CH532891A - Selective herbicides - contg 1-(substd phenyl) -3-methyl-3-methoxyureas - Google Patents
Selective herbicides - contg 1-(substd phenyl) -3-methyl-3-methoxyureasInfo
- Publication number
- CH532891A CH532891A CH457469A CH457469A CH532891A CH 532891 A CH532891 A CH 532891A CH 457469 A CH457469 A CH 457469A CH 457469 A CH457469 A CH 457469A CH 532891 A CH532891 A CH 532891A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- alkyl
- formula
- aryl
- phenyl
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title description 3
- 241000196324 Embryophyta Species 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 235000013339 cereals Nutrition 0.000 claims abstract description 5
- 240000008042 Zea mays Species 0.000 claims abstract description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 235000009973 maize Nutrition 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 244000045561 useful plants Species 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000004171 alkoxy aryl group Chemical group 0.000 abstract 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 abstract 1
- 235000005822 corn Nutrition 0.000 abstract 1
- 244000038559 crop plants Species 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- -1 substituted cycloalkyl radical Chemical class 0.000 description 22
- 239000004480 active ingredient Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000003254 radicals Chemical class 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- BUIQXUQLYZPMLS-UHFFFAOYSA-N 1-ethoxy-2-isocyanatobenzene Chemical compound CCOC1=CC=CC=C1N=C=O BUIQXUQLYZPMLS-UHFFFAOYSA-N 0.000 description 1
- AJBZENLMTKDAEK-UHFFFAOYSA-N 3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-4,9-diol Chemical compound CC12CCC(O)C(C)(C)C1CCC(C1(C)CC3O)(C)C2CCC1C1C3(C)CCC1C(=C)C AJBZENLMTKDAEK-UHFFFAOYSA-N 0.000 description 1
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical class [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003880 Calendula Nutrition 0.000 description 1
- 240000001432 Calendula officinalis Species 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- 240000002635 Dendrocalamus asper Species 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 235000021506 Ipomoea Nutrition 0.000 description 1
- 241000207783 Ipomoea Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241000209149 Zea Species 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- GCPXMJHSNVMWNM-UHFFFAOYSA-N arsenous acid Chemical class O[As](O)O GCPXMJHSNVMWNM-UHFFFAOYSA-N 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Cpds. of formula (I) (where X is H or halogen, Y is S or O; R is alkoxyalkyl, alkylthioalkyl, aryloxyalkyl, alkoxyaryl, alkylthioaryl, arylkyl (all alkyl residues contg. 1-4C) aryl or opt. substd. 3-8C cycloalkyl) are used for the selective control of weeds in cultures of crop plants, esp. cereals and corn. The prefd. cpds. are (I) where X is C and RY is MeOCH2O or EtOC2H4O.
Description
Verwendung von Phenylharnstoffen zum selektiven Bekämpfen von Unkräutern in Kulturen von Nutzpflanzen Die vorliegende Erfindung betrifft die Verwendung von Verbindungen der Formel
EMI1.1
worin
X ein Wasserstoff- oder Halogenatom,
Y ein Sauerstoff- oder Schwefelatom und
R einen C1-C4-AIkoxy-C1-C4-alkyl-, C1-C4-Alkylthio- C1-C4-alkyl-, Aryloxy-C1-C4-alkyl-, C1-C4-Alkoxyaryl-, C1-C4-Alkylthio-aryl-, Aryl-C1-C4-alkyl-, Aryl- oder gegebenenfalls substituierten Cycloalkylrest mit 38 Ring-C-Atomen bedeuten, zum selektiven Bekämpfen von Unkräutern in Kulturen von Nutzpflanzen, insbesondere Kulturen von Getreide und Mais.
Das in den Bedeutungen der Verbindungen der Formel I für X in Betracht kommende Halogenatom kann Fluor, Chlor, Brom oder Jod sein, besonders bevorzugt sind jedoch Chlor und Brom. Unter C1-C4-Alkyl- bzw. C1-C4-Alkoxy- und C1-C4-Alkylthioresten im Rest R sind Reste zu verstehen, die bis zu 4, vorzugsweise 1 oder 2, Kohlenstoffatome enthalten und gerad- oder verzweigtkettig sein können, wie z. B.
