公开(公告)号：US4058392A

公开(公告)日：1977-11-15

申请号：US395794

申请日：1973-09-10

申请人： Rudolf Thomas ,  Wolfgang Kramer ,  Ludwig Eue ,  Carl Metzger ,  Gerhard Jager

发明人： Rudolf Thomas ,  Wolfgang Kramer ,  Ludwig Eue ,  Carl Metzger ,  Gerhard Jager

IPC分类号： A01N47/28 ,  A01N47/30 ,  A01N47/32 ,  A01N47/34 ,  A01N47/38 ,  C07C67/00 ,  C07C275/04 ,  C07C275/24 ,  C07C275/28 ,  C07C275/30 ,  C07C275/64 ,  C07C313/00 ,  C07C317/28 ,  C07C323/44 ,  C07C127/15 ,  C07C127/17 ,  C07C127/19

CPC分类号： C07C275/64 ,  C07C275/28 ,  C07C275/30

摘要： New N,N'-tetrasubstituted ureas of the formula ##STR1## in which X is oxygen, sulfur or an NR.sup.5 -- or SO.sub.2 --group,R is alkyl or an optionally substituted aryl group, or an optionally substituted aralkyl group,R.sup.1 and R.sup.4 are individually optionally substituted hydrocarbyl which may contain oxygen or sulfur,R.sup.2 is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy or cycloalkyl,R.sup.3 is alkyl, which may optionally be substituted by halogen, or is alkenyl, orR.sup.2 and R.sup.3 conjointly form an alkylene bridge, which can be interrupted by a hetero-atom, such as O, or N-alkyl group and which forms a heterocyclic ring with the adjoining nitrogen atom,R.sup.1 and R.sup.5, independently of one another, are each alkyl or conjointly form an alkylene bridge, which can be interrupted by a hetero-atom, such as O, and which forms a heterocyclic ring with the adjoining nitrogen atom; andY is oxygen or sulfur; are remarkably effective and selective herbicides.

摘要翻译： 式中，X为氧，硫或NR 5 - 或SO 2 - 基团的新的N，N'-四取代脲，R为烷基或任选取代的芳基，或任选取代的芳烷基，R 1和R 4 可以含有氧或硫的单独任选取代的烃基，R 2是任选取代的烷基，任选取代的烯基，任选取代的烷氧基或环烷基，R 3是烷基，其可任选地被卤素取代，或者是烯基，或者R 2和R 3一起形成 亚烷基桥可以被杂原子如O或N-烷基中断，并且与相邻的氮原子，R 1和R 5彼此独立地形成杂环，各自是烷基或共同形成 亚烷基桥，其可以被诸如O的杂原子中断，并且与相邻的氮原子形成杂环; Y为氧或硫; 是非常有效和选择性的除草剂。

公开(公告)号：US3931311A

公开(公告)日：1976-01-06

申请号：US334495

申请日：1973-02-21

申请人： Rudolf Thomas ,  Wolfgang Kramer ,  Ludwig Eue ,  Carl Metzger ,  Gerhard Jager

发明人： Rudolf Thomas ,  Wolfgang Kramer ,  Ludwig Eue ,  Carl Metzger ,  Gerhard Jager

IPC分类号： C07C275/04 ,  C07C67/00 ,  C07C239/00 ,  C07C273/18 ,  C07C275/08 ,  C07C275/24 ,  C07C275/30 ,  C07C275/34 ,  C07C275/64 ,  C07C325/00 ,  C07C335/04 ,  D06P1/649 ,  C07C127/19 ,  C07C157/02

CPC分类号： C07C275/64 ,  C07C273/1854 ,  C07C275/30 ,  C07C275/34 ,  C07C335/04 ,  D06P1/6491

摘要： Novel N,N',N'-trisubstituted N-halogenomethylurea compounds of the formula: ##EQU1## in which R.sup.1 is alkyl, cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl, aryl or aralkyl (each of which may be optionally substituted),R.sup.2 is alkyl, alkenyl, alkynyl or alkoxy (each of which may be optionally substituted), or halogenoalkyl or cycloalkyl,R.sup.3 is alkyl (which may be optionally halogen-substituted), alkenyl or alkynyl, orR.sup.2 and R.sup.3 jointly represent an alkylene bridge which, can be interrupted by one or more hetero-atoms, such as S or O, or by the NH group, and which forms a heterocyclic ring with the adjoining nitrogen atom,X is oxygen or sulfur, andY is chlorine or bromine.Are prepared by reacting a N,N',N'-trisubstituted urea or thiourea of the general formula: ##EQU2## in which R.sup.1, R.sup.2, R.sup.3 and X have the above-mentioned meanings, is reacted, per mole thereof, with at least 1 mole of formaldehyde (which may be formed in situ from a formaldehyde-releasing substance) and a halogenating agent at a temperature of from -10.degree. to +150.degree.C, optionally in the presence of a diluent and, as a catalyst, a proton-releasing compound (for example a hydrogen halide) or a Lewis acid.

摘要翻译： 新的N，N'，N'-三取代的N-卤代甲基脲化合物，其分子式为：XR2 PARALLEL R1-NCN ANGLE（I）| CH2YR3，其中R1是烷基，环烷基，环烯基，双环烷基，双环烯基，芳基或芳烷基 可以任选被取代），R 2是烷基，烯基，炔基或烷氧基（各自可以是任选取代的）或卤代烷基或环烷基，R 3是烷基（其可以是卤素取代的），烯基或炔基，或者R 2和 R3共同表示亚烷基桥，其可以被一个或多个杂原子如S或O或NH基中断，并且与相邻的氮原子形成杂环，X是氧或硫，以及 Y是氯或溴。

公开(公告)号：US4195181A

公开(公告)日：1980-03-25

申请号：US771729

申请日：1977-02-24

申请人： Carl Metzger ,  Ludwig Eue ,  Robert R. Schmidt

发明人： Carl Metzger ,  Ludwig Eue ,  Robert R. Schmidt

IPC分类号： C07D285/12 ,  C07D285/135 ,  A01N9/12 ,  C07D417/04

CPC分类号： C07D285/135

摘要： New heterocyclic-substituted 1,3,4,-thiadiazole derivatives of the formula ##STR1## in which R.sup.1 is alkyl, alkenyl, haloalkyl, optionally substituted aralkyl, optionally substituted aryl, alkylthio, alkylsulfonyl, alkylsulfoxyl, aralkylthio, aralkylsulfonyl or aralkylsulfoxyl,R.sup.2 is methyl or ethyl, andn is 1 or 2,are surprisingly effective as herbicides and are particularly useful as selective herbicides for combating grasses, especially in crops of cereals or cotton.

摘要翻译： 新的具有式（I）的杂环取代的1,3,4 - 噻二唑衍生物，其中R 1是烷基，烯基，卤代烷基，任选取代的芳烷基，任选取代的芳基，烷硫基，烷基磺酰基，烷基亚砜基，芳烷硫基，芳烷基磺酰基或 芳烷基亚磺酰基，R 2为甲基或乙基，n为1或2，作为除草剂令人惊奇地有效，并且特别用作防治草，特别是谷类或棉花作物的选择性除草剂。

公开(公告)号：US4128412A

公开(公告)日：1978-12-05

申请号：US821031

申请日：1977-08-01

申请人： Carl Metzger ,  Ludwig Eue ,  Helmuth Hack

发明人： Carl Metzger ,  Ludwig Eue ,  Helmuth Hack

IPC分类号： C07D285/12 ,  C07D285/135 ,  A01N9/14 ,  A01N21/02

CPC分类号： C07D285/135

摘要： 1,3,4-Thiadiazol-5-yl-ureas, i.e. N-[2-(alkyl, alkylmercapto, alkenylmercapto alkynylmercapto, chloro-substituted benzylmercapto, carboxy-alkylmercapto, aminocarbonyl-alkylmercapto, chlorophenyl-aminocarbonyl-alkylmercapto, alkylsulfonyl, benzylsulfonyl and alkoxy)-1,3,4-thiadiazol-5-yl]-N-alkyl-[N'-mono- and N',N'-di-alkyl]-ureas, which possess herbicidal properties, and which may be produced by conventional methods.

摘要翻译： 1,3,4-噻二唑-5-基脲，即N- [2-（烷基，烷基巯基，烯基巯基巯基巯基，氯取代的苄基巯基，羧基 - 烷基巯基，氨基羰基 - 烷基巯基，氯苯基 - 氨基羰基 - 烷基巯基，烷基磺酰基，苄基磺酰基 和烷氧基）-1,3,4-噻二唑-5-基] -N-烷基 - [N' - 单 - 和N'，N'-二 - 烷基] - 脲，它们具有除草性， 通过常规方法生产。

公开(公告)号：US4639526A

公开(公告)日：1987-01-27

申请号：US756284

申请日：1968-08-29

申请人： Carl Metzger ,  Ludwig Eue ,  Helmuth Hack

发明人： Carl Metzger ,  Ludwig Eue ,  Helmuth Hack

IPC分类号： A01N43/82 ,  A01N43/824 ,  A01N47/18 ,  A01N47/22 ,  A01N47/36 ,  C07D285/12

CPC分类号： A01N47/36 ,  A01N43/82 ,  A01N47/18 ,  A01N47/22

摘要： 2-(alkyl, alkenyl and alkylmercapto)-5-[N-(alkanoyl, chloroalkanoyl, alkoxycarbonyl, phenoxy carbonyl, N'-[alkyl and alkenyl]-aminocarbonyl and N'-alkyl-N'-[alkyl and alkenyl]-aminocarbonyl)-amino]-1,3,4-thiadiazoles, i.e. 2-(alkyl, alkenyl and alkylmercapto)-5-[N-(alkanoylamino, chloroalkanoylamino, alkoxycarbonylamino, phenoxycarbonylamino, N'-[alkyl and alkenyl]-ureido and N'-alkyl-N'-[alkyl and alkenyl]-ureido)]-1,3,4-thiadiazoles, which possess herbicidal properties, and which may be produced by conventional methods.

摘要翻译： 2-（烷基，烯基和烷基巯基）-5- [N-（烷酰基，氯代烷酰基，烷氧基羰基，苯氧基羰基，N' - [烷基和链烯基] - 氨基羰基和N'-烷基-N' - [烷基和链烯基] 2-（烷基，烯基和烷基巯基）-5- [N-（烷酰基氨基，氯代烷酰基氨基，烷氧基羰基氨基，苯氧基羰基氨基，N' - [烷基和烯基] - 脲基和 N'-烷基-N' - [烷基和烯基] - 脲基]] - 1,3,4-噻二唑，其具有除草性质，并且可以通过常规方法制备。

公开(公告)号：US3981714A

公开(公告)日：1976-09-21

申请号：US552506

申请日：1975-02-24

申请人： Carl Metzger ,  Ludwig Eue ,  Robert Rudolf Schmidt

发明人： Carl Metzger ,  Ludwig Eue ,  Robert Rudolf Schmidt

IPC分类号： A01N43/824 ,  C07D285/12 ,  C07D285/135 ,  C07D417/04

CPC分类号： C07D285/135 ,  C07D417/04

摘要： Novel cyclic N-thiadiazolyl-(2)-carboxylic acid amide compounds of the formula: ##SPC1##WhereinR is alkyl, haloalkyl, alkylthio, alkylsulfonyl or alkoxy, andN is 1 or 2,Display strong herbicidal properties.

摘要翻译： 下式的新型环状N-噻二唑基 - （2） - 羧酸酰胺化合物：

公开(公告)号：US4049670A

公开(公告)日：1977-09-20

申请号：US579124

申请日：1975-05-19

申请人： Carl Metzger ,  Ludwig Eue ,  Helmuth Hack

发明人： Carl Metzger ,  Ludwig Eue ,  Helmuth Hack

IPC分类号： C07D285/12 ,  C07D285/135

CPC分类号： C07D285/135

摘要： 1,3,4-Thiadiazol-5-yl-ureas, i.e. N-[2-(alkyl, alkylmercapto, alkenylmercapto, alkynylmercapto, chloro-substituted benzylmercapto, carboxy-alkylmercapto, aminocarbonyl-alkylmercapto, chlorophenyl-aminocarbonyl-alkylmercapto, alkylsulfonyl, benzylsulfonyl and alkoxy)-1,3,4-thiadiazol-5-yl]-N-alkyl-[N'-mono- and N',N'-di- alkyl]-ureas, which possess herbicidal properties, and which may be produced by conventional methods.

摘要翻译： 1,3,4-噻二唑-5-基脲，即N- [2-（烷基，烷基巯基，链烯基巯基，炔基巯基，氯取代的苄基巯基，羧基 - 烷基巯基，氨基羰基 - 烷基巯基，氯苯基 - 氨基羰基 - 烷基巯基，烷基磺酰基， 苄基磺酰基和烷氧基）-1,3,4-噻二唑-5-基] -N-烷基 - [N' - 单 - 和N'，N'-二烷基] - 脲，其具有除草性质， 通过常规方法生产。

公开(公告)号：US4154597A

公开(公告)日：1979-05-15

申请号：US804026

申请日：1977-06-06

申请人： Carl Metzger ,  Ludwig Eue ,  Robert R. Schmidt

发明人： Carl Metzger ,  Ludwig Eue ,  Robert R. Schmidt

IPC分类号： A01N43/824 ,  C07D417/04 ,  A01N9/12

CPC分类号： C07D417/04

摘要： 3-(1,3,4-THIADIAZOL-2-YL)-5-ACYLOXY(CARBAMOYLOXY)HYDANTOIN COMPOUNDS OF THE FORMULA: ##STR1## in which R is alkyl, haloalkyl, alkylmercapto or alkylsulfonyl,R.sup.1 is alkyl, andR.sup.2 is alkylcarbonyl, alkoxycarbonyl, alkylcarbamoyl or optionally substituted arylcarbonyl;Are remarkably active as herbicides and are particularly useful as selective herbicides in cotton cultivations or in cereal crops, including corn.

摘要翻译： 式（I）其中R是烷基，卤代烷基，烷基巯基或烷基磺酰基，R 1是烷基，（C 1 -C 6）烷氧基羰基， 并且R 2是烷基羰基，烷氧基羰基，烷基氨基甲酰基或任选取代的芳基羰基; 作为除草剂是可重复使用的，特别适用于选择性除草剂在棉花生产或谷物作物中，包括玉米。

公开(公告)号：US3954785A

公开(公告)日：1976-05-04

申请号：US493198

申请日：1974-07-30

申请人： Carl Metzger ,  Ludwig Eue ,  Wilfried Faust

发明人： Carl Metzger ,  Ludwig Eue ,  Wilfried Faust

IPC分类号： A01N47/36 ,  A01N47/34 ,  A01P13/00 ,  C07D285/12 ,  C07D285/135

CPC分类号： C07D285/135

摘要： New acylated urea compounds of the formula ##EQU1## IN WHICH R.sup.1 is alkyl, haloalkyl or optionally substituted aryl,R.sup.2 and R.sup.3, which may be the same or different, are each alkyl or alkenyl, andAz is a 1,3,4-thiadiazole radical which is linked in the 2-position and is optionally substituted in the 5-position;Exhibit excellent herbicidal activity and can be used as selective or total herbicides.

摘要翻译： 式R 2 R 1 -OC-N-CO-N ANGLE（I）| R 3的新的酰化脲化合物其中R 1是烷基，卤代烷基或任选取代的芳基，R 2和R 3可以相同或不同，各自相同或不同 烷基或烯基，并且Az是在2-位连接并且任选在5-位取代的1,3,4-噻二唑基; 展示优良的除草剂活性，可用作选择性或总量除草剂。

公开(公告)号：USRE30578E

公开(公告)日：1981-04-14

申请号：US853971

申请日：1977-11-22

申请人： Carl Metzger ,  Gerhard Jager ,  Klaus Lurssen

发明人： Carl Metzger ,  Gerhard Jager ,  Klaus Lurssen

IPC分类号： A01N47/20 ,  C07C271/06 ,  C07D307/88

CPC分类号： C07D307/88 ,  A01N47/20 ,  C07C271/06

摘要： New N-arylcarbamic acid esters of the formula ##STR1## in which R is lower aliphatic hydrocarbyl, optionally substituted,R.sup.1, R.sup.2 and R.sup.3, which may be identical or different, are each hydrogen, alkyl, cycloalkyl, alkoxy, haloalkyl or halogen,R.sup.4 is alkyl, alkenyl, cycloalkenyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl or alkylthioalkyl, acylalkyl (i.e., alkanoyloxyalkyl), alkoxycarbonylalkyl, carbalkoxyalkyl, carbalkoxyalkenyl, or an optionally substituted cycloalkyl, aryl, aralkyl, aryloxyalkyl or arylthioalkyl radical, or the grouping ##STR2## wherein R.sup.4' is hydrogen or is defined as R.sup.4 is defined above, andY and Y' are oxygen or sulfur,are outstandingly effective in regulating the growth of plants, i.e., to inhibit, stimulate or alter the growth of plants.