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(12) Patent Application Publication (10) Pub. No.: US 2007/0021303 A1 Rosinger Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2007/0021303 A1 Rosinger Et Al US 2007002 1303A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2007/0021303 A1 Rosinger et al. (43) Pub. Date: Jan. 25, 2007 (54) SAFENING METHOD Publication Classification (76) Inventors: Christopher Rosinger, Hofheim (DE); (51) Int. Cl. Jan Van Den Berg, Heythuysen (NL); AOIN 25/32 (2006.01) Bart Geraats, Weert (NL) (52) U.S. Cl. .............................................................. SO4/105 Correspondence Address: FROMMER LAWRENCE & HAUG (57) ABSTRACT 745 FIFTHAVENUE- 1 OTH FL. NEW YORK, NY 10151 (US) The invention relates to the sue of a compound (B) as (21) Appl. No.: 11/183,661 safener for reducing or avoiding phytotoxic side-effects of a pesticide (A) in useful plants selected from the plant order (22) Filed: Jul. 18, 2005 Liliflorae, wherein (A) is one or more pesticides, and (B) is one or more Safeners selected from the group consisting of (30) Foreign Application Priority Data safeners (B1) to (B19) as defined in claim 1. The safener can be applied by various methods including spraying tech Jul. 20, 2004 (DE).......................... 10 2004 O35 136.8 niques and seed treatment. US 2007/002 1303 A1 Jan. 25, 2007 SAFENING METHOD thyl-2-pyrazoline-3-carboxylate (B1-1) (“Mefenpyr-di 0001. The invention relates to the technical field of crop ethyl”. PM, pp. 622-623) and related compounds as they protection compositions and safening of crops against phy are described in WO 91/07874; totoxic effects of pesticides, in particular safening of crops 0011 (B2) dichlorophenylpyrazolecarboxylic acid of Some useful plants selected from a specific plant order derivatives, preferably compounds such as ethyl 1-(2,4- against pesticides which are highly suitable for use against dichlorophenyl)-5-methylpyrazole-3-carboxylate (B2-1), harmful organisms in said crops. ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-car 0002 The application of pesticides such as herbicides boxylate (B2-2), ethyl 1-(2,4-dichlorophenyl)-5-(1,1- and also fungicides and insecticides against harmful organ dimethylethyl)pyrazole-3-carboxylate (B2-3), ethyl 1-(2, isms in crops of useful plants is often limited by phytotoxic 4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate effects of the pesticides in said crops. As a result the (B2-4) and related compounds as they are described in application of the particular pesticide in said crop is not EP-A-333 131 and EP-A-269 806; possible at all or possible only at an application rate where 0012 (B3) compounds of the triazolecarboxylic acids the desired effect against harmful organisms is insufficient. type, preferably compounds Such as fenchlorazol and its 0003 For example, it is known that many herbicides ethyl ester, i.e. ethyl 1-(2,4-dichlorophenyl)-5-trichlorom injure crop plants at herbicide application rates needed to ethyl-(1H)-1,2,4-triazole-3-carboxylate (B3-1), and control weed growth. This renders many herbicides unsuit related compounds (see EP-A-174 562 and EP-A-346 able for controlling weeds in the presence of certain crops. 620): Where weed growth in crops is uncontrolled however, this 0013 (B4) compounds of the 5-benzyl- or 5-phenyl-2- results in lower crop yield and reduced crop quality, as isoxazoline-3-carboxylic acid type or the 5,5-diphenyl-2- weeds will compete with crops for nutrients, light and water. isoxazoline-3-carboxylic acid, preferably compounds Reduction in herbicidal injury to crops without an unaccept such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-car able reduction in the herbicidal action can be accomplished boxylate (B4-1) or ethyl 5-phenyl-2-isoxazoline-3-car by use of crop protectants known as “safeners', also some boxylate (B4-2) and related compounds as they are times referred to as “antidotes' or “antagonists’. The safen described in WO91/08202, or ethyl 5,5-diphenyl-2-isox ing effect of a compound is generally more or less specific azoline-3-carboxylate (B4-3) (“isoxadifen-ethyl”. PM, p. to the herbicidal partner and the crop where the active 588) or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxy ingredients are applied. late (B4-4) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isox 0004. Likewise some crops can be protected by specific azoline-3-carboxylate (B4-5), as they are described in safeners or antidots which are able to reduce or avoid the German Patent Application (WO-A-95/07897); phytotoxicity of other pesticides Such as fungicides or pesticides against harmful animals, such as insecticides, 0014 (B5) compounds of the 8-quinolinoxyacetic acid acaricides, nematicides, molluscicides or miticides (in short type, preferably 1-methylhex-1-yl (5-chloro-8-quinoli together also called just “insecticides') towards the crops noxy)acetate (common name "cloquintocet-mexyl) (B5 without reducing or substantially reducing the desired effect 1) (see PM, pp. 196-197) of the pesticides against harmful organisms. 