[go: up one dir, main page]

WO2001043546A2 - Combinaisons d'alkylazines herbicides et de phytoprotecteurs - Google Patents

Combinaisons d'alkylazines herbicides et de phytoprotecteurs Download PDF

Info

Publication number
WO2001043546A2
WO2001043546A2 PCT/EP2000/011862 EP0011862W WO0143546A2 WO 2001043546 A2 WO2001043546 A2 WO 2001043546A2 EP 0011862 W EP0011862 W EP 0011862W WO 0143546 A2 WO0143546 A2 WO 0143546A2
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
group
substituted
radicals
compounds
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.)
Ceased
Application number
PCT/EP2000/011862
Other languages
German (de)
English (en)
Other versions
WO2001043546A3 (fr
Inventor
Christopher Rosinger
Hartmut Ahrens
Thomas Auler
Hermann Bieringer
Wolfgang Giencke
Jens Hollander
Erwin Hacker
Klemens Minn
Lothar Willms
Jürgen Zindel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Aventis CropScience GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Aventis CropScience GmbH filed Critical Aventis CropScience GmbH
Priority to AU23601/01A priority Critical patent/AU2360101A/en
Publication of WO2001043546A2 publication Critical patent/WO2001043546A2/fr
Anticipated expiration legal-status Critical
Publication of WO2001043546A3 publication Critical patent/WO2001043546A3/fr
Ceased legal-status Critical Current

Links

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

Definitions

  • the invention relates to the technical field of crop protection agents, in particular the combinations of herbicidal alkyl azines and safeners, in particular combinations of herbicidal 2,4-diaminotriazines and safeners, which are outstandingly suitable for use against harmful plants in crops of useful plants.
  • Herbicidal active ingredients from the alkylazine series for example derivatives of 2,4-diamino-1, 3,5-triazine substituted in the 6-position, have good application properties and can be used in relatively small amounts against a broad spectrum of grass-like and broad-leaved weeds become; see.
  • herbicide antidotes compounds which act as safeners (herbicide antidotes) on the crop plants.
  • the invention therefore relates to herbicide / safener combinations, for example in the form of preparations for use as herbicidal compositions, characterized in that they
  • L is a straight-chain or branched, optionally mono- or polysubstituted and / or bridged alkylene group having 1 to 6 carbon atoms, a CH 2 group being represented by O, N, S (0) x , where x is 0, 1 or 2 , or NO can be replaced, or a corresponding alkenylene or alkynylene group with 2 to 8 C atoms, preferably with 4 to 8 C atoms, in which a CH 2 -
  • Group can be replaced by O and which is optionally mono- or polysubstituted and / or bridged, and
  • M is an unsubstituted or substituted aryl or heterocyclyl group
  • oil active safeners are used, (B10) active substances of the dichloroacetone derivative type, (B11) active substances of the oxyimino compound type, which are known as seed dressings, (B12) active substances of the thiazolecarboxylic acid ester type, which are known as seed dressings, (B13 ) Active substances of the type of naphthalenedicarboxylic acid derivatives, which as
  • Seed dressings are known, (B14) active substances of the chromanacetic acid derivative type, (B15) active substances which, in addition to a herbicidal action against harmful plants
  • Salts consists, contain.
  • Some of the safeners are known in part as herbicidally active compounds and, in addition to the herbicidal action on harmful plants, also have a protective action on the crop plants.
  • safener The beneficial effects of safener are observed when the active ingredients (A) and (B) are applied together, but can often also be found with a delayed application (splitting). It is also possible to use the active ingredients in several portions (sequence application), e.g. after pre-emergence applications, followed by post-emergence applications or after early post-emergence applications, followed by applications in the middle or later post-emergence. It is also possible to use the safeners as dressing agents, with which the seeds of the crop plants or plant seedlings are pretreated.
  • the herbicide / safener combinations reduce or prevent phytotoxic effects which can occur when using the herbicidal active compounds (A) in useful plants without significantly impairing the effectiveness of these active compounds against harmful plants. They allow a higher dosage (application rate) of the herbicide compared to the individual application of the herbicide in crops of useful plants and thus a more effective control of the competing harmful plants.
  • the higher effectiveness enables the control of previously unrecognized species (gaps), an extension of the application period and / or a reduction in the number of necessary individual applications and - as a result for the user - economically and ecologically more advantageous weed control systems.
  • the formula (I) mentioned comprises all stereoisomers and their mixtures, in particular also racemic mixtures, and - insofar as enantiomers are possible - the respectively biologically active enantiomer or the biologically active enantiomers.
  • bonds shown in dashed lines in formula (I) represent bonds to substituents which occur in known compounds from the series of herbicidal alkyl azines at these positions or which are analogous to the substituents from the known compounds, preferably substituents which are preferred in the known Compounds from the series of herbicidal alkyl azines occur.
  • R 1 is an optionally substituted acyclic hydrocarbon residue or an optionally substituted cyclic, aromatic or cycloaliphatic hydrocarbon residue or an optionally substituted heterocyclyl residue, preferably haloalkyl with 1 to 6 C atoms,
  • R 2 is hydrogen or alkyl having 1 to 4 carbon atoms, in particular hydrogen
  • R 3 is hydrogen or alkyl having 1 to 4 carbon atoms, in particular hydrogen
  • R 4 is hydrogen
  • Preferred alkyl azines (A) of the formula (I) for the herbicide / safener combinations are compounds of the formulas (II) to (IX) below (see groups 1 to 8) and their salts:
  • R 1 (CC ⁇ ) alkyl which is unsubstituted or by one or more radicals from the group Halogen, cyano, nitro, thiocyanato, (C 1 -C 4) alkoxy, (CC 4) alkylthio, (C, - C 4) alkylsulfinyl, (C 1 -C 4) alkylsulfonyl, (C 2 -C 4) alkenyl, (C 2 -C 4 ) alkynyl, phenyl which is unsubstituted or substituted, and heterocyclyl having 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group N, O and S, the ring being unsubstituted or substituted,
  • R 2 and R 3 each independently of one another are hydrogen, amino or alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl radical, an acyclic or cyclic hydrocarbon radical or hydrocarbonoxy radical each having 1 to 10 carbon atoms or a heterocyclyl radical, heterocyclyloxy radical or heterocyclylamino radical in each case 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group N, O and S, each of the five latter radicals being unsubstituted or substituted, or an acyl radical or
  • R 2 and R 3 together with the nitrogen atom of the group NR 2 R 3 are a heterocyclic radical with 3 to 6 ring atoms and 1 to 4 hetero ring atoms, where in addition to the N atom the optionally further hetero ring atoms are selected from the group N, O and S and the rest is unsubstituted or substituted,
  • R 4 is hydrogen, amino, alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl radical, an acyclic or cyclic hydrocarbon radical or hydrocarbonoxy radical each having 1 to 10 carbon atoms, preferably having 1 to 6 carbon atoms, or a heterocyclyl radical, heterocyclyloxy radical or heterocyclylamino radical each having 3 to 6 ring atoms and 1 to 3 hetero ring atoms from the group N, O and S, each of the five last-mentioned radicals being unsubstituted or substituted, or an acyl radical,
  • R 5 is hydrogen, halogen, nitro, cyano, thiocyanato or a radical of the formula -B 1 -Y ⁇ where B 1 and Y 1 are as defined below,
  • A is an alkylene radical having 1 to 5 linearly linked C atoms or alkenylene or alkynylene each having 2 to 5 linearly linked C atoms, each of the three last-mentioned diradicals being unsubstituted or by one or more radicals from the group halogen, nitro, cyano, thiocyanato and a radical of the formula -B 2 -Y 2 is substituted, (X) n n substituents X and X in each case independently of one another halogen,
  • Y 1 , Y 2 each independently of one another H or an acyclic
  • Hydrocarbon radicals for example each with 1 to 20 carbon atoms or a cyclic hydrocarbon radical with 3 to 8 carbon atoms or a heterocyclic radical with 3 to 9 ring atoms and 1 to 3 hetero ring atoms from the group N, O and S, each of the last three radicals mentioned is unsubstituted or substituted;
  • R 1 aryl which is unsubstituted or substituted, or (C 3 -C 9 ) cycloalkyl which is unsubstituted or substituted, or heterocyclyl which is substituted or unsubstituted, or
  • each of the radicals R 6 to R 27 each independently of one another is hydrogen, halogen, nitro, cyano, thiocyanato or a radical of the formula -B 6 -D 6
  • W * each represents an oxygen atom, a sulfur atom or a group of the formula N (B 7 -D 7 ) is and
  • Heterocyclyl in the abovementioned radicals each independently represent a heterocyclic radical with 3 to 7 ring atoms and 1 to 3 heteroatoms from the group N, O and S, where a) is the total sum of the C atoms in the radicals A 1 and A.
  • R 1 and R 2 are each independently of one another hydrogen, amino, alkylamino or Dialkylamino each having 1 to 6 carbon atoms in the alkyl radical, an acyclic or cyclic hydrocarbon radical or hydrocarbonoxy radical each having 1 to 10 carbon atoms or a heterocyclyl radical, heterocyclyloxy radical, heterocyclylthio radical or heterocyclylamino radical each having 3 to 6 ring atoms and 1 to 3 hetero ring groups N, O and S, where each of the last five radicals is unsubstituted or substituted, or an acyl radical or R 1 and R 2 together with the nitrogen atom of the group NR 1 R 2 is a heterocyclic radical having 3 to 6 ring atoms and 1 to 4 hetero ring atoms, where, in addition to the N atom, the optionally further hetero ring atoms are selected from the group N, O and S and the rest are unsubstituted or substituted, R 3 is halogen, cyano, thio
  • -S (0) p -, -S (0) p -0-, -0-S (0) p -, -CO-, -CS-, -S-CO-, -CO-S-, -O-CS-, -CS-O-, -S-CS-, -CS-S-, -OCO-, -CO-O-, -NR'-, -O-NR'-, -NR'-O-, -NR'-CO- or -CO-NR'-, where p 0, 1 or 2 and R Is hydrogen, alkyl having 1 to 6 carbon atoms, phenyl, benzyl, cycloalkyl having 3 to 6 carbon atoms
  • R 1 for hydrogen or for optionally by hydroxy, cyano, halogen or C r C 4 alkoxy-substituted alkyl having 1 to 6 carbon atoms,
  • R 2 for hydrogen, for formyl, for alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl, each optionally substituted by cyano, halogen or C 1 -C 4 alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, or for each optionally substituted by cyano, CC 4 -alkoxy, halogen-C 1 -C 4 -alkoxy or C r C 4 - alkoxy-carbonyl-substituted phenylcarbonyl, naphthylcarbonyl, phenylsulfonyl or naphthylsulfonyl,
  • R 3 represents optionally cyano-, halogen or C, -.
  • X represents a substituent from the following group:
  • R (C 1 -C 6 ) alkyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, nitro, thiocyanato, (C 1 -C 4 ) alkoxy, (C r C 4 ) alkylthio, (C 1 -C 4 ) alkylsulfinyl 1 (CC 4 ) alkylsulfonyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) alkynyl and optionally substituted phenyl, or phenyl which is unsubstituted or substituted,
  • R 2 and R 3 each independently of one another are hydrogen, amino,
  • R 2 and R 3 together with the nitrogen atom of the group NR 2 R 3 are a heterocyclic radical with 3 to 6 ring atoms and 1 to 4 hetero ring atoms, where in addition to the N atom the optionally further hetero ring atoms are selected from the group N, O and S and the rest is unsubstituted or substituted,
  • R 4 is hydrogen, amino, (C r C 6 ) alkylamino, di - [(C 1 -C 6 ) alkyl] amino, one
  • a hydrocarbon radical or hydrocarbonoxy radical each having 1 to 10 carbon atoms or a heterocyclyl radical, heterocyclyloxy radical or heterocyclylamino radical each having 3 to 9 ring atoms and 1 to 3 hetero ring atoms from the group consisting of N, O and S, each of the last five radicals being unsubstituted or substituted, or an acyl residue,
  • R 5 and R 6 together form an alkylene chain with 2 to 4 carbon atoms, which is unsubstituted or substituted by one or more radicals from the group halogen, (C 1 -C 4 ) alkyl and oxo,
  • R 7 independently of other radicals R 7 each halogen, nitro, cyano,
  • X represents -O-
  • Aryl is an optionally substituted mono- or bicyclic aromatic radical having 5 to 14 ring atoms, of which 1, 2, 3 or 4 can each independently come from the group oxygen, sulfur and nitrogen; -Y- a divalent unit from the group -O-, -S-, -NR 11 -, -NR 12 CONR 13 -, -C0 2 -, -OC0 2 -, -OCONR 14 -, -SO-, -S0 2 -, -S0 2 0-, -OS0 2 0-, -S0 2 NR 14 -, -0-NR 11 -, - NR'- NR "-, wherein R 'and R" are independently defined as R 14 , and - (Y'-CR a R -CR c R d ) r Y ", in which Y * and Y" independently of one another are O, S, NH or N [(C 1 -C 4 ) alkyl], R a , R
  • R 1 and R 2 of a (CR R 2 ) group form with the carbon atom carrying them a carbonyl group, a group CR 15 R 16 or a 3- to 6-membered ring which optionally contains one or two, identical or different heteroatoms from the Group contains oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group halogen, nitro, cyano, thiocyanato and -BX 1 , or
  • R 1 of two directly or not directly adjacent (CR 1 R 2 ) groups form with the carbon atoms carrying or connecting them an optionally substituted 3- to 6-membered ring, which optionally has one or two, identical or different heteroatoms from the group Contains oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group halogen, nitro, cyano, thiocyanato and -BX 1 , or
  • R 3 , R 4 each independently of one another are a radical of a group G2 comprising hydrogen, (C r C 10 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (CC 10 ) - Alkoxy, (C 1 -C 10 ) alkylthio, (C r C 10 ) alkylsulfinyl, (CC 10 ) alkylsulfonyl, (C 3 -C 8 ) cycloalkyl, (C 3 -C 8 ) cycloalkoxy, aryl, AryKC ⁇ C ⁇ alkyl, aryl- (C r C 6 ) alkoxy, (C 3 -C 8 ) - cycloalkyl- (C 1 -C 6 ) alkyl, (C 3 -C 8 ) -Cyc!
  • R 3 and R 4 form with the carbon atom carrying them a carbonyl group, a group CR 15 R 16 or a 3- to 6-membered ring which optionally contains one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group halogen, nitro, cyano, thiocyanato and -BX 1 , or
  • R 3 of two directly or not directly adjacent (CR 3 R 4 ) groups form with the carbon atoms carrying or connecting them an optionally substituted 3- to 6-membered ring, which optionally has one or two, identical or different heteroatoms from the group Contains oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group halogen, nitro, cyano, thiocyanato and -BX 1 or
  • X 1 is hydrogen, (C r C 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 8 ) -
  • X 2 is hydrogen or heterocyclyl with 3 to 9 ring atoms, optionally substituted by one or more identical or different halogen atoms, 1, 2 or 3 of which come from the group nitrogen, oxygen and sulfur;
  • R 5 , R 6 each independently of one another a group G2, or
  • R 3 and R 5 of two directly or not directly adjacent (CR 3 R 4 ) or (CR 5 R 6 ) groups together with the carbon atoms connecting them form an optionally substituted 3- to 6-membered ring, which optionally has one or contains two, identical or different heteroatoms from the group oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group halogen, nitro, cyano, thiocyanato and -BX 1 , or
  • R 5 and R 6 form with the carbon atom carrying them a carbonyl group, a group CR 15 R 16 or a 3- to 6-membered ring which optionally contains one or two identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted by one or more, identical or different radicals from the group halogen, nitro, cyano, thiocyanato and -BX 1 , or R 6 heterocyclyl;
  • R 7 is hydrogen, amino, alkylcarbonyl, alkylamino or dialkylamino each having one to six carbon atoms in the alkyl radical, an acyclic hydrocarbon or hydrocarbonoxy radical each having one to six carbon atoms, a cyclic hydrocarbon or hydrocarbonoxy radical each having three to six carbon atoms or heterocyclyl, heterocyclyloxy or Heterocyclylamino each with three to six ring atoms and one to three hetero ring atoms from the group nitrogen, oxygen and sulfur, each of the last ten radicals optionally being replaced by one or more, identical or different radicals from the group halogen, (C 1 -C 4 ) - Alkoxy, halogen (C r C 4 ) alkoxy, (C 1 -C 4 ) alkylthio, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) -Alkenyloxy,
  • R 8 (C 1 -C 10 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, which may be replaced by one or more identical or different radicals from the group halogen, cyano, Nitro, thiocyanato, hydroxy, (C r C 4 ) alkoxy, (C r C 4 ) alkylthio, (C r C 4 ) alkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, phenyl, (C 3 -C 9 ) -cycloalkyl, (C 3 -C 9 ) -cycloalkoxy and optionally by one or more, identical or different radicals from the group halogen, amino, (C 1 -C 4 ) -alkyl, (CC 4 ) -alkoxy, halogen - (C r C 4 ) -alkyl and halogen- (C
  • R 9 , R 10 each independently of one another hydrogen, amino, (CC 10 ) -
  • R 9 and R 10 together with the nitrogen atom carrying them, form a heterocycle with a total of three to six ring atoms and one to four hetero ring atoms thereof, in addition to the nitrogen atom present, the optionally further hetero ring atoms are selected from the group consisting of oxygen, nitrogen and sulfur, and this heterocycle if appropriate is substituted;
  • R 11 is hydrogen, amino, (C ⁇ C ⁇ alkylamino, di - [(C 1 -C 10 ) alkyl] amino, (C r
  • C 10 alkyl, (C 3 -C 8 ) cycloalkyl, (C ⁇ C ⁇ cycloalkyHC ⁇ alkyl, (CC alkoxy, (CC 6 ) alkoxy- (C 1 -C 6 ) alkoxy, ( C 3 -C 8 ) cycloalkoxy, (C ⁇ C ⁇ alkylcarbonyl, where the latter nine radicals are optionally substituted;
  • R 12 , R 3 are each independently hydrogen, (C ⁇ C ⁇ alkyl, (C 2 -C 8 ) -
  • R 12 and R 13 together with the N-CO-N group carrying them form a 5- to 8-membered ring which, in addition to the two nitrogen atoms mentioned, can contain a further heteroatom from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted is;
  • R 14 is hydrogen or in each case optionally substituted (C r C 10 ) alkyl or (C 3 -C 10 ) cycloalkyl and
  • R 15 , R 16 each independently of one another hydrogen, aryl, (C r C 10 ) alkoxy, aryl
  • R 15 and R 16 form with the carbon atom carrying them a 3- to 6-membered ring which optionally contains one or two, identical or different heteroatoms from the group consisting of oxygen, nitrogen and sulfur and which is optionally substituted;
  • R 1 stands for optionally substituted alkyl with 2 to 6 carbon atoms or cycloalkyl with 3 to 6 carbon atoms
  • R 2 stands for hydrogen or for alkyl with 1 to 4 carbon atoms
  • A stands for oxygen or methylene
  • Ar stands for optionally substituted phenyl, naphthyl or heterocyclyl
  • Z represents hydrogen, halogen or optionally in each case substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl or alkynyl;
  • R 1 represents hydrogen or optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkenylcarbonyl or alkynylcarbonyl;
  • R 2 stands for hydrogen or for optionally substituted alkenyl or alkynyl
  • R 3 stands for the grouping -AZ;
  • A represents optionally substituted straight-chain or branched alkanediyl which optionally contains a hetero atom (group) from the series O, S, NH or alkylimino at the beginning or at the end or within the alkanediyl chain, and
  • A is a group of the formula NR a R b , wherein
  • R a and R b independently of one another are hydrogen, formyl or else
  • R a and R b together (CC 10 ) alkylidene which is unsubstituted or by one or more radicals from the group halogen, cyano, (C, -C 4 ) alkoxy, (C r C 4 ) haloalkoxy and (C 1 -C 4 ) Alkylthio is substituted, or
  • NR a R b together is a heterocyclyl radical having 3 to 6 ring atoms bonded to the N atom and which, in addition to the N atom as hetero ring atom, optionally contains 1 to 3 further hetero ring atoms from the group N, O and S, the heterocycle being unsubstituted or substituted, preferably unsubstituted or by one or more radicals from the group halogen, cyano, hydroxy, (C 1 -C 4 ) alkyl, (C 1 -C 4 haloalkyl, (C r C 4 ) hydroxyalkyl, (C r C 4 ) alkoxy, (C r C 4 ) haloalkoxy, (C 1 -C 4 ) hydroxyalkoxy, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkoxy, (C r C 4 ) alkoxy- (CC 4 ) alkyl and oxo , means, or (
  • (C 5 -C 6 ) cycloalkenyl each of the latter 5 radicals being unsubstituted or substituted, preferably unsubstituted or by one or several radicals from the group halogen, (C 1 -C 4 ) alkoxy, (C r C 4 ) haloalkoxy, (C r C 4 ) alkylthio, (C r C 4 ) alkoxy- (C r C 4 ) alkoxy and in the case cyclic radicals are also substituted (C 1 -C 4 ) alkyl, (C r C 4 ) haloalkyl and (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, and hydroxy, halogen or (C ⁇ C ⁇ Alkyl which is unsubstituted or substituted by one or more radicals from the group consisting of iialogen, hydroxy, mercapto, cyano, nitro, thiocyan
  • R c and R d together straight-chain (C 2 -C 5 ) alkylene which is unsubstituted or by one or more radicals from the group (CC 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) alkoxy - (C 1 -C 4 ) alkyl and oxo is substituted, R 3 is halogen, CN, N0 2 , SCN or a radical of the formula -X 1 -A 1 , where X 1 is a direct bond or a divalent group of the formula -O-,
  • X 2 is a direct bond or a divalent group of the formula -O-, -S (0) q -, -S (0) q -0-, -O -S (0) q -, -S (0) q - NR r -, -NR r -S (0) q -, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, - CS-S-, -O-CO-O-, -NR r -, -0-NR r -, -NR r -0-, - NR r -CO-, -CO-NR r -, -0-CO -NR r - or -NR r -CO-0-, in which in each case q is the integer 0, 1 or 2 and R r is hydrogen, amino, substituted amino, (C r C 6 ) alkyl, (
  • Preferred aminotriazines of the formula (I) are compounds of the group 1, 2, 3, 4, 5, 6, 7 or 8 mentioned, ie compounds of the formula (II), (III), (IV ), (V), (VI), (VII), (VIII), (IX) or (X).
  • aminotriazines of the formula (I) to be used according to the invention are those of the formula (XI)
  • R 1 (CC 4 ) alkyl or (C r C 4 ) haloalkyl
  • R 2 ( ⁇ -C alkyl), (C 3 -C 6 ) cycloalkyl or (C 3 -C 6 ) cycloalkyl (C 1 -C 4 ) alkyl and
  • Halogen is preferably chlorine, bromine and iodine; in haloalkyl halogen is preferably fluorine; R 1 is preferably -CF (CH 3 ) 2 ; R 2 is preferably (C r C 4 ) alkyl or (C 3 - C 4 ) cycloalkyl; A is preferably -CH 2 -, -CH 2 -CH 2 - or -CH 2 -CH 2 -CH 2 -.
  • aminotriazines of the formula (I) to be used according to the invention are those of the formula (XII),
  • X in formula (XII) is preferably, independently of one another, halogen, (C 1 -C 4 ) alkyl, C 1 -C 4 haloalkyl, alkoxy, (C, -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy;
  • Halogen is preferably fluorine, chlorine, bromine and iodine; in haloalkyl halogen is preferably fluorine or chlorine;
  • R 1 is preferably -CF (CH 3 ) 2 ;
  • R 2 is preferably (C r C 4 ) alkyl or (C 3 -C 4 ) cycloalkyl;
  • A is preferably -CH 2 -, -CH 2 -CH 2 - or -CH 2 -CH 2 -CH 2 -.
  • aminotriazines of the formula (I) to be used according to the invention are those of the formula (XIII)
  • R 1 is (CC 4 ) alkyl or (C r C 4 ) haloalkyl
  • R 2 (C r C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (C 3 -C 6 ) cycloalkyl- (C 1 -C 4 ) alkyl
  • n is the number 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2 or 3
  • Particularly preferred compounds of the formulas (I) to (XIII) are the compounds (A1), (A2), (A3), (A4), (A5), (A6), (A7), (A8), (A9) , (A10), (A1 1), (A12), (A13), (A14), (A15), (A16) and (A17):
  • alkyl azines of the formula (I) are known or can be prepared analogously to known methods.
  • the preparation of such compounds is described, for example, in the publications below or can be carried out, for example, by or analogously to the methods described in these publications:
  • alkyl azines (I) or their salts are compounds as described in the publications WO-A-98/42684, WO-A-99/18100, WO-A-99/19309 and WO-A-99/37627 are listed.
  • Compound (A9) is known as triaziflam (IDH-1105) (see “The Pesticide Manual”, 11th edition, The British Crop Protection Council and the Royal Soc. Of Chemistry, 1997, page 1226; "The Pesticide Manual", 11th edition , hereinafter also abbreviated as "PM”)
  • the compounds of formula (I) can by addition of a suitable inorganic or organic acid, such as HCl, HBr, H2SO4 or
  • HNOß but also oxalic acid or sulfonic acids to a basic group, such as
  • Suitable deprotonatable substituents e.g. Sulphonic acids or carboxylic acids can form inner salts with protonatable groups, such as amino groups.
  • Salts can also be formed by using suitable substituents, e.g. Sulfonic acids or carboxylic acids, the hydrogen is replaced by a cation suitable for agriculture.
  • These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts.
  • the alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio radicals and the corresponding unsaturated and / or substituted radicals in the carbon skeleton can each be straight-chain or branched.
  • the lower carbon skeletons e.g. with 1 to 6 carbon atoms or in the case of unsaturated groups with 2 to 6 carbon atoms, preferred.
  • Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl etc., mean e.g.
  • Alkynyl means e.g. Propargyl, but-2-in-1-yl, but-3-in-1-yl, 1-methyl-but-3-in-1-yl.
  • Cycloalkyl means a carbocyclic, saturated ring system with preferably 3-8 C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • substituents with a double bond on the cycloalkyl radical e.g. An alkylidene group such as methylidene.
  • multi-cyclic aliphatic systems are also included, such as, for example, bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl, Bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, adamantan-1-yl and adamantan- 2-yl.
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl.
  • substituted cycloalkenyl the explanations for substituted cycloalkyl apply accordingly.
  • Halogen means, for example, fluorine, chlorine, bromine or iodine.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 0, OCH 2 CF 3 and OCH 2 CH 2 CI; The same applies to haloalkenyl and other halogen-substituted radicals.
  • Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
  • a heterocyclic radical or ring can be saturated, unsaturated or heteroaromatic; unless otherwise defined, it preferably contains one or more, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group N, O, and ü; it is preferably an aliphatic heterocyclyl radical with 3 to 7 ring atoms or a heteroaromatic radical with 5 or 6 ring atoms.
  • the heterocyclic radical can be, for example, a heteroaromatic radical or ring (heteroaryl), such as, for example, a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more heteroatoms. It is preferably a heteroaromatic ring with a heteroatom from the group N, O and S, for example pyridyl, pyrrolyl, thienyl or furyl; furthermore it is preferably a corresponding heteroaromatic ring with 2 or 3 heteroatoms, e.g. B.
  • pyrimidinyl pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl and triazolyl.
  • Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and additionally oxo.
  • the oxo group can also be attached to the hetero ring atoms, which can exist in different oxidation states, e.g. at N and S, occur.
  • Substituted radicals such as a substituted alkyl, alkenyl, alkynyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical, mean, for example, a substituted radical derived from the unsubstituted basic body, the substituents being, for example, one or more, preferably 1, 2 or 3 radicals from the group halogen, alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl and, in the case of cyclic radicals,
  • cyclic systems are also included with those substituents which are bonded to the ring with a double bond, for.
  • radicals with carbon atoms those with 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred.
  • substituents from the group halogen for example fluorine and chlorine are preferred (C 1 -C 4) alkyl, preferably methyl or ethyl, (C 1 -C 4) haloalkyl, preferably trifluoromethyl, (C, -. C4) Alkoxy, preferably methoxy or ethoxy, (C 1 -C 4 haloalkoxy, nitro and cyano.
  • the substituents methyl, methoxy, fluorine and chlorine are particularly preferred.
  • Substituted amino such as mono- or disubstituted amino means a radical from the group of substituted amino radicals which are, for example, N-substituted by one or two identical or different radicals from the group consisting of alkyl, alkoxy, acyl and aryl; preferably mono- and dialkylamino, mono- and diarylamino, acylamino, N-alkyl-N-arylamino, N-alkyl-N-acylamino and N-heterocycles; alkyl radicals having 1 to 4 carbon atoms are preferred;
  • Aryl is preferably phenyl or substituted phenyl; the definition given below applies to acyl, preferably (CC 4 ) alkanoyl. The same applies to substituted hydroxylamino or hydrazino.
  • Optionally substituted phenyl is preferably phenyl which is unsubstituted or one or more times, preferably up to three times, by the same or various radicals from the group halogen, (C 1 -C 4 ) alkyl, (CC 4 ) alkoxy, (C 1 -C 4 ) haloalkyl, (C r C 4 ) haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyl, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-fluorophenyl, 2-, 3- and 4-trifluoromethyl-phenyl, 2,4-, 3,5-. 2,5- and 2,3-dichlorophenyl and difluorophenyl, 2,3,4-trifluoro- and trichlorophenyl, o-, m- and p-methoxyphenyl.
  • Acyl means a residue of an organic acid which is formally formed by removing a hydroxyl group on the acid function, the organic residue in the acid also being able to be linked to the acid function via a hetero atom.
  • Examples of acyl are the residue -CO-R of a carboxylic acid HO-CO-R and residues of acids derived therefrom such as thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the rest of carbonic acid monoesters, N-substituted carbamic acids, sulfonic acids, sulfinic acids, N-substituted sulfonamic acids , Phosphonic acids, phosphinic acids.
  • acyl means formyl, alkylcarbonyl such as [(CC 4 ) alkyl] carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkylalkylimidoyl and other residues of organic acids.
  • radicals in each case in the alkyl or phenyl part can be further substituted, for example in the alkyl part by one or more radicals from the group halogen, alkoxy, phenyl and phenoxy;
  • substituents in the phenyl part are the substituents already mentioned above generally for substituted phenyl.
  • Acyl preferably means an acyl radical in the narrower sense, ie a radical of an organic acid in which the acid group is directly connected to the carbon atom of an organic radical, for example formyl, alkylcarbonyl such as [(C 1 -C 4 ) alkyl] carbonyl, more specifically acetyl, or phenylcarbonyl, alkylsulfonyl, alkylsulfinyl and other residues of organic acids.
  • acyl radical in the narrower sense ie a radical of an organic acid in which the acid group is directly connected to the carbon atom of an organic radical, for example formyl, alkylcarbonyl such as [(C 1 -C 4 ) alkyl] carbonyl, more specifically acetyl, or phenylcarbonyl, alkylsulfonyl, alkylsulfinyl and other residues of organic acids.
  • the active compounds (A) are suitable for controlling in a number of plant crops, for example in economically important crops such as cereals (wheat, barley, rye, rice, maize), sugar beet, sugar cane, rapeseed, cotton and soybeans. Of particular interest is the use in cereals such as wheat and corn, especially corn. These cultures are also preferred for the combinations (A) + (B).
  • Preferred herbicide / safener combinations of one or more compounds (A) with an effective amount of one or more compounds (B) from group (B1) are compounds of the phenylpyrazoline-3-carboxylic acid type, e.g. B. the formula
  • R 1 is the same or different halogen, (C 1 -C 4 ) alkyl, (CC 4 ) alkoxy, nitro or (CC 4 ) haloalkyl; n is an integer from 0 to 5, preferably 0 to 3,
  • Heteroatoms preferably from the group O and S, which is connected via the N atom to the carbonyl group in formula (XI) and is unsubstituted or by radicals from the group (C r C 4 ) -alkyl, (C 1 -C 4 ) Alkoxy or optionally substituted phenyl, preferably a radical of the formula OR 5 ,
  • R 3 is hydrogen, (C 1 -C 4 alkyl, (C r C 8 ) haloalkyl, (C 3 -C 12 ) cycloalkyl or substituted or unsubstituted phenyl and
  • R 4 is hydrogen, (C 1 -C 4 alkyl, (C r C 8 ) haloalkyl, (C 1 -C 4 ) alkoxy (C 1 -C 4 ) alkyl, (C r C 6 ) hydroxyalkyl, ( C 3 -C 12 ) cycloalkyl or tri- (C 1 -C 4 ) alkyl silyl, and
  • R 5 , R 6 , R 7 independently of one another are hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 carbon atoms and
  • R 8 is hydrogen, (C r C 6 ) alkyl, (C r C 6 ) alkoxy or substituted or unsubstituted phenyl, preferably compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl -2-pyrazoline-3-carboxylic acid ethyl ester (B1.1) ("Mefenpyr-diethyl", see “The Pesticide Manual", 11th edition 1997, pp. 781-782), and related compounds, as described in WO 91 / 07874, ("The Pesticide Manual", 11th edition, hereinafter also abbreviated as "PM”)
  • R 1 , n, R 2 and R 3 are as defined for formula (XI), preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylate (B2.1), 1- ( 2,4-dichlorophenyl) -5-isopropyl-pyrazole-3-carboxylic acid ethyl ester (B2.2), 1- (2,4-dichlorophenyl) -5- (1, 1-dimethyl-ethyl) pyrazole-3-carboxylic acid ethyl ester (B2.3), 1 - (2,4-dichlorophenyl) -5-phenyl-pyrazole-3-carboxylic acid ethyl ester (B2.4) and related compounds as described in EP-A-333 131 and EP-A-269 806 are described;
  • R 1 , n, R 2 and R 3 are as defined for formula (XI), preferably fenchlorazole (ethyl ester), ie
  • R 1 , n and R 2 are as defined for formula (XI) and
  • R 10 is hydrogen, (C r C 8 ) alkyl, (C r C 8 ) haloalkyl, (C 3 -C 12 ) cycloalkyl or substituted or unsubstituted phenyl and m is 0 or 1; preferably compounds such as
  • R 1 , n and R 2 are as defined for formula (XI) and
  • R * is a (C or C 2 ) alkanediyl chain which is unsubstituted or substituted with one or two (C 1 -C 4 ) alkyl radicals or with [(CC 3 ) alkoxy] carbonyl; preferably
  • (B7) Active substances of the phenoxyacetic acid or propionic acid derivative or butyric acid derivative or aromatic carboxylic acid type, e.g. 2,4-dichlorophenoxyacetic acid (ester) (2,4-D) (B7.1), (RS) - or (R) - (4-chloro-2-methylphenoxy) propionic acid and ester (mecoprop or Mecoprop-P) (B7.2) or (B7.3),
  • R 21 is (C r C 4 ) alkyl, (CrOJ haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 3 -C 7 ) cycloalkyl, preferably dichloromethyl;
  • R 22 , R 23 are identical or different hydrogen, (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl,
  • (CC 4 ) alkyl (C 2 -C 4 ) alkenylcarbamoyl- (CC 4 ) alkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, dioxolanyl- (C 1 - C 4 ) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or
  • R 22 and R 23 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine
  • Morpholine, hexahydropyrimidine or benzoxazine ring mean, preferably
  • PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) methyl] dichloroacetamide from the
  • (B14) active substances of the chromanacetic acid derivative type such as, for. B.
  • (B15) active substances which, in addition to a herbicidal action against harmful plants, also have a safener action on crop plants such as rice, such as B.
  • COD 1-bromo-4- (chloromethylsulfonyl) benzene
  • R is hydrogen, a hydrocarbon radical, a hydrocarbonoxy radical, a hydrocarbonthio radical or a heterocyclyl radical which is preferably bonded via a carbon atom, each of the latter 4 radicals being unsubstituted or by one or several identical or different radicals from the group halogen, cyano, nitro, amino, hydroxy, carboxy, formyl, carbonamide, sulfonamide and radicals of the formula Z a -R a are substituted, wherein each hydrocarbon part preferably has 1 to 20 C atoms and a C-containing radical R 1 including substituents preferably has 1 to 30 C atoms;
  • R 2 is hydrogen or (CC 4 ) alkyl, preferably hydrogen, or
  • R 3 the same or different halogen, cyano, nitro, amino, hydroxy,
  • R 4 is hydrogen or (C 1 -C 4 ) alkyl, preferably H;
  • R 5 identical or different, halogen, cyano, nitro, amino, hydroxy,
  • Carboxy CHO, CONH 2 , S0 2 NH 2 or a radical of the formula Z c -R c ;
  • R a is a hydrocarbon radical or a heterocyclyl radical, each of the latter two radicals being unsubstituted or by one or more identical or different radicals from the group halogen, cyano, nitro,
  • Groups are each replaced by an oxygen atom
  • R, R c, the same or different, is a hydrocarbon radical or one
  • Heterocyclyl radical each of the latter two radicals being unsubstituted or by one or more identical or different radicals from the
  • Z a is a divalent group of the formula O, S, CO, CS, CO-O, CO-S, O-CO,
  • R * radicals in the last 5 radicals each independently represent H, (C 1 -C 4 ) alkyl or halo (C r C 4 ) alkyl;
  • Z b , Z c independently of one another a direct bond or a divalent
  • R 1 is hydrogen, heterocyclyl or a hydrocarbon radical, the latter two radicals optionally being substituted by one or more, identical or different radicals from the group halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH 2 , S0 2 NH 2 and Z d -R d are substituted;
  • R 2 is hydrogen, hydroxy, (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C r C 6 ) alkoxy, (C 2 -C 6 ) -Alkenyloxy, the five latter radicals optionally being replaced by one or more, identical or different radicals from the group halogen, hydroxy, (C 1 -C 4 -alkyl, (C r C 4 ) -alkoxy and (C r C 4 ) -
  • Alkylthio are substituted, or
  • R 1 and R 2 together with the nitrogen atom carrying them form a 3- to 8-membered saturated or unsaturated ring
  • R 3 the same or different halogen, cyano, nitro, amino, hydroxy,
  • Carboxy CHO, CONH 2 , S0 2 NH 2 or Z e -R e ;
  • R 4 is hydrogen, (CC 4 ) alkyl, (C 2 -C 4 ) alkenyl or (C 2 -C 4 ) alkynyl;
  • R 5 identical or different, halogen, cyano, nitro, amino, hydroxy,
  • R d is a (C 2 -C 20 ) alkyl radical, the carbon chain of which is interrupted one or more times by oxygen atoms, heterocyclyl or one
  • Hydrocarbon radical the latter two radicals optionally being replaced by one or more, identical or different radicals from the group
  • Halogen, cyano, nitro, amino, hydroxy, mono- and di - [(C 1 -C 4 ) alkyl] amino are substituted;
  • R e , R f the same or different, represent a (C 2 -C 20 ) alkyl radical
  • Carbon chain is interrupted one or more times by oxygen atoms
  • Residues optionally by one or more, the same or different
  • Residues from the group halogen, cyano, nitro, amino, hydroxy, phosphoryl,
  • Z d is a divalent unit from the group O, S, CO, CS, C (0) 0, C (0) S,
  • Z °, Z f is a direct bond or a divalent unit from the group 0, S, CO, CS, C (0) 0, C (0) S, SO, S0 2 , NR *, S0 2 NR * or
  • R * is hydrogen, (C r C 4 ) alkyl or (C 1 -C 4 ) haloalkyl; n is an integer from 0 to 4, and m is an integer from 0 to 5 when X is CH and an integer from 0 to 4 when X is N; z.
  • B. the compound 4- (2-methoxybenzoylsulfamoyl) -N-cyclopropylbenzamide (B17.1)
  • R 2 H halogen, (C r C 4 ) alkyl, CF 3 , (C 1 -C 4 ) alkoxy or (C r C 4 ) haloalkoxy;
  • R 3 is H, halogen or (C r C 4 ) alkyl; Q 2 , E, G are identical or different, O, S, CR 2 8 , CO, NR 9 or a group of the formula (XX),
  • R 9 together (C 2 -C 6 ) alkylene; A YR h or NR 2 10 ; XO or S (0) x ; YO or S;
  • R h H (C r C ⁇ ) alkyl t (C ⁇ haloalkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 8 ) alkyl, (C 3 -C 6 ) - alkenyloxy- ( C r C 8 ) -alkyl, or phenyl- (C r C 8 ) -alkyl, where the phenyl ring is optionally substituted by halogen, (CC 4 ) -alkyl, CF 3 , methoxy or methyl-S (0) x ; ( C 3 -C 6 ) alkenyl, (C 3 -C 6 ) haloalkenyl, phenyl- (C 3 -C 6 ) alkenyl, (C 3 -C 6 ) alkynyl, phenyl- (C 3 -C 6 ) - alkynyl, oxetanyl, furfuryl,
  • R 5 identical or different H, (C, -C 4 ) alkyl, (C 1 -C 4 ) alkylcarbonyl or the two radicals R 5 together (C 4 -C 5 ) alkylene;
  • R 6 , R 7 independently of one another in each case the same or different H, (C, -
  • R 8 identical or different, is H, (C 1 -C 8 ) alkyl or the two radicals R 8 together (C 2 -C 6 ) alkylene;
  • R 9 is H, (CC 8 ) alkyl, substituted or unsubstituted phenyl, or unsubstituted.es or benzyl substituted on the phenyl ring;
  • R 10 are the same or different H, (C r C 8 ) alkyl, phenyl, phenyl- (C 1 -C 8 ) alkyl, where a phenyl ring by F, CI, Br, N0 2 , CN, OCH 3 , (C , -C 4 ) alkyl or CH 3 S0 2 .
  • Salts Of particular interest among the safeners mentioned are (B1.1) and (B2.1) to (B2.4), (B3.1), (B4.1) to (B4.5), (B5.1) to (B5.9), (B7.1) to (B7.11), (B8.1), (B9.1), (B9.2), (B15.1), (B16.1) and (B17 .1), in particular (B1.1) and (B4.3) and (B5.1).
  • the combinations of compounds (A) (compounds of the formula (I) or their salts) and the safener (B) can be used, for example, as such or in the form of their preparations (formulations) with other pesticidally active substances, such as. B. insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators can be used in combination, for. B. as a finished formulation or as a tank mix.
  • active ingredients such as those described in, for example, Weed Research 26, 441-445 (1986) or "The Pesticide Manual", 11th edition, The British, can be used as combination partners (C) for the active ingredients according to the invention in mixture formulations or in the tank mix Crop Protection Council and the Royal Soc. of Chemistry, 1997 and the literature cited therein.
  • Known herbicides or plant growth regulators which can be combined with the compounds of the formula (I) are, for example, the following active compounds; the compounds are referred to below either with the "common name" (usually according to the English spelling) according to the International Organization for Standardization (ISO) or with the chemical name, possibly together with a customary code number: acetochlor; acifluorfen (-sodium); aclonifen; AKH 7088, ie [[[1- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidenes] amino] -oxy] - methyl acetate and acetic acid; alachlor; alloxydim (-sodium); ametryn; amidochlor, amidosulfuron; amitrol; AMS, ie ammonium sulfamate; anilofos; asulam; atrazine; azafenidin
  • herbicidal compositions with a synergistically active content in one or more of the following combinations of two compounds (A) + (B):
  • the application rate ranges and ratio ratios mentioned in each case are preferred. In individual cases, it can make sense to combine one of the compounds (A) with several compounds (B). Furthermore, the combinations according to the invention can be used together with other active ingredients, for example from the group of herbicides, fungicides, insecticides and plant growth regulators or from the group of additives and formulation auxiliaries customary in crop protection.
  • the application rate of herbicides A can be varied widely, the optimal amount depends on the particular herbicide, the range of harmful plants and the crop plants. As a rule, the application rate is in the range from 10 to 1200, preferably 15 to 800, very preferably 10 to 150 g of active ingredient (A.S.) / ha.
  • the herbicidal active ingredients and the safeners can be applied together (as a finished formulation or in a tank mix process) or in succession in any order.
  • the weight ratio of herbicide (A): safener (B) can vary within wide limits and is, for example, in the range from 1 : 200 to 200: 1, preferably 1: 100 to 100: 1, in particular 1: 20 to 20: 1, very particularly 1:10 to 10: 1.
  • the respectively optimal amounts of herbicidal active ingredient and safner depend on the respective active ingredient (A) and safener (B) as well as on the type of plant stand to be treated and can be determined from case to case by appropriate preliminary tests.
  • the safeners can be used to pretreat the seeds of the crop (dressing the seeds) or the seedlings, or they can be introduced into the furrows before sowing.
  • the roots or the whole seedlings can be sprayed with a solution of the safener or immersed in such a solution.
  • One or more herbicides can then be applied according to the pre-emergence or post-emergence methods.
  • the safeners can be used together with the herbicides before or after the plants emerge.
  • Pre-emergence treatment includes both the treatment of the cultivated area before sowing as well as the treatment of the sown but not yet overgrown cultivated areas.
  • a sequential procedure, in which treatment with safener is carried out first and the herbicide is applied later, preferably promptly, is also possible.
  • application of the safener after application of the herbicide may also be useful.
  • the required application rates of the safeners can vary depending on the indication and the herbicidal active ingredient used and are generally in the range from 0.001 to 5 kg, preferably 0.005 to 0.5 kg, of safeners (active ingredient) per hectare.
  • the invention therefore also relates to a process for protecting crop plants from phytotoxic side effects of a herbicide (A), counter-characterized by the application of an antidote-effective amount of one or more safeners (B) before, after or simultaneously with the herbicide (A) on the Plants, parts of plants, plant seeds or the area under cultivation.
  • A herbicide
  • B an antidote-effective amount of one or more safeners
  • herbicide-safener combinations according to the invention have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants. Perennial weeds that are difficult to control and that sprout from rhizomes, rhizomes or other permanent organs are also well captured by the active ingredients.
  • Some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned in detail, which can be controlled by the compounds according to the invention, without any intention that the name should limit them to certain species.
  • the monocotyledonous weed species for example, Agrostis, Alopecurus, Apera, Avena, Brachicaria, Bromus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Festuca, Fimbristylis, Ischaemum, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Sagittaria, Scirpus, Setaria, Sphenoclea, as well as Cyperus species predominantly from the annual group and on the part of the perennial species Agropyron, Cynodon, Imperata as well as Sorghum and also perennial Cyperus species well recorded.
  • herbicidal activity in dicotyledonous weeds such as Ambrosia, Anthemis, Carduus, Centaurea, Chenopodium, Cirsium, Convoivulus, Datura, Emex, Galeopsis, Galinsoga, Lepidium, Lindernia, Papaver, Portlaca, Polygonum, Ranunculus, Rorippa, Rioaes, Sotala, Sotala, Sotala Solanum, Sonchus, Taraxacum, Trifolium, Urtica and Xanthium observed.
  • herbicidal activity in dicotyledonous weeds such as Ambrosia, Anthemis, Carduus, Centaurea, Chenopodium, Cirsium, Convoivulus, Datura, Emex, Galeopsis, Galinsoga, Lepidium, Lindernia, Papaver, Portlaca, Polygonum, Ranunculus, Rorippa, Rioaes, Sotala, Sotala, Sotala Solanum
  • the compounds according to the invention are applied to the surface of the earth before germination, either the weed seedlings emerge completely or the weeds grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks.
  • the combinations according to the invention are excellent herbicidal Have activity against monocotyledonous and dicotyledonous weeds, crops of economically important crops such as wheat, barley, rye, triticale, oats, millet, rice, manioc, corn, sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables only slightly or not at all damaged.
  • crops of economically important crops such as wheat, barley, rye, triticale, oats, millet, rice, manioc, corn, sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables only slightly or not at all damaged.
  • the present compounds are very well suited for the selective control of undesired plant growth in agricultural crops, including ornamental crops.
  • the combinations according to the invention have excellent growth-regulating properties in crop plants. They intervene in the plant's metabolism in a regulating manner and can thus be used to influence plant constituents in a targeted manner and to facilitate harvesting, e.g. by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesired vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as this can reduce or completely prevent storage.
  • the active substance combinations can also be used to control harmful plants in crops of known or still to be developed genetically modified plants.
  • the transgenic plants are generally distinguished by special advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern e.g. ß. the crop in terms of quantity, quality, storability, composition and special ingredients.
  • transgenic plants with an increased starch content or altered starch quality or those with a different fatty acid composition of the crop are known.
  • the combinations according to the invention are preferably used economically important transgenic crops of useful and ornamental plants, e.g. B. of cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • useful and ornamental plants e.g. B. of cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • new plants which have modified properties in comparison to previously occurring plants are, for example, classic breeding methods and the generation of mutants.
  • new plants with modified properties can be produced using genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624).
  • genetic engineering changes in crop plants have been described in order to modify the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827,
  • transgenic crop plants which have resistance to other herbicides, for example to sulfonyl resins (EP-A-0257993, US-A-
  • Bacillus thuringiensis toxins (Bt toxins) which the
  • nucleic acid molecules can be introduced into plasmids that have a mutagenesis or a sequence change allow by recombination of DNA sequences.
  • B. base exchanges partial sequences removed or natural or synthetic sequences added.
  • adapters or linkers can be attached to the fragments.
  • the production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect or the expression of at least one appropriately constructed ribozyme which specifically cleaves transcripts of the gene product mentioned above.
  • DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
  • the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a particular compartment, z. B. the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • the transgenic plant cells can be regenerated into whole plants using known techniques.
  • the invention also relates to the use of the herbicidal compositions comprising combinations of (A) + (B) for controlling harmful plants, preferably in plant crops.
  • the active compound combinations according to the invention can be present both as mixed formulations of the two components, if appropriate with further active compounds, additives and / or customary formulation auxiliaries, which are then diluted with water in the customary manner, or as so-called tank mixes by diluting the separately formulated or partially separated formulated components can be made with water.
  • the compounds (A) and (B) or their combinations can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified.
  • general formulation options are: wettable powder (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions, dispersions Oil- or water-based, suspoemulsions, dusts (DP), mordants, granules for soil or litter application or water-dispersible granules (WG), ULV formulations, microcapsules or waxes.
  • combinations with other pesticidally active substances such as other herbicides, fungicides or insecticides, and safeners, fertilizers and / or growth regulators can also be prepared, e.g. in the form of a finished formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or inert substance, but also ionic or nonionic surfactants (wetting agents, dispersing agents), e.g. polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesulfonates or alkylbenzenesulfonates, ligninsulfonic acid sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid sodium or also oleoylmethyltauric acid sodium.
  • ionic or nonionic surfactants e.g. polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesulfonates or alkylbenzenesulfonates
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, eg butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons with the addition of one or more ionic or nonionic surfactants (emulsifiers).
  • organic solvent eg butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons.
  • ionic or nonionic surfactants emulsifiers
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, Alkyl polyether, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester or polyoxethylene sorbitol ester.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solid substances e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers. Water-dispersible granules are generally produced using processes such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations usually contain 0.1 to 99
  • Percentage by weight in particular 2 to 95% by weight of active ingredients of types A and / or B, the following concentrations being customary, depending on the type of formulation:
  • the active substance concentration in wettable powders is e.g. about 10 to 95% by weight of the
  • the remainder to 100 wt .-% consists of conventional formulation components.
  • the active substance concentration can e.g. 5 to 80% by weight.
  • Dust-like formulations usually contain 5 to 20% by weight of active ingredient, sprayable solutions about 0.2 to 25% by weight of active ingredient.
  • the active ingredient content depends in part on whether the active compound is liquid or solid and which one
  • Granulating agents and fillers can be used.
  • the content of the water-dispersible granules is between 10 and 90
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, preservatives, antifreezes and solvents, fillers, dyes and carriers, defoamers, evaporation inhibitors, agents which control the pH or Affect viscosity, thickeners, fertilizers and / or dyes.
  • the formulations present in the commercial form are optionally diluted in the customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water.
  • Preparations in the form of dust, ground granules or granules for spreading, and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the herbicidal compositions can be applied to the plants, parts of plants, plant seeds or the area under cultivation (arable soil), preferably to the green plants and parts of plants and, if appropriate, additionally to the arable soil.
  • arable soil preferably to the green plants and parts of plants and, if appropriate, additionally to the arable soil.
  • One possible application is the joint application of the active ingredients in the form of tank mixes, the optimally formulated concentrated formulations of the individual active ingredients being mixed together with water in the tank and the spray liquor obtained being applied.
  • a common herbicidal formulation of the combination of active compounds (A) and (B) according to the invention has the advantage of being easier to use because the amounts of the components have already been set in the correct ratio to one another.
  • the auxiliaries in the formulation can be optimally coordinated with one another, while a tank mix of different formulations can result in undesired combinations of auxiliaries.
  • a dusting agent is obtained by adding 10 parts by weight of a Active ingredient / active ingredient mixture and 90 parts by weight of talc as an inert material and comminuted in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of an active substance / active substance mixture, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of lignosulphonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium mixes as a wetting and dispersing agent and grinds in a pin mill.
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of an active compound / active compound mixture with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight. Parts of paraffinic mineral oil (boiling range approx. 255 to 277 ° C) and ground in a friction ball mill to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of an active ingredient / active ingredient mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.
  • a water-dispersible granulate is obtained by adding 75 parts by weight of an active ingredient / active ingredient mixture,
  • a water-dispersible granulate is also obtained by adding 25 parts by weight of an active ingredient / active ingredient mixture,
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants are placed in pots in sandy loam and covered with soil.
  • the agents formulated in the form of concentrated aqueous solutions, wettable powders or emulsion concentrates are then applied as an aqueous solution, suspension or emulsion with a water application rate of the equivalent of 300 to 800 l / ha in different dosages to the surface of the covering earth.
  • the pots are placed in the greenhouse and kept under good growth conditions for the weeds.
  • the optical damage to the plants or the emergence damage is assessed after a test period of 3 to 4 weeks in comparison to untreated controls. As the test results show, the compositions according to the invention have good herbicidal pre-emergence activity against a broad spectrum of grasses and weeds.
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds are placed in pots in sandy loam soil, covered with soil and grown in the greenhouse under good growth conditions (temperature, humidity, water supply). Three weeks after sowing, the test plants at the three-leaf stage are treated with the agents according to the invention.
  • the compositions according to the invention formulated as wettable powder or as emulsion concentrates are sprayed onto the green parts of the plant in various dosages with a water application rate of the equivalent of 300 to 800 l / ha. After the test plants have stood in the greenhouse for about 3 to 4 weeks under optimal growth conditions, the effect of the preparations is assessed visually in comparison to untreated controls (cf. section 1).
  • the agents according to the invention also have good herbicidal activity against a broad spectrum of economically important grasses and weeds, even after emergence.
  • Transplanted and sown rice as well as typical rice weeds and weeds are grown in the greenhouse up to the three-leaf stage (Echinochloa crus-galli 1, 5-leaf) under paddy rice conditions (water accumulation height: 2 - 3 cm) in closed plastic pots.
  • the treatment with the compounds according to the invention then takes place.
  • the formulated active ingredients are suspended in water, dissolved or emulsified and, by means of pouring, applied to the test plants' ramewater in different dosages.
  • the test plants are placed in the greenhouse under optimal growth conditions and are kept this way throughout the test period. About three weeks after application, the evaluation of the plant damage is carried out visually in comparison to untreated controls (see example 1).
  • Cultivated plants were grown outdoors on plots under natural field conditions, whereby seeds or rhizome pieces of typical harmful plants had been laid out or the natural weed was used.
  • the treatment with the agents according to the invention took place after the emergence of the harmful plants and the crop plants, as a rule in the 2 to 4 leaf stage; in some cases (as indicated), individual active substances or combinations of active substances were applied preemergent (see Section 1) or postemergent (see Section 2) or as sequence treatment, partially preemergent and / or postemergent. After application, e.g. B. 2, 4, 6 and 8 weeks after application, the effect of the preparations was rated visually in comparison to untreated controls (see rating in section 1).
  • Rice plants of the "Nihonbare” variety were grown under greenhouse conditions. In the 2-leaf stage, the rice plants so grown were immersed with the root in safener solution (variants with several minutes and hours) so that the roots were completely covered with safener solution. Instead of the root, the entire rice plant can also be placed in the safener solution. The rice plants were then transplanted into plastic pots and grown for several days (e.g. 4 days) under greenhouse conditions until application with the herbicide. The herbicide was applied as a water or overhead treatment. The final scoring was carried out 3 weeks after the herbicide application as in Example 1.
  • ORYSA Oryza sativa (rice) (A1) Compound of formula (A1), i.e. H. 4-Amino-6- (1-fluoro-1-methyl-ethyl) -2- (3-phenyl-1-cyclobutyl-propylamino) -1, 3,5-triazine
  • ORYSA Oryza sativa (rice)
  • ZEAMA maize Zea mays
  • variety Lorenzo A2
  • Compound of formula (A2) d. H. 4-amino-6- (1-fluoro-1-methyl-ethyl) -2- (4-phenyl-1-cyclopropyl-butylamino) -1, 3,5-triazine
  • ZEAMA maize (Zea mays), variety Lorenzo
  • A2 Compound of Formula (A2), i.e. H. 4-Amino-6- (1-fluoro-1-methyl-ethyl) -2- (4-phenyl-1-cyclopropyl-butylamino) -1, 3,5-triazine
  • A6 Compound of Formula (A6), i.e. , H. 4-Amino-6- (1-fluoro-1-methylethyl) -2- [3- (4-fluoro-3-methylphenoxy) -1-ethyl-propylamino] -1, 3,5-triazine
  • ZEAMA maize (Zea mays)

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)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Combinaisons herbicides-phytoprotecteurs caractérisées en ce qu'elles comprennent (A) un ou plusieurs composés à activité herbicide ayant une structure partielle de formule (I), dans laquelle L désigne un groupe alkylène de 1 à 6 atomes C, à chaîne linéaire ou ramifiée, éventuellement monosubstitué ou polysubstitué et/ou ponté, où un groupe CH2 peut être remplacé par O, N, S(O)x, où x est égal à 0, 1, ou 2, ou NO, ou un groupe alcénylène ou alcinylène de 2 à 8 atomes C, de préférence de 4 à 8 atomes C, avec un groupe CH2 pouvant être remplacé par O, et qui est éventuellement mono- ou polysubstitué et/ou ponté, et M désigne un groupe aryle ou hétérocyclyle, non substitué ou substitué, et B) un ou plusieurs phytoprotecteurs choisis dans le groupe comprenant les composés (B1) à (B18) qui sont définis dans la revendication 1. Les combinaisons précitées sont utilisées pour combattre sélectivement les plantes nuisibles dans des cultures de plantes utiles.
PCT/EP2000/011862 1999-12-15 2000-11-28 Combinaisons d'alkylazines herbicides et de phytoprotecteurs Ceased WO2001043546A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU23601/01A AU2360101A (en) 1999-12-15 2000-11-28 Combinations of herbicidal alkylazines and safeners

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1999160684 DE19960684A1 (de) 1999-12-15 1999-12-15 Kombinationen von herbiziden Alkylazinen und Safenern
DE19960684.6 1999-12-15

Publications (2)

Publication Number Publication Date
WO2001043546A2 true WO2001043546A2 (fr) 2001-06-21
WO2001043546A3 WO2001043546A3 (fr) 2002-06-20

Family

ID=7932874

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/011862 Ceased WO2001043546A2 (fr) 1999-12-15 2000-11-28 Combinaisons d'alkylazines herbicides et de phytoprotecteurs

Country Status (3)

Country Link
AU (1) AU2360101A (fr)
DE (1) DE19960684A1 (fr)
WO (1) WO2001043546A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011064533A3 (fr) * 2009-11-27 2012-02-16 Syngenta Limited Compositions herbicides

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3939503A1 (de) * 1989-11-30 1991-06-06 Hoechst Ag Neue pyrazoline zum schutz von kulturpflanzen gegenueber herbiziden
DE59209849D1 (de) * 1991-04-15 2000-08-24 Aventis Cropscience Gmbh Isoxazoline oder Isothiazoline enthaltende pflanzenschützende Mittel, neue Isoxazoline und Isothiazoline und Verfahren zu deren Herstellung
JPH06509712A (ja) * 1991-07-30 1994-11-02 バイオ−テクニカル・リソーシス 水の不純物を検出するための装置
JPH05339109A (ja) * 1992-06-08 1993-12-21 Idemitsu Kosan Co Ltd 除草剤組成物
DE19842894A1 (de) * 1998-09-18 2000-03-23 Hoechst Schering Agrevo Gmbh Synergistische Wirkstoffkombinationen zur Bekämpfung von Schadpflanzen in Nutzpflanzenkulturen
DE19912637A1 (de) * 1999-03-20 2000-09-21 Aventis Cropscience Gmbh 2,4-Diamino-1,3,5-triazine, Verfahren zur Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011064533A3 (fr) * 2009-11-27 2012-02-16 Syngenta Limited Compositions herbicides
CN102665416A (zh) * 2009-11-27 2012-09-12 辛根塔有限公司 除草剂组合物
US20130053242A1 (en) * 2009-11-27 2013-02-28 Syngenta Crop Protection Llc Herbicidal compositions
US8648011B2 (en) 2009-11-27 2014-02-11 Syngenta Crop Protection Llc Herbicidal compositions

Also Published As

Publication number Publication date
DE19960684A1 (de) 2001-06-21
AU2360101A (en) 2001-06-25
WO2001043546A3 (fr) 2002-06-20

Similar Documents

Publication Publication Date Title
EP1478628B1 (fr) 2-amino-4-bicycloamino-6h-1,3,5-triazines, procede permettant de les produire et leur utilisation comme herbicides et regulateurs de croissance de plantes
DE102004054666A1 (de) Substituierte Pyrazol-3-carboxamide, Verfahren zur Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE102004054665A1 (de) Substituierte bi- und tricyclische Pyrazol-Derivate Verfahren zur Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren
EP1771071B1 (fr) Agents herbicides
WO2007003294A1 (fr) Derives de 3-[1-halo-1-aryl-methan-sulfonyl]- et 3-[1-halo-1-heteroaryl-methan-sulfonyl]-isoxazoline, procede pour les preparer et leur utilisation en tant qu'herbicides et regulateurs de croissance vegetale
EP1130965A1 (fr) Combinaisons d'herbicides et de phytoprotecteurs
DE19607450A1 (de) 2-Amino-4-bicycloamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
EP1087948B1 (fr) 2,4-diamino-1,3,5-triazines, leur procede de production et leur utilisation comme herbicides et regulateurs de la croissance vegetale
DE19522137A1 (de) 2-Amino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE60304862T2 (de) Kombinationen von herbiziden aromatischen carbonsäuren und safener-mitteln
EP2121639A2 (fr) 2,4-diamino-1,3,5-triazines substituées, procédé de production de celles-ci et utilisation de celles-ci comme herbicides et régulateurs de croissance végétale
DE10135043A1 (de) Substituierte 3-Heteroaryl(amino- oder oxy)-pyrrolidin-2-one, Verfahren zu deren Herstellung und Verwendung als Herbizide oder als Pflanzenwachstumsregulatoren
DE19936438A1 (de) Kombinationen von Herbiziden und Safenern
EP1163229A1 (fr) 2,4-diamino-1,3,5-triazines, leur procede de production et leur utilisation comme herbicides et regulateurs de la croissance des plantes
WO2001044208A1 (fr) Derives de 2-amino-1,3,5-triazine 4,6-substituee, leur procede de fabrication et leur utilisation comme herbicides et regulateurs de croissance des plantes
EP1303498A1 (fr) 2-amino-1,3,5-triazines substituees et leur utilisation comme herbicides et regulateurs de croissance des plantes
WO2007118589A1 (fr) Diamino-1,3,5-triazines substituées, leur procédé de fabrication et leur utilisation comme herbicides et régulateurs de croissance des plantes
EP1222178A1 (fr) Alkyl-amino-1,3,5-triazines et leur utilisation comme herbicides
WO2001043546A2 (fr) Combinaisons d'alkylazines herbicides et de phytoprotecteurs
WO2002081459A1 (fr) Alkyl-amino-1,3,5-triazines, leur procede de production et leur utilisation comme herbicides et regulateurs de la croissance des plantes
WO2002092580A2 (fr) 2,4-diamino-1,3,5-triazines, leur procede de production et leur utilisation comme herbicides et regulateurs de la croissance vegetale
DE102005063066A1 (de) 2-[Pyrazolyl-methan-sulfonyl])-pyridin-N-oxid-Derivate und 2-[Pyrazlyl-methan-sulfinyl])-pyridin-N-oxid-Derivate, Verfahren zu deren Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AU AZ BA BB BG BR BY BZ CA CN CR CU CZ DM DZ EE GD GE HR HU ID IL IN IS JP KG KP KR KZ LC LK LR LT LV MA MD MG MK MN MX NO NZ PL RO RU SG SI SK TJ TM TT UA UZ VN YU ZA

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
AK Designated states

Kind code of ref document: A3

Designated state(s): AE AG AL AM AU AZ BA BB BG BR BY BZ CA CN CR CU CZ DM DZ EE GD GE HR HU ID IL IN IS JP KG KP KR KZ LC LK LR LT LV MA MD MG MK MN MX NO NZ PL RO RU SG SI SK TJ TM TT UA UZ VN YU ZA

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP