Herbicide safener compositions

Patent metadata

Field	Value
Publication number	US-9332759-B2
Application number	US-201214004868-A
Country	US
Kind code	B2
Filing date	Mar 12, 2012
Priority date	Mar 15, 2011
Publication date	May 10, 2016
Grant date	May 10, 2016

Abstract

Herbicide-safener compositions are described, comprising active ingredients from the group of the N-(1,2,5-oxadiazol-3-yl)benzamides and safeners. These herbicidal compositions are particularly suitable for use against harmful plants in crops of useful plants.

First claim

The invention claimed is:

1. A herbicide-safener composition comprising:
(A) at least one compound of formula (I) and/or a salt thereof

 in which
W is N,
R is hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyl, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, or methoxymethyl, or
is heteroaryl, heterocyclyl or phenyl, each being substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,

X and Z are each independently nitro, halogen, cyano, formyl, thiocyanato, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-halocycloalkyl-(C 1 -C 6 )-alkyl, COR 1 , OR 1 , OCOR 1 , OSO 2 R 2 , S(O) n R 2 , SO 2 OR 1 , SO 2 N(R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-OCOR 1 , (C 1 -C 6 )-alkyl-OSO 2 R 2 , (C 1 -C 6 )-alkyl-COOR 1 , (C 1 -C 6 )-alkyl-SO 2 OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 , NR 1 R 2 , or P(O)(OR 5 ) 2 , or
is heteroaryl, heterocyclyl or phenyl each substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen,

R 1 is hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-halocycloalkyl, (C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the 12 latter radicals are substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , SCOR 3 , NR 3 COR 3 , CO 2 R 3 , COSR 3 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl,
R 2 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, each being substituted by s radicals selected from the group consisting of cyano, halogen, nitro, thiocyanato, OR 3 , S(O) n R 4 , N(R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , SCOR 3 , NR 3 COR 3 , CO 2 R 3 , COSR 3 , CON(R 3 ) 2 and (C 1 -C 4 )-alkoxy-(C 2 -C 6 )-alkoxycarbonyl,
R 3 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
R 4 is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl or (C 2 -C 6 )-alkynyl,
R 5 is methyl or ethyl,
n is 0, 1 or 2, and
s is 0, 1, 2 or 3,

and
(B) at least one safener.

2. The herbicide-safener composition as claimed in claim 1 , in which
W is N,
R is hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, or methoxymethyl,
X and Z are each independently nitro, halogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-cycloalkyl, OR 1 , S(O) n R 2 , (C 1 -C 6 )-alkyl-S(O) n R 2 , (C 1 -C 6 )-alkyl-OR 1 , (C 1 -C 6 )-alkyl-CON(R 1 ) 2 , (C 1 -C 6 )-alkyl-SO 2 N(R 1 ) 2 , (C 1 -C 6 )-alkyl-NR 1 COR 1 , (C 1 -C 6 )-alkyl-NR 1 SO 2 R 2 or 1,2,4-triazol-1-yl,
R 1 is hydrogen, (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, phenyl or phenyl-(C 1 -C 6 )-alkyl, where the seven latter radicals are substituted by s radicals selected from the group consisting of halogen and OR 3 ,
R 2 is (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, each being substituted by s radicals selected from the group consisting of halogen and OR 3 , R 3 is hydrogen or (C 1 -C 6 )-alkyl,
n is 0, 1 or 2, and
s is 0, 1, 2 or 3.

3. The herbicide-safener composition as claimed in claim 1 , in which
W is N,
R is amino, cyclopropyl, isopropyl, t-butyl, methyl, ethyl, methoxy, bromine or chlorine,
X is chlorine, methoxymethyl or methyl, and
Z is trifluoromethyl.

4. The herbicide-safener composition as claimed in claim 1 , comprising at least one safener selected from the group consisting of mefenpyr-diethyl, fenchlorazole, isoxadifen-ethyl, cloquintocet-mexyl, dichlormid, 3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine, benoxacor, 3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane, 1-dichloroacetylazepane, furilazole, ((R)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine), cyprosulfamide, N-isopropyl-4-sulfamoylbenzamide, 1-(2-methoxyphenyl)ethanone, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, oxabetrinil, fluxofenim, cyometrinil, 1,8-naphthalenedicarboxylic anhydride, fenclorim, flurazole, dietholate, dimepiperate, daimuron and cumyluron.

5. The herbicide-safener composition as claimed in claim 4 , comprising at least one safener selected from the group consisting of daimuron, benoxacor, furilazole, fluxofenim, fenchlorazole (ethyl ester), mefenpyr-diethyl, cloquintocet-mexyl, isoxadifen-ethyl, cyprosulfamide, flurazole, oxabetrinil, dichlormid and dietholate.

6. The herbicide-safener composition as claimed in claim 5 , comprising at least one compound of formula (I) and/or salt thereof and at least one safener selected from the group consisting of mefenpyr-diethyl, isoxadifen-ethyl, cyprosulfamide, fenchlorazole ethyl ester, benoxacor, cloquintocet-mexyl, fluxofenim and furilazole.

7. A method for controlling a harmful plant in a crop comprising applying a herbicidally active amount of a composition as claimed in of claim 1 to said harmful plant, a plant part, a plant seed and/or an area on which a plant grows.

8. The method as claimed in claim 7 , wherein the crop is selected from the group consisting of sugarcane, corn, wheat, rye, barley, oats, rice, sorghum, cotton and soya.

9. The method as claimed in claim 7 , wherein the crop has been genetically modified.

Assignees

• Köhn Arnim
• Van Almsick Andreas
• Ahrens Hartmut
• Ziemer Frank
• Dörner-Rieping Simon
• Rosinger Christopher Hugh
• Hacker Erwin
• Bayer Ip Gmbh

Inventors

• Köhn Arnim
• Van Almsick Andreas
• Ahrens Hartmut
• Ziemer Frank
• Dörner-Rieping Simon
• Rosinger Christopher Hugh
• Hacker Erwin

Classifications

• A01N43/82 Primary

  five-membered rings with three ring hetero atoms · CPC title

• C07D271/08 Primary

  1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles · CPC title

• A01N25/32

  Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions · CPC title

• C07D417/14

  containing three or more hetero rings · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title