IP Library Granted Patent US 8,530,384
Granted Patent B2
US 8,530,384 · App. 10/591,674 · Granted Sep 10, 2013

Herbicides based on substituted thien-3-yl-sulphonylamino(thio) carbonyl-triazolin(thi)ones and 4-HPPD-inhibitors

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Quick Facts
Patent No.
US 8,530,384
App. No.
10/591,674
Granted
Sep 10, 2013
Kind
B2
Abstract

The invention relates to herbicidal compositions comprising an effective amount of an active ingredient combination composed of (a) at least one substituted thien-3-ylsulfonylamino(thio)carbonyltriazolin(thi)one of the formula (I) in which R 1 , R 2 and R 3 are as defined in the description, —or salts of the compounds of the formula (I)— and (b) one or more compounds from a second group of herbicides which comprises selected 4-HPPD inhibitors, and, if desired, additionally (c) a crop plant tolerance promoter compound. The invention further relates to the use of the compositions for controlling unwanted plant growth and to a process for producing the compositions.

Claims (30)

1. A composition comprising an effective amount of an active ingredient combination comprising

(a) at least one substituted thien-3-ylsulfonylamino(thio)carbonyl-triazolin(thi)one of the formula (I)

in which

R 1 is optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl having 1 to 6 carbon atoms,

R 2 is hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine or iodine, is optionally fluorine-, chlorine-, bromine-, cyano-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkyl-carbonyl- or C 1 -C 4 -alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, is in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, is in each case optionally fluorine-, chlorine-, cyano-, C 1 -C 4 -alkoxy- or C 1 -C 4 -alkoxy-carbonyl-substituted alkoxy, alkylthio, alkylamino or alkylcarbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, is alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylamino or alkynylamino having in each case 3 to 6 carbon atoms in the alkenyl or alkynyl group, is dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, is in each case optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino, is in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C 1 -C 4 -alkyl-substituted cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl or cycloalkenyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, or is in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C 1 -C 4 -alkyl-, trifluoromethyl-, C 1 -C 4 -alkoxy- and/or C 1 -C 4 -alkoxy-carbonyl-substituted aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino or arylalkylamino having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety,

R 3 is hydrogen, hydroxyl, amino, cyano, is C 2 -C 10 -alkylideneamino, is optionally fluorine-, chlorine-, bromine-, cyano-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkyl-carbonyl- or C 1 -C 4 -alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, is in each case optionally fluorine-, chlorine- and/or bromine-substituted alkenyl or alkynyl having in each case 2 to 6 carbon atoms, is in each case optionally fluorine-, chlorine-, bromine-, cyano-, C 1 -C 4 -alkoxy- or C 1 -C 4 -alkoxy-carbonyl-substituted alkoxy, alkylamino or alkyl-carbonylamino having in each case 1 to 6 carbon atoms in the alkyl group, is alkenyloxy having 3 to 6 carbon atoms, is dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, is in each case optionally fluorine-, chlorine-, bromine-, cyano- and/or C 1 -C 4 -alkyl-substituted cycloalkyl, cycloalkylamino or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the alkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, or is in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C 1 -C 4 -alkyl-, trifluoromethyl- and/or C 1 -C 4 -alkoxy-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety

or salts of the compounds of the formula (I)

and

(b)

wherein there are 0.1 to 50 parts by weight of Compound B-3 per part by weight of the at least one substituted thien-3-ylsulfonylamino(thio)carbonyl-triazolin(thi)one of the formula (I) and, if desired, additionally

(c) a crop plant tolerance promoter compound from the following group of compounds:

4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 5-chloroquinoxalin-8-oxyacetic acid 1-methylhexyl ester (cloquintocet-mexyl), 2,4-dichlorophenoxyacetic acid (2,4-D), 2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid), N-(4-methylphenyl)-N′-(1-methyl-1-phenylethyl)urea (daimuron), 4,6-dichloro-2-phenylpyrimidine (fenclorim), 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazole-ethyl), 2-chloro-4-trifluoromethylthiazole-5-carboxylic acid phenylmethyl ester (flurazole), 4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluorophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), (4-chloro-2-methylphenoxy)acetic acid (MCPA), (+-)-2-(4-chloro-2-methylphenoxy)propanoic acid (mecoprop), diethyl 1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191, CAS Reg. No. 96420-72-3), 1,8-naphthalic anhydride, α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292), 3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148), N-cyclopropyl-4-[[(2-methoxy-5-methylbenzoyl)amino]sulfonyl]benzamide, N-[[(4-methylaminocarbonylamino)phenyl]-sulfonyl-2-methoxybenzamide, and compounds of the formula (II) below,

in which

R 21 and R 22 are as defined in the following table:

R 21

R 22

cyclopropyl

2-OCH 3

cyclopropyl

2-OCH 3 , 5-Cl

ethyl

2-OCH 3

isopropyl

2-OCH 3 , 5-Cl

isopropyl

2-OCH 3 .

2. The composition as claimed in claim 1 , wherein the crop plant tolerance promoter compound is selected from the active ingredients benoxacor, mefenpyr-diethyl, fenchlorazole-ethyl, isoxadifen-ethyl, cloquintocet-mexyl, and the compound N-cyclopropyl-4-[[[(2-methoxybenzoyl)amino]sulfonyl]benzamide.

3. A method of controlling weeds, comprising applying the composition of claim 1 to weeds and/or their habitat, wherein said composition further comprises surface active agents and/or extenders.

4. A process for producing a herbicidal composition comprising, mixing a composition of claim 1 with surface-active agents and/or extenders.

5. A composition according to claim 1 , wherein R 1 is CH 3 ; R 2 is —OCH 3 ; and R 3 is CH 3 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 11, 2019
From: BAYER INTELLECTUAL PROPERTY GMBH
To: BAYER CROPSCIENCE AKTIENGESELLSCHAFT
Reel/Frame 049359/0698 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 20, 2015
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 034990/0879 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 27, 2007
From: DOLLINGER, MARKUS, DR.; SANTEL, HANS-JOACHIM, DR.; GESING, ERNST RUDOLF, DR.; HACKER, ERWIN, DR.
To: BAYER CROPSCIENCE AG
Reel/Frame 019485/0647 →