Combinations of herbicides and safeners

专利摘要:
The present invention relates to a herbicide composition comprising at least one herbicidally active compound of formula (I) and at least one crop plant protection compound as an emollient: Formula I Where V is an optionally substituted radical selected from the group consisting of isoxazol-4-yl, pyrazol-4-yl, cyclohexane-1,3-dione-2-yl and 3-oxopropiononitrile-2-yl, R 9 is a nitro, amino, halogen or carbon-containing radical. Emollient groups include, for example, 2,4-D, cymetrinyl, dicamba, dimrone, fenchlorim, flurazole, fluxofenim, lactidichlor, MCPA, mecoprop, MG-191, Oxavetrinyl, methyl diphenylmethoxy acetate, 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea, 1,8-naphthalene anhydride, 1- [4- ( N-naphthoylsulfamoyl) phenyl] -3-dimethylurea, (4-chlorophenoxy) acetic acid, 4- (2,4-dichlorophenoxy) butyric acid, (4-4-chloro-o-tolyl) butyric acid, 4- (4-chlorophenoxy) butyric acid, in each case their acids and esters, N-acylsulfonamides, N-acylsulfamoylbenzamides, in each case suitably also in the form of salts Optionally substituted 1-phenylpyrazoline, 1-phenylpyrazole, 1-phenyltriazole, 5-phenylisoxazolin and 5-phenylmethylisoxazolin-3-carboxylic acid ester (8-quinolinyloxy) acetic acid induction It includes.
公开号:KR20010080501A
申请号:KR1020017006303
申请日:1999-11-05
公开日:2001-08-22
发明作者:지에메르프랑크；빌름스로타르；비에린거헤르만；하케르에르빈
申请人:바이세르트, 리펠；아벤티스 크롭사이언스 게엠베하；
IPC主号:

专利说明:

Mixtures of Herbicides and Mitigators {COMBINATIONS OF HERBICIDES AND SAFENERS}
[2] Some of the more recent herbicidal active substances that inhibit p-hydroxyphenyl pyruvate dioxygenase (HPPDO) have very good properties in use and have a wide range of monocotyledonous and dicotyledonous weeds. It may be applied at very low rates (see, eg, MP Prisbylla et al., Brighton Crop Protection Conference-Weeds (1993), 731-738).
[3] USP 5627131, EP 551650 and EP 298680 disclose certain mixtures of emollients, in particular preemergence and herbicides.
[4] It is also known in various documents that the benzoylcyclohexanedione herbicides as inhibitors of para-hydroxy-phenylpyruvate deoxygenase are based on the same mechanism of action as the benzoylisoxazole herbicides (in this regard, the literature J. Pesticide Sci. 21, 473-478 (1996), Weed Science 45, 601-609 (1997), Pesticide Science 50, 83-84, (1997) and Pesticide Outlook, 29-32, (December 1996). Furthermore, Pesticide Science 50, 83-84, (1997) shows that benzoylisoxazoles of formula A can be rearranged under specific conditions to afford benzoyl-3-oxopropionitrile of formula B This is known:
[5]
[6]
[7] However, many of these highly effective active substances are not fully compatible with some important crop plants, such as corn, rice or cereals (ie, lack of selectivity) and their use is strictly limited. In some crops of useful plants, they can be used only in very low proportions, where the widespread herbicidal activity required for weeds is not guaranteed or at all no herbicidal activity. In particular, most of the aforementioned herbicides cannot be used completely selectively against harmful plants in corn, rice, cereals or some other crops.
[8] In order to solve these disadvantages, it is known to use herbicidally active substances in admixture with so-called emollients or antidotes. Mitigators for the purposes of the present invention are compounds or mixtures of compounds that offset or reduce the phytotoxic properties of herbicides for useful plants without essentially reducing herbicide activity for harmful plants.
[9] Finding a laxative for a particular class of herbicides remains a challenge because the exact mechanism by which laxatives reduce the deleterious activity of herbicides is not known. Therefore, the fact that a compound mixed with a particular herbicide acts as an emollient cannot give conclusions as to whether such compound exhibits emollient action with other classes of herbicides. Therefore, it has been found that when a safener is used to protect useful plants from the side effects of herbicides, a number of safeners may still exhibit certain disadvantages. These include:
[10] Emollients reduce the action of herbicides on harmful plants.
[11] Not enough properties to protect useful plants
[12] When mixed with certain herbicides, the range of useful plants to which the emollient / herbicide is to be applied is not wide enough.
[13] Certain emollients may not always be combined with a sufficiently large number of herbicides.
[14] It is an object of the present invention to find compounds suitable for increasing the selectivity of these herbicides for important crop plants in combination with the aforementioned herbicides.
[15] Surprisingly, a group of compounds has been found that increase the selectivity of these herbicides for important crop plants, along with certain herbicides that act as HPPDO inhibitors.
[1] The present invention relates to crop protection products, in particular herbicide / detoxifying mixtures (herbicide / emollient mixtures), which are well suited for use in controlling competitive harmful plants in crops which are useful plants.
[16] Therefore, the present invention includes mixtures of the following compounds A and B, provided that
[17] (a) in the compound of formula I, V is V1 or V4; The emollient is a compound of formula IV or 1,8-naphthalene anhydride, methyldiphenylmethoxyacetate, 2-dichloro-methyl-2-methyl-1,3-dioxolane, cyanomethoxyimino (phenyl) acetonitrile, 1,3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile, 4'-chloro-2,2,2-trifluoroacetophenone O-1,3-dioxolan-2-ylmethyloxime, 4 , 6-dichloro-2-phenylpyrimidine, benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate and 1-methylhexyl (5-chloro-8-quinolineoxy) Mixtures selected from the group consisting of acetates; or
[18] b) In compounds of formula I, V is V3 and R ⁶ is OH; The emollient is a compound of formula II wherein W is W1, W2, W3 or W4 and m 'is 1, T is unsubstituted or substituted with 1 or 2 (C ₁ -C ₄ ) -alkyl radicals (C ₁ -or C ₂ ) -alkanediyl chain compound of formula (III), compound of formula (IV), or 1,8-naphthalene anhydride, oxavetrinyl, cyanomethoxyimino (phenyl) acetonitrile, fluxofenim and flurazole Mixtures which are compounds selected from the group relate to herbicidal active compositions which are excluded:
[19] A. A herbicidally active amount of at least one compound of formula (I):
[20]
[21] Where
[22] V is a radical selected from the group consisting of the following formulas V1 to V4:
[23]
[24]
[25]
[26]
[27] [Wherein the symbols and indices have the following meanings:
[28] R is hydrogen, (C ₁ -C ₄ ) -alkoxycarbonyl, (C ₁ -C ₄ ) -haloalkoxycarbonyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkyl Sulfinyl, (C ₁ -C ₄ ) -alkylthio, COOH or cyano, preferably hydrogen or (C ₁ -C ₄ ) -alkoxycarbonyl;
[29] R ¹ is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl, (C ₃ -C ₈ ) -cycloalkyl, (C ₃ -C ₈ ) -cycloalkenyl, (C ₁ -C ₄ ) -alkyl- (C ₃ -C ₈ ) -cycloalkyl, (C ₃ -C ₇ ) -halocycloalkyl, (C ₁ -C ₄ ) -Alkylthio- (C ₃ -C ₈ ) -cycloalkyl, (C ₁ -C ₈ ) -haloalkyl or (C ₂ -C ₈ ) -haloalkenyl, preferably (C ₃ -C ₇ ) -cyclo Alkyl or (C ₁ -C ₄ ) -alkyl- (C ₃ -C ₇ ) -cycloalkyl;
[30] R ² is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -haloalkyl, halogen, (C ₁ -C ₄ ) -haloalkoxy, cyan Furnace or nitro, preferably hydrogen;
[31] R ³ is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkylcarbonyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ )- Haloalkylsulfonyl, (C ₁ -C ₄ ) -alkyl-substituted or unsubstituted arylsulfonyl, (C ₁ -C ₄ ) -alkyl-substituted or unsubstituted arylcarbonyl- (C ₁ -C ₄ ) -alkyl or (C ₁ -C ₄ ) -alkyl-substituted or unsubstituted aryl- (C ₁ -C ₄ ) -alkyl, preferably hydrogen, (C ₁ -C ₄ ) -alkyl, (C _1- C ₄ ) -alkyl-substituted arylsulfonyl, (C ₁ -C ₄ ) -alkyl-arylcarbonylmethyl, benzyl;
[32] R ⁴ is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl, (C ₁ -C ₄ ) -haloalkyl, phenyl or Benzyl, preferably (C ₁ -C ₄ ) -alkyl;
[33] R ⁵ is (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -Dialkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkylthio, halogen, substituted or unsubstituted aryl, tetrahydropyran-4-yl, tetrahydropyran-3-yl, Tetrahydrothiopyran-3-yl, 1-methylthiocyclopropyl or 2-ethylthiopropyl, or two radicals R ⁵ together are (C ₂ -C ₄ ) -alkylene, preferably (C ₁ -C ₄ ) -alkyl or (C ₁ -C ₄ ) -alkoxy, or two radicals R ⁵ are C ₂ -alkenyl;
[34] R ⁶ is hydroxyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₈ ) -haloalkoxy, formyloxy, (C ₁ -C ₄ ) -alkylcarbonyloxy, (C ₁ -C ₄ ) -Alkylsulfonyloxy, (C ₁ -C ₄ ) -alkylthio, (C ₁ -C ₄ ) -haloalkylthio, arylthio, aryloxy, (C ₁ -C ₄ ) -alkylsulfinyl or (C _1- C ₄ ) -alkylsulfonyl, preferably hydroxyl, (C ₁ -C ₄ ) -alkoxy, phenylthio;
[35] R ⁷ is (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₃ -C ₈ ) -cycloalkyl, (C ₁ -C ₄ ) -alkyl- (C ₃ -C ₈ ) -cycloalkyl or (C ₃ -C ₈ ) -halocycloalkyl, preferably (C ₃ -C ₇ ) -cycloalkyl;
[36] R ⁸ is cyano, (C ₁ -C ₄ ) -alkoxycarbonyl, (C ₁ -C ₄ ) -alkylcarbonyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ )- Alkylsulfinyl, (C ₁ -C ₄ ) -alkylthio, (C ₁ -C ₄ ) -alkylaminocarbonyl or (C ₁ -C ₄ ) -dialkylaminocarbonyl, preferably cyano;
[37] I is an integer of 0 to 6, preferably 0 to 3, and when I is 2 or more, the radicals R ⁵ may be the same or different from each other,
[38] R ⁹ is the same or different and is nitro, amino, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl, halogen, (C _1- C ₄ ) -haloalkyl, (C ₂ -C ₄ ) -haloalkenyl, (C ₂ -C ₄ ) -haloalkynyl, (C ₁ -C ₄ ) -haloalkoxy, (C ₁ -C ₄ )- Haloalkylthio, (C ₁ -C ₄ ) -alkoxycarbonyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkylsulfinyl, (C ₁ -C ₄ ) -alkylthio , Arylsulfonyl, arylsulfinyl, arylthio, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ )- alkylthio - (C ₁ -C ₄₎ - alkoxy, (C ₁ -C ₄₎ - alkyl-carbonyl, (C ₁ -C ₄₎ - alkyl-amino sulfonyl, (C ₁ -C ₄₎ - dialkylamino sulfonic Phonyl, (C ₁ -C ₄ ) -alkylcarbamoyl, (C ₁ -C ₄ ) -dialkylcarbamoyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, phenoxy, Cyano, aryl, alkylamino or dialkylamino, preferably (C ₁ -C ₄ ) -alkyl, halogen, nitro, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -haloalkoxy , (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkylsulfonyloxy, (C ₁ -C ₄ ) -alkylsulfonylamino, (C ₁ -C ₄ ) -alkoxycarbonyl;
[39] q is 0, 1, 2, 3 or 4, preferably 0, 1, 2, or 3; And
[40] B. at least one safener in an amount of detoxifying effect selected from the group consisting of the following compounds a) to e):
[41] a) a compound of formula (II)-(IV)
[42]
[43]
[44]
[45] [Wherein the symbols and indices have the following meanings:
[46] n 'is a natural number of 0 to 5, preferably 0 to 3;
[47] T is a (C ₁ or C ₂ ) -alkanediyl chain unsubstituted or substituted by one or two (C ₁ -C ₄ ) -alkyl radicals or [(C ₁ -C ₃ ) -alkoxy] carbonyl;
[48] W is selected from the group of partially unsaturated or aromatic five-membered heterocyclic rings having 1-3 hetero ring atoms of the N or O type, wherein the ring contains one or more N atoms and one or less O atoms Unsubstituted or substituted diatoms are heterocyclic radicals, preferably radicals selected from the group consisting of the formulas W1 to W4:
[49]
[50]
[51]
[52]
[53] (Wherein
[54] m 'is 0 or 1;
[55] R ¹⁷ and R ¹⁹ are the same or different and are halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, nitro or (C ₁ -C ₄ ) -haloalkyl;
[56] R ¹⁸ and R ²⁰ are the same or different and are OR ²⁴ , SR ²⁴ , NR ²⁴ R ²⁵ or a substituted or unsubstituted 3 to 7 membered heterocycle having one or more N atoms and up to 3 hetero atoms, preferably Preferably a group selected from the group consisting of O and S, connected via a N atom to the carbonyl group of the compounds of the formulas (II) and (III), and (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy or Not substituted or substituted by radicals selected from the group consisting of optionally substituted phenyl, preferably radicals of the general formula OR ²⁴ , NHR ²⁵ or N (CH ₃ ) ₂ , in particular radicals of the general formula OR ²⁴ ;
[57] R ²⁴ is hydrogen or an unsubstituted or substituted, preferably aliphatic hydrocarbon radical having 1 to 18 carbon atoms in total;
[58] R ²⁵ is hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₁ -C ₆ ) -alkoxy or substituted or unsubstituted phenyl;
[59] R ²⁶ is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (C _1- C ₆ ) -hydroxyalkyl, (C ₃ -C ₁₂ ) -cycloalkyl or tri- (C ₁ -C ₄ ) -alkyl-silyl;
[60] R ²⁷ , R ²⁸ and R ²⁹ are the same or different and are hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₃ -C ₁₂ ) -cycloalkyl or substituted or substituted Unsubstituted phenyl;
[61] R ²¹ is (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -haloalkenyl or (C ₃ -C ₇ ) -cycloalkyl, preferably dichloromethyl;
[62] R ²² and R ²³ are the same or different and are hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl, (C ₁ -C ₄ ) -Haloalkyl, (C ₂ -C ₄ ) -haloalkenyl, (C ₁ -C ₄ ) -alkylcarbamoyl- (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenylcarba Moyl- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, dioxoranyl- (C ₁ -C ₄ ) -alkyl, thiazolyl, furyl , Furylalkyl, thienyl, piperidyl or substituted or unsubstituted phenyl, or
[63] R ²² and R ²³ together form a substituted or unsubstituted heterocyclic ring, preferably oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring);
[64] b) at least one compound selected from the group consisting of:
[65] 1,8-naphthalinic anhydride,
[66] Methyl diphenylmethoxy acetate,
[67] Cyanomethoxyimino (phenyl) acetonitrile (thiomethynyl),
[68] 1,3-dioxoran-2-ylmethoxyimino (phenyl) acetonitrile (oxabetrinyl),
[69] 4'-chloro-2,2,2-trifluoroacetophenone O-1,3-dioxolan-2-ylmethyloxime (fluxopenim),
[70] 4,6-dichloro-2-phenylpyrimidine (fenchlorim),
[71] Benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole),
[72] 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),
[73] N- (4-methylphenyl) -N '-(1-methyl-1-phenylethyl) urea (dimron),
[74] 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
[75] 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea,
[76] 1- [4- (N-4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea,
[77] 1- [4- (N-naphthoylsulfamoyl) phenyl] -3,3-dimethylurea,
[78] (2,4-dichlorophenoxy) acetic acid (2,4-D),
[79] (4-chlorophenoxy) acetic acid,
[80] (R, S) -2- (4-chloro-o-tolyloxy) propionic acid (mecoprop),
[81] 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB),
[82] (4-chloro-o-tolyloxy) acetic acid (MCPA),
[83] 4- (4-chloro-o-tolyloxy) butyric acid,
[84] 4- (4-chlorophenoxy) butyric acid,
[85] 3,6-dichloro-2-methoxybenzoic acid (dicamba),
[86] 1- (ethoxycarbonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor) and salts and esters thereof, preferably (C ₁ -C ₈ );
[87] c) N-acylsulfonamides of formula V and salts thereof:
[88]
[89] [Wherein,
[90] R ³⁰ is hydrogen, a hydrocarbon radical, a hydrocarbon-oxy radical, a hydrocarbon-thio radical or a heterocyclyl radical which is preferably bonded via a carbon atom and the last four radicals mentioned are each unsubstituted or halogen, cyano , Nitro, amino, hydroxyl, carboxyl, formyl, carboxamide, sulfonamide and one or more identical or different radicals selected from the group consisting of radicals of the general formula Z ^a -R ^a , wherein each hydrocarbon residue is Preferably the carbon-containing radical R ³⁰ containing 1 to 20 carbon atoms and including substituents preferably has 1 to 30 carbon atoms;
[91] R ³¹ is hydrogen or (C ₁ -C ₄ ) -alkyl, preferably hydrogen, or
[92] R ³⁰ and R ³¹ together with the group of the formula -CO-N- are residues of 3 to 8 membered saturated or unsaturated rings;
[93] R ³² is the same or different and is a halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, CONH ₂ , SO ₂ NH ₂ or a radical of the formula Z ^b -R ^b ;
[94] R ³³ is hydrogen or (C ₁ -C ₄ ) -alkyl, preferably hydrogen;
[95] R ³⁴ is the same or different and is a halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH ₂ , SO ₂ NH ₂ or a radical of the formula Z ^c -R ^c ;
[96] R ^a is a hydrocarbon radical or a heterocyclyl radical, wherein the two radicals mentioned last are each unsubstituted or halogen, cyano, nitro, amino, hydroxyl, mono- and di-[(C ₁ -C ₄ Substituted with one or more identical or different radicals selected from the group consisting of: -alkyl] amino), or an alkyl radical wherein a plurality, preferably two or three, non-adjacent CH ₂ groups are replaced with one oxygen atom in each case ego;
[97] R ^b and R ^c are the same or different and represent a hydrocarbon radical or a heterocyclyl radical, wherein the two radicals mentioned last are each unsubstituted or halogen, cyano, nitro, amino, hydroxyl, phosphoryl, halo- (C ₁ -C ₄ ) -alkoxy, mono- and di-[(C ₁ -C ₄ ) -alkyl] amino are substituted with one or more identical or different radicals selected from the group), or a plurality, preferably Two or three non-adjacent CH ₂ groups are in each case an alkyl radical replaced by one oxygen atom;
[98] Z ^a is a general formula O, S, CO, CS, CO-O, CO-S, 0-CO, S-CO, SO, SO ₂ , NR ^* , CO-NR ^* , NR ^* -CO, SO _2- Is a divalent group of NR ^* or NR ^* -SO ₂ , the bond given to the right of each divalent group is bonded to the radical R ^a , and the radicals R ^* in the last five radicals mentioned are each independently In H, (C ₁ -C ₄ ) -alkyl or halo- (C ₁ -C ₄ ) -alkyl;
[99] Z ^b and Z ^c are each independently a direct bond or a general formula O, S, CO, CS, CO-O, CO-S, 0-CO, S-CO, SO, SO ₂ , NR ^* , SO _2- Is a _divalent group of NR ^* , NR ^* -SO ₂ , CO-NR ^* or NR ^* -CO, in the case of an asymmetric diatomic group, the atoms on the right side are connected to the radicals R ^b or R ^c and The radicals R ^* in the two radicals are each independently in each occurrence H, (C ₁ -C ₄ ) -alkyl or halo- (C ₁ -C ₄ ) -alkyl;
[100] n is an integer from 0 to 4, preferably 0, 1 or 2, in particular 0 or 1;
[101] t is an integer from 0 to 5, preferably 0, 1, 2 or 3, in particular 0, 1 or 2;
[102] d) Acylsulfamoylbenzamides of formula VI in the form of any salt:
[103]
[104] [Wherein,
[105] X ³ is CH or N;
[106] R ³⁵ is a hydrogen, heterocyclyl or hydrocarbon radical and the last two radicals mentioned are halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH ₂ , SO ₂ NH ₂ and Z ^d -R ^d Optionally substituted with one or more identical or different radicals selected from the group consisting of;
[107] R ³⁶ is hydrogen, hydroxyl, (C ₁ -C ₆ ) -alkyl, (C ₂ -C ₆ ) -alkenyl or (C ₂ -C ₆ ) -alkynyl, (C ₁ -C ₆ ) -alkoxy or (C ₂ -C ₆ ) -alkenyloxy, the last five radicals mentioned are halogen, hydroxyl, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy and (C _1- Optionally substituted with one or more identical or different radicals selected from the group consisting of C ₄ ) -alkylthio;
[108] R ³⁵ and R ³⁶ are 3- to 8-membered saturated or unsaturated rings together with the nitrogen atom to which they are attached;
[109] R ³⁷ is the same or different and is halogen, cyano, nitro, amino, hydroxyl, carboxyl, CH0, C0NH ₂ , SO ₂ NH ₂ or Z ^e -R ^e ;
[110] R ³⁸ is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl or (C ₂ -C ₄ ) -alkynyl;
[111] R ³⁹ is the same or different and is halogen, cyano, nitro, amino, hydroxyl, carboxyl, phosphoryl, CHO, CONH ₂ , SO ₂ NH ₂ or Z ^f -R ^f ;
[112] [R ^d is a (C ₂ -C ₂₀ ) -alkyl radical wherein the carbon chain is interrupted once or more than once by an oxygen atom, or is a heterocyclyl or hydrocarbon radical, the last two mentioned radicals being halogen, cyano , nitro, amino, hydroxyl, mono- and di _{- [(C 1 -C 4)} - alkyl] is optionally substituted with a group selected from one or more identical or different radicals consisting of amino;
[113] R ^e and R ^f are the same or different and the carbon chain is a (C ₂ -C ₂₀ ) -alkyl radical interrupted once or more than once by an oxygen atom, or is a heterocyclyl or hydrocarbon radical, the last mentioned 2 Radicals in the group consisting of halogen, cyano, nitro, amino, hydroxyl, phosphoryl, (C ₁ -C ₄ ) -haloalkoxy, mono- and di-[(C ₁ -C ₄ ) -alkyl] amino Optionally substituted with one or more identical or different radicals selected;
[114] Z ^d is a divalent unit selected from the group consisting of O, S, CO, CS, C (O) O, C (O) S, SO, SO ₂ , NR ^* , C (O) NR ^*, and SO ₂ NR ^* ego;
[115] Z ^e and Z ^f are the same or different and are direct bonds or are O, S, CO, CS, C (O) O, C (O) S, SO, SO ₂ , NR ^* , SO ₂ NR ^* and C ( O) a unit selected from the group consisting of NR ^* is a unit;
[116] R ^* is hydrogen, (C ₁ -C ₄ ) -alkyl or (C ₁ -C ₄ ) -haloalkyl;
[117] s is an integer from 0 to 4;
[118] o is an integer of 0 to 5 when X is CH, and an integer of 0 to 4 when X is N; And
[119] e) a compound of formula (VII) comprising stereoisomers and agriculturally common salts:
[120]
[121] [Wherein the symbols and indices have the following meanings:
[122] R ⁴⁰ is hydrogen, (C ₁ -C ₄₎ - alkyl, (C ₁ -C ₄₎ - alkyl, or -X ⁴ (C ₁ -C ₄₎ - a (C ₁ -C ₄ alkyl substituted with halo -X ⁴ ) -Alkyl, (C ₁ -C ₄ ) -haloalkyl, NO ₂ , CN, —COO-R ⁴³ , NR ₂ ⁴⁴ , SO ₂ NR ₂ ⁴⁵ or CONR ₂ ⁴⁶ ;
[123] R ⁴¹ is hydrogen, halogen, (C ₁ -C ₄ ) -alkyl, CF ₃ , (C ₁ -C ₄ ) -alkoxy or (C ₁ -C ₄ ) -haloalkoxy;
[124] R ⁴² is hydrogen, halogen or (C ₁ -C ₄ ) -alkyl;
[125] Q ¹ , Q ² , E and G are the same or different and are O, S, CR ₂ ⁴⁷ , CO, NR ⁴⁸ or a group of formula VIII:
[126]
[127] Provided that at least one Q ¹ , Q ² , E and G group is a carbonyl group, exactly one of these groups is a radical of formula (VIII) below and the group of formula (VIII) is adjacent to a carbonyl group,
[128] β) two adjacent Q ¹ , Q ² , E and G groups cannot be oxygen at the same time;
[129] R ^g is the same or different and is hydrogen or (C ₁ -C ₈ ) -alkyl, or two radicals R ^g together are (C ₂ -C ₆ ) -alkylene;
[130] A is Y ³ -R ^h or NR ₂ ⁴⁹ ;
[131] X ⁴ is 0 or S (O) _x ;
[132] Y ³ is O or S;
[133] R ^h is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₈ ) -alkyl, (C _3- C ₆ ) -alkenyloxy- (C ₁ -C ₈ ) -alkyl, phenyl- (C ₁ -C ₈ ) -alkyl, wherein the phenyl ring is halogen, (C ₁ -C ₄ ) -alkyl, CF ₃ , Optionally substituted with methoxy or methyl-S (O) _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 or a tetrahydro-furyl;
[134] R ⁴³ is hydrogen or (C ₁ -C ₄ ) -alkyl;
[135] R ⁴⁴ is the same or different and is hydrogen, (C ₁ -C ₄ ) -alkyl or (C ₁ -C ₄ ) -alkylcarbonyl, or two radicals R ⁴⁴ together are (C ₄ -C ₅ ) -alkylene ego;
[136] R ⁴⁵ and R ⁴⁶ are each independently the same or different at each occurrence and are hydrogen or (C ₁ -C ₄ ) -alkyl, or two radicals R ⁴⁵ and / or R ⁴⁶ together are (C ₄ -C ₅ ) -Alkylene, wherein one CH ₂ group can be replaced by O or S or one or two CH ₂ groups by NR ⁱ , wherein R ⁱ is hydrogen or (C ₁ -C ₈ ) -alkyl Can be;
[137] R ⁴⁷ is the same or different and is hydrogen or (C ₁ -C ₈ ) -alkyl, or two radicals R ⁴⁷ together are (C ₂ -C ₆ ) -alkylene;
[138] R ⁴⁸ is hydrogen, (C ₁ -C ₈ ) -alkyl, substituted or unsubstituted phenyl, or unsubstituted or substituted benzyl on the phenyl ring;
[139] R ⁴⁹ is the same or different and is hydrogen, (C ₁ -C ₈ ) -alkyl, phenyl, phenyl- (C ₁ -C ₈ ) -alkyl, wherein the phenyl ring is F, Cl, Br, NO ₂ , CN, OCH ₃ , (C ₁ -C ₄ ) -alkyl or CH ₃ SO _2- ), (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₈ ) -alkyl, (C ₃ -C ₆ ) -Alkenyl, (C ₃ -C ₆ ) -alkynyl or (C ₃ -C ₆ ) -cycloalkyl, or two radicals R ⁴⁹ together are (C ₄ -C ₅ ) -alkylene, wherein one The CH ₂ group of may be replaced with O or S or one or two CH ₂ groups may be replaced with NR ^K , wherein R ^K is hydrogen or (C ₁ -C ₄ ) -alkyl;
[140] m "is 0 or 1;
[141] x is 0, 1 or 2].
[142] For the purposes of the present invention, the herbicidally active amount is the amount of one or more herbicides that can have a deleterious effect on plant growth.
[143] For the purposes of the present invention, the detoxifying amount is an amount of one or more emollients capable of at least partially preventing the phytotoxic effects of herbicides or herbicide mixtures in useful plants.
[144] Unless defined otherwise individually, the following definitions apply to the general formula and to the radicals of the formulas (I) to (VIII) in general.
[145] The radical alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and correspondingly unsaturated and / or substituted radicals are in each case straight or branched at the carbon skeleton. Preferably complex radicals such as alkyl radicals of 1 to 4 carbon atoms, or alkoxy, haloalkyl, etc., for example, methyl, ethyl, n- or i-propyl or n-, i-, t- or 2-butyl to be. Alkenyl and alkynyl radicals have the meaning of unsaturated radicals that preferably correspond to alkyl radicals, alkenyl being, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop -2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-ene -1-yl. Alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. “(C ₁ -C ₄ ) -alkyl” is an abbreviation for alkyl having 1 to 4 carbon atoms, and the same abbreviation applies similarly to the general definition of other radicals, where possible carbon numbers are indicated in parentheses.
[146] Cycloalkyl is preferably a cyclic alkyl radical of 3 to 8 carbon atoms, preferably 3 to 7, particularly preferably 3 to 6 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Cycloalkenyl and cycloalkynyl represent correspondingly unsaturated compounds.
[147] Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl, haloalkenyl and haloalkynyl are halogen, preferably fluorine, chlorine and / or bromine, in particular alkyl, alkenyl or alkynyl substituted in part or all with fluorine or chlorine, for example CF ₃ , CHF ₂ , CH ₂ F, CF ₃ CF ₂ , CH ₂ FCHCl, CCl ₃ , CHCl ₂ , CH ₂ CH ₂ Cl. Haloalkoxy is, for example, OCF ₃ , OCHF ₂ , OCH ₂ F, CF ₃ CF ₂ O, OCH ₂ CF ₃ and OCH ₂ CH ₂ Cl. This also applies similarly to radicals substituted with other halogens.
[148] The hydrocarbon radical may be an aromatic or aliphatic hydrocarbon radical, wherein the aliphatic hydrocarbon radical is preferably a straight or branched, saturated or unsaturated hydrocarbon radical having 1 to 18 carbon atoms, particularly preferably 1 to 12 carbon atoms, for example, Alkyl, alkenyl or alkynyl.
[149] Aliphatic hydrocarbon radicals preferably mean alkyl, alkenyl or alkynyl having up to 12 carbon atoms, the same meaning similarly applies to aliphatic hydrocarbon radicals in hydrocarbon-oxy radicals.
[150] Aryl is a generally monocyclic, bicyclic or polycyclic aromatic system, preferably having 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms, particularly preferably 6 to 10 carbon atoms, for example phenyl , Naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl and fluorenyl, particularly preferably phenyl.
[151] Heterocyclic rings, heterocyclic radicals or heterocyclyls are monocyclic, bicyclic or polycyclic ring systems which are saturated, unsaturated and / or aromatic, with one or more, preferably 1-4, preferably It contains a hetero atom selected from the group consisting of N, S and O.
[152] Saturated heterocycles having 3 to 7 ring atoms are preferred, wherein one or two hetero atoms are selected from the group consisting of N, O and S, but their chalcogens are not adjacent. Particular preference is given to monocyclic rings having 3 to 7 ring atoms, and heteroatoms selected from the group consisting of N, O and S, and also morpholine, dioxolane, piperazine, imidazoline and oxazolidine. Especially preferred saturated heterocycles are oxirane, pyrrolidone, morpholine and tetrahydrofuran.
[153] Also preferred are some unsubstituted heterocycles having 5 to 7 ring atoms and 1 or 2 heteroatoms selected from the group consisting of N, O and S. Preference is given to some unsaturated heterocycles having 5 to 6 ring atoms and one hetero atom selected from the group consisting of N, O and S. Particularly preferred some unsaturated heterocycles are pyrazoline, imidazoline and isoxazoline.
[154] Particularly preferred are heteroaryls, for example monocyclic having 5 to 6 ring atoms, containing 1 to 4 heteroatoms selected from the group consisting of N, O and S, and the chalcogens being non-adjacent Bicyclic aromatic heterocycle.
[155] Monocyclic aromatic heterocycles having 5 to 6 ring atoms containing heteroatoms selected from the group consisting of N, O and S, and also pyrimidine, pyrazine, pyridazine, oxazole, thiazole, thiadiazole, Particular preference is given to oxadiazoles, pyrazoles, triazoles and isoxazoles. Especially more preferred are pyrazoles, thiazoles, triazoles and furans.
[156] Substituted radicals such as substituted hydrocarbon radicals are, for example, substituted alkyl, alkenyl, alkynyl, aryl such as phenyl and arylalkyl such as benzyl, or substituted heterocyclyl, derived from an unsubstituted backbone. Substituted substituents, the substituents are preferably at least one, preferably at most 1, 2 or 3, in the case of Cl and F, up to the maximum possible number of halogens, alkoxy, haloalkoxy, alkylthio, hydroxyl Substituted amino, monoalkylamino, such as amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, acylamino , Dialkylamino and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl and haloalkylsulfonyl, and in the case of cyclic radicals, also the saturated hydrocarbon-containing substituents mentioned above Corresponding alkyl and haloalkyl, and the substituents unsubstituted aliphatic, preferably alkenyl, alkynyl, alkenyl is oxy, and alkynyloxy. Preference is given to radicals having 1 to 4 carbon atoms, especially 1 or 2 carbon atoms. In principle, preferred substituents are halogen, for example fluorine or chlorine, (C ₁ -C ₄ ) -alkyl, preferably methyl or ethyl, (C ₁ -C ₄ ) -haloalkyl, preferably trifluoro Substituents selected from the group consisting of methyl, (C ₁ -C ₄ ) -alkoxy, preferably methoxy or ethoxy, (C ₁ -C ₄ ) -haloalkoxy, nitro and cyano. Particularly preferred substituents in the context of the present application are methyl, methoxy and chlorine.
[157] Mono- or di-substituted amino is for example one or two identical or different radicals selected from the group consisting of alkyl, alkoxy, acyl and aryl, preferably monoalkylamino, dialkylamino, acylamino, arylamino, It is a chemically stable radical selected from the group of substituted amino radicals N-substituted with N-alkyl-N-arylamino and N-heterocyclo. Preferred radicals in the context of the present application are alkyl radicals having 1 to 4 carbon atoms. Preferably, aryl is phenyl. Preferably, substituted aryl is substituted phenyl. The definitions given further below apply to acyl, preferably (C ₁ -C ₄ ) -alkanoyl. It also applies similarly to substituted hydroxylamino or hydrazino.
[158] Preferably, the optionally substituted phenyl is phenyl which is unsubstituted or mono- or di-substituted, preferably trisubstituted or less, and in the case of halogens such as Cl and F and also below substitutions, halogen, (C Same or different radicals selected from the group consisting of _1- C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -haloalkoxy and nitro Phenyl substituted by, for example, o-, m- and p-tolyl, dimethylphenyl, 2-, 3- and 4-chloro-phenyl, 2-, 3- and 4-trifluoro- and- Trichlorophenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
[159] Acyl radicals are preferably radicals of organic acids having 6 or less carbon atoms, for example radicals of carboxylic acids and radicals derived therefrom, for example thiocarboxylic acids which are optionally N-substituted iminocarboxylic acids, or carbonaceous Radicals of the monoester, optionally N-substituted carbamic acid, sulfonic acid, sulfinic acid, phosphonic acid, phosphinic acid. Acyl is, for example, formyl, alkylcarbonyl such as (C ₁ -C ₄ -alkyl) -carbonyl, phenylcarbonyl, and the phenyl ring to be substituted is as indicated above for phenyl or alkyl Oxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl or N-alkyl-1-iminoalkyl are possible.
[160] All stereoisomers exhibiting the same topological linkage of atoms and mixtures thereof are also within the compound range of formulas (I) to (VII). The compounds contain one or more asymmetric carbon atoms or contain double bonds not specifically indicated in the general formula. Possible stereoisomers defined by specific spatial forms, such as enantiomers, diastereomers, Z- and E-isomers, are prepared by conventional methods or by stereoselective reactions combined with the use of stereochemically pure starting materials. It can be obtained in the form of a mixture of the stereoisomers.
[161] Suitable herbicidal active substances according to the invention are the compounds of formula (I), which cannot be used alone or optimally in cereal crops, rice and / or corn, since they are too harmful to crop plants.
[162] Herbicides of formula (I) are known, for example, from EP-A 0 137 963, EP-A 0 352 543, EP-A 0 418 175, EP-A 0 496 631 and AU-A 672 058. It is. Compounds of formula (II) are, for example, EP-A 0 333 131 (ZA-89 / 1960), EP-A 0 269 806 (US-A 4,891,057), EP-A 0 346 620 (AU -A 89/34951), EP-A 0 174 562, EP-A 0 346 620 (WO-A 91/08 202), WO-A 91/07 874 or WO-A 95/07 897 (ZA 94/7120) and the references cited herein and may be prepared by the methods described herein or may be similarly prepared. Compounds of formula III are EP-A 0 086 750, EP-A 0 94349 (US-A 4,902,340), EP-A 0 191736 (US-A 4,881,966) and EP-A 0 492 366 and herein Known in the references cited therein, the methods described herein may be prepared or analogous thereto. Compounds of formula IV are known in many patent applications, for example, US-A 4,021,224 and US-A 4,021,229. Moreover, compounds of group (b) are known from CN-A 87/102 789, EP-A 365484 and The Pesticide Manual, The British Crop Protection Council and the Royal Society of Chemistry, 11th edition, Farnham 1997. have. Compounds of group (c) are described in WO-A 97/45016, compounds of group (d) are described in German Patent Application No. 197 42 951.3 and compounds of group (e) are described in WO-A 98 / 13 361. The cited references contain detailed information on preparation methods and starting materials. These references are incorporated herein by reference.
[163] Preferred herbicide / emollient mixtures include emollients of Formula II and / or Formula III, wherein the symbols and indices have the following meanings:
[164] R ²⁴ is hydrogen, (C ₁ -C ₁₈ ) -alkyl, (C ₃ -C ₁₂ ) -cycloalkyl, (C ₂ -C ₈ ) -alkenyl or (C ₂ -C ₁₈ ) -alkynyl The carbon-containing group may be substituted by one or more, preferably up to three radicals R ⁵⁰ ;
[165] R ⁵⁰ is the same or different and is halogen, hydroxyl, (C ₁ -C ₈ ) -alkoxy, (C ₁ -C ₈ ) -alkylthio, (C ₂ -C ₈ ) -alkenylthio, (C _2- C ₈₎ - alkynyl, thio, (C ₂ -C ₈₎ - alkenyloxy, (C ₂ -C ₈₎ - alkynyloxy, (C ₃ -C ₇₎ - cycloalkyl, (C ₃ -C ₇₎ -Cycloalkoxy, cyano, mono- and di-((C ₁ -C ₄ ) -alkyl) amino, carboxyl, (C ₁ -C ₈ ) -alkoxycarbonyl, (C ₂ -C ₈ ) -alkenyloxy Carbonyl, (C ₁ -C ₈ ) -alkylthiocarbonyl, (C ₂ -C ₈ ) -alkynyloxycarbonyl, (C ₁ -C ₈ ) -alkylcarbonyl, (C ₂ -C ₈ )- Alkenylcarbonyl, (C ₂ -C ₈ ) -alkynylcarbonyl, 1- (hydroxyimino)-(C ₁ -C ₆ ) -alkyl, 1-[(C ₁ -C ₄ ) -alkylimino ]-(C ₁ -C ₄ ) -alkyl, 1-[(C ₁ -C ₄ ) -alkoxyimino]-(C ₁ -C ₆ ) -alkyl, (C ₁ -C ₈ ) -alkylcarbonylamino, (C ₂ -C ₈ ) -alkenylcarbonylamino, (C ₂ -C ₈ ) -alkynylcarbonylamino, aminocarbonyl, (C ₁ -C ₈ ) -alkylaminocarbonyl, di- (C ₁ -C ₆₎ - alkylamino-carbonyl, (C ₂ -C ₆₎ - alkenyl Aminocarbonyl, (C ₂ -C ₆₎ - alkynyl, aminocarbonyl, (C ₁ -C ₈₎ - alkoxy-carbonyl-amino, (C ₁ -C ₈₎ - alkylamino-carbonyl-amino, unsubstituted or substituted by R ⁵¹ (C ₁ -C ₆ ) -alkylcarbonyloxy substituted with (C ₂ -C ₆ ) -alkenylcarbonyloxy, (C ₂ -C ₆ ) -alkynylcarbonyloxy, (C ₁ -C ₈ ) -alkylsulfonyl, phenyl, phenyl- (C ₁ -C ₆ ) -alkoxy, phenyl- (C ₁ -C ₆ ) -alkoxycarbonyl, phenoxy, phenoxy- (C ₁ -C ₆ ) -alkoxy , Phenoxy- (C ₁ -C ₆ ) -alkoxycarbonyl, phenylcarbonyloxy, phenylcarbonylamino or phenyl- (C ₁ -C ₆ ) -alkylcarbonylamino, and the last nine radicals mentioned are Unsubstituted or radicals R ⁵² , SiR ' ₃ , OSiR' ₃ , R ' ₃ Si- (C ₁ -C ₈ ) -alkoxy, CO-O-NR' ₂ , 0-N = CR ' ₂ , N = CR ' ₂ , 0-NR' ₂ , NR ' ₂ , CH (OR') ₂ , O- (CH ₂ ) _q , -CH (OR ') ₂ , CR'"(OR') ₂ , O- (CH _{2 ) w CR '"(oR"} ) 2 or R "O-CHR'" CHCOR "- (C 1 -C 6) - and mono-substituted or multi-substituted with alkoxy, preferably substituted with three Substituted with;
[166] R ⁵¹ is the same or different and is halogen, nitro, (C ₁ -C ₄ ) -alkoxy, or phenyl unsubstituted or substituted with one or more, preferably up to 3 radicals R ⁵² ;
[167] R ⁵² is the same or different and is halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -halo Alkoxy or nitro;
[168] R 'is the same or different and is hydrogen, (C ₁ -C ₄ ) -alkyl or phenyl unsubstituted or substituted with one or more, preferably up to 3 radicals R ⁵² , or two radicals R' together To form a (C ₂ -C ₆ ) -alkanediyl chain;
[169] R ″ is the same or different and is (C ₁ -C ₄ ) -alkyl, or two radicals R ″ together form a (C ₂ -C ₆ ) -alkanediyl chain;
[170] R ′ ″ is hydrogen or (C ₁ -C ₄ ) -alkyl;
[171] w is 0, 1, 2, 3, 4, 5 or 6.
[172] Particular preference is given to the herbicide / emollient mixtures according to the invention comprising the emollients of formula (II) and / or formula (III), wherein the symbols and indices have the following meanings:
[173] R ²⁴ is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₃ -C ₇ ) -cycloalkyl, said carbon-containing radicals being unsubstituted or mono- or polysubstituted by halogen or by radical R Mono- or di-substituted to ⁵⁰ , preferably mono-substituted;
[174] R ⁵⁰ is the same or different and is hydroxyl, (C ₁ -C ₄ ) -alkoxy, carboxyl, (C ₁ -C ₄ ) -alkoxycarbonyl, (C ₂ -C ₆ ) -alkenyloxycarbonyl, ( C ₂ -C ₆ ) -alkynyloxycarbonyl, 1- (hydroxyimino)-(C ₁ -C ₄ ) -alkyl, 1-[(C ₁ -C ₄ ) -alkylimino]-(C ₁ -C ₄ ) -alkyl and 1-[(C ₁ -C ₄ ) -alkoxyimino- (C ₁ -C ₄ ) -alkyl; SiR ' ₃ , 0-N = CR' ₂ , N = CR ' ₂ , NR' ₂ and ONR ' _3, wherein R' is the same or different and is hydrogen, (C ₁ -C ₄ ) -alkyl, or in pairs Is a (C ₄ -C ₅ ) -alkanediyl chain;
[175] R ²⁷ , R ²⁸ and R ²⁹ are the same or different and are hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₆ ) -haloalkyl, (C ₃ -C ₇ ) -cycloalkyl or unsubstituted or halogen, cyano, nitro, amino, mono- and di _{- [(C 1 -C 4)} - alkyl] -amino, (C ₁ -C ₄₎ - alkyl, (C ₁ -C ₄₎ - haloalkyl, At least one selected from the group consisting of (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -haloalkoxy, (C ₁ -C ₄ ) -alkylthio and (C ₁ -C ₄ ) -alkylsulfonyl Phenyl substituted with radicals;
[176] R ²⁶ is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₁ -C ₄ -alkoxy)-(C ₁ -C ₄ ) -alkyl, (C _1- C ₆ ) -hydroxyalkyl, (C ₃ -C ₇ ) -cycloalkyl or tri- (C ₁ -C ₄ ) -alkylsilyl;
[177] R ¹⁷ and R ¹⁹ are the same or different and are halogen, methyl, ethyl, methoxy, ethoxy, (C ₁ or C ₂ ) -haloalkyl, preferably hydrogen, halogen or (C ₁ or C ₂ ) -halo Alkyl.
[178] Particular preference is given to emollients in which the symbols and indices of formula II have the following meanings:
[179] R ¹⁷ is halogen, nitro or (C ₁ -C ₄ ) -haloalkyl;
[180] n 'is 0, 1, 2 or 3;
[181] R ¹⁸ is a radical of the formula OR ²⁴ ;
[182] R ²⁴ is hydrogen, (C ₁ -C ₈ ) -alkyl or (C ₃ -C ₇ ) -cycloalkyl, wherein the carbon-containing radical is unsubstituted or mono- or multi-substituted with the same or different halogen radicals Substituted, preferably substituted with less than trisubstituted or hydroxyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkoxycarbonyl, (C ₂ -C ₆ ) -alkenyloxycarbonyl , (C ₂ -C ₆ ) -alkynyloxycarbonyl, 1- (hydroxyimino)-(C ₁ -C ₄ ) -alkyl, 1-[(C ₁ -C ₄ ) -alkylimino]-( C ₁ -C ₄ ) -alkyl, 1-[(C ₁ -C ₄ ) -alkoxyimino]-(C ₁ -C ₄ ) -alkyl and general formula SiR ′ ₃ , ON = CR ′ ₂ , N = CR ′ ₂ , NR ′ ₂ and O-NR ′ ₂ are the same or different radicals selected from the group consisting of radicals of up to ₂ , preferably monosubstituted, wherein the radicals R ′ in the aforementioned formulas are the same or different and are hydrogen, (C ₁ -C ₄ ) -alkyl, or even in pairs, is (C ₄ or C ₅ ) -alkanediyl;
[183] R ²⁷ , R ²⁸ and R ²⁹ are the same or different and are hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₆ ) -haloalkyl, (C ₃ -C ₇ ) -cycloalkyl or unsubstituted Or halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, nitro, (C ₁ -C ₄ ) -haloalkyl and (C ₁ -C ₄ ) -haloalkoxy Phenyl substituted with one or more radicals selected;
[184] R ²⁶ is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (C _1- C ₆ ) -hydroxyalkyl, (C ₃ -C ₇ ) -cycloalkyl or tri- (C ₁ -C ₄ ) -alkylsilyl.
[185] Particular preference is given to emollients of formula III, wherein the symbols and indices have the following meanings:
[186] R ¹⁹ is halogen or (C ₁ -C ₄ ) -haloalkyl;
[187] n 'is 0, 1, 2 or 3, wherein (R ¹⁹ ) _n' is preferably 5-Cl;
[188] R ²⁰ is a radical of the formula OR ²⁴ ;
[189] T is CH ₂ or _{CH (COO- (C 1 -C 3} ) - alkyl);
[190] R ²⁴ is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl or (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, preferably ( C ₁ -C ₈ ) -alkyl.
[191] Particular preference is given to emollients of formula (II) in which the symbols and indices have the following meanings:
[192] W is (W1);
[193] R ¹⁷ is halogen or (C ₁ -C ₂ ) -haloalkyl;
[194] n 'is 0, 1, 2 or 3, wherein (R ¹⁷ ) _n' is preferably 2,4-Cl ₂ ;
[195] R ¹⁸ is a radical of the formula OR ²⁴ ;
[196] R ²⁴ is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -hydroxyalkyl, (C ₃ -C ₇ ) -cycloalkyl, ( C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl or tri- (C ₁ -C ₂ ) -alkylsilyl, preferably (C ₁ -C ₄ ) -alkyl;
[197] R ²⁷ is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl or (C ₃ -C ₇ ) -cycloalkyl, preferably hydrogen or (C ₁ -C ₄ )- Alkyl;
[198] R ²⁶ is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -hydroxyalkyl, (C ₃ -C ₇ ) -cycloalkyl, ( C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl or tri- (C ₁ -C ₂ ) -alkylsilyl, preferably hydrogen or (C ₁ -C ₄ ) -alkyl.
[199] Also particularly preferred are herbicide compositions comprising an emollient of formula (II) in which the symbols and indices have the following meanings:
[200] W is (W2);
[201] R ¹⁷ is halogen or (C ₁ -C ₂ ) -haloalkyl;
[202] n 'is 0, 1, 2 or 3, wherein (R ¹⁷ ) _n' is preferably 2,4-Cl ₂ ;
[203] R ¹⁸ is a radical of the formula OR ²⁴ ;
[204] R ²⁴ is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -hydroxyalkyl, (C ₃ -C ₇ ) -cycloalkyl, ( C ₁ -C ₄ -alkoxy)-(C ₁ -C ₄ ) -alkyl or tri- (C ₁ -C ₂ ) -alkylsilyl, preferably (C ₁ -C ₄ ) -alkyl;
[205] R ²⁷ is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₃ -C ₇ ) -cycloalkyl or phenyl, preferably hydrogen or (C ₁ -C ₄ ) -Alkyl.
[206] Particular preference is given to emollients of formula (II) in which the symbols and indices have the following meanings:
[207] W is (W3);
[208] R ¹⁷ is halogen or (C ₁ -C ₂ ) -haloalkyl;
[209] n 'is 0, 1, 2 or 3, wherein (R ¹⁷ ) _n' is preferably 2,4-Cl ₂ ;
[210] R ¹⁸ is a radical of the formula OR ²⁴ ;
[211] R ²⁴ is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -hydroxyalkyl, (C ₃ -C ₇ ) -cycloalkyl, ( C ₁ -C ₄ -alkoxy)-(C ₁ -C ₄ ) -alkyl or tri- (C ₁ -C ₂ ) -alkylsilyl, preferably (C ₁ -C ₄ ) -alkyl;
[212] R ²⁸ is (C ₁ -C ₈ ) -alkyl or (C ₁ -C ₄ ) -haloalkyl, preferably C ₁ -haloalkyl.
[213] Particular preference is given to emollients of formula (II) in which the symbols and indices have the following meanings:
[214] W is (W4);
[215] R ¹⁷ is halogen, nitro, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₂ ) -haloalkyl, preferably CF ₃ or (C ₁ -C ₄ ) -alkoxy;
[216] n 'is 0, 1, 2 or 3;
[217] m 'is 0 or 1;
[218] R ¹⁸ is a radical of the formula OR ²⁴ ;
[219] R ²⁴ is hydrogen, (C ₁ -C ₄ ) -alkyl, carboxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxycarbonyl- (C ₁ -C ₄ ) -alkyl, preferably Preferably (C ₁ -C ₄ ) -alkoxy-CO-CH _2- , (C ₁ -C ₄ ) -alkoxy-CO-C (CH ₃ ) (H)-, H 0 -CO-CH ₂ -or HO- CO-C (CH ₃ ) (H);
[220] R ²⁹ is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₃ -C ₇ ) -cycloalkyl or unsubstituted or halogen, (C ₁ -C ₄ ) - it is phenyl substituted by one or more radicals selected from the group consisting of: alkoxy-alkyl, (C ₁ -C ₄₎ - haloalkyl, nitro, cyano and (C ₁ -C _4).
[221] The following group of compounds is particularly suitable for use as an emollient for herbicidally active substances of formula (I):
[222] a) a compound of dichlorophenylpyrazoline-3-carboxylic acid type (ie, a compound of formula II wherein W is (W1) and (R ¹⁷ ) _{n '} is 2,4-Cl ₂ ), preferably ethyl 1- Compounds such as (2,4-dichlorophenyl) -5- (ethoxy-carbonyl) -5-methyl-2-pyrazoline-3-carboxylate (II-1), and WO-A 91/07874 Related compounds as described;
[223] b) dichlorophenylpyrazolecarboxylic acid derivative (ie, a compound of formula II wherein W is (W2) and (R ¹⁷ ) _{n '} is 2,4-Cl ₂ ), preferably ethyl 1- (2,4- Dichlorophenyl) -5-methyl-pyrazole-3-carboxylate (II-2), ethyl 1- (2,4-dichlorophenyl) -5-isopropylpyrazole-3-carboxylate (II-3), Ethyl 1- (2,4-dichlorophenyl) -5- (1,1-dimethylethyl) pyrazole-3-carboxylate (II-4), ethyl 1- (2,4-dichlorophenyl) -5-phenyl Compounds such as pyrazole-3-carboxylate (II-5), and related compounds as described in EP-A 0 333 131 and EP-A 0 269 806;
[224] c) compounds of the triazolecarboxyl compounds (ie compounds of formula II, wherein W is (W3) and (R ¹⁷ ) _{n '} is 2,4-Cl ₂ ), preferably compounds such as fenchlorazole Ie, ethyl 1- (2,4-dichlorophenyl) -5-trichloromethyl- (1H) -1,2,4-triazole-3-carboxylate (II-6), and related compounds (EP- A 0 174 562 and EP-A 0 346 620 may be referred to);
[225] d) 5-benzyl- or 5-phenyl-2-isoxazolin-3-carboxylic acid or 5,5-diphenyl-2-isoxazolin-3-carboxylic acid, wherein W is (W4) ), Preferably ethyl 5- (2,4-dichlorobenzyl) -2-isoxazolin-3-carboxylate (II-7) or ethyl 5-phenyl-2-isoxazolin-3-carboxylate (II -8) and related compounds as described in WO-A 91/08202, or ethyl 5,5-diphenyl-2-isoxazolin-as described in WO-A 95/07897 Carboxylate (II-9) or n-propyl 5,5-diphenyl-2-isoxazolin-carboxylate (II-10) or ethyl 5- (4-fluorophenyl) -5-phenyl-2-isox Sazoline-3-carboxylate (II-11);
[226] e) compounds of the 8-quinolineoxyacetic acid system, for example, compounds of formula III _wherein (R ¹⁹ ) _{n '} is 5-Cl, R ²⁰ is OR ²⁴ and T is CH ₂ , preferably EP-A 0 860 1-methyl (5-chloro-8-quinolineoxy) acetate (III-1) as described in 750, EP-A 0 094 349 and EP-A 0 191 736 or EP-A 0 492 366 , 1,3-dimethyl-but-1-yl (5-chloro-8-quinolinoxy) acetate (III-2), 4-allyloxybutyl (5-chloro-8-quinolineoxy) acetate (III-3) , 1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy) acetate (III-4), ethyl (5-chloro-8-quinolinoxy) acetate (III-5), methyl (5- Chloro-8-quinolineoxy) acetate (III-6), allyl (5-chloro-8-quinolineoxy) acetate (III-7), 2- (2-propylideneiminooxy) -1-ethyl (5- Chloro-8-quinolinoxy) acetate (III-8), 2-oxo-prop-1-yl (5-chloro-8-quinolinoxy) acetate (III-9), and related compounds;
[227] f) a compound of formula III wherein (5-chloro-8-quinolineoxy) malonic acid compound, ie, (R ¹⁹ ) _{n '} is 5-Cl, R ²⁰ is OR ²⁴ and T is -CH (COO-alkyl)- , Preferably compound diethyl (5-chloro-8-quinolineoxy) malonate, diallyl (5-chloro-8-quinolineoxy) malonate, methyl ethyl (5-chloro-8-quinolineoxy) malonate, And related compounds as described in EP-A 0 582 198;
[228] g) dichloroacetamide-based compounds, ie compounds of formula IV, preferably
[229] N, N-diallyl-2,2-dichloroacetamide (dichloramide, US-A 4,137,070),
[230] 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor, EP 0 149 974),
[231] N1, N2-diallyl-N2-dichloroacetylglycinamide (DKA-24, HU 2143821),
[232] 4-dichloroacetyl-1-oxa-4-aza-spiro [4,5] decane (AD-67),
[233] 2,2-dichloro-N- (1,3-dioxolan-2-ylmethyl) -N- (2-propenyl) acetamide (PPG-1292),
[234] 3-dichloroacetyl-2,2,5-trimethyloxazolidine,
[235] 3-dichloroacetyl-2,2-dimethyl-5-phenyloxazolidine,
[236] 3-dichloroacetyl-2,2-dimethyl-5- (2-thienyl) oxazolidine,
[237] 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyloxazolidine (furylazole, MON 13900),
[238] 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo [1,2-a] pyrimidin-6 (2H) -one (dicyclonon, BAS 145138);
[239] h) compounds of the group B (b), preferably
[240] 1,8-naphthalene anhydride,
[241] Methyl diphenylmethoxy acetate,
[242] Cyanomethoxyimino (phenyl) acetonitrile (thiomethynyl),
[243] 1,3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile (oxabetrinyl),
[244] 4'-chloro-2,2,2-trifluoroacetophenone O-1,3-dioxolan-2-ylmethyloxime (fluxopenim),
[245] 4,6-dichloro-2-phenylpyrimidine (fenchlorim),
[246] Benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole),
[247] 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),
[248] N- (4-methylphenyl) -N '-(1-methyl-1-phenylethyl) urea (dimron),
[249] 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
[250] 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea,
[251] 1- [4- (N-4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea,
[252] 1- [4- (N-naphthoylsulfamoyl) phenyl] -3,3-dimethylurea,
[253] (2,4-dichlorophenoxy) acetic acid (2,4-D),
[254] (4-chlorophenoxy) acetic acid,
[255] (R, S) -2- (4-chloro-o-tolyloxy) propionic acid (mecoprop),
[256] 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB),
[257] (4-chloro-o-tolyloxy) acetic acid (MCPA),
[258] 4- (4-chloro-o-tolyloxy) butyric acid,
[259] 4- (4-chlorophenoxy) butyric acid,
[260] 3,6-dichloro-2-methoxybenzoic acid (dicamba),
[261] 1- (ethoxycarbonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor) and salts and esters thereof, preferably (C ₁ -C ₈ ).
[262] In addition, R ³⁰ is hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₃ -C ₆ ) -cycloalkyl, furanyl or thienyl, wherein the four radicals mentioned last are each unsubstituted or halogen, And substituted with one or more substituents selected from the group consisting of (C ₁ -C ₄ ) -alkoxy, halo- (C ₁ -C ₆ ) -alkoxy and (C ₁ -C ₄ ) -alkylthio, , and (C ₁ -C ₄₎ - alkyl or (C ₁ -C ₄₎ - alkyl substituted by halo;
[263] R ³¹ is hydrogen;
[264] R ³² is halogen, halo- (C ₁ -C ₄ ) -alkyl, halo- (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, ( C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkoxycarbonyl or (C ₁ -C ₄ ) -alkylcarbonyl, preferably (C ₁ like halogen, trifluoromethyl -C ₄ ) -halogen, (C ₁ -C ₄ ) -alkoxy, halo- (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkoxycarbonyl or (C ₁ -C ₄ ) -alkyl Sulfonyl;
[265] R ³³ is hydrogen;
[266] R ³⁴ is halogen, (C ₁ -C ₄ ) -alkyl, halo- (C ₁ -C ₄ ) -alkyl, halo- (C ₁ -C ₄ ) -alkoxy, (C ₃ -C ₆ ) -cycloalkyl, Phenyl, (C ₁ -C ₄ ) -alkoxy, cyano, (C ₁ -C ₄ ) -alkylthio, (C ₁ -C ₄ ) -alkylsulfinyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄₎ - alkoxycarbonyl or (C ₁ -C ₄₎ - alkyl-carbonyl, preferably halogen, (C ₁ -C ₄₎ - alkyl, such as methyl, trifluoromethyl (C ₁ - C ₄ ) -haloalkyl, halo- (C ₁ -C ₄ )-
[267] Halogen, (C ₁ -C ₄ ) -alkoxy and (C ₁ -C ₄ ) -alkylthio;
[268] n is 0, 1 or 2;
[269] Preference is also given to compounds of the formula V wherein t is 1 or 2 and salts thereof.
[270] Moreover, X ³ is CH;
[271] R ³⁵ is hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₃ -C ₆ ) -cycloalkyl, (C ₂ -C ₆ ) -alkenyl, (C ₅ -C ₆ ) -cycloalkenyl, phenyl Or 3-6 membered heterocyclyl having up to 3 heteroatoms selected from the group consisting of N, O and S, and the last six radicals mentioned are halogen, (C ₁ -C ₆ ) -alkoxy, (C ₁ -C ₆ ) -haloalkoxy, (C ₁ -C ₂ ) -alkylsulfinyl, (C ₁ -C ₂ ) -alkylsulfonyl, (C ₃ -C ₆ ) -cycloalkyl, (C _1- C ₄₎ - alkoxycarbonyl, (C ₁ -C ₄₎ - alkyl carbonyl and optionally substituted from the group consisting of carbonyl, and phenyl with one or more same or different substituents selected, in the case of cyclic radicals include, also (C ₁ - Optionally substituted with C ₄ ) -alkyl and (C ₁ -C ₄ ) -haloalkyl;
[272] R ³⁶ is hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₂ -C ₆ ) -alkenyl or (C ₂ -C ₆ ) -alkynyl, and the last three radicals mentioned are halogen, hydroxyl Optionally substituted with one or more identical or different substituents selected from the group consisting of (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy and (C ₁ -C ₄ ) -alkylthio;
[273] R ³⁷ is the same or different and is halogen, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -haloalkoxy, nitro, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -Alkoxy, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkoxycarbonyl or (C ₁ -C ₄ ) -alkylcarbonyl;
[274] R ³⁸ is hydrogen;
[275] R ³⁹ is the same or different and is halogen, nitro, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -haloalkoxy, (C ₃ -C ₆ ) -Cycloalkyl, phenyl, (C ₁ -C ₄ ) -alkoxy, cyano, (C ₁ -C ₄ ) -alkylthio, (C ₁ -C ₄ ) -alkylsulfinyl, (C ₁ -C ₄ ) -Alkylsulfonyl, (C ₁ -C ₄ ) -alkoxycarbonyl or (C ₁ -C ₄ ) -alkylcarbonyl;
[276] s is 0, 1 or 2;
[277] Preference is given to emollients of formula VI, wherein o is 1 or 2.
[278] The following subgroups are particularly preferred among the emollients of formula VII:
[279] R ⁴⁸ and R ⁴⁹ are hydrogen, (C ₁ -C ₈ ) -alkyl, phenyl, phenyl- (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₈ )- Alkyl, (C ₃ -C ₆ ) -alkenyl or (C ₃ -C ₆ ) -alkynyl, wherein the phenyl ring is F, Cl, Br, NO ₂ , CN, OCH ₃ , (C ₁ -C ₄ ) Compounds capable of being substituted by -alkyl or CH ₃ -SO ₂ ;
[280] R ^g is H;
[281] A is YR ^h ;
[282] A compound in which E is oxygen;
[283] Q ¹ is CR ₂ ⁴⁷ ;
[284] A compound in which R ⁴⁷ is hydrogen;
[285] m ″ is 1 and E is oxygen or sulfur;
[286] m "is 0; and
[287] R ⁴⁰ , R ⁴¹ , R ⁴² , R ⁴³ and R ⁴⁴ are in each case hydrogen, E is oxygen, Q ¹ is CR ₂ ⁴⁷ , A is YR ^h and m ″ is 1, in particular R ⁴⁷ is Hydrogen, R ^b is CH ₃ and Y is oxygen; Q ¹ is CR ₂ ⁴⁷ and m ″ is 0, in particular R ⁴⁴ and R ⁴⁷ are hydrogen and A is YR ^{h where} R ^b is preferably methyl And Y is preferably oxygen).
[288] Preferred groups of herbicides of formula (I) are shown in Tables 1-4 below. In these tables, the abbreviations used are as follows:
[289] c-Pr = cyclopropyl Bz = benzoyl
[290] Et = ethyl Me = methyl
[291] Ph = phenyl
[292]
[293]
[294]
[295]
[296]
[297]
[298]
[299] Relaxers (detoxifiers) of Formulas II to VII and compounds of group (b), for example those mentioned above in groups a) to h), are crops that are useful plants without substantially affecting the efficacy of herbicidally active substances. The use of the herbicidally active substance of formula (I) may reduce or prevent phytotoxic effects that may occur. This significantly expands the field of application of conventional crop protection products, to crops such as wheat, barley, corn, and rice, which have been so far impossible or limited, that is to say used only in low proportions or in a limited range. Expand
[300] The herbicidal active substance and the above mentioned emollients may be applied together (in a pre-prepared mixture or by a tank mixing method) or may be applied continuously in any desired order. The weight ratio of emollient: herbicidal active substance may vary within wide limits and is preferably from 1: 100 to 100: 1, in particular from 1:10 to 10: 1. In each case the optimum amount of herbicidal active substance and laxative agent may vary depending on the type of herbicidal active substance used or the laxative agent used and the type of useful crop to be treated and in each individual case by simple and routine preliminary experiments. It can also be determined.
[301] The main fields for application to mixtures according to the invention are, in particular, corn and cereal crops (for example wheat, rye, barley, oats), rice, sugar cane as well as cotton and soybeans, preferably cereals, rice and It's corn.
[302] By virtue of their properties, the emollients used according to the invention can be used for pretreatment of the seeds of crop plants (seed dressings) or introduced into seed furrows before sowing or applied together with herbicides before or after germination of the plants. . Pre-emergence pretreatment includes treatment of the tilled area before sowing and treatment of the cultivated area in which the seed is planted, as well as the treatment of the non- germinated cultivated area. It is preferred to apply it in combination with herbicides. For this purpose, tank mixtures or previously prepared mixtures can be used.
[303] The rate of application of the laxatives required may vary within wide limits by the guidelines and the herbicidal active materials used and are generally from 0.001 to 5 kg, preferably from 0.005 to 0.5 kg of active material per hectare.
[304] Therefore, the present invention also relates to a method for protecting crop plants from the phytotoxic side effects of herbicides of formula (I), which is a detoxifying amount of a compound of formula (II), (III), (IV), (V), (VI), (VII) and / or ((b Applying to the plant, the seed or the cultivated region of the plant before, after or simultaneously with the application of the herbicidal active substance A of formula (I).
[305] In addition, the herbicide / emollient mixtures according to the invention can be used to control harmful plants in known or ever developed genetically engineered crops. In principle, transformed plants are characterized by particularly advantageous properties, for example, resistance to certain crop protection agents, plant diseases or pathogens that cause certain insects or plant diseases such as microorganisms such as fungi, bacteria or viruses. It is erased. Other specific properties relate to the harvested material, for example in amount, quality, storage properties, composition and specific ingredients. As such, transformed plants with increased starch content or modified starch quality or transformed plants in which the harvested material has a different fatty acid composition are known.
[306] The use of the mixtures according to the invention is, for example, wheat, barley, rye, oats, grasses, rice, cassava and corn or sugar cane, cotton, soybeans, rapeseed oil seeds, potatoes, tomatoes, peas. And economically important for transforming crops and ancillaries of useful plants, such as and other kinds of plants.
[307] When applying the mixtures according to the invention to transformed crops, the effects on harmful plants observed in other crops can be altered or in particular that are specific to the application in such transformed crops, for example, to be modulated. It is often accompanied by broadened weed ranges, altered application rates that can be used, preferably good compatibility with herbicides that are resistant to transformed crops, and altered growth and yield of transformed crop plants.
[308] The present invention therefore relates to the use of the mixtures according to the invention for the control of harmful plants in transgenic crop plants.
[309] Mitigators of Formulas III-VII and (b) and mixtures with one or more of the above-mentioned herbicidal active substances of Formula II may be formulated in a variety of ways by specified biological and / or physicochemical parameters.
[310] Examples of possible suitable formulations are as follows:
[311] Wettable powders (WP), emulsifiable concentrates (EC), water-soluble powders (SP), water-soluble concentrates (SL), water-in-oil emulsions and water Concentrated emulsions (BW), such as oil-based emulsions, dispersible solutions or emulsions, capsule suspensions (CS), oil- or water-based dispersions (SC), and suspo-emulsions ( suspoemulsion, suspension concentrates, dust (DP), oil-miscible solutions (OL), seed treatment products, granules in the form of microgranules, spray granules, coated granules and absorption Granules, granules for application or spraying, water-soluble granules (SG), water-dispersible granules (WG), ULV formulations, microcapsules and waxes.
[312] These individual formulation types are described, eg, in Winnacker and Kuchler (Chemische Technologies, Chemical Engineering, Volume 7, C. Hauser Verlag Munich, 4 ^th Edtion 1986); Wade van Valkenburg, Pesticide Formulations, Marcel Dekker NY, 1973; K. Martens, Spray Drying Handbook, 3 ^rd Ed. 1979, G. Goodwin Ltd. London is generally known and described.
[313] Formulation aids that may be required, such as inert materials, surfactants, solvents and other additives, are described, for example, in Handkins of Insecticide Dust Diluents and Carriers, 2 ^nd Ed., Dardland Books ], Caldwell, NJ, Olphen, HV, Introduction to Clay Colloid Chemistry, 2 ^nd Ed., J. Wiley & Sons, NY, Marsden, C. Solvents Guide, 2 ^nd Ed., Interscience, NY 1963; McCutcheon, Detergents and Emulsifiers Annual, MC Publ. Corp., Ridgewood NJ; Sisley and Wood, Encyclopedia of Surface Active Agents, Chem. Publ. Co. Inc., NY 1964; Schonfeldt, Glenzflachenaktive Athylenoxidaddukte, Surface-active Ethylene Oxide Adducts, Wiss. Verlagsgesell, Stuttgart 1976; Known and described in Winnaker and Kuhler (Chemische Technologie, Chemical Engineering, Volume 7, C. Hauser Verlag Munich, 4 ^th Edition 1986).
[314] Based on these formulations, other substances that can act as crop protection agents, such as insecticides, mite removers, herbicides, fungicides, and emollients, chemical fertilizers and / or growth regulators, for example in the form of previously prepared mixtures or tank mixtures; It is possible to prepare mixtures of these.
[315] Wettable powders are preparations that are homogeneously dispersible in water and, in addition to the active substance, also include ionic and / or nonionic surfactants (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxy Ethylated fatty alcohols, polyoxyethylated fatty acid amines, fatty alcohol alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonates, sodium 2,2'-dinaphthylmethane-6,6 '-Disulfonate, sodium dibutylnaphthalene-sulfonate or other sodium oleoylmethyltautinate is added to the diluent or inert material to contain it. Herbicidal active materials for producing wettable powders are ground finely in conventional equipment such as, for example, hammer mills, blower mills and air-jet mills, They are mixed simultaneously or sequentially with the formulation aid.
[316] Emulsifiable concentrates may, for example, contain the active materials in organic solvents such as butanol, cyclohexanone, dimethylformamide, xylene or other high boiling saturated or unsaturated aliphatic or aromatic materials, or one or more ionic and / or Or by dissolving in a mixture of a nonionic surfactant (emulsifier) and an organic solvent. Examples of materials that can be used as emulsifiers are calcium (C ₆ -C ₁₈ ) -alkylarylsulfonates, such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, (C ₂ -C ₁₈ ) -alkyl Polyoxyethylene sorbitan esters such as arylpolyglycol ethers, fatty acid alcohol polyglycol ethers, propylene oxide / ethylene oxide concentrates, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene sorbitan fatty acid esters do.
[317] Dust is generally a finely divided solid substance of the active substance, for example obtained by grinding natural clays or diatomaceous earth, such as talc, kaolin, bentonite and pyrophyllite.
[318] Suspension concentrates may be aqueous or oily. These can be prepared by wet grinding using commercially available bead mills with or without surfactants, for example as already mentioned above for other formulation types.
[319] Emulsions, for example oil-in-water emulsions (EW), employ, for example, aqueous organic solvents in the presence or absence of the aforementioned surfactants used in the case of other formulation types. Can be produced by a stirrer, a colloid mill and / or an idle mixer.
[320] Granules are absorbent and granulated active material concentrates in granulated inert materials or sand, kaolinite, or granulated active material concentrates with the aid of binders such as polyvinyl alcohol, sodium polyacrylate or other mineral oils. It can be prepared by applying to the surface of a carrier such as an inert material. In addition, suitable active substances can be granulated in a manner customary for the preparation of chemical fertilizer granules, with mixtures with chemical fertilizers being preferred. In principle, water dispersible granules are produced by conventional methods such as spray drying, fluidized bed granulation, disc granulation, mixing with a high speed mixer and extrusion without solid inert materials. To prepare disk fluidized bed extruders and spray granules, see, for example, Spray-Drying Handbook, 3 ^rd ed. 1979, G. Goodwin Ltd., London; Browning, JE, Aglomeration, Chemical and Engineering 1967, pages 147 et seq .; Perry's Chemical Engineer's Handbook, 5 ^th Ed., McGraw-Hill, New York 1973, pp. 8-57.
[321] For a more detailed description of the formulation of crop protection products, see Kedman, GC, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and Freyer. , JD), Evans, SA, Weed Control Handbook, 5 ^th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
[322] In principle, agrochemical formulations may contain 0.1 to 99% by weight, in particular 0.1, of a herbicide / detoxifier mixture of the active substances of formulas II to VII and / or (b) or of the active substances of formula I and formulas II to VII and / or (b). To 95% by weight, from 1 to 99.9% by weight of solid or liquid additives, in particular from 5 to 99.8% by weight and from 0 to 25% by weight of surfactant, in particular from 0.1 to 25% by weight.
[323] In wettable powders, the active substance concentration is, for example, approximately 10 to 90% by weight, with the remainder being 100% by weight consisting of conventional formulation ingredients. For emulsifiable concentrates, the active substance concentration is approximately 1 to 80% by weight. The formulations in the form of dust consist of approximately 1 to 20% by weight of active material and the sprayable solution consists of approximately 0.2 to 20% by weight of active material. For granules, such as water dispersible granules, the active substance content depends in part on whether the active compound is in liquid or solid form. The active substance content of the water dispersible granules is in principle 10 to 90% by weight.
[324] In addition to these, the active materials of the abovementioned formulations are suitably, in each case, conventional adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors. And pH and viscosity modifiers.
[325] Ingredients that can be used for the mixtures according to the invention in mixed formulations or tank mixtures are described, for example, in Weed Research 26, 441-445 (1986) or The Pesticide Manual, 10 ^th edition, The British Crop Protection Council, 1994, and known active materials as described in the references cited herein. Herbicides known in the literature and which can be mixed with the mixtures according to the invention are, for example, the following active substances [NOTE: Conventional names of compounds according to the International Organization for Standardization (ISO) or One of the two chemical names, suitably given with the usual code number]:
[326] Acetochlor; Acifluorfen; Aclonifen; AKH 7088, ie [[[1- [5- [2-chloro-4- (trifluoromethyl) -phenoxy] -2-nitrophenyl] -2-methoxyethylidene] -amino] oxy] Acetic acid and its methyl ester; Alachlor; Alkoxydim; Amethrin; Amidosulfuron; Amitrol; AMS, ie ammonium sulfamate; Anilofoss; Asulam; Atrazine; Azaphenidine (DPX-R6447), azimsulfuron (DPX-A8947); Aziprotrine; Barban; BAS 516H, ie 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; Benazolin; Benfluranine; Benfuresate; Bensulfuron-methyl; Bensulfide; Ventazone; Benzofluor; Benzoylprop-ethyl; Benzthiazuron; Bialaphos; Biphenox; Bispyribak-sodium (KIH-2023), bromacil; Bromobutide; Bromophenoxime; Bromoxynil; Bromuron; Buminafoss; Auxiliary synon; Butachlor; Butamiforce; Butenachlor; Butidazole; Butralline; Butoxydimdim (ICI-0500); Butyrate; Carpenstrol (CH-900); Carbetamid; Carpentrazone; CDAA, ie 2-chloro-N, N-di-2-propenylacetamide; CDEC, ie 2-chloroallyl diethyldithiocarbamate; Clomethoxyphene; Chloramben; Chloransullam-methyl (XDE-565), chlorazif-butyl, chlorbromuron; Chlorobufam; Chlorophenac; Chlorflurechol-methyl; Chlorida Zone; Chlorimuron-ethyl; Chlornitropen; Chlorotoluron; Chlorozuron; Chloropropame; Chlorosulfuron; Chlortal-dimethyl; Chlortiamide; Cinidon-ethyl, cinmethylline; Cynosulfuron; Cletodim; Clodinapope and ester derivatives thereof (eg, clodinapope-propargyl); Clomazone; clomeprop; Cloproxidim; Clopyralide; Cumyluron (JC 940); Cyanazine; Cycloate; Cyclosulfamuron (AC 014); Cyclooxydim; Cyclone; Sihalofop and its ester derivatives (eg butyl ester, DEH-112); Cyperquat; Cyprazine; Cyprazole; 2,4-DB; Dalaphone; Desmedipham; Desmethrin; Di-acrylates; Dicamba; Diclobenyl; Dichlorprop; Esters thereof such as diclopov and diclofo-methyl; Diclosullam (XDE-564), dietatyl; Diphenoxalon; Defenzoquat; Diflufenican; Diflufenzopyr-Sodium (SAN-835H), Dimefuron; Dimetachlor; Dimethamethrin; Dimethenamid (SAN-582H); Dimethazone, methyl 5- (4,6-dimethylpyrimidin-2-yl-carbamoylsulfamoyl) -1- (2-pyridyl) -pyrazole-4-carb-oxylate (NC-330); Triazoflam (IDH-1105), clomazone; Dimethipine; Dimetrasulfuron, dinitramine; Dinosev; Dinoterb; Diphenamide; Dipropetrin; Diquat; Dithiopyr; Diuron; DNOC; Egglinazine-ethyl; EL 177, ie 5-cyano-1- (1,1-dimethylethyl) -N-methyl-1H-pyrazole-4-carboxamide; Endortal; Epoprodan (MK-243), EPTC; Esprocarb; Etaflularine; Etamethsulfuron-methyl; Etidimuron; Ethiazine; Etofumesate; F5231, ie, N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl]- Phenyl] -ethanesulfone-amide; Ethoxyphene and esters thereof (eg, ethyl ester, HN-252); Ethoxysulfuron (EP 342569), etobenzanide (HW 52); 3- (4-ethoxy-6-ethyl-1,3,5-triazin-2-yl) -1- (2,3-dihydro-1,1-dioxo-2-methylbenzo [b] Thiophene-7-sulfonyl) urea (EP-A 079 683); 3- (4-ethyl-6-methoxy-1,3,5-triazin-2-yl) -1- (2,3-dihydro-1,1-dioxo-2-methylbenzo [b] Thiophene-7-sulfonyl) urea (EP-A 079 683);
[327] Phenoprop; Phenoxane, phenoxaprop and phenoxaprop-P and esters thereof such as phenoxaprop-P-ethyl and phenoxaprop-ethyl; Phenoxydim; Penuron; Frramprop-methyl; Plazasulfuron; Fluonacet (BAY-FOE-5043), fluazifop and fluazifop-P, florasullam (DE-570) and esters thereof, for example fluazifop-butyl and fluazifop-P-butyl ; Fluchlorin; Flumetsulam; Flumeturon; Flumichlorac and esters thereof (eg, pentyl ester, S-23031); Flumioxazine (S-482); Flumipropine; Flupoxam (KNW-739); Fluorodiphene; Fluoroglycopene-ethyl; Flupropacyl (UBIC-4243); Sodium flupysulfuron-methyl (DPX-KE459), flulidone; Flulochloridone; Fluoroxypyr; Flutamone; Fluthiacet-methyl (KIH-9201), pomesafen; Fosamine; Furyloxyphene; Glufosinate; Glyphosate; Halosafen; Halosulfuron and esters thereof (eg, methyl ester, NC-319); Haloxope and esters thereof; Haloxif-P (= R-haloxopf) and esters thereof; Hexazinone; Imazamethabenz-methyl; Imazamox (AC-299263), imazaphyr; Salts such as imazaquin and ammonium salts; Imazetametapyr; Imazetapyr; Imazosulfuron; Iodosulfuron (methyl 4-iodo-2- [3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) ureidosulfonyl] benzoate, sodium salt, WO 92 / 13845); Ioxynyl; Isocarbamide; Isoprophalin; Isoproturon; Isourone; Isoxaben; Isoxatipyrup; Carbutylate; Lactofen; Lenacil; Linuron; MCPA; MCPB; Mecoprop; Mefenacet; Mefluidide; Metamitrone; Metazachlor; Metabenzthiazuron; Metam; Metazole; Methoxyphenone; Methyldimron; Metabenzuron, methyl2- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonyl] -4-methanesulfonamidomethylbenzoate (WO 95/10507); Metobenzuron; Metobromuron; Metolachlor; S-metolachlor, metosolam (XRD 511); Methosuron; Metrizine; Metsulfuron-methyl; MH; Molinate; Monalids; Monocarbamide dihydrogensulfate; Monolinuron; Monuron; MT 128, ie 6-chloro-N- (3-chloro-2-propenyl) -5-methyl-N-phenyl-3-pyridazinamine;
[328] MT 5950, ie, N- [3-chloro-4- (1-methylethyl) -phenyl] -2-methylpentanamide; N, N-dimethyl-2- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonyl] -4-formyl-amino-benzamide (WO 95/01344); Naproanilide; Napropamide; Naphthalam; NC 310, ie 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole; Neburon; Nicosulfuron; Nipyraclofen; Nitraline; Nitrofen; Nitrofluorfen; Norflurazone; Orbencarb; Oryzalin; Oxadiargyl (RP-020630); Oxadione; Oxaziclomepon (MY-100), oxyfluorfen; Oxasulfuron (CGA-277476), paraquat; Pebulate; Pendimethalin; Pentoxazone (KPP-314), perfluidone; Phenisofam; Penmedipham; Picloram; Piperophosph; Pyributycarb; Pyrifenof-butyl; Pretyl achlor; Primisulfuron-methyl; Prosazine; Prodiamine; Propluramine; Proglyazine-ethyl; Promethone; Promethrin; Propachlor; Propanyl; Propaquizapov and esters thereof; Propazine; Profam; Propisochlor; Propizide; Prosulfurin; Prosulfocarb; Prosulfuron (CGA-152005); Prinachlor; Pyraflufen-ethyl (ET-751), pyrazone; Pyrazosulfuron-ethyl; Pyrazoxifen; Pyribenzoxime, pyridate; Pyriminobac-methyl (KIH-6127), pyrithiobak (KIH-2031); Pyroxofop and its esters (eg, propargyl esters); Quinclorac; Quinmerac; Quinopopes and ester derivatives thereof, quizolopope and quizolopop-P and ester derivatives thereof, such as quizalopop-ethyl; Quizolopov-P-tefuryl and -ethyl; Lenliduron; Rimsulfuron (DPX-E 9636); S275, ie 2- [4-chloro-2-fluoro-5- (2-propynyloxy) -phenyl] -4,5,6,7-tetrahydro-2H-indazole; Secbumethone; Cetoxydim; Siduron; Simazine; Simethrin; SN 106279, ie 2-[[7- [2-chloro-4- (trifluoro-methyl) -phenoxy] -2-naphthalenyl] -oxy] -propanoic acid and methyl esters thereof; Sulfentrazone (FMC-97285, F-6285); Sulfazurism; Sulfomethuron-methyl; Sulfosate (ICI-A0224); Sulfosulfuron (MON-37500), TCA; Tebutam (GCP-5544); Tebutiuuron; Tefraloxydim (BAS-620H), terbasil; Terbucarb; Terbuchlor; Terbumetone; Terbutylazine; Terbutryn; TFH 450, ie, N, N-diethyl-3 [(2-ethyl-6-methylphenyl) -sulfonyl] -1H-1,2,4-triazole-1-carboxamide; Tenylchlor (NSK-850); Triazafluron; Thiazopyr (Mon-13200); Tidiazimine (SN-124085); Thifensulfuron-methyl; Thiobencarb; Thiocarbazyl; Trakcocksidim; Tri-acrylates; Triasulfuron; Triazphenamide; Tribenuron-methyl; Triclopyr; Tridiphane; Triethazine; Trifluurine; Triflusulfuron and esters (eg, methyl esters, DPX-66037); Trimethuron; Tcitodef; Benolate; WL 110547, ie 5-phenoxy-1- [3- (trifluoromethyl) -phenyl] -1 H-tetrazole; UBH-509; D-489; LS 82-556; KPP-300; KPP-421, MT-146, NC-324; KH-218; DPX-N8189; DOWCO-535; DK-8910; V-53482; PP-600; MBH-001.
[329] Formulations in the form commercially available for use are diluted in a conventional manner, if necessary, for example, in the case of wettable powders, emulsifiable concentrates, dispersions and water dispersible granules in conventional manner. . Dust, soil granules, sparge granules and dispersible solutions are usually not further diluted with other inert materials prior to use.
[330] The essential application rates of the herbicides of formula I vary, in particular, depending on external conditions such as temperature, humidity and the nature of the herbicide used. This can vary within wide limits, for example 0.001 to 10 kg / ha or more of herbicide, but preferably 0.005 to 5 kg / ha.
[331] The following examples are intended to illustrate the invention.
[332] A. Formulation Examples
[333] a) talc with 10 parts by weight of an active substance mixture of a compound of formulas II to VII and / or group B (b) or a herbicidal active substance of formula I and an emollient of formulas II to VII and / or group (b) and an inert substance 90 Dust is obtained by mixing parts by weight and subdividing the mixture in a hammer mill.
[334] b) 25 parts by weight of an active substance mixture of a compound of formula II to VII and / or group B (b) or a herbicidal active substance of formula I and a laxative of formula II to VII and / or group B (b), kaolin as an inert substance 64 parts by weight of quartz-containing, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleylmethyl tautinate as a humectant and dispersant, and easily crushed the mixture in a pinned-disk mill To obtain a dispersible and wettable powder.
[335] c) 20 parts by weight of an active substance mixture of a compound of formulas II to VII and B (b) or a herbicidal active substance of formula I and a relaxant of formulas II to VII and / or B (b), an alkylphenol polyglycol ether [ Triton® X 207] 6 parts by weight, 3 parts by weight of isotridecanol polyglycol ether (8 EO) and paraffinic mineral oil (the boiling range is, for example, greater than approximately 255 to 277 ° C). 71 parts by weight are mixed and the mixture is ground finely in a ballmill smaller than 5 microns to give a concentrate that is readily dispersible or susceptible in water.
[336] d) 15 parts by weight of a herbicidal active material of the compound of formulas II to VII and / or group B (b) or of formula I and a herbicidal active material of the emollients of formulas II to VII and / or group B (b), cyclohexa with solvent An emulsifiable concentrate is obtained from 75 parts by weight of paddy and 10 parts by weight of nonylphenol oxetylated with an emulsifier.
[337] e) 75 parts by weight of a herbicidally active mixture of a compound of formula II to VII and / or group B (b) or a compound of formula I and a compound of formula II to VII and / or group B (b), calcium lignosulfo 10 parts by weight of nate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin and mixed the powder in a pinned disk mill and disperse the water with granulation liquid Obtain acidic granules.
[338] f) 25 parts by weight of a herbicidally active mixture of a compound of formulas II to VII and / or group B (b) or a herbicidally active substance of formula I and an emollient of formulas II to VII and / or group B (b), sodium 2,2 5 parts by weight of '-dinaphthylmethane-6,6'-disulfonate, 2 parts by weight of sodium oleoylmethyl tautinate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of the colloid mill The water dispersible granules are obtained by homogenizing and pre-dividing the mixture and then grinding the mixture in a bead mill, making dust and drying the resulting suspension in the spray tower by a single material nozzle.
[339] Biological Example
[340] 1. Greenhouse Experiment
[341] 1.1 Before Germination
[342] Seeds or underground diameters of monocot and dicotyledonous and useful plants are placed in sandy loam and covered with soil in a 9-13 cm diameter jar. Running, for the rice test, harmful plants that are not needed for the crops of rice plants and useful plants are allowed to grow in water-soaked soil. Various doses of herbicides and emollients formulated as emulsifiable concentrates or dusts are applied to the surface of the soil in the form of aqueous dispersions or suspensions or emulsions at rates of 300-800 L water / ha (converted), or in rice tests. In case, pour into irrigation water. The jar is then kept in a greenhouse under optimal conditions to allow the plant to grow. Three to four weeks after treatment, the losses to useful and harmful plants are visually scored. The loss is expressed as a percentage compared to the untreated control.
[343] The test results are summarized in Tables 5 and 6:
[344] Application rate: 200-400 g a.i./ha; Herbicides 1-1; corn Herbicides / EmollientsApplication rate [g a.i./ha]Phytotoxicity to Corn [%] Variant FelixVariety Dea Herbicides 1-14008580 Herbicides 1-13008585 Herbicides 1-12007878 Herbicide 1-1 / emollient b-1300 + 3005040 Herbicide 1-1 / emollient c-1300 + 3007055 Herbicide 1-1 / emollient c-3300 + 3004545 Herbicide 1-1 / emollient c-7300 + 3003525 Herbicide 1-1 / emollient c-10300 + 3004038 a.i. = active ingredient
[345] Application rate: 100-300 g a.i./ha; Herbicides 1-1; Action on vegetational weeds / leafy weed Herbicides / EmollientsApplication rate [g a.i./ha]Action[%] ECHCGSETVIABUTHPHBPU Herbicides 1-1300991009890 Herbicide 1-1 / emollient b-1300 + 300991009990 Herbicide 1-1 / emollient c-1300 + 300991009885
[346] Herbicides 1-1: Herbicides Example No. 1.1 (Table 1)
[347] Emollient b-1: 1- [4- (2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea
[348] Emollient c-1: 2-methoxy-N- [4- (2-methoxybenzoylsulfamoyl) phenyl] -acetamide
[349] Emollient c-3: N- [4- (2-methoxybenzoylsulfamoyl) phenyl] -cyclobutane-carboxamide
[350] Emollient c-7: N- [4- (2-chlorobenzoylsulfamoyl) phenyl] -cyclopropane-carboxamide
[351] Emollient c-10; N- [4- (2-trifluoromethoxybenzoylsulfamoyl) phenyl] -cyclo-propanecarboxamide
[352] ECHCG ( Echinocloa crus galli ): Echinocloe crous galli
[353] ABUTH ( Abutilon theophrasti ): Abutylon Teoplasty
[354] Pharbitis purpureum (PHBPU): parvitis purpurum
[355] SETVI ( Setaria viridis ): Setaria viridis
[356] 1.2 After Germination
[357] Seeds or underground diameters of monocot and dicotyledonous and useful plants are placed in sandy loam and covered with soil in a 9-13 cm diameter jar. Running, for the rice test, harmful plants that are not needed for the crops of rice plants and useful plants are allowed to grow in water-soaked soil. At the three-leaf stage, i.e. approximately three weeks after the start of the experiment, various doses of herbicides and emollients formulated as emulsifiable concentrates or dusts were applied at an aqueous dispersion or suspension at a rate of 300-800 L water / ha (converted). Or applied to the surface of the soil in the form of an emulsion, or, in the case of rice testing, poured into irrigation water. The jar is then kept in a greenhouse under optimal conditions to allow the plant to grow. In order to allow plants to grow, the jars are kept under optimal conditions in the greenhouse. Losses for useful and harmful plants are visually scored two to three weeks after treatment. The test results are summarized in Tables 7-9:
[358] Application rate: 100-300 g a.i./ha; Herbicides 3-1; wheat Herbicides / EmollientsCapacity [kg a.i./ha]Loss [%] Wheat [Variety Ralle] Herbicides 3-130040 Herbicides 3-120035 Herbicides 3-110030 Herbicides 3-1 / Emollients II-9300 + 15010 Herbicides 3-1 / Emollients II-9200 + 1005 Herbicides 3-1 / Emollients II-9100 + 500 Herbicides 3-230045 Herbicides 3-220030 Herbicides 3-210030 Herbicides 3-2 / Emollients II-9300 + 30010 Herbicides 3-2 / Emollients II-9200 + 2000 Herbicides 3-2 / Emollients II-9100 + 1000
[359] Application rate: 100-300 g a.i./ha; Herbicides 1-1; corn Herbicides / EmollientsApplication rate [g a.i./ha]Phytotoxicity to Corn [%] Variant FelixVariant D Herbicides 1-11001315 Herbicides 1-13004530 Herbicide 1-1 / emollient b-1300 + 300133 Herbicide 1-1 / emollient c-1300 + 300518 Herbicide 1-1 / Emollient II-9300 + 3001020
[360] Application rate: 500 g a.i./ha; Herbicides 3-1; corn Herbicides / EmollientsApplication rate [g a.i./ha]Phytotoxicity to Corn [%] Variant FelixVariant D Herbicides 3-15002315 Herbicide 3-1 / emollient c-1500 + 500100 Herbicides 3-1 / Emollients II-9500 + 50050 Herbicide 1-1 / Emollient II-9500 + 100000
[361] Herbicides 1-1: Herbicides Example No. 1-1 (Table 1)
[362] Herbicide 3-1: Herbicide Example No. 3-1 (Table 3)
[363] Herbicides 3-2: Herbicides Example No. 3-2 (Table 3)
[364] Emollient II-9: Ethyl 5,5-diphenyl-2-isoxazolin-3-carboxylate
[365] Emollient b-1: 1- [4- (2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea
[366] Emollient c-1: 2-methoxy-N- [4- (2-methoxybenzoylsulfamoyl) phenyl] -acetamide
[367] 2. Field experiment
[368] Field experiments are carried out in small compartments of 8 to 10 m ² , with each experiment being duplicated two to four times. After sowing the crop plants, the test formulation is applied before germination or at the 2- or 6-leaf stage using a plot sprayer. The nebulizer volume is 100-300 L water / ha and is applied by a flat-jet nozzle at a pressure of 2-3 bar. Visually scored and evaluated. The effect on crop plants or broadleaf weeds / vegetation chopsticks is assessed using percentage ranges (0-100%) compared to the sections of untreated controls. The plants are scored three to four times at intervals approximately 14, 28 and 42 days after application. The results represent averages of two to four overlaps. In general, crop losses in the case of maize are acceptable up to approximately 15%. Preventive action against weeds should exhibit at least 60% efficacy. From sowing to the conclusion of the experiment, they are exposed to natural climatic conditions (rainfall, temperature, atmospheric humidity, solar radiation) as characteristic of the experimental site.
[369] The test results are summarized in Tables 10-13 below:
[370] Field experiment: applied at the 4-leaf stage, corn (after germination) Herbicides / EmollientsApplication rate [g a.i./ha]Phytotoxicity to Corn [%] 14 dat31 dat Herbicides 1-15003512 Herbicide 1-1 / Emollient II-9105 + 10070 Emollient II-910000 dat: date after processing
[371] Field Experiment: Applied in the 4-leaf Stage, Corn Herbicides / EmollientsApplication rate [g a.i./ha]Phytotoxicity to Corn [%] 14 dat42 dat Herbicides 1-1504218 Herbicide 1-1 / Emollient II-950 + 12082 Emollient II-912000
[372] Action on vegetation weeds / leafy weeds (after budding) Herbicides / EmollientsApplication rate [g a.i./ha]Action[%] corn Panicum minor Setaria faberi Abutilon theophrastis Herbicides 1-110535757572 Herbicide 1-1 / Emollient II-9105 + 1007728373 Emollient II-91000000
[373] Mixture with sulfonylureas (after germination) Herbicides / EmollientsApplication rate [g a.i./ha]Phytotoxicity to Corn [%] 14 dat42 dat Herbicides 1-1504218 Herbicide 2120137 Herbicides 1-1 + Herbicides 2 + Emollients II-950 + 120 + 120105 Emollient II-912000
[374] Herbicides 1-1: Herbicides Example No. 1-1 (Table 1)
[375] Herbicide 2: N, N-dimethyl-2- [3- (4,6-dimethoxypyrimidin-2-yl) ureido-sulfonyl] -4-formylaminobenzamide
[376] Emollient II-9: Ethyl 5,5-diphenyl-2-isoxazolin-3-carboxylate.

权利要求:
Claims (12)
[1" claim-type="Currently amended] A mixture of the following compounds A and B,
(a) in the compound of formula I, V is V1 or V4; The emollient is a compound of formula IV or 1,8-naphthalene anhydride, methyldiphenylmethoxyacetate, 2-dichloro-methyl-2-methyl-1,3-dioxolane, cyanomethoxyimino (phenyl) acetonitrile, 1,3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile, 4'-chloro-2,2,2-trifluoroacetophenone O-1,3-dioxolan-2-ylmethyloxime, 4 , 6-dichloro-2-phenylpyrimidine, benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate and 1-methylhexyl (5-chloro-8-quinolineoxy) Mixtures selected from the group consisting of acetates; or
(b) in the compound of formula I, V is V3 and R ⁶ is OH; The emollient is a compound of formula II wherein W is W1, W2, W3 or W4 and m 'is 1, T is unsubstituted or substituted with one or two (C ₁ -C ₄ ) -alkyl radicals (C ₁ -or C ₂ ) -alkanediyl chain compound of formula (III), compound of formula (IV), or 1,8-naphthalene anhydride, cyanomethoxyimino (phenyl) acetonitrile, oxabetrinyl, fluxopenime and flurazole Herbicidally active compositions which exclude mixtures which are compounds selected from the group:
A. A herbicidally active amount of at least one compound of formula (I):
Formula I

Where
V is a radical selected from the group consisting of the following formulas V1 to V4:
Formula V1

Formula V2

Formula V3

Formula V4

[Wherein the symbols and indices have the following meanings:
R is hydrogen, (C ₁ -C ₄ ) -alkoxycarbonyl, (C ₁ -C ₄ ) -haloalkoxycarbonyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkyl Sulfinyl, (C ₁ -C ₄ ) -alkylthio, COOH or cyano;
R ¹ is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl, (C ₃ -C ₈ ) -cycloalkyl, (C ₃ -C ₈ ) -cycloalkenyl, (C ₁ -C ₄ ) -alkyl- (C ₃ -C ₈ ) -cycloalkyl, (C ₃ -C ₇ ) -halocycloalkyl, (C ₁ -C ₄ ) -Alkylthio- (C ₃ -C ₈ ) -cycloalkyl, (C ₁ -C ₈ ) -haloalkyl or (C ₂ -C ₈ ) -haloalkenyl;
R ² is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -haloalkyl, halogen, (C ₁ -C ₄ ) -haloalkoxy, cyan No or nitro;
R ³ is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkylcarbonyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ )- Haloalkylsulfonyl, (C ₁ -C ₄ ) -alkyl-substituted or unsubstituted arylsulfonyl, (C ₁ -C ₄ ) -alkyl-substituted or unsubstituted arylcarbonyl- (C ₁ -C ₄ ) -alkyl or (C ₁ -C ₄ ) -alkyl-substituted or unsubstituted aryl- (C ₁ -C ₄ ) -alkyl;
R ⁴ is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl, (C ₁ -C ₄ ) -haloalkyl, phenyl or Benzyl;
R ⁵ is (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -Dialkoxy- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkylthio, halogen, substituted or unsubstituted aryl, tetrahydropyran-4-yl, tetrahydropyran-3-yl, Tetrahydrothiopyran-3-yl, 1-methylthiocyclopropyl or 2-ethylthiopropyl, or two radicals R ⁵ together are (C ₂ -C ₄ ) -alkylene;
R ⁶ is hydroxyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₈ ) -haloalkoxy, formyloxy, (C ₁ -C ₄ ) -alkylcarbonyloxy, (C ₁ -C ₄ ) -Alkylsulfonyloxy, (C ₁ -C ₄ ) -alkylthio, (C ₁ -C ₄ ) -haloalkylthio, arylthio, aryloxy, (C ₁ -C ₄ ) -alkylsulfinyl or (C _1- C ₄ ) -alkylsulfonyl;
R ⁷ is (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₃ -C ₈ ) -cycloalkyl, (C ₁ -C ₄ ) -alkyl- (C ₃ -C ₈ ) -cycloalkyl or (C ₃ -C ₈ ) -halocycloalkyl;
R ⁸ is cyano, (C ₁ -C ₄ ) -alkoxycarbonyl, (C ₁ -C ₄ ) -alkylcarbonyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ )- Alkylsulfinyl, (C ₁ -C ₄ ) -alkylthio, (C ₁ -C ₄ ) -alkylaminocarbonyl or (C ₁ -C ₄ ) -dialkylaminocarbonyl;
I is an integer from 0 to 6, and when I is 2 or more, the radicals R ⁵ may be the same or different from each other,
R ⁹ is the same or different and is nitro, amino, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl, halogen, (C _1- C ₄ ) -haloalkyl, (C ₂ -C ₄ ) -haloalkenyl, (C ₂ -C ₄ ) -haloalkynyl, (C ₁ -C ₄ ) -haloalkoxy, (C ₁ -C ₄ )- Haloalkylthio, (C ₁ -C ₄ ) -alkoxycarbonyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkylsulfinyl, (C ₁ -C ₄ ) -alkylthio , Arylsulfonyl, arylsulfinyl, arylthio, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ )- alkylthio - (C ₁ -C ₄₎ - alkoxy, (C ₁ -C ₄₎ - alkyl-carbonyl, (C ₁ -C ₄₎ - alkyl-amino sulfonyl, (C ₁ -C ₄₎ - dialkylamino sulfonic Phonyl, (C ₁ -C ₄ ) -alkylcarbamoyl, (C ₁ -C ₄ ) -dialkylcarbamoyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, phenoxy, Cyano, aryl, alkylamino or dialkylamino;
q is 0, 1, 2, 3 or 4; And
B. at least one safener in an amount of detoxifying effect selected from the group consisting of the following compounds a) to e):
a) a compound of formula (II)-(IV)
Formula II

Formula III

Formula IV

[Wherein the symbols and indices have the following meanings:
n 'is a natural number from 0 to 5;
T is a (C ₁ or C ₂ ) -alkanediyl chain unsubstituted or substituted by one or two (C ₁ -C ₄ ) -alkyl radicals or [(C ₁ -C ₃ ) -alkoxy] carbonyl;
W is a substitution selected from the group of partially unsaturated or aromatic five-membered heterocyclic rings having 1-3 hetero ring atoms of the N or O type, wherein the ring contains one or more N atoms and one or more O atoms Unsubstituted or substituted diatoms are heterocyclic radicals, preferably radicals selected from the group consisting of the formulas W1 to W4:
Formula W1

Formula W2

Formula W3

Formula W4

(Wherein
m 'is 0 or 1;
R ¹⁷ and R ¹⁹ are the same or different and are halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, nitro or (C ₁ -C ₄ ) -haloalkyl;
R ¹⁸ and R ²⁰ are the same or different and are OR ²⁴ , SR ²⁴ , NR ²⁴ R ²⁵ or a substituted or unsubstituted 3 to 7 membered heterocycle having at least one N atom and up to 3 hetero atoms, N To a radical selected from the group consisting of (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy and substituted or unsubstituted phenyl, connected via an atom to a carbonyl group of a compound of Formula II and Formula III Substituted or unsubstituted by;
R ²⁴ is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical;
R ²⁵ is hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₁ -C ₆ ) -alkoxy or substituted or unsubstituted phenyl;
R ²⁶ is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, (C _1- C ₆ ) -hydroxyalkyl, (C ₃ -C ₁₂ ) -cycloalkyl or tri- (C ₁ -C ₄ ) -alkyl-silyl;
R ²⁷ , R ²⁸ and R ²⁹ are the same or different and are hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₃ -C ₁₂ ) -cycloalkyl or substituted or substituted Unsubstituted phenyl;
R ²¹ is (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -haloalkenyl or (C ₃ -C ₇ ) -cycloalkyl;
R ²² and R ²³ are the same or different and are hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl, (C ₂ -C ₄ ) -alkynyl, (C ₁ -C ₄ ) -Haloalkyl, (C ₂ -C ₄ ) -haloalkenyl, (C ₁ -C ₄ ) -alkylcarbamoyl- (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenylcarba Moyl- (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₄ ) -alkyl, dioxoranyl- (C ₁ -C ₄ ) -alkyl, thiazolyl, furyl , Furylalkyl, thienyl, piperidyl or substituted or unsubstituted phenyl, or
R ²² and R ²³ together form a substituted or unsubstituted heterocyclic ring, preferably oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring);
b) at least one compound selected from the group consisting of:
1,8-naphthalinic anhydride,
Methyl diphenylmethoxy acetate,
Cyanomethoxyimino (phenyl) acetonitrile (thiomethynyl),
1,3-dioxoran-2-ylmethoxyimino (phenyl) acetonitrile (oxabetrinyl),
4'-chloro-2,2,2-trifluoroacetophenone O-1,3-dioxolan-2-ylmethyloxime (fluxopenim),
4,6-dichloro-2-phenylpyrimidine (fenchlorim),
Benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole),
2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),
N- (4-methylphenyl) -N '-(1-methyl-1-phenylethyl) urea (dimron),
1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea,
1- [4- (N-4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea,
1- [4- (N-naphthoylsulfamoyl) phenyl] -3,3-dimethylurea,
(2,4-dichlorophenoxy) acetic acid (2,4-D),
(4-chlorophenoxy) acetic acid,
(R, S) -2- (4-chloro-o-tolyloxy) propionic acid (mecoprop),
4- (2,4-dichlorophenoxy) butyric acid (2,4-DB),
(4-chloro-o-tolyloxy) acetic acid (MCPA),
4- (4-chloro-o-tolyloxy) butyric acid,
4- (4-chlorophenoxy) butyric acid,
3,6-dichloro-2-methoxybenzoic acid (dicamba),
1- (ethoxycarbonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor) and salts and esters thereof;
c) N-acylsulfonamides of formula V and salts thereof:
Formula V

[Wherein,
R ³⁰ is hydrogen, hydrocarbon radical, hydrocarbon-oxy radical, hydrocarbon-thio radical or heterocyclyl radical, and the last four radicals mentioned are each unsubstituted or halogen, cyano, nitro, amino, hydroxyl, carboxyl , Formyl, carboxamide, sulfonamide and at least one same or different radical selected from the group consisting of radicals of the general formula Z ^a -R ^a , wherein each hydrocarbon moiety preferably has from 1 to 20 carbon atoms The carbon-containing radical R ³⁰ including substituents preferably has 1 to 30 carbon atoms;
R ³¹ is hydrogen or (C ₁ -C ₄ ) -alkyl, or
R ³⁰ and R ³¹ together with the group of the formula -CO-N- are residues of 3 to 8 membered saturated or unsaturated rings;
R ³² is the same or different and is a halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, CONH ₂ , SO ₂ NH ₂ or a radical of the formula Z ^b -R ^b ;
R ³³ is hydrogen or (C ₁ -C ₄ ) -alkyl;
R ³⁴ is the same or different and is a halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH ₂ , SO ₂ NH ₂ or a radical of the formula Z ^c -R ^c ;
R ^a is a hydrocarbon radical or a heterocyclyl radical, wherein the two radicals mentioned last are each unsubstituted or halogen, cyano, nitro, amino, hydroxyl, mono- and di-[(C ₁ -C ₄ Substituted with one or more identical or different radicals selected from the group consisting of: -alkyl] amino), or an alkyl radical wherein a plurality, preferably two or three, non-adjacent CH ₂ groups are replaced with one oxygen atom in each case ego;
R ^b and R ^c are the same or different and represent a hydrocarbon radical or a heterocyclyl radical, wherein the two radicals mentioned last are each unsubstituted or halogen, cyano, nitro, amino, hydroxyl, phosphoryl, halo- (C ₁ -C ₄ ) -alkoxy, mono- and di-[(C ₁ -C ₄ ) -alkyl] amino are substituted with one or more identical or different radicals selected from the group), or a plurality, preferably Two or three non-adjacent CH ₂ groups are in each case an alkyl radical replaced by one oxygen atom;
Z ^a is a general formula O, S, CO, CS, CO-O, CO-S, 0-CO, S-CO, SO, SO ₂ , NR ^* , CO-NR ^* , NR ^* -CO, SO _2- Is a divalent group of NR ^* or NR ^* -SO ₂ , the bond given to the right of each divalent group is bonded to the radical R ^a , and the radicals R ^* in the last five radicals mentioned are each independently In H, (C ₁ -C ₄ ) -alkyl or halo- (C ₁ -C ₄ ) -alkyl;
Z ^b and Z ^c are each independently a direct bond or a general formula O, S, CO, CS, CO-O, CO-S, 0-CO, S-CO, SO, SO ₂ , NR ^* , SO _2- A _divalent group of NR ^* , NR ^* -SO ₂ , CO-NR ^* or NR ^* -CO, in the case of an asymmetric diatomic group, the atoms on the right side are linked to the radicals R ^b or R ^c and the last five The radicals R ^* in the radicals each independently in each occurrence are H, (C ₁ -C ₄ ) -alkyl or halo- (C ₁ -C ₄ ) -alkyl;
n is an integer from 0 to 4;
t is an integer from 0 to 5;
d) Acylsulfamoylbenzamides of formula VI:
Formula VI

[Wherein,
X ³ is CH or N;
R ³⁵ is a hydrogen, heterocyclyl or hydrocarbon radical, the last two mentioned radicals being halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH ₂ , SO ₂ NH ₂ and Z ^d -R ^d Unsubstituted or substituted with one or more identical or different radicals selected from the group consisting of;
R ³⁶ is hydrogen, hydroxyl, (C ₁ -C ₆ ) -alkyl, (C ₂ -C ₆ ) -alkenyl, (C ₂ -C ₆ ) -alkynyl, (C ₁ -C ₆ ) -alkoxy or (C ₂ -C ₆ ) -alkenyloxy, the last five radicals mentioned are halogen, hydroxyl, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy and (C _1- Unsubstituted or substituted with one or more identical or different radicals selected from the group consisting of C ₄ ) -alkylthio; or
R ³⁵ and R ³⁶ are 3- to 8-membered saturated or unsaturated rings together with the nitrogen atom to which they are attached;
R ³⁷ is the same or different and is halogen, cyano, nitro, amino, hydroxyl, carboxyl, CH0, C0NH ₂ , SO ₂ NH ₂ or Z ^e -R ^e ;
R ³⁸ is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₂ -C ₄ ) -alkenyl or (C ₂ -C ₄ ) -alkynyl;
R ³⁹ is the same or different and is halogen, cyano, nitro, amino, hydroxyl, carboxyl, phosphoryl, CHO, CONH ₂ , SO ₂ NH ₂ or Z ^f -R ^f ;
R ^d is a (C ₂ -C ₂₀ ) -alkyl radical wherein the carbon chain is interrupted once or more than once by an oxygen atom, or is a heterocyclyl or hydrocarbon radical, and the last two radicals mentioned are halogen, cyano, nitro, amino, hydroxyl, mono- and di _{- [(C 1 -C 4)} - alkyl] in the same or more than one selected from the group is optionally substituted with different radicals consisting of amino;
R ^e and R ^f are the same or different and the carbon chain is a (C ₂ -C ₂₀ ) -alkyl radical interrupted once or more than once by an oxygen atom, or is a heterocyclyl or hydrocarbon radical, the last mentioned 2 Radicals in the group consisting of halogen, cyano, nitro, amino, hydroxyl, phosphoryl, (C ₁ -C ₄ ) -haloalkoxy, mono- and di-[(C ₁ -C ₄ ) -alkyl] amino Unsubstituted or substituted with one or more identical or different radicals selected;
Z ^d is a divalent unit selected from the group consisting of O, S, CO, CS, C (O) O, C (O) S, SO, SO ₂ , NR ^* , C (O) NR ^*, and SO ₂ NR ^* ego;
Z ^e and Z ^f are the same or different and are direct bonds or are O, S, CO, CS, C (O) O, C (O) S, SO, SO ₂ , NR ^* , SO ₂ NR ^* and C ( O) a unit selected from the group consisting of NR ^* is a unit;
R ^* is hydrogen, (C ₁ -C ₄ ) -alkyl or (C ₁ -C ₄ ) -haloalkyl;
s is an integer from 0 to 4;
o is an integer of 0 to 5 when X is CH, and an integer of 0 to 4 when X is N; And
e) a compound of formula (VII) comprising stereoisomers and agriculturally common salts:
Formula VII

[Wherein the symbols and indices have the following meanings:
R ⁴⁰ is hydrogen, (C ₁ -C ₄₎ - alkyl, (C ₁ -C ₄₎ - alkyl, or -X ⁴ (C ₁ -C ₄₎ - a (C ₁ -C ₄ alkyl substituted with halo -X ⁴ ) -Alkyl, (C ₁ -C ₄ ) -haloalkyl, NO ₂ , CN, —COO-R ⁴³ , NR ₂ ⁴⁴ , SO ₂ NR ₂ ⁴⁵ or CONR ₂ ⁴⁶ ;
R ⁴¹ is hydrogen, halogen, (C ₁ -C ₄ ) -alkyl, CF ₃ , (C ₁ -C ₄ ) -alkoxy or (C ₁ -C ₄ ) -haloalkoxy;
R ⁴² is hydrogen, halogen or (C ₁ -C ₄ ) -alkyl;
Q ¹ , Q ² , E and G are the same or different and are O, S, CR ₂ ⁴⁷ , CO, NR ⁴⁸ or a group of formula VIII:
Formula VIII

Provided that at least one Q ¹ , Q ² , E and G group is a carbonyl group, exactly one of these groups is a radical of formula (VIII) below and the group of formula (VIII) is adjacent to a carbonyl group,
β) two adjacent Q ¹ , Q ² , E and G groups cannot be oxygen at the same time;
R ^g is the same or different and is hydrogen or (C ₁ -C ₈ ) -alkyl, or two radicals R ^g together are (C ₂ -C ₆ ) -alkylene;
A is Y ³ -R ^h or NR ₂ ⁴⁹ ;
X ⁴ is 0 or S (O) _x ;
Y ³ is O or S;
R ^h is hydrogen, (C ₁ -C ₈ ) -alkyl, (C ₁ -C ₈ ) -haloalkyl, (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₈ ) -alkyl, (C _3- C ₆ ) -alkenyloxy- (C ₁ -C ₈ ) -alkyl, phenyl- (C ₁ -C ₈ ) -alkyl, wherein the phenyl ring is halogen, (C ₁ -C ₄ ) -alkyl, CF ₃ , Methoxy or methyl-S (O) _x substituted or unsubstituted), (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 or a tetrahydro-furyl;
R ⁴³ is hydrogen or (C ₁ -C ₄ ) -alkyl;
R ⁴⁴ is the same or different and is hydrogen, (C ₁ -C ₄ ) -alkyl or (C ₁ -C ₄ ) -alkylcarbonyl, or two radicals R ⁴⁴ together are (C ₄ -C ₅ ) -alkylene ego;
R ⁴⁵ and R ⁴⁶ are each independently the same or different at each occurrence and are hydrogen or (C ₁ -C ₄ ) -alkyl, or two radicals R ⁴⁵ and / or R ⁴⁶ together are (C ₄ -C ₅ ) -Alkylene, wherein one CH ₂ group can be replaced by O or S or one or two CH ₂ groups by NR ⁱ , wherein R ⁱ is hydrogen or (C ₁ -C ₈ ) -alkyl Can be;
R ⁴⁷ is the same or different and is hydrogen or (C ₁ -C ₈ ) -alkyl, or two radicals R ⁴⁷ together are (C ₂ -C ₆ ) -alkylene;
R ⁴⁸ is hydrogen, (C ₁ -C ₈ ) -alkyl, substituted or unsubstituted phenyl, or unsubstituted or substituted benzyl on the phenyl ring;
R ⁴⁹ is the same or different and is hydrogen, (C ₁ -C ₈ ) -alkyl, phenyl, phenyl- (C ₁ -C ₈ ) -alkyl, wherein the phenyl ring is F, Cl, Br, NO ₂ , CN, OCH ₃ , (C ₁ -C ₄ ) -alkyl or CH ₃ SO _2- ), (C ₁ -C ₄ ) -alkoxy- (C ₁ -C ₈ ) -alkyl, (C ₃ -C ₆ ) -Alkenyl, (C ₃ -C ₆ ) -alkynyl or (C ₃ -C ₆ ) -cycloalkyl, or two radicals R ⁴⁹ together are (C ₄ -C ₅ ) -alkylene, wherein one The CH ₂ group of may be replaced with O or S or one or two CH ₂ groups may be replaced with NR ^K , wherein R ^K is hydrogen or (C ₁ -C ₄ ) -alkyl;
m "is 0 or 1;
x is 0, 1 or 2].
[2" claim-type="Currently amended] The method of claim 1,
A herbicidally active composition in which the compound of formula (I) is a radical selected from the group consisting of the following formulas (V1 to V4):
Formula V1

Formula V2

Formula V3

Formula V4

Wherein the symbols and exponents have the following meanings:
R is hydrogen or (C ₁ -C ₄ ) -alkoxycarbonyl;
R ¹ is (C ₃ -C ₇ ) -cycloalkyl or (C ₁ -C ₄ ) -alkyl- (C ₃ -C ₇ ) -cycloalkyl;
R ² is hydrogen;
R ³ is hydrogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkyl-substituted arylsulfonyl, (C ₁ -C ₄ ) -alkyl-arylcarbonylmethyl or benzyl;
R ⁴ is (C ₁ -C ₄ ) -alkyl;
R ⁵ is (C ₁ -C ₄ ) -alkyl or (C ₁ -C ₄ ) -alkoxy, or two radicals R ⁵ are C ₂ -alkenyl;
R ⁶ is hydroxyl, (C ₁ -C ₄ ) -alkoxy or phenylthio;
R ⁷ is (C ₃ -C ₇ ) -cycloalkyl;
R ⁸ is cyano;
I is an integer from 0 to 3, and when I is 2 or more, the radicals R ⁵ may be the same or different from each other,
R ⁹ is the same or different and is (C ₁ -C ₄ ) -alkyl, halogen, nitro, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -haloalkoxy, (C ₁ -C ₄ ) -Alkylsulfonyl, (C ₁ -C ₄ ) -alkylsulfonyloxy, (C ₁ -C ₄ ) -alkylsulfonylamino or (C ₁ -C ₄ ) -alkoxycarbonyl;
q is 0, 1, 2 or 3.
[3" claim-type="Currently amended] The method according to claim 1 or 2,
Herbicidal active compositions comprising an emollient of Formula (II) and / or (III), wherein the symbols and indices have the following meanings:
R ¹⁸ and R ²⁰ are OR ²⁴ ;
R ²⁴ is hydrogen, (C ₁ -C ₁₈ ) -alkyl, (C ₃ -C ₁₂ ) -cycloalkyl, (C ₂ -C ₈ ) -alkenyl or (C ₂ -C ₁₈ ) -alkynyl The carbon-containing group may be substituted by one or more radicals R ⁵⁰ ;
R ⁵⁰ is the same or different and is halogen, hydroxyl, (C ₁ -C ₈ ) -alkoxy, (C ₁ -C ₈ ) -alkylthio, (C ₂ -C ₈ ) -alkenylthio, (C _2- C ₈₎ - alkynyl, thio, (C ₂ -C ₈₎ - alkenyloxy, (C ₂ -C ₈₎ - alkynyloxy, (C ₃ -C ₇₎ - cycloalkyl, (C ₃ -C ₇₎ -Cycloalkoxy, cyano, mono- and di-((C ₁ -C ₄ ) -alkyl) amino, carboxyl, (C ₁ -C ₈ ) -alkoxycarbonyl, (C ₂ -C ₈ ) -alkenyloxy Carbonyl, (C ₁ -C ₈ ) -alkylthiocarbonyl, (C ₂ -C ₈ ) -alkynyloxycarbonyl, (C ₁ -C ₈ ) -alkylcarbonyl, (C ₂ -C ₈ )- Alkenylcarbonyl, (C ₂ -C ₈ ) -alkynylcarbonyl, 1- (hydroxyimino)-(C ₁ -C ₆ ) -alkyl, 1-[(C ₁ -C ₄ ) -alkylimino ]-(C ₁ -C ₄ ) -alkyl, 1-[(C ₁ -C ₄ ) -alkoxyimino]-(C ₁ -C ₆ ) -alkyl, (C ₁ -C ₈ ) -alkylcarbonylamino, (C ₂ -C ₈ ) -alkenylcarbonylamino, (C ₂ -C ₈ ) -alkynylcarbonylamino, aminocarbonyl, (C ₁ -C ₈ ) -alkylaminocarbonyl, di- (C ₁ -C ₆₎ - alkylamino-carbonyl, (C ₂ -C ₆₎ - alkenyl Aminocarbonyl, (C ₂ -C ₆₎ - alkynyl, aminocarbonyl, (C ₁ -C ₈₎ - alkoxy-carbonyl-amino, (C ₁ -C ₈₎ - alkylamino-carbonyl-amino, unsubstituted or substituted by R ⁵¹ a (C ₁ -C ₆₎ substituted-alkyl-carbonyl-oxy, (C ₂ -C ₆₎ - alkenyl-carbonyl-oxy, (C ₂ -C ₆₎ - alkynyl-carbonyl-oxy, (C ₁ -C ₈ ) -Alkylsulfonyl, phenyl, phenyl- (C ₁ -C ₆ ) -alkoxy, phenyl- (C ₁ -C ₆ ) -alkoxycarbonyl, phenoxy, phenoxy- (C ₁ -C ₆ ) -alkoxy, Phenoxy- (C ₁ -C ₆ ) -alkoxycarbonyl, phenylcarbonyloxy, phenylcarbonylamino or phenyl- (C ₁ -C ₆ ) -alkylcarbonylamino, and the last nine radicals mentioned are phenyl Unsubstituted or substituted on the ring R ⁵² , SiR ' ₃ , OSiR' ₃ , R ' ₃ Si- (C ₁ -C ₈ ) -alkoxy, CO-O-NR' ₂ , ON = CR ' ₂ , N = CR ' ₂ , 0NR' ₂ , NR ' ₂ , CH (OR') ₂ , O (CH ₂ ) _w -CH (OR ') ₂ , CR'"(OR') ₂ , O (CH ₂ ) _w CR'" (oR ") ₂ or R" O-CHR '"CHCOR" - (C 1 -C 6) - mono- or multi-substituted by alkoxy;
R ⁵¹ is the same or different and is halogen, nitro, (C ₁ -C ₄ ) -alkoxy, or phenyl unsubstituted or substituted with one or more radicals R ⁵² ;
R ⁵² is the same or different and is halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -halo Alkoxy or nitro;
R 'is the same or different and is hydrogen, (C ₁ -C ₄ ) -alkyl or phenyl unsubstituted or substituted with one or more radicals R ⁵² , or two radicals R ′ together are (C ₂ -C ₆ )- To form an alkanediyl chain;
R ″ is the same or different and is (C ₁ -C ₄ ) -alkyl, or two radicals R ″ together form a (C ₂ -C ₆ ) -alkanediyl chain;
R ′ ″ is hydrogen or (C ₁ -C ₄ ) -alkyl;
w is 0, 1, 2, 3, 4, 5 or 6.
[4" claim-type="Currently amended] The method according to claim 1 or 2,
R ³⁰ is hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₃ -C ₆ ) -cycloalkyl, furanyl or thienyl, wherein the four radicals mentioned last are each unsubstituted or halogen, (C Substituted with one or more substituents selected from the group consisting of _1- C ₄ ) -alkoxy, halo- (C ₁ -C ₆ ) -alkoxy and (C ₁ -C ₄ ) -alkylthio, and in the case of a cyclic radical, Substituted with C ₁ -C ₄ ) -alkyl or (C ₁ -C ₄ ) -haloalkyl;
R ³¹ is hydrogen;
R ³² is halogen, halo- (C ₁ -C ₄ ) -alkyl, halo- (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy, ( C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkoxycarbonyl or (C ₁ -C ₄ ) -alkylcarbonyl, preferably (C ₁ like halogen, trifluoromethyl -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -alkoxy, halo- (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkoxycarbonyl or (C ₁ -C ₄ )- Alkylsulfonyl;
R ³³ is hydrogen;
R ³⁴ is halogen, (C ₁ -C ₄ ) -alkyl, halo- (C ₁ -C ₄ ) -alkyl, halo- (C ₁ -C ₄ ) -alkoxy, (C ₃ -C ₆ ) -cycloalkyl, Phenyl, (C ₁ -C ₄ ) -alkoxy, cyano, (C ₁ -C ₄ ) -alkylthio, (C ₁ -C ₄ ) -alkylsulfinyl, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄₎ - alkoxycarbonyl or (C ₁ -C ₄₎ - alkyl-carbonyl, preferably halogen, (C ₁ -C ₄₎ - alkyl, such as methyl, trifluoromethyl (C ₁ - C ₄ ) -haloalkyl, halo- (C ₁ -C ₄ ) -alkoxy, (C ₁ -C ₄ ) -alkoxy or (C ₁ -C ₄ ) -alkylthio;
n is 0, 1 or 2;
A herbicidally active composition comprising an emollient of formula V or a salt thereof, wherein t is 1 or 2.
[5" claim-type="Currently amended] The method according to claim 1 or 2,
X ³ is CH;
R ³⁵ is hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₃ -C ₆ ) -cycloalkyl, (C ₂ -C ₆ ) -alkenyl, (C ₅ -C ₆ ) -cycloalkenyl, phenyl Or 3-6 membered heterocyclyl having up to 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, the last six radicals mentioned being halogen, (C ₁ -C ₆ ) -alkoxy, (C ₁ -C ₆ ) -haloalkoxy, (C ₁ -C ₂ ) -alkylsulfinyl, (C ₁ -C ₂ ) -alkylsulfonyl, (C ₃ -C ₆ ) -cycloalkyl, (C _1- C ₄₎ - alkoxycarbonyl, (C ₁ -C ₄₎ - alkyl-carbonyl and is not substituted or substituted from the group consisting of phenyl by identical or different substituents selected one or more, in the case of cyclic radicals, also (C ₁ - Unsubstituted or substituted with C ₄ ) -alkyl or (C ₁ -C ₄ ) -haloalkyl;
R ³⁶ is hydrogen, (C ₁ -C ₆ ) -alkyl, (C ₂ -C ₆ ) -alkenyl or (C ₂ -C ₆ ) -alkynyl, and the last three radicals mentioned are halogen, hydroxyl Unsubstituted or substituted with one or more identical or different substituents selected from the group consisting of (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -alkoxy and (C ₁ -C ₄ ) -alkylthio;
R ³⁷ is the same or different and is halogen, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -haloalkoxy, nitro, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -Alkoxy, (C ₁ -C ₄ ) -alkylsulfonyl, (C ₁ -C ₄ ) -alkoxycarbonyl or (C ₁ -C ₄ ) -alkylcarbonyl;
R ³⁸ is hydrogen;
R ³⁹ is the same or different and is halogen, nitro, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ ) -haloalkyl, (C ₁ -C ₄ ) -haloalkoxy, (C ₃ -C ₆ ) -Cycloalkyl, phenyl, (C ₁ -C ₄ ) -alkoxy, cyano, (C ₁ -C ₄ ) -alkylthio, (C ₁ -C ₄ ) -alkylsulfinyl, (C ₁ -C ₄ ) -Alkylsulfonyl, (C ₁ -C ₄ ) -alkoxycarbonyl or (C ₁ -C ₄ ) -alkylcarbonyl;
s is 0, 1 or 2;
An herbicidally active composition comprising an emollient of formula VI wherein o is 1 or 2.
[6" claim-type="Currently amended] The method according to any one of claims 1 to 5,
A herbicidal active composition having a weight ratio of herbicide to emollient 1: 100 to 100: 1.
[7" claim-type="Currently amended] The method according to any one of claims 1 to 6,
A herbicidally active composition also comprising additional herbicides.
[8" claim-type="Currently amended] The method of claim 7, wherein
A herbicidally active composition wherein the additional herbicide is sulfonylurea.
[9" claim-type="Currently amended] A herbicidally active amount of the herbicidal active composition as claimed in any one of claims 1 to 8, which is harmful to crops of useful plants, including application to plants, crop plants, seeds of plants or areas in which plants grow. How to control plants.
[10" claim-type="Currently amended] The method of claim 9,
How plants belong to the group consisting of corn, wheat, rye, barley, oats, rice, sugar cane, cotton and soybeans.
[11" claim-type="Currently amended] The method according to claim 9 or 10,
The plant is a genetically modified plant.
[12" claim-type="Currently amended] Use of the herbicidal active composition as claimed in any one of claims 1 to 8 for controlling harmful plants in crops of useful plants.

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引用文献:

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公开号 | 申请日 | 公开日 | 申请人 | 专利标题

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法律状态:
1998-11-21|Priority to DE19853827A

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1998-11-21|Priority to DE19853827.8

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1999-11-05|Application filed by 바이세르트, 리펠, 아벤티스 크롭사이언스 게엠베하

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2001-08-22|Publication of KR20010080501A

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2004-07-28|First worldwide family litigation filed

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2007-02-05|Application granted

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2007-02-05|Publication of KR100678802B1

优先权:

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申请号 | 申请日 | 专利标题

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DE19853827A|DE19853827A1|1998-11-21|1998-11-21|Selective herbicidal composition for use in e.g. cereals, cotton or soya, comprises p-hydroxyphenyl pyruvate dioxygenase inhibiting benzoyl compound herbicide and safener, e.g. fenclorim or dicamba|

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DE19853827.8|1998-11-21|