Methyl-, Äthyl-, Propyl-, Isopropyl-, Butyl-, Isobutyl-, sek. Butyl-, tert.-Butyl-. Definitionsgemässe Aryl- bzw. Aryloxyoder Arylthioreste können ein- oder mehrkernig sein, sind jedoch vorzugsweise einkernig. Beispiele solcher Kerne sind u. a. der Naphthyl- und insbesondere der Phenylrest, die beide ihrerseits wiederum Substituenten, wie z. B. C1-C4 Alkyl- oder C1-C4-Alkoxyreste oder Halogenatome, wie F, Cl, Br oder J, tragen können, vorzugsweise jedoch unsubstituiert sind. Erfindungsgemäss geeignete Aryl-C1-C4-alkylreste enthalten in der Alkylkette, die verzweigt oder unverzweigt sein kann, bis zu 4, vorzugsweise 1 bis 2, Kohlenstoffatome. Für den Arylteil dieser Aralkylreste gelten die gleichen Aussagen, wie sie oben für die Arylreste gemacht wurden.
Die Cycloalkylreste weisen 3 bis 8 Ringkohlenstoffatome auf und können durch C-C4-Alkylreste substituiert sein.
Beispiele solcher Cycloalkylreste sind das Cyclopropan, Cyclobutan, Cyclopentan, Cycloheptan, Cyclooctan, insbesondere jedoch Cyclohexan.
Beispiele von Verbindungen der Formel (I), die erfindungsgemäss geeignet sind, sind in der folgenden Tabelle aufgeführt:
EMI1.2
EMI2.1
<tb> <SEP> R <SEP> Y <SEP> X
<tb> CH3-CHrO-CHr <SEP> O <SEP> C1
<tb> iso-C3H7-O-CHr <SEP> O <SEP> C1
<tb> CH3-O-C(CH3)° <SEP> 0 <SEP> C1
<tb> CH3-O-CH-CH=CHr <SEP> O <SEP> C1
<tb> <SEP> CH3
<tb> CHrO-CHC(CH3)r <SEP> 0 <SEP> C1
<tb> Phenyl- <SEP> O <SEP> C1
<tb> Cyclohexyl- <SEP> O <SEP> C1
<tb> Phenyl-O-CHw <SEP> O <SEP> C1
<tb> C2H5-O-Phenyl- <SEP> O <SEP> C1
<tb> CH3-O-CHr <SEP> O <SEP> Br
<tb> iso-C4HrO-CHr <SEP> O <SEP> Br
<tb> iso-C3H7-O-C(CH3)r <SEP> 0 <SEP> Br
<tb> Phenyl- <SEP> O <SEP> Br
<tb> Phenyl-O-CHr <SEP> O <SEP> Br
<tb> Benzyl- <SEP> O <SEP> Br
<tb> Cyclohexyl- <SEP> O <SEP> Br
<tb> Phenyl <SEP> S <SEP> C1
<tb> Benzyl <SEP> S <SEP> C1
<tb> Cyclohexyl <SEP> S <SEP> C1
<tb> p-Tolyl- <SEP> O <SEP> C1
<tb> p-Anisyl- <SEP> 0
<SEP> C1
<tb> o-Tolyl- <SEP> O <SEP> C1
<tb> Phenyl- <SEP> S <SEP> F
<tb> Phenyl- <SEP> O <SEP> F
<tb> Phenyl- <SEP> O <SEP> H
<tb> Phenyl-O-CHr <SEP> O <SEP> H
<tb>
Die Herstellung dieser Verbindungen kann nach an sich bekannten Methoden erfolgen, z. B. durch Reaktion einer Verbindung der Formel
EMI2.2
mit einer Verbindung der Formel
EMI2.3
worin R, X und Y die angegebene Bedeutung haben und A und B Reste bedeuten, die unter Anlagerung oder Kondensation Harnstoffe bilden. Dabei stellt eine der beiden Gruppen A und B ein Amin dar, während die andere ein Urethan, ein Carbamoylhalogenid, eine Harnstoffgruppe oder insbesondere den Isocyanat- oder Isothiocyanatrest darstellt. Im letzteren Fall muss zum Austausch des S-Atoms gegen Sauerstoff eine Nachbehandlung mit einem Oxydationsmittel, z. B.