0015 1,3-dimethylbut-1-yl(5-chloro-8-quinolinoxy)ac 0005 Various commercial safeners have been developed etate (B5-2), for major cereal crops including maize, mainly for Safening the crops against damage of herbicides. The use of Safeners 0016 4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate against damage of pesticides in other culture crops such as (B5-3), vegetable crops is relatively rare. 00.17 1-allyloxyprop-2-yl(5-chloro-8-quinolinoxy)ac 0006 We have now shown that, surprisingly, some crop etate (B5-4), plants selected from useful plants of the order Liliflorae can ethyl(5-chloro-8-quinolinoxy)acetate (B5-5), be effectively protected against undesirable damage by 0.018 pesticides if the pesticides are applied together with certain 0019) methyl(5-chloro-8-quinolinoxy)acetate (B5-6), compounds acting as Safeners to the crop plants. allyl (5-chloro-8-quinolinoxy)acetate (B5-7), 0007 Accordingly, the present invention provides a use 0020 of a compound (B) as safener for reducing or avoiding 0021 2-(2-propylideneiminooxy)-1-ethyl(5-chloro-8- phytotoxic side-effects of a pesticide (A) in useful plants quinolinoxy)acetate (B5-8), selected from the plant order Liliflorae, wherein 0022 2-oxoprop-1-yl(5-chloro-8-quinolinoxy)acetate 0008 (A) is one or more pesticides, preferably selected (B5-9), from herbicides, insecticides and fungicides, or agricul turally acceptable salts thereof, and and related compounds as are described in EP-A-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-0 492 366; 0009 (B) is one or more safeners selected from the group consisting of (abbreviation “PM used herein means “The 0023 (B6) compounds of the (5-chloro-8-quinolinoxy )malonic acid type, preferably compounds Such as Pesticide Manual, 13th edition): diethyl(5-chloro-8-quinolinoxy)malonate, diallyl 0010 (B1) compounds of the dichlorophenylpyrazoline (5-chloro-8-quinolinoxy)malonate, methylethyl(5-chloro 3-carboxylic acid type, preferably compounds such as 8-quinolinoxy)malonate and related compounds as are ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-me described in EP-A-0 582 198: US 2007/002 1303 A1 Jan. 25, 2007 0024 (B7) active substances of the phenoxyacetic or 0047 (B13) active substances of the naphthalenedicar phenoxypropionic acid derivatives type or of the aromatic boxylic acid derivatives type, Such as, for example, carboxylic acids type. Such as, for example, 0048) “naphthalic anhydride” (PM, p. 1083) (= 1,8-naph 0.025 2,4-dichlorophenoxyacetic acids (and its esters) thalenedicarboxylic anhydride) (B13-1), (2,4-D), 0049 (B14) active substances of the chromanacetic acid 0026 4-chloro-2-methylphenoxypropionic esters (meco derivatives type. Such as, for example, prop), MCPA or 0050 “CL 304415” (CAS Reg. No. 31541-57-8) (=2-(4- 0027 3,6-dichloro-2-methoxybenzoic acid (and its carboxychroman-4-yl)acetic acid by American Cyana esters) (dicamba); mid), 0028 (B8) active substances of the pyrimidines type 0051 (B15) active substances which, in addition to a which are employed in rice as soil-acting safeners, such herbicidal action against harmful plants, also exhibit a as, for example, safeneraction in connection with crop plants for example, 0029) “fenclorim' (PM, pp. 406) (=4,6-dichloro-2-phe 0.052 “dimepiperate” or “MY-93” (PM, pp. 316-317) nylpyrimidine), (=S-1-methyl-1-phenylethyl piperidine-1-carbothioate), 0030 (B9) active substances of the dichloroacetamides 0.053 “daimuron” or “SK 23” (PM, p. 259) (=1-(1- type. Such as methyl-1-phenylethyl)-3-p-tolylurea), 0031) “dichlormid' (PM, pp. 284) (=N,N-diallyl-2.2- dichloroacetamide), 0054) “cumyluron’=“JC-940” (=3-(2-chlorophenylm ethyl)-1-(1-methyl-1-phenyl-ethyl)urea, See JP-A- 0032) “R-29148” (=3-dichloroacetyl-2.2.5-trimethyl-1,3- 60087254), oxazolidine, by Stauffer), 0.055 “methoxyphenone' or “NK 049” (=3,3'-dimethyl 0033) “benoxacor” (PM, pp. 72-73) (=4-dichloroacetyl 4-methoxybenzophenone), “CSB' (=1-bromo-4-(chlo 3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (B9-1), romethylsulfonyl)benzene) (CAS Reg. No. 54091-06-4, 0034) “PPG-1292 (=N-allyl-N-(1,3-dioxolan-2-yl)m- by Kumiai), ethyldichloroacetamide by PPG Industries), 0056 (B16) N-acylsulfonamides of the formula (S3) and 0035) “DK-24” (=N-allyl-N-(allylaminocarbonyl)m- their salts ethyldichloroacetamide by Sagro-Chem), 0036) “AD-67 or “MON 4660 (=3-dichloroacetyl-1- (S3) oxa-3-azaspiro4.5decane by Nitrokemia and Monsanto, respectively), R! N S-N 0037) “diclonon” or “BAS145138” or “LAB145138” N / o (=3-dichloroacetyl-2.5.5-trimethyl-1,3-diazabicyclo O 4.3.0nonane by BASF) and O (R) 0038) “furilazol” or “MON 13900” (see PM, 507) (=(RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazo lidine); 0057) as are described in WO-A-97/.45016: 0039 (B10) active substances of the dichloroacetone 0.058 (B17) acylsulfamoylbenzamides of the formula derivatives type, such as, for example, (S4), if appropriate also in salt form, 0040) “MG 191” (CAS Reg.
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