinyl or sulphonyl | |
| DE2044442A1 (en) * | 1970-09-03 | 1972-03-09 | Schering Ag | 5-alkylsulphinyl or sulphonyl - 1,3,4-thiadiazolyl-ureas - as herbicides |
| JPS49124230A (en) * | 1972-08-14 | 1974-11-28 | ||
| JPS49124231A (en) * | 1972-08-14 | 1974-11-28 | ||
| DE2402421A1 (en) * | 1973-01-19 | 1974-07-25 | Ciba Geigy Ag | LIQUID HERBICIDAL PREPARATIONS AND METHODS OF DESTRUCTION OF DISAPPOINTING OR HARMFUL PLANTS |
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| Title |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2741394A1 (en) * | 1977-08-29 | 1979-03-22 | Lilly Co Eli | Synergistic herbicidal compsns. - comprise inert carrier, aromatic amine and substd. nitrogen-sulphur heterocycle |
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