HgO, Cl2/H20 oder COC12/H20 vorgenommen werden.
R1 steht für eine Methylgruppe oder ein Wasserstoffatom. Im letzteren Falle, wenn also z. B. von Hydroxylamin ausgegangen wird, muss nach der Harnstoffbildung eine Nachmethylierung, z. B. mit Dimethylsulfat, folgen.
Die Verbindungen der Formel (I) weisen ausgesprochen selektivherbizide Eigenschaften im allgemeinen auf und erweisen sich als besonders vorteilhaft beim Bekämpfen von Unkräutern in Getreide- und Maiskulturen. Als Getreide werden hier Weizen, Gerste und Roggen angesprochen. Dabei erweisen sich Verbindungen, die in der R-Y-Gruppe höchstens ein Schwefelatom aufweisen, als besonders geeignet. Sie entsprechen vorzugsweise der Formel
EMI2.4
worin R2 für einen Nieder-alkoxy-nieder-alkyl- oder Niederalkylthio-nieder-alkylrest steht. Die hier als niedere Alkoxybzw. Alkylthio- und Alkylreste in Betracht kommenden Gruppen weisen 1 bis 4, insbesondere 1 bis 2, Kohlenstoffatome auf und können verzweigt oder unverzweigt sein. Von besonderem Vorteil ist die Wirkung gegen grasartige Unkräuter, wie insbesondere Alopecurus und Avena fatua.
Bei genügend grosser Aufwandmenge ist jedoch auch totalherbizide Wirkung vorhanden. Die Anwendung der Wirkstoffe kann sowohl im Vorauflauf- wie im Nachauflaufverfahren erfolgen. Dabei können die Aufwandmengen in weiten Grenzen schwanken, z. B. zwischen 0,1 und 10 kg Wirkstoff pro Hektare, vorzugsweise werden jedoch 0,5 bis 5 kg Wirkstoff pro Hektare eingesetzt.
Die erfindungsgemäss verwendbaren Mittel enthalten im allgemeinen ausser den Wirkstoffen der Formel I einen geeigneten Träger und/oder andere Zuschlagstoffe. Geeignete Träger und Zuschlagstoffe können fest oder flüssig sein und entsprechen den in der Formulierungstechnik üblichen Stoffen, wie z. B. natürlichen oder regenerierten mineralischen Stoffen, Lösungs-, Verdünnungs-, Dispergier-, Emulgier-, Netz-, Haft-, Verdickungs-, Binde- oder Düngemitteln. Ferner können noch weitere Herbizide zugesetzt werden. Solche Herbizide können z. B. der Klasse der Harnstoffe, der gesättigten oder ungesättigten Halogenfettsäuren, Halogenb enzo- nitrile, Halogenbenzoesäuren, Phenoxyalkylcarbonsäuren, Carbamate, Triazine, Nitroalkylphenole, quaternären Ammoniumsalze, Sulfaminsäure, Arsenate, Arsenite, Borate oder Chlorate angehören.
Zur Verwendung in Schädlingsbekämpfungsmitteln können die Verbindungen der Formel I als Stäubemittel, Emulsionskonzentrate, als Granulate, Dispersionen oder auch als Sprays, wie etwa bei der Gasphasenapplikation in Gewächshäusern, als Lösungen oder Aufschlämmungen in üblicher Formulierung, die zum Allgemeinwissen der Applikationstechnik gehört, verarbeitet werden. Man vergleiche entsprechende Angaben im Schweizer Patent Nur.424359.
Einige Beispiele werden weiter unten gegeben.
Beispiel 1
Man lässt bei Raumtemperatur und unter kräftigem Rühren eine Lösung von 48,3 g 3-Chlor-4-68-äthoxy)-äthoxy- phenylisocyanat in 50 ml trockenem Acetonitril zu einer Lösung von 30 ml 30%igem N-Methyl-N-methoxyamin in 200 ml Wasser zutropfen. Nach beendeter Zugabe wird etwa 4 Stunden lang weitergerührt, worauf der auskristallisierte N-[3-Chlor-4-6B-äthoxy)-äthoxyphenyl]-N'-methyl-N'- methoxyharnstoff der Formel
EMI3.1
(Verbindung 1) abgesaugt wird. Ausbeute 95 %. Nach Umkristallisieren aus einem Benzol/Benzin-Gemisch liegt der Smp. bei 94-95" C.
Analog werden die folgenden Verbindungen erhalten:
EMI3.2
Verb. R Y X Smp. in C
2 CH30CH2- O C1 82-82,5
3 CH30C2H4- O C1 79-80
4 n-C4HsOC2H4- O C1 Öl
5 CH3SCH2- O C1 96-97
6 CH3SC2H4- O C1 62-63
7 C2H5SC2H4- O C1 78-80
8 CGH5-CH;r O Cl 103-104
9 C6H5 O C1 67-68
Formulierungs-B eispiele Stäubemittel
Gleiche Teile eines erfindungsgemässen Wirkstoffes und gefällte Kieselsäure werden fein vermahlen. Durch Vermischen mit Kaolin oder Talkum können daraus Stäubemittel mit bevorzugt 1-6% Wirkstoffgehalt hergestellt werden.
Spritzpulver
Zur Herstellung eines Spritzpulvers werden beispielsweise die folgenden Komponenten gemischt und fein vermahlen:
50 Teile Wirkstoff gemäss vorliegender Erfindung,
20 Teile Hisil (hoch adsorptive Kieselsäure),
25 Teile Bolus alba (Kaolin),
3,5 Teile Reaktionsprodukt aus p-tert.-Octylphenol und Äthylenoxyd
1,5 Teile (1-benzyl-2-stearyl-benzimidazol-6,3' -disulfo- saures Natrium).
Emulsionskonzentrat
Gut lösliche Wirkstoffe können auch als Emulsionskonzentrat nach folgender Vorschrift formuliert werden:
20 Teile Wirkstoff,
70 Teile Xylol,
10 Teile einer Mischung aus einem Reaktionsprodukt eines Alkylphenols mit Äthylenoxyd und Calcium dodecylbenzolsulfonat werden gemischt. Beim Verdünnen mit Wasser auf die gewünschte Konzentration entsteht eine spritzfähige Emulsion.
Beispiel 2
Im Gewächshaus wurden in Tontöpfen die in der unten folgenden Tabelle aufgeführten Pflanzen ausgesät. Die Prüfung erfolgte mit der Verbindung I im Postemergent-Verfahren 12 Tage nach der Aussaat. Die Auswertung wurde
18 Tage nach der Applikation vorgenommen.
2 kg Wirkstoff Pflanze pro Hektare Hordeum 2 Zea 1 Digitaria 7 Sorghum 7 Calendula 9 Chrysanthemum 9 Brassica 9 Ipomoea 9 Stellaria 7 Amaranthus 9
Legende: 1 = keine Schäden
3 = gerade noch tolerierbare Schäden
9 = Totalschaden
Use of phenylureas for the selective control of weeds in crops of useful plants The present invention relates to the use of compounds of the formula
EMI1.1
wherein
X is a hydrogen or halogen atom,
Y is an oxygen or sulfur atom and
R is a C1-C4-alkoxy-C1-C4-alkyl-, C1-C4-alkylthio- C1-C4-alkyl-, aryloxy-C1-C4-alkyl-, C1-C4-alkoxyaryl-, C1-C4-alkylthio- aryl, aryl-C1-C4-alkyl, aryl or optionally substituted cycloalkyl radical with 38 ring carbon atoms mean for the selective control of weeds in crops of useful plants, in particular crops of cereals and maize.
The halogen atom which comes into consideration for X in the meanings of the compounds of the formula I can be fluorine, chlorine, bromine or iodine, but chlorine and bromine are particularly preferred. C1-C4-alkyl or C1-C4-alkoxy and C1-C4-alkylthio radicals in the radical R are to be understood as meaning radicals which contain up to 4, preferably 1 or 2, carbon atoms and can be straight or branched-chain, such as z. B.
Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec. Butyl, tert-butyl. Aryl or aryloxy or arylthio radicals according to the definition can be mononuclear or polynuclear, but are preferably mononuclear. Examples of such cores are u. a. the naphthyl and especially the phenyl radical, both of which in turn have substituents, such as. B. C1-C4 alkyl or C1-C4-alkoxy radicals or halogen atoms such as F, Cl, Br or J, can carry, but are preferably unsubstituted. Aryl-C1-C4-alkyl radicals suitable according to the invention contain up to 4, preferably 1 to 2, carbon atoms in the alkyl chain, which can be branched or unbranched. The same statements apply to the aryl part of these aralkyl radicals as were made above for the aryl radicals.
The cycloalkyl radicals have 3 to 8 ring carbon atoms and can be substituted by C -C -alkyl radicals.
Examples of such cycloalkyl radicals are cyclopropane, cyclobutane, cyclopentane, cycloheptane, cyclooctane, but in particular cyclohexane.
Examples of compounds of the formula (I) which are suitable according to the invention are listed in the following table:
EMI1.2
EMI2.1
<tb> <SEP> R <SEP> Y <SEP> X
<tb> CH3-CHrO-CHr <SEP> O <SEP> C1
<tb> iso-C3H7-O-CHr <SEP> O <SEP> C1
<tb> CH3-O-C (CH3) ° <SEP> 0 <SEP> C1
<tb> CH3-O-CH-CH = CHr <SEP> O <SEP> C1
<tb> <SEP> CH3
<tb> CHrO-CHC (CH3) r <SEP> 0 <SEP> C1
<tb> Phenyl- <SEP> O <SEP> C1
<tb> Cyclohexyl- <SEP> O <SEP> C1
<tb> Phenyl-O-CHw <SEP> O <SEP> C1
<tb> C2H5-O-Phenyl- <SEP> O <SEP> C1
<tb> CH3-O-CHr <SEP> O <SEP> Br
<tb> iso-C4HrO-CHr <SEP> O <SEP> Br
<tb> iso-C3H7-O-C (CH3) r <SEP> 0 <SEP> Br
<tb> Phenyl- <SEP> O <SEP> Br
<tb> Phenyl-O-CHr <SEP> O <SEP> Br
<tb> Benzyl- <SEP> O <SEP> Br
<tb> Cyclohexyl- <SEP> O <SEP> Br
<tb> Phenyl <SEP> S <SEP> C1
<tb> Benzyl <SEP> S <SEP> C1
<tb> Cyclohexyl <SEP> S <SEP> C1
<tb> p-Tolyl- <SEP> O <SEP> C1
<tb> p-anisyl- <SEP> 0
<SEP> C1
<tb> o-Tolyl- <SEP> O <SEP> C1
<tb> Phenyl- <SEP> S <SEP> F
<tb> Phenyl- <SEP> O <SEP> F
<tb> Phenyl- <SEP> O <SEP> H
<tb> Phenyl-O-CHr <SEP> O <SEP> H
<tb>
These compounds can be prepared by methods known per se, e.g. B. by reaction of a compound of the formula
EMI2.2
with a compound of the formula
EMI2.3
where R, X and Y have the meanings given and A and B are radicals which form ureas with addition or condensation. One of the two groups A and B represents an amine, while the other represents a urethane, a carbamoyl halide, a urea group or, in particular, the isocyanate or isothiocyanate radical. In the latter case, an aftertreatment with an oxidizing agent, e.g. B.
HgO, Cl2 / H20 or COC12 / H20 can be made.
R1 stands for a methyl group or a hydrogen atom. In the latter case, so if z. B. is assumed from hydroxylamine, must after the urea formation, a Nachmethylierung, z. B. with dimethyl sulfate, follow.
The compounds of the formula (I) generally have markedly selective herbicidal properties and are found to be particularly advantageous in the control of weeds in cereal and maize crops. Wheat, barley and rye are referred to as grain here. Compounds which have at most one sulfur atom in the R-Y group prove to be particularly suitable. They preferably correspond to the formula
EMI2.4
where R2 is a lower-alkoxy-lower-alkyl or lower-alkylthio-lower-alkyl radical. The here as lower Alkoxybzw. Groups suitable for alkylthio and alkyl radicals have 1 to 4, in particular 1 to 2, carbon atoms and can be branched or unbranched. The action against grass-like weeds, such as in particular Alopecurus and Avena fatua, is of particular advantage.
With a sufficiently large application rate, however, there is also a total herbicidal effect. The active ingredients can be used both pre-emergence and post-emergence. The application rates can vary within wide limits, e.g. B. between 0.1 and 10 kg of active ingredient per hectare, but preferably 0.5 to 5 kg of active ingredient per hectare are used.
In addition to the active ingredients of the formula I, the agents which can be used according to the invention generally contain a suitable carrier and / or other additives. Suitable carriers and additives can be solid or liquid and correspond to the substances customary in formulation technology, such as. B. natural or regenerated mineral substances, solvents, thinners, dispersants, emulsifiers, wetting agents, adhesives, thickeners, binders or fertilizers. Further herbicides can also be added. Such herbicides can e.g. B. belong to the class of ureas, saturated or unsaturated halogenated fatty acids, halobenzonitriles, halobenzoic acids, phenoxyalkylcarboxylic acids, carbamates, triazines, nitroalkylphenols, quaternary ammonium salts, sulfamic acid, arsenates, arsenites, borates or chlorates.
For use in pesticides, the compounds of the formula I can be processed as dusts, emulsion concentrates, as granules, dispersions or also as sprays, such as in gas phase application in greenhouses, as solutions or slurries in the usual formulation, which is part of general knowledge of application technology. Compare the corresponding information in the Swiss patent Nur.424359.
Some examples are given below.
example 1
A solution of 48.3 g of 3-chloro-4-68-ethoxy) ethoxyphenyl isocyanate in 50 ml of dry acetonitrile is allowed to form a solution of 30 ml of 30% strength N-methyl-N-methoxyamine at room temperature and with vigorous stirring add dropwise in 200 ml of water. After the addition is complete, stirring is continued for about 4 hours, whereupon the crystallized N- [3-chloro-4-6B-ethoxy) ethoxyphenyl] -N'-methyl-N'-methoxyurea of the formula
EMI3.1
(Connection 1) is sucked off. Yield 95%. After recrystallization from a benzene / gasoline mixture, the melting point is 94-95 ° C.
The following compounds are obtained analogously:
EMI3.2
Verb. R Y X m.p. in C
2 CH30CH2- O C1 82-82.5
3 CH30C2H4- O C1 79-80
4 n-C4HsOC2H4- O C1 oil
5 CH3SCH2- O C1 96-97
6 CH3SC2H4- O C1 62-63
7 C2H5SC2H4- O C1 78-80
8 CGH5-CH; r O Cl 103-104
9 C6H5 O C1 67-68
Formulation examples Dusts
Equal parts of an active ingredient according to the invention and precipitated silica are finely ground. By mixing it with kaolin or talc, it can be used to produce dusts with preferably 1-6% active ingredient content.
Wettable powder
To produce a wettable powder, for example, the following components are mixed and finely ground:
50 parts of active ingredient according to the present invention,
20 parts of Hisil (highly adsorptive silica),
25 parts Bolus alba (kaolin),
3.5 parts of reaction product from p-tert-octylphenol and ethylene oxide
1.5 parts (1-benzyl-2-stearyl-benzimidazole-6,3'-disulfonic acid sodium).
Emulsion concentrate
Easily soluble active ingredients can also be formulated as an emulsion concentrate according to the following instructions:
20 parts active ingredient,
70 parts xylene,
10 parts of a mixture of a reaction product of an alkylphenol with ethylene oxide and calcium dodecylbenzenesulfonate are mixed. When diluting with water to the desired concentration, a sprayable emulsion is created.
Example 2
The plants listed in the table below were sown in clay pots in the greenhouse. The test was carried out with compound I in the post-emergent method 12 days after sowing. The evaluation was made
Made 18 days after application.
2 kg of active ingredient plant per hectare Hordeum 2 Zea 1 Digitaria 7 Sorghum 7 Calendula 9 Chrysanthemum 9 Brassica 9 Ipomoea 9 Stellaria 7 Amaranthus 9
Legend: 1 = no damage
3 = damage that is barely tolerable
9 = total loss
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH457469A CH532891A (en) | 1969-03-26 | 1969-03-26 | Selective herbicides - contg 1-(substd phenyl) -3-methyl-3-methoxyureas |
| ES366190A ES366190A1 (en) | 1968-04-19 | 1969-04-18 | Procedure for the preparation of phenilureas. (Machine-translation by Google Translate, not legally binding) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH457469A CH532891A (en) | 1969-03-26 | 1969-03-26 | Selective herbicides - contg 1-(substd phenyl) -3-methyl-3-methoxyureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH532891A true CH532891A (en) | 1973-01-31 |
Family
ID=4278622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH457469A CH532891A (en) | 1968-04-19 | 1969-03-26 | Selective herbicides - contg 1-(substd phenyl) -3-methyl-3-methoxyureas |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH532891A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4090865A (en) * | 1975-07-23 | 1978-05-23 | Stauffer Chemical Company | Diphenyl ether amides |
| US4129436A (en) | 1977-03-03 | 1978-12-12 | Sumitomo Chemical Company, Limited | N'-[4-(substituted phenethyloxy)phenyl]-N-methyl-N-methoxyurea |
| US4144049A (en) | 1976-03-16 | 1979-03-13 | Sumitomo Chemical Company, Limited | N-(4-Benzyloxyphenyl)-N-methyl-N-methoxyurea |
| US4249938A (en) * | 1977-06-28 | 1981-02-10 | Sumitomo Chemical Company, Limited | N-Phenyl-N-methyl-urea derivatives, and their production and use |
| US4294986A (en) * | 1979-06-25 | 1981-10-13 | American Cyanamid Co. | Novel para-phenylalkoxy phenylurea and thiourea compounds and herbicidal use thereof |
| US4336062A (en) * | 1977-09-19 | 1982-06-22 | Stauffer Chemical Company | Herbicidal cyclohexenone derivatives |
| US4358309A (en) * | 1980-04-17 | 1982-11-09 | Chugai Seiyaku Kabushiki Kaisha | Urea derivatives and highly selective herbicidal compositions containing the same |
| US4690709A (en) * | 1977-10-26 | 1987-09-01 | Sumitomo Chemical Company, Limited | Urea derivatives, and their use as herbicides |
-
1969
- 1969-03-26 CH CH457469A patent/CH532891A/en not_active IP Right Cessation
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4090865A (en) * | 1975-07-23 | 1978-05-23 | Stauffer Chemical Company | Diphenyl ether amides |
| US4144049A (en) | 1976-03-16 | 1979-03-13 | Sumitomo Chemical Company, Limited | N-(4-Benzyloxyphenyl)-N-methyl-N-methoxyurea |
| US4129436A (en) | 1977-03-03 | 1978-12-12 | Sumitomo Chemical Company, Limited | N'-[4-(substituted phenethyloxy)phenyl]-N-methyl-N-methoxyurea |
| US4249938A (en) * | 1977-06-28 | 1981-02-10 | Sumitomo Chemical Company, Limited | N-Phenyl-N-methyl-urea derivatives, and their production and use |
| US4336062A (en) * | 1977-09-19 | 1982-06-22 | Stauffer Chemical Company | Herbicidal cyclohexenone derivatives |
| US4690709A (en) * | 1977-10-26 | 1987-09-01 | Sumitomo Chemical Company, Limited | Urea derivatives, and their use as herbicides |
| US4294986A (en) * | 1979-06-25 | 1981-10-13 | American Cyanamid Co. | Novel para-phenylalkoxy phenylurea and thiourea compounds and herbicidal use thereof |
| US4358309A (en) * | 1980-04-17 | 1982-11-09 | Chugai Seiyaku Kabushiki Kaisha | Urea derivatives and highly selective herbicidal compositions containing the same |
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| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |