JPH08208412A - Herbicide based on aryl uracil for being used in cultivationof rice plant - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new herbicide composition exhibiting especially excellent selective herbicidal action in rice culture by combining an aryluracil or an arylthiouracil with a specific herbicide for rice culture. SOLUTION: This herbicide composition is produced by combining (A) an aryluracil or arylthiouracil of the formula I or their isomers of the formula II [Q<1> and Q<2> are each O or S; R<1> is H or a halogen; R<2> is a halogen or cyano; R<3> is A<1> -A<2> -A<3> (A<1> is single bond, O, S, etc.; A<2> is single bond, O, S, etc.; A<3> is H, amino, cyano, etc.; R<4> and R<5> are each H, a halogen or an alkyl; R<6> is H, OH, amino, an alkyl, etc.] with (B) a herbicidal active compound selected from herbicides for rice culture such as (a) a compound of the formula III (R<7> and R<8> are each H, an alkyl, an alkenyl, etc.) and (b) cyclosulfamuron, AKD-741, amiprophos(-methyl), etc. The weight ratio of the compound of the formula I or II to the compound of (a) and/or (b) is preferably 1:(0.001-1,000), especially 1:(0.01-100).

Description

Detailed Description of the Invention

[0001]

The invention relates on the one hand to the known aryluracils (or arylthiouracils or compounds which are aryluracils or isomers of these with arylthiouracils) and on the other hand to the other substance groups known It relates to a combination of synergistically active compounds which are new herbicides which consist of herbicides and which can be used with particular high excellence in selective weed control in rice cultivation.

[0002]

BACKGROUND OF THE INVENTION As a broadly active herbicide, aryluracil (or aryl-thio-uracil) has been described in many patent applications (WO 91/00278, US Pat. Nos. 4,979,982, 5). , 169,430, European Patent Application Publication Nos. 408,382 and 563,3.
84, US Pat. Nos. 5,084,084, 5,12
7,935, 5,154,755, German Patents 4,327,743, 4,343,451, 4,414,326). However, the known aryl uracil [or aryl (thio)
Uracil] has a number of defects in its action, especially against monocot weeds.

[0003]

Surprisingly, the combination of known weed active compounds, for example from the group of substances carbamoyltetrazolinone and / or active compounds from the group of compounds heretofore known as herbicides for application in rice. Upon application, the known herbicidally active compounds from a large group of aryluracils (or compounds which are arylthiouracils or aryluracils or isomers with arylthiouracils) show a marked synergistic effect on the action against weeds, and It has been found that it can be used particularly advantageously as a broadly active combination preparation for the selective weeding of both monocotyledonous and dicotyledonous weeds before and after germination of rice cultivation.

The present invention includes (1) the general formula (I)

[0005]

[Chemical 4]

An aryluracil or aryl-thiouracil of the general formula (Ia)

[0007]

Embedded image

In each of the formulas (I) and (Ia), Q ¹ represents oxygen or sulfur, Q ² represents oxygen or sulfur, R ¹ represents hydrogen or halogen, R ²
Represents halogen or cyano, and R ³ represents a group —A ¹ —A ²
Represents -A ³ , wherein A ¹ is a single bond, oxygen, sulfur, -S
_{O -, - SO 2 -,} - CO- or a group -N-A ⁴ - represents, here? A ⁴ represents hydrogen, hydroxyl, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl, or (A ¹ Each represents an optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkynediyl, cycloalkanediyl, cycloalkenediyl or arenediyl, A ² is a single bond, oxygen, sulfur, -SO-, -SO. _2- ,
Represents CO or a group -N-A ^4, wherein in A ⁴ is hydrogen, alkyl, aryl, alkylcarbonyl, or represents alkylsulfonyl or arylsulfonyl, or (A ²⁾ are each optionally optionally substituted alkanediyl , Alkenediyl, azaalkenediyl, alkynediyl, cycloalkanediyl, cycloalkenediyl or alendyl and A ³ is hydrogen, hydroxyl, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulfo. , Chlorosulfonyl, halogen or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl, Alkoxy (thio) phosphoryl,
Alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino, alkynyloxycarbonyl, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl. , Cycloalkylalkoxycarbonyl, aryl, aryloxy, arylalkyl, arylalkoxy, aryloxycarbonyl, arylalkoxycarbonyl, heterocycle, heterocyclic alkyl,
Represents heterocyclic alkoxy or heterocyclic alkoxycarbonyl, R ⁴ represents hydrogen, halogen or optionally substituted alkyl, R ⁵ represents hydrogen, halogen or optionally substituted alkyl, and R ⁶ represents hydrogen, hydroxyl, amino or alkyl, alkoxy, alkenyl or alkynyl, each of which may be optionally substituted (“active compound of group 1”), and (2) the following active compound (a) and One or more herbicidally active compounds from a second group of herbicides (“group 2 active compounds”), including / or (b) type: (a) general formula (II)

[0009]

[Chemical 6]

In the formula, R ⁷ and R ⁸ are the same or different and independently of each other are each hydrogen or optionally optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, Represents a group from the group consisting of aryl and arylalkyl, and R ⁹ is each optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, aryl, arylalkyl, heterocycle and heterocycle. A carbamoyltetrazolinone representing a group from the group consisting of cyclic alkyl, (b) a rice herbicide from the following list ("common name" or "code number"): cyclosulfamurone, AKD-741, Amiprophos (-methyl), Anilophos, Benfrusate , Bensulfuron (-methyl), bensulide, bentazone, bentiocarb (thiobencarb), benzophenap, bifenox, bromobutide, butachlor, butamifos, butenachlor, cafenstrol, chlormethoxynil, chlornitrophen, symmethyline, CL-303569, C
L-303578, Cinosulfuron, Kromeprop,
2,4-D, cyhalofop-butyl, dimepiperate, dimetamethrin, dithiopyr, azimsulfuron,
Jimron (Daimron), Esplocarb, GS-32
911, HOE-404, HOE-30374, HOK
-7501, etobenzanide, imazosulfuron, cumyluron, KIH-911 (KUH-911), KIH9
20 (KUH920), triazophenamide, KPP
-314, MCPA, MCPB, mefenacet, molinate, NC-310, NC-311, nabroanilide, nitrophen, tenylchlor, oxadiazone, piperophos, pretylachlor, promethrin, propanil, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxifene, pyributicarb, quinclorac, It is characterized by a combination of active compounds of an effective content of cimetrin, trifluralin, X-52, generally 0.001 to 100 per 1 part by weight of active compound of group 1.
It relates to a synergistic herbicidal composition in which 0 parts by weight of the active compound of group 2 are distributed in each case.

Of particular interest are (1) Q ¹ represents oxygen or sulfur, Q ² represents oxygen or sulfur, R ¹ represents hydrogen, fluorine, chlorine or bromine, and R ² represents fluorine or chlorine. , Bromine, iodine or cyano, R ³ represents a group —A ¹ —A ² —A ³ , where A ¹ is a single bond, oxygen, sulfur, —SO—, —SO ₂ —, —
CO- or a group -N-A ⁴ - represents, here A ⁴ is hydrogen, hydroxyl, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - alkoxy, phenyl, C ₁ -C ₄ - alkylsulfonyl or phenyl C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl, C ₂ -C ₆ -azaalkene, each of which represents sulfonyl or (A ¹ ) is optionally substituted with fluorine, chlorine or bromine. diyl, C ₂ ~C ₆ - alkynediyl, C ₃ ~C ₆ - cycloalkanediyl, C ₃ -C ₆
Represents cycloalkenediyl or phenylene, A
² is a single bond, oxygen, _{sulfur, -SO -, - SO 2 -} , - CO
- or a group -N-A ⁴ - represents, here A ⁴ is hydrogen, hydroxyl, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - alkoxy, phenyl, C ₁ -C ₄ - alkylsulfonyl or phenylsulfonyl Or (A ² ) is C ₁ optionally substituted with fluorine, chlorine or bromine, respectively.
-C ₆ - alkanediyl, C ₂ -C ₆ - alkanediyl,
C ₂ -C ₆ - aza alkenediyl, C ₂ -C ₆ - alkynediyl, C ₃ -C ₆ - cycloalkyl alkanediyl, C ₃ -C ₆ - represents a cycloalkene diyl or phenylene, A ³ is hydrogen, hydroxyl, amino , Cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen; each having 1 to 6 carbon atoms in the alkyl group, and each optionally halogen or C ₁ -C ₄ -alkoxy. An alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl which may be substituted with a carbon atom 2 in the alkenyl, alkylidene or alkynyl group, respectively.
Alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyloxy, alkynyloxy, alkynylamino or alkynyloxycarbonyl, each having 6 and optionally substituted with halogen; each in a cycloalkyl group. Having 1 to 4 carbon atoms and optionally ₁ to ₄ carbon atoms in the alkyl group, and optionally halogen, cyano, carboxyl, C ₁ -C ₄ -alkyl and / or C
₁ -C ₄ - alkoxy - cycloalkyl which may be substituted with carbonyl, cycloalkyloxy, cycloalkylalkyl, cycloalkyl alkoxycarbonyl, cycloalkylidene amino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl; or each optionally a nitro, Cyano, carboxyl, halogen, C _{1 to} C ₄
- alkyl, C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ -
Alkyloxy, C ₁ -C ₄ -halogenoalkyloxy and / or phenyl optionally substituted with C ₁ -C ₄ -alkoxy-carbonyl, phenyloxy, phenyl-
C ₁ -C ₄ - alkyl, phenyl -C ₁ -C ₄ - alkoxy, phenyloxy carbonyl or phenyl -C ₁
˜C ₄ -Alkoxycarbonyl, pyrrolyl (pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl (optionally fully or partially hydrogenated in each case), Pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C
₁ -C ₄ - alkyl, furyl -C ₁ -C ₄ - alkyl, thienyl -C ₁ -C ₄ - alkyl, oxazolyl -C ₁ -C ₄ -
Alkyl, isoxazolyl -C ₁ -C ₄ - alkyl, thiazolyl -C ₁ -C ₄ - alkyl, pyridinyl -C ₁ -C ₄ -
Represents alkyl, pyrimidinyl-C ₁ -C ₄ -alkyl, pyrazolylmethoxy, furylmethoxy, perhydropyranylmethoxy or pyridylmethoxy, R ⁴ is hydrogen,
Represents fluorine, chlorine, bromine or an alkyl having 1 to 4 carbon atoms which may be optionally substituted with fluorine and / or chlorine, wherein R ⁵ is hydrogen, fluorine, chlorine, bromine or optionally fluorine and / or chlorine is alkyl having 1-4 carbon atoms which may have, and R ⁶ has a hydrogen, hydroxyl, up to four amino or each carbon atoms, and each optionally fluorine, optionally substituted with chlorine or cyano A compound of formula (I) or (Ia) above, which represents alkyl, alkoxy, alkenyl or alkynyl, and (2) a herbicide containing any of the following types of active compounds (a) and / or (b): 1-3 one active compound from the second group: (a) R ⁷ and R ⁸ are identical or different and hydrogen in each case independently of one another; each coal It has up to 6 atoms, and each optionally halogen, cyano or C ₁ -C ₄
-Alkyl, alkenyl or alkynyl optionally substituted with alkoxy; each having from 3 to 8 carbon atoms in the cycloalkyl moiety and optionally 5 carbon atoms in the cycloalkenyl moiety.
Or 6 and optionally 1 to 4 carbon atoms in the alkyl part and each optionally halogen, cyano, carboxyl, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy-
Cycloalkyl, cycloalkenyl or cycloalkylalkyl optionally substituted with carbonyl; or each optionally halogen, cyano, nitro, carboxyl, C
₁ -C ₄ - alkyl, C _{1 ~C 4} - halogenoalkyl, C ₁
Represents phenyl, naphthyl, phenyl-C ₁ -C ₄ -alkyl or naphthyl-C ₁ -C ₄ -alkyl optionally substituted with ˜C ₄ -alkoxy or C ₁ -C ₄ -halogenoalkoxy, and R ⁹ Each have up to 6 carbon atoms and each is optionally halogen, cyano or C ₁ -C ₄
-Alkyl, alkenyl or alkynyl optionally substituted with alkoxy; each having from 3 to 8 carbon atoms in the cycloalkyl moiety and optionally 5 carbon atoms in the cycloalkenyl moiety.
Or 6 and optionally 1 to 4 carbon atoms in the alkyl part and each optionally halogen, cyano, carboxyl, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy-
Cycloalkyl, cycloalkenyl or cycloalkylalkyl optionally substituted with carbonyl; each optionally halogen, cyano, nitro, carboxyl, C ₁ -C ₄
- alkyl, C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ -
Phenyl, naphthyl, phenyl-C ₁ optionally substituted with alkoxy or C ₁ -C ₄ -halogenoalkoxy
-C ₄ - alkyl or naphthyl -C ₁ -C ₄ - alkyl; or each optionally halogen, cyano, nitro, carboxyl, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - Alkoxy or heterocycle optionally substituted with C ₁ -C ₄ -halogenoalkoxy or heterocyclic represents C ₁ -C ₄ -alkyl, wherein the heterocycle is in each case (in combination with alkyl) furyl. , Tetrahydrofuryl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,
A carbamoyltetrazolinone of the above formula (II) representing oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidyl and triazinyl, (b) a rice herbicide from the following list ("common name" or "code number"): cyclosulfam Ron, AKD-741, Amiprophos (-methyl), Anilophos, Benfurasate, Bensulfuron (-methyl), Bencelide, Bentazone,
Benchiocalb (thiobencarb), benzophenap, bifenox, bromobutide, butachlor, butamifos, butenachlor, cafenstrol, chlormethoxynil, chlornitrophen, symmethyline, C
L-303569, CL-303578, Cinosulfuron, clomeprop, 2,4-D, cyhalofop-butyl, dimepiperate, dimetamethrin, dithiopyr,
Azimsulfuron, Zimron (Daimron), Esplocarb, GS-32911, HOE-404, HOE-
30374, HOK-7501, etobenzanide, imazosulfuron, cumyluron, KIH-911 (KUH-
911), KIH920 (KUH920), triazophenamide, KPP-314, MCPA, MCPB, mefenacet, molinate, NC-310, NC-31.
1, nabroanilide, nitrophen, tenylchlor, oxadiazone, piperofos, pretilachlor, promethrin, propanil, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxifene, pyributicarb, quinclorac, cimetrin, trifluralin and X-5.
A herbicidal composition according to the invention in which in each case there is generally distributed 0.01 to 100 parts by weight of the active compound of group 2 relative to 1 part by weight of active compound of group 1. is there.

Of very particular interest are: (1) Q ¹ represents oxygen or sulfur, Q ² represents oxygen or sulfur, R ¹ represents hydrogen, fluorine, chlorine or bromine, R ² is fluorine, Represents chlorine, bromine, iodine or cyano, R ³ represents a group —A ¹ -A ² —A ³ , wherein A ¹ represents a single bond, oxygen, sulfur, —SO—, —SO ₂ —, —
CO- or a group -N-A ⁴ - represents, here A ⁴ is hydrogen, hydroxyl, methyl, ethyl, n- or i-
Propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl, or (A ¹ ) is methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1, 1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethane-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2- Diyl, propyne-1,2-diyl or propyne-1,3-
Represents diyl, A ² is a single bond, oxygen, sulfur, —SO
_{-, - SO 2 -, -} CO- or a group -N-A ⁴ - represents, here A ⁴ is hydrogen, hydroxyl, methyl, ethyl, n- or i- propyl, methoxy, ethoxy,
n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl, or (A ² ) is methylene, ethane-1,1-diyl, ethane-1,2-diyl , Propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethane-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne -1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl, A ³ is hydrogen,
Hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulfo, fluorine, chlorine, bromine; methyl, ethyl, n- or i-propyl, n-, each optionally substituted with fluorine, chlorine, methoxy or ethoxy. i-, s- or t-butyl, n-, i
-, S- or t-pentyl, methoxy, ethoxy,
n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio , N- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-
Propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl,
Dipropoxyphosphoryl or diisopropoxyphosphoryl; propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycarbonyl, butenyloxy, each optionally substituted with fluorine or chlorine. Carbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl; each optionally fluorine, chlorine, cyano, carboxyl, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxy. Cyclopropyl optionally substituted with carbonyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, Clobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylideneamino, cyclohexylideneamino, cyclopentyloxy Carbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl;
Or each optionally nitro, cyano, carboxyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n
-Or i-propyl, difluoromethoxy, trifluoromethoxy, phenyl optionally substituted with methoxycarbonyl and / or ethoxycarbonyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, (each Optionally fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, Furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolmethyl,
Represents thiazolemethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy, R ⁴ represents hydrogen, fluorine, chlorine or each optionally methyl and ethyl optionally substituted with fluorine and / or chlorine, and R ⁵ represents Hydrogen, fluorine,
Represents chlorine or methyl or ethyl, each optionally substituted with fluorine and / or chlorine, and R ⁶
Is hydrogen, hydroxyl, amino or fluorine at any time,
Methyl, ethyl, n- or i-propyl, methoxy, ethoxy, optionally substituted with chlorine or cyano,
a compound of formula (I) or (Ia) above, representing n- or i-propoxy, propenyl or propynyl, and (2) a herbicide containing a type of active compound (a) and / or (b) below: One or two active compounds from the second group: (a) R ⁷ and R ⁸ are the same or different and independently of one another are each hydrogen; each optionally fluorine, chlorine, bromine, cyano, methoxy or ethoxy. Optionally substituted with methyl, ethyl, n- or i-propyl, n-, i
-, S- or t-butyl, propenyl, butenyl,
Pentenyl, propynyl, butynyl or pentynyl;
Fluorine, chlorine, bromine, cyano, carboxyl,
Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexyl optionally substituted with methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl. Methyl; or each optionally with fluorine, chlorine, bromine, cyano, nitro, carboxyl, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy. phenyl optionally substituted, represents benzyl or phenylethyl, each optionally fluorine R ^9, chlorine, bromine, cyano, good eye be substituted by methoxy or ethoxy Le, ethyl, n- or i-
Propyl, n-, i-, s- or t-butyl, n
-, I-, s- or t-pentyl, propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl; each optionally fluorine, chlorine, bromine, cyano, carboxyl, methyl, ethyl, n- or i-propyl,
Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted with methoxycarbonyl or ethoxycarbonyl; each optionally fluorine, chlorine, bromine, cyano , Nitro, carboxyl, methyl, ethyl, n- or t-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloroethyl, dichloromethyl, trichloromethyl, Fluoroethyl, difluoroethyl, trifluoroethyl, fluoropropyl, difluoropropyl, trifluoropropyl, chloroethyl, dichloroethyl, trichloroethyl , Phenyl, naphthyl, benzyl, phenylethyl, naphthylmethyl or optionally substituted with methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy or chloroethoxy or Naphthylethyl; or heterocycle or heterocyclic C ₁ -C ₄ -alkyl, in which in each case the heterocycle (also in combination with an alkyl group) is optionally fluorine, chlorine, bromine, cyano, nitro, Carboxyl, methyl, ethyl, n- or i-
Propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl,
Furyl optionally substituted with trichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,
A carbamoyltriazolinone of formula (II) above, representing a group from the group consisting of oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl and triazinyl,
(B) Rice herbicides from the following list ("common name" or "code number"): cyclosulfamurone, AK
D-741, Amiprophos (-methyl), Anilophos,
Benfresate, Bensulfuron (-methyl), Benthulide, Bentazone, Bentocarb (Tiobencarb), Benzophenap, Bifenox, Bromobutide, Butachlor, Butamifos, Butenachlor, Kafenstrol, Chlormethoxynil, Chlornitrophen, Symmethyline, CL-303569, CL-303.
578, Cinosulfuron, Kromeprop, 2,4-
D, cyhalofop-butyl, dimepiperate, dimetamethrin, dithiopyr, azimuthulfuron, zimuron (daimlon), esprocarb, GS-32911,
HOE-404, HOE-30374, HOK-750
1, etobanzanide, imazosulfuron, cumyluron,
KIH-911 (KUH-911), KIH920 (K
UH920), triazophenamide, KPP-31
4, MCPA, MCPB, mefenacet, molinate, NC-310, NC-311, nabroanilide, nitrophen, tenylchlor, oxadiazone, piperophos, pretilachlor, promethrin, propanil, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxifene, pyributycarb, quinclolac, cimetrine, cimetrine. , Trifluralin and X-52, generally 0.1 to 1 per part by weight of the active compound of group 1
A herbicidal composition according to the invention in which 0 parts by weight of the active compound of group 2 are distributed in each case.

Examples of compounds of formula (I) for use as a mixing component according to the invention are given in the group below.

Group 1

[0015]

[Chemical 7]

R ³ here has the meanings given below by way of example: methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino. , N-pentylsulfonylamino, trifluoromethylsulfonylamino, trifluoroethylsulfonylamino, chloromethylsulfonylamino, chloroethylsulfonylamino, chloropropylsulfonylamino,
Cyclopropylsulfonylamino, phenylsulfonylamino, p-tolylsulfonylamino, N-methyl-N
-Methylsulfonyl-amino, N-methyl-N-ethylsulfonyl-amino, N-methyl-Nn-propylsulfonyl-amino, N-methyl-N-i-propylsulfonyl-amino, N-methyl-N-n -Butylsulfonyl-amino, N-methyl-N-i-butylsulfonyl-
Amino, N-methyl-N-s-butylsulfonyl-amino, N-methyl-Nt-butylsulfonyl-amino,
N-methyl-N-n-pentylsulfonyl-amino, N
-Methyl-N-trifluoromethylsulfonyl-amino, N-methyl-N-trifluoroethylsulfonyl-
Amino, N-methyl-N-chloromethylsulfonyl-amino, N-methyl-N-chloroethylsulfonyl-amino, N-methyl-N-chloropropylsulfonyl-amino, N-methyl-N-cyclopropylsulfonyl-amino, N-methyl-N-phenylsulfonyl-amino, N
-Methyl-Np-tolylsulfonyl-amino, N-ethyl-N-methylsulfonyl-amino, N-ethyl-N
-Ethylsulfonyl-amino, N-ethyl-N-n-propylsulfonyl-amino, N-ethyl-N-i-propylsulfonyl-amino, N-ethyl-Nn-butylsulfonyl-amino, N-ethyl-N -I-butylsulfonyl-amino, N-ethyl-Ns-butylsulfonyl-amino, N-ethyl-Nt-butylsulfonyl-
Amino, N-ethyl-N-n-pentylsulfonyl-amino, N-ethyl-N-trifluoromethylsulfonyl-amino, N-ethyl-N-trifluoroethylsulfonyl-amino, N-ethyl-N-chloromethylsulfonyl -Amino, N-ethyl-N-chloroethylsulfonyl-amino, N-ethyl-N-chloropropylsulfonyl-amino, N-ethyl-N-cyclopropylsulfonyl-amino, N-ethyl-N-phenylsulfonyl-amino, N-ethyl-N-p-tolylsulfonyl-amino,
N, N-bis-methylsulfonyl-amino, N, N-bis-ethylsulfonyl-amino, N, N-bis-n-propylsulfonyl-amino, N, N-bis-i-propylsulfonyl-amino, N, N-bis-n-butylsulfonyl-amino, N, N-bis-cyclopropylsulfonyl-amino, N, N-bis-trifluoromethylsulfonyl-amino, N-methylsulfonyl-N-ethylsulfonyl-amino, N- Methylsulfonyl-N-n-propylsulfonyl-amino, N-methylsulfonyl-N-
i-Propylsulfonyl-amino, N-methylsulfonyl-Nn-butylsulfonyl-amino, N-ethylsulfonyl-Nn-propylsulfonyl-amino, N-
Methylsulfonyl-N-cyclopropylsulfonyl-amino, N-methylsulfonyl-N-trifluoromethylsulfonyl-amino, N-methylsulfonyl-N-trifluoroethylsulfonyl-amino, N-methylsulfonyl-N-chloromethylsulfonyl- Amino, N-methylsulfonyl-N-chloroethylsulfonyl-amino,
N-methylsulfonyl-N-chloropropylsulfonyl-amino, N-methylsulfonyl-N-phenylsulfonyl-amino and N-methylsulfonyl-Np-tolylsulfonyl-amino.

Group 2

[0018]

Embedded image

R ³ has the meanings given here by way of example in group 1 above.

Group 3

[0021]

[Chemical 9]

R ³ has in this case the meanings given for example in group 1 above.

Group 4

[0024]

[Chemical 10]

R ³ here has the meanings given for example in group 1 above.

Group 5

[0027]

[Chemical 11]

R ³ has in this case the meanings given for example in group 1 above.

Group 6

[0030]

[Chemical 12]

R ³ has in this case the meanings given for example in group 1 above.

Group 7

[0033]

[Chemical 13]

R ³ has in this case the meanings given for example in group 1 above.

Group 8

[0036]

Embedded image

R ³ has in this case the meanings given for example in group 1 above.

Group 9

[0039]

[Chemical 15]

R ³ has in this case the meanings given for example in group 1 above.

Group 10

[0042]

Embedded image

R ³ has in this case the meanings given for example in group 1 above.

Group 11

[0045]

[Chemical 17]

R ³ has in this case the meanings given for example in group 1 above.

Group 12

[0048]

Embedded image

R ³ has in this case the meanings given for example in group 1 above.

Group 13

[0051]

[Chemical 19]

R ³ has the meanings given here by way of example in group 1 above.

Group 14

[0054]

Embedded image

R ³ has in this case the meanings given for example in group 1 above.

Group 15

[0057]

[Chemical 21]

R ³ has the meanings given here by way of example in group 1 above.

Group 16

[0060]

[Chemical formula 22]

R ³ has in this case the meanings given for example in group 1 above.

Group 17

[0063]

[Chemical formula 23]

R ³ has in this case the meanings given for example in group 1 above.

Group 18

[0066]

[Chemical formula 24]

R ³ has in this case the meanings given for example in group 1 above.

Group 19

[0069]

[Chemical 25]

R ³ has in this case the meanings given for example in group 1 above.

Group 20

[0072]

[Chemical formula 26]

R ³ has in this case the meanings given for example in group 1 above.

The compounds of formula (I) are described in the above-mentioned patent applications and patent application specifications.

The compounds of formula (II) are known and / or can be prepared by methods known per se (EP-A-571,854, 571,571).
No. 885, No. 572,855, No. 578,090
No. 612,735).

Surprisingly, the formula (I) defined above is
Aryl uracil (or aryl thiouracil)
Alternatively, the combination of the corresponding isomeric compounds of formula (Ia) and the active compounds of group 2 above have a particularly high activity and may be used in various crops, especially rice, or in selective weed control. It was discovered.

Surprisingly, the herbicidal activity of the active compound combinations according to the invention is considerably higher than the sum of the actions of the individual active compounds.

Thus, there are more than just unexpected unexpected synergistic effects and additions of action. The novel active compound combinations are well tolerated in a large number of crops, in particular rice, and the novel active compound combinations also apply to other weeds which may be difficult to control. The novel active compound combinations are thus a valuable prosperity for selective herbicides, especially those which can be applied to rice.

Among the weeds that can be effectively controlled by the active compounds according to the invention are the following: dicotyledonous weeds of the following genera: Sinapis, Lemium, Lepidium, Galium,
The genus Stellaria, the genus Oxate (Matricaria),
Anthemis, Galinsaga (Galins)
oga), genus Chenopodium, nettle (Urtic)
a) genus Senecio, genus Amaranthus, genus Portulaca, genus Xanthium, genus Convolvulus, genus Sweetpotato, Ipomoea,
Polygonum, Sesbania, Ambrosia, Thistle (Cirsium), Cichlid (Carduus), Nogeshi (Sonchus), Solanum (So)
lanum), Capsicum (Rorippa), Scutellaria (Rorippa)
tala), Genus Lindernia, Lamiu
m), Stagweed (Veronica), Abutilon (Abutilo)
n), Emex, Dat
ura), violets (Viola), and genus Galeop (Galeop)
sis), Poppy (Papaver), Centaurea (Centaure)
a), clover (Trifolium), foxtail (Ra)
nunculus) and dandelion (Taraxacum).

Monocot weeds of the following genera: Echinochlo
a), genus Setaria, genus Panicu
m), genus Digitaria, genus Ahl
m), Aedes genus (Poa), Anemones (Fe)
stuca), genus Eleusine, genus Brachyaria (B
rachiaria), Lolium, Bromus, Oven (Avena), Cyperus, Sorghum, Agropyron, Cynodon, Monochoria , Genus Fimbristylis, genus Sagittaria, genus Eleocharis, genus Firefly (Scirpus), genus Paspalum, genus Ischaemum, genus Sphenocle.
a), genus Dactyloctenium, genus Agrostis, genus Alopecurus
And the genus Apera.

However, the use of the active compound combinations according to the invention is in no way restricted to these genera, but extends to other plants in the same way.

The active compound combinations according to the invention have, as already indicated, a good action on broad-leaved weeds and grass weeds, as well as a good tolerance to rice crops. Therefore, the possibility of using them as selective herbicides in rice can be particularly emphasized.

The synergistic effect of the active compound combinations according to the invention is particularly strongly pronounced at certain concentration ratios. However, the weight ratios of the active compounds in the active compound combinations can be varied within relatively wide ranges. Generally, active compound 1 of group 1
0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, particularly preferably 0.1 to 10 parts by weight.
Part by weight of active compound of group 2 is distributed.

The active compounds are impregnated in the customary compositions, for example solutions, emulsions, wettable powders, suspensions, powders, foams, coatings, soluble powders, granules, suspension-emulsifiers, active compounds. It can be converted to very fine capsules in natural and synthetic materials, and polymeric materials.

These compositions are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers and optionally surface-active agents, ie emulsifiers and / or dispersants and / or blowing agents. Manufactured.

When water is used as the extender, for example, an organic solvent can be used as the auxiliary solvent. As liquid solvents, mainly aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane, Or paraffins such as mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycols and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethylformamide and dimethylsulfoxide and water are suitable. .

Solid carriers such as ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, or diatomaceous earth and ground synthetic minerals such as highly disperse silicic acids. , Alumina and silicates are suitable; as a solid carrier for granules, ground and fractionated natural rocks, such as calcite, marble, pumice, sepiolite and dolomite, and inorganic and organic ground synthetic granules and substances. Granules such as sawdust, coconut, corncobs and tobacco stems are suitable; nonionic and anionic emulsifiers as emulsifiers and / or blowing agents such as polyoxyethylene-fatty acid esters, polyoxyethylene fatty alcohols Ethers such as alkylaryl polyglycol ethers Le, alkyl sulfonates, alkyl full sulphates, aryl full phosphonate and albumin hydrolysis products; as dispersing agents there are suitable:, for example lignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethyl cellulose and natural and synthetic polymers in the form of powder, powder or latex such as gum arabic, polyvinyl alcohol and polyvinyl acetate and natural phospholipids such as cephalin and lecithin, and synthetic phospholipids are used in the composition. be able to. Further additives can be mineral and vegetable oils.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes,
And trace amounts of nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The preparations generally contain active compounds of 0.1 to 95.
%, Preferably 0.5 to 90% by weight.

The active compound combinations according to the invention are generally applied in the form of finished preparations. However, it is also possible for the active compounds contained in the active compound combinations to be mixed into the individual preparations during application, ie to be applied in a bath mixture.

The novel active compound combinations can be used for controlling weeds, as such or in the form of their preparations, and also as mixtures with other known rice herbicides, finished preparations or tanks. Mixing is also possible. In addition, other known active compounds, such as fungicides, fungicides, insecticides, acaricides, nematicides, bird repellants, growth promoters, Mixtures with plant nutrients and soil structure improvers are also possible. For certain application purposes, especially after germination, plant-acceptable minerals or vegetable oils (eg commercially available “Oleo
It may be further advantageous to adsorb Dupont 11 E ″) or an ammonium salt such as ammonium sulphate or ammonium thiocyanate.

The active compound combinations according to the invention are used as such or in the form of their preparations or use forms prepared by further dilution from such preparations, for example preparations solutions, suspensions, emulsions, powders, coatings and It can be used in the form of granules. These can be processed in the usual way, for example by watering, spraying or atomising.
g) or by scattering.

The active compound combinations according to the invention can be applied either before or after the germination of the plants.
They can also be mixed in the soil before sowing.

The application rates of the active compound combinations according to the invention can be varied within a substantial range. These essentially depend on the nature of the effect desired. Generally, the application rate is 10 g of active compound combination per hectare of soil surface.
To 10 kg, preferably 50 g to 5 kg, especially 100 g to 2 kg.

Although the individual active compounds show a weak herbicidal action, the combinations according to the invention without exception show a very good and broadly effective control of the weeds occurring mainly in rice, which is a simple summation of the action. Is beyond.

A synergistic effect is always present for herbicides when the control action of the active compound combination is greater than that of the individual active compounds to which it is applied.

The expected effect of two herbicides given can be calculated as follows [Colb (Colb
y), SR; "Calculating synergistic and antagonistic respo
nses of herbicide combinations) ”, Weeds 15, 2
See pages 0-22, 1967]: X =% pkg / ha herbicide A at application rate (Group 1
Of the herbicide B (Group 2) at an application rate of Y =% q kg / ha
Of the active compound) and E = herbicide A at an application rate of p = p and q kg / ha
And the expected damage by B, E = X + Y− (X * Y / 100).

If the actual damage is greater than the calculated value, the combination has an additional one in its action, ie this one shows a synergistic effect.

From the application tests on the active compound combinations according to the invention, it was found that the herbicidal action of the active compound combinations according to the invention is greater than the calculated value, ie that the novel active compound combinations act synergistically.

The main features and aspects of the present invention are as follows.

1. (1) General formula (I)

[0103]

[Chemical 27]

An aryluracil or aryl-thiouracil of the general formula (Ia)

[0105]

[Chemical 28]

In each of the formulas (I) and (Ia), Q ¹ represents oxygen or sulfur, Q ² represents oxygen or sulfur, R ¹ represents hydrogen or halogen and R ² represents halogen or cyano. And R ³ is a group —A ¹ —A ² —A ³
Where A ¹ is a single bond, oxygen, sulfur, —SO
_{-, - SO 2 -, -} CO- or a group -N-A ⁴ - represents, here? A ⁴ represents hydrogen, hydroxyl, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl, or (A ¹⁾ Each is an optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkynediyl, cycloalkanediyl, cycloalkenediyl or arendiyl, A ² is a single bond, oxygen, sulfur, -SO-, -SO ₂ -,
Represents CO or a group -N-A ^4, wherein in A ⁴ is hydrogen, alkyl, aryl, alkylcarbonyl, or represents alkylsulfonyl or arylsulfonyl, or (A ²⁾ are each optionally optionally substituted alkanediyl , Alkenediyl, azaalkenediyl, alkynediyl, cycloalkanediyl, cycloalkenediyl or alendyl, and A ³ is hydrogen, hydroxyl, methcapto, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulfo. , Chlorosulfonyl, halogen or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl, Alkoxy (thio) phosphoryl,
Alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino, alkynyloxycarbonyl, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl. , Cycloalkylalkoxycarbonyl, aryl, aryloxy, arylalkyl, arylalkoxy, aryloxycarbonyl, arylalkoxycarbonyl, heterocycle, heterocyclic alkyl,
Represents heterocyclic alkoxy or heterocyclic alkoxycarbonyl, R ⁴ represents hydrogen, halogen or optionally substituted alkyl, R ⁵ represents hydrogen, halogen or optionally substituted alkyl, and R ⁶ represents hydrogen, hydroxyl, amino or alkyl, alkoxy, alkenyl or alkynyl, each of which may be optionally substituted (“active compound of group 1”), and (2) the following active compound (a) and One or more herbicidally active compounds from a second group of herbicides (“group 2 active compounds”), including / or (b) type: (a) general formula (II)

[0107]

[Chemical 29]

In the formula, R ⁷ and R ⁸ are the same or different and independently of each other are each hydrogen or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, Represents a group from the group consisting of aryl and arylalkyl, and R ⁹ is each optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, aryl, arylalkyl, heterocycle and heterocycle. A carbamoyltetrazolinone representing a group from the group consisting of cyclic alkyl, (b) a rice herbicide from the following list ("common name" or "code number"): cyclosulfamurone, AKD-741, Amiprophos (-methyl), Anilophos, Benfrusate , Bensulfuron (-methyl), bensulide, bentazone, bentiocarb (thiobencarb), benzophenap, bifenox, bromobutide, butachlor, butamifos, butenachlor, cafenstrol, chlormethoxynil, chlornitrophen, symmethyline, CL-303569, C
L-303578, Cinosulfuron, Kromeprop,
2,4-D, cyhalofop-butyl, dimepiperate, dimetamethrin, dithiopyr, azimsulfuron,
Jimron (Daimron), Esplocarb, GS-32
911, HOE-404, HOE-30374, HOK
-7501, etobenzanide, imazosulfuron, cumyluron, KIH-911 (KUH-911), KIH9
20 (KUH920), triazophenamide, KPP
-314, MCPA, MCPB, mefenacet, molinate, NC-310, NC-311, nabroanilide, nitrophen, tenylchlor, oxadiazone, piperophos, pretilachlor, promethrin, propanil, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxifene, pyributicarb, quinclorac, A herbicidal composition characterized by an effective content of a combination of active compounds comprising cimetrin, tolfluralin, X-52.

2. (1) Q ¹ represents oxygen or sulfur, Q ² represents oxygen or sulfur, R ¹ represents hydrogen, fluorine, chlorine or bromine, R ² represents fluorine, chlorine, bromine, iodine or cyano, R ³ is a group -A ¹ -A ²
It represents -A ^3, wherein the A ¹ is a single bond, oxygen, sulfur, -S
_{O -, - SO 2 -,} - CO- or a group -N-A ⁴ - represents, here A ⁴ is hydrogen, hydroxyl, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - alkoxy, phenyl, C ₁ -C ₄ - alkylsulfonyl or phenyl sulfonyl, or (a ¹⁾ are each optionally fluorine, chlorine or bromine substituted C ₁ optionally -C ₆ - alkanediyl, C
₂ -C ₆ - alkenediyl, C _{2 ~C 6} - aza alkenediyl, C _{2 ~C 6} - alkynediyl, C ₃ ~C ₆ - cycloalkanediyl, C ₃ ~C ₆ - represents a cycloalkene diyl or phenylene, A ² is a single bond, oxygen, sulfur, -SO
_{-, - SO 2 -, -} CO- or a group -N-A ⁴ - represents, here A ⁴ is hydrogen, hydroxyl, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - alkoxy, phenyl, C ₁ ˜C ₄ -alkylsulfonyl or phenylsulfonyl, or (A ² ) is optionally C ₁ -C ₆ -alkanediyl, C optionally substituted by fluorine, chlorine or bromine, respectively.
₂ -C ₆ - alkanediyl, C ₂ -C ₆ - aza alkenediyl, C ₂ -C ₆ - alkynediyl, C ₃ -C ₆ - cycloalkyl alkanediyl, C ₃ -C ₆ - represents a cycloalkene diyl or phenylene, A ³ is hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulfo,
Chlorosulfonyl, halogen; each having 1 to 6 carbon atoms in the alkyl group, and optionally halogen or C
Alkyl optionally substituted with _1- C ₄ -alkoxy,
Alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio)
Phosphoryl; alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyl, each having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl group and each optionally substituted with halogen. Oxy, alkynylamino or alkynyloxycarbonyl; each having 1 to 4 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl group, and each optionally halogen, cyano, carboxyl, C ₁ -C ₄ - alkyl and / or C ₁ -C ₄ - alkoxy - cycloalkyl which may be substituted with carbonyl, cycloalkyloxy, cycloalkylalkyl, cycloalkyl alkoxycarbonyl, cycloalkylidene amino, cycloalkyloxy carbonitrile Le or cycloalkyl alkoxycarbonyl; or each optionally a nitro, cyano, carboxyl, halogen, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - alkyloxy, C ₁ -C ₄ - halogenoalkyl aryloxy and / or C ₁ -C ₄ - alkoxy - phenyl optionally substituted with carbonyl, phenyloxy, phenyl -C ₁ -C ₄ - alkyl, phenyl -C ₁ -C ₄ - alkoxy, phenyloxycarbonyl Or phenyl-C ₁ -C ₄ -alkoxycarbonyl,
Pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, optionally completely or partially hydrogenated in each case
Thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C ₁ -C ₄ -alkyl, furyl-C ₁
-C ₄ - alkyl, thienyl -C ₁ -C ₄ - alkyl, oxazolyl -C ₁ -C ₄ - alkyl, isoxazolyl -C
₁ -C ₄ - alkyl, thiazolyl -C ₁ -C ₄ - alkyl,
Pyridinyl -C ₁ -C ₄ - alkyl, pyrimidinyl -C ₁
-C ₄ - alkyl, pyrazolyl methoxy, represents furyl methoxy, par tetrahydropyranyl methoxy or pyridylmethoxy, R ⁴ is hydrogen, fluorine, chlorine, bromine or optionally fluorine and / or which may be carbon atoms substituted with chlorine 1 Represents an alkyl having from 4 to 4, R ⁵ represents an alkyl having from 1 to 4 carbon atoms, optionally substituted with hydrogen, fluorine, chlorine, bromine or fluorine and / or chlorine, and R ⁶ represents hydrogen. , Hydroxyl, amino or alkyl, alkoxy, alkenyl or alkynyl each having up to 4 carbon atoms and each optionally substituted with fluorine, chlorine or cyano, A compound of (Ia), and (2) the following types of active compounds (a) and / or (b) Up to 6 each carbon atoms; (a) R ⁷ and R ⁸ are identical or different and hydrogen in each case independently of one another: 1 to 3 kinds of active compounds from the second group of non-herbicide And optionally each of halogen, cyano or C ₁ -C ₄
-Alkyl, alkenyl or alkynyl optionally substituted with alkoxy; each having from 3 to 8 carbon atoms in the cycloalkyl moiety and optionally 5 carbon atoms in the cycloalkenyl moiety.
Or 6 and optionally 1 to 4 carbon atoms in the alkyl part and each optionally halogen, cyano, carboxyl, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy-
Cycloalkyl, cycloalkenyl or cycloalkylalkyl optionally substituted with carbonyl; or each optionally halogen, cyano, nitro, carboxyl, C
₁ -C ₄ - alkyl, C _{1 ~C 4} - halogenoalkyl, C ₁
Represents phenyl, naphthyl, phenyl-C ₁ -C ₄ -alkyl or naphthyl-C ₁ -C ₄ -alkyl optionally substituted with ˜C ₄ -alkoxy or C ₁ -C ₄ -halogenoalkoxy, and R ⁹ Each have up to 6 carbon atoms and each is optionally halogen, cyano or C ₁ -C ₄
-Alkyl, alkenyl or alkynyl optionally substituted with alkoxy; each having from 3 to 8 carbon atoms in the cycloalkyl moiety and optionally 5 carbon atoms in the cycloalkenyl moiety.
Or 6 and optionally 1 to 4 carbon atoms in the alkyl part and each optionally halogen, cyano, carboxyl, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -alkoxy-
Cycloalkyl, cycloalkenyl or cycloalkylalkyl optionally substituted with carbonyl; each optionally halogen, cyano, nitro, carboxyl, C ₁ -C ₄
- alkyl, C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ -
Phenyl, naphthyl, phenyl-C ₁ optionally substituted with alkoxy or C ₁ -C ₄ -halogenoalkoxy
-C ₄ - alkyl or naphthyl -C ₁ -C ₄ - alkyl; or each optionally halogen, cyano, nitro, carboxyl, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - Alkoxy or heterocycle optionally substituted with C ₁ -C ₄ -halogenoalkoxy or heterocyclic represents C ₁ -C ₄ -alkyl, wherein the heterocycle is in each case (in combination with alkyl) furyl. , Tetrahydrofuryl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,
A carbamoyltetrazolinone of formula (II) as described in 1 above representing oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl and triazinyl, (b) a rice herbicide from the following list ("common name" or "code number"): Cyclosulfamurone, AKD-741,
Amiprophos (-methyl), Anilophos, Benfresate, Bensulfuron (-methyl), Benthulide, Bentazone, Bentocarb (Tiobencarb), Benzophenap, Bifenox, Bromobutide, Butachlor,
Butamiphos, butenachlor, casfenstrol, chlormethoxynil, chlornitrophen, cinmethyline, CL-303569, CL-303578, shinosulfuron, cromeprop, 2,4-D, cyhalofop-butyl, dimepiperate, dimetamethrin, dithiopyr, azimsulfuron, dimuron (daimlon), Esplocarb, GS-32911, HOE-404, H
OE-30374, HOK-7501, etobenzanide, imazosulfuron, cumyluron, KIH-911
(KUH-911), KIH920 (KUH920),
Triazophenamide, KPP-314, MCPA, M
CPB, mefenacet, molinate, NC-310,
An effective content comprising NC-311, nabroanilide, nitrophen, tenylchlor, oxadiazone, piperofos, pretilachlor, promethrin, propanil, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxifene, pyributicarb, quinclorac, cimetrin, tolufluralin and X-52. 2. The herbicidal composition according to 1 above, which is characterized by a combination of the active compounds of

3. (1) Q ¹ represents oxygen or sulfur, Q ² represents oxygen or sulfur, R ¹ represents hydrogen, fluorine, chlorine or bromine, R ² represents fluorine, chlorine, bromine, iodine or cyano, R ³ is a group -A ¹ -A ²
It represents -A ^3, wherein the A ¹ is a single bond, oxygen, sulfur, -S
_{O -, - SO 2 -,} - CO- or a group -N-A ⁴ - represents, here A ⁴ is hydrogen, hydroxyl, methyl, ethyl, n- or i- propyl, methoxy, ethoxy,
represents n- or i-propoxy, methylsulfonyl or ethylsulfonyl, or (A ¹ ) is methylene, ethane-1,1-diyl, ethane-1,2-diyl,
Propane-1,1-diyl, propane-1,2-diyl,
Propane-1,3-diyl, ethane-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne- Represents 1,3-diyl, A ² is a single bond, oxygen, sulfur, —SO—, —SO ₂ —, —CO— or group —
N-A ⁴ - represents, here A ⁴ is hydrogen, hydroxyl,
Represents methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl, or (A ² ) is methylene, Ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethane-1,2-diyl, propene- 1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-
1,2-diyl or propyne-1,3-diyl, wherein A ³ is hydrogen, hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulfo, fluorine, chlorine, bromine; each optionally fluorine, chlorine, methoxy or ethoxy Optionally substituted with methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- Or i-propoxy, n-, i
-, S- or t-butoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i
-Propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n-
Or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i
-Propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl, dipropoxyphosphoryl or diiso Propoxyphosphoryl; propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, each optionally substituted with fluorine or chlorine. Propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl; each optionally fluorine, chlorine Cyano, carboxyl, methyl, ethyl, n- or i- propyl, methoxycarbonyl or optionally cyclopropyl optionally substituted with ethoxycarbonyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy,
Cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy,
Cyclohexylmethoxy, cyclopentylideneamino,
Cyclohexylideneamino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl; or each optionally nitro, cyano, carboxyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl , Methoxy, ethoxy, n- or i-propyl, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or
Or phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, optionally substituted with ethoxycarbonyl, optionally in each case completely or partially hydrogenated Pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolmethyl, thiazolemethyl Represents pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy, and R ⁴ is hydrogen, fluorine,
Represents chlorine or methyl or ethyl each optionally substituted with fluorine and / or chlorine, and R ⁵ represents hydrogen, fluorine, chlorine or methyl or ethyl optionally each substituted with fluorine and / or chlorine. , And R ⁶ is hydrogen, hydroxyl, amino or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, propenyl or propynyl, each optionally substituted with fluorine, chlorine or cyano. Of formula (I) as described in 1 above,
Or a compound of (Ia), and (2) one or two active compounds from a second group of herbicides comprising the following types of active compounds (a) and / or (b): (a) R ⁷ And R ⁸ are the same or different and each independently of each other hydrogen; methyl, ethyl, n- or i-propyl, n each optionally substituted with fluorine, chlorine, bromine, cyano, methoxy or ethoxy. -, I
-, S- or t-butyl, propenyl, butenyl,
Pentenyl, propynyl, butynyl or pentynyl;
Fluorine, chlorine, bromine, cyano, carboxyl,
Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexyl optionally substituted with methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl. Methyl; or each optionally with fluorine, chlorine, bromine, cyano, nitro, carboxyl, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy. phenyl optionally substituted, represents benzyl or phenylethyl, each optionally fluorine R ^9, chlorine, bromine, cyano, good eye be substituted by methoxy or ethoxy Le, ethyl, n- or i-
Propyl, n-, i-, s- or t-butyl, n
-, I-, s- or t-pentyl, propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl; each optionally fluorine, chlorine, bromine, cyano, carboxyl, methyl, ethyl, n- or i-propyl,
Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted with methoxycarbonyl or ethoxycarbonyl; each optionally fluorine, chlorine, bromine, cyano , Nitro, carboxyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloroethyl, dichloromethyl, trichloromethyl, Fluoroethyl, difluoroethyl, trifluoroethyl, fluoropropyl, difluoropropyl, trifluoropropyl, chloroethyl, dichloroethyl, trichloroethyl , Phenyl, naphthyl, benzyl, phenylethyl, naphthylmethyl or optionally substituted with methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy or chloroethoxy or Naphthylethyl; or heterocycle or heterocyclic C ₁ -C ₄ -alkyl, in which in each case the heterocycle (also in combination with an alkyl group) is optionally fluorine, chlorine, bromine, cyano, nitro, Carboxyl, methyl, ethyl, n- or i-
Propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl,
Furyl optionally substituted with trichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,
A carbamoyltriazolinone of formula (II) as described in 1 above, representing a group from the group consisting of oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl and triazinyl, (b) the following list ("common name" or "code number"): Rice Herbicides from: Cyclosulfamurone, AKD-741, Amiprophos (-Methyl), Anilophos, Benfresate, Bensulfuron (-Methyl), Benthulide, Bentazone, Bentocarb (Tiobencarb), Benzophenap, Bifenox, Bromobutide, Butachlor. , Butamiphos, butenachlor, cafenstrol, chlormethoxynil, chlornitrophen, symmethyline, CL-303569, C
L-303578, Cinosulfuron, Kromeprop,
2,4-D, cyhalofop-butyl, dimepiperate, dimetamethrin, dithiopyr, azimsulfuron,
Jimron (Daimron), Esplocarb, GS-32
911, HOE-404, HOE-30374, HOK
-7501, etobenzanide, imazosulfuron, cumyluron, KIH-911 (KUH-911), KIH9
20 (KUH920), triazophenamide, KPP
-314, MCPA, MCPB, mefenacet, molinate, NC-310, NC-311, nabroanilide, nitrophen, tenylchlor, oxadiazone, piperophos, pretylachlor, promethrin, propanil, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxifene, pyributicarb, quinclorac, 1 above, characterized by a combination of active compounds of an effective content comprising cimetrin, tolfluralin and X-52.
The herbicidal composition according to 1.

4. In the combination of active compounds, the above 1
An aryluracil or arylthiouracil of the general formula (I) according to 1 above, or a herbicide from the group consisting of herbicides of the type of active compounds (a) and / or (b) according to 1. The weight ratio of the compound of the general formula (Ia) described in 1 above, which is an isomer, is 1:
The herbicidal composition according to the above 1, characterized in that it is between 0.001 and 1: 1000.

5. A method for controlling weeds, which comprises causing the combination of active compounds described in any one of 1 to 4 above to act on weeds and / or their habitat.

6. Use of a combination of active compounds according to any of the above 1 to 4 in controlling weeds.

7. 5. A method for producing a herbicidal composition, which comprises mixing the combination of active compounds described in any one of 1 to 4 above with a filler and / or a surfactant.

8. Process for the preparation of the herbicidal composition according to claim 7, characterized in that the preparation contains between 0.1 and 95% by weight of active compound.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Laurent Andre Germany 40764 Langenfuert Dehiyanto-Miebaczha Beek 37 (72) Inventor Mark-Wilhelm Driyuus Germany 40764 Langenfuert Goethesi Jutrace 38

Claims (5)

[Claims] 1. A general formula (I): Of the general formula (Ia) of aryluracil or aryl-thiouracil or isomers thereof In each of the formulas (I) and (Ia), Q ¹ represents oxygen or sulfur, Q ² represents oxygen or sulfur, R ¹ represents hydrogen or halogen, R ² represents halogen or cyano. , R ³ represents a group —A ¹ —A ² —A ³ , where A ¹ is a single bond, oxygen, sulfur, —SO—, —S.
Represents O ₂ —, —CO— or the group —NA ⁴ —, where A ⁴ represents hydrogen, hydroxyl, alkyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl, or (A ¹ ) is each optionally Optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkynediyl, cycloalkanediyl, cycloalkenediyl or arendiyl, A ² is a single bond, oxygen, sulfur, —SO—, —SO ₂ —, CO Or represents a group —NA ⁴ where A ⁴ is hydrogen, alkyl,
Represents an aryl, alkylcarbonyl, alkylsulfonyl or arylsulfonyl, or (A ² ) is an optionally substituted alkanediyl, alkenediyl, azaalkenediyl, alkynediyl, cycloalkanediyl, cycloalkenediyl or arenediyl. And A ³ is hydrogen, hydroxyl, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen or optionally substituted alkyl, alkoxy, alkylthio, Alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl, dialkoxy (thio) phosphoryl, alkenyl, alkenyloxy , Alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl,
Alkynyloxy, alkynylamino, alkynyloxycarbonyl, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl, cycloalkylalkoxycarbonyl, aryl, aryloxy, arylalkyl, arylalkoxy, Represents an aryloxycarbonyl, an arylalkoxycarbonyl, a heterocycle, a heterocyclic alkyl, a heterocyclic alkoxy or a heterocyclic alkoxycarbonyl, R ⁴ represents hydrogen, halogen or optionally substituted alkyl, and R ⁵ represents Represents hydrogen, halogen or optionally substituted alkyl, and R
⁶ represents hydrogen, hydroxyl, amino or alkyl, alkoxy, alkenyl or alkynyl, each of which may be optionally substituted (“active compound of group 1”), and (2) the following active compound (a) and / or Or a second group of herbicides (“group 2
One or more herbicidally active compounds from the active compound ") of :) (a) of the general formula (II) In the formula, R ⁷ and R ⁸ are the same or different, and independently of each other each hydrogen or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl,
Represents a group from the group consisting of cycloalkenyl, cycloalkylalkyl, aryl and arylalkyl, and R ⁹ is each optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, aryl, A carbamoyltetrazolinone, which represents a group from the group consisting of arylalkyl, heterocycle and heterocyclicalkyl, (b) a rice herbicide from the following list ("common name" or "code number"): cyclosul Famron, AK
D-741, Amiprophos (-methyl), Anilophos,
Benfresate, Bensulfuron (-methyl), Benthulide, Bentazone, Bentocarb (Tiobencarb), Benzophenap, Bifenox, Bromobutide, Butachlor, Butamifos, Butenachlor, Kafenstrol, Chlormethoxynil, Chlornitrophen, Symmethyline, CL-303569, CL-303.
578, Cinosulfuron, Kromeprop, 2,4-
D, cyhalofop-butyl, dimepiperate, dimetamethrin, dithiopyr, azimuthulfuron, zimuron (daimlon), esprocarb, GS-32911,
HOE-404, HOE-30374, HOK-750
1, etobanzanide, imazosulfuron, cumyluron,
KIH-911 (KUH-911), KIH920 (K
UH920), triazophenamide, KPP-31
4, MCPA, MCPB, mefenacet, molinate, NC-310, NC-311, nabroanilide, nitrophen, tenylchlor, oxadiazone, piperophos, pretilachlor, promethrin, propanil, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxifene, pyributycarb, quinclolac, cimetrine, cimetrine. , Trifluralin, X-52, an herbicidal composition characterized by an effective content of a combination of active compounds. 2. A combination of active compounds according to claim 1.
An aryluracil or arylthiouracil of the general formula (I) according to claim 1 or a herbicidal active compound from the group consisting of herbicides of the type active compounds (a) and / or (b) according to claim 1 The herbicidal composition according to claim 1, characterized in that the weight ratio of the compound of the general formula (Ia) according to claim 1 which is an isomer of is between 1: 0.001 and 1: 1000. . 3. A method for controlling weeds, which comprises causing the combination of the active compounds according to claim 1 or 2 to act on weeds and / or their habitat. 4. A process for the preparation of a herbicidal composition, characterized in that the active compound combination according to claim 1 or 2 is mixed with a bulking agent and / or a surfactant. 5. Process for the preparation of the herbicidal composition according to claim 4, characterized in that the preparation contains between 0.1 and 95% by weight of active compound.